EP0188242A2 - Concentrated aqueous textile softener - Google Patents
Concentrated aqueous textile softener Download PDFInfo
- Publication number
- EP0188242A2 EP0188242A2 EP86100273A EP86100273A EP0188242A2 EP 0188242 A2 EP0188242 A2 EP 0188242A2 EP 86100273 A EP86100273 A EP 86100273A EP 86100273 A EP86100273 A EP 86100273A EP 0188242 A2 EP0188242 A2 EP 0188242A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- quaternary ammonium
- polyglycol ether
- acid
- composition according
- condensation product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004753 textile Substances 0.000 title claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 43
- -1 fatty acid ester Chemical class 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 31
- 229920000151 polyglycol Polymers 0.000 claims abstract description 28
- 239000010695 polyglycol Substances 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000007859 condensation product Substances 0.000 claims abstract description 26
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 26
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 24
- 239000000194 fatty acid Substances 0.000 claims abstract description 24
- 229930195729 fatty acid Natural products 0.000 claims abstract description 24
- 150000001412 amines Chemical class 0.000 claims abstract description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 10
- 229920000768 polyamine Polymers 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 20
- 239000004902 Softening Agent Substances 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 16
- 239000004744 fabric Substances 0.000 claims description 11
- 239000004014 plasticizer Substances 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000003760 tallow Substances 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
- 235000015278 beef Nutrition 0.000 claims description 5
- 239000003205 fragrance Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 4
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 4
- 238000000265 homogenisation Methods 0.000 claims description 4
- 235000011007 phosphoric acid Nutrition 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 2
- OZPJREJEDXNPCQ-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O OZPJREJEDXNPCQ-UHFFFAOYSA-N 0.000 claims 1
- 239000002979 fabric softener Substances 0.000 abstract description 8
- 239000000047 product Substances 0.000 description 28
- 239000012141 concentrate Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 125000005456 glyceride group Chemical group 0.000 description 7
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 235000011837 pasties Nutrition 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- SOIAEOTUSNFHMI-UHFFFAOYSA-N 2-(2-aminoethylamino)ethane-1,1-diol Chemical compound NCCNCC(O)O SOIAEOTUSNFHMI-UHFFFAOYSA-N 0.000 description 1
- HVOBSBRYQIYZNY-UHFFFAOYSA-N 2-[2-(2-aminoethylamino)ethylamino]ethanol Chemical compound NCCNCCNCCO HVOBSBRYQIYZNY-UHFFFAOYSA-N 0.000 description 1
- MESLZMGXRZPRGK-UHFFFAOYSA-N 2-benzyloctan-1-ol Chemical group CCCCCCC(CO)CC1=CC=CC=C1 MESLZMGXRZPRGK-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- PZDTYFSTRBOWET-UHFFFAOYSA-N 3-[2-(2-aminoethylamino)ethylamino]propan-1-ol Chemical compound NCCNCCNCCCO PZDTYFSTRBOWET-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SBJUGTGMGDFDRH-UHFFFAOYSA-L dimethyl(dioctadecyl)azanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC SBJUGTGMGDFDRH-UHFFFAOYSA-L 0.000 description 1
- UAKOZKUVZRMOFN-JDVCJPALSA-M dimethyl-bis[(z)-octadec-9-enyl]azanium;chloride Chemical compound [Cl-].CCCCCCCC\C=C/CCCCCCCC[N+](C)(C)CCCCCCCC\C=C/CCCCCCCC UAKOZKUVZRMOFN-JDVCJPALSA-M 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 229940112041 peripherally acting muscle relaxants other quaternary ammonium compound in atc Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/405—Acylated polyalkylene polyamines
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/42—Amino alcohols or amino ethers
- C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/667—Neutral esters, e.g. sorbitan esters
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Definitions
- the present invention relates to an aqueous concentrated fabric softening agent with particularly good dispersibility in water.
- Aqueous fabric softening agents which are usually added to the last rinsing bath of the washing process in an automatic washing machine for post-treatment of freshly washed laundry, contain about 3 to about 6% fabric softening agents. These are mostly largely water-insoluble quaternary ammonium compounds with 2 long residues in the molecule. One of the most effective compounds of this type is the widely used ditallow alkyl dimethyl ammonium chloride.
- concentrates In addition to these textile softening agents with a relatively low active ingredient content, so-called concentrates have recently become known, which have the advantage of having a larger amount of active ingredient in the same volume. Such fabric softener concentrates contain about 10 to 15% fabric softening agents.
- Particularly highly concentrated fabric softeners even contain about 50% by weight of fabric softening agents.
- Example le for such highly concentrated aqueous textile softening agents are the products of DE-OS 33 14 677.
- the concentrates are either diluted to the usual active ingredient concentration of about 3 to about 6% with water, or correspondingly smaller amounts of the concentrated textile softening agents are added last rinse water added. Both the dilution of the fabric softener concentrates and the flushing of the concentrates into the rinse water place high demands on the distributability of the concentrates in the water.
- the fabric softener concentrates therefore contain emulsifiers or dispersants or auxiliaries and viscosity regulators which belong to a wide variety of substance classes.
- these emulsifiers or dispersants or auxiliary substances in turn do not contribute to the softening of the textiles and are therefore to be regarded as dietary fibers. It has therefore been repeatedly tried to get by with a minimum of such non-softening agents in fabric softeners.
- Particularly suitable quaternary ammonium compounds are those with two long-chain, saturated or unsaturated aliphatic groups each having 14 to 26, in particular essentially 16 to 20, carbon atoms and at least one quaternary nitrogen atom in the molecule.
- the long-chain aliphatic groups can be straight-chain or branched and can accordingly derive from fatty acids or from fatty amines, Guerbetamines or from the alkylamines obtainable by reduction of nitroparaffins.
- the aliphatic groups can also contain ester, ether or amide groups.
- Suitable quaternary ammonium compounds can be derived from ammonia, ie compounds of this type are obtained by alkylating long-chain secondary or tertiary amines.
- Examples of such quaternary compounds are ditallowalkyldimethylammonium chloride distearyl dimethyl ammonium chloride or methosulfate or, dioleyldimethylammonium chloride or methosulfate, Ditalgalkylmethylhydroxyethylammoniumchlorid or methosulfate or Ditalgalklymethylhydroxypropylammoniumchlorid or methosulfate or the adducts of ethylene oxide to said hydroxyalkyl e-D derivatives.
- quaternary ammonium compounds are those by reacting 1 mole of an aminoalkyl ethylenediamines or hydroxyalkylethylenediamines with 2 moles of a long-chain C 14 -C 26 fatty acid or its ester obtainable imidazoline compounds which are subsequently converted into the quaternary imidazolinium compounds by alkylation.
- the anion generally consists of the acid residue contained in the alkylating agent used for the quaternization.
- chloride, bromide, methyl sulfate, ethyl sulfate, methane, ethane or toluenesulfonate are suitable as anions.
- the quaternary ammonium compounds are mixtures of imidazoline derivatives and of ammonia derivatives each with two C 14 -C 26 alkyl or alkenyl groups.
- Quaternary ammonium compounds which are also very suitable are the quaternized esterification products of 1 mol of methyldiethanolamine or methyldipropanolamine or in particular methyldiisopropanolamine with 2 mol of a C gC 22 monocarboxylic acid.
- the condensation products suitable as component b) are the products known from DE-AS 19 22 047, which can be obtained by reacting a natural fat, ie. H. a trifatty acid glyceride from fatty acids containing 8 to 24 carbon atoms and consisting of at least 50% by weight of those with 16 or more carbon atoms per fatty acid residue, with a hydroxyalkyl polyamine which has at least one hydroxyethyl, hydroxypropyl or dihydroxypropyl group and at least 2 nitrogen atoms has bound hydrogen atoms, with the proviso that in this reaction, based on 1 mol of the hydroxyalkyl polyamine, 1/3 mol of the trifatty acid glyceride has been reacted for each primary and secondary amino group present and each hydroxyl group.
- a natural fat ie. H. a trifatty acid glyceride from fatty acids containing 8 to 24 carbon atoms and consisting of at least 50% by weight of those with 16 or more carbon atoms per fatty acid
- Components of an active ingredient for laundry rinse aid consist of quaternary textile softening and / or antimicrobial ammonium compounds.
- the laundry rinse agents of DE-AS 19 22 047 with the active ingredient combination mentioned are distinguished by excellent low-temperature stability.
- Examples of the hydroxyalkylpolyamines mentioned are hydroxyethylethylenediamine, dihydroxyethylethylenediamine, hydroxyethyldiethylenetriamine, hydroxypropyldiethylenetriamine.
- the compounds called "condensation products" for the sake of simplicity are mixtures of different compounds.
- diamide and diamide esters In addition to monoamides, diamide and diamide esters, they contain 10 to 30% by weight of fatty acid partial glycerides (mono- and difatty acid glycerides).
- the fatty acid condensation products can also contain trifatty acid glycerides, free fatty acids, free amine and glycerol as reaction by-products.
- the C 8 -C 22 alkyl / alkenylamine polyglycol ethers (component c) of the fabric softener according to the invention), which are referred to below as fatty amine polyglycol ethers, are compounds whose fatty alkyl or fatty alkenyl radicals contain 8 to 22, preferably 16 to 18, Contains carbon atoms.
- the compounds contain 1 or 2 polyglycol ether residues which are derived from ethylene oxide and / or propylene oxide.
- the number of alkylene oxide groups in the molecule is 2 to 50 and in particular 25. Particularly good results are obtained with the adduct of 25 moles of ethylene oxide and 1 mole of stearylamine.
- the agents according to the invention contain in particular 10 to 40% by weight of the active ingredients a) quaternary ammonium compound and b) condensation product, the weight ratio Ratio of active ingredient a). for active ingredient b) is within the range from 10: 1 to 1:15.
- the water with which the active substance melt is mixed only needs to be heated moderately because of the good water distributability of the concentrates according to the invention; in general, homogenizers with particularly high efficacy are not required for the homogenization of products with low active substance contents, although the use of such devices is generally not harmful and leads particularly quickly to finely divided stable products.
- Products of this type require no or only very small amounts of a viscosity regulator, since the viscosity of these products requires no additional measures or additives for viscosity regulation either immediately after production or after long storage.
- Agents with a total of 10 to 18% by weight of active ingredients a) and b) are therefore preferred.
- the water with which the active substance melt is mixed will heat to temperatures of up to about 80 ° C and use dispersing devices that work with high shear forces.
- viscosity regulators it is also advisable to add viscosity regulators to such concentrates, which will be discussed in more detail later, in order to adjust the viscosity within a desired range during production, during storage and during use.
- viscosity regulators as well as the concentration tion of the active ingredients are obtained as viscous, viscous or pasty active ingredient concentrates, which have in common that they are easily distributable in water both during manufacture and in use and that they practically or only slightly change their viscosity during storage. Pourable products are conveniently filled into bottles, while pasty or viscous products are best filled in tubes or in dispensers for pasty products.
- the softness and the distributability in water of the products according to the invention can be increased further if the products are additionally added with 0.5 to 5% by weight of dispersing and softening polyglycol ethers.
- Suitable polyglycol ethers are derived from ethylene oxide and have a molecular weight in the range from 200 to 8000, preferably in the range from 200 to 1000, and in particular in the range from 400 to 600.
- a further increase in the plasticizing performance of the products according to the invention can be achieved if the Products contain textile softening fatty acid esters; suitable fatty acid esters are fatty acid glycerol esters, of which the trifatty acid glycerol esters are particularly preferred.
- the fatty acid esters are preferably present in the products according to the invention in amounts of 0.05 to 5% by weight. In many cases, the addition of different substances from other classes of compounds also increases the softness and / or the distributability in water.
- Suitable additives are ether amines of the formula R- (C 2 H 4 O) n -NR 1 R 2 .
- R is an alkyl or alkenyl radical having 10 to 20 carbon atoms
- n is a number between 2 and 10
- R 1 and R 2 which may be the same or different, are —C 2 H 4 OH or their esters with C 10 -C 20 monocarboxylic acids or with sulfosuccinic acid or alkali metal salts of these acids.
- Quaternary ammonium salts of the last-mentioned compounds are also very suitable, in which a further alkyl group with 1 to 14 carbon atoms is formed on the nitrogen atom with the formation of a positive charge, which is caused by an anion which produces electroneutrality, as a rule the chloride anion - will be compared.
- Other suitable additives are esters of fatty alcohol, in particular tallow alcohol with optionally hydroxyl; substituted monocarboxylic acids with 1 to 3 carbon atoms.
- high molecular weight polyglycol ethers whose molecular weight in; Range of about 10,000 to 80,000 is suitable.
- 2-benzylalkanol polyglycol ethers with 2 to 10 moles of ethylene oxide as additives, particularly when the underlying alcohol component is 2-benzyloctanol.
- Addition products of 2 to 10 moles of ethylene oxide with branched alcohols, such as isotridecanol and with hydroxyl-substituted fatty alcohols, can in many cases be used successfully as additives.
- 1,4-Alkylglycosides and 2,2-alkylglycosides with alkyl radicals which have 10 to 20 carbon atoms are also suitable additives.
- Products according to the invention with a pH value in the undiluted state of approximately 3.5 to 5 have a particularly favorable viscosity behavior.
- a pH within this range is established either through the use of condensation products, which according to a variant of that described in DE-AS 19 22 047 Were prepared using acid, or this acid is added separately to adjust the desired pH if the condensation product does not contain sufficient or no acid.
- Suitable acids are organic or inorganic, non-surfactant acids, which are water-soluble. Examples of suitable acids are acetic acid, oxalic acid, glycolic acid, lactic acid, citric acid, tartaric acid as well as hydrochloric acid, sulfuric acid or phosphoric acid. Mixtures of the acid mentioned can also be used.
- glycolic acid is preferred, while of the inorganic acids, orthophosphoric acid is preferred for setting the desired pH.
- Viscosity regulators are the water-soluble alkali or alkaline earth metal salts from mono- or polyvalent organic or inorganic acids.
- suitable viscosity regulators are sodium chloride, sodium formate, sodium acetate, magnesium chloride, magnesium sulfate, calcium chloride; Magnesium chloride and calcium chloride are particularly effective viscosity regulators.
- the plasticizer concentrates according to the invention containing textile-softening fatty acid esters can contain the fatty acid ester either in a large deficiency compared to the textile-softening quaternary ammonium compounds or in approximately the same amounts as the textile-softening quaternary ammonium compounds.
- Agents according to the invention with a weight ratio of quaternary ammonium compounds to fatty acid esters in the range from 40: 1 to 100: 1 and in a weight ratio in the range from 2: 1 to 1: 2 have particularly interesting properties and are therefore preferred.
- Plasticizer concentrates containing a) 5 to 10% by weight of quaternary ammonium compounds, b) 1.0 to 6.5% by weight of condensation product, c) 1.0 to 1.8% by weight of fatty amine polyglycol ether are particularly preferred, d) 2 to 3% by weight of polyglycol ether, e) 0.1 to 0.7% by weight of fatty acid ester, f) 0.1 to 2.0% by weight of acid.
- Medium with balanced properties contain a) quaternary ammonium compound D italgalkyldimethylammoniumchlorid, b) a condensation product of beef tallow and hydroxyethylethylenediamine, c) an adduct of 25 moles of ethylene oxide with 1 mol of stearylamine, d) polyglycol ether having a molecular weight of 400, e) Tristearinklaglycerinester and f) orthophosphoric acid.
- quaternary ammonium compound D italgalkyldimethylammoniumchlorid b) a condensation product of beef tallow and hydroxyethylethylenediamine, c) an adduct of 25 moles of ethylene oxide with 1 mol of stearylamine, d) polyglycol ether having a molecular weight of 400, e) Tristearinklareglycerinester and f) orthophosphoric acid.
- the manufacturing process for the products according to the invention has an influence on the properties of the inventions Products assembled according to the requirements.
- a process for the production of the products according to the invention is therefore a further subject of the present invention.
- the process for the preparation of an aqueous concentrated fabric softening agent containing quaternary ammonium textile softening agents and a condensation product of a natural fat and a hydroxyalkyl polyamine is characterized in that the quaternary ammonium compound, condensation product and fatty amine polyglycol ether components, optionally together with a polyglycol ether and a fatty acid ester at temperatures from 50 to 70 ° C mixed together to form a homogeneous melt, this melt at elevated temperature, optionally using a mixing unit which develops strong shear forces, mixed with water which has been heated to temperatures of up to 80 ° C, with homogenization, that the mixture is then cooled and, if appropriate, an acid and, if appropriate, a viscosity regulator and, if appropriate, other
- the temperature of the active substance melt should be chosen so that the melt is a homogeneous mixture.
- the water with which the melt is to be mixed to form a homogeneous dispersion is heated to temperatures of up to 80.degree. It also depends on the concentration and composition of the melt whether a mixing unit that develops strong shear forces and the use of viscosity regulators for homogenization and for setting a desired viscosity is required.
- the acid is added to the cooled, homogenized mixture, a reduction in viscosity generally being observed.
- the viscosity and viscosity of the homogenized dispersion can be controlled within a certain range by the type and amount of the acid added.
- An additional possibility for viscosity regulation is the use of viscosity regulators. Viscosity regulators are therefore used when sufficient viscosity regulation has not been possible due to the production and the acid used. If a viscosity regulator is added, a drastic reduction in the viscosity is generally observed even after the addition of small amounts of viscosity regulator, which represents a further advantage of the agents and the method according to the invention.
- the amount of acid to be used is either equivalent to the amount of fatty amine polyglycol ether used or a small excess or deficit of acid is used. The deviations from an equivalent amount are usually not higher than about 20 mol%.
- Example 1 illustrates the invention without restricting it thereto; the method described for example 1 also applies analogously to the following examples, in which one or the other raw material, insofar as it is not absolutely necessary, is missing in comparison to example 1; Accordingly, the incorporation step for the raw material omitted in comparison with Example 1 is also missing.
- the trifatty acid glyceride is the same raw material as described in Example 1.
- the product according to Example 5 is an easily movable liquid
- the products of Examples 6 and 7 are viscous to pasty
- the product of Example 9 is a paste. Common to all products is good water distribution.
- the trifatty acid glyceride and the isononanoic acid ester are the same raw materials as described in Example 1 and Example 4, respectively. Comparable results were obtained if other quaternary ammonium compounds suitable as fabric softeners were used instead of distearyldimethylammonium chloride. Comparable results were also obtained if, instead of the condensation product based on hardened beef tallow, condensation products based on hardened palm oil, peanut oil or mixtures thereof were used.
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Abstract
Description
Die vorliegende Erfindung betrifft ein wäßriges konzentriertes Textilweichmachungsmittel mit besonders guter Verteilbarkeit in Wasser.The present invention relates to an aqueous concentrated fabric softening agent with particularly good dispersibility in water.
Wäßrige Textilweichmachungsmittel, die zur Nachbehandlung frisch gewaschener Wäsche in der Regel dem letzten Spülbad des Waschprozesses in einer automatischen Waschmaschine zugegeben werden, enthalten etwa 3 bis etwa 6 % textilweichmachende Wirkstoffe. Hierbei handelt es sich meist um weitgehend wasserunlösliche quartäre Ammoniumverbindungen mit 2 langen Resten im Molekül. Zu den wirksamsten Verbindungen dieses Typs gehört das in großem Umfang eingesetzte Ditalgalkyldimethylammoniumchlorid. In jüngster Zeit sind außer diesen Textilweichmachungsmitteln mit einem verhältnismäßig niedrigen Wirkstoffgehalt auch sogenannte Konzentrate bekannt geworden, die den Vorteil haben, eine größere Wirkstoffmenge im gleichen Volumen aufzuweisen. Derartige Weichspülerkonzentrate enthalten etwa 10 bis 15 % textilweichmachende Wirkstoffe. Besonders hoch konzentrierte Textilweichmacher enthalten sogar etwa 50 Gew.-% an textilweichmachenden Wirkstoffen. Beispiele für derart hochkonzentrierte wäßrige Textilweichmachungsmittel sind die Produkte der DE-OS 33 14 677. Beim Gebrauch werden die Konzentrate entweder auf die übliche Wirkstoffkonzentration von ca. 3 bis ca. 6 % mit Wasser verdünnt, oder es werden entsprechend geringere Mengen der konzentrierten Textilweichmachungsmittel dem letzten Spülwasser zugesetzt. Sowohl beim Verdünnen der Textilweichmacherkonzentrate als auch beim Einspülen der Konzentrate in das Spülwasser werden an die Verteilbarkeit der Konzentrate im Wasser hohe Ansprüche gestellt. Zur Verbesserung der Verteilbarkeit in Wasser enthalten daher die Textilweichmacherkonzentrate Emulgatoren bzw. Dispergatoren bzw. Hilfsmittel und Viskositätsregulatoren, die unterschiedlichsten Stoffklassen angehören. Im allgemeinen tragen diese Emulgatoren bzw. Dispergatoren bzw. Hilfsstoffe ihrerseits nicht zur Weichmachung der Textilien bei und sind daher als Ballaststoffe anzusehen. Es ist daher immer wieder versucht worden, mit einem Minimum an derartigen nichtweichmachenden Hilfsmitteln in Weichspülmitteln auszukommen.Aqueous fabric softening agents, which are usually added to the last rinsing bath of the washing process in an automatic washing machine for post-treatment of freshly washed laundry, contain about 3 to about 6% fabric softening agents. These are mostly largely water-insoluble quaternary ammonium compounds with 2 long residues in the molecule. One of the most effective compounds of this type is the widely used ditallow alkyl dimethyl ammonium chloride. In addition to these textile softening agents with a relatively low active ingredient content, so-called concentrates have recently become known, which have the advantage of having a larger amount of active ingredient in the same volume. Such fabric softener concentrates contain about 10 to 15% fabric softening agents. Particularly highly concentrated fabric softeners even contain about 50% by weight of fabric softening agents. Example le for such highly concentrated aqueous textile softening agents are the products of DE-OS 33 14 677. When used, the concentrates are either diluted to the usual active ingredient concentration of about 3 to about 6% with water, or correspondingly smaller amounts of the concentrated textile softening agents are added last rinse water added. Both the dilution of the fabric softener concentrates and the flushing of the concentrates into the rinse water place high demands on the distributability of the concentrates in the water. To improve the distributability in water, the fabric softener concentrates therefore contain emulsifiers or dispersants or auxiliaries and viscosity regulators which belong to a wide variety of substance classes. In general, these emulsifiers or dispersants or auxiliary substances in turn do not contribute to the softening of the textiles and are therefore to be regarded as dietary fibers. It has therefore been repeatedly tried to get by with a minimum of such non-softening agents in fabric softeners.
Es wurde nun überraschenderweise gefunden, daß in bestimmter Weise zusammengesetzte Weichmachungsmittel, die nahezu oder vollständig frei sind von nichttextilweichmachenden Hilfsmitteln, bei ausgezeichneter weichmachender Wirkung besonders gute Verteilbarkeit in Wasser aufweisen. Diese gute Verteilbarkeit wirkt sich nicht nur bei der Anwendung der Weichmachungsmittel im .Wasch- bzw. Nachbehandlungsprozess aus, sondern es wird auch eine besonders einfache Herstellung damit gewährleistet. Gegenstand der vorliegenden Erfindung ist daher ein wäßriges, konzentriertes Textilweichmachungsmittel mit einem Gehalt an textilweichmachenden quartären Ammoniumverbindungen und einem Kondensationsprodukt aus einem natürlichen Fett und einem Hydroxyalkylpolyamin, dadurch gekennzeichnet, daß es als Homogenisat, erhalten durch Vermischen einer Schmelze aus
- a) der quartären Ammoniumverbindung,
- b) dem Kondensationsprodukt aus einem natürlichen Fett und einem Hydroxyalkylpolyamin und
- c) einem dispergierend wirkenden Ca-C22-Alkyl-/Alkenyl- aminpolyglykolether
bei erhöhter Temperatur mit warmem Wasser und anschließendem Abkühlen vorliegt.It has now surprisingly been found that plasticizers composed in a certain way, which are almost or completely free of non-fabric softening auxiliaries, have particularly good dispersibility in water with excellent softening action. This good spreadability not only affects the application of the softening agents in the washing or aftertreatment process, but also ensures particularly simple manufacture. The present invention therefore relates to an aqueous, concentrated textile softening agent with a content of textile softening quaternary ammonium compounds and a condensation product from a natural fat and a hydroxyalkyl polyamine, characterized in that it is obtained as a homogenate by mixing a melt
- a) the quaternary ammonium compound,
- b) the condensation product of a natural fat and a hydroxyalkyl polyamine and
- c) a dispersing Ca-C22 alkyl / alkenyl amine polyglycol ether
at elevated temperature with warm water and then cooling.
Als quartäre Ammoniumverbindungen eignen sich vor allem solche mit zwei langkettigen, gesättigten oder ungesättigten aliphatischen Gruppen mit je 14 bis 26, insbesondere im wesentlichen 16 bis 20, Kohlenstoffatomen und wenigstens einem quartären Stickstoffatom im Molekül. Die langkettigen aliphatischen Gruppen können geradkettig oder verzweigt sein und dementsprechend von Fettsäuren, bzw. von Fettaminen, Guerbetaminen oder aus den durch Reduktion von Nitroparaffinen erhältlichen Alkylaminen abstammen. Die aliphatischen Gruppen können auch Ester-, Ether- oder Amidgruppen enthalten. Geeignete quartäre Ammoniumverbindungen können sich vom Ammoniak ableiten, d. h. man erhält derartige Verbindungen durch Alkylierung von langkettigen sekundären oder tertiären Aminen. Beispiele für derartige Quartärverbindungen sind Distearyldimethylammoniumchlorid bzw. Ditalgalkyldimethylammoniumchlorid oder -methosulfat, Dioleyldimethylammoniumchlorid oder -methosulfat, Ditalgalkylmethylhydroxyethylammoniumchlorid oder -methosulfat oder Ditalgalklymethylhydroxypropylammoniumchlorid oder -methosulfat bzw. die Anlagerungsprodukte von Ethylenoxid an die genannten Hydroxyalkyl-De-rivate. Andere geeignete quartäre Ammoniumverbindungen sind die durch Umsetzung von 1 Mol eines Aminoalkylethylendiamins oder Hydroxyalkylethylendiamins mit 2 Mol einer langkettigen C14-C26-Fettsäure oder deren Ester erhältlichen Imidazolinverbindungen, die anschließend durch Alkylierung in die quartären Imidazoliniumverbindungen übergeführt werden. In allen diesen quartären Ammoniumverbindungen besteht das Anion im allgemeinen aus dem Säurerest, der in dem zur Quaternierung verwendeten Alkylierungsmittel enthalten ist. Beispielsweise kommt als Anion daher Chlorid, Bromid, Methylsulfat, Ethylsulfat, Methan-, Ethan- oder Toluolsulfonat in Frage. Gute Resultate werden auch erhalten, wenn die quartären Ammoniumverbindungen Gemische von Imidazolin-Derivaten und von Ammoniak-Derivaten mit je zwei C14-C26-Alkyl- oder Alkenylgruppen darstellen. Ebenfalls gut geeignete quartäre Ammoniumverbindungen sind die quaternierten Veresterungsprodukte von 1 Mol Methyldiethanolamin oder Methyldipropanolamin oder insbesondere Methyldiisopropanolamin mit 2 Mol einer Cg-C22-Monocarbonsäure.Particularly suitable quaternary ammonium compounds are those with two long-chain, saturated or unsaturated aliphatic groups each having 14 to 26, in particular essentially 16 to 20, carbon atoms and at least one quaternary nitrogen atom in the molecule. The long-chain aliphatic groups can be straight-chain or branched and can accordingly derive from fatty acids or from fatty amines, Guerbetamines or from the alkylamines obtainable by reduction of nitroparaffins. The aliphatic groups can also contain ester, ether or amide groups. Suitable quaternary ammonium compounds can be derived from ammonia, ie compounds of this type are obtained by alkylating long-chain secondary or tertiary amines. Examples of such quaternary compounds are ditallowalkyldimethylammonium chloride distearyl dimethyl ammonium chloride or methosulfate or, dioleyldimethylammonium chloride or methosulfate, Ditalgalkylmethylhydroxyethylammoniumchlorid or methosulfate or Ditalgalklymethylhydroxypropylammoniumchlorid or methosulfate or the adducts of ethylene oxide to said hydroxyalkyl e-D derivatives. Other suitable quaternary ammonium compounds are those by reacting 1 mole of an aminoalkyl ethylenediamines or hydroxyalkylethylenediamines with 2 moles of a long-chain C 14 -C 26 fatty acid or its ester obtainable imidazoline compounds which are subsequently converted into the quaternary imidazolinium compounds by alkylation. In all of these quaternary ammonium compounds, the anion generally consists of the acid residue contained in the alkylating agent used for the quaternization. For example, chloride, bromide, methyl sulfate, ethyl sulfate, methane, ethane or toluenesulfonate are suitable as anions. Good results are also obtained if the quaternary ammonium compounds are mixtures of imidazoline derivatives and of ammonia derivatives each with two C 14 -C 26 alkyl or alkenyl groups. Quaternary ammonium compounds which are also very suitable are the quaternized esterification products of 1 mol of methyldiethanolamine or methyldipropanolamine or in particular methyldiisopropanolamine with 2 mol of a C gC 22 monocarboxylic acid.
Bei den als Bestandteil b) geeigneten Kondensationsprodukten handelt es sich um die aus der DE-AS 19 22 047 bekannten Produkte, die durch Umsetzen eines natürlichen Fetts, d. h. eines Trifettsäureglycerids aus Fettsäuren, die 8 bis 24 Kohlenstoffatome enthalten und zu wenigstens 50 Gew.-% aus solchen mit 16 oder mehr Kohlenstoffatomen pro Fettsäurerest bestehen, mit einem Hydroxyalkylpolyamin, das wenigstens eine Hydroxyethyl-, Hydroxypropyl- oder Dihydroxypropylgruppe und wenigstens 2 an Stickstoff-gebundene Wasserstoffatome besitzt, mit der Maßgabe, daß bei dieser Umsetzung, bezogen auf 1 Mol des Hydroxyalkylpolyamins, für jede darin vorhandene primäre und sekundäre Aminogruppe und jede Hydroxylgruppe 1/3 mol des Trifettsäureglycerids zur Umsetzung gelangt sind, hergestellt werden. Diese Kondensationsprodukte sindThe condensation products suitable as component b) are the products known from DE-AS 19 22 047, which can be obtained by reacting a natural fat, ie. H. a trifatty acid glyceride from fatty acids containing 8 to 24 carbon atoms and consisting of at least 50% by weight of those with 16 or more carbon atoms per fatty acid residue, with a hydroxyalkyl polyamine which has at least one hydroxyethyl, hydroxypropyl or dihydroxypropyl group and at least 2 nitrogen atoms has bound hydrogen atoms, with the proviso that in this reaction, based on 1 mol of the hydroxyalkyl polyamine, 1/3 mol of the trifatty acid glyceride has been reacted for each primary and secondary amino group present and each hydroxyl group. These are condensation products
Bestandteile einer Wirkstoffkomponente für Wäschenachspülmittel. Der zweite Teil dieser Wirkstoffkomponente besteht aus quartären textilweichmachenden und/oder antimikrobiellen Ammoniumverbindungen. Die Wäschenachspülmittel der DE-AS 19 22 047 mit der genannten Wirkstoffkombination zeichnen sich durch eine hervorragende Kältestabilität aus. Beispiele für die genannten Hydroxyalkylpolyamine sind Hydroxyethylethylendiamin, Dihydroxyethylethylendiamin, Hydroxyethyldiethylentriamin, Hydroxypropyldiethylentriamin. Die im folgenden der Einfachheit halber "Kondensationsprodukte" genannten Verbindungen stellen Gemische verschiedener Verbindungen dar. Außer Monoamiden, Diamid und Diamidester enthalten sie 10 bis 30 Gew.-% Fettsäureteilglyceride (Mono- und Difettsäureglyceride). Die Fettsäurekondensationsprodukte können als Reaktionsnebenprodukt auch Trifettsäureglyceride, freie Fettsäuren, freies Amin und Glycerin enthalten.Components of an active ingredient for laundry rinse aid. The second part of this active ingredient component consists of quaternary textile softening and / or antimicrobial ammonium compounds. The laundry rinse agents of DE-AS 19 22 047 with the active ingredient combination mentioned are distinguished by excellent low-temperature stability. Examples of the hydroxyalkylpolyamines mentioned are hydroxyethylethylenediamine, dihydroxyethylethylenediamine, hydroxyethyldiethylenetriamine, hydroxypropyldiethylenetriamine. The compounds called "condensation products" for the sake of simplicity are mixtures of different compounds. In addition to monoamides, diamide and diamide esters, they contain 10 to 30% by weight of fatty acid partial glycerides (mono- and difatty acid glycerides). The fatty acid condensation products can also contain trifatty acid glycerides, free fatty acids, free amine and glycerol as reaction by-products.
Bei den C8-C22-Alkyl-/Alkenylaminpolyglykolethern (Bestandteil c) der erfindungsgemäßen Weichspülmittel), die im folgenden Fettaminpolyglykolether genannt werden, handelt es sich um Verbindungen, deren Fettalkyl- oder Fettalkenyl-Rest 8 bis 22, vorzugsweise 16 bis 18, Kohlenstoffatome enthält. Die Verbindungen enthalten 1 oder 2 Polyglykoletherreste, die sich von Ethylenoxid und/oder Propylenoxid ableiten. Die Anzahl der Alkylenoxidgruppen im Molekül beträgt 2 bis 50 und insbesondere 25. Besonders gute Resultate erhält man mit dem Anlagerungsprodukt von 25 Mol Ethylenoxid an 1 Mol Stearylamin.The C 8 -C 22 alkyl / alkenylamine polyglycol ethers (component c) of the fabric softener according to the invention), which are referred to below as fatty amine polyglycol ethers, are compounds whose fatty alkyl or fatty alkenyl radicals contain 8 to 22, preferably 16 to 18, Contains carbon atoms. The compounds contain 1 or 2 polyglycol ether residues which are derived from ethylene oxide and / or propylene oxide. The number of alkylene oxide groups in the molecule is 2 to 50 and in particular 25. Particularly good results are obtained with the adduct of 25 moles of ethylene oxide and 1 mole of stearylamine.
Die erfindungsgemäßen Mittel enthalten insbesondere 10 bis 40 Gew.-% der Wirkstoffe a) quartäre Ammoniumverbindung und b) Kondensationsprodukt, wobei das Gewichtsverhältnis von Wirkstoff a). zu Wirkstoff b) innerhalb des Bereichs von 10 : 1 bis 1 : 15 liegt. Für die Herstellung von Weichmacherkonzentraten mit einem Wirkstoffgehalt der Wirkstoffe a) und b) im unteren KonzentrationsBereich braucht wegen der guten Wasserverteilbarkeit der erfindungsgemäßen Konzentrate das Wasser, mit dem die Wirkstoffschmelze vermischt wird, nur mäßig erwärmt zu werden; im allgemeinen sind zur Homogenisierung von Produkten mit niedrigen Wirkstoffgehalten auch keine Homogenisiergeräte mit besonders hoher Wirksamkeit erforderlich, obwohl die Verwendung derartiger Geräte in der Regel nicht schädlich ist und besonders rasch zu feinteiligen stabilen Produkten führt. Derartige Produkte benötigen keinen oder nur sehr geringe Mengen eines Viskositätsrsegulators, da die Viskosität dieser Produkte sowohl unmittelbar nach der Herstellung als auch nach längerer Lagerung keine zusätzlichen Maßnahmen oder Additive zur Viskositätsregulierung erfordert. Mittel mit einem Gehalt an den Wirkstoffen a) und b) von insgesamt 10 bis 18 Gew.-% sind daher bevorzugt. Für die Herstellung von ebenfalls bevorzugten höher konzentrierten Weichmachungsmitteln mit einem Gehalt an den Wirkstoffen a) und b) von insgesamt 20 bis 35 Gew.-% ist es zur Erzielung von feinteiligen stabilen Produkten in der Regel erforderlich, das Wasser, mit dem die Wirkstoffschmelze vermischt wird, auf Temperaturen von bis zu etwa 80 °C zu erwärmen und Dispergiergeräte zu verwenden, die mit hohen Scherkräften arbeiten. Außerdem empfiehlt sich, derartigen Konzentraten Viskositätsregulatoren, auf die später noch näher eingegangen wird, zuzusetzen, um die Viskosität während der Herstellung, während der Lagerung und der Verwendung innerhalb eines erwünschten Bereichs einzustellen. Abhängig von der Herstellungsweise und der Verwendung von Viskositätsregulatoren sowie je nach der Konzentration der Wirkstoffe erhält man dünnflüssige, dickflüssige oder auch pastöse Wirkstoffkonzentrate, denen gemeinsam ist, daß sie sowohl bei der Herstellung als auch bei der Verwendung in Wasser leicht verteilbar sind und daß sie ihre Viskosität während der Lagerung praktisch nicht oder nur geringfügig verändern. Gießbare Produkte werden zweckmäßigerweise in Flaschen abgefüllt, während pastenförmige oder auch dickflüssige Produkte am besten in Tuben oder in Spendern für pastenförmige Produkte abgefüllt werden.The agents according to the invention contain in particular 10 to 40% by weight of the active ingredients a) quaternary ammonium compound and b) condensation product, the weight ratio Ratio of active ingredient a). for active ingredient b) is within the range from 10: 1 to 1:15. For the production of plasticizer concentrates with an active substance content of the active substances a) and b) in the lower concentration range, the water with which the active substance melt is mixed only needs to be heated moderately because of the good water distributability of the concentrates according to the invention; in general, homogenizers with particularly high efficacy are not required for the homogenization of products with low active substance contents, although the use of such devices is generally not harmful and leads particularly quickly to finely divided stable products. Products of this type require no or only very small amounts of a viscosity regulator, since the viscosity of these products requires no additional measures or additives for viscosity regulation either immediately after production or after long storage. Agents with a total of 10 to 18% by weight of active ingredients a) and b) are therefore preferred. For the production of likewise preferred highly concentrated plasticizers with a content of the active substances a) and b) of a total of 20 to 35% by weight, it is generally necessary to obtain finely divided stable products, the water with which the active substance melt is mixed will heat to temperatures of up to about 80 ° C and use dispersing devices that work with high shear forces. It is also advisable to add viscosity regulators to such concentrates, which will be discussed in more detail later, in order to adjust the viscosity within a desired range during production, during storage and during use. Depending on the production method and the use of viscosity regulators as well as the concentration tion of the active ingredients are obtained as viscous, viscous or pasty active ingredient concentrates, which have in common that they are easily distributable in water both during manufacture and in use and that they practically or only slightly change their viscosity during storage. Pourable products are conveniently filled into bottles, while pasty or viscous products are best filled in tubes or in dispensers for pasty products.
Die Weichheitsleistung und die Verteilbarkeit in Wasser der erfindungsgemäßen Produkte kann noch gesteigert werden, wenn man den Produkten zusätzlich 0,5 bis 5 Gew.-% dispergierend und weichmachend wirkende Polyglykolether zusetzt. Geeignete Polyglykolether leiten sich von Ethylenoxid ab und haben ein Molgewicht im Bereich von 200 bis 8000, vorzugsweise im Bereich von 200 bis 1 000, und insbesondere im Bereich 400 bis 600. Eine weitere Steigerung der weichmachenden Leistung der erfindungsgemäßen Produkte läßt sich erzielen, wenn die Produkte einen Gehalt an textilweichmachenden Fettsäureestern aufweisen; geeignete Fettsäureester sind Fettsäureglycerinester, wovon die Trifettsäureglycerinester besonders bevorzugt sind. Die Fettsäureester sind in den erfindungsgemäßen Produkten vorzugsweise in Mengen von 0,05 bis 5 Gew.-% enthalten. Auch der Zusatz verschiedener Stoffe aus anderen Verbindungsklassen bewirkt in vielen Fällen eine Steigerung der Weichheitsleistung und/oder der Verteilbarkeit in Wasser. Geeignete Zusätze sind Etheramine der Formel R-(C2H4O)n-NR1R2. In dieser Formel bedeutet R einen Alkyl- oder Alkenylrest mit 10 bis 20 Kohlenstoffatomen, n eine Zahl zwischen 2 und 10, R 1 und R 2, die gleich oder verschieden sein können, bedeuten -C2H4OH oder deren Ester mit C10 - C20-Monocarbonsäuren oder mit Sulfobernsteinsäure bzw. Alkalimetallsalzen dieser Säuren. Gut geeignet sind auch quartäre Ammoniumsalze der zuletzt genann- f ten Verbindungen, bei denen an das Stickstoffatom eine weitere Alkylgruppe mit 1 bis 14 Kohlenstoffatomen unter Ausbildung einer positiven Ladung, die durch ein die Elektroneutralität herstellendes Anion, in der Regel das Chlorid-Anion, ausge- glichen wird. Andere geeignete Zusätze sind Ester von Fettalko- i holen, insbesondere Talgalkohol mit gegebenenfalls hydroxyl- ; substituierten Monocarbonsäuren mit 1 bis 3 Kohlenstoffatomen. Außer den oben genannten niedermolekularen Polyglykolethern sind in manchen erfindungsgemäßen Zusammensetzungen auch hochmolekulare Polyglykolether, deren Molekulargewicht im ; Bereich von etwa 10 000 bis 80 000 liegt, geeignet. Ebenfalls sind 2-Benzylalkanolpolyglykolether mit 2 bis 10 Mol Ethylenoxid als Zusätze geeignet, insbesondere dann, wenn die zugrundeliegende Alkoholkomponente 2-Benzyloctanol ist. Auch Anlagerungsprodukte von 2 bis 10 Mol Ethylenoxid an verzweigte Alkohole, wie beispielsweise Isotridecanol sowie an hydroxylsubstituierte Fettalkohole lassen sich in vielen Fällen mit Erfolg als Zusäzte verwenden. Auch 1,4-Alkylglycoside und 2,2-Alkylglycoside mit Alkylresten, die 10 bis 20 Kohlenstoffatome aufweisen, sind geeignete Zusätze.The softness and the distributability in water of the products according to the invention can be increased further if the products are additionally added with 0.5 to 5% by weight of dispersing and softening polyglycol ethers. Suitable polyglycol ethers are derived from ethylene oxide and have a molecular weight in the range from 200 to 8000, preferably in the range from 200 to 1000, and in particular in the range from 400 to 600. A further increase in the plasticizing performance of the products according to the invention can be achieved if the Products contain textile softening fatty acid esters; suitable fatty acid esters are fatty acid glycerol esters, of which the trifatty acid glycerol esters are particularly preferred. The fatty acid esters are preferably present in the products according to the invention in amounts of 0.05 to 5% by weight. In many cases, the addition of different substances from other classes of compounds also increases the softness and / or the distributability in water. Suitable additives are ether amines of the formula R- (C 2 H 4 O) n -NR 1 R 2 . In this formula, R is an alkyl or alkenyl radical having 10 to 20 carbon atoms, n is a number between 2 and 10, R 1 and R 2 , which may be the same or different, are —C 2 H 4 OH or their esters with C 10 -C 20 monocarboxylic acids or with sulfosuccinic acid or alkali metal salts of these acids. Quaternary ammonium salts of the last-mentioned compounds are also very suitable, in which a further alkyl group with 1 to 14 carbon atoms is formed on the nitrogen atom with the formation of a positive charge, which is caused by an anion which produces electroneutrality, as a rule the chloride anion - will be compared. Other suitable additives are esters of fatty alcohol, in particular tallow alcohol with optionally hydroxyl; substituted monocarboxylic acids with 1 to 3 carbon atoms. In addition to the above-mentioned low molecular weight polyglycol ethers, high molecular weight polyglycol ethers whose molecular weight in; Range of about 10,000 to 80,000 is suitable. Also suitable are 2-benzylalkanol polyglycol ethers with 2 to 10 moles of ethylene oxide as additives, particularly when the underlying alcohol component is 2-benzyloctanol. Addition products of 2 to 10 moles of ethylene oxide with branched alcohols, such as isotridecanol and with hydroxyl-substituted fatty alcohols, can in many cases be used successfully as additives. 1,4-Alkylglycosides and 2,2-alkylglycosides with alkyl radicals which have 10 to 20 carbon atoms are also suitable additives.
Erfindungsgemäße Produkte mit einem pH-Wert in unverdünntem Zustand von etwa 3,5 bis 5 weisen ein besonders günstiges Viskositätsverhalten auf. Ein pH-Wert innerhalb dieses Bereiches stellt sich entweder durch die Verwendung von Kondensationsprodukten ein, die nach einer Variante der in der DE-AS 19 22 047 beschriebenen Herstellungsweise unter Verwendung von Säure hergestellt wurden, oder man setzt zur Einstellung des gewünschten pH-Wertes diese Säure separat zu, falls das Kondensationsprodukt nicht genügend oder gar keine Säure enthält. Geeignete Säuren sind organische oder anorganische, nichttensidische Säuren, die wasserlöslich sind. Beispiele für geeignete Säuren sind Essigsäure, Oxalsäure, Glykolsäure, Milchsäure, Citronensäure, Weinsäure sowie Salzsäure, Schwefelsäure oder Phosphorsäure. Auch Gemische der genannten Säure sind verwendbar. Von den organischen Säuren ist die Glykolsäure bevorzugt, während von den anorganischen Säuren Orthophosphorsäure zur Einstellung des gewünschten pH-Wertes bevorzugt wird.Products according to the invention with a pH value in the undiluted state of approximately 3.5 to 5 have a particularly favorable viscosity behavior. A pH within this range is established either through the use of condensation products, which according to a variant of that described in DE-AS 19 22 047 Were prepared using acid, or this acid is added separately to adjust the desired pH if the condensation product does not contain sufficient or no acid. Suitable acids are organic or inorganic, non-surfactant acids, which are water-soluble. Examples of suitable acids are acetic acid, oxalic acid, glycolic acid, lactic acid, citric acid, tartaric acid as well as hydrochloric acid, sulfuric acid or phosphoric acid. Mixtures of the acid mentioned can also be used. Of the organic acids, glycolic acid is preferred, while of the inorganic acids, orthophosphoric acid is preferred for setting the desired pH.
Besonders wertvolle Eigenschaften weisen Weichmacherkonzentrate auf, deren Zusammensetzung innerhalb der folgenden Konzentrationsbereiche liegt:
- a) 2 bis 12 Gew.-% quartäre Ammoniumverbindungen,
- b) 0,3 bis 25 Gew.-% Kondensationsprodukt, c) 0,3 bis 1,8 Gew.-% Fettaminpolyglykolether, d) 0,5 bis 5 Gew.-% Polyglykolether, e) 0,1 bis 4 Gew.-% Fettsäureester, f) 0,01 bis 3 Gew.-% Säure. Weiterhin enthalten die erfindungsgemäßen Mittel Wasser und sonstige in Weichmachungsmitteln übliche Hilfsstoffe, wie z. B. Konservierungsstoffe, Viskositätsregulatoren, Duftstoffe und Farbstoffe. Zur Vermeidung von Verfärbungen der erfindungsgemäßen Produkte, die durch einen Gehalt der verwendeten Rohstoffe an Schwermetallionen verursacht werden könnte, empfiehlt sich der Zusatz von geringen Mengen Schwermetallkomplexbildner.
- a) 2 to 12% by weight of quaternary ammonium compounds,
- b) 0.3 to 25% by weight of condensation product, c) 0.3 to 1.8% by weight of fatty amine polyglycol ether, d) 0.5 to 5% by weight of polyglycol ether, e) 0.1 to 4% by weight. -% fatty acid ester, f) 0.01 to 3 wt .-% acid. Furthermore, the agents according to the invention contain water and other auxiliaries customary in plasticizers, such as. B. preservatives, viscosity regulators, fragrances and dyes. To avoid discoloration of the products according to the invention, which could be caused by a heavy metal ion content in the raw materials used, the addition of small amounts of heavy metal complexing agents is recommended.
Als Konservierungsstoffe kommen mikrobizid wirkende Verbindungen infrage. Viskositätsregulatoren sind die wasserlöslichen Alkali- oder Erdalkalimetallsalze von ein- oder mehrwertigen organischen oder anorganischen Säuren. Beispiele für geeignete Viskositätsregulatoren sind Natriumchlorid, Natriumformiat, Natriumacetat, Magnesiumchlorid, Magnesiumsulfat, Calciumchlorid; besonders wirksame Viskositätsregulatoren sind Magnesiumchlorid und Calciumchlorid.Compounds which have a microbicidal action are suitable as preservatives. Viscosity regulators are the water-soluble alkali or alkaline earth metal salts from mono- or polyvalent organic or inorganic acids. Examples of suitable viscosity regulators are sodium chloride, sodium formate, sodium acetate, magnesium chloride, magnesium sulfate, calcium chloride; Magnesium chloride and calcium chloride are particularly effective viscosity regulators.
Die erfindungsgemäßen Weichmacherkonzentrate mit einem Gehalt an textilweichmachenden Fettsäureestern können den Fettsäureester entweder in einem großen Unterschuß gegenüber den textilweichmachenden quartären Ammoniumverbindungen oder etwa in gleichen Mengen, wie die textilweichmachenden quartären Ammoniumverbindungen enthalten. Erfindungsgemäße Mittel mit einem Gewichtsverhältnis von quartären Ammoniumverbindungen zu Fettsäureestern im Bereich von 40 : 1 bis 100 : 1 sowie im Gewichtsverhältnis im Bereich von 2 : 1 bis 1 : 2 weisen besonders interessante Eigenschaften auf und sind daher bevorzugt. Besonders bevorzugt sind Weichmacherkonzentrate mit einem Gehalt an a) 5 bis 10 Gew.-% quartären Ammoniumverbindungen, b) 1,0 bis 6,5 Gew.-% Kondensationsprodukt, c) 1,0 bis 1,8 Gew.-% Fettaminpolyglykolether, d) 2 bis 3 Gew.-% Polyglykolether, e) 0,1 bis 0,7 Gew.-% Fettsäureester, f) 0,1 bis 2,0 Gew.-% Säure. Mittel mit besonders ausgewogenen Eigenschaften enthalten a) als quartäre Ammoniumverbindung Ditalgalkyldimethylammoniumchlorid, b) ein Kondensationsprodukt aus Rindertalg und Hydroxyethylethylendiamin, c) ein Anlagerungsprodukt von 25 Mol Ethylenoxid an 1 Mol Stearylamin, d) einen Polyglykolether mit einem Molekulargewicht von 400, e) Tristearinsäureglycerinester und f) Orthophosphorsäure.The plasticizer concentrates according to the invention containing textile-softening fatty acid esters can contain the fatty acid ester either in a large deficiency compared to the textile-softening quaternary ammonium compounds or in approximately the same amounts as the textile-softening quaternary ammonium compounds. Agents according to the invention with a weight ratio of quaternary ammonium compounds to fatty acid esters in the range from 40: 1 to 100: 1 and in a weight ratio in the range from 2: 1 to 1: 2 have particularly interesting properties and are therefore preferred. Plasticizer concentrates containing a) 5 to 10% by weight of quaternary ammonium compounds, b) 1.0 to 6.5% by weight of condensation product, c) 1.0 to 1.8% by weight of fatty amine polyglycol ether are particularly preferred, d) 2 to 3% by weight of polyglycol ether, e) 0.1 to 0.7% by weight of fatty acid ester, f) 0.1 to 2.0% by weight of acid. Medium with balanced properties contain a) quaternary ammonium compound D italgalkyldimethylammoniumchlorid, b) a condensation product of beef tallow and hydroxyethylethylenediamine, c) an adduct of 25 moles of ethylene oxide with 1 mol of stearylamine, d) polyglycol ether having a molecular weight of 400, e) Tristearinsäureglycerinester and f) orthophosphoric acid.
Das Herstellverfahren für die erfindungsgcmäßen Produkte hat einen Einfluß auf die Eigenschaften der erfindungsgemäß zusammengesetzten Produkte. Ein Verfahren zur Herstellung der erfindungsgemäßen Produkte ist daher ein weiterer Gegenstand der vorliegenden Erfindung. Das Verfahren zur Herstellung eines wäßrigen konzentrierten Textilweichmachungsmittels mit einem Gehalt an textilweichmachenden quartären Ammoniumverbindungen und einem Kondensationsprodukt aus einem natürlichen Fett und einem Hydroxyalkylpolyamin ist dadurch gekennzeichnet, daß man die Komponenten quartäre Ammoniumverbindung, Kondensationsprodukt und Fettaminpolyglykolether, gegebenenfalls zusammen mit einem Polyglykolether und einem Fettsäureester bei Temperaturen von 50 bis 70°C unter Bildung einer homogenen Schmelze miteinander vermischt, diese Schmelze bei erhöhter Temperatur gegebenenfalls unter Verwendung eines Mischaggregates, das starke Scherkräfte entwickelt, mit Wasser, das man auf Temperaturen von bis zu 80 °C erwärmt hat, unter Homogenisierung vermischt, daß man die Mischung dann abkühlt und dabei gegebenenfalls eine Säure und gegebenenfalls einen Viskositätsregulator sowie gegebenenfalls weitere in Weichmachungsmitteln übliche Hilfsstoffe zusetzt. Die Temperatur der Wirkstoffschmelze ist so zu wählen, daß die Schmelze eine homogene Mischung darstellt. Je nach der Konzentration und den Mengenverhältnissen der Wirkstoffe in der Schmelze erwärmt man das Wasser, mit dem die Schmelze zu einer homogenen Dispersion vermischt werden soll, auf Temperaturen bis zu 80°C. Von Konzentration und Zusammensetzung der Schmelze hängt es auch ab, ob man ein Mischaggregat, das starke Scherkräfte entwickelt, und die Verwendung von Viskositätsregulatoren zur Homogenisierung und zur Einstellung einer gewünschten Viskosität benötigt. Die Säure setzt man der abgekühlten homogenisierten Mischung zu, wobei in der Regel eine Viskositätserniedrigung beobachtet wird.The manufacturing process for the products according to the invention has an influence on the properties of the inventions Products assembled according to the requirements. A process for the production of the products according to the invention is therefore a further subject of the present invention. The process for the preparation of an aqueous concentrated fabric softening agent containing quaternary ammonium textile softening agents and a condensation product of a natural fat and a hydroxyalkyl polyamine is characterized in that the quaternary ammonium compound, condensation product and fatty amine polyglycol ether components, optionally together with a polyglycol ether and a fatty acid ester at temperatures from 50 to 70 ° C mixed together to form a homogeneous melt, this melt at elevated temperature, optionally using a mixing unit which develops strong shear forces, mixed with water which has been heated to temperatures of up to 80 ° C, with homogenization, that the mixture is then cooled and, if appropriate, an acid and, if appropriate, a viscosity regulator and, if appropriate, other auxiliaries customary in plasticizers are added. The temperature of the active substance melt should be chosen so that the melt is a homogeneous mixture. Depending on the concentration and the proportions of the active ingredients in the melt, the water with which the melt is to be mixed to form a homogeneous dispersion is heated to temperatures of up to 80.degree. It also depends on the concentration and composition of the melt whether a mixing unit that develops strong shear forces and the use of viscosity regulators for homogenization and for setting a desired viscosity is required. The acid is added to the cooled, homogenized mixture, a reduction in viscosity generally being observed.
Durch Art und Menge der zugesetzten Säure läßt sich innerhalb eines gewissen Bereichs die Viskosität der homogenisierten Dispersion steuern. Eine zusätzliche Möglichkeit zur Viskositätsregulierung stellt die Verwendung von Viskositätsregulatoren dar. Man verwendet daher Viskositätsregulatoren dann, wenn durch die Herstellung und die eingesetzte Säure eine ausreichende Viskositätsrsregulierung nicht möglich gewesen ist. Setzt man einen Viskositätsregulator zu, beobachtet man in der Regel bereits nach Zusatz von geringen Mengen Viskositätsregulatoren eine drastische Verringerung der Viskosität, was ein weiterer Vorteil der erfindungsgemäßen Mittel und des erfindungsgemäßen Verfahrens darstellt. Die Menge der einzusetzenden Säure ist entweder der Menge des verwendeten Fettaminpolyglykolethers äquivalent oder es wird ein kleiner Überschuß oder Unterschuß an Säure verwendet. Die Abweichungen von einer äquivalenten Menge liegen in der Regel nicht höher als etwa 20 Mol-%.The viscosity and viscosity of the homogenized dispersion can be controlled within a certain range by the type and amount of the acid added. An additional possibility for viscosity regulation is the use of viscosity regulators. Viscosity regulators are therefore used when sufficient viscosity regulation has not been possible due to the production and the acid used. If a viscosity regulator is added, a drastic reduction in the viscosity is generally observed even after the addition of small amounts of viscosity regulator, which represents a further advantage of the agents and the method according to the invention. The amount of acid to be used is either equivalent to the amount of fatty amine polyglycol ether used or a small excess or deficit of acid is used. The deviations from an equivalent amount are usually not higher than about 20 mol%.
Die folgenden Beispiele illustrieren die Erfindung, ohne sie hierauf zu beschränken; das für Beispiel 1 beschriebene Verfahren gilt sinngemäß auch für die folgenden Beispiele, in denen der eine oder andere Rohstoff, soweit er nicht zwingend erforderlich ist, im Vergleich zu Beispiel 1 fehlt; dementsprechend fehlt dann auch der Einarbeitungsschritt für den gegenüber Beispiel 1 weggelassenen Rohstoff.The following examples illustrate the invention without restricting it thereto; the method described for example 1 also applies analogously to the following examples, in which one or the other raw material, insofar as it is not absolutely necessary, is missing in comparison to example 1; Accordingly, the incorporation step for the raw material omitted in comparison with Example 1 is also missing.
10 Gew.-Teile Ditalgalkyldimethylammoniumchlorid, 1,5 Gew.-Teile eines Kondensationsproduktes (hergestellt, indem man 900 g gehärteten Rindertalg auf 95 °C erwärmt, 114 g N-Hydroxyethylethylendiamin innerhalb von 35 Minuten in den Rindertalg einrührt, 4 Stunden bei 100 °C nachrührt, auf 90 °C abkühlen läßt, 42,6 g 70%ige Glykolsäure hinzugibt und dann noch 30 Minuten bei 90 °C nachrührt), 1,5 Gew.-Teile eines Anlagerungsprodukts von 25 Mol Ethylenoxid an 1 Mol Stearylamin, 1,0 Gew.-Teil eines Polyethylenglykols mit einem Molgewicht von 400, 0,15 Gew.-Teilen Trifettsäureglycerid (1 Gew.-% C14-, 29 Gew.-% C16-, 70 Gew.-% C1a-Fettsäure) wurden in einem temperierbaren Mischbehälter auf 65 °C erhitzt; das Gemisch bildete eine klare dünnflüssige Schmelze. Diese Schmelze wurde in 85 Gew.-Teilen Wasser von 60 °C unter Verwendung eines Intensivmischers (Ystral-Turbine) eingerührt. Nach 10 Minuten Rühren bildete der Ansatz eine homogene Paste. Nach Beginn der Kühlung des Behälter-Inhalts wurde mit Orthephosphorsäure unter weiterem Rühren in der Paste ein pH-Wert von 4,5 eingestellt. Beim Erreichen von 48 °C gab man 0,2 Gew.-Teile MgCl2 . 6 H20 in Form einer 10-gewichtsprozentigen wäßrigen Lösung als Viskositätsregulator zu. Die Viskosität des Ansatzes verringerte sich spontan; sie betrug bei 20 °C 38 mPas. Nach weiterem Abkühlen auf 30 °C (nach 60 Minuten) wurden geringe Mengen Konservierungsmittel, Farbstoff und Duftstoff (Duftnote, frisch/blumig) hinzugeben und vermischt. Nach 40 Minuten betrug die Ansatztemperatur 20 °C und die Viskosität 43 mPas. Diese Viskosität veränderte sich auch nach längerem Lagern nur unwesentlich; das Produkt ließ sich leicht mit Wasser verdünnen.10 parts by weight of ditallow alkyldimethylammonium chloride, 1.5 parts by weight of a condensation product (prepared by heating 900 g of hardened beef tallow to 95 ° C., stirring 114 g of N-hydroxyethylethylenediamine into the beef tallow within 35 minutes, 4 hours at 100 ° C stirred, allowed to cool to 90 ° C, 42.6 g of 70% glycolic acid was added and then stirred for a further 30 minutes at 90 ° C), 1.5 parts by weight of an adduct of 25 moles of ethylene oxide and 1 mole of stearylamine, 1 , 0 part by weight of a polyethylene glycol having a molecular weight of 400, 0.15 parts by weight Trifettsäureglycerid (1 wt .-% C14, 29 G ew .-% C16, 70 wt .-% C 1a fatty acid) were heated to 65 ° C. in a temperature-controlled mixing vessel; the mixture formed a clear, thin melt. This melt was stirred into 85 parts by weight of water at 60 ° C. using an intensive mixer (Ystral turbine). After stirring for 10 minutes, the mixture formed a homogeneous paste. After the contents of the container had started to be cooled, a pH of 4.5 was adjusted with orthephosphoric acid with further stirring in the paste. When the temperature reached 48 ° C 0.2 parts by weight of MgCl 2 . 6 H 2 0 in the form of a 10 weight percent aqueous solution as a viscosity regulator. The viscosity of the batch spontaneously decreased; it was 38 mPas at 20 ° C. After further cooling to 30 ° C (after 60 minutes), small amounts of preservative, dye and fragrance (fragrance, fresh / floral) were added and mixed. After 40 minutes, the batch temperature was 20 ° C. and the viscosity was 43 mPas. This viscosity changed only insignificantly even after prolonged storage; the product was easily diluted with water.
Behandelte man mit diesem Konzentrat, das man auf eine Konzentration von 0,3 g Wirkstoff pro Liter Wasser verdünnt hatte, Textilien .aus Baumwolle, Wolle, synthetischen Fasern und Mischgewebe, so stellte eine Gruppe von 5 in der Beurteilung der Weichheit von Textilien geübten Personen eine ausgezeichnete Weichheit der nach der Behandlung getrockneten Textilien fest. In gleicher Weise, wie in Beispiel 1 beschrieben, wurden die wie folgt zusammengesetzten Weichmacherkonzentrate hergestellt, geprüft und ähnlich gut beurteilt:
Bei dem Trifettsäureglycerid handelt es sich um denselben Rohstoff wie in Beispiel 1 beschrieben.The trifatty acid glyceride is the same raw material as described in Example 1.
Das Produkt gemäß Beispiel 5 ist eine leichtbewegliche Flüssigkeit, die Produkte der Beispiele 6 und 7 sind dickflüssig bis pastös, das Produkt von Beispiel 9 ist eine Paste. Allen Produkten gemeinsam ist die gute Wasserverteilbarkeit.The product according to Example 5 is an easily movable liquid, the products of Examples 6 and 7 are viscous to pasty, the product of Example 9 is a paste. Common to all products is good water distribution.
Bei dem Trifettsäureglycerid und dem Isononansäureester handelt es sich um dieselben Rohstoffe, wie in Beispiel 1 bzw. Beispiel 4 beschrieben. Verwendete man statt Distearyldimethylammoniumchlorid andere als Textilweichmacher geeignete quartäre Ammoniumverbindungen, erhielt man vergleichbare Ergebnisse. Ebenso erhielt man vergleichbare Ergebnisse, wenn man statt des Kondesationsproduktes auf Basis von gehärtetem Rindertalg Kondensationsprodukte auf Basis von gehärtetem Palmöl, Erdnußöl oder deren Mischungen verwendete.The trifatty acid glyceride and the isononanoic acid ester are the same raw materials as described in Example 1 and Example 4, respectively. Comparable results were obtained if other quaternary ammonium compounds suitable as fabric softeners were used instead of distearyldimethylammonium chloride. Comparable results were also obtained if, instead of the condensation product based on hardened beef tallow, condensation products based on hardened palm oil, peanut oil or mixtures thereof were used.
In gleicher Weise wie zuvor beschrieben, lassen sich auch niedriger konzentrierte Textilweichmacher herstellen, die beispielsweise nur etwa 3 bis etwa 8 Gew.-% quartäre Ammoniumverbindungen plus Kondensationsprodukt enthalten; diese Mittel ergeben ohne Zusatz von Viskositätsregulatoren in Wasser leicht verteilbare, dünnflüssige Produkte mit guter Weichmacherwirkung.In the same way as described above, it is also possible to produce lower-concentration textile softeners which contain, for example, only about 3 to about 8% by weight of quaternary ammonium compounds plus condensation product; Without the addition of viscosity regulators, these agents result in easily dispersible, thin-bodied products with good plasticizing effects.
Claims (13)
bei erhöhter Temperatur mit warmem Wasser sowie gegebenenfalls mit sonstigen, in Textilweichmachungsmitteln üblichen Hilfs-, Duft- und Farbstoffen und anschließendem Abkühlen, vorliegt.1. Aqueous, concentrated fabric softening agent with a content of fabric softening quaternary ammonium compounds and a condensation product of a natural fat and a hydroxyalkyl polyamine, characterized in that it is obtained as a homogenate by mixing a melt
at elevated temperature with warm water and, if appropriate, with other auxiliaries, fragrances and colorants customary in textile softening agents and subsequent cooling.
und im übrigen Wasser und sonstige in Weichmachungsmitteln übliche Hilfsstoffe wie Konservierungsstoffe, Viskositätsregulatoren, Duft- und Farbstoffe enthält.8. Agent according to one of claims 1 to 7, characterized in that it
and also contains water and other auxiliaries customary in plasticizers, such as preservatives, viscosity regulators, fragrances and colorants.
enthält.11. Agent according to one of claims 1 to 10, characterized in that it
contains.
enthält.12. Composition according to one of claims 1 to 11, characterized in that the
contains.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT86100273T ATE61627T1 (en) | 1985-01-18 | 1986-01-10 | AQUEOUS CONCENTRATED FABRIC SOFTENER. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853501521 DE3501521A1 (en) | 1985-01-18 | 1985-01-18 | AQUEOUS CONCENTRATED TEXTILE SOFTENER |
| DE3501521 | 1985-01-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0188242A2 true EP0188242A2 (en) | 1986-07-23 |
| EP0188242A3 EP0188242A3 (en) | 1987-12-16 |
| EP0188242B1 EP0188242B1 (en) | 1991-03-13 |
Family
ID=6260135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP86100273A Expired - Lifetime EP0188242B1 (en) | 1985-01-18 | 1986-01-10 | Concentrated aqueous textile softener |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4776965A (en) |
| EP (1) | EP0188242B1 (en) |
| JP (1) | JPS61167083A (en) |
| AT (1) | ATE61627T1 (en) |
| DE (2) | DE3501521A1 (en) |
| ES (1) | ES8705544A1 (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3601856A1 (en) * | 1986-01-23 | 1987-07-30 | Henkel Kgaa | TEXTILE TREATMENT AGENTS |
| EP0280976A2 (en) * | 1987-02-28 | 1988-09-07 | Henkel Kommanditgesellschaft auf Aktien | Liquid textile-treating agent |
| EP0307748A2 (en) * | 1987-09-14 | 1989-03-22 | Henkel Kommanditgesellschaft auf Aktien | Fabric treatment composition |
| WO1991012364A1 (en) * | 1990-02-13 | 1991-08-22 | Henkel Kommanditgesellschaft Auf Aktien | Active agent combination for textile treatment |
| WO1992019714A1 (en) * | 1991-04-30 | 1992-11-12 | The Procter & Gamble Company | Fabric softener containing substituted imidazoline and highly ethoxylated compounds |
| WO1994013772A1 (en) * | 1992-12-16 | 1994-06-23 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous textile softener dispersions |
| EP0671383A1 (en) * | 1994-03-08 | 1995-09-13 | Societe Francaise Hoechst | Softening wax for textiles, process for its preparation, aqueous composition containing it, and its use for the treatment of textiles |
| EP0811680A1 (en) * | 1996-06-03 | 1997-12-10 | The Procter & Gamble Company | Fabric softening compositions |
| EP0811679A1 (en) * | 1996-06-03 | 1997-12-10 | The Procter & Gamble Company | Fabric softening compositions |
| WO1997046654A1 (en) * | 1996-06-03 | 1997-12-11 | The Procter & Gamble Company | Fabric softening compositions |
| EP0831144A1 (en) * | 1996-09-19 | 1998-03-25 | The Procter & Gamble Company | Fabric softening compositions |
| WO2001077434A2 (en) * | 2000-04-12 | 2001-10-18 | Clariant International Ltd. | Non-permanent softening finishing of textile piece goods in jet-dyeing machines, and compositions suitable for this purpose |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2522659B2 (en) * | 1987-03-31 | 1996-08-07 | ライオン株式会社 | Softener composition |
| FR2687397A1 (en) * | 1992-02-17 | 1993-08-20 | Sandoz Sa | NOVEL LOW FOAMING SURFACTANTS, THEIR PREPARATION AND THEIR USE. |
| US5474689A (en) * | 1992-10-27 | 1995-12-12 | The Procter & Gamble Company | Waterless self-emulsifiable chemical softening composition useful in fibrous cellulosic materials |
| US5543067A (en) * | 1992-10-27 | 1996-08-06 | The Procter & Gamble Company | Waterless self-emulsiviable biodegradable chemical softening composition useful in fibrous cellulosic materials |
| DE19732396A1 (en) * | 1997-07-28 | 1999-02-04 | Henkel Kgaa | Low viscosity dispersion for paper and textile treatment |
| DE10134224B4 (en) | 2001-07-13 | 2012-12-20 | Clariant Produkte (Deutschland) Gmbh | Additives for inhibiting gas hydrate formation |
| US7214633B2 (en) | 2001-12-18 | 2007-05-08 | Kimberly-Clark Worldwide, Inc. | Polyvinylamine treatments to improve dyeing of cellulosic materials |
| US6824650B2 (en) | 2001-12-18 | 2004-11-30 | Kimberly-Clark Worldwide, Inc. | Fibrous materials treated with a polyvinylamine polymer |
| US6911114B2 (en) * | 2002-10-01 | 2005-06-28 | Kimberly-Clark Worldwide, Inc. | Tissue with semi-synthetic cationic polymer |
| US7371718B2 (en) * | 2005-04-22 | 2008-05-13 | The Dial Corporation | Liquid fabric softener |
| MX2011001697A (en) | 2008-08-15 | 2011-03-04 | Procter & Gamble | Benefit compositions comprising polyglycerol esters. |
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|---|---|---|---|---|
| FR2040418A1 (en) * | 1969-04-30 | 1971-01-22 | Henkel & Cie Gmbh | |
| EP0056695A2 (en) * | 1981-01-16 | 1982-07-28 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions |
| EP0060003A2 (en) * | 1981-03-07 | 1982-09-15 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions and preparation thereof |
| EP0085933A2 (en) * | 1982-02-06 | 1983-08-17 | Hoechst Aktiengesellschaft | Concentrated laundry softening agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7700444A (en) * | 1976-02-06 | 1977-08-09 | Henkel & Cie Gmbh | DETERGENTS WITH A HYDROXYALKYL AMINES CONTENT. |
| DE2961223D1 (en) * | 1978-06-20 | 1982-01-14 | Procter & Gamble | Washing and softening compositions and processes for making them |
| DE3314677A1 (en) * | 1983-04-22 | 1984-10-25 | Henkel KGaA, 4000 Düsseldorf | MADE-UP TEXTILE SOFTENER CONCENTRATE |
-
1985
- 1985-01-18 DE DE19853501521 patent/DE3501521A1/en not_active Withdrawn
-
1986
- 1986-01-10 AT AT86100273T patent/ATE61627T1/en not_active IP Right Cessation
- 1986-01-10 EP EP86100273A patent/EP0188242B1/en not_active Expired - Lifetime
- 1986-01-10 DE DE8686100273T patent/DE3677998D1/en not_active Expired - Fee Related
- 1986-01-17 ES ES550996A patent/ES8705544A1/en not_active Expired
- 1986-01-18 JP JP61008801A patent/JPS61167083A/en active Pending
-
1987
- 1987-08-19 US US07/088,475 patent/US4776965A/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2040418A1 (en) * | 1969-04-30 | 1971-01-22 | Henkel & Cie Gmbh | |
| EP0056695A2 (en) * | 1981-01-16 | 1982-07-28 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions |
| EP0060003A2 (en) * | 1981-03-07 | 1982-09-15 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions and preparation thereof |
| EP0085933A2 (en) * | 1982-02-06 | 1983-08-17 | Hoechst Aktiengesellschaft | Concentrated laundry softening agents |
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| Title |
|---|
| CHEMICAL ABSTRACTS, Band 103, Nr. 10, September 1985, Seite 90, Zusammenfassung Nr. 72894n, Columbus, Ohio, US; & ES-A-523 600 (SOCIEDAD ANON. CAMP FABRICA DE JABONES) 01-11-1984 * |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3601856A1 (en) * | 1986-01-23 | 1987-07-30 | Henkel Kgaa | TEXTILE TREATMENT AGENTS |
| EP0230910A2 (en) * | 1986-01-23 | 1987-08-05 | Henkel Kommanditgesellschaft auf Aktien | Means for treating textiles |
| EP0230910A3 (en) * | 1986-01-23 | 1988-06-08 | Henkel Kommanditgesellschaft Auf Aktien | Means for treating textiles |
| US4865768A (en) * | 1986-01-23 | 1989-09-12 | Henkel Kommanditgesellschaft Auf Aktien | Phosphoric acid salt of the reaction product of a mono-carboxylic acid with a polyamine |
| EP0280976A2 (en) * | 1987-02-28 | 1988-09-07 | Henkel Kommanditgesellschaft auf Aktien | Liquid textile-treating agent |
| EP0280976A3 (en) * | 1987-02-28 | 1989-09-13 | Henkel Kommanditgesellschaft auf Aktien | Liquid textile-treating agent |
| EP0307748A2 (en) * | 1987-09-14 | 1989-03-22 | Henkel Kommanditgesellschaft auf Aktien | Fabric treatment composition |
| EP0307748A3 (en) * | 1987-09-14 | 1990-03-21 | Henkel Kommanditgesellschaft auf Aktien | Fabric treatment composition |
| WO1991012364A1 (en) * | 1990-02-13 | 1991-08-22 | Henkel Kommanditgesellschaft Auf Aktien | Active agent combination for textile treatment |
| WO1992019714A1 (en) * | 1991-04-30 | 1992-11-12 | The Procter & Gamble Company | Fabric softener containing substituted imidazoline and highly ethoxylated compounds |
| WO1994013772A1 (en) * | 1992-12-16 | 1994-06-23 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous textile softener dispersions |
| EP0671383A1 (en) * | 1994-03-08 | 1995-09-13 | Societe Francaise Hoechst | Softening wax for textiles, process for its preparation, aqueous composition containing it, and its use for the treatment of textiles |
| FR2717181A1 (en) * | 1994-03-08 | 1995-09-15 | Hoechst France | Softening wax for textiles, process for its preparation, aqueous compositions containing it and its applications for the treatment of textiles. |
| EP0811680A1 (en) * | 1996-06-03 | 1997-12-10 | The Procter & Gamble Company | Fabric softening compositions |
| EP0811679A1 (en) * | 1996-06-03 | 1997-12-10 | The Procter & Gamble Company | Fabric softening compositions |
| WO1997046654A1 (en) * | 1996-06-03 | 1997-12-11 | The Procter & Gamble Company | Fabric softening compositions |
| EP0831144A1 (en) * | 1996-09-19 | 1998-03-25 | The Procter & Gamble Company | Fabric softening compositions |
| WO2001077434A2 (en) * | 2000-04-12 | 2001-10-18 | Clariant International Ltd. | Non-permanent softening finishing of textile piece goods in jet-dyeing machines, and compositions suitable for this purpose |
| WO2001077434A3 (en) * | 2000-04-12 | 2002-02-28 | Clariant Int Ltd | Non-permanent softening finishing of textile piece goods in jet-dyeing machines, and compositions suitable for this purpose |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61167083A (en) | 1986-07-28 |
| EP0188242A3 (en) | 1987-12-16 |
| EP0188242B1 (en) | 1991-03-13 |
| US4776965A (en) | 1988-10-11 |
| DE3677998D1 (en) | 1991-04-18 |
| ES8705544A1 (en) | 1987-05-01 |
| ATE61627T1 (en) | 1991-03-15 |
| DE3501521A1 (en) | 1986-07-24 |
| ES550996A0 (en) | 1987-05-01 |
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