EP0038862B1 - Compositions containing amido amine salts, and their use as fabric softeners - Google Patents
Compositions containing amido amine salts, and their use as fabric softeners Download PDFInfo
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- EP0038862B1 EP0038862B1 EP19790301558 EP79301558A EP0038862B1 EP 0038862 B1 EP0038862 B1 EP 0038862B1 EP 19790301558 EP19790301558 EP 19790301558 EP 79301558 A EP79301558 A EP 79301558A EP 0038862 B1 EP0038862 B1 EP 0038862B1
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- European Patent Office
- Prior art keywords
- composition according
- amido amine
- water
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- foregoing
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- 239000000203 mixture Substances 0.000 title claims description 23
- -1 amido amine salts Chemical class 0.000 title claims description 19
- 239000002979 fabric softener Substances 0.000 title claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000006185 dispersion Substances 0.000 claims description 12
- 239000004744 fabric Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003760 tallow Substances 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000002862 amidating effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 238000004383 yellowing Methods 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
- C11D1/38—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
- 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
- D06M13/402—Amides imides, sulfamic acids
- D06M13/405—Acylated polyalkylene polyamines
Definitions
- This invention relates to fabric softener compositions containing amido amino salts, and the use thereof for the treatment of fabrics.
- the five most commonly found active softening agents in consumer products purchased in the U.S.A. are all quaternary nitrogen compounds: (1) a methyl chloride quaternised tertiary amine, (II) a dimethyl sulphate quaternised tertiary amine, (III) a dimethyl sulfphate quaternised polyethoxylated di amido amine, (IV) a dimethyl sulphate quaternised polypropoxylated diamido amine and (V) a dimethyl sulphate quaternised alkyl amido alkyl imidazoline.
- German Patent Application No. 2520150 (Brit. Pat. 1,483,984) for example describes the preparation of a quaternised mixture of a diamido diethylenetriamine and an imidazoline.
- the presence of the quaternised diamido diethylenetriamine is said to lower the softening effect of the mixture compared with the quaternised imidazoline alone but to improve the rewettability of the fabric after washing, which most known fabric softeners reduce.
- the patent implies that quaternised diamido diethylenetriamines alone are not effective fabric softeners.
- unquaternised diamido amines, their salts and partial salts tend to be intractable solids at room temperature, which even on dilution with a suitable solvent e.g. 25% of a lower alkanol such as isopropanol, hexylene glycol, propylene glycol or mixtures thereof, are still to viscous for convenient handling.
- a suitable solvent e.g. 25% of a lower alkanol such as isopropanol, hexylene glycol, propylene glycol or mixtures thereof, are still to viscous for convenient handling.
- Our invention therefore provides a novel composition which comprises (A) a water dispersible salt or partial salt of an amido amine of the average formula: wherein an average of from 20% to 80% of the R groups per molecule are acyl groups having an average of from 12 to 22 and preferably 16 to 18 carbon atoms, at least 20% of the R groups are -CH 2 CH 2 0H or -CH Z CH(OH)CH 3 or mixtures of these groups and any other R group is hydrogen, n is 2 or 3 and m is an integer from 2 to 5; which amido amine is at least partially (e.g. from 10% to 80%, preferably 20 to 60%) neutralised with a lower carboxylic or hydroxycarboxylic acid, e.g.
- acetic, formic, propionic, lactic or glycollic acid and (B) a compatible amount, up to 70% preferably 10 to 50%, e.g. 25% by weight, of a fluid, water miscible hydroxyaliphatic solvent.
- R groups are acyl they can be saturated, e.g. stearoyl, monounsaturated, e.g. oleoyl, polyunsaturated or may be mixtures of these types.
- the preferred compounds are those wherein n and m are each 2.
- the acyl groups are derived from tallow or lard.
- any water miscible hydroxy-, or polyhydroxy- alkane or alkylether having a viscosity of less than 0.03 N.S.M.- 2 (30 centipoise) at 20°C may be used as the solvent.
- Preferred examples include isopropanol, hexylene glycol, propylene glycol, ethylene glycol monomethylether and mixtures thereof.
- the product may additionally contain a minor proportion of salts of inorganic acids especially sulphites, which help to stabilise the product against oxidation.
- the amido amines may be obtained by controlled alkoxylation of an amido amine prepared by amidating a polyalkylene polyamine, e.g. by heating it with the necessary amount of a glyceryl ester to provide the desired alkyl groups in the correct proportions.
- the polyamine may be heated with a fatty acid or methyl ester thereof while distilling off water or methanol respectively.
- the heating is carried out at temperatures above 100°C but not sufficiently high to decompose any glycerol formed.
- the temperature should be maintained below 180°C and preferably at 120 to 160°C, e.g. 140°C.
- Heating is preferably carried in an inert atmosphere to prevent colour degradations, e.g. under nitrogen for from 2 to 6, preferably 4 hours.
- the product may then be reacted with ethylene or propylene oxide at a temperature between 100 and 200°C.
- the presence of a catalyst should generally be avoided in order to prevent formation of polyoxyalkylene chains.
- the solvent may be added after alkoxylation to facilitate dispersion of the product in water.
- the invention provides softening compositions comprising the amido amine salts, any glycerol remaining from the preparation of the diamide and the added solvent.
- the novel products of our invention may be used in conventional manner, e.g. as a post-rinse after washing.
- substantially monoethoxylated products of our invention are significantly more fluid in the presence of organic solvent than corresponding non-ethoxylated diamidoamines.
- the vessel was evacuated and flushed with nitrogen to displace most of the air.
- the reactor charge was then cooled to 120°C and 132 kg of ethylene oxide fed in slowly cooling to maintain 120°C.
- the product is a hazy, mobile, pumpable liquid at 20°C.
- the above preparation was repeated but without the addition of solvents.
- the product was a waxy solid which was fluid at 40 to 45°C. On dilution to 75% with isopropanol the product became pourable at 20°C.
- Domestic fabric softener formulations normally consist of concentrated fabric softener solutions as prepared in examples 1 and 2 dispersed into water to yield translucent liquids containing normally 2% to 8% "active" softener.
- active we mean the non solvent component in a fabric softener concentrate.
- Example 3 the appearance and stability of the aqueous dispersion of the concentrates is important for consumer acceptability. Products which yield stable dispersions with viscosities in the range 0.1 to 0.5 N.S.M.- 2 (100 to 500 centipoise) as measured by a "Brookfield" viscometer, model LVT, find ready consumer acceptability. Products which give dispersions which change viscosity on storage are obviously undesirable.
- types II, III, IV and V give dispersions at 6% "active" with viscosities in the range 0.01 to 0.03 N.S.M.- 2 (10 to 30 cp) and are often formulated with other additives to increase their viscosity.
- Dispersions prepared from products of examples 1 and 2 are stable to extend storage.
- the weight of active material used was in the range 0.1 to 0.3% of the napkin weight.
- the napkins were then wrung out by hand and dried on a clothes line under the same conditions.
- Example 2 shows better rewettability properties than type I which has a similar softening ability.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
- This invention relates to fabric softener compositions containing amido amino salts, and the use thereof for the treatment of fabrics.
- It has been proposed that certain quaternised amido amines, quaternised imidazolines prepared by cyclising amido amines, quaternised mixtures of imidazolines and amido amines, and quaternised tertiary amines impart good softening and rewettability properties to fabrics when applied after washing, and especially after washing in non-soap detergents.
- The more effective of the known fabric softening compounds, those that have hitherto actually been used commercially, are all relatively expensive and inconvenient to make. The majority are quaternary ammonium salts which are quaternised by means of reagents such as dimethyl sulphate or methyl chloride. These reagents are highly toxic, so that their use is hazardous and requires expensive precautions both to protect workers and to avoid contamination of the product with toxic residues.
- According to R. R. Egan in J. American Oil Chemists Society January 1978 Vol. 55, p 118 to 121, the five most commonly found active softening agents in consumer products purchased in the U.S.A. are all quaternary nitrogen compounds: (1) a methyl chloride quaternised tertiary amine, (II) a dimethyl sulphate quaternised tertiary amine, (III) a dimethyl sulfphate quaternised polyethoxylated di amido amine, (IV) a dimethyl sulphate quaternised polypropoxylated diamido amine and (V) a dimethyl sulphate quaternised alkyl amido alkyl imidazoline.
- German Patent Application No. 2520150 (Brit. Pat. 1,483,984) for example describes the preparation of a quaternised mixture of a diamido diethylenetriamine and an imidazoline. The presence of the quaternised diamido diethylenetriamine is said to lower the softening effect of the mixture compared with the quaternised imidazoline alone but to improve the rewettability of the fabric after washing, which most known fabric softeners reduce. The patent implies that quaternised diamido diethylenetriamines alone are not effective fabric softeners.
- We have now discovered that when unquaternised diamidoamines are partially neutralised, they provide salts which are surprisingly more effective as fabric softeners than any of the fabric softeners in common commercial use, including the quaternised imidazoline softeners and the quaternised imidazoline/amido amine mixtures. They are moreover considerably more convenient to make, and potentially safer, since they do not require the use of highly toxic reagents. Surprisingly, we have also found that they perform better in tests for skin irritancy than current commercially available fabric softeners.
- However, unquaternised diamido amines, their salts and partial salts tend to be intractable solids at room temperature, which even on dilution with a suitable solvent e.g. 25% of a lower alkanol such as isopropanol, hexylene glycol, propylene glycol or mixtures thereof, are still to viscous for convenient handling.
- We have now further discovered that certain unquaternised hydroxyalkyl diamido amine salts, can be obtained as mobile pastes in the presence of the aforesaid solvents, and exhibit much improved handling characteristics, while retaining the desirable softening properties which we have found to be characteristic of the unquaternised diamido amines. The salts also perform well in rewettability tests, which is unusual for such effective softeners. We have not found that the softeners of this invention cause significantly more yellowing of fabric than quaternary softeners.
- Our invention therefore provides a novel composition which comprises (A) a water dispersible salt or partial salt of an amido amine of the average formula:
- The preferred compounds are those wherein n and m are each 2. Preferably the acyl groups are derived from tallow or lard.
- Typically, any water miscible hydroxy-, or polyhydroxy- alkane or alkylether having a viscosity of less than 0.03 N.S.M.-2 (30 centipoise) at 20°C may be used as the solvent. Preferred examples include isopropanol, hexylene glycol, propylene glycol, ethylene glycol monomethylether and mixtures thereof.
- The product may additionally contain a minor proportion of salts of inorganic acids especially sulphites, which help to stabilise the product against oxidation.
- The amido amines may be obtained by controlled alkoxylation of an amido amine prepared by amidating a polyalkylene polyamine, e.g. by heating it with the necessary amount of a glyceryl ester to provide the desired alkyl groups in the correct proportions. Alternatively, the polyamine may be heated with a fatty acid or methyl ester thereof while distilling off water or methanol respectively. Preferably, the heating is carried out at temperatures above 100°C but not sufficiently high to decompose any glycerol formed. To avoid cyclisation and maintain the product as an amido amine the temperature should be maintained below 180°C and preferably at 120 to 160°C, e.g. 140°C.
- Higher temperatures, up to 300°C, particularly with the application of a purge gas or vacuum will cause the amido amine to cyclise to the imidazoline with the loss of water.
- Heating is preferably carried in an inert atmosphere to prevent colour degradations, e.g. under nitrogen for from 2 to 6, preferably 4 hours. The product may then be reacted with ethylene or propylene oxide at a temperature between 100 and 200°C. The presence of a catalyst should generally be avoided in order to prevent formation of polyoxyalkylene chains. The solvent may be added after alkoxylation to facilitate dispersion of the product in water.
- The invention provides softening compositions comprising the amido amine salts, any glycerol remaining from the preparation of the diamide and the added solvent. The novel products of our invention may be used in conventional manner, e.g. as a post-rinse after washing.
- The substantially monoethoxylated products of our invention are significantly more fluid in the presence of organic solvent than corresponding non-ethoxylated diamidoamines.
- To a reactor fitted with a heating/cooling jacket, stirrer and nitrogen purge 1560 kg of deodourised tallow glyceride, mole weight 872, was added and heated to 50°C.
- The vessel was evacuated and flushed with nitrogen to displace most of the air.
- 287 kg of diethylene triamine, 98% purity, was added over 5 minutes, no exotherm was observed, and the charge was heated to 140°C over 60 minutes. This temperature was maintained for 240 minutes whilst a slow stream of nitrogen was passed into the charge. A determination of base value and free ester value of the charge showed that the reaction to form the diamido amine was complete.
-
- To the product of the reaction above at 60-65°C was added propylene glycol and isopropyl alcohol, the solution cooled to 36°C and sulphur dioxide and acetic acid added.
-
- The product is a hazy, mobile, pumpable liquid at 20°C.
- The above preparation was repeated but without the addition of solvents. The product was a waxy solid which was fluid at 40 to 45°C. On dilution to 75% with isopropanol the product became pourable at 20°C.
- The addition of a small quantity of S02 to the di tallow amido amine ethoxylate, which also partially neutralises the amine, allows the use of less acetic acid and overcomes the acetic acid odour which might otherwise be apparent in the concentrate or the diluted fabric softener. The addition of S02 also yields a lighter colour product which is less prone to colour deterioration on storage.
- Domestic fabric softener formulations normally consist of concentrated fabric softener solutions as prepared in examples 1 and 2 dispersed into water to yield translucent liquids containing normally 2% to 8% "active" softener. By "active" we mean the non solvent component in a fabric softener concentrate.
- The ease with which these dispersions can be made is of considerable practical importance to the formulator as is the appearance and storage stability of the formulated dispersions.
-
- As stated in Example 3 the appearance and stability of the aqueous dispersion of the concentrates is important for consumer acceptability. Products which yield stable dispersions with viscosities in the range 0.1 to 0.5 N.S.M.-2 (100 to 500 centipoise) as measured by a "Brookfield" viscometer, model LVT, find ready consumer acceptability. Products which give dispersions which change viscosity on storage are obviously undesirable.
- In general compound type I gives very high viscosity 6% active dispersions which must be reduced by additives and special preparative techniques. (As described in J. Amer. Oil Chem. Soc. Vol 56, p 452, April 1979).
- In general methosulphates, types II, III, IV and V give dispersions at 6% "active" with viscosities in the range 0.01 to 0.03 N.S.M.-2 (10 to 30 cp) and are often formulated with other additives to increase their viscosity.
- 6% active, prepared as in Example 2 dispersed water ― 0.30 N.S.M.-2 (300 cp)
- 6% active, prepared as in Example 2 but 2 moles E.O. -0.17 N.S.M.-z (170 cp)
- 6% active, prepared as in Example 2 but 8 moles E.O. ― 0.03 N.S.M.-2 (30 cp)
- Dispersions prepared from products of examples 1 and 2 are stable to extend storage.
- The product of example 2 was evaluated against compounds of type I and III where n = 1 in a panel evaluation test as follows.
- 6% active dispersions of each material were prepared using soft water (20 ppm). These solutions were then further diluted with water. Napkins woven from 60% cotton and 40% polyester were washed in an automatic washing machine using a conventional low foam automatic washing powder. These napkins were then soaked for 10 minutes at 20 to 25°C in the dilute dispersion of softener.
- The weight of active material used was in the range 0.1 to 0.3% of the napkin weight.
- The napkins were then wrung out by hand and dried on a clothes line under the same conditions.
-
- The significance of these results were assessed using the method devised by Kromer - Journal of Food Technology 1963 - 17/12/124.
- The example 2 product is at least as good as the best commercial type as found by Egen and significantly better than type III, n=1.
-
-
- Using the Kromer method to evaluate these results
-
- For a set of 4 samples and a panel of 20 the significance range is 37 to 58, i.e. there is no significant difference between these 4 samples.
- It is a well known fact that excessive or continual use of certain fabric conditioning materials can produce a waterproofing effect on fabrics. This effect is undesirable, particularly on fabrics designed for their moisture absorbancy e.g. towels and baby diapers.
- Napkins treated by the same technique as that used to prepare the samples for the softening evaluation above were cut into strips and the test strips suspended in an aqueous solution of a dye, Kiton green (0.5 gm/litre, temperature = 20°C).
- The rate at which the dye front travelled above the solution was measured.
-
- The product of Example 2 shows better rewettability properties than type I which has a similar softening ability.
Water hardness 300 ppm.
Claims (8)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE7979301558T DE2966608D1 (en) | 1979-08-03 | 1979-08-03 | Compositions containing amido amine salts, and their use as fabric softeners |
EP19790301558 EP0038862B1 (en) | 1979-08-03 | 1979-08-03 | Compositions containing amido amine salts, and their use as fabric softeners |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP19790301558 EP0038862B1 (en) | 1979-08-03 | 1979-08-03 | Compositions containing amido amine salts, and their use as fabric softeners |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0038862A1 EP0038862A1 (en) | 1981-11-04 |
EP0038862B1 true EP0038862B1 (en) | 1984-02-01 |
Family
ID=8186412
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19790301558 Expired EP0038862B1 (en) | 1979-08-03 | 1979-08-03 | Compositions containing amido amine salts, and their use as fabric softeners |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP0038862B1 (en) |
DE (1) | DE2966608D1 (en) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8508129D0 (en) * | 1985-03-28 | 1985-05-01 | Procter & Gamble Ltd | Textile treatment composition |
DE3601856A1 (en) * | 1986-01-23 | 1987-07-30 | Henkel Kgaa | TEXTILE TREATMENT AGENTS |
FR2613386B1 (en) * | 1987-04-04 | 1993-06-18 | Sandoz Sa | NEW COMPOSITIONS FOR FINISHING FIBROUS MATERIALS |
US4762645A (en) * | 1987-11-16 | 1988-08-09 | The Procter & Gamble Company | Detergent plus softener with amide ingredient |
DE3842057A1 (en) * | 1988-12-14 | 1990-06-28 | Henkel Kgaa | TEXTILE SOFTENER FOR FLEETS WITH HIGH CONTENTS OF ELECTROLYTE AND / OR OPTICAL BRIGHTENER |
DE3901820A1 (en) * | 1989-01-23 | 1990-08-09 | Henkel Kgaa | TEXTILE TREATMENT AGENT |
DE4111648A1 (en) * | 1991-04-10 | 1992-10-15 | Henkel Kgaa | TEXTILE TREATMENT AGENT WITH IMPROVED WATER DISPERSIBILITY |
US5433869A (en) * | 1992-12-22 | 1995-07-18 | Colgate-Palmolive Co. | Liquid fabric conditioning composition containing amidoamine softening compound |
MY108928A (en) * | 1992-12-22 | 1996-11-30 | Colgate Palmolive Co | Liquid fabric softening composition containing amidoamine softening compound |
GB9301811D0 (en) * | 1993-01-29 | 1993-03-17 | Unilever Plc | Fabric softener composition |
DE19625937A1 (en) | 1996-06-28 | 1997-01-23 | Huels Chemische Werke Ag | Prepn. of mono-, or oligo- amide alkoxylate cpds. for surfactant mfr. |
US5747108A (en) * | 1997-03-19 | 1998-05-05 | Colgate-Palmolive Co. | Super-concentrated liquid rinse cycle fabric softening composition |
US5747109A (en) * | 1997-03-19 | 1998-05-05 | Colgate-Palmolive Co. | Method of preparing super-concentrated liquid rinse cycle fabric softening composition |
DE19756680A1 (en) * | 1997-12-19 | 1999-06-24 | Henkel Kgaa | Production of fatty acid aminoamide |
US6780834B2 (en) | 2002-07-31 | 2004-08-24 | Colgate-Palmolive Co. | Fabric conditioning compositions containing an amine acid softening compound |
EP1902083B1 (en) | 2005-06-29 | 2010-10-20 | Colgate-Palmolive Company | Oligomeric amidoamines or amidoquats for fabric or hair treatment compositions |
CA2691188A1 (en) | 2007-06-28 | 2008-12-31 | Achim Hack | Process for preparing 1,4-butandiol mononitrate |
BR112019011016B1 (en) | 2016-12-01 | 2023-04-04 | Croda, Inc | INGREDIENTS FOR USE IN PERSONAL CARE COMPOSITIONS |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3844959A (en) * | 1972-10-16 | 1974-10-29 | Procter & Gamble | Detergent composition with an amido-amine fabric softening agent |
US3933871A (en) * | 1973-11-12 | 1976-01-20 | Armstrong Chemical Company, Inc. | Fabric softener compound and processes for preparing and using the same |
FR2273901A1 (en) * | 1974-06-06 | 1976-01-02 | Azote & Prod Chim | COMPOSITION FOR THE TREATMENT OF TEXTILES |
US4039565A (en) * | 1975-06-26 | 1977-08-02 | Ashland Oil, Inc. | Quaternized amidoamines |
DE2539310A1 (en) * | 1975-09-04 | 1977-03-17 | Hoechst Ag | Textile softener solns. or dispersions - contg. condensate of fatty acid or ester and alkyl propylene diamine oxyalkylate |
-
1979
- 1979-08-03 EP EP19790301558 patent/EP0038862B1/en not_active Expired
- 1979-08-03 DE DE7979301558T patent/DE2966608D1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
EP0038862A1 (en) | 1981-11-04 |
DE2966608D1 (en) | 1984-03-08 |
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