NO125051B - - Google Patents

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Publication number: NO125051B
Authority: NO; Norway
Prior art keywords: parts; weight; volume; solution; water
Prior art date: 1968-07-22

Application number

NO2955/69A

Other languages

English (en)

Norwegian (no)

Inventor

K Lebkuecher

E Nischwitz

E Schinzel

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1968-07-22

Filing date

1969-07-15

Publication date

1972-07-10

1969-07-15 Application filed by Hoechst Ag filed Critical Hoechst Ag

1972-07-10 Publication of NO125051B publication Critical patent/NO125051B/no

Links

-1 Cationic stilbene derivatives Chemical class 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
150000001450 anions Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
238000005282 brightening Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
239000002657 fibrous material Substances 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
150000002430 hydrocarbons Chemical group 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 73
239000000243 solution Substances 0.000 description 72
150000003839 salts Chemical class 0.000 description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
238000003756 stirring Methods 0.000 description 23
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
235000011121 sodium hydroxide Nutrition 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
239000007795 chemical reaction product Substances 0.000 description 15
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 12
159000000000 sodium salts Chemical class 0.000 description 12
238000001816 cooling Methods 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
239000004744 fabric Substances 0.000 description 10
239000011780 sodium chloride Substances 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000002168 alkylating agent Substances 0.000 description 7
229940100198 alkylating agent Drugs 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000005909 Kieselgur Substances 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
125000000129 anionic group Chemical class 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 5
125000002091 cationic group Chemical group 0.000 description 5
229920002678 cellulose Polymers 0.000 description 5
239000001913 cellulose Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
150000004985 diamines Chemical class 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
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 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
229920000742 Cotton Polymers 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000835 fiber Substances 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
238000010409 ironing Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
238000004383 yellowing Methods 0.000 description 4
HHSBHVJQXZLIRW-UHFFFAOYSA-N 3-n,3-n-dimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC=CC(N)=C1 HHSBHVJQXZLIRW-UHFFFAOYSA-N 0.000 description 3
QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920003043 Cellulose fiber Polymers 0.000 description 3
BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
239000002979 fabric softener Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
230000000717 retained effect Effects 0.000 description 3
239000000758 substrate Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000218657 Picea Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000013543 active substance Substances 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000005018 casein Substances 0.000 description 2
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
235000021240 caseins Nutrition 0.000 description 2
239000002752 cationic softener Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 2
REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000011888 foil Substances 0.000 description 2
239000003292 glue Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229940055577 oleyl alcohol Drugs 0.000 description 2
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
239000010414 supernatant solution Substances 0.000 description 2
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
RSAVZMLVLNTTOW-UHFFFAOYSA-N 1-n,1-n,4-trimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC=C(C)C(N)=C1 RSAVZMLVLNTTOW-UHFFFAOYSA-N 0.000 description 1
MKMCBDUEBALBFG-UHFFFAOYSA-N 1-n,1-n-diethyl-4-n-methylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)NC MKMCBDUEBALBFG-UHFFFAOYSA-N 0.000 description 1
CAPCBAYULRXQAN-UHFFFAOYSA-N 1-n,1-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)N CAPCBAYULRXQAN-UHFFFAOYSA-N 0.000 description 1
ZGZHNQPTNCGKHS-UHFFFAOYSA-N 1-n,1-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)CC(C)N ZGZHNQPTNCGKHS-UHFFFAOYSA-N 0.000 description 1
AMQHNJUMJKWREE-UHFFFAOYSA-N 2-chloro-1-n,1-n-dimethylbenzene-1,4-diamine Chemical compound CN(C)C1=CC=C(N)C=C1Cl AMQHNJUMJKWREE-UHFFFAOYSA-N 0.000 description 1
XYOSFLPUWVWHOA-UHFFFAOYSA-N 2-ethylidenepropane-1,3-diol;urea Chemical compound NC(N)=O.CC=C(CO)CO XYOSFLPUWVWHOA-UHFFFAOYSA-N 0.000 description 1
SKJLIATVTKHMNL-UHFFFAOYSA-N 2-methoxyethyl n,n-bis(hydroxymethyl)carbamate Chemical compound COCCOC(=O)N(CO)CO SKJLIATVTKHMNL-UHFFFAOYSA-N 0.000 description 1
HJXIRCMNJLIHQR-UHFFFAOYSA-N 2-n,2-n-dimethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N HJXIRCMNJLIHQR-UHFFFAOYSA-N 0.000 description 1
BZFRCCRHMACPGO-UHFFFAOYSA-N 3-n,3-n,4-trimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC(N)=CC=C1C BZFRCCRHMACPGO-UHFFFAOYSA-N 0.000 description 1
IOUFMOLZROGOAW-UHFFFAOYSA-N 3-n,3-n-diethyl-4-methylbenzene-1,3-diamine Chemical compound CCN(CC)C1=CC(N)=CC=C1C IOUFMOLZROGOAW-UHFFFAOYSA-N 0.000 description 1
KFSNHOUZAIGMAF-UHFFFAOYSA-N 3-n,3-n-diethylbenzene-1,3-diamine Chemical compound CCN(CC)C1=CC=CC(N)=C1 KFSNHOUZAIGMAF-UHFFFAOYSA-N 0.000 description 1
AFHLJRYAVLIEMS-UHFFFAOYSA-N 4-(diethylaminomethyl)aniline Chemical compound CCN(CC)CC1=CC=C(N)C=C1 AFHLJRYAVLIEMS-UHFFFAOYSA-N 0.000 description 1
PEPDSSVIPHINAB-UHFFFAOYSA-N 4-chloro-3-n,3-n-dimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC(N)=CC=C1Cl PEPDSSVIPHINAB-UHFFFAOYSA-N 0.000 description 1
REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 1
101100161935 Caenorhabditis elegans act-4 gene Proteins 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
241000294754 Macroptilium atropurpureum Species 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229920000388 Polyphosphate Polymers 0.000 description 1
229920001131 Pulp (paper) Polymers 0.000 description 1
239000004902 Softening Agent Substances 0.000 description 1
FPVLWAAVKMZUJN-UHFFFAOYSA-N [4-[(dimethylamino)methyl]cyclohexyl]methanamine Chemical compound CN(C)CC1CCC(CN)CC1 FPVLWAAVKMZUJN-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
238000005352 clarification Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004939 coking Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 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
238000001914 filtration Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000005087 leaf formation Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
ZEFFDINQSBHDSD-UHFFFAOYSA-N n',n'-dibutyl-n-ethylbutane-1,4-diamine Chemical compound CCCCN(CCCC)CCCCNCC ZEFFDINQSBHDSD-UHFFFAOYSA-N 0.000 description 1
PWNDYKKNXVKQJO-UHFFFAOYSA-N n',n'-dibutylethane-1,2-diamine Chemical compound CCCCN(CCN)CCCC PWNDYKKNXVKQJO-UHFFFAOYSA-N 0.000 description 1
KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
JSMPEGRPXGJWRD-UHFFFAOYSA-N n',n'-diethyl-n-methylbutane-1,4-diamine Chemical compound CCN(CC)CCCCNC JSMPEGRPXGJWRD-UHFFFAOYSA-N 0.000 description 1
SMJVVYQWUFKTKZ-UHFFFAOYSA-N n',n'-diethyl-n-methylpropane-1,3-diamine Chemical compound CCN(CC)CCCNC SMJVVYQWUFKTKZ-UHFFFAOYSA-N 0.000 description 1
DFTJKKXEHWFFAB-UHFFFAOYSA-N n',n'-diethyl-n-propylpropane-1,3-diamine Chemical compound CCCNCCCN(CC)CC DFTJKKXEHWFFAB-UHFFFAOYSA-N 0.000 description 1
JILXUIANNUALRZ-UHFFFAOYSA-N n',n'-diethylbutane-1,4-diamine Chemical compound CCN(CC)CCCCN JILXUIANNUALRZ-UHFFFAOYSA-N 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
ZGQAVDZROKAVRS-UHFFFAOYSA-N n',n'-dipentylethane-1,2-diamine Chemical compound CCCCCN(CCN)CCCCC ZGQAVDZROKAVRS-UHFFFAOYSA-N 0.000 description 1
ZSGVHFYKNCHHBO-UHFFFAOYSA-N n',n'-dipentylpropane-1,3-diamine Chemical compound CCCCCN(CCCN)CCCCC ZSGVHFYKNCHHBO-UHFFFAOYSA-N 0.000 description 1
GLDVKMPSACNWFV-UHFFFAOYSA-N n',n'-dipropylbutane-1,4-diamine Chemical compound CCCN(CCC)CCCCN GLDVKMPSACNWFV-UHFFFAOYSA-N 0.000 description 1
DMDXQHYISPCTGF-UHFFFAOYSA-N n',n'-dipropylethane-1,2-diamine Chemical compound CCCN(CCC)CCN DMDXQHYISPCTGF-UHFFFAOYSA-N 0.000 description 1
GZUCMODGDIGMBI-UHFFFAOYSA-N n',n'-dipropylpropane-1,3-diamine Chemical compound CCCN(CCC)CCCN GZUCMODGDIGMBI-UHFFFAOYSA-N 0.000 description 1
VBARFWGILFILHY-UHFFFAOYSA-N n'-benzyl-n'-ethylpropane-1,3-diamine Chemical compound NCCCN(CC)CC1=CC=CC=C1 VBARFWGILFILHY-UHFFFAOYSA-N 0.000 description 1
SMIQOXAFNYRXHC-UHFFFAOYSA-N n'-butyl-n'-ethylpropane-1,3-diamine Chemical compound CCCCN(CC)CCCN SMIQOXAFNYRXHC-UHFFFAOYSA-N 0.000 description 1
GOODZUIQBJNDNO-UHFFFAOYSA-N n'-cyclohexyl-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)C1CCCCC1 GOODZUIQBJNDNO-UHFFFAOYSA-N 0.000 description 1
FRVNYRKFLIOCNF-UHFFFAOYSA-N n'-ethyl-n'-methylpropane-1,3-diamine Chemical compound CCN(C)CCCN FRVNYRKFLIOCNF-UHFFFAOYSA-N 0.000 description 1
GHGKUGQRRXYXEJ-UHFFFAOYSA-N n'-ethyl-n'-phenylpropane-1,3-diamine Chemical compound NCCCN(CC)C1=CC=CC=C1 GHGKUGQRRXYXEJ-UHFFFAOYSA-N 0.000 description 1
LSPFZWGMWZRJRO-UHFFFAOYSA-N n,n',n'-triethylbutane-1,4-diamine Chemical compound CCNCCCCN(CC)CC LSPFZWGMWZRJRO-UHFFFAOYSA-N 0.000 description 1
HDCAZTXEZQWTIJ-UHFFFAOYSA-N n,n',n'-triethylethane-1,2-diamine Chemical compound CCNCCN(CC)CC HDCAZTXEZQWTIJ-UHFFFAOYSA-N 0.000 description 1
BIESSHWVDLDLJM-UHFFFAOYSA-N n,n',n'-triethylpropane-1,3-diamine Chemical compound CCNCCCN(CC)CC BIESSHWVDLDLJM-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000001205 polyphosphate Substances 0.000 description 1
235000011176 polyphosphates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 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
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
239000012463 white pigment Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/68—Triazinylamino stilbenes
- 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
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Life Sciences & Earth Sciences (AREA)
Textile Engineering (AREA)
Plural Heterocyclic Compounds (AREA)
Coloring (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Detergent Compositions (AREA)
Paper (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO2955/69A 1968-07-22 1969-07-15 NO125051B (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1095368A CH525991A (de)	1968-07-22	1968-07-22	Verfahren zum optischen Aufhellen von Textilmaterialien, insbesondere aus natürlicher oder regenerierter Cellulose

Publications (1)

Publication Number	Publication Date
NO125051B true NO125051B (xx)	1972-07-10

Family

ID=4368547

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO2955/69A NO125051B (xx)	1968-07-22	1969-07-15

Country Status (11)

Country	Link
US (1)	US3663538A (xx)
AT (1)	AT294751B (xx)
BE (1)	BE736364A (xx)
CH (3)	CH1095368A4 (xx)
DE (1)	DE1930307C3 (xx)
DK (1)	DK137755B (xx)
FR (1)	FR2013466A1 (xx)
GB (1)	GB1274545A (xx)
NL (1)	NL6911208A (xx)
NO (1)	NO125051B (xx)
SE (1)	SE346539B (xx)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4012378A (en) *	1972-02-11	1977-03-15	Imperial Chemical Industries Limited	Reactive dyestuffs
GB1441109A (en) *	1973-01-23	1976-06-30	Ici Ltd	Coating compositions
CH597204A5 (xx) *	1973-02-16	1978-03-31	Sandoz Ag
CH1355873A4 (xx) *	1973-09-21	1977-08-31
DE2915323A1 (de) *	1978-04-26	1979-11-08	Sandoz Ag	Basische bzw. kationische, sulfonsaeuregruppenhaltige monoazo- oder disazoverbindungen
EP0026013B1 (en) *	1979-09-21	1983-09-07	THE PROCTER & GAMBLE COMPANY	Washing and softening compositions and methods for their manufacture
US4478598A (en) *	1981-02-26	1984-10-23	Ciba-Geigy Corporation	Amphoteric styrene derivatives useful as fluorescent brighteners
GB9626851D0 (en) *	1996-12-24	1997-02-12	Ciba Geigy Ag	Compounds
GB9930247D0 (en) *	1999-12-22	2000-02-09	Clariant Int Ltd	Improvements in or relating to organic compounds
GB9930177D0 (en) *	1999-12-22	2000-02-09	Clariant Int Ltd	Improvements in or relating to organic compounds
JP2005529854A (ja) *	2002-03-19	2005-10-06	チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド	両性及び陽イオン性の蛍光増白剤
US7166564B2 (en) *	2003-08-21	2007-01-23	Ciba Specialty Chemicals Corp.	Optical brighteners
JP5698348B2 (ja) *	2010-05-18	2015-04-08	ミリケン・アンド・カンパニーＭｉｌｌｉｋｅｎ＆Ｃｏｍｐａｎｙ	蛍光増白剤およびそれを含む組成物
BR112012029188B1 (pt)	2010-05-18	2020-12-08	Milliken & Company	compostos clareadores óticos e composições compreendendo os mesmos
USD840116S1 (en)	2017-04-19	2019-02-05	Gramercy Products, Inc.	Ball toy

1968
- 1968-07-22 CH CH1095368D patent/CH1095368A4/xx unknown
- 1968-07-22 CH CH1095368A patent/CH525991A/de not_active IP Right Cessation
- 1968-07-22 CH CH631672A patent/CH534170A/de not_active IP Right Cessation
1969
- 1969-06-14 DE DE1930307A patent/DE1930307C3/de not_active Expired
- 1969-07-07 US US839640A patent/US3663538A/en not_active Expired - Lifetime
- 1969-07-15 NO NO2955/69A patent/NO125051B/no unknown
- 1969-07-16 GB GB35888/69A patent/GB1274545A/en not_active Expired
- 1969-07-21 AT AT698769A patent/AT294751B/de not_active IP Right Cessation
- 1969-07-21 DK DK392469AA patent/DK137755B/da unknown
- 1969-07-21 SE SE10243/69A patent/SE346539B/xx unknown
- 1969-07-22 NL NL6911208A patent/NL6911208A/xx unknown
- 1969-07-22 BE BE736364D patent/BE736364A/xx unknown
- 1969-07-22 FR FR6924879A patent/FR2013466A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
CH534170A (de)	1973-02-28
CH525991A (de)	1972-03-30
AT294751B (de)	1971-12-10
FR2013466A1 (xx)	1970-04-03
DK137755B (da)	1978-05-01
US3663538A (en)	1972-05-16
DK137755C (xx)	1978-10-09
DE1930307B2 (de)	1978-06-15
NL6911208A (xx)	1970-01-26
SE346539B (xx)	1972-07-10
DE1930307C3 (de)	1979-03-15
BE736364A (xx)	1970-01-22
CH1095368A4 (xx)	1972-03-30
GB1274545A (en)	1972-05-17
DE1930307A1 (de)	1970-02-12

Publication	Publication Date	Title
NO125051B (xx)	1972-07-10
CA2610518C (en)	2013-09-10	Storage stable solutions of optical brighteners
US4360679A (en)	1982-11-23	Benzofuranyl-benzimidazoles
JPH0153301B2 (xx)	1989-11-13
JPS6289665A (ja)	1987-04-24	蛍光の消光方法および新規なカチオン系ナフタレン−ペリ−ジカルボン酸イミド誘導体類
RU2505535C2 (ru)	2014-01-27	Стабильные при хранении растворы оптических отбеливателей
KR20140048126A (ko)	2014-04-23	신규한 비스－（트리아지닐아미노）－스틸벤 유도체들
US4025507A (en)	1977-05-24	Bis-(triazinylamino) stilbene compounds
JP3902672B2 (ja)	2007-04-11	スルホン酸基を含む塩基性ジスアゾ化合物
DE2406883A1 (de)	1974-08-22	Stilbenverbindungen
JP2638621B2 (ja)	1997-08-06	カチオンスチルベンジスアゾ染料
NO145886B (no)	1982-03-08	Anvendelse av vannloeselige ammoniumsalter for aa oppheve dir en av optiske hvithetsmidler frembrakte lyshet f.eks. i pap
JPH0471948B2 (xx)	1992-11-17
US4081239A (en)	1978-03-28	Storage stable concentrated aqueous solutions of aminomethylated phthalocyanines
JPS6334189B2 (xx)	1988-07-08
EP1177180A1 (de)	2002-02-06	Stilbenaufheller
US4845209A (en)	1989-07-04	Cationic phthalocyanine compounds
RU2556635C2 (ru)	2015-07-10	Концентрированные стабильные в хранении водные растворы оптических отбеливателей
US4814453A (en)	1989-03-21	Naphthalimides containing sulfuric acid ester groups, a process for their preparation and their use
JPS59136352A (ja)	1984-08-04	フタロシアニン化合物
JPS644544B2 (xx)	1989-01-26
JPH0414142B2 (xx)	1992-03-11
ITRM940707A1 (it)	1996-05-03	"ftalocianine d'alluminio cationiche, loro preparazione e loro impiego in procedimenti di tintura e di stampa"
JPS62167361A (ja)	1987-07-23	カチオン化合物及びそれを用いる基材の染色法
JPH09119069A (ja)	1997-05-06	グアニジン塩またはエチレンジアミン塩で難燃化処理された、変色防止剤を含有するセルロース材料