DE2250133A1 - Quarternaere ammoniumchloride - Google Patents
Quarternaere ammoniumchlorideInfo
- Publication number
- DE2250133A1 DE2250133A1 DE2250133A DE2250133A DE2250133A1 DE 2250133 A1 DE2250133 A1 DE 2250133A1 DE 2250133 A DE2250133 A DE 2250133A DE 2250133 A DE2250133 A DE 2250133A DE 2250133 A1 DE2250133 A1 DE 2250133A1
- Authority
- DE
- Germany
- Prior art keywords
- cii
- general formula
- radical
- mol
- compounds
- 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.)
- Pending
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 17
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000981 basic dye Substances 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000975 dye Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 239000012230 colorless oil Substances 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000033228 biological regulation Effects 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 244000060011 Cocos nucifera Species 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 4
- 229950010007 dimantine Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- -1 ketones and hydrocarbons Chemical class 0.000 description 4
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 4
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 206010037867 Rash macular Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical group ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VBCJJAZGEJSVTL-UHFFFAOYSA-N (Z)-18-methylnonadec-9-en-1-amine Chemical compound CC(CCCCCCCC=C/CCCCCCCCN)C VBCJJAZGEJSVTL-UHFFFAOYSA-N 0.000 description 1
- GNPSDJOWGWWXSS-UHFFFAOYSA-M 1-benzylpyridin-1-ium;chloride Chemical compound [Cl-].C=1C=CC=C[N+]=1CC1=CC=CC=C1 GNPSDJOWGWWXSS-UHFFFAOYSA-M 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- ZMWAXVAETNTVAT-UHFFFAOYSA-N 7-n,8-n,5-triphenylphenazin-5-ium-2,3,7,8-tetramine;chloride Chemical compound [Cl-].C=1C=CC=CC=1NC=1C=C2[N+](C=3C=CC=CC=3)=C3C=C(N)C(N)=CC3=NC2=CC=1NC1=CC=CC=C1 ZMWAXVAETNTVAT-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
- ICZKASVWFUJTEI-UHFFFAOYSA-N n,n-dimethyldocosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN(C)C ICZKASVWFUJTEI-UHFFFAOYSA-N 0.000 description 1
- AYNZRGVSQNDHIX-UHFFFAOYSA-N n,n-dimethylicosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN(C)C AYNZRGVSQNDHIX-UHFFFAOYSA-N 0.000 description 1
- SFBHPFQSSDCYSL-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)C SFBHPFQSSDCYSL-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229940106026 phenoxyisopropanol Drugs 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine group Chemical class C(CCC)N(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/70—Material containing nitrile groups
- D06P3/76—Material containing nitrile groups using basic dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2250133A DE2250133A1 (de) | 1972-10-13 | 1972-10-13 | Quarternaere ammoniumchloride |
| US399699A US3919319A (en) | 1972-10-13 | 1973-09-24 | Quaternary ammonium chlorides |
| NL7313735A NL7313735A (US20050192411A1-20050901-C00001.png) | 1972-10-13 | 1973-10-05 | |
| CA182,904A CA996954A (en) | 1972-10-13 | 1973-10-09 | Quaternary ammonium chlorides |
| JP48113355A JPS4972479A (US20050192411A1-20050901-C00001.png) | 1972-10-13 | 1973-10-11 | |
| CH939175A CH570362A5 (US20050192411A1-20050901-C00001.png) | 1972-10-13 | 1973-10-12 | |
| BE136666A BE806048A (fr) | 1972-10-13 | 1973-10-12 | Chlorures d'ammonium quaternaire utilisables comme agents d'unisson |
| IT30079/73A IT995836B (it) | 1972-10-13 | 1973-10-12 | Cloruri di ammonio quaternari |
| CH1454773A CH576550B5 (US20050192411A1-20050901-C00001.png) | 1972-10-13 | 1973-10-12 | |
| GB4780173A GB1402478A (en) | 1972-10-13 | 1973-10-12 | Quaternary ammonium chlorides |
| FR7336525A FR2202879B1 (US20050192411A1-20050901-C00001.png) | 1972-10-13 | 1973-10-12 | |
| CH1454773D CH1454773A4 (US20050192411A1-20050901-C00001.png) | 1972-10-13 | 1973-10-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2250133A DE2250133A1 (de) | 1972-10-13 | 1972-10-13 | Quarternaere ammoniumchloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2250133A1 true DE2250133A1 (de) | 1974-04-25 |
Family
ID=5858881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2250133A Pending DE2250133A1 (de) | 1972-10-13 | 1972-10-13 | Quarternaere ammoniumchloride |
Country Status (10)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0090117A1 (en) * | 1981-12-09 | 1983-10-05 | Imperial Chemical Industries Plc | Alkoxylated quaternary ammonium salts |
| EP0182669A1 (en) * | 1984-11-21 | 1986-05-28 | Atlantic Richfield Company | Quaternary Ammonium compounds |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4074970A (en) * | 1976-11-15 | 1978-02-21 | Sybron Corporation | Dyeing of synthetic fibers with cationic dyes in the presence of cationic assistants containing hydroxyl and cyclic moieties |
| SE443138B (sv) * | 1979-12-10 | 1986-02-17 | Berol Kemi Ab | Ytaktiv kvarter ammoniumforening samt anvendning av denna vid behandling av textil- och cellulosamaterial |
| EP0050164B1 (en) * | 1980-10-20 | 1985-10-16 | Board Of Control Of Michigan Technological University | Method of manufacturing structural members of composit wood material |
| GB2116966B (en) * | 1982-02-26 | 1986-01-15 | British Petroleum Co Plc | N-oxyalkylated aqueous compositions of quaternary ammenium salt surfactants |
| US4694104A (en) * | 1982-08-09 | 1987-09-15 | Gaf Corporation | Phase transfer catalysts |
| WO2004090221A1 (ja) * | 2003-04-01 | 2004-10-21 | Matsumoto Yushi-Seiyaku Co., Ltd. | 透水性付与剤およびその付与剤が付着した繊維 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR819000A (fr) * | 1936-04-11 | 1937-10-07 | Ig Farbenindustrie Ag | Procédé pour préparer des produits de condensation renfermant de l'azote |
| US2581336A (en) * | 1944-11-24 | 1952-01-08 | Ciba Pharm Prod Inc | Phenoxyethyl-dimethyl-dodecyl-ammonium halides |
| US2775604A (en) * | 1953-02-09 | 1956-12-25 | Atlas Powder Co | Quaternary ammonium halides |
| US3318954A (en) * | 1964-04-24 | 1967-05-09 | Procter & Gamble | Process for the production of quaternary ammonium compounds |
| US3326927A (en) * | 1964-05-18 | 1967-06-20 | Dow Chemical Co | Certain pyridinium and quaternary ammonium derivatives of phenolic-polyoxy alkylene compounds and a method for their preparation |
-
1972
- 1972-10-13 DE DE2250133A patent/DE2250133A1/de active Pending
-
1973
- 1973-09-24 US US399699A patent/US3919319A/en not_active Expired - Lifetime
- 1973-10-05 NL NL7313735A patent/NL7313735A/xx unknown
- 1973-10-09 CA CA182,904A patent/CA996954A/en not_active Expired
- 1973-10-11 JP JP48113355A patent/JPS4972479A/ja active Pending
- 1973-10-12 GB GB4780173A patent/GB1402478A/en not_active Expired
- 1973-10-12 FR FR7336525A patent/FR2202879B1/fr not_active Expired
- 1973-10-12 CH CH939175A patent/CH570362A5/xx not_active IP Right Cessation
- 1973-10-12 CH CH1454773D patent/CH1454773A4/xx unknown
- 1973-10-12 BE BE136666A patent/BE806048A/xx unknown
- 1973-10-12 IT IT30079/73A patent/IT995836B/it active
- 1973-10-12 CH CH1454773A patent/CH576550B5/xx not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0090117A1 (en) * | 1981-12-09 | 1983-10-05 | Imperial Chemical Industries Plc | Alkoxylated quaternary ammonium salts |
| EP0182669A1 (en) * | 1984-11-21 | 1986-05-28 | Atlantic Richfield Company | Quaternary Ammonium compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2202879B1 (US20050192411A1-20050901-C00001.png) | 1977-03-11 |
| CH576550B5 (US20050192411A1-20050901-C00001.png) | 1976-06-15 |
| CH570362A5 (US20050192411A1-20050901-C00001.png) | 1975-12-15 |
| GB1402478A (en) | 1975-08-06 |
| US3919319A (en) | 1975-11-11 |
| NL7313735A (US20050192411A1-20050901-C00001.png) | 1974-04-16 |
| BE806048A (fr) | 1974-04-12 |
| CA996954A (en) | 1976-09-14 |
| IT995836B (it) | 1975-11-20 |
| CH1454773A4 (US20050192411A1-20050901-C00001.png) | 1975-10-15 |
| FR2202879A1 (US20050192411A1-20050901-C00001.png) | 1974-05-10 |
| JPS4972479A (US20050192411A1-20050901-C00001.png) | 1974-07-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2121013B2 (de) | Acyloxyalkylammoniumsalze, deren Herstellung und Verwendung als Färbehilfsmittel | |
| DE2250133A1 (de) | Quarternaere ammoniumchloride | |
| DE2413299C3 (de) | Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitrils | |
| DE2050725C3 (de) | Aufhellungsmittel | |
| DE2260703A1 (de) | Verfahren zum faerben von textilfasermaterial aus polyacrylnitril | |
| DE1906709A1 (de) | Basische Azofarbstoffe,ihre Herstellung und Verwendung | |
| DE2458347A1 (de) | Verfahren zur herstellung von basischen oxazinfarbstoffen | |
| DE2631166C2 (de) | Verfahren zur Herstellung von Oxazinfarbstoffen | |
| DE1569748C3 (de) | Sulfonsäure- und carbonsäuregruppenfreie Aminodiphenyl-indolyl-methanfarbstoffe, deren Herstellung und Verwendung | |
| EP0073996A1 (de) | Aufhellersalze und deren Verwendung für das Nassspinnen von Acrylfasern | |
| DE2741340A1 (de) | Quaternaere aminogruppen enthaltende polyaether und verfahren zu ihrer herstellung | |
| CH457662A (de) | Verfahren zur Herstellung basischer Farbstoffe | |
| DE1472890C3 (de) | Lichthofschutzschicht | |
| DE2805239A1 (de) | Quaternaere aminogruppen enthaltende polyaether und verfahren zu ihrer herstellung | |
| DE633081C (de) | Verfahren zur Verbesserung der Wasserechtheit von Faerbungen auf Textilstoffen | |
| DE2343418C2 (de) | Egalisiermittel für Säurefarbstoffe | |
| DE2061760B2 (de) | Konzentrierte wäßrige Lösungen metallfreier anionischer Farbstoffe | |
| DE2906132A1 (de) | Verfahren zur herstellung kationischer anthrachinon-farbstoffe | |
| DE1745622C2 (de) | 1,4-Bis-benzoxazolyl-naphthalin-dicarbonsäureester, Verfahren zu deren Herstellung und deren Verwendung als optische Aufheller | |
| DE811906C (de) | Verfahren zur Herstellung von gefaerbten photographischen Schichten | |
| DE2030028B2 (de) | Basische Oxazinfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| CH427364A (de) | Gerät zur graphischen Darstellung von Sachverhalten, insbesondere Planungsgerät, und Verwendung desselben | |
| DE1143025B (de) | Verfahren zum Stabilisieren von Polyoxymethylenen | |
| DE2449206A1 (de) | Verfahren zur herstellung konzentrierter loesungen von harnstoffverbindungen | |
| DE1936460A1 (de) | Stabile,konzentrierte waesserige Loesungen von basischen Farbstoffen |