DE60215767T2 - Acetoxymethylsulfon oder vinylsulfon enthaltende reaktive dispersionsfarbstoffe und verfahren zu ihrer herstellung - Google Patents
Acetoxymethylsulfon oder vinylsulfon enthaltende reaktive dispersionsfarbstoffe und verfahren zu ihrer herstellung Download PDFInfo
- Publication number
- DE60215767T2 DE60215767T2 DE60215767T DE60215767T DE60215767T2 DE 60215767 T2 DE60215767 T2 DE 60215767T2 DE 60215767 T DE60215767 T DE 60215767T DE 60215767 T DE60215767 T DE 60215767T DE 60215767 T2 DE60215767 T2 DE 60215767T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- group
- alkyl
- alkoxy
- 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.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 11
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 title description 6
- UFSKCTMESWSZJP-UHFFFAOYSA-N acetyloxymethylsulfonylmethyl acetate Chemical compound CC(=O)OCS(=O)(=O)COC(C)=O UFSKCTMESWSZJP-UHFFFAOYSA-N 0.000 title 1
- 239000006185 dispersion Substances 0.000 title 1
- 239000000986 disperse dye Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 238000005859 coupling reaction Methods 0.000 claims description 17
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 17
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
- QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical compound OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 230000000397 acetylating effect Effects 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- 239000000975 dye Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- ZNEZVLKEOCTFHJ-UHFFFAOYSA-N 2-(2-acetyloxyethylsulfonyl)ethyl acetate Chemical compound CC(=O)OCCS(=O)(=O)CCOC(C)=O ZNEZVLKEOCTFHJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000006193 diazotization reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- MAFGFYFHPXKEJJ-UHFFFAOYSA-N [2-[2-acetyloxy-2-(4-aminophenyl)ethyl]sulfonyl-1-(4-aminophenyl)ethyl] acetate Chemical compound C=1C=C(N)C=CC=1C(OC(=O)C)CS(=O)(=O)CC(OC(C)=O)C1=CC=C(N)C=C1 MAFGFYFHPXKEJJ-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000000985 reactive dye Substances 0.000 description 9
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- -1 4-aminophenyl-β-acetoxyethylsulfone compound Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- 0 CC1C=C(*)C(*)=C[C@@]1N=N** Chemical compound CC1C=C(*)C(*)=C[C@@]1N=N** 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 239000000434 metal complex dye Substances 0.000 description 4
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 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 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 3
- 239000000980 acid dye Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- XBPVHXVJJROVKU-UHFFFAOYSA-N 1,4-dimethyl-2,6-dioxo-3h-pyridine-3-carbonitrile Chemical compound CN1C(=O)C=C(C)C(C#N)C1=O XBPVHXVJJROVKU-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- QJQOQCWGYQJWBV-UHFFFAOYSA-N n-[4-[2-[2-(4-acetamidophenyl)-2-hydroxyethyl]sulfonyl-1-hydroxyethyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(O)CS(=O)(=O)CC(O)C1=CC=C(NC(C)=O)C=C1 QJQOQCWGYQJWBV-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/51—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Coloring (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2001-0002733A KR100385299B1 (ko) | 2001-01-17 | 2001-01-17 | 아세톡시에틸설폰 반응기를 갖는 분산 반응성 염료 및이의 제조방법 |
| KR2001002733 | 2001-01-17 | ||
| KR2001003009 | 2001-01-18 | ||
| KR10-2001-0003009A KR100385300B1 (ko) | 2001-01-18 | 2001-01-18 | 벤조티아졸계 분산 반응성 염료 및 이의 제조방법 |
| KR2001004026 | 2001-01-29 | ||
| KR10-2001-0004026A KR100411189B1 (ko) | 2001-01-29 | 2001-01-29 | 비닐설폰 반응기를 갖는 분산 반응성 염료 |
| PCT/KR2002/000069 WO2002057370A1 (en) | 2001-01-17 | 2002-01-16 | Dispers-reactive dyes containing acetoxymethylsulfone or vinylsulfone and their process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60215767D1 DE60215767D1 (de) | 2006-12-14 |
| DE60215767T2 true DE60215767T2 (de) | 2007-08-30 |
Family
ID=27350396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60215767T Expired - Fee Related DE60215767T2 (de) | 2001-01-17 | 2002-01-16 | Acetoxymethylsulfon oder vinylsulfon enthaltende reaktive dispersionsfarbstoffe und verfahren zu ihrer herstellung |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6884876B2 (enExample) |
| EP (1) | EP1352032B1 (enExample) |
| JP (1) | JP2004525208A (enExample) |
| DE (1) | DE60215767T2 (enExample) |
| WO (1) | WO2002057370A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA100527C2 (en) | 2007-10-10 | 2013-01-10 | Астразенека Аб | Benzothiazoles as ghrelin receptor modulators |
| CN106497139B (zh) * | 2016-08-31 | 2018-10-23 | 沈阳化工研究院有限公司 | 一种超临界co2用乙烯砜型活性分散染料及其制备方法和应用 |
| KR102260181B1 (ko) * | 2019-11-20 | 2021-06-03 | 한국화학연구원 | 초임계 유체염색용 아조계 반응성 분산염료 및 이를 이용한 초임계 유체 염색 방법 |
| KR102282524B1 (ko) * | 2019-11-20 | 2021-07-27 | 한국화학연구원 | 초임계 유체염색용 아조계 반응성 분산염료 및 이를 이용한 초임계 유체 염색 방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2106648C3 (de) * | 1971-02-12 | 1980-06-26 | Hoechst Ag, 6000 Frankfurt | Wasserlösliche Azo- und Anthrachinonfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Farben oder Bedrucken von Fasermaterialien aus Cellulose 2,5-acetat, Cellulosetriacetat, Polyamiden, Polyurethanen, Polyestern, Cellulose, Wolle oder Seide |
| US4134887A (en) * | 1973-10-17 | 1979-01-16 | Hoechst Aktiengesellschaft | Phenyl-azo-phenyl dyestuffs |
| IT1193906B (it) * | 1980-01-31 | 1988-08-31 | Acna | Coloranti dispersi-reattivi adatti alla tintura ed alla stampa delle fibre miste poliestere-cellulosa |
| DE3113001A1 (de) * | 1980-11-06 | 1982-06-09 | Hoechst Ag, 6000 Frankfurt | Wasserloesliche monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| EP0109029B1 (de) * | 1982-11-13 | 1986-09-24 | Hoechst Aktiengesellschaft | Verfahren zum Färben von Textilgut aus modifizierten Polyesterfasern |
| US4614521A (en) * | 1984-06-06 | 1986-09-30 | Mitsubishi Chemical Industries Limited | Transfer recording method using reactive sublimable dyes |
| DE3424320A1 (de) * | 1984-07-02 | 1986-01-23 | Sandoz-Patent-GmbH, 7850 Lörrach | Wasserloesliche basische farbstoffe, ihre herstellung und verwendung |
-
2002
- 2002-01-16 DE DE60215767T patent/DE60215767T2/de not_active Expired - Fee Related
- 2002-01-16 EP EP02715901A patent/EP1352032B1/en not_active Expired - Lifetime
- 2002-01-16 JP JP2002558434A patent/JP2004525208A/ja active Pending
- 2002-01-16 WO PCT/KR2002/000069 patent/WO2002057370A1/en not_active Ceased
- 2002-01-16 US US10/466,356 patent/US6884876B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20040077846A1 (en) | 2004-04-22 |
| WO2002057370A1 (en) | 2002-07-25 |
| EP1352032B1 (en) | 2006-11-02 |
| US6884876B2 (en) | 2005-04-26 |
| DE60215767D1 (de) | 2006-12-14 |
| JP2004525208A (ja) | 2004-08-19 |
| EP1352032A1 (en) | 2003-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |