DE3009522C2 - Verwendung von reaktiven Azofarbstoffen zur Herstellung von antimikrobiellen Eiweiß- und Zellulosefaserstoffen - Google Patents
Verwendung von reaktiven Azofarbstoffen zur Herstellung von antimikrobiellen Eiweiß- und ZellulosefaserstoffenInfo
- Publication number
- DE3009522C2 DE3009522C2 DE3009522A DE3009522A DE3009522C2 DE 3009522 C2 DE3009522 C2 DE 3009522C2 DE 3009522 A DE3009522 A DE 3009522A DE 3009522 A DE3009522 A DE 3009522A DE 3009522 C2 DE3009522 C2 DE 3009522C2
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- azo dye
- azo dyes
- fabric
- cellulose fibers
- 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
Links
- 239000000987 azo dye Substances 0.000 title claims description 35
- 230000000845 anti-microbial effect Effects 0.000 title description 15
- 102000004169 proteins and genes Human genes 0.000 title description 10
- 108090000623 proteins and genes Proteins 0.000 title description 10
- 229920003043 Cellulose fiber Polymers 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000004744 fabric Substances 0.000 description 21
- 239000000975 dye Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- 238000004043 dyeing Methods 0.000 description 10
- 239000000835 fiber Substances 0.000 description 10
- 239000002657 fibrous material Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- 239000004753 textile Substances 0.000 description 9
- 230000002421 anti-septic effect Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- 229940064004 antiseptic throat preparations Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 150000008049 diazo compounds Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 241000233866 Fungi Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 3
- 229950000975 salicylanilide Drugs 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- OHTLMOZFNWRXRO-UHFFFAOYSA-N [Na].N1=C(C=2C=C(N)C(=CC=2)S(O)(=O)=O)N=C(Cl)N(N)C1OC1=CC(Cl)=C(Cl)C=C1Cl Chemical compound [Na].N1=C(C=2C=C(N)C(=CC=2)S(O)(=O)=O)N=C(Cl)N(N)C1OC1=CC(Cl)=C(Cl)C=C1Cl OHTLMOZFNWRXRO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006065 biodegradation reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003344 environmental pollutant Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 231100000719 pollutant Toxicity 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- IJGSULQFKYOYEU-UHFFFAOYSA-N 2,3,4-trifluorophenol Chemical group OC1=CC=C(F)C(F)=C1F IJGSULQFKYOYEU-UHFFFAOYSA-N 0.000 description 1
- WWXJTDBGKAKNCW-UHFFFAOYSA-N 3-amino-7-(4-aminobenzoyl)-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(C(O)=C(N)C(=C2)S(O)(=O)=O)C2=C1 WWXJTDBGKAKNCW-UHFFFAOYSA-N 0.000 description 1
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical class ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 1
- 241000228197 Aspergillus flavus Species 0.000 description 1
- 241000203233 Aspergillus versicolor Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 241001236817 Paecilomyces <Clavicipitaceae> Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241001279364 Stachybotrys chartarum Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241001104043 Syringa Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZVAKTWSQIIRIIH-UHFFFAOYSA-N [K].[I] Chemical compound [K].[I] ZVAKTWSQIIRIIH-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
- 229960004068 hexachlorophene Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- PQMSFAORUFMASU-UHFFFAOYSA-M sulfacetamide sodium anhydrous Chemical compound [Na+].CC(=O)[N-]S(=O)(=O)C1=CC=C(N)C=C1 PQMSFAORUFMASU-UHFFFAOYSA-M 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/062—Phenols
- C09B31/065—Phenols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
-
- 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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
-
- 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)
- Coloring (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU792729601A SU910703A1 (ru) | 1979-03-13 | 1979-03-13 | Активные азокрасители с фунгицидными свойствами |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3009522A1 DE3009522A1 (de) | 1980-09-25 |
| DE3009522C2 true DE3009522C2 (de) | 1984-06-07 |
Family
ID=20812221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3009522A Expired DE3009522C2 (de) | 1979-03-13 | 1980-03-12 | Verwendung von reaktiven Azofarbstoffen zur Herstellung von antimikrobiellen Eiweiß- und Zellulosefaserstoffen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4407748A (OSRAM) |
| JP (2) | JPS5925826B2 (OSRAM) |
| CH (1) | CH651447A5 (OSRAM) |
| DE (1) | DE3009522C2 (OSRAM) |
| FR (1) | FR2451388A1 (OSRAM) |
| GB (1) | GB2046288B (OSRAM) |
| SU (1) | SU910703A1 (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3100978A1 (de) * | 1981-01-15 | 1982-08-05 | Bayer Ag, 5090 Leverkusen | Naphtholsulfonsaeurebetaine, ihre herstellung und verwendung als kupplungskomponenten |
| DE3432891A1 (de) * | 1984-09-07 | 1986-03-20 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 3-(acyl)amino-4-alkoxyphenyl-ss-hydroxyethylsulfon(-schwefelsaeureestern) |
| US5175262A (en) * | 1989-03-13 | 1992-12-29 | Basf Aktiengesellschaft | Doubled reactive dyes |
| US5159075A (en) * | 1990-06-07 | 1992-10-27 | General Electric Company | Substituted chlorotriazines useful for reactive capping of polyphenylene ethers |
| US5142049A (en) * | 1990-08-15 | 1992-08-25 | General Electric Company | Ortho ester-substituted chlorotriazines as capping agents for polyphenylene ethers |
| US6436419B1 (en) * | 1998-09-11 | 2002-08-20 | The Regents Of The University Of California | Antimicrobial treatment of polymers |
| US6962608B1 (en) | 2002-10-01 | 2005-11-08 | The Regents Of The University Of California | Regenerable antimicrobial polymers and fibers with oxygen bleaches |
| US20060242770A1 (en) * | 2003-04-21 | 2006-11-02 | Peter Albersheim | Xyloglucan conjugates useful for modifying cellulosic textiles |
| KR100821895B1 (ko) | 2005-02-23 | 2008-04-16 | 주식회사 코오롱 | 은 함유 항균 산성 염료와 그의 제조 방법 및 그를 이용한항균 섬유 |
| US10836726B2 (en) * | 2016-10-16 | 2020-11-17 | Ada Foundation | AZO-quaternary pyridinium salts with acid-enhanced antibacterial efficacy, methods of use, methods of synthesis, and uses thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1499788A (fr) * | 1966-11-16 | 1967-10-27 | Mo Textilny I | Procédé de préparation de produits doués de propriétés antimicrobiennes à partir de fibres ou pellicules |
| CH501042A (de) * | 1967-09-13 | 1970-12-31 | Ciba Geigy Ag | Verfahren zur Herstellung von faserreativen Disazofarbstoffen |
| SU401169A1 (ru) * | 1971-07-23 | 1976-01-25 | Московский Ордена Трудового Красного Знамени Текстильный Институт | Способ получени антимикробных азокрасителей |
| DE2236107C2 (de) * | 1972-07-22 | 1982-09-23 | Hoechst Ag, 6000 Frankfurt | Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| SU455610A1 (ru) * | 1972-12-22 | 1978-06-30 | Научно-Исследовательский Институт По Переработке Искусственных И Синтетических Волокон | Способ получени бактерицидного активного красител |
| DE2644442C2 (de) * | 1976-02-02 | 1984-02-16 | Institut Chimii Akademii Nauk Tadžikskoj SSR, Dušanbe | Verfahren zur Herstellung eines bakteriziden Monochlortriazinfarbstoffes |
-
1979
- 1979-03-13 SU SU792729601A patent/SU910703A1/ru active
-
1980
- 1980-03-12 CH CH1942/80A patent/CH651447A5/de not_active IP Right Cessation
- 1980-03-12 DE DE3009522A patent/DE3009522C2/de not_active Expired
- 1980-03-13 JP JP55030954A patent/JPS5925826B2/ja not_active Expired
- 1980-03-13 US US06/129,903 patent/US4407748A/en not_active Expired - Lifetime
- 1980-03-13 GB GB8008525A patent/GB2046288B/en not_active Expired
- 1980-03-13 FR FR8005604A patent/FR2451388A1/fr active Granted
-
1982
- 1982-04-20 JP JP57064879A patent/JPS6029748B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57185353A (en) | 1982-11-15 |
| GB2046288B (en) | 1983-04-20 |
| US4407748A (en) | 1983-10-04 |
| JPS55144055A (en) | 1980-11-10 |
| FR2451388A1 (fr) | 1980-10-10 |
| FR2451388B1 (OSRAM) | 1984-10-26 |
| DE3009522A1 (de) | 1980-09-25 |
| SU910703A1 (ru) | 1982-03-07 |
| JPS6029748B2 (ja) | 1985-07-12 |
| CH651447A5 (de) | 1985-09-30 |
| JPS5925826B2 (ja) | 1984-06-21 |
| GB2046288A (en) | 1980-11-12 |
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