DE2061357A1 - Verfahren zur Erzeugung von unlöslichen Azofarbstoffen auf Cellulosefasern - Google Patents
Verfahren zur Erzeugung von unlöslichen Azofarbstoffen auf CellulosefasernInfo
- Publication number
- DE2061357A1 DE2061357A1 DE19702061357 DE2061357A DE2061357A1 DE 2061357 A1 DE2061357 A1 DE 2061357A1 DE 19702061357 DE19702061357 DE 19702061357 DE 2061357 A DE2061357 A DE 2061357A DE 2061357 A1 DE2061357 A1 DE 2061357A1
- Authority
- DE
- Germany
- Prior art keywords
- coupling
- process according
- solvent
- acid
- amino
- 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
- 238000000034 method Methods 0.000 title claims description 26
- 229920003043 Cellulose fiber Polymers 0.000 title claims description 8
- 239000000987 azo dye Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 230000008878 coupling Effects 0.000 claims description 21
- 238000010168 coupling process Methods 0.000 claims description 21
- 238000005859 coupling reaction Methods 0.000 claims description 21
- -1 diazoamino compound Chemical class 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000004043 dyeing Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000001989 diazonium salts Chemical class 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 150000003142 primary aromatic amines Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- 150000003931 anilides Chemical class 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 229950011008 tetrachloroethylene Drugs 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- NBJZEUQTGLSUOB-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(N=C=O)=CC=C1Cl NBJZEUQTGLSUOB-UHFFFAOYSA-N 0.000 description 1
- REELSMJRRUUNKR-UHFFFAOYSA-N 2-(methylamino)acetic acid;sodium Chemical compound [Na].CNCC(O)=O REELSMJRRUUNKR-UHFFFAOYSA-N 0.000 description 1
- HQOBDLCAOWRBOU-UHFFFAOYSA-N 2-hydroxy-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC=C2NC2=C1C=CC(O)=C2C(=O)O HQOBDLCAOWRBOU-UHFFFAOYSA-N 0.000 description 1
- KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical class NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- FBLAHUMENIHUGG-UHFFFAOYSA-N 3-hydroxy-n-(2-methylphenyl)naphthalene-2-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O FBLAHUMENIHUGG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XWPDPFLBSAPRCO-UHFFFAOYSA-N 4-(chloromethoxy)aniline Chemical class NC1=CC=C(OCCl)C=C1 XWPDPFLBSAPRCO-UHFFFAOYSA-N 0.000 description 1
- PZDXDOLQKQBWJV-UHFFFAOYSA-N 4-(nitromethoxy)aniline Chemical class NC1=CC=C(OC[N+]([O-])=O)C=C1 PZDXDOLQKQBWJV-UHFFFAOYSA-N 0.000 description 1
- RXJCXGJKJZARAW-UHFFFAOYSA-N 4-chloro-1,2-dimethoxybenzene Chemical compound COC1=CC=C(Cl)C=C1OC RXJCXGJKJZARAW-UHFFFAOYSA-N 0.000 description 1
- RBLUJIWKMSZIMK-UHFFFAOYSA-N 4-n-(4-methoxyphenyl)benzene-1,4-diamine Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(N)C=C1 RBLUJIWKMSZIMK-UHFFFAOYSA-N 0.000 description 1
- 241001040682 Anaides Species 0.000 description 1
- CXFUQUORVTVNTE-UHFFFAOYSA-N C1C(OC)=C(N)C=CC1(OC)NC(=O)C1=CC=CC=C1 Chemical compound C1C(OC)=C(N)C=CC1(OC)NC(=O)C1=CC=CC=C1 CXFUQUORVTVNTE-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000002223 garnet Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical class N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QFCSRGLEMDRBMN-UHFFFAOYSA-N n-(2-methylphenyl)nitramide Chemical class CC1=CC=CC=C1N[N+]([O-])=O QFCSRGLEMDRBMN-UHFFFAOYSA-N 0.000 description 1
- CLXWSQCXMNVBQP-UHFFFAOYSA-N n-(3,4-diethoxyphenyl)benzamide Chemical compound C1=C(OCC)C(OCC)=CC=C1NC(=O)C1=CC=CC=C1 CLXWSQCXMNVBQP-UHFFFAOYSA-N 0.000 description 1
- PPLNRTPNYCWODC-UHFFFAOYSA-N n-(4-chlorophenyl)-2-hydroxy-9h-carbazole-3-carboxamide Chemical compound OC1=CC=2NC3=CC=CC=C3C=2C=C1C(=O)NC1=CC=C(Cl)C=C1 PPLNRTPNYCWODC-UHFFFAOYSA-N 0.000 description 1
- SHLTXWFNRJQZTQ-UHFFFAOYSA-N n-chloro-2-methylaniline Chemical class CC1=CC=CC=C1NCl SHLTXWFNRJQZTQ-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000035899 viability Effects 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
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/68—Preparing azo dyes on the material
-
- 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
- D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/92—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
- D06P1/922—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 dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702061357 DE2061357A1 (de) | 1970-12-12 | 1970-12-12 | Verfahren zur Erzeugung von unlöslichen Azofarbstoffen auf Cellulosefasern |
| CH1787971A CH554971A (enrdf_load_stackoverflow) | 1970-12-12 | 1971-12-08 | |
| CH1787971D CH1787971A4 (enrdf_load_stackoverflow) | 1970-12-12 | 1971-12-08 | |
| GB5746671A GB1377210A (en) | 1970-12-12 | 1971-12-10 | Process for dyeing cellulose fibres with water-insoluble azo dye stuffs |
| US00206904A US3787179A (en) | 1970-12-12 | 1971-12-10 | Process for the manufacture of insoluble azo dyestuffs on cellulose fibers |
| BE776540A BE776540A (fr) | 1970-12-12 | 1971-12-10 | Procede d'obtention de colorants azoiques insolubles sur des fibres cellulosiques |
| FR7144672A FR2118054A1 (enrdf_load_stackoverflow) | 1970-12-12 | 1971-12-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702061357 DE2061357A1 (de) | 1970-12-12 | 1970-12-12 | Verfahren zur Erzeugung von unlöslichen Azofarbstoffen auf Cellulosefasern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2061357A1 true DE2061357A1 (de) | 1972-06-15 |
Family
ID=5790855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702061357 Pending DE2061357A1 (de) | 1970-12-12 | 1970-12-12 | Verfahren zur Erzeugung von unlöslichen Azofarbstoffen auf Cellulosefasern |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3787179A (enrdf_load_stackoverflow) |
| BE (1) | BE776540A (enrdf_load_stackoverflow) |
| CH (2) | CH1787971A4 (enrdf_load_stackoverflow) |
| DE (1) | DE2061357A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2118054A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1377210A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2847532A1 (de) * | 1978-11-02 | 1980-05-08 | Bayer Ag | Verfahren zur herstellung von azofarbstoffen |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2557554C3 (de) * | 1975-12-20 | 1979-05-23 | Hoechst Ag, 6000 Frankfurt | Verfahren zum Drucken mit Entwicklungsfarbstoffen |
| NL7512060A (nl) * | 1974-10-19 | 1976-04-21 | Hoechst Ag | Werkwijze voor het drukken met ontwikkelkleur- stoffen. |
| DE2740587C2 (de) * | 1977-09-09 | 1979-08-16 | Hoechst Ag, 6000 Frankfurt | Verfahren zum Bedrucken von textlien Mischgeweben aus Polyester- und Cellulosefasern |
| DE2740679C2 (de) * | 1977-09-09 | 1980-01-03 | Hoechst Ag, 6000 Frankfurt | Verfahren zum Bedrucken von Cellulosefasergeweben |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2274751A (en) * | 1942-03-03 | Materials | ||
| US2173178A (en) * | 1936-08-05 | 1939-09-19 | Celanese Corp | Dyeing of textile and other materials |
| NL175307B (nl) * | 1952-05-31 | Air Prod & Chem | Werkwijze ter bereiding van opschuimbare vinylharsmengsels, alsmede de hieruit vervaardigde schuimvormige voorwerpen. |
-
1970
- 1970-12-12 DE DE19702061357 patent/DE2061357A1/de active Pending
-
1971
- 1971-12-08 CH CH1787971D patent/CH1787971A4/xx unknown
- 1971-12-08 CH CH1787971A patent/CH554971A/xx unknown
- 1971-12-10 BE BE776540A patent/BE776540A/xx unknown
- 1971-12-10 GB GB5746671A patent/GB1377210A/en not_active Expired
- 1971-12-10 US US00206904A patent/US3787179A/en not_active Expired - Lifetime
- 1971-12-13 FR FR7144672A patent/FR2118054A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2847532A1 (de) * | 1978-11-02 | 1980-05-08 | Bayer Ag | Verfahren zur herstellung von azofarbstoffen |
Also Published As
| Publication number | Publication date |
|---|---|
| CH1787971A4 (enrdf_load_stackoverflow) | 1974-04-30 |
| GB1377210A (en) | 1974-12-11 |
| BE776540A (fr) | 1972-06-12 |
| FR2118054A1 (enrdf_load_stackoverflow) | 1972-07-28 |
| US3787179A (en) | 1974-01-22 |
| CH554971A (enrdf_load_stackoverflow) | 1974-10-15 |
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