US3623831A - Process for dyeing textile material of mixtures of polyester and cellulose fibres - Google Patents

Process for dyeing textile material of mixtures of polyester and cellulose fibres Download PDF

Info

Publication number: US3623831A
Authority: US; United States
Prior art keywords: acid; disperse; polyester; impregnation; mixtures
Prior art date: 1968-04-30
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 - Lifetime

Application number

US820020A

Other languages

English (en)

Inventor

Rudolf Lowenfeld

Uwe Kosubek

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

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.)

1968-04-30

Filing date

1969-04-28

Publication date

1971-11-30

1969-04-28 Application filed by Hoechst AG filed Critical Hoechst AG

1971-11-30 Application granted granted Critical

1971-11-30 Publication of US3623831A publication Critical patent/US3623831A/en

1988-11-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000463 material Substances 0.000 title abstract description 22
229920000728 polyester Polymers 0.000 title abstract description 16
239000004753 textile Substances 0.000 title abstract description 12
239000000203 mixture Substances 0.000 title abstract description 6
238000000034 method Methods 0.000 title description 16
229920003043 Cellulose fiber Polymers 0.000 title description 15
238000004043 dyeing Methods 0.000 title description 8
-1 DIAZOAMINO Chemical class 0.000 abstract description 25
239000002253 acid Substances 0.000 abstract description 18
230000008878 coupling Effects 0.000 abstract description 14
238000010168 coupling process Methods 0.000 abstract description 14
238000005859 coupling reaction Methods 0.000 abstract description 14
150000001875 compounds Chemical class 0.000 abstract description 12
239000000835 fiber Substances 0.000 abstract description 12
238000005470 impregnation Methods 0.000 abstract description 12
238000001035 drying Methods 0.000 abstract description 10
239000000243 solution Substances 0.000 abstract description 10
239000002270 dispersing agent Substances 0.000 abstract description 7
238000010438 heat treatment Methods 0.000 abstract description 7
239000012670 alkaline solution Substances 0.000 abstract description 6
239000000986 disperse dye Substances 0.000 abstract description 3
229920002678 cellulose Polymers 0.000 abstract 1
239000001913 cellulose Substances 0.000 abstract 1
239000000306 component Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000004744 fabric Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000007859 condensation product Substances 0.000 description 6
238000009736 wetting Methods 0.000 description 6
239000000080 wetting agent Substances 0.000 description 6
239000000975 dye Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 4
JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
150000004982 aromatic amines Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229920005610 lignin Polymers 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
OXLITIGRBOEDEZ-UHFFFAOYSA-N 1,5-diamino-4,8-dihydroxy-2-(4-hydroxyphenyl)anthracene-9,10-dione Chemical compound C=1C(O)=C2C(=O)C=3C(N)=CC=C(O)C=3C(=O)C2=C(N)C=1C1=CC=C(O)C=C1 OXLITIGRBOEDEZ-UHFFFAOYSA-N 0.000 description 2
GRMDKKJYMUDEJO-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)-4-[(2-cyano-4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCOC(C)=O)CCOC(=O)C)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N GRMDKKJYMUDEJO-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
FWTBRYBHCBCJEQ-UHFFFAOYSA-N 4-[(4-phenyldiazenylnaphthalen-1-yl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 FWTBRYBHCBCJEQ-UHFFFAOYSA-N 0.000 description 2
YJKJAYFKPIUBAW-UHFFFAOYSA-N 9h-carbazol-1-amine Chemical class N1C2=CC=CC=C2C2=C1C(N)=CC=C2 YJKJAYFKPIUBAW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
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 2
239000002202 Polyethylene glycol Substances 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
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 2
150000004056 anthraquinones Chemical class 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-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
229920001223 polyethylene glycol Polymers 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 2
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
239000002699 waste material Substances 0.000 description 2
SBSBBPZTTALABX-UHFFFAOYSA-N 1,8-diamino-2-bromo-4,5-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=C(Br)C(N)=C2C(=O)C2=C1C(O)=CC=C2N SBSBBPZTTALABX-UHFFFAOYSA-N 0.000 description 1
ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical class NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 1
XYLCZDWOYJRTGC-UHFFFAOYSA-N 2-(4-aminophenoxy)acetonitrile Chemical class NC1=CC=C(OCC#N)C=C1 XYLCZDWOYJRTGC-UHFFFAOYSA-N 0.000 description 1
DVBLPJWQXDCAKU-UHFFFAOYSA-N 2-(4-bromo-3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=C(O)C(Br)=C2C=CC=CC2=N1 DVBLPJWQXDCAKU-UHFFFAOYSA-N 0.000 description 1
PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 1
VQIRFOAILLIZOY-UHFFFAOYSA-N 2-[5-acetamido-n-(2-acetyloxyethyl)-4-[(2-bromo-4,6-dinitrophenyl)diazenyl]-2-ethoxyanilino]ethyl acetate Chemical compound C1=C(N(CCOC(C)=O)CCOC(C)=O)C(OCC)=CC(N=NC=2C(=CC(=CC=2Br)[N+]([O-])=O)[N+]([O-])=O)=C1NC(C)=O VQIRFOAILLIZOY-UHFFFAOYSA-N 0.000 description 1
YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical class NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-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
XCDIDHPTOCAKAB-UHFFFAOYSA-N 3-hydroxy-n-(2-methylphenyl)anthracene-2-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC2=CC3=CC=CC=C3C=C2C=C1O XCDIDHPTOCAKAB-UHFFFAOYSA-N 0.000 description 1
KLZPLKQRIOMCLB-UHFFFAOYSA-N 4-(2-nitroethoxy)aniline Chemical class NC1=CC=C(OCC[N+]([O-])=O)C=C1 KLZPLKQRIOMCLB-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
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
229920002284 Cellulose triacetate Polymers 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-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
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
238000007792 addition Methods 0.000 description 1
PAEJMUPOBGPBPH-UHFFFAOYSA-N aminooxy(oxo)methanesulfonic acid Chemical class NOC(=O)S(O)(=O)=O PAEJMUPOBGPBPH-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
RZLBOHUWUYLABB-UHFFFAOYSA-N n-(2,3-dimethylphenyl)nitramide Chemical class CC1=CC=CC(N[N+]([O-])=O)=C1C RZLBOHUWUYLABB-UHFFFAOYSA-N 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
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
SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical class FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-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 class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003142 primary aromatic amines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000017854 proteolysis Effects 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
239000004627 regenerated cellulose Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
- 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
- D06P3/8238—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye
- D06P3/8257—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye using dispersed and azo dyes prepared in situ
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/908—Anionic emulsifiers for dyeing
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/908—Anionic emulsifiers for dyeing
- Y10S8/912—Arylene sulfonate-formaldehyde condensate or alkyl aryl sulfonate
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/913—Amphoteric emulsifiers for dyeing
- Y10S8/915—Amino sulfonic acids
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/933—Thermosol dyeing, thermofixation or dry heat fixation or development

Definitions

textile material consisting of mixtures of polyester and cellulose fibres may be dyed fast shades, by using disperse dyestuffs and Water-insoluble azo-dyestuffs produced on the fibre.
the process is carried out in such a manner that the portion of polyester fibre is first dyed with disperse dyestuffs at boiling temperature, in the presence of dyeing accelerators or under the conditions of dyeing at high temperatures, and subsequently, the water-insoluble azo-dyestuff is produced on the cellulose fibre portion by impregnation with a coupling component and subsequent development with a diazotized aromatic amine.
the disperse dyestutf the coupling component and the diazotized aromatic amine must each be applied in separate dyeing baths.
Another known process consists in that the textile material is impregnated with an alkaline solution containing a coupling component, a diazoamino compound, a disperse dyestutf and a compound splitting off an acid under the action of heat, it is then dried and, at temperatures in the range of from 180 to 210 C, the Water-insoluble azo dyestuff is then produced on the cellulose fibre portion, the disperse dyestulf being simultaneously fixed on the polyester fibre portion. Finally, the material is subjected to an after-treatment with alkaline agents. This process is very economic.
the textile material for example blended fabrics of polyester and cellulose fibres
an alkaline solution containing a coupling component, a diazoamino or a tetrazoamino compound or an anti diazotate as well as wetting or dispersing agents, and it is then squeezed otf and dried.
the content of alkali in the impregnation, bath is advantageously such that coupling com-ponent does not precipitate in the course of the impregnation, which is carried out at temperatures of from 30 to 50 C.
the textile material is impregnated with a solution containing a compound giving an acid reaction as well as a disperse dyestutf.
the content of the compound giving an acid reaction must be such that, in the course of the alkaline impregnation the alkali applied onto the textile material together with the coupling component is neutralized, and that the pH-value of the goods to be dyed is between about 3 and 7.
the disperse dyestuif is used in an amount such that the polyester fibre portion is dyed with approximately the same intensity as the cellulose fibre portion.
the water-insoluble azodyestuff develops on the cellulose fibre portion, depending on the acidity of the developing bath or the tendency of the diazoamino compound to split off, either in the course of the treatment with the acid bath or during the drying process subsequently to the acid development; while the disperse dyestulf is only fixed in a fast manner on the polyester fibre portion in the course of the heat treatment.
the Water-insoluble azo dyestutf is obtained in full yield and clearness.
the dyeings obtained possess very good fastness properties.
textile materials there may be used blends containing from about 25% of polyester fibre and of cellulose fibre, to 70% of polyester fibre and 30% of cellulose fibre.
polyester fibres are those made of aromatic polyesters, for example terephthalic acid or dipenyl- 4,4'-dicarboxylic acid and alkane diols or 1,4-cyclohexanedimethanol, as well as triacetyl cellulose.
aromatic polyesters for example terephthalic acid or dipenyl- 4,4'-dicarboxylic acid and alkane diols or 1,4-cyclohexanedimethanol, as well as triacetyl cellulose.
cellulose fibres native or regenerated cellulose fibres may be used.
the coupling components which enter into consideration are especially aromatic o-hydroxy-carboxylic acid aryl amides or acylacetic acid aryl amides such as, for example, 2,3-hydroxynaphthoic acid arylamides, 6-bromo or 6-alkoxy-2,3-hydroxynaphthoic acid aryl amides or acetoacetic acid aryl amides whose substantivity with respect to cellulose fibres is weak to medium.
aromatic o-hydroxy-carboxylic acid aryl amides or acylacetic acid aryl amides such as, for example, 2,3-hydroxynaphthoic acid arylamides, 6-bromo or 6-alkoxy-2,3-hydroxynaphthoic acid aryl amides or acetoacetic acid aryl amides whose substantivity with respect to cellulose fibres is weak to medium.
coupling components which have a high substantivity with respect to cellulose fibres, for instance the condensation products of 2,3-hydroxynaphthoic acids with polynuclear isocyclic or heterocyclic amines, such as amino-naphthalenes, aminocarbazoles 0r aminodiphenylene oxides, moreover heterocyclic o-hydroxy carboxylic acid aryl amides, for example S-hydroxy- 1,2,1',2'-benzocarbazol-4-carboxylic acid aryl amides.
diazoamino or tetrazoamino compounds there may be taken into consideration the products prepared from diazotized aromatic or heterocyclic monoamines or diamines, for example from diazotized chloro-anilines, dichloro-anilines, chloro-toluidines, chloroanisidines, nitroanilines, nitrotoluidines, nitroanisidines, nitroxylidines, nitrophenetidines, cyanotoludines, cyanoanisidines, aminobenzene sulfonic acid amides, aminobenzene carboxylic acid amides, aminophenyl alkyl aryl or aralkyl sulfones, aminodiphenyl ethers, trifluoromethyl anilines, monoacylated phenylenediamines, aminoazobenzenes, 4,4'-diaminophenols or aminocarbazoles and primary or secondary aliphatic or aromatic amines, for example N-alkylated
anti-diazotates there may also be considered the compounds obtainable from the above-mentioned primary aromatic amines.
wetting and dispersing agents in the alkaline impregnation bath may be used especially condensation products of higher molecular fatty acids and protein degradation products, condensation products of higher molecular fatty acids and aminoalkylsulfonic acids, condensation products of formaldehyde and naphthalene sulfonic acids as well as purified spent lignin liquor.
the compounds giving an acid reaction in the develop ing bath are either organic acids such as, for example, formic acid, acetic acid, propionic acid, lactic acid, glycolic acid, tartaric acid or citric acid, or salts giving an acid reaction such as, for example, monosodium phosphate as well as ammonium chloride which when heated, has an acid reaction.
organic acids such as, for example, formic acid, acetic acid, propionic acid, lactic acid, glycolic acid, tartaric acid or citric acid
salts giving an acid reaction such as, for example, monosodium phosphate as well as ammonium chloride which when heated, has an acid reaction.
dyestuffs which, due to their thermal properties, can be used in the so-called thermosol treatment, i.e. dyestuffs which dye of water of 60 C., 20 g. of 2,3-hydroxynaphthoylamino benzene, dissolved in ml. of denaturized alcohol, 10 ml. of a 32.5% sodium hydroxide solution and 50 ml. of Water of 40 C., the diazoamino compound of 8.4 g. of diazotized 1-amino-2-methyl-S-chlorobenzene and sodium cyanamide, 30 ml. of a 32.5% sodium hydroxide solution and 4 g.
thermosol treatment i.e. dyestuffs which dye of water of 60 C., 20 g. of 2,3-hydroxynaphthoylamino benzene, dissolved in ml. of denaturized alcohol, 10 ml. of a 32.5% sodium hydroxide solution and 50 ml.
the fabric was squeezed to an absorption of liquor of 70%, dried, impregnated with a solution containing, per litre of water of C., 20 g. of C.I. Disperse Red 90, 60 ml. of a 50% acetic acid solution and 2 g. of a condensation product of formaldehyde with fi-naphthalenesulfonic acid, and squeezed off until the liquor absorption had reached of the dry goods weight.
the fabric was passed through a drying aggregate, and then through a fixation chamber or over hot rollers in a manner such that the fabric was heated to 1802l0 C. during 30 'to 60 seconds.
the fabric was then soaped at boiling temperature with 1 g. of a reaction product of 10 moles of ethylene oxide and 1 mole of nonyl phenol and 3 g. of sodium hydroxide per litre of water, rinsed and dried. A full clear red dyeing with good fastness prop erties was obtained, the polyester fibre and the cellulose fibre portion being dyed the same shade.
the following table indicates a series of further coupling components, diazoamino compounds of anti-diazotates to be used according to the invention, as well as disperse dyestuffs and the shades obtainable thereof on mixed fabrics of fibres of polyethylene glycol terephthalate polyester fibres at temperatures in the range of from 170 30 (67%) and cotton (33% Coupling component Diazoamino compound (DA) or antidiazotate (A 1-(2,3'-hydroxynaphthoylamino)-2-methoxybenzene.
DA Diazoamino compound
antidiazotate A 1-(2,3'-hydroxynaphthoylamino-2-methoxybenzene.
DA from diazotized l-amino'2-methyl-5-chl0ro- DA from diazotized 1-amino-2-methyl-5-chlo1'obenzene and sodium cyanamide.
Suitable disperse dyestuffs of the azo and anthraquinone series are described in Colour Index, second edition 1956, vol. 1, pp. 1659-1742, and Supplement 1953, pp. 8179-5224, and in the corresponding Additions and Amendments, No. 1, September 1963 to No. 17, October 1967.
the process of the invention may be carried out continuously or semi-continuously.
EXAMPLE A blended fabric consisting of 67% of a polyethylene glycol terephthalate fibre and of 33% of a cotton fibre was impregnated with a solution containing, as per litre (c) impregnating this dried material with an acid solution containing a disperse dyestuff to obtain a pH (e) subjecting this dried material to heat treatment at a temperature in the range of about C. to
the coupling component is an aromatic o-hydroxy-carboxylic acid arylamide or an acylaceto aryl amide.
the wetting or dispersing agent is a condensation product of a long chain fatty acid and an aminoalkyl sulfonic acid or of formaldehyde and a naphthalene sulfonic acid or a purified waste lignin liquor.

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Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Chemical & Material Sciences (AREA)
Dispersion Chemistry (AREA)
Coloring (AREA)

US820020A 1968-04-30 1969-04-28 Process for dyeing textile material of mixtures of polyester and cellulose fibres Expired - Lifetime US3623831A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1769278A DE1769278C3 (de)	1968-04-30	1968-04-30	Verfahren zum Färben von Textilmaterial aus Mischungen von Polyesterfasern mit Cellulosefasern

Publications (1)

Publication Number	Publication Date
US3623831A true US3623831A (en)	1971-11-30

Family

ID=5700077

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US820020A Expired - Lifetime US3623831A (en)	1968-04-30	1969-04-28	Process for dyeing textile material of mixtures of polyester and cellulose fibres

Country Status (8)

Country	Link
US (1)	US3623831A (de)
AT (1)	AT294756B (de)
BE (1)	BE732360A (de)
CH (2)	CH644969A4 (de)
DE (1)	DE1769278C3 (de)
FR (1)	FR2007312A1 (de)
GB (1)	GB1235783A (de)
NL (1)	NL6905623A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3713767A (en) *	1969-06-24	1973-01-30	Hoechst Ag	Process for the dyeing of textile material of mixtures of polyester fibers and cellulose fibers

1968
- 1968-04-30 DE DE1769278A patent/DE1769278C3/de not_active Expired
1969
- 1969-04-11 NL NL6905623A patent/NL6905623A/xx unknown
- 1969-04-28 AT AT409269A patent/AT294756B/de not_active IP Right Cessation
- 1969-04-28 CH CH644969D patent/CH644969A4/xx unknown
- 1969-04-28 US US820020A patent/US3623831A/en not_active Expired - Lifetime
- 1969-04-28 CH CH644969A patent/CH511975A/de not_active IP Right Cessation
- 1969-04-30 BE BE732360D patent/BE732360A/xx unknown
- 1969-04-30 GB GB21970/69A patent/GB1235783A/en not_active Expired
- 1969-04-30 FR FR6913798A patent/FR2007312A1/fr active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3713767A (en) *	1969-06-24	1973-01-30	Hoechst Ag	Process for the dyeing of textile material of mixtures of polyester fibers and cellulose fibers

Also Published As

Publication number	Publication date
BE732360A (de)	1969-10-30
NL6905623A (de)	1969-11-03
CH644969A4 (de)	1971-05-14
FR2007312B1 (de)	1973-10-19
DE1769278A1 (de)	1972-03-30
GB1235783A (en)	1971-06-16
CH511975A (de)	1971-05-14
FR2007312A1 (fr)	1970-01-02
DE1769278B2 (de)	1973-06-20
DE1769278C3 (de)	1974-02-07
AT294756B (de)	1971-12-10

Publication	Publication Date	Title
US2317965A (en)	1943-04-27	Process of coloring fibrous materials and the materials obtained thereby
US3713767A (en)	1973-01-30	Process for the dyeing of textile material of mixtures of polyester fibers and cellulose fibers
US2148659A (en)	1939-02-28	Process for the production of fast tints on cellulosic fibers
US2095600A (en)	1937-10-12	Process for the production of fast tints on the fiber
US3642424A (en)	1972-02-15	Process for dyeing textile material of mixtures of polyester and cellulose fibers
US3623831A (en)	1971-11-30	Process for dyeing textile material of mixtures of polyester and cellulose fibres
US2078388A (en)	1937-04-27	Dyeing process and composition
US3787179A (en)	1974-01-22	Process for the manufacture of insoluble azo dyestuffs on cellulose fibers
US3679350A (en)	1972-07-25	Process for the dyeing of textile materials made from mixtures of polyester and cellulosic fibres
US3265460A (en)	1966-08-09	Dyeing of synthetic fibers
CH644969A5 (de)	1984-08-31	Druckgasschalter.
US4110071A (en)	1978-08-29	Process for the tone-in-tone printing and pad-dyeing of textile material made from fibre mixtures
US3552905A (en)	1971-01-05	Method for producing permanent, press, dyed, polyester-cellulosic blended fabrics
US3708257A (en)	1973-01-02	Process for the dyeing of textile material made from mixtures of polyester and cellulosic fibers
US3389956A (en)	1968-06-25	Dyeing nickel-modified polypropylene texteiles with an acyl dihydroxybenzene azo dye
US2819943A (en)	1958-01-14	Process for dyeing or printing fibers of polyacrylonitriles
US2957745A (en)	1960-10-25	Dyeing and printing of synthetic high polymeric polyesters
US3494716A (en)	1970-02-10	Printing and dyeing of polyester and cellulosic fibers and blends thereof
US3043647A (en)	1962-07-10	Colouring of polyester fiberes
DE1262957C2 (de)	1968-10-03	Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial aus Cellulose- oder Eiweissfasern
US3383160A (en)	1968-05-14	Method for dyeing polyester fibers with monoazo dyestuffs
US3845032A (en)	1974-10-29	Alkylbenzoateazohydroxynaphtharylide dyestuffs
US2154405A (en)	1939-04-11	Stable icb oolob pbododng
US3549311A (en)	1970-12-22	Nitrodiphenylamine disperse dyes
US3484181A (en)	1969-12-16	Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers

US3623831A - Process for dyeing textile material of mixtures of polyester and cellulose fibres - Google Patents

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Applications Claiming Priority (1)

Publications (1)

Family

ID=5700077

Family Applications (1)

Country Status (8)

Cited By (1)

Cited By (1)

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