US1968879A - Process for dyeing and printing - Google Patents
Process for dyeing and printing Download PDFInfo
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- US1968879A US1968879A US1968879DA US1968879A US 1968879 A US1968879 A US 1968879A US 1968879D A US1968879D A US 1968879DA US 1968879 A US1968879 A US 1968879A
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- 238000000034 method Methods 0.000 title description 36
- 238000004043 dyeing Methods 0.000 title description 20
- 150000001875 compounds Chemical class 0.000 description 70
- 239000000203 mixture Substances 0.000 description 66
- 239000000463 material Substances 0.000 description 62
- 230000001808 coupling Effects 0.000 description 48
- 238000010168 coupling process Methods 0.000 description 48
- 238000005859 coupling reaction Methods 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000002253 acid Substances 0.000 description 32
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 32
- 150000004982 aromatic amines Chemical class 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 24
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 22
- 150000001412 amines Chemical class 0.000 description 20
- 239000004744 fabric Substances 0.000 description 20
- 125000003710 aryl alkyl group Chemical group 0.000 description 16
- 238000004040 coloring Methods 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 16
- 239000002562 thickening agent Substances 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 235000019253 formic acid Nutrition 0.000 description 12
- 230000001264 neutralization Effects 0.000 description 12
- 239000004753 textile Substances 0.000 description 12
- 229960000583 Acetic Acid Drugs 0.000 description 10
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 10
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 10
- MBBZMMPHUWSWHV-BDVNFPICSA-N Meglumine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 10
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 10
- 239000004305 biphenyl Substances 0.000 description 10
- 125000006267 biphenyl group Chemical group 0.000 description 10
- 239000000835 fiber Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- MSCMTURKIQRYPE-UHFFFAOYSA-N 2-hydroxyanthracene-1-carboxylic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=C(O)C=CC3=CC2=C1 MSCMTURKIQRYPE-UHFFFAOYSA-N 0.000 description 8
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 8
- KJKBAKXVJKBGGV-UHFFFAOYSA-N OC1=C(C=2C=CC3=C(C=CC=4C=5C=CC=CC5NC34)C2C=C1)C(=O)O Chemical compound OC1=C(C=2C=CC3=C(C=CC=4C=5C=CC=CC5NC34)C2C=C1)C(=O)O KJKBAKXVJKBGGV-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001716 carbazoles Chemical class 0.000 description 8
- 238000005755 formation reaction Methods 0.000 description 8
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 6
- 229920001615 Tragacanth Polymers 0.000 description 6
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 6
- 229950011260 betanaphthol Drugs 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 150000002790 naphthalenes Chemical class 0.000 description 6
- IKXCHOUDIPZROZ-LXGUWJNJSA-N (2R,3R,4R,5S)-6-(ethylamino)hexane-1,2,3,4,5-pentol Chemical compound CCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IKXCHOUDIPZROZ-LXGUWJNJSA-N 0.000 description 4
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000006011 modification reaction Methods 0.000 description 4
- 239000008149 soap solution Substances 0.000 description 4
- 230000003381 solubilizing Effects 0.000 description 4
- QVEUDPHFUKJQHH-SGIHWFKDSA-N (2R,3R,4R,5S)-6-(butylamino)hexane-1,2,3,4,5-pentol Chemical compound CCCCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO QVEUDPHFUKJQHH-SGIHWFKDSA-N 0.000 description 2
- GXDKMPKEMFWETC-IRCOFANPSA-N (2R,3R,4R,5S)-6-(cyclohexylamino)hexane-1,2,3,4,5-pentol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CNC1CCCCC1 GXDKMPKEMFWETC-IRCOFANPSA-N 0.000 description 2
- IPVTTYAHKXZGCQ-QOCHGBHMSA-N (4Z)-3-oxo-4-[(4-sulfonaphthalen-1-yl)hydrazinylidene]naphthalene-2,7-disulfonic acid Chemical compound C1=CC=C2C(N/N=C3/C4=CC=C(C=C4C=C(C3=O)S(=O)(=O)O)S(O)(=O)=O)=CC=C(S(O)(=O)=O)C2=C1 IPVTTYAHKXZGCQ-QOCHGBHMSA-N 0.000 description 2
- XHRCFGDFESIFRG-UHFFFAOYSA-N 2-chloro-N-ethyl-N-[(2-methylphenyl)methyl]ethanamine Chemical compound ClCCN(CC)CC1=CC=CC=C1C XHRCFGDFESIFRG-UHFFFAOYSA-N 0.000 description 2
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-o-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- MNQZXJOMYWMBOU-UHFFFAOYSA-N Glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 2
- XQQKUHVBSOCJTL-UHFFFAOYSA-L S(=O)(=O)([O-])[O-].[Na+].[Na+].C(C)(=O)O.C(=O)O Chemical compound S(=O)(=O)([O-])[O-].[Na+].[Na+].C(C)(=O)O.C(=O)O XQQKUHVBSOCJTL-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 150000001323 aldoses Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000002939 deleterious Effects 0.000 description 2
- -1 dlphenyl Chemical compound 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004674 formic acids Chemical class 0.000 description 2
- 229920000591 gum Polymers 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000001145 hydrido group Chemical group *[H] 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000001603 reducing Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 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
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
Definitions
- compositions comprising an ice color 6 coupling component and a diazoimino compound which is produced by coupling a secondary sugar amine with a diazotized aromatic amine containing no water solubilizing group.
- the material to be dyed or printed is treated with a mixture comprising anice color coupling component and a diazoimino compound which is produced by coupling a secondary sugar amine with a, diazotized aromatic amine containing no water solubilizing group.
- This diazoimino compound has the following general formula:
- Aryl represents an aromatic radical
- omouomiomon was mixed mechanically with 5.03 parts of the ortho-toluidide of 2:3-hydroxy-naphthoic-acid. To this mixture was added with stirring 3.00 parts of Turkey red oil, followed by 5.70 parts of a 30 per cent solution of sodium hydroxide. 18.77 parts of water heated to 160 F. was neat added; and when a clear solution was obtained, 60.00 parts of a neutral starch-gum tragacanth thickener was added. The whole was agitated to a smooth printing paste.
- Cotton piece goods were printed from an engraved copper roll with the above paste. The printed fabric was dried in the air, then steamed.
- a developing bath of the following composition was prepared and heated to 205 F.:
- Example I 7.5 parts of the dry diazoimino compound prepared by the action of methyl-glucamine on di- When color development was complete, the printed fabric was rinsed, soaped with a hot soap solution, again rinsed and dried.
- the pattern was developed to a beautiful orange shade, showing excellent fastness to washing, light, and so forth.
- Example II A printing paste of the following composition was prepared as in Example No. I.
- Example III A printing paste of the following composition was prepared:
- Example IV The process of Example No. III was repeated,
- Example V A printing paste was prepared of the following composition:
- the bath being previously heated to 205 F. and held at this temperature during the color development.
- the dyestufl? was completely formed on the fiber, the cloth was washed, soaped, rinsed 0 and dried. The pattern was developed as a bright red of good iastness properties.
- the dyestufi was identical with that obtained in the previous example.
- Example VI A printing paste was prepared from:
- Example VIII Cotton piece goods were printed with the above paste, from an engraved roll. The printed fabric was then subjected to the action of saturated steam containing the vapors of acetic acid, at a temperature of about 212 F. Rapid development of the pattern to a bright red was effected. When the formation of color was complete, the fabric was rinsed, soaped at the boil, rinsed and dried. The fast red printing had resulted from the formation 0! the "ice-color of the probable formula:
- Example X Well-boiled and dried cotton yarn was im pregnated with the anilide oi 2:3-hydroxynaphthoic-acid wrung as dry as possible, and immediately developed in the following bath:
- Example XI Cotton piece goods were impregnated with the ortho-toluidide of 2:3-hydroxy-naphthoic-acid in the usual manner. It was dried, then printed from an engraved roll with a paste of the following composition:
- 3-nitro-4-amino-toluene 2:5-dichloroaniline, 4-chloro-2-amino-toluene, 4-chloro-2-amino-anisol, ortho-chloro-aniline, meta-chloro-anlline.
- para-nitraniline 1 -amino-4-benzoylamino-2 5- diethoxy-benzene
- 4-chloro-2-nitro-aniline N- (para amino benzoyl) -aniline, ortho phenetidine-azo-a.lpha-naphthylamine, para-anisidineazo-2 S-dimethoxy-aniline, alpha amino an thraquinone, 3-amino-carbazole, dianisldine, para-amino-diphenyl, 4,4'-diamino-diphenylamine, 1-amino-2-methoxy-naphthalene.
- Preparation of the secondary sugar amines may be carried out by any of the usual processes.
- CHO-(CHOH) :CHzOH in which a: represents one of the integers 2, 3, 4; and a primary amine having the general formula:
- R represents an alkyl, aralkyl, or completely reduced carbocyclic group.
- the different optical modifications of the aldoses namely, the dextro-, laevo-, meso-, and racemic modifications may be used in preparing this secondary sugar amine.
- the diazoimino compound may then be mixed with one of the usual ice color coupling components.
- one of the usual ice color coupling components such as an arylamide 0f 2-3-hydroxynaphthoic acid, an arylamide of hydroxy-carbazoleor hydroxy-naphthocarbazole-carboxylic acid, an arylamide of hydroxy-anthracene-carboxylic acid, alphaor beta-naphthol, an acetoacetyl derivative of an arylamine, or phenylmethyl pyrazolone.
- this mixture may contain one or more diazoimino compounds and. one or more ice color coupling components, since certain shades are obtained by using more than one and/or more than one ice color coupling component which could not be obtained otherwise.
- the textile material is printed orimpregnated with this mixture, and then treated with an acid, preferably a weak acid at elevated to hydrolyze the diazoimino compound and permit coupling to take place between the regenerated diazo salt and the ice color coupling component.
- an acid preferably a weak acid at elevated to hydrolyze the diazoimino compound and permit coupling to take place between the regenerated diazo salt and the ice color coupling component.
- Acetic and/or formic acids have been found to give very satisfactory results but the invention is not limited to these acids since hydrolysis of the diazoimino compound may be effected by numerous other acids or mixtures of acids, well known to one skilled in the art.
- the acid or acids used in treating the printed or impregnated diazoimino compound temperatures, 1;.
- textile material may be in either the liquid or vapor phase.
- the ice color coupling component or components and the diazolmino compound or compounds need not be applied to the textile material simultaneously, but one may be applied prior to the other, the resulting reaction being fundamentally the same regardless of the order in which the reactants are applied.
- the process described in the present disclosure produces excellent dyeings and prlntings on textile material in a much more simplified manner than was previously possible.
- the colors produced are exceptionally uniform and fast, due in great part to the thorough impregnation of the fibers with the very soluble diazoimino compound. No deleterious side reactions take place to impair the efliciency of the process and the appearance and properties of the products produced.
- the secondary sugar amine, produced upon hydrolysis of the diazoimino compound does not have a strong reducing effect, consequently, it does not reduce the diazo salt or interfere in any manner with the coupling of this diazo salt and the ice color coupling component.
- the compounds used are readily available at a very reasonable cost, and in addition the simplification of the printing or dyeing processes results in an appreciable saving to the manufacturer.
- a process for coloring material which comprises treating the material with a mixture comprising an ice color coupling component and a diazoimino compound, produced by coupling a secondary sugar amine with a diazotized aromatic amine containing no water-solubilizin'g group, then developing the color by subjecting the treated material to the action of a weak acid at elevated temperatures.
- a process for coloring material which comprises treating the material with a mixture comprising an ice color coupling component and a diazoimino compound having the following general formula:
- Aryl represents the residue of an aromatic amine containing no water-solubilizing group
- Z represents the residue of a secondary sugar amine
- a process for coloring material- which comprises treating the material with a mixture comprising an ice color coupling component and, a,
- Aryl represents the residue-of an and-- amine which may have non-water-solubilizing groups substituted thereon
- R represents an alkyl, aralkyl, or completely'reduced carbocyclic radical
- x represents one of the integers 2, 3, 4, then developing the color by subjecting the treat-' ed material to the action of a weak acid, preferably at elevated temperatures.
- a process for coloring material which comprises treating the material with a mixture cornprising an ice color coupling component and a diazoimino compound having the following general formula: I
- Aryl represents the residue of an I arylamine of the benzene, diphenyl, naphthalene, diphenylamine, azobenzene, anthraquinone or carbazole series, which may have non-water-solu bilizing groups substituted thereon, It represents an alkyl, aralkyl, or completely reduced carbocyclic radical, and :z: represents one of the integers 2, 3, 4, then developing the color by sub- ,iecting the treated material to the action of a weak acid, preferably at elevated temperatures.
- a process for coloring material which comprises treating'tl'ie material with a mixture comprising an ice color coupling component selected from the group consisting of arylamides of 2-3- hydroxy-naphthoic acid, arylamides of hydroxycarbazoleor hydroxy-naphthocarbazole-carboxylic acids, arylamides of hydroxy-anthracenecarboxylic acids, alphaor beta-naphthol, ace-, toacetyl derivatives of arylamines, and phenylmethyl-pyrazolone, and a diazoimino compound having the following general formula: 1%
- Aryl represents the residue of an aryl- 12g amine of the benzene, diphenyl, naphthalene, diphenylamine, azobenzene, anthraquinone, or carbazole series, which may have non-water-solubilizing groups substituted thereon
- R represents an alkyl, arallryl, or completely reduced carbocyclic radical
- :2: represents one of the integers 2, 3, 4, then developing the color by subjecting the treated material to the action of a weak acid at elevated temperatures.
- a process for coloring material which comprises treating the materlal with a mixture comprising an ice color coupling component selected from the group consisting of arylamides of 2-3- hydroxy-naphthoic acid, arylamides of hydroxycarbazoleor hydroxy-naphthocarbazole-carboxylic acids, arylamides of hydroxy-anthracenecarboxylic acids, alphaor beta-naphthol, acetoacetyl derivatives of arylamines, and phenylmethyl-pyrazolone, and a diazoimino compound having the following general formula:
- Aryl represents the residue of an arylamine of the benzene or naphthalene series which may have substituted'thereon non-watersolubilizing groups
- R represents an alkyl, aralkyl, carbocyclic radical
- :n represents one of the integers 2, 3, 4, then developing the color by subjecting the treated material to the action of an acid selected from the group consisting of acetic and formic acid, at elevated temperatures.
- a process for coloring material which comprises treating the material with a mixture comprising an arylamide of 2-3-hydroxy-naphthoic acid having the following general formula:
- Aryl-N N-N cmwnommmon in which Aryl represents the residue of an arylamlne of the benzene series, which may have substituted thereon members selected from the class consisting of halogen, alkyl, alkoxy, nitro and benzoyl-amino groups, R represents an alkyl group, and :2: represents one of the integers 2, 3, 4, then developing the color by subjecting the treated material to the action ofan acid selected from the group consisting of acetic and formic acid, at elevated temperatures.
- composition of matter which comprises an ice color coupling component and a diazoimino compound having the following general formula:
- Aryl represents the residue of an aromatic amine containing no water-solubilizing group
- Z represents the residue of a secondary sugar amine
- composition of matter which comprises an ice color coupling component and a diazoimino compoundhaving the following general formula:
- Aryl represents the residue of an arylamine of the benzene, dlphenyl, naphthalene, diphenylamine, azobenzene, anthraquinone or carbazole series, which may have non-water-solubilizing groups substituted thereon,
- R represents an alkyl, aralkyl, or completely reduced carbocyclic radical, and :1: represents one of the integers 2. 3, 4.
- a composition of matter which comprises an ice color coupling component selected from the group consisting of arylamides of 2-3-hydroxy-naphthoic acid, arylamides of hydroxyor hydroxy-naphthocarbazole-carboxylic acids, arylamides of hydroxy-anthracenecarboxylic acids, alphaor beta-naphtha], acetoacetyl derivatives of arylamines, and phenylmethyl-pyrazolone; and a diazoimino compound having the following general formula:
- Aryl represents the residue of an an]- amine of the benzene, diphenyl, naphthalene, diphenylamine, azobenzene, anthraquinone or carbazole series, which may have non-water-solubilizing groups substituted thereo
- R represents an alkyl, aralkyl, or completely reduced carbocyclic radical, and :2: represents one of the integers 2, 3, 4.
- composition of matter which comprises an arylamide of z-3-hydroxy naphthoic acid having the following general formula:
- ONE-R in which R represents the residue of an arylamine of the benzene ornaphthalene series which may have non-water-solubilizing groups substituted thereon, and a diazoimino compound having the following general formula:
- Aryl-N N-N om(cnon),cmorr in which Aryl represents the residue of an arylamine of the benzene or naphthalene series which may have substituted thereon non-watersolubilizing groups, R represents an alkyl, aralkyl,
- composition of matter which comprises an arylamide of 2-3-hydroxy-naphthoic acid having the following general formula:
- X and Y represent hydrogen, halogen, alkyl or alkoxy groups, and a diazoimino compound having the following general formula:
- Aryl-N NN ormononnomon in which X represents hydrogenor an alkyl or alkoxy group.
Description
Patented Aug. 7, 1934 UNITED STATES PATENT OFFICE PROCESS FOR DYEING AND PRINTING TEXTILE MATERIAL Miles Augustinus Dahlen, Wilmington,
and
Frithjof Zwilgmeyer, Gordon Heightu. Del.I aasiqnors to E. I. du Pont de Nemours & Company, Wilmington, Del., a corporation Delaware No Drawing. Application December 8, 1932,
. Serial No. 645,585
16 Claims.
ing with compositions comprising an ice color 6 coupling component and a diazoimino compound which is produced by coupling a secondary sugar amine with a diazotized aromatic amine containing no water solubilizing group.
It is an object of this invention to produce 10 dyeings and printings of excellent fastness on textile material. A further object is to produce results which are superior to those obtained with the tedious dyeing and printing processes previously used, by a much simpler method. Addil tional objects will appear hereinafter.
These objects are attained by the present invention wherein the material to be dyed or printed is treated with a mixture comprising anice color coupling component and a diazoimino compound which is produced by coupling a secondary sugar amine with a, diazotized aromatic amine containing no water solubilizing group. This diazoimino compound has the following general formula:
Aryl" represents an aromatic radical" (Ci. M)
azotized meta-chloroaniline, of the tollowinz probable structure:
one
omouomiomon was mixed mechanically with 5.03 parts of the ortho-toluidide of 2:3-hydroxy-naphthoic-acid. To this mixture was added with stirring 3.00 parts of Turkey red oil, followed by 5.70 parts of a 30 per cent solution of sodium hydroxide. 18.77 parts of water heated to 160 F. was neat added; and when a clear solution was obtained, 60.00 parts of a neutral starch-gum tragacanth thickener was added. The whole was agitated to a smooth printing paste.
Cotton piece goods were printed from an engraved copper roll with the above paste. The printed fabric was dried in the air, then steamed.
A developing bath of the following composition was prepared and heated to 205 F.:
Pam; Glacial acetic acid 1.0 Formic acid 0.5 Giaubers sa 2.5 Water 96.0
- 100.0 The printed and aged fabric was immersed in the bath for about 20 seconds, holding the temperature at 205 F., resulting in the development according to the printed pattern of the dyestufl of the following probable formula:
The invention will be more completely understood by reference to the following illustrative 40 examples in which the quantities are stated in parts by weight.
Example I 7.5 parts of the dry diazoimino compound prepared by the action of methyl-glucamine on di- When color development was complete, the printed fabric was rinsed, soaped with a hot soap solution, again rinsed and dried.
The pattern was developed to a beautiful orange shade, showing excellent fastness to washing, light, and so forth.
Example II A printing paste of the following composition was prepared as in Example No. I.
7.0 parts of the diazoimino compound obtained by the action of diazotized metachloroaniline on methyl-galactamine, of the probable formula:
2.85 parts of the ortho-toluidide of 2:3-hydroxy-naphthoic-acid 3.00 parts of sodium hydroxide solution of 30 per cent strength 87.15 parts of neutral thickener The fabric was printed and steamed according to the method described in the previous example, and the dyestuif developed by the same procedure. The color formed on the fiber was chemically identical with that obtained according to Example No. I, and the printed pattern was again developed as a beautiful orange of excellent fastness properties.
Example III A printing paste of the following composition was prepared:
5.4 parts of the diazoimino compound ob- Cotton piece goods were printed with the above paste, from an engraved copper roll, the printed material dried and then subjected to the action of live steam containing acetic acid vapors. When color development was complete, the printed fabric was washed with water, treated with a hot soap solution, rinsed and dried. The pattern was developed as a bright red dyeing of excellent fastness properties, the color being due to the development on the fiber of the dyestuif of the probable formula:
i c ONHQ Example IV The process of Example No. III was repeated,
using a paste of the following composition:
2.7 parts of the reaction product of diazotized 4-chloro-2-amino-anisole and butylglucamine, of the probable formula:
OCH:
10.0 parts of ethyl alcohol 14.8 parts of water 2.96 parts of the ortho-anisidide of 2:3-hydroxy-naphthoic-acid 3.00 parts of caustic soda solution of 30 per cent strength 66.54 parts of neutral thickener The pattern was developed to a bright red, due to the formation of the dyestufi of the formula given in the previous example.
Example V A printing paste was prepared of the following composition:
2.7 parts of the diazoimino compound obtained by the action of butyl-xylamine on diazotized 4-chloro-2-amino-anisole, of the following probable formula:
10.0 parts of 23 alcohol 14.8 parts of water 2.96 parts of the ortho-anisidide of 2:3-hydroxy-naphthoic-acid 3.00 parts of sodium hydroxide solution of 30 per cent strength 66.54 parts of neutral thickener The printed fabric was developed without steaming in a bath prepared from:
Parts Acetic acid 100% 1.0 Formic acid 85% 0.5 Sodium sulfate 2.5 Water 96.0
the bath being previously heated to 205 F. and held at this temperature during the color development. When the dyestufl? was completely formed on the fiber, the cloth was washed, soaped, rinsed 0 and dried. The pattern was developed as a bright red of good iastness properties. The dyestufi was identical with that obtained in the previous example.
Example VI A printing paste was prepared from:
3.92 parts of the reaction product oif diazotized para-chloro-ortho-toluidine and methyl-glucamine, of the probable formula:
CHI
4.28 partsof the ortho-phenetidide of 2:3 hy-' droxy-naphthoic-acid 3.00 parts oi Turkey red oil '7 .00 parts of caustic soda of 30 per cent strength 14.80 parts of water heated to 160 F. 67.00 parts of starcht-tragacanth thickener The cotton piece goods were printed as in the previous example and the dyestufl developed on the fiber by treatment in the acetic-acid-formicacid-sodium-sulfate bath at 200-210 F. The pattern was developed as a bright scarlet dyeing of excellent fastness properties, the color being due tie the formation of the dyestufi oi the probable formula:
Example VII Equal quantities of the diazoimino compound from diazotized 4-chlorc=-2-toluidine and methylglucamine, of the formula given in the previous example, and the sodium salt of the orthophenetidide of 2:3-hydroxy-naphthoic-acid were intimately mixed. A printing paste of the following composition was then prepared:
Parts Mixture of diazoimino compound and orthophenetidide of 2:3-hydroxynaphthoic-== arid 8.6 Water 23.2 Turkey red o 3.0 Caustic soda of 30 per cent strength 3.2 Neutral thickener 62.0
Cottongoods were printed and developed as in the previous example, the same excellent scarlet dyeing being obtained.
Example VIII Cotton piece goods were printed with the above paste, from an engraved roll. The printed fabric was then subjected to the action of saturated steam containing the vapors of acetic acid, at a temperature of about 212 F. Rapid development of the pattern to a bright red was effected. When the formation of color was complete, the fabric was rinsed, soaped at the boil, rinsed and dried. The fast red printing had resulted from the formation 0! the "ice-color of the probable formula:
on; v
- 1 I ONHQ V Ha Example UK The process of Example No. VIII was repeated,
using a paste of the following compositiom.
2.7 parts of the diazoiminc compound obtained by the action of diazotized 4- chloro -'2 amino toluene on methyh xylamine, of the probable formula:
10.0 parts of ethyl alcohol 14.8 parts of water 2.96 parts of the ortho-toluidide of 213-113;- droxy-naphthoic-acid 3.00 parts of sodium hydroxide of 30 per cent strength 66.54; parts of neutral thickener As in the previous example, the pattern was developed as a beautii'ulred dyeing of excellent fastness properties. The dyestuif of the formula. given in that example is also formed in this case.
Example X Well-boiled and dried cotton yarn was im pregnated with the anilide oi 2:3-hydroxynaphthoic-acid wrung as dry as possible, and immediately developed in the following bath:
5. parts or the diazoimino compound obtained by the action of diazotized meta-chloroaniline on ethyl-glucamine, of the probable formula:
i. 0 part of glacial acetic acid 0. part of formic acid 2. 5 parts of Glauber's salt 91. 0 parts of water After color development was complete, the yarn was rinsed, soaped at the boil, rinsed and dried. The fastness of the dyeing thus obtained is excellent.
Example XI Cotton piece goods were impregnated with the ortho-toluidide of 2:3-hydroxy-naphthoic-acid in the usual manner. It was dried, then printed from an engraved roll with a paste of the following composition:
8parts of the diazoimino compound obtained by the action of methyl-glucamine on diazotized meta-chloro-aniline, of the formula given in Example No. I 3 parts of Turkey red oil 1 part of caustic soda of per cent strength 23 parts of water parts of starch-gum tragacanth thickener The printed fabric was steamed, then developed by the method described in Example No. I. The
printed material was washed in the usual manmatic amines commonly used in the ice color art, among which are the following:
3-nitro-4-amino-toluene, 2:5-dichloroaniline, 4-chloro-2-amino-toluene, 4-chloro-2-amino-anisol, ortho-chloro-aniline, meta-chloro-anlline. para-nitraniline, 1 -amino-4-benzoylamino-2 5- diethoxy-benzene, 4-chloro-2-nitro-aniline, N- (para amino benzoyl) -aniline, ortho phenetidine-azo-a.lpha-naphthylamine, para-anisidineazo-2 S-dimethoxy-aniline, alpha amino an thraquinone, 3-amino-carbazole, dianisldine, para-amino-diphenyl, 4,4'-diamino-diphenylamine, 1-amino-2-methoxy-naphthalene.
Methyl-glucamine, ethyl-glucamine, cyclohexyl-glucamine, benzyl-xylamine, methylerythramine, ethyl galactamine, amyl-arabinamine, methyl-mannamine.
Preparation of the secondary sugar amines may be carried out by any of the usual processes. For example, the liquid phase catalytic hydrogenation of a mixture of an aldose of the following general formula:
CHO-(CHOH) :CHzOH in which a: represents one of the integers 2, 3, 4; and a primary amine having the general formula:
in which R represents an alkyl, aralkyl, or completely reduced carbocyclic group. The different optical modifications of the aldoses, namely, the dextro-, laevo-, meso-, and racemic modifications may be used in preparing this secondary sugar amine.
The diazoimino compound may then be mixed with one of the usual ice color coupling components. such as an arylamide 0f 2-3-hydroxynaphthoic acid, an arylamide of hydroxy-carbazoleor hydroxy-naphthocarbazole-carboxylic acid, an arylamide of hydroxy-anthracene-carboxylic acid, alphaor beta-naphthol, an acetoacetyl derivative of an arylamine, or phenylmethyl pyrazolone. It is to be understood that this mixture may contain one or more diazoimino compounds and. one or more ice color coupling components, since certain shades are obtained by using more than one and/or more than one ice color coupling component which could not be obtained otherwise.
The textile material is printed orimpregnated with this mixture, and then treated with an acid, preferably a weak acid at elevated to hydrolyze the diazoimino compound and permit coupling to take place between the regenerated diazo salt and the ice color coupling component. Acetic and/or formic acids have been found to give very satisfactory results but the invention is not limited to these acids since hydrolysis of the diazoimino compound may be effected by numerous other acids or mixtures of acids, well known to one skilled in the art. The acid or acids used in treating the printed or impregnated diazoimino compound temperatures, 1;.
textile material may be in either the liquid or vapor phase.
It is to be understood that the ice color coupling component or components and the diazolmino compound or compounds need not be applied to the textile material simultaneously, but one may be applied prior to the other, the resulting reaction being fundamentally the same regardless of the order in which the reactants are applied.
' It is also to be understood that when reference is made to a mixture of an ice color coupling component and a diazoimino compound this mixture may contain various assistants such as starch, gum, alkali, and Turkey red oil. The compositions of these printing and dyeing mixtures are so well known that nodifliculty should beencountered in selecting the proper assistantsfcr any given purpose, in the event that assistants are required.
The process described in the present disclosure produces excellent dyeings and prlntings on textile material in a much more simplified manner than was previously possible. The colors produced are exceptionally uniform and fast, due in great part to the thorough impregnation of the fibers with the very soluble diazoimino compound. No deleterious side reactions take place to impair the efliciency of the process and the appearance and properties of the products produced. The secondary sugar amine, produced upon hydrolysis of the diazoimino compound, does not have a strong reducing effect, consequently, it does not reduce the diazo salt or interfere in any manner with the coupling of this diazo salt and the ice color coupling component. The compounds used are readily available at a very reasonable cost, and in addition the simplification of the printing or dyeing processes results in an appreciable saving to the manufacturer.
As many apparently widely different embodiments of this invention may be made without departing from the spirit and scope thereof, it is to be understood that we do not limit ourselves to the foregoing examples or description except as indicated in the following claims.
We claim;
1. A process for coloring material which comprises treating the material with a mixture comprising an ice color coupling component and a diazoimino compound, produced by coupling a secondary sugar amine with a diazotized aromatic amine containing no water-solubilizin'g group, then developing the color by subjecting the treated material to the action of a weak acid at elevated temperatures.
2. A process for coloring material which comprises treating the material with a mixture comprising an ice color coupling component and a diazoimino compound having the following general formula:
in which Aryl represents the residue of an aromatic amine containing no water-solubilizing group, and Z represents the residue of a secondary sugar amine, then developing the color-by subjecting the treated material to the action of a weak acid, preferably at elevated temperatures.
3. A process for coloring material-which comprises treating the material with a mixture comprising an ice color coupling component and, a,
diazoimino compound having the following gen eral formula:
in which Aryl represents the residue-of an and-- amine which may have non-water-solubilizing groups substituted thereon, R represents an alkyl, aralkyl, or completely'reduced carbocyclic radical, and x represents one of the integers 2, 3, 4, then developing the color by subjecting the treat-' ed material to the action of a weak acid, preferably at elevated temperatures.
4. A process for coloring material which comprises treating the material with a mixture cornprising an ice color coupling component and a diazoimino compound having the following general formula: I
. ongononnomon in which Aryl represents the residue of an I arylamine of the benzene, diphenyl, naphthalene, diphenylamine, azobenzene, anthraquinone or carbazole series, which may have non-water-solu bilizing groups substituted thereon, It represents an alkyl, aralkyl, or completely reduced carbocyclic radical, and :z: represents one of the integers 2, 3, 4, then developing the color by sub- ,iecting the treated material to the action of a weak acid, preferably at elevated temperatures.
5. A process for coloring material which comprises treating'tl'ie material with a mixture comprising an ice color coupling component selected from the group consisting of arylamides of 2-3- hydroxy-naphthoic acid, arylamides of hydroxycarbazoleor hydroxy-naphthocarbazole-carboxylic acids, arylamides of hydroxy-anthracenecarboxylic acids, alphaor beta-naphthol, ace-, toacetyl derivatives of arylamines, and phenylmethyl-pyrazolone, and a diazoimino compound having the following general formula: 1%
in which Arylrepresents the residue of an aryl- 12g amine of the benzene, diphenyl, naphthalene, diphenylamine, azobenzene, anthraquinone, or carbazole series, which may have non-water-solubilizing groups substituted thereon, R represents an alkyl, arallryl, or completely reduced carbocyclic radical, and :2: represents one of the integers 2, 3, 4, then developing the color by subjecting the treated material to the action of a weak acid at elevated temperatures.
6. A process for coloring material which comprises treating the materlal with a mixture comprising an ice color coupling component selected from the group consisting of arylamides of 2-3- hydroxy-naphthoic acid, arylamides of hydroxycarbazoleor hydroxy-naphthocarbazole-carboxylic acids, arylamides of hydroxy-anthracenecarboxylic acids, alphaor beta-naphthol, acetoacetyl derivatives of arylamines, and phenylmethyl-pyrazolone, and a diazoimino compound having the following general formula:
ongononpomon or completely reduced diphenyl, naphthalene, diphenylamlne, azobenzene, anthraquinone, or carbanole series, which contains no water-solubilizing group but which may have substituted thereon members selected from the group consisting of halogen, alkyl, zoylamino; R represents an alkyl, aralkyl, or completely reduced carbocyclic radical, and :e represents one of the integers 2, 3, 4, then developing the color by subjecting the treated material to the action of a weak acid at elevated temperatures.
7. A process for coloring material which com-s prises treating the material with a mixture comprising an arylamide of z-s-hydroxy-naphtholc acid having the following general formula:
CONE-R in which R represents the residue of an arylamine of the benzene or naphthalene series which may have non-water-solubillzing groups substituted thereon, and a diazoimino compound having the following general formula:
12 ar r-mm-m omwnonnomoa in which Aryl represents the residue of an arylamine of the benzene or naphthalene series which may have substituted'thereon non-watersolubilizing groups, R represents an alkyl, aralkyl, carbocyclic radical, and :n represents one of the integers 2, 3, 4, then developing the color by subjecting the treated material to the action of an acid selected from the group consisting of acetic and formic acid, at elevated temperatures.
8. A process for coloring material which comprises treating the material with a mixture comprising an arylamide of 2-3-hydroxy-naphthoic acid having the following general formula:
OH x zi \Y in which x and Y represent hydrogen, halogen,
alkyl or alkoxy groups, and a diazoimino compound having the following general formula:
is Aryl-N=N-N cmwnommmon in which Aryl represents the residue of an arylamlne of the benzene series, which may have substituted thereon members selected from the class consisting of halogen, alkyl, alkoxy, nitro and benzoyl-amino groups, R represents an alkyl group, and :2: represents one of the integers 2, 3, 4, then developing the color by subjecting the treated material to the action ofan acid selected from the group consisting of acetic and formic acid, at elevated temperatures.
9; A composition of matter which comprises an ice color coupling component and a diazoimino compound having the following general formula:
in which Aryl represents the residue of an aromatic amine containing no water-solubilizing group, and Z represents the residue of a secondary sugar amine.
10. A composition of matter which comprises an ice color coupling component and a diazoimino compoundhaving the following general formula:
CHKCHOHhCHaOH in which Aryl represents the residue of an arylamine of the benzene, dlphenyl, naphthalene, diphenylamine, azobenzene, anthraquinone or carbazole series, which may have non-water-solubilizing groups substituted thereon, R represents an alkyl, aralkyl, or completely reduced carbocyclic radical, and :1: represents one of the integers 2. 3, 4. 106
12. A composition of matter which comprises an ice color coupling component selected from the group consisting of arylamides of 2-3-hydroxy-naphthoic acid, arylamides of hydroxyor hydroxy-naphthocarbazole-carboxylic acids, arylamides of hydroxy-anthracenecarboxylic acids, alphaor beta-naphtha], acetoacetyl derivatives of arylamines, and phenylmethyl-pyrazolone; and a diazoimino compound having the following general formula:
in which Aryl represents the residue of an an]- amine of the benzene, diphenyl, naphthalene, diphenylamine, azobenzene, anthraquinone or carbazole series, which may have non-water-solubilizing groups substituted thereo R represents an alkyl, aralkyl, or completely reduced carbocyclic radical, and :2: represents one of the integers 2, 3, 4.
13. A composition of matter which comprises an ice color coupling component selected from the group consisting of arylamides of 2-3-hydroxy-naphthoic acid, arylamides of hydro carbazoleor hydroxy-naphthocarbazole-car- ArylN=NN 1 cmwnormomon in which Aryl represents the residue of an andamine of the benzene, diphenyl, naphthalene, di-
' ing group but which may have substituted there- I duced carbocyclic radical,- and'a: represents one of the integers 2, 3, 4. v r
14. A composition of matter which comprises an arylamide of z-3-hydroxy naphthoic acid having the following general formula:
ONE-R in which R represents the residue of an arylamine of the benzene ornaphthalene series which may have non-water-solubilizing groups substituted thereon, and a diazoimino compound having the following general formula:
Aryl-N=N-N om(cnon),cmorr in which Aryl represents the residue of an arylamine of the benzene or naphthalene series which may have substituted thereon non-watersolubilizing groups, R represents an alkyl, aralkyl,
or. completely reduced carbocyclic radical, and :1: represents one of the integers 2, 3, 4.
15. A composition of matter which comprises an arylamide of 2-3-hydroxy-naphthoic acid having the following general formula:
in which X and Y represent hydrogen, halogen, alkyl or alkoxy groups, and a diazoimino compound having the following general formula:
/R Aryl-N=NN ormononnomon in which X represents hydrogenor an alkyl or alkoxy group.
MILES AUGUSTINUS DAHLEN. FRITHJOF ZWILIGMEYER.
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US1968879A true US1968879A (en) | 1934-08-07 |
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US1968879D Expired - Lifetime US1968879A (en) | Process for dyeing and printing |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2500093A (en) * | 1942-12-01 | 1950-03-07 | Francolor Sa | Textile printing paste comprising a diazoamino compound and a substituted benzothiazole |
-
0
- US US1968879D patent/US1968879A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2500093A (en) * | 1942-12-01 | 1950-03-07 | Francolor Sa | Textile printing paste comprising a diazoamino compound and a substituted benzothiazole |
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