US3516780A - Process for the production of water-insoluble azo-dyestuffs on textile material of cellulose fibers or protein fibers - Google Patents
Process for the production of water-insoluble azo-dyestuffs on textile material of cellulose fibers or protein fibers Download PDFInfo
- Publication number
- US3516780A US3516780A US768964A US3516780DA US3516780A US 3516780 A US3516780 A US 3516780A US 768964 A US768964 A US 768964A US 3516780D A US3516780D A US 3516780DA US 3516780 A US3516780 A US 3516780A
- Authority
- US
- United States
- Prior art keywords
- grams
- acid
- water
- strength
- bath
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 title description 25
- 239000004753 textile Substances 0.000 title description 17
- 238000000034 method Methods 0.000 title description 16
- 238000004519 manufacturing process Methods 0.000 title description 5
- 102000004169 proteins and genes Human genes 0.000 title description 4
- 108090000623 proteins and genes Proteins 0.000 title description 4
- 229920003043 Cellulose fiber Polymers 0.000 title description 3
- 239000000835 fiber Substances 0.000 title description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000007859 condensation product Substances 0.000 description 21
- 239000000306 component Substances 0.000 description 18
- 238000004043 dyeing Methods 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- -1 alkali metal salts Chemical class 0.000 description 9
- 235000011054 acetic acid Nutrition 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000005018 casein Substances 0.000 description 7
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 7
- 235000021240 caseins Nutrition 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 150000007524 organic acids Chemical class 0.000 description 7
- CXNVOWPRHWWCQR-UHFFFAOYSA-N p-chloro-o-methylaniline Natural products CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 6
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- QMXZSRVFIWACJH-UHFFFAOYSA-N 1-chloro-2,5-dimethoxybenzene Natural products COC1=CC=C(OC)C(Cl)=C1 QMXZSRVFIWACJH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005470 impregnation Methods 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
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- DRBLTDRGXNXHFZ-UHFFFAOYSA-N (2-methylphenyl)cyanamide Chemical class CC1=CC=CC=C1NC#N DRBLTDRGXNXHFZ-UHFFFAOYSA-N 0.000 description 1
- RSDQBPGKMDFRHH-MJVIGCOGSA-N (3s,3as,5ar,9bs)-3,5a,9-trimethyl-3a,4,5,7,8,9b-hexahydro-3h-benzo[g][1]benzofuran-2,6-dione Chemical compound O=C([C@]1(C)CC2)CCC(C)=C1[C@@H]1[C@@H]2[C@H](C)C(=O)O1 RSDQBPGKMDFRHH-MJVIGCOGSA-N 0.000 description 1
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-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
- JSCNDCWUFHAJQL-UHFFFAOYSA-N 2-hydroxy-9h-carbazole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=C(O)C(C(=O)O)=C2 JSCNDCWUFHAJQL-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- PHQKCVOZVPSTAF-UHFFFAOYSA-N 3-hydroxyanthracene-2-carboxylic acid Chemical compound C1=CC=C2C=C(C=C(C(C(=O)O)=C3)O)C3=CC2=C1 PHQKCVOZVPSTAF-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
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical class NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-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
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-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
- RSDQBPGKMDFRHH-UHFFFAOYSA-N Taurin Natural products C1CC2(C)C(=O)CCC(C)=C2C2C1C(C)C(=O)O2 RSDQBPGKMDFRHH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical class ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 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
- SHLTXWFNRJQZTQ-UHFFFAOYSA-N n-chloro-2-methylaniline Chemical class CC1=CC=CC=C1NCl SHLTXWFNRJQZTQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229920006297 regenerated protein fiber Polymers 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000003245 working effect 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
- 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
- D06P1/02—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 azo dyes
- D06P1/12—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 azo dyes prepared in situ
- D06P1/127—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 azo dyes prepared in situ using a stabilised diazo component, e.g. diazoamino, anti-diazotate or nitrosamine R-N=N-OK, diazosulfonate, hydrazinesulfonate, R-N=N-N-CN
Definitions
- arylamides of 2,3-hydroxynaphthoic acid in the form of their alkali metal salts can be printed on cellulose fibers together with antidiazotates from aromatic amines, they are then dried, and the dyestuff can be developed by a hot acid-salt passage or by exposing the treated material to air. It has already been proposed to pad cellulose fabrics with mixtures from alkali metal salts of 2,3-hydroxynaphthoic acid arylamides and antidiazotates, to dry them and to cause the coupling by a treatment with acid-salt solutions.
- the process of the invention is carried out by treating the textile material in the form of yarn in hanks, wound bodies, combed or loose material in an alkaline bath which contains an azo component having a high substantivity, an antidiazotate and a wetting or dispersing agent and, if desired, an inorganic salt, for example sodium chloride or sodium sulfate.
- the treatment is carried out in the course of at least 10 minutes so that the azo com ponent can be fixed sufficiently and uniformly on the tex- 3,516,780. Patented June 23, 1970 ice tile material.
- it is advantageous to operate at room tem perature or at a moderately elevated temperature, preferably below 35 C.
- an organic acid for example formic acid, acetic acid, tartaric acid, citric acid, lactic acid or glycolic acid or a mixture of said acids or even a mixture of an inorganic acid, for example hydrochloric acid or sulfuric acid with an organic acid is added to the bath in such a quantity that the total quantity of alkali metal is neutralized in the bath and on the textile material and a pH value between about 4 and 7 is attained, the temperature being below 40 C.
- the dyestulf is produced on the textile material.
- the treated material is then Washed in a neutral or acid bath, if desired in the presence of dispersing agents, and the dyeing is finished in the usual manner.
- Dyeings are obtained which possess an excellent fastness to rubbing.
- Piecegoods can be dyed by impregnating the goods on a padding machine with two or several rollers with a mixture of the azo component and an excess of antidiazotate, and rolling them up, and after a retention period of 30 minutes for example, the coupling is caused by passing the treated goods through an organic acid, a mixture of organic acids or a mixture of organic and inorganic acids at a temperature below 40 C.
- This process can also be performed by a passage through a compartment of a roller vat or by several passages on a jig or on a winch vat, whereby additions of inorganic salts and dispersing agents sometimes show an excellent effect in the impregnating and developing stage.
- the concentration of the azo component in the initial bath must be lowered in comparison with that of the feeding bath, whereas the concentration of the antidiazotate in the initial bath is not lowered in comparison with that of the feeding bath, when operating according to the afore-mentioned work ing method.
- the concentration of the azo component in the initial bath must be lowered in comparison with that of the feeding bath, whereas the concentration of the antidiazotate in the initial bath is not lowered in comparison with that of the feeding bath, when operating according to the afore-mentioned work ing method.
- azo components in the process of the present invention compounds enter into consideration which are dis: tinguished by a high substantivity for the textile material used, i.e. azo components which at a long goods-to-liquor ratio of 1:20, a duration of the dyeing of 30 minutes at 30 C., a concentration of 1 g. per liter of water without the addition of salts and an excess of 4.5 grams of sodium hydroxide per liter of the bath, possess such a high substantivity that at least 9 grams are absorbed by 1000 grams of cotton.
- a high substantivity for the textile material used i.e. azo components which at a long goods-to-liquor ratio of 1:20, a duration of the dyeing of 30 minutes at 30 C., a concentration of 1 g. per liter of water without the addition of salts and an excess of 4.5 grams of sodium hydroxide per liter of the bath, possess such a high substantivity that at least 9 grams are absorbed by 1000 grams of cotton.
- Suitable compounds are for example: 2,3-hydroxynapthoylamino-benzols, such as 1-(2,3'-hydroxynaphthoylamino)-2,5-dimethoxy-4- chlorobenzene or 1-(2,3'-hydroxynaphthoylamino)-2-methoxy-4-chloro- S-methylbenzene;
- 6-bromoor 6-methoxy-2,3-hydroxynaphthoic acid arylamides such as 1- 6-bromo-2,3 -hyd roxynaphthoylamino) -2-methoxybenzene;
- 2-hydroxy-anthracene-3-carboxylic acid arylamides such 1-(2'-hydroxy-anthracene-3'-carboylamino)-2-methylbenzene;
- 2-hydroxycarbazol-3-carboxylic acid arylamides such as 1-(2-hydroxycarbazol-3'-carboylamino) -4-chlorobenzene;
- 5-hydroxy-1,2,1',2'-benzocarbazol-4-carboxylic acid arylamides such as 1-(5'-hydroxy-l',2,1",2"benzocarbazol-4-carboylamino)-4-methoxybenzene or 1-(5'-hydroxy-1',2',1",2"-benzocarbazol-4-carboylamino) -2-methyl-4-methoxybenzene;
- terephthaloyl-bis-acetic acid arylamides such as terephthaloyl-bis-( 1-acetylamino-2,4-dimethoxy-S- chlorobenzene) or terephthaloyl-bis- 1-acetylamino-2-methoxy-4-chloro- S-methylbenzene)
- antidiazotates particularly those from aromatic amines enter into consideration, for example from monochloranilines and dichloranilines, toluidines, chlorotoluidines, chloranisidines, xylidines, phenetidines, nitranilines, nitrotoluidines, nitranisidines, nitroxylidines, nitrophenetidines, cyanotoluidines, cyananisidines, aminobenzenesulfonic acid amides, benzidine, dianisidine or tolidine.
- the compounds used in ice-color technique enter into consideration, for example condensation products of high molecular weight fatty acids and protein degradation products, condensation products of high molecular weight fatty acids and aminoalkyl-sulfonic acids, condensation products of formaldehyde with naphthalene-sulfonic acids or purified sulfite cellulose waste liquor.
- the process of the present invention can be carried out on textile material of natural or regenerated cellulose, cyano-ethylated cellulose, Wool, natural silk or regenerated protein fibers.
- the process of the present invention represents an essential simplification.
- the dyebath is discharged after the impregnation with the azo component, the fabric is centrifuged, filtered with suction or subjected to an intermediate rinsing, and the dyestuif is developed in a second bath with a diazonium compound.
- the process of the present invention includes the impregnation and developing stage in one bath, and after a period which is necessary for fixing the azo component the coupling takes place without any interposed operation, so that the duration of such a dyeing process is essentially reduced.
- Example 1 A cross-wound bobbin with 500 grams of cotton yarn is wetted out on a cheese dyeing machine and treated in a bath containing in 6.5 liters of water of 20 C., 3.2 grams of a condensation product of palm-kernel fatty acid chloride and partially decomposed lactic casein, 1.6 grams of a condensation product of u-ethylhexyl-chlorocarbonic acid ester and ot-ethylhexyl-taurin, 6 grams of sodium ethylene-diaminotetracetate of 50% strength, 48 cc. of sodium hydroxide solution of 38 B.
- Example 2 1000 grams of cotton yarn are treated at a goods-toliquor ratio of 1:20 at 30 C. in a bath which contains in 20 liters of water 9.6 grams of a condensation product of palm-kernel fatty acid chloride and partially decomposed lactic casein, 4.8 grams of a condensation product of a-ethylhexyl-chlorocarbonic acid ester and a-ethylhexyltaurin, 200 cc.
- Example 3 1000 grams of cotton yarn are treated at a goods-toliquor ratio of 1:20 at 20 C. in a bath WhlCh contains in 20 liters of water 9.6 grams of a condensation product of palm-kernel fatty acid chloride and partially decomposed lactic casein, 4.8 grams of a condensation product of u-ethylhexyl-chlorocarbonic acid ester and (J -ethylhexyl-taurin, 140 cc.
- Example 4 1000 grams of cotton yarn are treated at 20 C. in the following bath: 20 liters of cold Water are mixed with 20 grams of sodium ethylene-diaminotetracetate of 50% strength, 9.6 grams of a condensation product of palmkernel fatty acid chloride and partially decomposed lactic casein, 4.8 grams of a condensation product of a-ethylhexyl-chlorocarbonic acid ester and u-ethylhexyl-taurin, 120 cc. of sodium hydroxide solution of 38 B., 400 grams of sodium chloride, 44.5 g.
- Example 5 1000 grams of cotton yarn are treated at 20 C. in the following lbath: 20 liters of cold water are mixed with 9.6 grams of a condensation product of palm-kernel fatty acid chloride and partially decomposed lactic casein, 4.8 grams of a condensation product of u-ethylhexyl-chlorocarbonic acid ester and a-ethylhexyl-taurin, 160 cc.
- Example 6 kilograms of a cotton fabric are impregnated on the padding machine at an immersion period of 0.65 second and a squeezing effect of 60% with a solution of 30 C. which contains in the initial bath 8 grams of 2- (2',3'-hydroxynaphthoylamino)-napthalene, 1.3 grams of a condensation product of palm-kernal fatty acid chloride and partially decomposed lactic casein, 0.6 gram of a condensation product of a-ethylhexyl-chlorocarbonic acid ester and a-ethylhexyl-taurin, 14 cc.
- a process for the production of water-insoluble azodyestuffs on textile materials of cellulose or protein fibers comprising treating the textile material at a long goodsto-liquor ratio in an alkaline bath containing (1) a coupling component highly substantive for the material to be dyed and selected from the group consisting of arylamides of aromatic ortho-hydroxy carboxylic acids, ary1- amides of heterocyclic ortho-hydroxy carboxylic acids and arylamides of acyl acetic acids, (2) an antidiazotate from a primary aromatic amine and (3) an anionic dispersing agent, for a time sufficient to absorb and level the coupling component on the textile material and thereafter, without intermediate drying, adding to the alkaline bath an acid agent selected from the group consisting of an organic acid and a mixture of an organic acid with an inorganic acid at a temperature below 40 C., said acid agent being added in an amount sufficient to neutralize the total quantity of alkaline material and to obtain a pH of from 4 to 7 on the textile material.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF39573A DE1248009B (de) | 1963-04-24 | 1963-04-24 | Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial ausCellulose- oder Eiweissfasern |
| BE647093A BE647093A (enrdf_load_stackoverflow) | 1963-04-24 | 1964-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3516780A true US3516780A (en) | 1970-06-23 |
Family
ID=25655856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US768964A Expired - Lifetime US3516780A (en) | 1963-04-24 | 1968-10-10 | Process for the production of water-insoluble azo-dyestuffs on textile material of cellulose fibers or protein fibers |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3516780A (enrdf_load_stackoverflow) |
| BE (1) | BE647093A (enrdf_load_stackoverflow) |
| NL (1) | NL6404555A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3961886A (en) * | 1973-09-15 | 1976-06-08 | Hoechst Aktiengesellschaft | Process for the dyeing and printing of cellulose-containing textile materials |
| US4094637A (en) * | 1974-10-19 | 1978-06-13 | Hoechst Aktiengesellschaft | Process for the printing with developing dyes |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1882560A (en) * | 1928-05-07 | 1932-10-11 | Gen Aniline Works Inc | Manufacture of water-insoluble azo dyestuffs |
| US1882561A (en) * | 1929-02-25 | 1932-10-11 | Gen Aniline Works Inc | Dyeing preparation |
| US2088506A (en) * | 1934-04-06 | 1937-07-27 | Du Pont | Process and composition for applying and fixing diazoimino dyestuffs |
| US2926986A (en) * | 1960-03-01 | Solutions of diazoamino derivatives |
-
1964
- 1964-04-24 BE BE647093A patent/BE647093A/xx unknown
- 1964-04-24 NL NL6404555A patent/NL6404555A/xx unknown
-
1968
- 1968-10-10 US US768964A patent/US3516780A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2926986A (en) * | 1960-03-01 | Solutions of diazoamino derivatives | ||
| US1882560A (en) * | 1928-05-07 | 1932-10-11 | Gen Aniline Works Inc | Manufacture of water-insoluble azo dyestuffs |
| US1882561A (en) * | 1929-02-25 | 1932-10-11 | Gen Aniline Works Inc | Dyeing preparation |
| US2088506A (en) * | 1934-04-06 | 1937-07-27 | Du Pont | Process and composition for applying and fixing diazoimino dyestuffs |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3961886A (en) * | 1973-09-15 | 1976-06-08 | Hoechst Aktiengesellschaft | Process for the dyeing and printing of cellulose-containing textile materials |
| US4094637A (en) * | 1974-10-19 | 1978-06-13 | Hoechst Aktiengesellschaft | Process for the printing with developing dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6404555A (enrdf_load_stackoverflow) | 1964-10-26 |
| BE647093A (enrdf_load_stackoverflow) | 1964-10-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4260389A (en) | Finishing process | |
| US3049446A (en) | Process for the manufacture of urea, glyoxal and formaldehye reaction product useful for improving cellulosic textile materials | |
| US3211514A (en) | Process for dyeing and printing netrugen-containhng fibers | |
| US3516780A (en) | Process for the production of water-insoluble azo-dyestuffs on textile material of cellulose fibers or protein fibers | |
| US3900283A (en) | Process for the dyeing of materials consisting of anion-modified polyacrylonitrile, polyamide and polyester fibres | |
| US3713767A (en) | Process for the dyeing of textile material of mixtures of polyester fibers and cellulose fibers | |
| US2272810A (en) | Printing cellulosic textile materials | |
| US2095600A (en) | Process for the production of fast tints on the fiber | |
| US2078388A (en) | Dyeing process and composition | |
| US4289496A (en) | Finishing process | |
| US3441364A (en) | Process for the production of water-insoluble azo dyestuffs on textile material comprising cellulose or protein fibers | |
| US3787179A (en) | Process for the manufacture of insoluble azo dyestuffs on cellulose fibers | |
| US2263387A (en) | Process of dyeing | |
| US2317756A (en) | Process for improving materials containing cellulose | |
| US3697216A (en) | Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers | |
| US4110071A (en) | Process for the tone-in-tone printing and pad-dyeing of textile material made from fibre mixtures | |
| US3679350A (en) | Process for the dyeing of textile materials made from mixtures of polyester and cellulosic fibres | |
| US3961887A (en) | Process for the printing of cellulose containing textile material | |
| US3708257A (en) | Process for the dyeing of textile material made from mixtures of polyester and cellulosic fibers | |
| US2448515A (en) | Dyed cellulose ethers and dyeing of fabrics therewith | |
| US3484181A (en) | Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers | |
| US3254934A (en) | Process for the coloring of hydrophobic materials | |
| US5174791A (en) | Process for dyeing and printing blend fabrics of polyester and natural fibre materials with disperse dye and polyether-polyester to inhibit soilins with disperse dye | |
| US4235596A (en) | Process for the pad-dyeing and printing of textile material made from mixed fibres of cellulose and polyester | |
| US3502424A (en) | Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers |