US3697216A - Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers - Google Patents
Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers Download PDFInfo
- Publication number
- US3697216A US3697216A US114387A US3697216DA US3697216A US 3697216 A US3697216 A US 3697216A US 114387 A US114387 A US 114387A US 3697216D A US3697216D A US 3697216DA US 3697216 A US3697216 A US 3697216A
- Authority
- US
- United States
- Prior art keywords
- bath
- hydroxynaphthoylamino
- textile material
- grams
- cellulose
- 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 abstract description 34
- 238000000034 method Methods 0.000 title abstract description 23
- 239000004753 textile Substances 0.000 title abstract description 23
- 239000000835 fiber Substances 0.000 title abstract description 19
- 229920002678 cellulose Polymers 0.000 title abstract description 14
- 239000001913 cellulose Substances 0.000 title abstract description 14
- 102000004169 proteins and genes Human genes 0.000 title abstract description 9
- 108090000623 proteins and genes Proteins 0.000 title abstract description 9
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 150000001989 diazonium salts Chemical class 0.000 abstract description 25
- 238000005470 impregnation Methods 0.000 abstract description 18
- 239000002270 dispersing agent Substances 0.000 abstract description 14
- 239000011230 binding agent Substances 0.000 abstract description 11
- 150000004982 aromatic amines Chemical class 0.000 abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000004043 dyeing Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 239000007859 condensation product Substances 0.000 description 14
- 239000003513 alkali Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- -1 heterocyclic amines Chemical class 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 9
- 239000000080 wetting agent Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000009736 wetting Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 235000018102 proteins Nutrition 0.000 description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 6
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 6
- 239000005642 Oleic acid Substances 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000011928 denatured alcohol Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 239000008234 soft water Substances 0.000 description 3
- QMXZSRVFIWACJH-UHFFFAOYSA-N 1-chloro-2,5-dimethoxybenzene Natural products COC1=CC=C(OC)C(Cl)=C1 QMXZSRVFIWACJH-UHFFFAOYSA-N 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- QGZGJNPVHADCFM-UHFFFAOYSA-N 3-hydroxy-n-naphthalen-1-ylnaphthalene-2-carboxamide Chemical compound C1=CC=C2C(NC(=O)C3=CC4=CC=CC=C4C=C3O)=CC=CC2=C1 QGZGJNPVHADCFM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 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
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- CXNVOWPRHWWCQR-UHFFFAOYSA-N p-chloro-o-methylaniline Natural products CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- DRBLTDRGXNXHFZ-UHFFFAOYSA-N (2-methylphenyl)cyanamide Chemical class CC1=CC=CC=C1NC#N DRBLTDRGXNXHFZ-UHFFFAOYSA-N 0.000 description 1
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- OACCRGFGCIQFNR-UHFFFAOYSA-N 1-chloro-2,4-dimethoxybenzene Chemical compound COC1=CC=C(Cl)C(OC)=C1 OACCRGFGCIQFNR-UHFFFAOYSA-N 0.000 description 1
- SDGMUBWPXBSKCT-UHFFFAOYSA-N 1-chloro-4-methoxy-2-methylbenzene Chemical compound COC1=CC=C(Cl)C(C)=C1 SDGMUBWPXBSKCT-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-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
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-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
- CXYMDAXGGAITQP-UHFFFAOYSA-N 2-hydroxy-n-phenylnaphthalene-1-carboxamide Chemical compound OC1=CC=C2C=CC=CC2=C1C(=O)NC1=CC=CC=C1 CXYMDAXGGAITQP-UHFFFAOYSA-N 0.000 description 1
- PFRYFZZSECNQOL-UHFFFAOYSA-N 2-methyl-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC=CC=2)C)=C1 PFRYFZZSECNQOL-UHFFFAOYSA-N 0.000 description 1
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-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
- 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
- WBGVVXSCGNGJFL-UHFFFAOYSA-N 3-amino-n,n-diethyl-4-methoxybenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(OC)C(N)=C1 WBGVVXSCGNGJFL-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-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
- 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
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-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
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- WLJSUJOESWTGEX-UHFFFAOYSA-N 5-chloro-2-(4-chlorophenoxy)aniline Chemical compound NC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1 WLJSUJOESWTGEX-UHFFFAOYSA-N 0.000 description 1
- YJKJAYFKPIUBAW-UHFFFAOYSA-N 9h-carbazol-1-amine Chemical class N1C2=CC=CC=C2C2=C1C(N)=CC=C2 YJKJAYFKPIUBAW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 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 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-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
- AUQLBXGRHXRGCX-UHFFFAOYSA-N n-(2-hydroxyphenyl)naphthalene-1-carboxamide Chemical class OC1=CC=CC=C1NC(=O)C1=CC=CC2=CC=CC=C12 AUQLBXGRHXRGCX-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
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229920006297 regenerated protein fiber Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/12—Preparing azo dyes on the material
Definitions
- the present invention relates to a process for the production of water-insoluble azo dyestuffs on textile materialof cellulose or protein fibers.
- 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, woven or knitted fabrics in an alkaline bath containing an azo component having a high substantivity, an excess amount of alkali, a wetting or dispersing agent or a mixture of dispersing agents and, if resired, an inorganic salt, for example sodium chloride, sodium sulfate or trisodium phosphate.
- the treatment is carried out for at least 10 to 20 minutes so that the azo component can be sufliciently and uniformly fixed on the textile material. Generally, this operation is carried out at room temperature or at a slightly elevated temperature, suitably at a temperature below 35 C. If a material is to be treated that can be dyed through with difficulty only, it is possible to start with a temperature near boiling temperature of the bath and to allow the temperature to descend to approximately 20 to 30 C.
- azo components in the process of the present invention compounds may be used which are distinguished by a high substantivity for the textile material used, i.e. azo components which, at a goods-to-liquor ratio of 1:20, an impregnating period of 30 minutes at 30 C., a concentration of 1 gram per liter of water without the addition of a salt and an excess of 4.5 grams of sodium hydroxide per liter of bath, possess such high substantivity that at least 9 grams are absorbed by 1 kilogram of the material to be dyed.
- a high substantivity for the textile material used i.e. azo components which, at a goods-to-liquor ratio of 1:20, an impregnating period of 30 minutes at 30 C., a concentration of 1 gram per liter of water without the addition of a salt and an excess of 4.5 grams of sodium hydroxide per liter of bath, possess such high substantivity that at least 9 grams are absorbed by 1 kilogram of the material to be dyed.
- Suitable compounds are, for example, 2,3 hydroxynaphthoylaminobenzenes, eg 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, e.g.
- textile material by which the substantive azo components are more completely absorbed than by cotton for example textile material of viscose staple fibers or mercerized cotton
- azo components also 1-(2',3-hydroxynaphthoylamino)-naphthalene, 1-(2,3-hydroxynaphthoylamino) 2 methyl-4- chlorobenzene, 1-(2',3' hydroxynaphthoylamino)-2,4-dimethoxy-S-chlorobenzene or 1-(2',3' -hydroxynaphthoy1- amino)-2-methoxy-5-chlorobenzene.
- the compounds commonly used in the ice-color technique enter into consideration, for example condensation products of high molecular weight fatty acids and protein decomposition 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, or mixtures of these compounds. Moreover, they may still be added further highly effective wetting agents, for example alkylaryl sulfonates.
- the diazonium compound and the alkali binding agent in the form of an aqueous solution concentrated in a higher or lesser degree, are added to the impregnation bath, and the treatment is continued.
- diazonium compounds particularly those from aromatic mono and diamines enter into consideration, for example those from monochloranilines and dichloranilines, toluidines, chlorotoluidines, chloranisidines, phenetidines, nitranilines, nitrotoluidines, nitroanisidines, nitroxylidines, nitrophenetidines, cyanotoluidines, cyanoanisidines, aminobenzene-sulfonic acid amides, aminophenyl-alkylsulfones, aminobenzene carboxylic acid amides, aminodiphenyl ethers, monoacylated phenylenediamines, amino-azobenzenes, benzidine, dianisidine and toluidine as well as from heterocyclic amines, e.g. aminocarbazoles.
- alkali binding agents which are added tothe impregnation bath together with the diazonium compound and which serve to neutralize the excess amount of alkali
- inorganic acids for example hydrochloric acid, sulfuric acid or phosphoric acid
- organic acids for example acettic acid or formic acid
- acid alkali metal salts for example mono-sodium phosphate and acid sodium sulfate.
- the aqueous solution containing the diazonium compound and the alkali binding agent may additionally contain further dispersing agents. These dispersing agents promote the fine division of the dyestutf pigment which is formed when stirring the diazo solution into the impregnation bath.
- condensation products of high molecular weight fatty acids and aminoalkyl sulfonic acids condensation products of formaldehyde with naphthalene-sulfonic acids and purified sulfite cellulose waste liquor.
- the amount to be used of the diazonium compound capable of coupling depends on the amount applied of the azo component.
- Thev diazonium compound is advantageously applied in an amount which exceeds the stoichiometric proportion, i.e. approx. 30 to 200 percent, calculated on the azo component.
- the alkali binding agents which are simultaneously added together with the diazonium compound are used in such an amount that in the bath a pH-value of approximately 3 to 8, preferably approximately 4.5 to 6.5 is attained.
- the dyeing liquor is allowed to act upon the material for a further 10 to 30 minutes to assure complete coupling and penetration of the material to be dyed.
- the material is then rinsed, washed with effective dispersing agents, and the dyeing is finished in the usual manner. Full dyeings are obtained which possess an unexpectedly good fastness to rubbing.
- the process of the present invention can be applied to textile material of natural or regenerated cellulose, cyanoethylated cellulose, wool, natural silk or regenerated protein fibers.
- the process of the present invention is distinguished in that working stage II (removal of the residual azo component not absorbed on the fiber) is omitted and for working stage III (developing with the diazonium compound) the preparation of a fresh developing bath is no longer necessary.
- EXAMPLE 1 1 kilogram of cotton hank was treated in a bath of 25 C. containing, in 20 liters of soft water, 40 grams of purified sulfite cellulose waste liquor, 10 grams of the sodium salt of ethylenediamine-tetracetic acid and 149 cc. of sodium hydroxide solution of 32.5% strength as well as 26 grams of 1-(2',3'-hydroxynaphthoylamino)-2,5-dimethoxy-4-chlorobenzene, dissolved in 39 cc. of denatured alcohol, 11 cc. of sodium hydroxide solution of 32.5% strength, 52 cc. of water of 40 C. and 20 cc. of formaldehyde of 33% strength.
- the solution of a diazonium salt prepared from 20.6 grams of l-amino- 2-methyl-5-chlorobenzene and 10 grams of a condensation product of oleic acid and methyl-taurine in 300 cc. of acetic acid of 50% strength was introduced into the impregnation bath, whereby a pH of 5-6 was attained in the bath and the dyestuff was formed on the textile material. Then the treatment of the material was continued at 25 C. for a further 20 minutes, and after having rinsed with water, the dyeing was treated for 15 minutes in a fresh bath of 60 C.
- the after-treatment can also be carried out with the addition of 3 grams/liter of a mixture of 63% of perchloroethylene, 17% of a reaction product of 10 moles of ethylene oxide per 1 mol of nonyl phenol and 20% of isopropanol.
- EXAMPLE 2 A cross-wound bobbin of 500 grams of cotton yarn was treated in a dyeing machine having a capacity of approximately 6 liters and in which the direction of circulation of the bath was'being changed, with a solution of 20 C. containing, in 6 liters of water, 12 grams of purified sulfite cellulose waste liquor, 3 grams of a condensation product of oleic acid and methyl-taurine and 42 cc. of sodium hydroxide solution of 32.5% strength, as well as 12 grams of 2 (2',3-hydroxynaphthoylamino)-3- methoxy-diphenyleneoxide, dissolved in 24 cc. of denatured alcohol and 6 cc.
- alkali binding agent instead of 192 grams of mono-sodium phosphate, a mixture of 26 cc. of hydrochloric acid of 32% strength and 45 cc. of acetic acid of 50% strength.
- EXAMPLE 3 1 kilogram of natural silk was treated, at a goods-toliquor ratio of 1:20, in a bath of 25 C. containing, in 20 liters of soft water, grams of a condensation product of oleic acid and methyl-taurine, 40 grams of a dispersing agent containing 16 percent of a condensation product of partially decomposed casein and palm-kernel fatty acid and 8% of a condensation product of a-ethylhexyl-chlorocarbonic acid ester and sodium a-ethylhexyl-taurate, and
- the bath was allowed to circulate for a further 40 minutes, the liquor was discharged and then the silk was rinsed and washed for 15 minutes with a liquor of 60 C. containing 1 gram/liter of a condensation product of oleic acid and methyl-taurine. Subsequently, the dyed silk was again rinsed and dried. A full red dyeing was obtained having good properties of fastness.
- EXAMPLE 4 l kilogram of viscose staple fiber was treated, at a goods-to-liquor ratio of 1:20, in a bath of 25 C. containing, in 20 liters of soft water, 10 grams of a condensation product of oleic acid and methyl-taurine, 40 grams of purified sulfite cellulose waste liquor and 74 cc. of sodium hydroxide solution of 32.5% strength as well as 12 grams of 1-(2',3'-hydroxy-naphthoylamino)- naphthalene, dissolved in 18 cc. of denatured alcohol, 6 cc. of sodium hydroxide solution of 32.5% strength, 18 cc. of water and 12 cc.
- alkali binding agent is an inorganic or organic acid, an acid alkali metal salt or mixtures thereof.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052448 | 1967-05-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3697216A true US3697216A (en) | 1972-10-10 |
Family
ID=7105458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US114387A Expired - Lifetime US3697216A (en) | 1967-05-18 | 1971-02-10 | Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers |
Country Status (7)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082503A (en) * | 1975-08-05 | 1978-04-04 | Hoechst Aktiengesellschaft | Process for the production of water-insoluble azo dyestuffs on the fiber |
| US4183727A (en) * | 1976-06-05 | 1980-01-15 | Hoechst Aktiengesellschaft | Process for the production of water-insoluble azo dyestuffs on the fiber |
| US4318848A (en) * | 1977-01-05 | 1982-03-09 | Bayer Aktiengesellschaft | Process for the neutralization of basic reaction compositions |
-
1968
- 1968-05-01 NL NL6806152A patent/NL6806152A/xx unknown
- 1968-05-15 GB GB23111/68A patent/GB1189243A/en not_active Expired
- 1968-05-16 CH CH724168D patent/CH724168A4/xx unknown
- 1968-05-16 CH CH724168A patent/CH505249A/de not_active IP Right Cessation
- 1968-05-16 AT AT471568A patent/AT280203B/de not_active IP Right Cessation
- 1968-05-20 BE BE715422D patent/BE715422A/xx unknown
- 1968-05-20 FR FR1565972D patent/FR1565972A/fr not_active Expired
-
1971
- 1971-02-10 US US114387A patent/US3697216A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082503A (en) * | 1975-08-05 | 1978-04-04 | Hoechst Aktiengesellschaft | Process for the production of water-insoluble azo dyestuffs on the fiber |
| US4183727A (en) * | 1976-06-05 | 1980-01-15 | Hoechst Aktiengesellschaft | Process for the production of water-insoluble azo dyestuffs on the fiber |
| US4318848A (en) * | 1977-01-05 | 1982-03-09 | Bayer Aktiengesellschaft | Process for the neutralization of basic reaction compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CH505249A (de) | 1970-12-15 |
| DE1619527B2 (de) | 1975-12-11 |
| BE715422A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-11-20 |
| FR1565972A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-05-02 |
| DE1619527A1 (de) | 1971-03-11 |
| AT280203B (de) | 1970-04-10 |
| NL6806152A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-11-19 |
| CH724168A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-15 |
| GB1189243A (en) | 1970-04-22 |
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