US3484181A - 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
- US3484181A US3484181A US433783A US43378365A US3484181A US 3484181 A US3484181 A US 3484181A US 433783 A US433783 A US 433783A US 43378365 A US43378365 A US 43378365A US 3484181 A US3484181 A US 3484181A
- Authority
- US
- United States
- Prior art keywords
- acid
- bath
- hydroxynaphthoylamino
- amino
- water
- 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
- 238000000034 method Methods 0.000 title description 22
- 239000000463 material Substances 0.000 title description 21
- 239000004753 textile Substances 0.000 title description 17
- 239000000835 fiber Substances 0.000 title description 9
- 229920002678 cellulose Polymers 0.000 title description 7
- 239000001913 cellulose Substances 0.000 title description 7
- 102000004169 proteins and genes Human genes 0.000 title description 6
- 108090000623 proteins and genes Proteins 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 diazoamino compound Chemical class 0.000 description 42
- 239000002253 acid Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 230000008878 coupling Effects 0.000 description 21
- 238000010168 coupling process Methods 0.000 description 21
- 238000005859 coupling reaction Methods 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 238000004043 dyeing Methods 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 159000000000 sodium salts Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000007859 condensation product Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 7
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 7
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 7
- 239000005642 Oleic acid Substances 0.000 description 7
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 description 7
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 7
- 239000011707 mineral Substances 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application 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
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 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
- 238000001035 drying Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- 239000000080 wetting agent 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
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 2
- HGMGPNYETDBNFG-UHFFFAOYSA-N 4-(ethylamino)benzenesulfonic acid Chemical compound CCNC1=CC=C(S(O)(=O)=O)C=C1 HGMGPNYETDBNFG-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 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
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 235000011008 sodium phosphates Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000004964 sulfoalkyl group Chemical group 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- ZDSCFBCGDDCJFZ-UHFFFAOYSA-N 2-(methylamino)ethanesulfonic acid;sodium Chemical compound [Na].CNCCS(O)(=O)=O ZDSCFBCGDDCJFZ-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- TXPKUUXHNFRBPS-UHFFFAOYSA-N 3-(2-carboxyethylamino)propanoic acid Chemical compound OC(=O)CCNCCC(O)=O TXPKUUXHNFRBPS-UHFFFAOYSA-N 0.000 description 1
- INCJNDAQNPWMPZ-UHFFFAOYSA-N 3-amino-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1N INCJNDAQNPWMPZ-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
- QRAXZXPSAGQUNP-UHFFFAOYSA-N 4-(methylamino)benzenesulfonic acid Chemical compound CNC1=CC=C(S(O)(=O)=O)C=C1 QRAXZXPSAGQUNP-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-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
- 241001584775 Tunga penetrans Species 0.000 description 1
- VFINORKTHQRPLO-UHFFFAOYSA-N [4-(2-ethylbenzimidazol-1-yl)piperidin-1-yl]-(5-methoxy-1h-indol-2-yl)methanone Chemical compound COC1=CC=C2NC(C(=O)N3CCC(CC3)N3C4=CC=CC=C4N=C3CC)=CC2=C1 VFINORKTHQRPLO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- HZBLLTXMVMMHRJ-UHFFFAOYSA-L disodium;sulfidosulfanylmethanedithioate Chemical compound [Na+].[Na+].[S-]SC([S-])=S HZBLLTXMVMMHRJ-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SHLTXWFNRJQZTQ-UHFFFAOYSA-N n-chloro-2-methylaniline Chemical class CC1=CC=CC=C1NCl SHLTXWFNRJQZTQ-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 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
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229920006297 regenerated protein fiber Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- the present invention provides a process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers.
- water-insoluble azo dyestuffs can be produced on textile material of cellulose or protein fibers by treating the textile material in an alkaline bath which contains a coupling component and a diazoamino compound of the Formula 1 Alk in which R represents phenyl, halogenophenyl, alkylphenyl, alkoxyphenyl, dialkylphenyl, alkylhalogenophenyl, alkoxyhalogenophenyl, alkylcarbamylphenyl, alkoxycarbamylphenyl, alkylsulfamylphenyl, alkoxsulfamylphenyl, alkyl(alkylor aralkyl-sulfonyl) phenyl, alkoxy (alkylor aralkyl-sulfonyl) phenyl or acylaminophenyl, Alk represents lower straight or branched chain alkyl which may be substituted by carboxyl, and R represents carb
- the process of the present invention is carried out by treating the textile material in the form of yarn hanks, wound bodies, slubbings or piece goods in an alkaline bath which contains a coupling component having high substantivity and a diazo-amino compound of the indicated composition as Well as a wetting or dispersing 3,484,181 Patented Dec. 16, 1969 agent and, if desired, a mineral salt, for example, sodium chloride, sodium phosphate or sodium sulfate.
- the treatment is carried out for at least 10 minutes in order to ensure that the coupling component is sufficiently and uniformly fixed onto the textile material.
- the process is carried out at temperatures between about 10 and about 35 C., suitably at room temperature or at a slightly elevated temperature.
- an organic acid for example, formic acid, acetic acid, tartaric acid, citric acid, lactic acid or glycollic acid, a mixture of these acids, a mixture of a mineral acid, for example, hydrochloric acid or sulfuric acid, with an organic acid or a mixture of a mineral acid with the salt of an organic acid, is added to the bath in a quantity such that the total quantity of alkali in the bath and on the textile material is neutralized and a pH-value of between about 4 and 7 is reached.
- an organic acid for example, formic acid, acetic acid, tartaric acid, citric acid, lactic acid or glycollic acid, a mixture of these acids, a mixture of a mineral acid, for example, hydrochloric acid or sulfuric acid, with an organic acid or a mixture of a mineral acid with the salt of an organic acid
- the pH-value required for obtaining optimum dyestuff yield depends, above all, on the diazoamino compound of the Formula 1 used.
- the pH-value is at about 5, in the case of compounds in which R is alkoxycarbamylphenyl it is at about 5, in the case of compounds in which R is alkoxysulfamylphenyl at about 4 and in the case of compounds in which R is acylaminophenyl it is at about 6.
- the temperature required for the dyestuff formation is in the range of between about 10 and about 40 C.
- the material is subsequently washed in a neutral or acid bath, if desired or required in the presence of dispersing agents, and the dyeing is further treated in the usual manner. In this manner, dyeings are obtained which exhibit very good fastness to rubbing.
- Piece goods can be dyed in the following manner: the goods are impregnated on a two or multiple roller foulard with a mixture of the coupling component and an excess of diazoamino compound, the goods are wound up and after a period of stay of, for example, half an hour, coupling is effected at temperatures below 40 C. by passing the goods through an organic acid, a mixture of organic acids or a mixture of organic and mineral acids.
- This dyestuff development may be effected by a single passage in a compartment of a roller vat or by several passages in a jigger or winch beck; the addition of mineral salts and dispersing agents during impregnation and development may sometimes have a very advantageous effect.
- the concentration of the coupling component in the initial bath must be lower in comparison to that of the second bath, corresponding to the higher afiinity of the coupling component, whereas the concentration of the diazoamino compound in the initial bath compared to that of the second bath is not to be reduced.
- This method of operation saves energy; intermediate drying of the dyestufi prior to the development of the dyestuff is not required.
- coupling components there may be used in the process of the present invention compounds which are distinguished by a high substantivity towards the textile material used, i.e. coupling components, which at a goods to liquor ratio of 1:20, a dyeing period of 30 minutes, at 30 C., a concentration of 1 g. per liter of water, without addition of salt and with an excess of 4.5 g. of sodium hydroxide per liter of bath, have so high a substantivity that at least 9 g. are absorbed on 1 kg. of cotton.
- coupling components which at a goods to liquor ratio of 1:20, a dyeing period of 30 minutes, at 30 C., a concentration of 1 g. per liter of water, without addition of salt and with an excess of 4.5 g. of sodium hydroxide per liter of bath, have so high a substantivity that at least 9 g. are absorbed on 1 kg. of cotton.
- Suitable compounds are, for example, 2,3-hydroxynaphthoyl-aminobenzenes 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 aryl amides such as 1-(6'-bromo- 2',3 hydroxynaphthoylamino)-2-methoxybenzene, condensation products of 2,3-hydroxynaphthoic acid and oligonuclear isocyclic or heterocyclic amines such as 2- (2,3' hydroxynaphthoylamino)-naphthalene, 2-(2,3'- hydroxynaphthoylamino) carbazole, 2 (2'3-hydroxyn
- wetting or dispersing agents there may be used the compounds conventionally used in ice colour technique, for example, condensation products of higher molecular fatty acids and protein degradation products, condensation products of higher molecular fatty acids and aminoalkysulfonic acids, condensation products of formaldehyde with naphthalene-sulfonic acids, or purified sulfite cellulose waste liquor.
- the process 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 considarably simpler.
- the dyebath is usually drained after the impregnation with the coupling component, the goods are centrifuged, separated with suction or rinsed intermediately and the dyestufr is developed with a diazonium compound in a second bath.
- impregnation and development are carried out 31 one bath and after the period of stay required for fixing the coupling component, coupling is effected without any other intercalated operation, which saves operational time to a considerable degree.
- diazoamino compounds of diazotized aromatic amines and N-(methyl)-aminoacetic acid, iminodiacetic acid, N-methyltaurine or N-alkyl-sulfanilic acids may be used for the production of azo dyestuffs on the fiber, by printing such diazoamino componds in admixture with coupling components on the material and developing the dyestuffs by a treatment with acids.
- This process is at present widely used in industry.
- water-insoluble azo dyestuffs can be produced on vegetable fibers by treating these fibers at long goods to liquor ratios with a bath containing a coupling component and a diazo or tetrazoamino compound without hydrosolubilizing groups and subsequently developing the azo dyestuif by treatment with an acid bath (German Patent 1,057,061).
- the process of the present invention which is carried out with substantive coupling components and diazoamino compounds of the indicated Formula 1 is distinguished by the fact that the development of the dyestuffs can be effected at low temperatures and that it is not necessary to raise the temperature after the addition of acid.
- Another advantage of the process of the present invention is that the diazoamino compound with aliphatic aminocarboxylic acids as stabilizers are present in the bath in the form of dissolved alkali metal salts, which ensures complete penetration of the material to be dyed and thus complete coupling, whereas, if water-insoluble diazoamino compounds are used, these compounds are only deposited on the surface of the material to be dyed which turns out in unsatisfactory dyeings and fastness to rubbing.
- EXAMPLE 1 A cross-wound bobbin of 500 g. of cotton was treated for 30 minutes at 30 C. on a dyeing apparatus in the following bath:
- EXAMPLE 5 g. of sodium chloride and 2.35 g. of the diazoamino Cotton on cross-wound bobbins was treated, at a goods compound of the formula to liquor ratio of 1:10, for half an hour, at 2530 C., in a bath containing, per liter of liquor, 1 g. of the sodi- (IJHS um salt of ethylenendiarninotetracetic acid, 1 g. of a condensation product of oleic acid and methyltaurine, 6.4 O 2 Nab cc. of a sodium hydroxide solution of 38 B., 1.1 g. of A) 2-(2,3'-hydroxynaphthoylamino) naphthalene, 30 g.
- EXAMPLE 10 1TRl 2 Cotton yarn was treated, at a goods to liquor ratio of 5 1:20, for 15 minutes at 30 C., in the following bath: 1 in Which R is a member Selected from the group Consistg. of 2- (2',3'-hydroxynaphthoylamino) -3 -methoxy-dig f p y ehlerophenyl, lower y p y lower phenylene oxide was dissolved in 2 cc. of denatured ethyl alkOXY P 31 (ii-lower y p y lower alkylchloroalcohol, 0.5 cc.
- R is a member Selected from the group Consistg. of 2- (2',3'-hydroxynaphthoylamino) -3 -methoxy-dig f p y ehlerophenyl, lower y p y lower phenylene oxide was dissolved in 2 cc. of denatured
- a 16.4% diazoagent selected from the group consisting of organic acids, amino compound of diazotized l-amino 2 -methy1-5- inorganic acids and mixtures thereof in such an amount chlorobenzene and the sodium salt of N-ethyl-sulfanilic that in the bath and on the textile material a pH value acid, or 4.75 g. of a 16.3% diazoamino compound of dietween about 4 and 7 is achieved.
- sodium phosphate and sodium sulfate is employed.
- a process for producing water-insoluble azo dyestuffs on cellulose and protein textile materials which comprises treating said textile materials at temperatures 1,382,560 10/1932 Glietellburg et between about 10 C. and about 35 C. in an aqueous 3; 3 1 13 0 am ers alkaline bath WhlCh contains (1) a couplln component 2,926,986 3/1960 Petitcolas et a 8 45 which is highly substantive for the textile material employed, said component being selected from the group GEORGE LESMES, Primary Examiner consisting of arylamides of aromatic oitho-hydroxy car- T. J. HERBERT, JR., Assistant Examiner boxylic acids, arylarnides of heterocyclic ortho-hydroxy US. Cl. X.R. carboxylic acids, arylarnides of acyl acetic acids and aryl-
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP1267A DE1267661B (de) | 1964-02-22 | 1964-02-22 | Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial aus Cellulose- oder Eiweissfasern |
| DEP1267A DE1267662B (de) | 1964-02-22 | 1964-03-07 | Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial aus Cellulose- oder Eiweissfasern |
| DE1964F0043370 DE1281393C2 (de) | 1964-02-22 | 1964-07-08 | Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial aus Cellulose- oder Eiweissfasern |
| DEF43563A DE1296124B (de) | 1964-02-22 | 1964-07-25 | Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf Textilmaterial ausCellulose- oder Eiweissfasern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3484181A true US3484181A (en) | 1969-12-16 |
Family
ID=27436916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US433783A Expired - Lifetime US3484181A (en) | 1964-02-22 | 1965-02-18 | Process for the production of water-insoluble azo dyestuffs on textile material of cellulose or protein fibers |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3484181A (uk) |
| JP (1) | JPS4942861B1 (uk) |
| AT (1) | AT266028B (uk) |
| BE (1) | BE660080A (uk) |
| CH (1) | CH461669A (uk) |
| DE (4) | DE1267661B (uk) |
| DK (1) | DK121293B (uk) |
| ES (1) | ES309570A1 (uk) |
| FR (1) | FR1435030A (uk) |
| GB (1) | GB1090795A (uk) |
| NL (1) | NL6502187A (uk) |
| NO (1) | NO119986B (uk) |
| SE (1) | SE220329C1 (uk) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070124872A1 (en) * | 2003-12-19 | 2007-06-07 | Eliu Victor P | Method of coloring with capped diazotized compound and coupling component |
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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1057061B (de) * | 1957-12-21 | 1959-05-14 | Hoechst Ag | Verfahren zur Erzeugung von wasserunloeslichen Azofarbstoffen auf pflanzlichen Fasern |
-
1964
- 1964-02-22 DE DEP1267A patent/DE1267661B/de active Pending
- 1964-03-07 DE DEP1267A patent/DE1267662B/de active Pending
- 1964-07-08 DE DE1964F0043370 patent/DE1281393C2/de not_active Expired
- 1964-07-25 DE DEF43563A patent/DE1296124B/de active Pending
-
1965
- 1965-02-17 NO NO156819A patent/NO119986B/no unknown
- 1965-02-18 US US433783A patent/US3484181A/en not_active Expired - Lifetime
- 1965-02-19 ES ES0309570A patent/ES309570A1/es not_active Expired
- 1965-02-19 AT AT148365A patent/AT266028B/de active
- 1965-02-19 DK DK89265AA patent/DK121293B/da unknown
- 1965-02-19 CH CH229365A patent/CH461669A/de unknown
- 1965-02-22 NL NL6502187A patent/NL6502187A/xx unknown
- 1965-02-22 JP JP40009783A patent/JPS4942861B1/ja active Pending
- 1965-02-22 FR FR6465A patent/FR1435030A/fr not_active Expired
- 1965-02-22 GB GB7627/65A patent/GB1090795A/en not_active Expired
- 1965-02-22 SE SE227665A patent/SE220329C1/sv unknown
- 1965-02-22 BE BE660080D patent/BE660080A/xx unknown
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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070124872A1 (en) * | 2003-12-19 | 2007-06-07 | Eliu Victor P | Method of coloring with capped diazotized compound and coupling component |
Also Published As
| Publication number | Publication date |
|---|---|
| BE660080A (uk) | 1965-08-23 |
| DE1267661B (de) | 1968-05-09 |
| ES309570A1 (es) | 1966-01-16 |
| AT266028B (de) | 1968-11-11 |
| SE220329C1 (uk) | 1968-05-07 |
| GB1090795A (en) | 1967-11-15 |
| JPS4942861B1 (uk) | 1974-11-18 |
| DE1267662B (de) | 1968-05-09 |
| NL6502187A (uk) | 1965-08-23 |
| DE1281393C2 (de) | 1973-05-10 |
| FR1435030A (fr) | 1966-04-15 |
| DE1281393B (de) | 1968-10-24 |
| NO119986B (uk) | 1970-08-10 |
| CH461669A (de) | 1968-05-15 |
| DE1296124B (de) | 1969-05-29 |
| DK121293B (da) | 1971-10-04 |
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