CH598337A5 - Yellow to red fibre reactive disperse azo dyes - Google Patents

Yellow to red fibre reactive disperse azo dyes

Info

Publication number: CH598337A5
Authority: CH; Switzerland
Prior art keywords: formula; sep; hydrogen; carrier; ethyl
Prior art date: 1975-06-11

Application number

CH754975A

Other languages

German (de)

English (en)

Inventor

Juergen Dr Markert

Hans Wilhelm Dr Liechti

Raymond Defago

Original Assignee

Ciba Geigy Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-06-11

Filing date

1975-06-11

Publication date

1978-04-28

1975-06-11 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-06-11 Priority to CH754975A priority Critical patent/CH598337A5/de

1976-06-09 Priority to GB2392076A priority patent/GB1525345A/en

1976-06-09 Priority to DE19762625882 priority patent/DE2625882A1/de

1976-06-09 Priority to FR7617378A priority patent/FR2314230A1/fr

1976-06-10 Priority to BE167782A priority patent/BE842784A/fr

1976-06-11 Priority to JP51067851A priority patent/JPS51150528A/ja

1978-04-28 Publication of CH598337A5 publication Critical patent/CH598337A5/de

Links

239000000987 azo dye Substances 0.000 title abstract description 9
239000000835 fiber Substances 0.000 title abstract description 9
238000000034 method Methods 0.000 claims abstract description 23
239000004952 Polyamide Substances 0.000 claims abstract description 9
229920002647 polyamide Polymers 0.000 claims abstract description 9
238000004043 dyeing Methods 0.000 claims abstract description 5
239000000975 dye Substances 0.000 claims description 25
238000007639 printing Methods 0.000 claims description 23
-1 azo compound Chemical class 0.000 claims description 20
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 18
239000011230 binding agent Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 14
239000004744 fabric Substances 0.000 claims description 14
230000008878 coupling Effects 0.000 claims description 13
238000010168 coupling process Methods 0.000 claims description 13
238000005859 coupling reaction Methods 0.000 claims description 13
239000000986 disperse dye Substances 0.000 claims description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 9
150000002431 hydrogen Chemical group 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
238000005917 acylation reaction Methods 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
230000010933 acylation Effects 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
239000011324 bead Substances 0.000 claims description 4
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 4
239000006185 dispersion Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
239000011521 glass Substances 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
239000001856 Ethyl cellulose Substances 0.000 claims description 3
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000002202 Polyethylene glycol Substances 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
239000011248 coating agent Substances 0.000 claims description 3
238000000576 coating method Methods 0.000 claims description 3
239000002270 dispersing agent Substances 0.000 claims description 3
229920001249 ethyl cellulose Polymers 0.000 claims description 3
235000019325 ethyl cellulose Nutrition 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
239000000123 paper Substances 0.000 claims description 3
239000002245 particle Substances 0.000 claims description 3
229920001223 polyethylene glycol Polymers 0.000 claims description 3
238000005507 spraying Methods 0.000 claims description 3
230000008961 swelling Effects 0.000 claims description 3
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 3
210000002268 wool Anatomy 0.000 claims description 3
JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 claims description 2
239000005696 Diammonium phosphate Substances 0.000 claims description 2
239000010425 asbestos Substances 0.000 claims description 2
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 2
229910000388 diammonium phosphate Inorganic materials 0.000 claims description 2
235000019838 diammonium phosphate Nutrition 0.000 claims description 2
235000010292 orthophenyl phenol Nutrition 0.000 claims description 2
238000003825 pressing Methods 0.000 claims description 2
229910052895 riebeckite Inorganic materials 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
125000005179 haloacetyl group Chemical group 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000976 ink Substances 0.000 description 12
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 12
125000001931 aliphatic group Chemical group 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000004753 textile Substances 0.000 description 4
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000002657 fibrous material Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
238000010023 transfer printing Methods 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
239000011888 foil Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
229960004592 isopropanol Drugs 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000005855 radiation Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000985 reactive dye Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KXJGSNRAQWDDJT-UHFFFAOYSA-N 1-acetyl-5-bromo-2h-indol-3-one Chemical compound BrC1=CC=C2N(C(=O)C)CC(=O)C2=C1 KXJGSNRAQWDDJT-UHFFFAOYSA-N 0.000 description 1
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
229920000161 Locust bean gum Polymers 0.000 description 1
229920000715 Mucilage Polymers 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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150000007513 acids Chemical class 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
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229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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239000008112 carboxymethyl-cellulose Substances 0.000 description 1
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238000004040 coloring Methods 0.000 description 1
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239000007859 condensation product Substances 0.000 description 1
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150000004985 diamines Chemical class 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
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238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
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238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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238000007646 gravure printing Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
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RXTNIJMLAQNTEG-UHFFFAOYSA-N hexan-2-yl acetate Chemical compound CCCCC(C)OC(C)=O RXTNIJMLAQNTEG-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000007644 letterpress printing Methods 0.000 description 1
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239000000711 locust bean gum Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
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229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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239000003208 petroleum Substances 0.000 description 1
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239000004033 plastic Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
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229920006306 polyurethane fiber Polymers 0.000 description 1
229920005749 polyurethane resin Polymers 0.000 description 1
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239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000001044 red dye Substances 0.000 description 1
238000007650 screen-printing Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000007966 viscous suspension Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002759 woven fabric Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CH754975A 1975-06-11 1975-06-11 Yellow to red fibre reactive disperse azo dyes CH598337A5 (en)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH754975A CH598337A5 (en)	1975-06-11	1975-06-11	Yellow to red fibre reactive disperse azo dyes
GB2392076A GB1525345A (en)	1975-06-11	1976-06-09	Fibre-reactive disperse dyes their manufacture and use
DE19762625882 DE2625882A1 (de)	1975-06-11	1976-06-09	Faserreaktive dispersionsfarbstoffe, deren herstellung und verwendung
FR7617378A FR2314230A1 (fr)	1975-06-11	1976-06-09	Colorants disperses, reactifs sur fibres, leur procede de preparation et leur utilisation
BE167782A BE842784A (fr)	1975-06-11	1976-06-10	Colorants disperses
JP51067851A JPS51150528A (en)	1975-06-11	1976-06-11	Fiber reactive disperse dyestuffs and process for manufacture and use thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH754975A CH598337A5 (en)	1975-06-11	1975-06-11	Yellow to red fibre reactive disperse azo dyes

Publications (1)

Publication Number	Publication Date
CH598337A5 true CH598337A5 (en)	1978-04-28

Family

ID=4326887

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH754975A CH598337A5 (en)	1975-06-11	1975-06-11	Yellow to red fibre reactive disperse azo dyes

Country Status (2)

Country	Link
BE (1)	BE842784A (fr)
CH (1)	CH598337A5 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4189429A (en) *	1978-05-08	1980-02-19	Minnesota Mining And Manufacturing Company	Hydrolyzable silyl-substituted dyestuffs for transfer printing

1975
- 1975-06-11 CH CH754975A patent/CH598337A5/de not_active IP Right Cessation
1976
- 1976-06-10 BE BE167782A patent/BE842784A/fr unknown

Also Published As

Publication number	Publication date
BE842784A (fr)	1976-12-10

Legal Events

Date	Code	Title	Description
1980-04-15	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH671675A5 (fr)	1989-09-29
DE2521988A1 (de)	1975-12-04	Trockenes thermisches verfahren zum faerben und bedrucken von mit kationischen farbstoffen anfaerbbarem organischem material
DE2530885A1 (de)	1976-01-29	Transferdruckverfahren fuer hydrophiles, synthetisches oder gemische aus hydrophilem und synthetischem fasermaterial
DE2449324A1 (de)	1975-04-24	Transferdruckverfahren zum faerben und bedrucken von mit kationischen farbstoffen anfaerbbarem organischem material
DE2040872B2 (de)	1977-08-18	Hydrazonfarbstoffe
DE2832179A1 (de)	1979-02-01	Transferdruckfarbstoffe
CH179075A (de)	1935-08-31	Kapillaraktives Mittel.
DE1954453A1 (de)	1970-08-27	Farbstoffe,Verfahren zu deren Herstellung und ihre Anwendung
EP0041697B1 (fr)	1984-10-03	Procédé pour la teinture et l'impression de matières fibreuses synthétiques et hydrophobes
CH598337A5 (en)	1978-04-28	Yellow to red fibre reactive disperse azo dyes
DE2525854A1 (de)	1976-01-02	Trockenes thermisches verfahren zum faerben und bedrucken von mit kationischen farbstoffen anfaerbbarem organischem material
DE2625882A1 (de)	1976-12-30	Faserreaktive dispersionsfarbstoffe, deren herstellung und verwendung
DE2157771C3 (de)	1981-01-08	Anthrachinonverbindungen sowie deren Verwendung im Wärmetransferdruck
DE2237289C3 (de)	1975-03-06	Verwendung von 5,8-disubstituierten 1-Nitrobenzoylaminoanthrachinonverbindungen als wasserunlösliche, nicht verküpbare Anthrachinonfarbstoffe zum Färben von Cellulosefasern und Kunstfasern, insbesondere in Wasser quellbaren Cellulosefasern
CH638551A5 (de)	1983-09-30	Monoazofarbstoffe und verfahren zu deren herstellung.
CH598336A5 (en)	1978-04-28	Blue disperse fibre reactive anthraquinone dyes
DE2359515A1 (de)	1974-06-06	Trockenes thermisches verfahren zum faerben und bedrucken von mit kationischen farbstoffen anfaerbbarem organischem material
DE2013791B2 (de)	1977-08-25	Basische farbstoffe, verfahren zu deren herstellung und ihre verwendung zum faerben und bedrucken von textilmaterialien und leder, sowie zur herstellung von druckpasten und schreibfluessigkeiten
DE1964917A1 (de)	1970-07-16	Disazofarbstoffe,Verfahren zu ihrer Herstellung und ihre Verwendung
DE2144907B2 (de)	1979-05-03	Neue wasserunlösliche Mono- und Disazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Pigmente
DE2641186A1 (de)	1977-03-24	Trockenes thermisches verfahren zum faerben und bedrucken von organischen materialien
DE2103612C3 (de)	1980-08-28	Wasserunlösliche Azofarbstoffe
EP1085055B1 (fr)	2004-10-20	Colorant azoique, procédé pour sa préparation et son utilisation pour la teinture ou l'impression de matériaux fibreux
DE2623224A1 (de)	1976-12-16	Faserreaktive dispersionsfarbstoffe, deren herstellung und verwendung
DE2125099B2 (de)	1973-07-26	Marineblaue dispersions-disazofarbstoffe, deren herstellung und verwendung