DE2404977A1 - Verfahren zum faerben von fasermaterialien - Google Patents

Verfahren zum faerben von fasermaterialien

Info

Publication number: DE2404977A1
Authority: DE; Germany
Prior art keywords: dyes; formula; alkyl; meaning given; parts
Prior art date: 1974-02-01
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.): Pending

Application number

DE19742404977

Other languages

German (de)

English (en)

Inventor

Herbert Dr Hugl

Gerhard Dr Wolfrum

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer 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.)

1974-02-01

Filing date

1974-02-01

Publication date

1975-08-21

1974-02-01 Application filed by Bayer AG filed Critical Bayer AG

1974-02-01 Priority to DE19742404977 priority Critical patent/DE2404977A1/de

1975-01-29 Priority to BE152818A priority patent/BE824912A/xx

1975-01-30 Priority to JP50011990A priority patent/JPS50107281A/ja

1975-01-31 Priority to GB429775A priority patent/GB1445957A/en

1975-01-31 Priority to NL7501186A priority patent/NL7501186A/xx

1975-01-31 Priority to FR7503059A priority patent/FR2273115B1/fr

1975-01-31 Priority to CH115075A priority patent/CH589745B5/xx

1975-01-31 Priority to CH115075D priority patent/CH115075A4/xx

1975-08-21 Publication of DE2404977A1 publication Critical patent/DE2404977A1/de

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 45
238000004040 coloring Methods 0.000 title description 5
239000002657 fibrous material Substances 0.000 title description 4
239000000975 dye Substances 0.000 claims description 179
229910052739 hydrogen Inorganic materials 0.000 claims description 38
-1 hydroxy, amino Chemical group 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical class 0.000 claims description 32
150000003254 radicals Chemical class 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 26
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 20
229950011008 tetrachloroethylene Drugs 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
238000004043 dyeing Methods 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
230000008878 coupling Effects 0.000 claims description 18
238000010168 coupling process Methods 0.000 claims description 18
238000005859 coupling reaction Methods 0.000 claims description 18
229910004013 NO 2 Inorganic materials 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
125000002947 alkylene group Chemical group 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
239000000463 material Substances 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 5
239000000987 azo dye Substances 0.000 claims description 4
239000001005 nitro dye Substances 0.000 claims description 4
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
239000003086 colorant Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
150000004696 coordination complex Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000000542 sulfonic acid group Chemical group 0.000 claims description 2
229920002994 synthetic fiber Polymers 0.000 claims description 2
239000012209 synthetic fiber Substances 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
235000010893 Bischofia javanica Nutrition 0.000 claims 1
240000005220 Bischofia javanica Species 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
239000000460 chlorine Substances 0.000 description 40
229920000728 polyester Polymers 0.000 description 38
239000000243 solution Substances 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000001632 sodium acetate Substances 0.000 description 14
235000017281 sodium acetate Nutrition 0.000 description 14
239000000835 fiber Substances 0.000 description 13
125000001309 chloro group Chemical group Cl* 0.000 description 11
238000001816 cooling Methods 0.000 description 10
150000002431 hydrogen Chemical class 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
239000005020 polyethylene terephthalate Substances 0.000 description 9
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
239000004744 fabric Substances 0.000 description 8
229920000139 polyethylene terephthalate Polymers 0.000 description 8
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 7
JIHOVGXINXMLLR-UHFFFAOYSA-N 2-n-phenyl-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2C=CC=CC=2)=N1 JIHOVGXINXMLLR-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 5
FVFVNNKYKYZTJU-UHFFFAOYSA-N 6-chloro-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(Cl)=N1 FVFVNNKYKYZTJU-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 5
238000001035 drying Methods 0.000 description 5
BOWVQLFMWHZBEF-KTKRTIGZSA-N oleoyl ethanolamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCO BOWVQLFMWHZBEF-KTKRTIGZSA-N 0.000 description 5
229940055577 oleyl alcohol Drugs 0.000 description 5
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 5
238000000859 sublimation Methods 0.000 description 5
230000008022 sublimation Effects 0.000 description 5
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
229920002284 Cellulose triacetate Polymers 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
229920002678 cellulose Polymers 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000012954 diazonium Substances 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
ZHMUMDLGQBRJIW-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO ZHMUMDLGQBRJIW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000006193 diazotization reaction Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229920002239 polyacrylonitrile Polymers 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
206010039587 Scarlet Fever Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
ZRSKSQHEOZFGLJ-UHFFFAOYSA-N ammonium adipate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCC([O-])=O ZRSKSQHEOZFGLJ-UHFFFAOYSA-N 0.000 description 2
150000004056 anthraquinones Chemical class 0.000 description 2
QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical group C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
GTRGJJDVSJFNTE-UHFFFAOYSA-N chembl2009633 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 GTRGJJDVSJFNTE-UHFFFAOYSA-N 0.000 description 2
150000008422 chlorobenzenes Chemical class 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical class [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
238000009987 spinning Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 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
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
GKXWTRSVUPXQMM-UHFFFAOYSA-N 1,1,1,2,2-pentachloro-3,3,3-trifluoropropane Chemical compound FC(F)(F)C(Cl)(Cl)C(Cl)(Cl)Cl GKXWTRSVUPXQMM-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
KJDRSWPQXHESDQ-UHFFFAOYSA-N 1,4-dichlorobutane Chemical compound ClCCCCCl KJDRSWPQXHESDQ-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 description 1
BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 1
VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
RGHPCLZJAFCTIK-UHFFFAOYSA-N 2-methylpyrrolidine Chemical compound CC1CCCN1 RGHPCLZJAFCTIK-UHFFFAOYSA-N 0.000 description 1
LCAAMWNMHMBXIC-UHFFFAOYSA-N 3,4-dichloropyrrolidine Chemical compound ClC1CNCC1Cl LCAAMWNMHMBXIC-UHFFFAOYSA-N 0.000 description 1
GSCPDZHWVNUUFI-UHFFFAOYSA-N 3-aminobenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1 GSCPDZHWVNUUFI-UHFFFAOYSA-N 0.000 description 1
JPVKCHIPRSQDKL-UHFFFAOYSA-N 3-aminobenzenesulfonamide Chemical compound NC1=CC=CC(S(N)(=O)=O)=C1 JPVKCHIPRSQDKL-UHFFFAOYSA-N 0.000 description 1
DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-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
SIMYCJOGGRXQIY-UHFFFAOYSA-N 3-chloropyrrolidine Chemical compound ClC1CCNC1 SIMYCJOGGRXQIY-UHFFFAOYSA-N 0.000 description 1
KYINPWAJIVTFBW-UHFFFAOYSA-N 3-methylpyrrolidine Chemical compound CC1CCNC1 KYINPWAJIVTFBW-UHFFFAOYSA-N 0.000 description 1
KFSNHOUZAIGMAF-UHFFFAOYSA-N 3-n,3-n-diethylbenzene-1,3-diamine Chemical compound CCN(CC)C1=CC=CC(N)=C1 KFSNHOUZAIGMAF-UHFFFAOYSA-N 0.000 description 1
OYAHSBDYBOBAAQ-UHFFFAOYSA-N 3-phenyl-1,2,4-thiadiazol-5-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=N1 OYAHSBDYBOBAAQ-UHFFFAOYSA-N 0.000 description 1
GBPBXBUHZSOKTH-UHFFFAOYSA-N 4-chloropiperidine Chemical compound ClC1CCNCC1 GBPBXBUHZSOKTH-UHFFFAOYSA-N 0.000 description 1
KWHPWBXOLZTZMJ-UHFFFAOYSA-N 4-ethylpiperidine Chemical compound CCC1CCNCC1 KWHPWBXOLZTZMJ-UHFFFAOYSA-N 0.000 description 1
ZEYSHALLPAKUHG-UHFFFAOYSA-N 4-methoxypiperidine Chemical compound COC1CCNCC1 ZEYSHALLPAKUHG-UHFFFAOYSA-N 0.000 description 1
UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
VOQQGERWJRIHIK-UHFFFAOYSA-N 5-methyl-2-phenyl-4h-pyrazol-3-imine Chemical compound N=C1CC(C)=NN1C1=CC=CC=C1 VOQQGERWJRIHIK-UHFFFAOYSA-N 0.000 description 1
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920004934 Dacron® Polymers 0.000 description 1
VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000001321 HNCO Methods 0.000 description 1
OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
NULAJYZBOLVQPQ-UHFFFAOYSA-N N-(1-naphthyl)ethylenediamine Chemical compound C1=CC=C2C(NCCN)=CC=CC2=C1 NULAJYZBOLVQPQ-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
229920002302 Nylon 6,6 Polymers 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
ZMJPCIAEJKVKMQ-UHFFFAOYSA-M [4-[[4-[benzyl(methyl)amino]phenyl]-[4-(dimethylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)CC=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 ZMJPCIAEJKVKMQ-UHFFFAOYSA-M 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
239000001000 anthraquinone dye Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000005129 aryl carbonyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000007974 melamines Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
125000004971 nitroalkyl group Chemical group 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012487 rinsing solution Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910000679 solder Inorganic materials 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/46—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
- 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
- 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- 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
- D06P1/90—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 dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/908—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 dyes dissolved in organic solvents or aqueous emulsions thereof using specified dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Coloring (AREA)

DE19742404977 1974-02-01 1974-02-01 Verfahren zum faerben von fasermaterialien Pending DE2404977A1 (de)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
DE19742404977 DE2404977A1 (de)	1974-02-01	1974-02-01	Verfahren zum faerben von fasermaterialien
BE152818A BE824912A (fr)	1974-02-01	1975-01-29	Colorants insolubles dans les solvants organiques, et procede pour teindre des matieres fibreuses
JP50011990A JPS50107281A (xx)	1974-02-01	1975-01-30
GB429775A GB1445957A (en)	1974-02-01	1975-01-31	Process for dyeing fibre materials
NL7501186A NL7501186A (nl)	1974-02-01	1975-01-31	Werkwijze voor het verven van vezelmaterialen.
FR7503059A FR2273115B1 (xx)	1974-02-01	1975-01-31
CH115075A CH589745B5 (xx)	1974-02-01	1975-01-31
CH115075D CH115075A4 (xx)	1974-02-01	1975-01-31

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742404977 DE2404977A1 (de)	1974-02-01	1974-02-01	Verfahren zum faerben von fasermaterialien

Publications (1)

Publication Number	Publication Date
DE2404977A1 true DE2404977A1 (de)	1975-08-21

Family

ID=5906406

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19742404977 Pending DE2404977A1 (de)	1974-02-01	1974-02-01	Verfahren zum faerben von fasermaterialien

Country Status (7)

Country	Link
JP (1)	JPS50107281A (xx)
BE (1)	BE824912A (xx)
CH (2)	CH589745B5 (xx)
DE (1)	DE2404977A1 (xx)
FR (1)	FR2273115B1 (xx)
GB (1)	GB1445957A (xx)
NL (1)	NL7501186A (xx)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59145250A (ja) *	1983-02-04	1984-08-20	Mitsubishi Chem Ind Ltd	アントラキノン化合物及びアントラキノン染料
GB0520833D0 (en) *	2005-10-13	2005-11-23	Avecia Inkjet Ltd	Compound, composition and use
CN104497625B (zh) *	2014-11-19	2017-01-11	浙江科永化工有限公司	一种黄色活性染料化合物、其制备方法及用途
CN112646388A (zh) *	2020-12-24	2021-04-13	杭州吉华江东化工有限公司	一种吡唑单偶氮染料及其制备方法
CN113279271A (zh) *	2021-05-27	2021-08-20	福州华冠针纺织品有限公司	一种酸性染色配方、酸性染色方法及其染色得到的纺织品

1974
- 1974-02-01 DE DE19742404977 patent/DE2404977A1/de active Pending
1975
- 1975-01-29 BE BE152818A patent/BE824912A/xx unknown
- 1975-01-30 JP JP50011990A patent/JPS50107281A/ja active Pending
- 1975-01-31 FR FR7503059A patent/FR2273115B1/fr not_active Expired
- 1975-01-31 CH CH115075A patent/CH589745B5/xx not_active IP Right Cessation
- 1975-01-31 GB GB429775A patent/GB1445957A/en not_active Expired
- 1975-01-31 CH CH115075D patent/CH115075A4/xx unknown
- 1975-01-31 NL NL7501186A patent/NL7501186A/xx unknown

Also Published As

Publication number	Publication date
FR2273115B1 (xx)	1978-10-06
CH115075A4 (xx)	1976-11-15
JPS50107281A (xx)	1975-08-23
NL7501186A (nl)	1975-08-05
FR2273115A1 (xx)	1975-12-26
GB1445957A (en)	1976-08-11
CH589745B5 (xx)	1977-07-15
BE824912A (fr)	1975-07-29

Publication	Publication Date	Title
CH638237A5 (de)	1983-09-15	Farbstoffe der cumarinreihe und deren herstellung.
DE1644328C3 (de)	1974-03-14	Verfahren zur Herstellung von Monoazofarbstoffen
DE2062717B2 (de)	1974-06-27	Azofarbstoffe aus 2,6-Diamino pyridin-derivaten, Verfahren zu deren Herstellung und Verwendung
DE2404977A1 (de)	1975-08-21	Verfahren zum faerben von fasermaterialien
DE1795175C3 (de)	1975-09-18	Wasserlösliche Disazofarbstoffe und ihre Verwendung
DE1954453A1 (de)	1970-08-27	Farbstoffe,Verfahren zu deren Herstellung und ihre Anwendung
DE2134896A1 (de)	1973-02-01	Verfahren zur herstellung von cyangruppenhaltigen azofarbstoffen
DE2531445A1 (de)	1976-02-05	Wasserloesliche azofarbstoffe
DE1544450C3 (de)	1974-06-20	Verfahren zur Herstellung wasserunlöslicher Monoazofarbstoffe
DE1644373A1 (de)	1970-09-03	Monoazofarbstoffe,ihre Herstellung und Verwendung
DE2001821A1 (de)	1971-07-22	Wasserunloesliche Monoazofarbstoffe
DE3016301A1 (de)	1981-10-29	Wasserunloesliche azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung
DE2033253A1 (de)	1971-01-14	Farbstoffe. Verfahren zu deren Herstellung und ihre Anwendung
CH638551A5 (de)	1983-09-30	Monoazofarbstoffe und verfahren zu deren herstellung.
DE2103361C3 (de)	1978-07-13	In Wasser schwer lösliche Monoazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Dispersionsfarbstoffe
DE1923592A1 (de)	1970-10-15	Monoazofarbstoffe
DE2222042A1 (de)	1973-11-22	Basische azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung
CH521430A (de)	1972-04-15	Farbstoffpräparate, welche faserreaktive Farbstoffe enthalten
US3491081A (en)	1970-01-20	Insoluble mono- and disazo dyestuffs containing a 1,3 - benzoxazolin - 2 - one group
DE1544600C (de)	1973-06-14	Monoazofarbstoffe sowie Ver fahren zu ihrer Herstellung und Verwendung
DE1955957C (de)	1972-01-27	Verfahren zur Herstellung von in Was ser schwerlöslichen Azofarbstoffen
DE2101558B2 (de)	1979-07-26	Azofarbstoffe mit heterocyclischen Resten, Verfahren zu ihrer Herstellung und deren Verwendung zum Färben von synthetischen Polyestern
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Legal Events

Date	Code	Title	Description
1979-01-11	OHN	Withdrawal