CH618997A5 - Process for the preparation of naphtholactam dyestuffs - Google Patents

Process for the preparation of naphtholactam dyestuffs Download PDF

Info

Publication number: CH618997A5
Authority: CH; Switzerland
Prior art keywords: blue; naphtholactam; radical; optionally; formula
Prior art date: 1976-06-02

Application number

CH693276A

Other languages

German (de)

English (en)

Inventor

Hansrudolf Dr Schwander

Rudolf Zink

Christian Dr Zickendraht

Stefan Dr Koller

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.)

1976-06-02

Filing date

1976-06-02

Publication date

1980-08-29

1976-06-02 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1976-06-02 Priority to CH693276A priority Critical patent/CH618997A5/de

1977-05-31 Priority to GB2300377A priority patent/GB1583160A/en

1977-06-01 Priority to FR7716779A priority patent/FR2353613A1/fr

1977-06-01 Priority to DE19772724701 priority patent/DE2724701A1/de

1977-06-02 Priority to JP6403777A priority patent/JPS5327627A/ja

1980-08-29 Publication of CH618997A5 publication Critical patent/CH618997A5/de

Links

GPYLCFQEKPUWLD-UHFFFAOYSA-N 1h-benzo[cd]indol-2-one Chemical compound C1=CC(C(=O)N2)=C3C2=CC=CC3=C1 GPYLCFQEKPUWLD-UHFFFAOYSA-N 0.000 title claims description 15
238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 3
-1 cycloalkyl radical Chemical class 0.000 claims description 86
239000000975 dye Substances 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 10
238000004043 dyeing Methods 0.000 claims description 10
150000001450 anions Chemical class 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000000547 substituted alkyl group Chemical group 0.000 claims description 5
150000005840 aryl radicals Chemical group 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
238000009987 spinning Methods 0.000 claims description 4
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
KYPOHTVBFVELTG-UHFFFAOYSA-N but-2-enedinitrile Chemical group N#CC=CC#N KYPOHTVBFVELTG-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
229920000642 polymer Polymers 0.000 claims description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 33
239000000835 fiber Substances 0.000 description 8
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
229920002239 polyacrylonitrile Polymers 0.000 description 4
239000011592 zinc chloride Substances 0.000 description 4
235000005074 zinc chloride Nutrition 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000004442 acylamino group Chemical group 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000005521 carbonamide group Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 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
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000004391 aryl sulfonyl group Chemical group 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
229940077388 benzenesulfonate Drugs 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000010186 staining Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000565 sulfonamide group Chemical group 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
210000002268 wool Anatomy 0.000 description 2
239000011701 zinc Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
IUPJSFOHUQGEDR-UHFFFAOYSA-N 1,3-dioxetanedione Chemical compound O=C1OC(=O)O1 IUPJSFOHUQGEDR-UHFFFAOYSA-N 0.000 description 1
HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 description 1
SFGOPNSWEFTAGK-UHFFFAOYSA-N 2-ethoxy-n,n-dimethylaniline Chemical compound CCOC1=CC=CC=C1N(C)C SFGOPNSWEFTAGK-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
IWYVYUZADLIDEY-UHFFFAOYSA-N 4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1 IWYVYUZADLIDEY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920000742 Cotton 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
KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
102100034523 Histone H4 Human genes 0.000 description 1
101001067880 Homo sapiens Histone H4 Proteins 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
YVBSECQAHGIWNF-UHFFFAOYSA-N N-methyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2N(C)CCCC2=C1 YVBSECQAHGIWNF-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940050390 benzoate Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 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
229910052793 cadmium Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000010000 carbonizing Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
229940089960 chloroacetate Drugs 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical group ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
CFZXDJWFRVEWSR-BUHFOSPRSA-N indigo carmine (acid form) Chemical compound N/1C2=CC=C(S(O)(=O)=O)C=C2C(=O)C\1=C1/NC2=CC=C(S(=O)(=O)O)C=C2C1=O CFZXDJWFRVEWSR-BUHFOSPRSA-N 0.000 description 1
239000000976 ink Substances 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
XLEMRIJDZGESRG-UHFFFAOYSA-N n,n-diethylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(CC)CC)=CC=CC2=C1 XLEMRIJDZGESRG-UHFFFAOYSA-N 0.000 description 1
AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
150000003015 phosphoric acid halides Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920006149 polyester-amide block copolymer Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920006306 polyurethane fiber Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000013535 sea water Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/06—Naphtholactam dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)

CH693276A 1976-06-02 1976-06-02 Process for the preparation of naphtholactam dyestuffs CH618997A5 (en)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CH693276A CH618997A5 (en)	1976-06-02	1976-06-02	Process for the preparation of naphtholactam dyestuffs
GB2300377A GB1583160A (en)	1976-06-02	1977-05-31	Cationic naphtholactam dyes and the production and use thereof
FR7716779A FR2353613A1 (fr)	1976-06-02	1977-06-01	Colorants naphtolactame cationiques, leur procede de preparation et leur application
DE19772724701 DE2724701A1 (de)	1976-06-02	1977-06-01	Neue kationische naphtholactam-farbstoffe, deren herstellung und verwendung
JP6403777A JPS5327627A (en)	1976-06-02	1977-06-02	New cationic naphtholactam dyestuffs* process for manufacture thereof and use thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH693276A CH618997A5 (en)	1976-06-02	1976-06-02	Process for the preparation of naphtholactam dyestuffs

Publications (1)

Publication Number	Publication Date
CH618997A5 true CH618997A5 (en)	1980-08-29

Family

ID=4317305

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH693276A CH618997A5 (en)	1976-06-02	1976-06-02	Process for the preparation of naphtholactam dyestuffs

Country Status (5)

Country	Link
JP (1)	JPS5327627A (2)
CH (1)	CH618997A5 (2)
DE (1)	DE2724701A1 (2)
FR (1)	FR2353613A1 (2)
GB (1)	GB1583160A (2)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4332937A (en) *	1979-04-04	1982-06-01	Ciba-Geigy Corporation	Naphtholactam compounds
JP4150488B2 (ja) *	2000-04-07	2008-09-17	花王株式会社	染毛剤組成物

1976
- 1976-06-02 CH CH693276A patent/CH618997A5/de not_active IP Right Cessation
1977
- 1977-05-31 GB GB2300377A patent/GB1583160A/en not_active Expired
- 1977-06-01 DE DE19772724701 patent/DE2724701A1/de not_active Withdrawn
- 1977-06-01 FR FR7716779A patent/FR2353613A1/fr active Granted
- 1977-06-02 JP JP6403777A patent/JPS5327627A/ja active Pending

Also Published As

Publication number	Publication date
FR2353613A1 (fr)	1977-12-30
JPS5327627A (en)	1978-03-15
FR2353613B1 (2)	1980-01-04
DE2724701A1 (de)	1977-12-15
GB1583160A (en)	1981-01-21

Legal Events

Date	Code	Title	Description
1982-02-26	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2340569A1 (de)	1975-02-27	Azofarbstoffe
DE1769423A1 (de)	1971-09-16	Neue Disazoverbindungen,Verfahren zu deren Herstellung und Anwendung
DE2040872C3 (de)	1978-04-20	Hydrazonfarbstoffe
EP0055224A2 (de)	1982-06-30	Verfahren zum Spinnfärben von Polymeren oder Mischpolymeren des Acrylnitrils
DE2945028A1 (de)	1981-05-21	Quartaere und basische azamethinverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel
DE2209838A1 (de)	1972-09-14	Azofarbstoffe
DE2926183A1 (de)	1980-01-03	Kationische farbstoffe
DE1919511C3 (de)	1975-09-18	Basische Oxazinfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
CH618997A5 (en)	1980-08-29	Process for the preparation of naphtholactam dyestuffs
DE2012050B2 (de)	1979-06-28	Hydroxypyridongruppen enthaltende Methin- und Polymethinfarbstoffe und ihre Herstellung
DE2600036A1 (de)	1976-07-15	Organische verbindungen
DE2022624A1 (de)	1971-04-29	Basischer Disazofarbstoff und Verfahren zur Herstellung desselben
DE1544458A1 (de)	1969-07-31	Verfahren zur Herstellung basischer Farbstoffe
EP0017621A1 (de)	1980-10-15	Naphtholactamverbindungen, Verfahren zu deren Herstellung sowie ihre Verwendung als Farbstoffe
DE2013791A1 (en)	1971-10-14	Yellow basic hydrazone dyes for polyacry-lonitrile etc
DE1619418A1 (de)	1969-10-23	Verwendung von Azofarbstoffen zum Faerben von Faeden und Fasern aus hydrophoben Polymeren
DE2744655A1 (de)	1978-04-13	Kationische azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung
DE2341289A1 (de)	1975-03-06	Basische farbstoffe, verfahren zu ihrer herstellung und ihre verwendung
DE1927416A1 (de)	1970-12-10	Basische Azofarbstoffe und Verfahren zu ihrer Herstellung
DE2525113A1 (de)	1976-01-02	Basische farbstoffe, deren herstellung und verwendung
DE2222042A1 (de)	1973-11-22	Basische azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung
DE2360986A1 (de)	1975-07-24	Polycyclische farbstoffe, verfahren zu ihrer herstellung und ihre verwendung
DE2357442C3 (de)	1981-01-22	Naphtholactamfarbstoffe und deren Verwendung
EP0434609A1 (de)	1991-06-26	Verfahren zum Färben von Polyacrylnitrilmaterialien
DE1469688A1 (de)	1968-12-19	Verwendung von Azofarbstoffen zum Faerben von Faeden und Fasern aus hydrophoben Polymeren