DE1246663C2 - Verfahren zum Faerben und Bedrucken von polymeren Kunststoffen - Google Patents
Verfahren zum Faerben und Bedrucken von polymeren KunststoffenInfo
- Publication number
- DE1246663C2 DE1246663C2 DE1963G0037485 DEG0037485A DE1246663C2 DE 1246663 C2 DE1246663 C2 DE 1246663C2 DE 1963G0037485 DE1963G0037485 DE 1963G0037485 DE G0037485 A DEG0037485 A DE G0037485A DE 1246663 C2 DE1246663 C2 DE 1246663C2
- Authority
- DE
- Germany
- Prior art keywords
- radical
- perimidinyl
- carbon atoms
- further substituted
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 9
- 229920003023 plastic Polymers 0.000 title claims description 6
- 239000004033 plastic Substances 0.000 title claims description 6
- 238000004040 coloring Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 27
- -1 alkyl radical Chemical class 0.000 claims description 25
- 239000000835 fiber Substances 0.000 claims description 20
- 238000004043 dyeing Methods 0.000 claims description 11
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 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
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 229920002239 polyacrylonitrile Polymers 0.000 description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 239000007859 condensation product Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 4
- DIVABHLWSIHINR-UHFFFAOYSA-M [Cl-].C[N+]1=C(N(C2=CC=CC3=CC=CC1=C23)C)C Chemical compound [Cl-].C[N+]1=C(N(C2=CC=CC3=CC=CC1=C23)C)C DIVABHLWSIHINR-UHFFFAOYSA-M 0.000 description 4
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- HJXMORWPPSSVMF-UHFFFAOYSA-N 2-methyl-1h-perimidine Chemical class C1=CC(NC(C)=N2)=C3C2=CC=CC3=C1 HJXMORWPPSSVMF-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- FOAQOAXQMISINY-UHFFFAOYSA-N 4-morpholin-4-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1N1CCOCC1 FOAQOAXQMISINY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- DIRKZTUPMGCEOJ-UHFFFAOYSA-M 1-benzyl-2,3-dimethylperimidin-3-ium bromide Chemical compound [Br-].C[N+]1=C(N(C2=CC=CC3=CC=CC1=C23)CC1=CC=CC=C1)C DIRKZTUPMGCEOJ-UHFFFAOYSA-M 0.000 description 1
- NIBFJPXGNVPNHK-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carbaldehyde Chemical group C1=CC(C=O)=C2OC(F)(F)OC2=C1 NIBFJPXGNVPNHK-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DJNUHUMSXPKISX-UHFFFAOYSA-N 4-(4-ethoxy-n-methylanilino)benzaldehyde Chemical compound C1=CC(OCC)=CC=C1N(C)C1=CC=C(C=O)C=C1 DJNUHUMSXPKISX-UHFFFAOYSA-N 0.000 description 1
- XOAGJNOGCZYHSL-UHFFFAOYSA-N 4-[(4-methoxyphenyl)diazenyl]benzaldehyde Chemical compound C1=CC(OC)=CC=C1N=NC1=CC=C(C=O)C=C1 XOAGJNOGCZYHSL-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JLGANZQJPWLGEI-UHFFFAOYSA-M C1(=CC=C(C=C1)S(=O)(=O)[O-])C.C[N+]1=C(N(C2=CC=CC3=CC=CC1=C23)C)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)[O-])C.C[N+]1=C(N(C2=CC=CC3=CC=CC1=C23)C)C JLGANZQJPWLGEI-UHFFFAOYSA-M 0.000 description 1
- LZBLKGJHQDIVIW-UHFFFAOYSA-M CC(N1CCO)=[N+](C)C2=C3C1=CC=CC3=CC=C2.[Cl-] Chemical compound CC(N1CCO)=[N+](C)C2=C3C1=CC=CC3=CC=C2.[Cl-] LZBLKGJHQDIVIW-UHFFFAOYSA-M 0.000 description 1
- NRKWHIRYOSJEQH-UHFFFAOYSA-M CCN(C(C)=[N+]1CC)C2=CC=CC3=CC=CC1=C23.[Cl-] Chemical compound CCN(C(C)=[N+]1CC)C2=CC=CC3=CC=CC1=C23.[Cl-] NRKWHIRYOSJEQH-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PQYFXOZCVLYEIS-UHFFFAOYSA-M [Cl-].C[N+]1=C(N(C2=CC=CC3=CC=CC1=C23)CC)C Chemical compound [Cl-].C[N+]1=C(N(C2=CC=CC3=CC=CC1=C23)CC)C PQYFXOZCVLYEIS-UHFFFAOYSA-M 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005528 methosulfate group Chemical group 0.000 description 1
- MVCXBMAXWHWFSV-UHFFFAOYSA-N n'-[2-(hexadecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCNCCNCCN MVCXBMAXWHWFSV-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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- WEMXRTXQKRXSIO-UHFFFAOYSA-N propanenitrile Chemical compound [CH2]CC#N WEMXRTXQKRXSIO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- CRUISIDZTHMGJT-UHFFFAOYSA-L zinc;dichloride;hydrochloride Chemical compound Cl.[Cl-].[Cl-].[Zn+2] CRUISIDZTHMGJT-UHFFFAOYSA-L 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
- C09B43/00—Preparation of azo dyes from other azo compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
- C08K5/3465—Six-membered rings condensed with 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
- C09B23/146—(Benzo)thiazolstyrylamino dyes
-
- 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/108—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system characterised by a cyclammonium six-membered specific ring not mentioned hereafter, e.g. pyrimidinium, perimidinium, pyridazonium, oxazinium
-
- 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/16—Methine- or polymethine-azo dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/927—Polyacrylonitrile fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH433662A CH374628A (de) | 1962-04-10 | 1962-04-10 | Verfahren zum Färben und Bedrucken von Textilmaterialien aus Polyacrylnitril |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1246663B DE1246663B (de) | 1967-08-10 |
| DE1246663C2 true DE1246663C2 (de) | 1968-02-22 |
Family
ID=4274187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1963G0037485 Expired DE1246663C2 (de) | 1962-04-10 | 1963-04-09 | Verfahren zum Faerben und Bedrucken von polymeren Kunststoffen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3185538A (en, 2012) |
| BE (1) | BE630788A (en, 2012) |
| CH (1) | CH374628A (en, 2012) |
| DE (1) | DE1246663C2 (en, 2012) |
| FR (1) | FR1353338A (en, 2012) |
| GB (1) | GB984905A (en, 2012) |
| NL (2) | NL291341A (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3765835A (en) * | 1968-04-25 | 1973-10-16 | Du Pont | Anionic dispersion of a salt of a cationic dye and a selected arylsulfonate |
| US3660008A (en) * | 1968-04-25 | 1972-05-02 | Du Pont | Dyeing sulfonated anionic polymeric fibers with an aqueous dispersion of a salt of a cationic dye and an arylsulfonate |
| FR2036234A5 (en, 2012) * | 1969-03-07 | 1970-12-24 | Ugine Kuhlmann | |
| DE2340045B2 (de) * | 1973-08-08 | 1978-02-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zum kontinuierlichen faerben und bedrucken von stueckwaren aus mischungen von synthetischen polyamidfasern mit cellulosefasern mit reaktivfarbstoffen nach der thermofixiermethode |
| NL7410432A (nl) * | 1973-08-08 | 1975-02-11 | Hoechst Ag | Werkwijze voor het continu verven van wol. |
| CH661275A5 (de) * | 1984-08-22 | 1987-07-15 | Ciba Geigy Ag | Methin-azo-verbindungen. |
| US5097029A (en) * | 1989-07-03 | 1992-03-17 | Hercules Incorporated | Process for preparing 2,3-dihydro-1,3-dialkyl-2,3-dialkyl perimidines and N,N-'-dialkyl-1,8-naphthalene diamines |
| US5147568A (en) * | 1991-05-07 | 1992-09-15 | Ciba-Geigy Corporation | Substituted 2,3-dihydroperimidine stabilizers |
| US5360694A (en) * | 1993-10-18 | 1994-11-01 | Minnesota Mining And Manufacturing Company | Thermal dye transfer |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2989361A (en) * | 1961-06-20 | Dyeing process | ||
| US2772943A (en) * | 1956-12-04 | Process of dyeing wool-polyacrylo- | ||
| US2494032A (en) * | 1946-06-03 | 1950-01-10 | Eastman Kodak Co | Styryl dyes |
| US2840443A (en) * | 1954-08-05 | 1958-06-24 | Gen Aniline & Film Corp | Use of methylidyne bis pyrazolones for dyeing |
| BE551825A (en, 2012) * | 1955-10-25 | |||
| DE1049994B (en, 2012) * | 1957-03-28 | |||
| US3119806A (en) * | 1961-08-24 | 1964-01-28 | Geigy Ag J R | Perimidinium azo dyestuffs |
-
0
- NL NL126390D patent/NL126390C/xx active
- NL NL291341D patent/NL291341A/xx unknown
-
1962
- 1962-04-10 CH CH433662A patent/CH374628A/de unknown
-
1963
- 1963-04-01 US US269710A patent/US3185538A/en not_active Expired - Lifetime
- 1963-04-09 DE DE1963G0037485 patent/DE1246663C2/de not_active Expired
- 1963-04-09 FR FR930880A patent/FR1353338A/fr not_active Expired
- 1963-04-09 GB GB14068/63A patent/GB984905A/en not_active Expired
- 1963-04-09 BE BE630788D patent/BE630788A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3185538A (en) | 1965-05-25 |
| FR1353338A (fr) | 1964-02-21 |
| NL291341A (en, 2012) | |
| CH374628A (de) | 1964-03-13 |
| GB984905A (en) | 1965-03-03 |
| DE1246663B (de) | 1967-08-10 |
| BE630788A (en, 2012) | 1963-11-04 |
| NL126390C (en, 2012) | |
| CH433662A4 (en, 2012) | 1963-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1246663C2 (de) | Verfahren zum Faerben und Bedrucken von polymeren Kunststoffen | |
| DE1644328C3 (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| DE1139094B (de) | Verfahren zum Faerben und Bedrucken von Textilmaterial aus Polyacrylnitril, acrylnitrilhaltigen Mischpolymerisaten oder Celluloseacetat | |
| DE2260703A1 (de) | Verfahren zum faerben von textilfasermaterial aus polyacrylnitril | |
| CH433662A (de) | Tragvorrichtung für Deckenverkleidung | |
| DE2006131B2 (de) | Mono- und Disazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung zum Färben und Bedrucken von Acryl-, Nylon- oder Polypropylenfasern, sowie von estergruppenhaltigen Fasern | |
| DE1241014B (de) | Verfahren zur Herstellung von Tetrazapolymethinfarbstoffen | |
| DE2533428A1 (de) | Kationische farbstoffe | |
| DE2013791A1 (en) | Yellow basic hydrazone dyes for polyacry-lonitrile etc | |
| CH559664A5 (en, 2012) | ||
| DE2030028B2 (de) | Basische Oxazinfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1544509C3 (de) | Basische Triazolmonoazofarbstoffe und Verfahren zu deren Herstellung | |
| DE2352858A1 (de) | Wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung | |
| DE1248192B (de) | Verfahren zur Herstellung von Methinfarbstoffen | |
| DE636283C (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE1469789C (de) | Verfahren zum Färben oder Bedrucken von Textilfasern | |
| DE2840825A1 (de) | Farbstoffe fuer den transferdruck | |
| DE1544514C (de) | Verfahren zur Herstellung von bast sehen Azofarbstoffen | |
| DE1258819B (de) | Verfahren zum Faerben und Bedrucken von Textilmaterial aus nickelhaltigem Polypropylen | |
| DE2064735C3 (de) | Basische ^azinfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2002916A1 (de) | Verfahren zum Faerben oder Bedrucken von Textilmaterial aus Polymerisaten oder Mischpolymerisaten des Acrylnitrils | |
| DE4238231A1 (en, 2012) | ||
| DE1242773B (de) | Verfahren zur Herstellung von basischen Azofarbstoffen | |
| DE666478C (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE914246C (de) | Verfahren zur Herstellung ueberfaerbeechter Faerbungen auf Acetyl-cellulose sowie linearen Polyamiden oder Polyurethanen |