DE1619533B2 - Verfahren zum faerben von polyamiden - Google Patents
Verfahren zum faerben von polyamidenInfo
- Publication number
- DE1619533B2 DE1619533B2 DE1967F0052943 DEF0052943A DE1619533B2 DE 1619533 B2 DE1619533 B2 DE 1619533B2 DE 1967F0052943 DE1967F0052943 DE 1967F0052943 DE F0052943 A DEF0052943 A DE F0052943A DE 1619533 B2 DE1619533 B2 DE 1619533B2
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- parts
- acid
- dyeing
- sodium
- 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.)
- Granted
Links
- 239000004952 Polyamide Substances 0.000 title claims description 11
- 229920002647 polyamide Polymers 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 3
- 238000004040 coloring Methods 0.000 title 1
- 238000004043 dyeing Methods 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 10
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 10
- 239000000835 fiber Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 7
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 241000083869 Polyommatus dorylas Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- -1 phthalic acid imide Chemical class 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 description 3
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- FDOQKGWUMUEJLX-UHFFFAOYSA-N 4,5-dichlorophthalic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C=C1C(O)=O FDOQKGWUMUEJLX-UHFFFAOYSA-N 0.000 description 1
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZIALXKMBHWELGF-UHFFFAOYSA-N [Na].[Cu] Chemical compound [Na].[Cu] ZIALXKMBHWELGF-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001117 oleyl 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])/C([H])=C([H])\C([H])([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
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/065—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide having -COOH or -SO3H radicals or derivatives thereof, directly linked to the skeleton
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid 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
- Y10S8/924—Polyamide fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0052943 DE1619533B2 (de) | 1967-07-13 | 1967-07-13 | Verfahren zum faerben von polyamiden |
| CH896568A CH499674A (de) | 1967-07-13 | 1968-06-17 | Verfahren zum Färben von Textilmaterialien aus Polyamid |
| CH896568D CH896568A4 (enExample) | 1967-07-13 | 1968-06-17 | |
| FI681830A FI46085C (fi) | 1967-07-13 | 1968-06-27 | Menetelmä polyamidista valmistettujen tekstiiliaineiden värjäämiseksi. |
| SE08774/68A SE335971B (enExample) | 1967-07-13 | 1968-06-27 | |
| GB32005/68A GB1182740A (en) | 1967-07-13 | 1968-07-04 | The Dyeing of Polyamides |
| AT648568A AT283260B (de) | 1967-07-13 | 1968-07-05 | Verfahren zum Färben von Polyamiden |
| US742487A US3622263A (en) | 1967-07-13 | 1968-07-05 | Process for the dyeing of polyamide textiles with metal phthalocyanine dyestuffs |
| NO2705/68A NO126697B (enExample) | 1967-07-13 | 1968-07-06 | |
| DK333868AA DK134120B (da) | 1967-07-13 | 1968-07-08 | Fremgangsmåde til farvning af fibermaterialer af syntetiske polyamider med sulfonsyregruppeholdige phthalocyaninfarvestoffer. |
| NL6809685A NL6809685A (enExample) | 1967-07-13 | 1968-07-09 | |
| FR1573616D FR1573616A (enExample) | 1967-07-13 | 1968-07-12 | |
| BE718030D BE718030A (enExample) | 1967-07-13 | 1968-07-12 | |
| JP43048838A JPS5136388B1 (enExample) | 1967-07-13 | 1968-07-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0052943 DE1619533B2 (de) | 1967-07-13 | 1967-07-13 | Verfahren zum faerben von polyamiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1619533A1 DE1619533A1 (de) | 1969-10-23 |
| DE1619533B2 true DE1619533B2 (de) | 1976-04-29 |
Family
ID=7105869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967F0052943 Granted DE1619533B2 (de) | 1967-07-13 | 1967-07-13 | Verfahren zum faerben von polyamiden |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3622263A (enExample) |
| JP (1) | JPS5136388B1 (enExample) |
| AT (1) | AT283260B (enExample) |
| BE (1) | BE718030A (enExample) |
| CH (2) | CH499674A (enExample) |
| DE (1) | DE1619533B2 (enExample) |
| DK (1) | DK134120B (enExample) |
| FI (1) | FI46085C (enExample) |
| FR (1) | FR1573616A (enExample) |
| GB (1) | GB1182740A (enExample) |
| NL (1) | NL6809685A (enExample) |
| NO (1) | NO126697B (enExample) |
| SE (1) | SE335971B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2387658A1 (fr) * | 1977-03-25 | 1978-11-17 | Ciba Geigy Ag | Procede pour combattre les microorganismes |
| JPS55119131U (enExample) * | 1979-02-13 | 1980-08-23 | ||
| US7419537B2 (en) * | 2003-03-31 | 2008-09-02 | Nippon Kayaku Kabushiki Kaisha | Phthalocyanine colorant and use thereof for ink-jet printing |
| GB0316856D0 (en) * | 2003-07-18 | 2003-08-20 | Avecia Ltd | Inks and processes |
| WO2005014724A1 (en) * | 2003-07-18 | 2005-02-17 | Avecia Inkjet Limited | Phthalocyanines and their use in ink-jet printers |
| GB2417249B (en) * | 2003-07-18 | 2007-11-21 | Avecia Inkjet Ltd | Phthalocyanines and their use in ink-jet printers |
| GB2418670B (en) * | 2003-07-18 | 2007-06-27 | Avecia Inkjet Ltd | Phthalocyanines and their use in ink-jet printers |
| TWI434893B (zh) * | 2007-12-28 | 2014-04-21 | Nippon Kayaku Kk | 四氮雜卟啉色素及含有該色素之印墨組成物以及噴墨記錄方法 |
| TW201005045A (en) * | 2008-06-30 | 2010-02-01 | Nippon Kayaku Kk | Porphyrazine pigment, ink composition and colored article |
| CA2747687C (en) | 2008-12-25 | 2016-02-09 | Nippon Kayaku Kabushiki Kaisha | Porphyrazine coloring matter, ink composition containing the same and colored product |
| JP5502856B2 (ja) | 2009-04-15 | 2014-05-28 | 日本化薬株式会社 | ポルフィラジン色素、これを含有するインク組成物及び着色体 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2683643A (en) * | 1949-08-25 | 1954-07-13 | Bayer Ag | Process of dyeing and printing and composition therefor |
| CH370858A (de) * | 1958-12-18 | 1963-07-31 | Ciba Geigy | Verfahren zur Herstellung neuer Phthalocyaninfarbstoffe |
| US3051720A (en) * | 1958-12-29 | 1962-08-28 | Du Pont | Production of phthalocyanine pigments |
-
1967
- 1967-07-13 DE DE1967F0052943 patent/DE1619533B2/de active Granted
-
1968
- 1968-06-17 CH CH896568A patent/CH499674A/de not_active IP Right Cessation
- 1968-06-17 CH CH896568D patent/CH896568A4/xx unknown
- 1968-06-27 SE SE08774/68A patent/SE335971B/xx unknown
- 1968-06-27 FI FI681830A patent/FI46085C/fi active
- 1968-07-04 GB GB32005/68A patent/GB1182740A/en not_active Expired
- 1968-07-05 AT AT648568A patent/AT283260B/de not_active IP Right Cessation
- 1968-07-05 US US742487A patent/US3622263A/en not_active Expired - Lifetime
- 1968-07-06 NO NO2705/68A patent/NO126697B/no unknown
- 1968-07-08 DK DK333868AA patent/DK134120B/da unknown
- 1968-07-09 NL NL6809685A patent/NL6809685A/xx unknown
- 1968-07-12 FR FR1573616D patent/FR1573616A/fr not_active Expired
- 1968-07-12 BE BE718030D patent/BE718030A/xx unknown
- 1968-07-13 JP JP43048838A patent/JPS5136388B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1619533A1 (de) | 1969-10-23 |
| AT283260B (de) | 1970-07-27 |
| FI46085B (enExample) | 1972-08-31 |
| GB1182740A (en) | 1970-03-04 |
| NL6809685A (enExample) | 1969-01-15 |
| NO126697B (enExample) | 1973-03-12 |
| DK134120B (da) | 1976-09-13 |
| DK134120C (enExample) | 1977-02-14 |
| US3622263A (en) | 1971-11-23 |
| BE718030A (enExample) | 1968-12-16 |
| CH499674A (de) | 1970-07-15 |
| CH896568A4 (enExample) | 1970-07-15 |
| FI46085C (fi) | 1972-12-11 |
| FR1573616A (enExample) | 1969-07-04 |
| SE335971B (enExample) | 1971-06-21 |
| JPS5136388B1 (enExample) | 1976-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |