EP1409578A1 - Procede de coloration en masse de materiaux synthetiques - Google Patents
Procede de coloration en masse de materiaux synthetiquesInfo
- Publication number
- EP1409578A1 EP1409578A1 EP02767226A EP02767226A EP1409578A1 EP 1409578 A1 EP1409578 A1 EP 1409578A1 EP 02767226 A EP02767226 A EP 02767226A EP 02767226 A EP02767226 A EP 02767226A EP 1409578 A1 EP1409578 A1 EP 1409578A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydrogen
- carboxylic acid
- alkylthio
- arylthio
- alkoxy
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 229920002994 synthetic fiber Polymers 0.000 title claims abstract description 11
- 238000004040 coloring Methods 0.000 title claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 15
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 14
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims abstract description 14
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 14
- 229920001897 terpolymer Polymers 0.000 claims abstract description 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 29
- 239000008187 granular material Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- -1 methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy Chemical group 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- OUKFCUWFFHLVBM-UHFFFAOYSA-N buta-1,3-diene;prop-2-enamide;styrene Chemical compound C=CC=C.NC(=O)C=C.C=CC1=CC=CC=C1 OUKFCUWFFHLVBM-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000549 coloured material Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
-
- 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
Definitions
- R 12 is hydrogen, a carboxylic acid group or a carboxylic acid ester group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
L'invention concerne un procédé de coloration en masse de matériaux synthétiques constitués de terpolymères d'acrylonitrile, de butadiène et de styrène, qui consiste à utiliser au moins un colorant de formule (1) dans laquelle R1 représente un hydrogène, un halogène, un groupe alcoxy, aryloxy, alkylthio ou arylthio, R2 représente un hydrogène, un groupe acide carboxylique ou ester d'acide carboxylique, R3 représente un hydrogène, un halogène, un groupe alcoxy, aryloxy, alkylthio, arylthio, un groupe acide carboxylique ou ester d'acide carboxylique, et W représente un radical de formules (2), (3), (4), (5), (6), dans lesquelles R4, R8 et R11 représentent, d'une manière indépendante les uns des autres, un hydrogène, un groupe alkyle, alcoxy, aryloxy, alkylthio ou arylthio, R5, R7 et R10 représentent, d'une manière indépendante les uns des autres, un hydrogène, un groupe alcoxy, aryloxy, alkylthio, arylthio, un groupe acide carboxylique ou ester d'acide carboxylique, R6 et R9 représentent, d'une manière indépendante l'un de l'autre un groupe cyano, -CONR12R13 ou -SO2R14, dans lesquels R12 et R13 représentent, d'une manière indépendante l'un de l'autre, un hydrogène ou un groupe C1-C4alkyle et R14 représente un groupe C1-C4alkyle, et X représente un groupe -NH-, -0- ou -S-, ou R5 et R5' forment ensemble un groupe phényle ou naphtyle.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02767226A EP1409578A1 (fr) | 2001-07-26 | 2002-07-18 | Procede de coloration en masse de materiaux synthetiques |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01810736 | 2001-07-26 | ||
| EP01810736 | 2001-07-26 | ||
| EP02767226A EP1409578A1 (fr) | 2001-07-26 | 2002-07-18 | Procede de coloration en masse de materiaux synthetiques |
| PCT/EP2002/007987 WO2003010229A1 (fr) | 2001-07-26 | 2002-07-18 | Procede de coloration en masse de materiaux synthetiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1409578A1 true EP1409578A1 (fr) | 2004-04-21 |
Family
ID=8184054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP02767226A Withdrawn EP1409578A1 (fr) | 2001-07-26 | 2002-07-18 | Procede de coloration en masse de materiaux synthetiques |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20040231073A1 (fr) |
| EP (1) | EP1409578A1 (fr) |
| JP (1) | JP2004536200A (fr) |
| WO (1) | WO2003010229A1 (fr) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2415055A1 (de) * | 1974-03-28 | 1975-10-02 | Bayer Ag | Metallkomplexfarbstoffe |
| DE2428198C3 (de) * | 1974-06-11 | 1978-10-19 | Basf Ag, 6700 Ludwigshafen | Naphtholactamfarbstoffe, deren Herstellung und diese Farbstoffe enthaltende Farbstoffzubereitungen |
| CH614229A5 (fr) * | 1975-02-28 | 1979-11-15 | Ciba Geigy Ag | |
| US4180665A (en) * | 1976-06-01 | 1979-12-25 | Ciba-Geigy Aktiengesellschaft | Substituted 3-benz(cd)indol-2-(1H)-ylidene-furo[2,3-b]quinoxalin-2(3H)one dyestuffs |
| CA1085839A (fr) * | 1976-06-01 | 1980-09-16 | Ciba-Geigy Ag | Colorants de naphtolactame |
| US4246410A (en) * | 1976-06-01 | 1981-01-20 | Ciba -Geigy Aktiengesellschaft | Naphtholactam dyestuffs |
| LU75606A1 (fr) * | 1976-08-17 | 1978-04-13 |
-
2002
- 2002-07-18 EP EP02767226A patent/EP1409578A1/fr not_active Withdrawn
- 2002-07-18 JP JP2003515587A patent/JP2004536200A/ja active Pending
- 2002-07-18 WO PCT/EP2002/007987 patent/WO2003010229A1/fr not_active Ceased
- 2002-07-18 US US10/484,355 patent/US20040231073A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| See references of WO03010229A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004536200A (ja) | 2004-12-02 |
| WO2003010229A1 (fr) | 2003-02-06 |
| US20040231073A1 (en) | 2004-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 20031219 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SK TR |
|
| AX | Request for extension of the european patent |
Extension state: AL LT LV MK RO SI |
|
| 17Q | First examination report despatched |
Effective date: 20060818 |
|
| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: CIBA SPECIALTY CHEMICALS HOLDING I |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20061229 |