US20010020313A1 - Process for bulk dyeing of plastics - Google Patents
Process for bulk dyeing of plastics Download PDFInfo
- Publication number
- US20010020313A1 US20010020313A1 US09/789,367 US78936701A US2001020313A1 US 20010020313 A1 US20010020313 A1 US 20010020313A1 US 78936701 A US78936701 A US 78936701A US 2001020313 A1 US2001020313 A1 US 2001020313A1
- Authority
- US
- United States
- Prior art keywords
- substituted
- independently
- another
- unsubstituted
- dye
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 229920003023 plastic Polymers 0.000 title claims abstract description 19
- 239000004033 plastic Substances 0.000 title claims abstract description 19
- 238000004043 dyeing Methods 0.000 title claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 239000000975 dye Substances 0.000 claims description 46
- -1 1,3-phenylene, 1,4-phenylene Chemical group 0.000 claims description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 5
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000001448 anilines Chemical class 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 229910019213 POCl3 Inorganic materials 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 9
- 238000000465 moulding Methods 0.000 description 9
- UPKGPAHZWGYXRK-GVSCDKSHSA-N CC.CC.[C-]#[N+]/C(C)=C/C1=CC=C(N(C)[Y]N(C)C2=CC=C(/C=C(/C)C#N)C(C)=C2)C=C1C Chemical compound CC.CC.[C-]#[N+]/C(C)=C/C1=CC=C(N(C)[Y]N(C)C2=CC=C(/C=C(/C)C#N)C(C)=C2)C=C1C UPKGPAHZWGYXRK-GVSCDKSHSA-N 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000004040 coloring Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 0 *C*.*CN(C)C1=CC=CC(C)=C1.CC.CC.CC.CC.CC.CC.CC1=CC(N(C)CN(C)C2=CC=CC(C)=C2)=CC=C1.CNC1=CC(C)=CC=C1.CNC1=CC(C)=CC=C1.CNC1=CC=CC(C)=C1 Chemical compound *C*.*CN(C)C1=CC=CC(C)=C1.CC.CC.CC.CC.CC.CC.CC1=CC(N(C)CN(C)C2=CC=CC(C)=C2)=CC=C1.CNC1=CC(C)=CC=C1.CNC1=CC(C)=CC=C1.CNC1=CC=CC(C)=C1 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 150000002605 large molecules Chemical class 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- XPJURJQLBIAPSJ-UHFFFAOYSA-N *.[C-]#[N+]C(=CC1=CC=C(N(CC)CCCCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CC)CCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-] Chemical compound *.[C-]#[N+]C(=CC1=CC=C(N(CC)CCCCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CC)CCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-] XPJURJQLBIAPSJ-UHFFFAOYSA-N 0.000 description 1
- RYPLTYRVWRCKEC-UHFFFAOYSA-N *.[C-]#[N+]C(=CC1=CC=C(N(CC)CCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-] Chemical compound *.[C-]#[N+]C(=CC1=CC=C(N(CC)CCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-] RYPLTYRVWRCKEC-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BZHOAXMIZQMPPH-UHFFFAOYSA-N C=C.[C-]#[N+]C(=CC1=CC=C(N(CCCC)CCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1)[N+]#[C-] Chemical compound C=C.[C-]#[N+]C(=CC1=CC=C(N(CCCC)CCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1)[N+]#[C-] BZHOAXMIZQMPPH-UHFFFAOYSA-N 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 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 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- GPDSPRVHKMEMIL-LSJYMSIHSA-N [C-]#[N+]/C(=C\C1=CC=C(N(C)CCN(C)C2=CC=C(/C=C(/C#N)C(=O)OCC)C(C)=C2)C=C1C)COOCC.[C-]#[N+]C(=CC1=CC=C(N(C)CCN(C)C2=CC=C(C=C(C#N)C#N)C=C2)C=C1)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CC)CCN(CC)C2=CC=C(C=C(C#N)C#N)C(OC)=C2)C=C1OC)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CC)CCOCCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CCC#N)CCCCN(CCC#N)C2=CC=C(C=C(C#N)C#N)C=C2)C=C1)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)CC2=CC=CC=C2)C=C1)[N+]#[C-] Chemical compound [C-]#[N+]/C(=C\C1=CC=C(N(C)CCN(C)C2=CC=C(/C=C(/C#N)C(=O)OCC)C(C)=C2)C=C1C)COOCC.[C-]#[N+]C(=CC1=CC=C(N(C)CCN(C)C2=CC=C(C=C(C#N)C#N)C=C2)C=C1)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CC)CCN(CC)C2=CC=C(C=C(C#N)C#N)C(OC)=C2)C=C1OC)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CC)CCOCCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CCC#N)CCCCN(CCC#N)C2=CC=C(C=C(C#N)C#N)C=C2)C=C1)[N+]#[C-].[C-]#[N+]C(=CC1=CC=C(N(CCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)CC2=CC=CC=C2)C=C1)[N+]#[C-] GPDSPRVHKMEMIL-LSJYMSIHSA-N 0.000 description 1
- WACJFHKSEVETTG-UHFFFAOYSA-N [C-]#[N+]C(=CC1=CC=C(N(CC)CCCCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-] Chemical compound [C-]#[N+]C(=CC1=CC=C(N(CC)CCCCN(CC)C2=CC=C(C=C(C#N)C#N)C(C)=C2)C=C1C)[N+]#[C-] WACJFHKSEVETTG-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine 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
- 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
- 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
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
Definitions
- the invention relates to a process for bulk dyeing of plastics with dyes of the formula (I).
- the invention relates to a process for bulk dyeing of plastics comprising the step of adding a dye of the formula (I).
- Y is a bivalent radical selected from the group consisting of substituted and unsubstituted arylenes and alkylenes, and substituted and unsubstituted alkylene radicals interrupted in the main chain by heteroatoms, such as O or S,
- R 1 and R 1 ′ are an electron-withdrawing group, preferably cyano or alkoxycarbonyl, in particular C 1 -C 4 -alkoxycarbonyl,
- R 2 , R 2 ′, R 3 and R 3 independently of one another are hydrogen, alkyl, in particular C 1 -C 4 -alkyl, CF 3 or halogen, preferably F or Cl,
- R 4 and R 4 are unsubstituted or substituted alkyl, preferably C 1 -C 6 -aIkyl, or C 7 -C 12 -aralkyl, preferably benzyl. to plastic.
- Examples of preferred radicals Y include unsubstituted or substituted phenylene, or unsubstituted or substituted C 1 -C 6 -alkylene.
- Examples of more preferred radicals Y include: 1,3-phenylene, 1,4-phenylene or methyl-substituted 1,3- or 1,4-phenylene, —CH 2 —CH 2 —, —CH 2 CH 2 CH 2 —, —(CH 2 ) 4 —, —CH 2 CH(CH 3 )—, —CH 2 CH 2 —O—CH 2 CH 2 — and —CH 2 CH 2 —S—CH 2 CH 2 —.
- radicals Y are alkylene radicals, in particular —CH 2 CH 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, and —CH 2 CH 2 —O—CH 2 CH 2 —.
- R 1 and R 1 ′ examples include: —CN, —CO 2 CH 3 , —CO 2 CH 2 CH 3 , —CO 2 (CH 2 ) 2 CH 3 and —CO 2 (CH 2 ) 3 CH 3 .
- R 2 , R 2 ′, R 3 and R 3 include hydrogen, methyl, ethyl, Cl, F, CF 3 , methoxy and ethoxy.
- R 4 and R 4 ′ examples include CH 3 , ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.
- radicals R 1 ⁇ R 1 , R 2 ⁇ R 2 ′, R 3 ⁇ R 3 and R 4 ⁇ R 4 ′ are equal in formula (I).
- Y is unsubstituted or substituted phenylene, in particular 1,3- or 1,4-phenylene, or unsubstituted or substituted C 2 -C 6 -alkylene, in particular ethylene, propylene or butylene,
- R 1 is CN, CO 2 CH 3 , CO 2 CH 2 CH 3 or CO 2 (CH 2 ) 3 CH 3 ,
- R 2 is hydrogen, CH 3 or CH 2 CH 3 , and
- R 4 is CH 3 , CH 2 CH 3 , n-propyl or n-butyl.
- Bulk dyeing for the purposes of this application, is in particular any process in which the dye of the formula (I) is incorporated into the molten plastic material, including with the aid of an extruder, or in which the dye is added to the starting materials in the preparation of the plastic, e.g., to the monomers, prior to polymerization.
- the approximate processing temperatures for bulk dyeing are from 100 to 380° C.
- Some of the dyes to be used according to the invention are known (e.g., CH-516 628, JP-A 02 292 371), and others may be prepared by analogy with processes known from the literature.
- An example of a preparation is a Vilsmeier formulation followed by condensation with a reactive methylene compound, preferably malononitrile.
- a preferred preparation is the condensation of a substituted aniline with a dihalogenoalkylene (Eq. 1)
- n is from 2 to 6
- X represents halogen, in particular Cl or Br, and the other substituents are as defined above,
- thermoplastics examples include: cellulose esters (such as cellulose nitrate, cellulose acetate, cellulose triacetate, cellulose acetobutyrate and cellulose propionate), cellulose ethers (such as methylcellulose, ethylcellulose and benzylcellulose), linear saturated polyester resins, aniline resins, polycarbonates, polystyrene, polyvinylcarbazole, polyvinyl chloride (in particular unplasticized PVC), polymethacrylates, polyvinylidene chloride, polyacrylonitrile, polyoxymethylenes, linear polyurethanes.
- cellulose esters such as cellulose nitrate, cellulose acetate, cellulose triacetate, cellulose acetobutyrate and cellulose propionate
- cellulose ethers such as methylcellulose, ethylcellulose and benzylcellulose
- linear saturated polyester resins aniline resins
- aniline resins polycarbonates
- polystyrene polyvinylcarbazole
- Examples also include copolymers (such as vinyl chloride-vinyl acetate copolymers), and in particular styrene copolymers (such as styrene-acrylonitrile copolymers (SAN), styrene-butadiene copolymers (SB) and styrene- ⁇ -methylstyrene copolymers (SMS) and acrylonitrile-butadiene-styrene copolymers (ABS).
- SAN styrene-acrylonitrile copolymers
- SB styrene-butadiene copolymers
- SMS styrene- ⁇ -methylstyrene copolymers
- ABS acrylonitrile-butadiene-styrene copolymers
- the high-molecular-weight compounds mentioned may be present individually or in mixtures, as plastic materials or melts, which may be spun to give fibres, if desired.
- the novel process is particularly suitable for bulk dyeing of polystyrene, and in particular for bulk dyeing of poly(meth)acrylates, and preferably polymethyl methacrylate SAN, SMS, ABS, or else polyethylene terephthalate or polybutylene terephthalate.
- the plastic to be dyed is preferably in the form of powders, chips or pellets and is to be mixed intimately with the dye.
- One method of achieving this is by coating the plastic particles with the finely divided, dry, pulverulent dye, or by treating the particles with a solution or dispersion of the dye in an organic solvent and then removing the solvent.
- the process of the invention may also use mixtures of different dyes of the formula (I) and/or mixtures of dyes of the formula (I) with other dyes and/or with inorganic or organic pigments.
- the dyes of the formula (I) are preferably in their solid form, in particular pulverulent or granular, when used according to the invention.
- These solid dye preparations contain at least 95% by weight, preferably at least 98% by weight, in particular more than 99% by weight, of dye of the formula (I) and, if desired, up to 5% by weight of organic binder, in each case based on the dye preparation.
- binders are ethylene oxide-propylene oxide block copolymers, preferably those with a molar mass of from 4000 to 16,000 g/mol.
- the dye preparations are preferably in the form of powders, in particular in the form of dry powders which have been ground and meshed, or else are in the form of pellets, such as those prepared in accordance with EP-A-488 933.
- the ratio of dye to plastic can vary within wide limits, depending on the desired color strength. It is generally advisable to use from 0.005 to 5% by weight, preferably from 0.01 to 2% by weight, of dye, based on the amount of the plastic to be dyed.
- High-quality opaque colorings can be obtained by adding pigments insoluble in the polymers or the polymer/dye mixtures, e.g., titanium dioxide.
- Examples of the amounts of titanium dioxide which can be used are from 0.01 to 10% by weight, preferably from 0.1 to 5% by weight, based on the amount of polymer.
- the treated polymer particles are melted by known processes in an extruder and extruded to give articles such as films or fibres, or cast to give sheets.
- One way of dyeing the plastics with the dyes of the formula (I) is to admix a dye of this type, if desired in the form of a masterbatch, with these substrates using roll mills, mixing equipment or grinding equipment. The dyed material is then brought into its final form by known processes, including calandering, compression molding, extruding, spreading, casting or injection molding.
- plasticizers include esters of phosphoric acid, phthalic acid or sebacic acid.
- the plasticizers may be incorporated prior to or after the incorporation of the dye into the polymers. It is also possible to add any desired amounts of fillers and/or other coloring constituents, such as white pigments, color pigments or black pigments, in order to achieve different shades.
- the resultant greenish-to reddish-yellow colorings have good light resistance and good weathering resistance.
- the dyes of the invention are also very heat-fast within the thermoplastics.
- Example 1 If in Example 1 the dye of the formula (A) was replaced by the dye of the formula
- Example 1 [0060] and the procedure of Example 1 was repeated, yellow-colored moldings with good lightfastness were obtained.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Coloring (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10009580.1 | 2000-02-29 | ||
| DE10009580A DE10009580A1 (de) | 2000-02-29 | 2000-02-29 | Verfahren zum Massefärben von Kunststoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20010020313A1 true US20010020313A1 (en) | 2001-09-13 |
Family
ID=7632861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/789,367 Abandoned US20010020313A1 (en) | 2000-02-29 | 2001-02-20 | Process for bulk dyeing of plastics |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20010020313A1 (de) |
| EP (1) | EP1130052A3 (de) |
| JP (1) | JP2001288274A (de) |
| KR (1) | KR20010085655A (de) |
| CN (1) | CN1311267A (de) |
| CA (1) | CA2338126A1 (de) |
| DE (1) | DE10009580A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030181752A1 (en) * | 2002-01-18 | 2003-09-25 | Josef - Walter Stawitz | Preparation of styryl compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108623825B (zh) * | 2018-05-18 | 2021-07-09 | 海南热带海洋学院 | 海洋污染微塑料染色方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3553245A (en) * | 1964-10-19 | 1971-01-05 | Eastman Kodak Co | Cyanomethylidene aniline compounds |
| CH516628A (de) * | 1967-08-08 | 1971-12-15 | Ciba Geigy Ag | Farbstoffpräparate, welche wasserunlösliche Styrylfarbstoffe enthalten |
| DE2446759C2 (de) * | 1974-10-01 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | Styrylfarbstoffe |
| DE2447229A1 (de) * | 1974-10-03 | 1976-04-15 | Bayer Ag | Styrylfarbstoffe |
| US4331584A (en) * | 1979-06-04 | 1982-05-25 | Sumitomo Chemical Company, Limited | Styryl compounds and coloring synthetic resins therewith |
| JPS6018700B2 (ja) * | 1980-04-28 | 1985-05-11 | 住友化学工業株式会社 | スチリル系化合物、その製法およびそれを用いる高分子有機材料の着色方法 |
| US5218136A (en) * | 1987-12-28 | 1993-06-08 | Sumitomo Chemical Company, Limited | Styryl compounds, process for preparing the same and photoresist compositions comprising the same |
| JPH02292371A (ja) * | 1989-05-02 | 1990-12-03 | Sankyo Kagaku Kk | 感熱転写記録用色素 |
| US5223476A (en) * | 1989-05-02 | 1993-06-29 | Dai Nippon Insatsu Kabushiki Kaisha | Heat transfer sheet |
| US5106942A (en) * | 1990-01-08 | 1992-04-21 | Eastman Kodak Company | Copolymerized methine colorant-polyester color concentrates |
| DE4004614A1 (de) * | 1990-02-15 | 1991-08-22 | Basf Ag | Verfahren zur uebertragung von bichromophoren cyanogruppen enthaltenden methinfarbstoffen |
-
2000
- 2000-02-29 DE DE10009580A patent/DE10009580A1/de not_active Withdrawn
-
2001
- 2001-02-16 EP EP01103520A patent/EP1130052A3/de not_active Withdrawn
- 2001-02-20 US US09/789,367 patent/US20010020313A1/en not_active Abandoned
- 2001-02-23 CA CA002338126A patent/CA2338126A1/en not_active Abandoned
- 2001-02-26 JP JP2001050173A patent/JP2001288274A/ja active Pending
- 2001-02-27 KR KR1020010009925A patent/KR20010085655A/ko not_active Application Discontinuation
- 2001-02-28 CN CN01108951A patent/CN1311267A/zh active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030181752A1 (en) * | 2002-01-18 | 2003-09-25 | Josef - Walter Stawitz | Preparation of styryl compounds |
| US6828455B2 (en) | 2002-01-18 | 2004-12-07 | Bayer Aktiengesellschaft | Preparation of styryl compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1130052A2 (de) | 2001-09-05 |
| CN1311267A (zh) | 2001-09-05 |
| DE10009580A1 (de) | 2001-08-30 |
| JP2001288274A (ja) | 2001-10-16 |
| KR20010085655A (ko) | 2001-09-07 |
| CA2338126A1 (en) | 2001-08-29 |
| EP1130052A3 (de) | 2003-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: BAYER AKTIENGESELLSCHAFT, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:STAWITZ, JOSEF-WALTER;MICHAELIS, STEPHAN;REEL/FRAME:011598/0550;SIGNING DATES FROM 20010111 TO 20010112 |
|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |