CA2438672C - Method for in-mold coating a polyolefin article - Google Patents
Method for in-mold coating a polyolefin article Download PDFInfo
- Publication number
- CA2438672C CA2438672C CA2438672A CA2438672A CA2438672C CA 2438672 C CA2438672 C CA 2438672C CA 2438672 A CA2438672 A CA 2438672A CA 2438672 A CA2438672 A CA 2438672A CA 2438672 C CA2438672 C CA 2438672C
- Authority
- CA
- Canada
- Prior art keywords
- coating composition
- work piece
- mold
- process according
- weight
- 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 - Lifetime
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- 238000000576 coating method Methods 0.000 title claims abstract description 108
- 238000000034 method Methods 0.000 title claims abstract description 81
- 239000011248 coating agent Substances 0.000 title claims abstract description 76
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 60
- 239000008199 coating composition Substances 0.000 claims abstract description 82
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 46
- 238000002844 melting Methods 0.000 claims abstract description 5
- 230000008018 melting Effects 0.000 claims abstract description 5
- -1 epoxy-amines Polymers 0.000 claims description 59
- 229920000728 polyester Polymers 0.000 claims description 40
- 150000003254 radicals Chemical class 0.000 claims description 37
- 239000003999 initiator Substances 0.000 claims description 35
- 239000000758 substrate Substances 0.000 claims description 32
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 28
- 125000001931 aliphatic group Chemical group 0.000 claims description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 239000004743 Polypropylene Substances 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 17
- 239000000543 intermediate Substances 0.000 claims description 17
- 229920001155 polypropylene Polymers 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 12
- 150000002978 peroxides Chemical class 0.000 claims description 12
- 229920005862 polyol Polymers 0.000 claims description 12
- 229920000058 polyacrylate Polymers 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- 229920003232 aliphatic polyester Polymers 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 claims description 8
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 8
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical group CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 6
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical group C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 5
- 239000003822 epoxy resin Substances 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- UTHDGOQKIWLLCO-UHFFFAOYSA-N 1-hydroxyhexyl prop-2-enoate Chemical compound CCCCCC(O)OC(=O)C=C UTHDGOQKIWLLCO-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000012462 polypropylene substrate Substances 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 claims description 2
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 claims description 2
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 claims description 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 claims description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920006397 acrylic thermoplastic Polymers 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 2
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 claims description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 2
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 claims 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 claims 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 claims 1
- JYSUEYYBKTVYJR-UHFFFAOYSA-N 3,4-dimethyldioxolane-3,5-diol Chemical compound CC1C(O)OOC1(C)O JYSUEYYBKTVYJR-UHFFFAOYSA-N 0.000 claims 1
- 229910000423 chromium oxide Inorganic materials 0.000 claims 1
- KHAHEULMLHIKKX-UHFFFAOYSA-N dibutyl benzene-1,2-dicarboxylate;dodecanoyl dodecaneperoxoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC.CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC KHAHEULMLHIKKX-UHFFFAOYSA-N 0.000 claims 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims 1
- 229960001826 dimethylphthalate Drugs 0.000 claims 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 claims 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims 1
- 239000004416 thermosoftening plastic Substances 0.000 abstract description 41
- 229920001169 thermoplastic Polymers 0.000 abstract description 37
- 238000000465 moulding Methods 0.000 abstract description 17
- 239000000463 material Substances 0.000 abstract description 14
- 239000012815 thermoplastic material Substances 0.000 abstract description 6
- 239000003973 paint Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 238000001746 injection moulding Methods 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000005530 etching Methods 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 239000003677 Sheet moulding compound Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 239000002987 primer (paints) Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- 229920002397 thermoplastic olefin Polymers 0.000 description 4
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 238000010422 painting Methods 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 2
- CWPKTBMRVATCBL-UHFFFAOYSA-N 3-[1-[1-[(2-methylphenyl)methyl]piperidin-4-yl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound CC1=CC=CC=C1CN1CCC(N2CCC(CC2)N2C(NC3=CC=CC=C32)=O)CC1 CWPKTBMRVATCBL-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 239000004412 Bulk moulding compound Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- B29C37/00—Component parts, details, accessories or auxiliary operations, not covered by group B29C33/00 or B29C35/00
- B29C37/0025—Applying surface layers, e.g. coatings, decorative layers, printed layers, to articles during shaping, e.g. in-mould printing
- B29C37/0028—In-mould coating, e.g. by introducing the coating material into the mould after forming the article
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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- B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
- B29C67/24—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00 characterised by the choice of material
- B29C67/246—Moulding high reactive monomers or prepolymers, e.g. by reaction injection moulding [RIM], liquid injection moulding [LIM]
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- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2023/00—Use of polyalkenes or derivatives thereof as moulding material
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2023/00—Use of polyalkenes or derivatives thereof as moulding material
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- Y10T428/00—Stock material or miscellaneous articles
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- 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
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- Y10T428/31587—Hydrocarbon polymer [polyethylene, polybutadiene, etc.]
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- 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
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- Y10T428/31855—Of addition polymer from unsaturated monomers
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- 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
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- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31913—Monoolefin polymer
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- 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
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- Y10T428/31924—Including polyene monomers
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31928—Ester, halide or nitrile of addition polymer
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Injection Moulding Of Plastics Or The Like (AREA)
- Moulds For Moulding Plastics Or The Like (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/614,953 | 2000-07-12 | ||
| US09/614,953 US6617033B1 (en) | 2000-07-12 | 2000-07-12 | Method for in-mold coating a polyolefin article |
| PCT/US2001/020251 WO2002004187A2 (en) | 2000-07-12 | 2001-06-26 | Method for in-mold coating a polyolefin article |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2438672A1 CA2438672A1 (en) | 2003-07-13 |
| CA2438672C true CA2438672C (en) | 2010-07-27 |
Family
ID=24463397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2438672A Expired - Lifetime CA2438672C (en) | 2000-07-12 | 2001-06-26 | Method for in-mold coating a polyolefin article |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6617033B1 (enExample) |
| EP (1) | EP1299218B1 (enExample) |
| JP (1) | JP4729141B2 (enExample) |
| KR (1) | KR20040002837A (enExample) |
| AT (1) | ATE362831T1 (enExample) |
| CA (1) | CA2438672C (enExample) |
| DE (1) | DE60128568T2 (enExample) |
| MX (1) | MXPA03000375A (enExample) |
| WO (1) | WO2002004187A2 (enExample) |
Families Citing this family (34)
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| US7045213B2 (en) | 2001-10-22 | 2006-05-16 | Omnova Solutions Inc. | In-mold coating injection inlet flow control |
| US6887550B2 (en) | 2001-10-22 | 2005-05-03 | Omnova Solutions Inc. | Removable defined flange for in-mold coating containment |
| US6676877B2 (en) | 2002-04-03 | 2004-01-13 | Omnova Solutions Inc. | Mold runner for prevention of in-mold coating flow |
| US6863981B2 (en) * | 2002-05-31 | 2005-03-08 | Omnova Solutions Inc. | In-mold appearance coatings for nylon and nylon based thermoplastic substrates |
| AU2003263791A1 (en) * | 2002-08-09 | 2004-02-25 | General Motors Corporation | Gel coat composition |
| WO2004014990A1 (en) * | 2002-08-10 | 2004-02-19 | Omnova Solutions Inc. | Method for coating molded thermoplastic articles |
| US20070001343A1 (en) * | 2002-08-12 | 2007-01-04 | Valspar Sourcing, Inc. | Blush-resistant marine gel coat composition |
| CA2494031C (en) * | 2002-08-12 | 2009-09-29 | Valspar Sourcing, Inc. | Urethane acrylate gel coat resin and method of making |
| CA2496490C (en) * | 2002-08-23 | 2009-08-18 | Mitsui Chemicals, Inc. | In-mold coating molded article and process for preparing the same |
| WO2004048076A2 (en) | 2002-11-22 | 2004-06-10 | Omnova Solutions Inc. | Method for modifying existing injection mould machines to utilize an in-mould coating apparatus |
| WO2004052615A1 (en) * | 2002-12-10 | 2004-06-24 | Omnova Solutions Inc. | Method of in-mould coating an injection-moulded article incorporating positioning of the article prior to coating |
| ATE410287T1 (de) | 2002-12-12 | 2008-10-15 | Omnova Solutions Inc | Verfahren zur fertigung und verwendung eines werkzeuges |
| US20040148051A1 (en) * | 2003-01-28 | 2004-07-29 | Omnova Solutions, Inc. | Modeling method and program for in-mold coating an injection molded thermoplastic article |
| WO2004085549A2 (en) * | 2003-03-19 | 2004-10-07 | Omnova Solutions Inc. | Optical quality coating |
| CA2520185A1 (en) * | 2003-03-27 | 2004-11-04 | Omnova Solutions Inc. | Coating in multiple injection molding part cavities |
| US20050156351A1 (en) * | 2004-01-20 | 2005-07-21 | Omnova Solutions, Inc. | Apparatus and method for in-mold coating an article by injecting an in-mold coating through the article |
| US7257520B2 (en) * | 2004-04-30 | 2007-08-14 | Omnova Solutions, Inc. | Method and system for in-mold coating flow simulation |
| US20060118999A1 (en) * | 2004-12-06 | 2006-06-08 | Bayer Materialscience Llc | Method of preparing a coated molded article |
| US7314590B2 (en) * | 2005-09-20 | 2008-01-01 | Bayer Materialscience Llc | Method of preparing a coated molded plastic article |
| US20080230949A1 (en) * | 2007-03-23 | 2008-09-25 | Paul Razgunas | Injection molding process for forming coated molded parts |
| EP2139660B1 (en) * | 2007-04-27 | 2013-12-25 | Exatec, LLC. | Abrasion resistant plastic glazing with in-mold coating |
| CN101679656B (zh) | 2007-05-01 | 2012-10-03 | 埃克阿泰克有限责任公司 | 封装的塑料板及其制备方法 |
| WO2008141136A1 (en) * | 2007-05-09 | 2008-11-20 | Exatec. Llc | Pre-dry treatment of ink in decorative plastic glazing |
| US8088318B2 (en) * | 2007-06-05 | 2012-01-03 | Magna International Inc. | Method for processing an interior trim component |
| WO2009126051A1 (en) * | 2008-04-08 | 2009-10-15 | Formway Furniture Limited | Injection moulding method |
| DE102008001855A1 (de) * | 2008-05-19 | 2009-11-26 | Evonik Degussa Gmbh | Zweikomponenten-Zusammensetzung zur Herstellung von flexiblen Polyurethan-Gelcoats |
| JP5253200B2 (ja) * | 2009-01-22 | 2013-07-31 | 大日本塗料株式会社 | 型内被覆組成物及び型内被覆成形体 |
| DE102010025958A1 (de) * | 2010-07-02 | 2012-01-05 | Leibniz-Institut Für Polymerforschung Dresden E.V. | Verfahren zur Modifizierung von Kunststoffoberflächen |
| JP5771061B2 (ja) * | 2011-05-02 | 2015-08-26 | 帝人株式会社 | 皮膜を有する熱可塑性炭素繊維複合材料の製造方法 |
| ES2879637T3 (es) * | 2015-03-23 | 2021-11-22 | Dow Global Technologies Llc | Composiciones fotocurables para impresión tridimensional |
| JP7130848B2 (ja) | 2019-03-28 | 2022-09-05 | 帝人株式会社 | プレス成形体の製造方法 |
| CN112029358B (zh) * | 2020-09-16 | 2022-01-07 | Ppg涂料(天津)有限公司 | 水性面漆组合物 |
| EP4269061A4 (en) | 2020-12-23 | 2024-11-20 | Kansai Paint Co., Ltd | COATING MATERIAL COMPOSITION |
| EP4491676A1 (en) | 2022-03-10 | 2025-01-15 | Kansai Paint Co., Ltd. | Thermosetting coating material composition, coated article, and in-mold coating method |
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| US4081578A (en) | 1974-06-27 | 1978-03-28 | The General Tire & Rubber Company | In-mold coating composition and method of applying same |
| US4076788A (en) | 1976-12-02 | 1978-02-28 | General Motors Corporation | Mold coating of freshly molded articles |
| US4242415A (en) * | 1978-12-26 | 1980-12-30 | Ici Americas Inc. | In-mold coating compositions containing functional group terminated liquid polymers |
| US4189517A (en) | 1978-11-08 | 1980-02-19 | The General Tire & Rubber Company | Low-shrink in-mold coating |
| US4222929A (en) | 1978-11-08 | 1980-09-16 | The General Tire & Rubber Company | Low-shrink in-mold coating |
| NL7903428A (nl) | 1979-05-02 | 1980-11-04 | Stamicarbon | Werkwijze voor het vervaardigen van uit thermohardende hars gevormde voorwerpen. |
| US4350739A (en) | 1979-07-30 | 1982-09-21 | International Telephone And Telegraph Corporation | Molded plastic part |
| US4245006A (en) * | 1979-05-18 | 1981-01-13 | The General Tire & Rubber Company | Low-pressure low-temperature in-mold coating method |
| US4239796A (en) | 1979-06-21 | 1980-12-16 | The General Tire & Rubber Company | In-mold coating of structural foams and resultant product |
| US4366109A (en) | 1980-05-01 | 1982-12-28 | Freeman Chemical Corporation | Method for making coated molded articles |
| US4331735A (en) | 1980-06-26 | 1982-05-25 | The General Tire & Rubber Company | One component in-mold coating |
| US4356230A (en) * | 1980-07-10 | 1982-10-26 | International Telephone And Telegraph Corporation | Molded plastic product having a plastic substrate containing a filler and an in-mold plastic coating firmly bonded thereon and a process for its manufacture |
| US4414173A (en) | 1981-11-02 | 1983-11-08 | The General Tire & Rubber Company | In-mold coating |
| US4515710A (en) | 1983-07-18 | 1985-05-07 | Gencorp Inc. | In-mold coating composition |
| US4668460A (en) | 1985-04-02 | 1987-05-26 | The Sherwin-Williams Company | Method of molding and coating a substrate in a mold. |
| JPS62227712A (ja) | 1986-03-31 | 1987-10-06 | Toyo Seikan Kaisha Ltd | オレフィン―ビニルアルコール共重合体の射出成形体及びその製法 |
| US4808361A (en) * | 1987-03-16 | 1989-02-28 | Gencorp Inc. | Method for forming an in-mold coated fiber reinforced part |
| DE3736280A1 (de) | 1987-10-27 | 1989-05-11 | Roehm Gmbh | Verfahren zur herstellung kratzfest beschichteter extrudierter kunststoffbahnen |
| DE3811112A1 (de) | 1988-03-31 | 1989-10-12 | Fritz Mueller | Spritzgussverfahren fuer kunststoffe und spritzgussform |
| DE3816855A1 (de) | 1988-05-18 | 1989-11-23 | Roehm Gmbh | Verfahren zur herstellung kratzfest beschichteter kunststoffbahnen |
| US5084353A (en) | 1989-05-12 | 1992-01-28 | Gencorp Inc. | Thermosetting in-mold coating compositions |
| JPH03178412A (ja) * | 1989-12-07 | 1991-08-02 | Mazda Motor Corp | インモールドコート方法 |
| US5132052A (en) | 1991-03-20 | 1992-07-21 | Gencorp Inc. | Fast cure in-mold coating |
| JP2686682B2 (ja) | 1991-10-16 | 1997-12-08 | いすゞ自動車株式会社 | 成形品の製造方法 |
| BR9207085A (pt) | 1992-02-21 | 1995-12-12 | Du Pont | Processo de preparação de uma estrutura compósita reforçada reciclável com aspecto superficial melhorado e estruturas compósitas obtidas |
| GB9204730D0 (en) | 1992-03-05 | 1992-04-15 | Rover Group | A method of forming a moulding by dual injection and a moulding formed in accordance with such a method |
| JPH05301251A (ja) | 1992-04-24 | 1993-11-16 | Aisin Seiki Co Ltd | 熱可塑性樹脂の金型内塗装方法 |
| US5906788A (en) | 1992-10-05 | 1999-05-25 | Cook Composites And Polymers Co. | Dual cure, in-mold process for manufacturing abrasion resistant, coated thermoplastic articles |
| DE69408195T2 (de) | 1993-04-26 | 1998-11-05 | Gencorp Inc | Leitfähige Formbeschichtungen |
| JPH08227637A (ja) | 1994-02-23 | 1996-09-03 | Matsushita Electric Works Ltd | コントロールスイッチ及びその製造方法 |
| DE4414258C2 (de) | 1994-04-23 | 1996-07-25 | Battenfeld Gmbh | Verfahren zum Spritzgießen von mindestens aus zwei unterschiedlichen Schichten bestehenden Gegenständen |
| US5902534A (en) | 1994-09-21 | 1999-05-11 | Mitsubishi Engineering-Plastics Corp. | Method of injection-molding thermoplastic resins |
| JP3406435B2 (ja) * | 1994-09-21 | 2003-05-12 | 三菱エンジニアリングプラスチックス株式会社 | 熱可塑性樹脂の射出成形方法 |
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| US5658672A (en) | 1995-05-08 | 1997-08-19 | Gencorp Inc. | In-mold coating composition |
| US5777053A (en) | 1997-01-17 | 1998-07-07 | Gencorp Inc. | In-mold coating compositions suitable as is for an end use application |
| US6180043B1 (en) | 1998-01-27 | 2001-01-30 | Dai Nippon Toryo Co., Ltd. | Method of in-mold coating |
| BR0110155A (pt) | 2000-04-20 | 2002-12-31 | Decoma Exterior Trim Inc | Método para fabricar uma peça moldada, e, molde para fabricar uma peça moldada |
-
2000
- 2000-07-12 US US09/614,953 patent/US6617033B1/en not_active Expired - Lifetime
-
2001
- 2001-06-26 AT AT01948715T patent/ATE362831T1/de not_active IP Right Cessation
- 2001-06-26 MX MXPA03000375A patent/MXPA03000375A/es unknown
- 2001-06-26 JP JP2002508623A patent/JP4729141B2/ja not_active Expired - Fee Related
- 2001-06-26 EP EP01948715A patent/EP1299218B1/en not_active Expired - Lifetime
- 2001-06-26 KR KR10-2003-7000426A patent/KR20040002837A/ko not_active Withdrawn
- 2001-06-26 WO PCT/US2001/020251 patent/WO2002004187A2/en not_active Ceased
- 2001-06-26 DE DE60128568T patent/DE60128568T2/de not_active Expired - Lifetime
- 2001-06-26 CA CA2438672A patent/CA2438672C/en not_active Expired - Lifetime
-
2002
- 2002-05-02 US US10/137,981 patent/US6875389B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA03000375A (es) | 2004-05-05 |
| WO2002004187A2 (en) | 2002-01-17 |
| DE60128568T2 (de) | 2008-01-31 |
| CA2438672A1 (en) | 2003-07-13 |
| EP1299218A2 (en) | 2003-04-09 |
| US6617033B1 (en) | 2003-09-09 |
| US6875389B2 (en) | 2005-04-05 |
| KR20040002837A (ko) | 2004-01-07 |
| US20020171171A1 (en) | 2002-11-21 |
| WO2002004187A3 (en) | 2002-03-14 |
| EP1299218B1 (en) | 2007-05-23 |
| JP4729141B2 (ja) | 2011-07-20 |
| ATE362831T1 (de) | 2007-06-15 |
| DE60128568D1 (de) | 2007-07-05 |
| JP2004502570A (ja) | 2004-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20210628 |