DE69323787T2 - UV-härtende, verschleissfeste Beschichtungszusammensetzung - Google Patents
UV-härtende, verschleissfeste BeschichtungszusammensetzungInfo
- Publication number
- DE69323787T2 DE69323787T2 DE69323787T DE69323787T DE69323787T2 DE 69323787 T2 DE69323787 T2 DE 69323787T2 DE 69323787 T DE69323787 T DE 69323787T DE 69323787 T DE69323787 T DE 69323787T DE 69323787 T2 DE69323787 T2 DE 69323787T2
- Authority
- DE
- Germany
- Prior art keywords
- component
- meth
- groups
- monomer
- parts
- 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
Links
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- 238000003848 UV Light-Curing Methods 0.000 title description 5
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- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 33
- -1 acryloxyethyl Chemical group 0.000 claims description 28
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- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 17
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- PJIFJEUHCQYNHO-UHFFFAOYSA-N diethoxy-(3-isocyanatopropyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CCCN=C=O PJIFJEUHCQYNHO-UHFFFAOYSA-N 0.000 claims description 3
- IHZHYITXFSSZIZ-UHFFFAOYSA-N 2-isocyanatoethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCN=C=O IHZHYITXFSSZIZ-UHFFFAOYSA-N 0.000 claims description 2
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- VNNPFQQFUFDPJM-UHFFFAOYSA-N diethoxy-(2-isocyanatoethyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CCN=C=O VNNPFQQFUFDPJM-UHFFFAOYSA-N 0.000 claims description 2
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- KEIBTGABMNALIT-UHFFFAOYSA-N triethoxy(2-isocyanatoethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCN=C=O KEIBTGABMNALIT-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000243 solution Substances 0.000 description 16
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- 238000006243 chemical reaction Methods 0.000 description 15
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- 230000001070 adhesive effect Effects 0.000 description 11
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 8
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- QNRSQFWYPSFVPW-UHFFFAOYSA-N 5-(4-cyanobutyldiazenyl)pentanenitrile Chemical compound N#CCCCCN=NCCCCC#N QNRSQFWYPSFVPW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000007754 air knife coating Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000005250 beta ray Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/147—Polyurethanes; Polyureas
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/148—Polysiloxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP08392992A JP3164407B2 (ja) | 1992-04-06 | 1992-04-06 | 耐摩耗性紫外線硬化性被覆組成物 |
| JP24776792A JP3164431B2 (ja) | 1992-09-17 | 1992-09-17 | 耐摩耗性紫外線硬化性被覆組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69323787D1 DE69323787D1 (de) | 1999-04-15 |
| DE69323787T2 true DE69323787T2 (de) | 1999-07-29 |
Family
ID=26424964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69323787T Expired - Lifetime DE69323787T2 (de) | 1992-04-06 | 1993-04-06 | UV-härtende, verschleissfeste Beschichtungszusammensetzung |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US5378735A (enExample) |
| EP (1) | EP0565044B1 (enExample) |
| DE (1) | DE69323787T2 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10502961A (ja) * | 1994-07-13 | 1998-03-17 | アライドシグナル・インコーポレーテッド | ビニルエーテル基剤コーティング系用安定剤 |
| US5539014A (en) * | 1994-07-13 | 1996-07-23 | Alliedsignal Inc. | Adhesion promoters for vinyl ether-based coating systems |
| US6562268B1 (en) | 1995-12-21 | 2003-05-13 | Davidson Textron, Inc | Interior trim panels and method for manufacturing such panels using silaceous materials |
| JP3972347B2 (ja) * | 1997-03-28 | 2007-09-05 | Ｊｓｒ株式会社 | 液状硬化性樹脂組成物 |
| JP3792339B2 (ja) * | 1997-04-03 | 2006-07-05 | 三菱化学株式会社 | 活性エネルギー線硬化性被覆組成物 |
| JP4016409B2 (ja) * | 1997-12-12 | 2007-12-05 | Ｊｓｒ株式会社 | 液状硬化性樹脂組成物 |
| US6248225B1 (en) | 1998-05-26 | 2001-06-19 | Ppg Industries Ohio, Inc. | Process for forming a two-coat electrodeposited composite coating the composite coating and chip resistant electrodeposited coating composition |
| US6423425B1 (en) | 1998-05-26 | 2002-07-23 | Ppg Industries Ohio, Inc. | Article having a chip-resistant electrodeposited coating and a process for forming an electrodeposited coating |
| DE19856000A1 (de) | 1998-12-04 | 2000-06-15 | Bayer Ag | Hybridlack-Zubereitung |
| US6623791B2 (en) | 1999-07-30 | 2003-09-23 | Ppg Industries Ohio, Inc. | Coating compositions having improved adhesion, coated substrates and methods related thereto |
| US6387519B1 (en) | 1999-07-30 | 2002-05-14 | Ppg Industries Ohio, Inc. | Cured coatings having improved scratch resistance, coated substrates and methods thereto |
| MX252994B (es) | 1999-07-30 | 2008-01-07 | Ppg Ind Ohio Inc | Composiciones de recubrimiento que tienen una mejor resistencia a las raspaduras, sustratos recubiertos, y metodos relacionados con los mismo. |
| CN1209427C (zh) | 1999-07-30 | 2005-07-06 | 匹兹堡玻璃板工业俄亥俄股份有限公司 | 具有改进抗刮性的涂料组合物、涂覆基材及其有关方法 |
| US6610777B1 (en) | 1999-07-30 | 2003-08-26 | Ppg Industries Ohio, Inc. | Flexible coating compositions having improved scratch resistance, coated substrates and methods related thereto |
| WO2001012738A1 (fr) * | 1999-08-10 | 2001-02-22 | Tdk Corporation | Composition d'enduction pour formation d'un revetement dur sur des substrats au polycarbonate, film au polycarbonate pourvu d'une couche de revetement dur et moulage au polycarbonate pourvu d'une couche de revetement dur |
| US20050017384A1 (en) * | 1999-11-11 | 2005-01-27 | Kiminori Tamai | Substrate for optical disk provided with hard-coating layer and method of producing the same |
| US6635341B1 (en) | 2000-07-31 | 2003-10-21 | Ppg Industries Ohio, Inc. | Coating compositions comprising silyl blocked components, coating, coated substrates and methods related thereto |
| KR100836140B1 (ko) * | 2001-02-23 | 2008-06-09 | 니폰 가야꾸 가부시끼가이샤 | 배향막용 자외선경화형 수지조성물 및 액정성 화합물을갖는 고분자 필름을 포함하는 위상차 필름 |
| US7420005B2 (en) * | 2001-06-28 | 2008-09-02 | Dai Nippon Printing Co., Ltd. | Photocurable resin composition, finely embossed pattern-forming sheet, finely embossed transfer sheet, optical article, stamper and method of forming finely embossed pattern |
| US20060191145A1 (en) * | 2001-08-24 | 2006-08-31 | Waddington North America, Inc. | Metallized cutlery and tableware and method therefor |
| DE60232942D1 (de) * | 2001-10-09 | 2009-08-27 | Mitsubishi Chem Corp | Strahlungshärtbare Beschichtungszusammensetzung |
| DE10232828A1 (de) * | 2002-07-19 | 2004-02-05 | Goldschmidt Ag | Verwendung von Antioxidantien in strahlenhärtbaren Beschichtungsmassen für die Herstellung von abhäsiven Beschichtungen |
| US20040191498A1 (en) * | 2003-03-27 | 2004-09-30 | Daniela White | Polymerizable modified particles and methods of using the same |
| US7196136B2 (en) * | 2004-04-29 | 2007-03-27 | Hewlett-Packard Development Company, L.P. | UV curable coating composition |
| US7183353B2 (en) * | 2004-04-29 | 2007-02-27 | Hewlett-Packard Development Company, L.P. | UV curable coating composition |
| TWI317444B (en) * | 2004-09-03 | 2009-11-21 | Eternal Chemical Co Ltd | Optical film having high hardness and use thereof |
| US7375144B2 (en) * | 2005-06-16 | 2008-05-20 | Eastman Chemical Company | Abrasion resistant coatings |
| JP5333443B2 (ja) * | 2008-03-27 | 2013-11-06 | 藤倉化成株式会社 | プラスチック基材用塗料組成物、それより形成された塗膜、および形成体 |
| CN102186861B (zh) | 2008-10-15 | 2014-04-16 | 关西涂料株式会社 | 具有聚合官能团的倍半硅氧烷化合物 |
| KR101248743B1 (ko) * | 2010-04-08 | 2013-04-03 | (주)엘지하우시스 | 성형가공 후에도 높은 광택을 가지는 성형용 적층시트 및 그 제조방법 |
| CN102070981B (zh) * | 2010-12-02 | 2012-07-04 | 广州慧谷化学有限公司 | 一种紫外光固化涂料及其制备方法与应用 |
| KR101447775B1 (ko) * | 2012-05-08 | 2014-10-06 | (주)엘지하우시스 | 감촉 특성이 우수한 코팅 조성물, 그 제조방법 및 이를 이용한 전사시트 |
| JP6491311B2 (ja) | 2014-03-17 | 2019-03-27 | ダウ シリコーンズ コーポレーション | フッ素化化合物、該化合物を含む硬化性組成物、及び硬化物 |
| JP6595496B2 (ja) | 2014-03-17 | 2019-10-23 | ダウ シリコーンズ コーポレーション | 硬化性組成物、該硬化性組成物から形成される硬化物、及び該硬化物の形成方法 |
| US9315695B2 (en) * | 2014-06-26 | 2016-04-19 | Dymax Corporation | Actinic radiation and moisture dual curable composition |
| KR101746460B1 (ko) * | 2015-11-20 | 2017-06-13 | 현대자동차주식회사 | 폴리카보네이트 글레이징용 코팅도료 조성물로 코팅된 도장품 |
| CN114477785A (zh) * | 2022-02-17 | 2022-05-13 | 苏州卡吉德化学科技有限公司 | 一种玻璃表面超亲水涂层及制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4027073A (en) * | 1974-06-25 | 1977-05-31 | Dow Corning Corporation | Pigment-free coating compositions |
| DE2963907D1 (en) * | 1979-01-05 | 1982-11-25 | Ici Plc | Dispersions of siliceous solids in liquid organic media |
| US4348462A (en) * | 1980-07-11 | 1982-09-07 | General Electric Company | Abrasion resistant ultraviolet light curable hard coating compositions |
| US4478876A (en) * | 1980-12-18 | 1984-10-23 | General Electric Company | Process of coating a substrate with an abrasion resistant ultraviolet curable composition |
| US4455205A (en) * | 1981-06-01 | 1984-06-19 | General Electric Company | UV Curable polysiloxane from colloidal silica, methacryloyl silane, diacrylate, resorcinol monobenzoate and photoinitiator |
| JPS5925840A (ja) * | 1982-08-05 | 1984-02-09 | Mitsui Petrochem Ind Ltd | 被覆用硬化型樹脂組成物 |
| JPS62249992A (ja) * | 1986-04-24 | 1987-10-30 | Nippon Kayaku Co Ltd | 新規なシリコンウレタン（メタ）アクリレ−ト，これを用いた樹脂組成物およびコ−テイング剤 |
| CA2018237C (en) * | 1989-07-14 | 2000-05-09 | Antony P. Wright | Radiation curable acryloxyfunctional silicone coating composition |
| CA2023923A1 (en) * | 1989-09-05 | 1991-03-06 | Anthony Revis | Radiation curable transparent coating compositions containing basic colloidal silica |
| US5242719A (en) * | 1992-04-06 | 1993-09-07 | General Electric Company | Abrasion resistant UV-curable hardcoat compositions |
-
1993
- 1993-04-06 DE DE69323787T patent/DE69323787T2/de not_active Expired - Lifetime
- 1993-04-06 EP EP93105670A patent/EP0565044B1/en not_active Expired - Lifetime
- 1993-04-06 US US08/043,522 patent/US5378735A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5378735A (en) | 1995-01-03 |
| EP0565044A2 (en) | 1993-10-13 |
| EP0565044A3 (enExample) | 1994-01-19 |
| DE69323787D1 (de) | 1999-04-15 |
| EP0565044B1 (en) | 1999-03-10 |
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