JPH11505274A - 変性アクリル共重合体 - Google Patents
変性アクリル共重合体Info
- Publication number
- JPH11505274A JPH11505274A JP8527169A JP52716996A JPH11505274A JP H11505274 A JPH11505274 A JP H11505274A JP 8527169 A JP8527169 A JP 8527169A JP 52716996 A JP52716996 A JP 52716996A JP H11505274 A JPH11505274 A JP H11505274A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- acrylic copolymer
- copolymer according
- group
- 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.)
- Granted
Links
- 229920006243 acrylic copolymer Polymers 0.000 title claims abstract description 97
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 35
- -1 polycyclic aliphatic compound Chemical class 0.000 claims abstract description 35
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 34
- 229920001577 copolymer Polymers 0.000 claims abstract description 14
- 238000000576 coating method Methods 0.000 claims description 62
- 239000011248 coating agent Substances 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 31
- 239000004922 lacquer Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 20
- 150000008065 acid anhydrides Chemical class 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 14
- 150000008064 anhydrides Chemical class 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000008199 coating composition Substances 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- 229920000058 polyacrylate Polymers 0.000 claims description 5
- 239000006096 absorbing agent Substances 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 150000002596 lactones Chemical class 0.000 claims description 4
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000025 natural resin Substances 0.000 claims description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 3
- PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 claims description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 2
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical class C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 2
- FKZJBAXKHJIQDU-UHFFFAOYSA-N perhydro-4,7-methanoinden-5-ol Chemical compound C12CCCC2C2CC(O)C1C2 FKZJBAXKHJIQDU-UHFFFAOYSA-N 0.000 claims description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 239000013008 thixotropic agent Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
- YPGLTKHJEQHKSS-ASZLNGMRSA-N (1r,4ar,4bs,7r,8as,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@H](C(C)C)C[C@@H]2CC1 YPGLTKHJEQHKSS-ASZLNGMRSA-N 0.000 claims 1
- YRCGAHTZOXPQPR-UHFFFAOYSA-N 2-ethylnonanoic acid Chemical compound CCCCCCCC(CC)C(O)=O YRCGAHTZOXPQPR-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003973 paint Substances 0.000 abstract description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 32
- 238000004519 manufacturing process Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000005056 polyisocyanate Substances 0.000 description 13
- 229920001228 polyisocyanate Polymers 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 10
- 229920003180 amino resin Polymers 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 3
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229920006305 unsaturated polyester Polymers 0.000 description 3
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical class C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- FIWHJQPAGLNURC-UHFFFAOYSA-N oxiran-2-ylmethyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OCC1CO1 FIWHJQPAGLNURC-UHFFFAOYSA-N 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N pyridinedicarboxylic acid Natural products OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- YHUVMHKAHWKQBI-UHFFFAOYSA-N quinoline-2,3-dicarboxylic acid Chemical compound C1=CC=C2N=C(C(O)=O)C(C(=O)O)=CC2=C1 YHUVMHKAHWKQBI-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- MAZWDMBCPDUFDJ-UHFFFAOYSA-N trans-Traumatinsaeure Natural products OC(=O)CCCCCCCCC=CC(O)=O MAZWDMBCPDUFDJ-UHFFFAOYSA-N 0.000 description 1
- MAZWDMBCPDUFDJ-VQHVLOKHSA-N traumatic acid Chemical compound OC(=O)CCCCCCCC\C=C\C(O)=O MAZWDMBCPDUFDJ-VQHVLOKHSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
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- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/064—Copolymers with monomers not covered by C09D133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.20℃で少なくとも1.460の屈折率を有し、少なくとも二つの環を有 するカルボキシル基含有多環式脂肪族物質によってエポキシ基含有共重合体を変 性することによって得られたことを特徴とするアクリル共重合体。 2.カルボキシル基含有多環式脂肪族物質が少なくとも3個の環を有すること を特徴とする請求の範囲第1項記載のアクリル共重合体。 3.カルボキシル基対エポキシ基のモル比が0.5〜1.0、好ましくは0. 8〜1.0であることを特徴とする請求の範囲第1項又は第2項記載のアクリル 共重合体。 4.カルボキシル基対エポキシ基のモル比が0.8〜1.0、好ましくは0. 9〜1.0であることを特徴とする請求の範囲第1項又は第2項記載のアクリル 共重合体。 5.更に高温でポリカルボン酸及び/又はそれらの酸無水物と反応させてセミ エステルを形成することを特徴とする請求の範囲第4項記載のアクリル共重合体 。 6.アクリル重合体及びポリカルボン酸又はそれらの酸無水物の反応生成物が 、中和後反応生成物を水稀釈性にするのに充分な酸価を有することを特徴とする 請求の範囲第5項記載のアクリル共重合体。 7.水稀釈性反応生成物が、塩基、好ましくは三級アミンで中和することによ って得られることを特徴とする請求の範囲第6項記載のアクリル共重合体。 8.1個のカルボキシル基を含有する物質が、20℃で少なくとも1.480 の屈折率を有することを特徴とする請求の範囲第1項〜第7項のいずれか1項記 載のアクリル共重合体。 9.1個のカルボキシル基を含有する多環式脂肪族物質が、水素化天然樹脂酸 ;アダマンタンカルボン酸;及び例えばトリシクロ〔5.2.1.02,6〕デカ ン−8−カルボン酸の如きジシクロペンタジエンから誘導された三環式モノカル ボン酸;好ましくはテトラヒドロアビエチン酸からなる群から選択した三環式モ ノカルボン酸であることを特徴とする請求の範囲第1項〜第8項のいずれか1項 記載のアクリル共重合体。 10.1個のカルボキシル基含有多環式脂肪族物質が、少なくとも2種の化合物 の反応生成物であり、その少なくとも1種が20℃で少なくとも1.460、好 ましくは少なくとも1.480の屈折率を有する多環式脂肪族カルボン酸である ことを特徴とする請求の範囲第1項〜第9項の何れか1項記載のアクリル共重合 体。 11.20℃で少なくとも1.480の屈折率を有する多環式脂肪族化合物の少 なくとも1種が、1個のカルボキシル基含有多環式脂肪族反応生成物中に、少な くとも10重量%、好ましくは少なくとも20重量%、及び特に少なくとも50 重量%含有されていることを特徴とする請求の範囲第10項記載のアクリル共重 合体。 12.1個のカルボキシル基含有多環式脂肪族物質が、少なくとも1種のジカル ボン酸及び/又はその酸無水物とアルコールの1種又は混合物の反応生成物であ ることを特徴とする請求の範囲第10項又は第11項記載のアクリル共重合体。 13.アルコールが、パーヒドロアビエチルアルコール;ジシクロペンタジエン 誘導体例えば8−ヒドロキシトリシクロ〔5.2.1.02,6〕デカン、8−ヒ ドロキシメチルトリシクロ〔5.2.1.02,6〕デカン、8−ヒドロキシトリ シクロ〔5.2.1.02,6〕デセン−3、9−ヒドロキシトリシクロ〔5.2 .1.02,6〕デセン−3の如き過水素化天然樹脂からなる群から選択した三環 式脂肪族モノアルコールであることを特徴とする請求の範囲第12項記載のアク リル共重合体。 14.ジカルボン酸及びその酸無水物を、フタル酸、ヘキサヒドロフタル酸、テ トラヒドロフタル酸、メチルヘキサヒドロフタル酸、1,8−ナフタレンジカル ボン酸及びマレイン酸からなる群から選択することを特徴とする請求の範囲第1 2項又は第13項記載のアクリル共重合体。 15.1個のカルボキシル基含有多環式脂肪族物質が、追加的に芳香族化合物の 1種又は混合物を加有することを特徴とする請求の範囲第1項〜第14項の何れ か1項記載のアクリル共重合体。 16.芳香族化合物を、芳香族モノカルボン酸例えばナフトエ酸;ベンゼンモノ カルボン酸例えば安息香酸、o−トルイル酸、m−トルイル酸、p−トルイル酸 、ヒドロキシ安息香酸、t−ブチル安息香酸、芳香族複素環式モノカルボン酸例 えばピリジンカルボン酸、フランカルボン酸からなる群から選択することを特徴 とする請求の範囲第15項記載のアクリル共重合体。 17.エポキシ基含有共重合体が、少なくとも1個のエポキシ基を含有する化合 物の1種又は混合物、及び異なる単量体の1種又は混合物を有する少なくとも1 種のエチレン系不飽和基の重合によって得られたことを特徴とする請求の範囲第 1項〜第16項の何れか1項記載のアクリル共重合体。 18.少なくとも1個のエポキシ基及び少なくとも1個のエチレン系不飽和基を 含有する化合物が、アリルグリシジルエーテル又はグリシジル(メタ)アクリレ ートであることを特徴とする請求の範囲第17項記載のアクリル共重合体。 19.他の単量体が、アルキル(メタ)アクリレート、スチレン、ビニルトルエ ン、ポリプロピレングリコールモノ(メタ)アクリレート、ヒドロキシアルキル (メタ)アクリレート、及び/又はヒドロキシアルキル(メタ)アクリレートと ラクトン例えばε−カプロラクタムのヒドロキシル基含有反応生成物であること を特徴とする請求の範囲第17項又は第18項記載のアクリル共重合体。 20.追加的に、界面活性剤、流動学的助剤(SCA変性アクリル共重合体)、 増粘剤、チキソトロープ剤、促進剤、光安定剤(UV吸収剤、HALS化合物) 、重合開始剤、架橋剤、モノカルボン酸及び/又は別の結合剤を含有することを 特徴とする請求の範囲第1項〜第19項の何れか1項記載のアクリル共重合体。 21.被覆組成物としての請求の範囲第1項〜第20項の何れか1項記載のアク リル共重合体の用途。 22.粉末被覆の形での請求の範囲第1項〜第20項の何れか1項記載のアクリ ル共重合体の用途。 23.特に自動車工業における透明被覆としての請求の範囲第1項〜第20項の 何れか1項記載のアクリル共重合体の用途。 24.特に自動車工業における水性透明被覆としての請求の範囲第1項〜第20 項の何れか1項記載のアクリル共重合体の用途。 25.特に自動車工業における仕上ラッカーとしての請求の範囲第1項〜第20 項の何れか1項記載のアクリル共重合体の用途。 26.顔料化下塗ラッカーを適用し、下塗被覆を形成し、そして“湿式”法によ り請求の範囲第1項〜第20項の何れか1項記載のアクリル共重合体を含有する 透明被覆を適用し、二つのラッカーを共同で硬化することを特徴とする多層ラッ カー塗布を製造するための請求の範囲第1項〜第20項の何れか1項記載のアク リル共重合体の用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE19508544.2 | 1995-03-10 | ||
DE19508544A DE19508544A1 (de) | 1995-03-10 | 1995-03-10 | Modifiziertes Acrylcopolymerisat |
PCT/DE1996/000393 WO1996028478A1 (de) | 1995-03-10 | 1996-03-06 | Modifiziertes acrylcopolymerisat |
Publications (2)
Publication Number | Publication Date |
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JPH11505274A true JPH11505274A (ja) | 1999-05-18 |
JP3911291B2 JP3911291B2 (ja) | 2007-05-09 |
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Application Number | Title | Priority Date | Filing Date |
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JP52716996A Expired - Lifetime JP3911291B2 (ja) | 1995-03-10 | 1996-03-06 | 変性アクリル共重合体 |
Country Status (12)
Country | Link |
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US (1) | US6005056A (ja) |
EP (1) | EP0813552B1 (ja) |
JP (1) | JP3911291B2 (ja) |
KR (1) | KR100479575B1 (ja) |
AT (1) | ATE174935T1 (ja) |
AU (1) | AU710901B2 (ja) |
CA (1) | CA2214115A1 (ja) |
DE (2) | DE19508544A1 (ja) |
ES (1) | ES2127625T3 (ja) |
IN (1) | IN187841B (ja) |
MY (1) | MY112504A (ja) |
WO (1) | WO1996028478A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013053185A (ja) * | 2011-09-01 | 2013-03-21 | Arakawa Chem Ind Co Ltd | 塗料用バインダー |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19939738B4 (de) * | 1999-08-21 | 2016-03-17 | Alfred Krüger | Verfahren zur Herstellung von lagerstabilen modifizierten cycloaliphatischen Epoxidharzen und deren Verwendung |
FR2809109B1 (fr) * | 2000-05-17 | 2003-10-03 | Atofina | Polymeres ayant des fonctions hydroxyles sur les chaines laterales |
DE10059856A1 (de) | 2000-11-30 | 2002-07-18 | Bollig & Kemper Gmbh & Co Kg | Klarlackschicht |
DE10059853A1 (de) * | 2000-11-30 | 2002-07-18 | Bollig & Kemper Gmbh & Co Kg | Beschichtungszusammensetzung |
EP1682589A1 (en) * | 2003-11-12 | 2006-07-26 | Showa Denko K.K. | Curable polymer compound |
US20060078740A1 (en) * | 2004-10-07 | 2006-04-13 | Zern John R | Barrier coatings |
KR101820581B1 (ko) * | 2015-12-30 | 2018-01-22 | 주식회사 케이씨씨 | 전착도료용 아크릴계 공중합체 및 그 제조방법 |
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US2857345A (en) * | 1953-10-01 | 1958-10-21 | Smith Paper Mills Ltd Howard | Method of using lignin for introducing water into vulcanizable compositions |
GB793776A (en) * | 1954-04-07 | 1958-04-23 | Ici Ltd | Esters of drying oil acids with certain vinyl polymers |
US2857354A (en) * | 1955-07-20 | 1958-10-21 | Du Pont | Process of making glycidyl methacrylate polymer composition containing same, and product coated therewith |
US3939128A (en) * | 1971-06-30 | 1976-02-17 | American Cyanamid Company | Vulcanization of halogen or epoxy-containing polyacrylate elastomers |
US3752870A (en) * | 1971-08-16 | 1973-08-14 | Ford Motor Co | Powder coating compositions containing polymer of ethylenically unsaturated glycidyl esters dicarboxylic acids and flow control agents |
AT307042B (de) * | 1971-10-05 | 1973-05-10 | Vianova Kunstharz Ag | Verfahren zur Herstellung von in aliphatischen Lösungsmitteln löslichen, oxydativ trocknenden Kunstharzen |
JPS511535A (ja) * | 1974-06-04 | 1976-01-08 | Kansai Paint Co Ltd | |
JPS51125115A (en) * | 1974-11-11 | 1976-11-01 | Dainippon Ink & Chem Inc | Thermosetting resin composition for use in powder coating |
US4883838A (en) * | 1985-09-30 | 1989-11-28 | Basf Lacke & Farben Ag | Soluble acrylate copolymer containing carboxyl groups, processes for its preparation and coating agents based on the acrylate copolymer |
DE3534858A1 (de) * | 1985-09-30 | 1987-04-02 | Basf Lacke & Farben | Loesliches carboxylgruppenhaltiges acrylatcopolymerisat, verfahren zu seiner herstellung und ueberzugsmittel auf der basis des acrylatcopolymerisats |
EP0355892B1 (en) * | 1988-08-09 | 1995-01-18 | Akzo Nobel N.V. | Coating composition |
US5177152A (en) * | 1988-08-09 | 1993-01-05 | Akzo N.V. | Water-dilutable, crosslinkable binder resin |
JP2893875B2 (ja) * | 1990-06-20 | 1999-05-24 | ジェイエスアール株式会社 | 保護膜形成用材料 |
US5116892A (en) * | 1991-07-22 | 1992-05-26 | Eastman Kodak Company | Thermosetting powder coating compositions |
DE4337855A1 (de) * | 1993-11-05 | 1995-05-11 | Bayer Ag | Pulverlack und seine Verwendung |
-
1995
- 1995-03-10 DE DE19508544A patent/DE19508544A1/de not_active Withdrawn
-
1996
- 1996-03-06 KR KR1019970706281A patent/KR100479575B1/ko not_active IP Right Cessation
- 1996-03-06 CA CA002214115A patent/CA2214115A1/en not_active Abandoned
- 1996-03-06 DE DE59601050T patent/DE59601050D1/de not_active Expired - Lifetime
- 1996-03-06 ES ES96904741T patent/ES2127625T3/es not_active Expired - Lifetime
- 1996-03-06 AT AT96904741T patent/ATE174935T1/de active
- 1996-03-06 AU AU48748/96A patent/AU710901B2/en not_active Ceased
- 1996-03-06 US US08/913,142 patent/US6005056A/en not_active Expired - Lifetime
- 1996-03-06 WO PCT/DE1996/000393 patent/WO1996028478A1/de active IP Right Grant
- 1996-03-06 JP JP52716996A patent/JP3911291B2/ja not_active Expired - Lifetime
- 1996-03-06 EP EP96904741A patent/EP0813552B1/de not_active Expired - Lifetime
- 1996-03-07 IN IN416CA1996 patent/IN187841B/en unknown
- 1996-03-08 MY MYPI96000848A patent/MY112504A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013053185A (ja) * | 2011-09-01 | 2013-03-21 | Arakawa Chem Ind Co Ltd | 塗料用バインダー |
Also Published As
Publication number | Publication date |
---|---|
ATE174935T1 (de) | 1999-01-15 |
KR100479575B1 (ko) | 2005-05-16 |
ES2127625T3 (es) | 1999-04-16 |
WO1996028478A1 (de) | 1996-09-19 |
EP0813552A1 (de) | 1997-12-29 |
CA2214115A1 (en) | 1996-09-19 |
MY112504A (en) | 2001-06-30 |
JP3911291B2 (ja) | 2007-05-09 |
DE59601050D1 (de) | 1999-02-04 |
US6005056A (en) | 1999-12-21 |
IN187841B (ja) | 2002-07-06 |
KR19980702873A (ko) | 1998-08-05 |
DE19508544A1 (de) | 1996-09-12 |
AU710901B2 (en) | 1999-09-30 |
AU4874896A (en) | 1996-10-02 |
EP0813552B1 (de) | 1998-12-23 |
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