SE437151B - Monomerkompositioner samt anvendning derav - Google Patents
Monomerkompositioner samt anvendning deravInfo
- Publication number
- SE437151B SE437151B SE7806632A SE7806632A SE437151B SE 437151 B SE437151 B SE 437151B SE 7806632 A SE7806632 A SE 7806632A SE 7806632 A SE7806632 A SE 7806632A SE 437151 B SE437151 B SE 437151B
- Authority
- SE
- Sweden
- Prior art keywords
- monomer
- acid
- oil
- composition according
- component
- Prior art date
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 294
- 239000000203 mixture Substances 0.000 title claims abstract description 257
- 229920000642 polymer Polymers 0.000 claims abstract description 117
- 238000000576 coating method Methods 0.000 claims abstract description 91
- 229920001577 copolymer Polymers 0.000 claims abstract description 54
- 239000011248 coating agent Substances 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000003921 oil Substances 0.000 claims description 93
- 235000019198 oils Nutrition 0.000 claims description 92
- -1 C1-C20-alkyl fumarate Chemical compound 0.000 claims description 89
- 238000001035 drying Methods 0.000 claims description 71
- 229920000180 alkyd Polymers 0.000 claims description 57
- 229920002554 vinyl polymer Polymers 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 42
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 41
- 239000002274 desiccant Substances 0.000 claims description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 30
- 229920000728 polyester Polymers 0.000 claims description 29
- 239000000047 product Substances 0.000 claims description 29
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 26
- 239000005056 polyisocyanate Substances 0.000 claims description 25
- 229920001228 polyisocyanate Polymers 0.000 claims description 25
- 239000003381 stabilizer Substances 0.000 claims description 23
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000000194 fatty acid Substances 0.000 claims description 21
- 239000012948 isocyanate Substances 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 20
- 229930195729 fatty acid Natural products 0.000 claims description 20
- 150000003839 salts Chemical group 0.000 claims description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 150000002513 isocyanates Chemical class 0.000 claims description 18
- 150000004665 fatty acids Chemical class 0.000 claims description 17
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims description 17
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
- 239000000944 linseed oil Substances 0.000 claims description 14
- 235000021388 linseed oil Nutrition 0.000 claims description 14
- 229920000570 polyether Polymers 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 229910017052 cobalt Inorganic materials 0.000 claims description 13
- 239000010941 cobalt Substances 0.000 claims description 13
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 239000004814 polyurethane Substances 0.000 claims description 10
- 229920002635 polyurethane Polymers 0.000 claims description 10
- 239000003549 soybean oil Substances 0.000 claims description 9
- 235000012424 soybean oil Nutrition 0.000 claims description 9
- 229920001169 thermoplastic Polymers 0.000 claims description 9
- 239000004416 thermosoftening plastic Substances 0.000 claims description 9
- 239000002023 wood Substances 0.000 claims description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 8
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 8
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims description 8
- 239000004359 castor oil Substances 0.000 claims description 7
- 235000019438 castor oil Nutrition 0.000 claims description 7
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 239000005062 Polybutadiene Substances 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- 229920002857 polybutadiene Polymers 0.000 claims description 6
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims description 6
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 5
- DMJZWFZICOEEAJ-UHFFFAOYSA-N 2-(4-bromothiophen-3-yl)sulfanylpropanoic acid Chemical compound OC(=O)C(C)SC1=CSC=C1Br DMJZWFZICOEEAJ-UHFFFAOYSA-N 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 235000005713 safflower oil Nutrition 0.000 claims description 5
- 239000003813 safflower oil Substances 0.000 claims description 5
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 4
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 235000019485 Safflower oil Nutrition 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- 229920001195 polyisoprene Polymers 0.000 claims description 4
- 239000003784 tall oil Substances 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- 241000273930 Brevoortia tyrannus Species 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920002614 Polyether block amide Polymers 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- 238000005304 joining Methods 0.000 claims description 3
- WHXCGIRATPOBAY-UHFFFAOYSA-N n-hexan-2-ylidenehydroxylamine Chemical compound CCCCC(C)=NO WHXCGIRATPOBAY-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 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
- GTVITUZSWANKRK-UHFFFAOYSA-N propan-2-yloxycyclododecane Chemical compound CC(C)OC1CCCCCCCCCCC1 GTVITUZSWANKRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000011342 resin composition Substances 0.000 claims description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 2
- CWNNYYIZGGDCHS-UHFFFAOYSA-N 2-methylideneglutaric acid Chemical compound OC(=O)CCC(=C)C(O)=O CWNNYYIZGGDCHS-UHFFFAOYSA-N 0.000 claims description 2
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- AQNSVANSEBPSMK-UHFFFAOYSA-N dicyclopentenyl methacrylate Chemical compound C12CC=CC2C2CC(OC(=O)C(=C)C)C1C2.C12C=CCC2C2CC(OC(=O)C(=C)C)C1C2 AQNSVANSEBPSMK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 claims description 2
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 3
- ZCYIYBNDJKVCBR-UHFFFAOYSA-N 2-prop-2-enoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCC=C ZCYIYBNDJKVCBR-UHFFFAOYSA-N 0.000 claims 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000002696 manganese Chemical class 0.000 claims 1
- 239000004800 polyvinyl chloride Substances 0.000 claims 1
- 229920000915 polyvinyl chloride Polymers 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 abstract description 14
- 238000006116 polymerization reaction Methods 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 238000005266 casting Methods 0.000 abstract 1
- 238000000465 moulding Methods 0.000 abstract 1
- 239000010408 film Substances 0.000 description 99
- 239000007787 solid Substances 0.000 description 92
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 239000008199 coating composition Substances 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
- 239000004816 latex Substances 0.000 description 50
- 229920000126 latex Polymers 0.000 description 50
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 49
- 229920005989 resin Polymers 0.000 description 47
- 239000011347 resin Substances 0.000 description 47
- 239000000463 material Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 39
- 238000012360 testing method Methods 0.000 description 39
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 33
- 239000003795 chemical substances by application Substances 0.000 description 30
- 239000011230 binding agent Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 24
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 23
- 238000002156 mixing Methods 0.000 description 22
- 229910000831 Steel Inorganic materials 0.000 description 20
- 239000010959 steel Substances 0.000 description 20
- 239000010936 titanium Substances 0.000 description 20
- 239000000049 pigment Substances 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 13
- 150000002917 oxazolidines Chemical class 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 150000002923 oximes Chemical class 0.000 description 12
- 239000003973 paint Substances 0.000 description 12
- 229920005862 polyol Polymers 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 150000003077 polyols Chemical class 0.000 description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 9
- 238000007605 air drying Methods 0.000 description 9
- 229920001971 elastomer Polymers 0.000 description 9
- 239000005060 rubber Substances 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 150000001414 amino alcohols Chemical class 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 7
- 230000002441 reversible effect Effects 0.000 description 7
- 239000002966 varnish Substances 0.000 description 7
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 239000003570 air Substances 0.000 description 6
- 238000006701 autoxidation reaction Methods 0.000 description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 239000004922 lacquer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
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- C—CHEMISTRY; METALLURGY
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- C08F299/0478—Copolymers from unsaturated polyesters and low molecular monomers characterised by the monomers used
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- 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
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- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
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- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
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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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C—CHEMISTRY; METALLURGY
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Ceramic Engineering (AREA)
- Structural Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/703,348 US4097677A (en) | 1976-07-07 | 1976-07-07 | Unsaturated esters of glycol monodicyclopentenyl ethers |
JP14284280A JPS5681529A (en) | 1976-07-07 | 1980-10-13 | Unsaturated ester of glycolmonodicyclopentenyl ether |
Publications (2)
Publication Number | Publication Date |
---|---|
SE7806632L SE7806632L (sv) | 1979-12-07 |
SE437151B true SE437151B (sv) | 1985-02-11 |
Family
ID=26474723
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7908730A SE429231B (sv) | 1976-07-07 | 1978-06-06 | Monomerer och anvendning av dessa |
SE7806632A SE437151B (sv) | 1976-07-07 | 1978-06-06 | Monomerkompositioner samt anvendning derav |
SE7908731A SE7908731L (sv) | 1976-07-07 | 1979-10-22 | Monomerkompositioner |
SE8102296A SE443566B (sv) | 1976-07-07 | 1981-04-09 | Polymer innehallande enheter av dicyklopentadienderivat av en eteniskt omettad syra for anvendning i beleggningskompositioner |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7908730A SE429231B (sv) | 1976-07-07 | 1978-06-06 | Monomerer och anvendning av dessa |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7908731A SE7908731L (sv) | 1976-07-07 | 1979-10-22 | Monomerkompositioner |
SE8102296A SE443566B (sv) | 1976-07-07 | 1981-04-09 | Polymer innehallande enheter av dicyklopentadienderivat av en eteniskt omettad syra for anvendning i beleggningskompositioner |
Country Status (9)
Country | Link |
---|---|
US (1) | US4097677A (de) |
JP (1) | JPS5681529A (de) |
AU (2) | AU523457B2 (de) |
BE (2) | BE869355A (de) |
DE (2) | DE2825627A1 (de) |
GB (2) | GB1600628A (de) |
NL (2) | NL185341C (de) |
SE (4) | SE429231B (de) |
ZA (1) | ZA7803231B (de) |
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US4234711A (en) * | 1978-08-09 | 1980-11-18 | Rohm And Haas Company | Anaerobic adhesive and/or sealing compositions comprising dicyclopentenyloxyethyl (meth)acrylates |
US4299761A (en) * | 1979-03-19 | 1981-11-10 | Rohm And Haas Company | Polymer concrete compositions, methods of application thereof, and polymerized products thereof |
US4284731A (en) * | 1980-03-03 | 1981-08-18 | Rohm And Haas | Polyurethane adhesive compositions containing dicyclopentenyloxyalkyl (meth) acrylate |
US4311624A (en) * | 1980-07-02 | 1982-01-19 | Rohm And Haas Company | Autoxidizable compositions |
US4400413A (en) * | 1980-08-29 | 1983-08-23 | Rohm And Haas Company | Acrylic polymer concrete compositions |
US4360540A (en) * | 1980-12-30 | 1982-11-23 | Rohm And Haas Company | Radiation curable compositions containing cyanoalkoxyalkyl and cyanothiaalkylalkyl acrylates |
US4333963A (en) * | 1980-12-30 | 1982-06-08 | Rohm And Haas Company | Radiation curable compositions containing β-cyanoethoxyalkyl acrylates |
DE3103252A1 (de) * | 1981-01-31 | 1982-08-26 | Bayer Ag, 5090 Leverkusen | Acryl- und methacrylsaeurederivate des 5.6-dihydrodicyclopentadiens, verfahren zu ihrer herstellung und verwendung als reaktivverduenner |
US4460625A (en) * | 1981-07-16 | 1984-07-17 | Rohm And Haas Company | Method of coating and impregnating concrete substrates, and products obtained thereby |
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US3650669A (en) * | 1969-01-28 | 1972-03-21 | Union Carbide Corp | Treatment of monomeric and polymeric systems with high intensity predominantly continuum light radiation |
US3681438A (en) * | 1970-10-26 | 1972-08-01 | Union Carbide Corp | Preparation of bicyclo (2.2.1) hept-2-en-ylmethyl acrylate |
US4001304A (en) * | 1974-05-02 | 1977-01-04 | Rohm And Haas Company | Acrylic acid esters |
JPS607665B2 (ja) * | 1976-01-01 | 1985-02-26 | 日石三菱株式会社 | 硬化性被覆組成物 |
AU2286677A (en) * | 1976-03-08 | 1978-09-07 | Rohm & Haas | Diluent for polyester resin and coating and impregnating compositions |
-
0
- ZA ZA00783231A patent/ZA7803231B/xx unknown
-
1976
- 1976-07-07 US US05/703,348 patent/US4097677A/en not_active Expired - Lifetime
-
1978
- 1978-05-26 GB GB23070/78A patent/GB1600628A/en not_active Expired
- 1978-05-26 GB GB23069/78A patent/GB1598780A/en not_active Expired
- 1978-06-06 SE SE7908730A patent/SE429231B/sv not_active IP Right Cessation
- 1978-06-06 SE SE7806632A patent/SE437151B/sv not_active IP Right Cessation
- 1978-06-07 AU AU36909/78A patent/AU523457B2/en not_active Expired
- 1978-06-07 AU AU36910/78A patent/AU522355B2/en not_active Expired
- 1978-06-12 DE DE19782825627 patent/DE2825627A1/de active Granted
- 1978-06-12 DE DE2825737A patent/DE2825737C2/de not_active Expired
- 1978-06-19 NL NLAANVRAGE7806577,A patent/NL185341C/xx not_active IP Right Cessation
- 1978-06-19 NL NLAANVRAGE7806576,A patent/NL185409C/xx not_active IP Right Cessation
- 1978-07-28 BE BE189570A patent/BE869355A/xx not_active IP Right Cessation
- 1978-07-28 BE BE189571A patent/BE869356Q/xx not_active IP Right Cessation
-
1979
- 1979-10-22 SE SE7908731A patent/SE7908731L/xx not_active Application Discontinuation
-
1980
- 1980-10-13 JP JP14284280A patent/JPS5681529A/ja active Granted
-
1981
- 1981-04-09 SE SE8102296A patent/SE443566B/sv unknown
Also Published As
Publication number | Publication date |
---|---|
AU523457B2 (en) | 1982-07-29 |
AU3690978A (en) | 1979-12-13 |
US4097677A (en) | 1978-06-27 |
SE7908731L (sv) | 1979-12-07 |
ZA7803231B (en) | |
JPS6143337B2 (de) | 1986-09-26 |
DE2825627A1 (de) | 1979-12-20 |
NL185409C (nl) | 1990-04-02 |
GB1600628A (en) | 1981-10-21 |
GB1598780A (en) | 1981-09-23 |
NL7806577A (nl) | 1979-12-21 |
SE429231B (sv) | 1983-08-22 |
AU522355B2 (en) | 1982-06-03 |
BE869355A (fr) | 1979-01-29 |
SE7806632L (sv) | 1979-12-07 |
SE7908730L (sv) | 1979-12-07 |
NL7806576A (nl) | 1979-12-21 |
BE869356Q (fr) | 1979-01-29 |
JPS5681529A (en) | 1981-07-03 |
DE2825737C2 (de) | 1986-12-04 |
AU3691078A (en) | 1979-12-13 |
SE8102296L (sv) | 1981-04-09 |
DE2825737A1 (de) | 1979-12-20 |
NL185341C (nl) | 1990-03-16 |
SE443566B (sv) | 1986-03-03 |
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