JPH0216112A - Thermosetting resin composition - Google Patents
Thermosetting resin compositionInfo
- Publication number
- JPH0216112A JPH0216112A JP16533988A JP16533988A JPH0216112A JP H0216112 A JPH0216112 A JP H0216112A JP 16533988 A JP16533988 A JP 16533988A JP 16533988 A JP16533988 A JP 16533988A JP H0216112 A JPH0216112 A JP H0216112A
- Authority
- JP
- Japan
- Prior art keywords
- unsaturated
- resin
- acid
- unsaturated polyester
- vinyl ester
- 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.)
- Pending
Links
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 9
- 239000011342 resin composition Substances 0.000 title claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 32
- 229920005989 resin Polymers 0.000 claims abstract description 25
- 239000011347 resin Substances 0.000 claims abstract description 25
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 229920006337 unsaturated polyester resin Polymers 0.000 claims abstract description 15
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 acrylic ester Chemical class 0.000 claims description 10
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 229920006305 unsaturated polyester Polymers 0.000 abstract description 6
- 238000005260 corrosion Methods 0.000 abstract description 5
- 230000007797 corrosion Effects 0.000 abstract description 5
- 239000000945 filler Substances 0.000 abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 4
- 239000003086 colorant Substances 0.000 abstract description 4
- 239000003085 diluting agent Substances 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 4
- 239000013008 thixotropic agent Substances 0.000 abstract description 3
- 239000002685 polymerization catalyst Substances 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 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
- 239000004593 Epoxy Substances 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 125000005395 methacrylic acid group Chemical group 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 150000007519 polyprotic acids Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 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 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VZWGRQBCURJOMT-UHFFFAOYSA-N Dodecyl acetate Chemical compound CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 1
- GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-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
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GCNKJQRMNYNDBI-UHFFFAOYSA-N [2-(hydroxymethyl)-2-(2-methylprop-2-enoyloxymethyl)butyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CC)COC(=O)C(C)=C GCNKJQRMNYNDBI-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 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 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は耐咬性、耐水性、Ｉｆ）ｌ腐食性、耐汚染性に
富む熱硬化性樹脂組成物に関し、特にゲルコート用組成
物として有用な熱硬化性樹脂組成物に関するものである
。Detailed Description of the Invention (Industrial Field of Application) The present invention relates to a thermosetting resin composition that is highly resistant to chewing, water, corrosion, and staining, and is particularly useful as a gel coat composition. The present invention relates to a thermosetting resin composition.
（従来の技術）
ゲルコートは一般にＦＲＰの最外層であるため、空気、
光、水、海水、ガス、溶剤等の環境に常に接触しており
、従ってこれに使われる樹脂及びその配合物には機械的
な性能はもちろんのこと、耐候性、耐腐食性、＃汚染性
などにすぐれたものか要望されている。(Prior art) Gel coat is generally the outermost layer of FRP, so it is free from air,
It is constantly in contact with the environment such as light, water, seawater, gas, and solvents, so the resins and their compounds used in these products have not only mechanical performance but also weather resistance, corrosion resistance, and stain resistance. There is a demand for something that is excellent.
このために使用される樹脂も特に選択され、用途によっ
ては不飽和ビニルエステル樹脂（エポキシアクリレート
）、ビスフェノール系ポリエステル樹脂、イソフタル酸
系ポリエステル樹脂などが使われている。The resin used for this purpose is also particularly selected, and depending on the purpose, unsaturated vinyl ester resin (epoxy acrylate), bisphenol polyester resin, isophthalic acid polyester resin, etc. are used.
しかしながら、ゲルコートに対する′Ｊ３望は年々きび
しくなり、これらの樹脂ではト記特性は充分満足すべき
ものてはないのて、特にすぐれた性質の製品か要望され
てきた。However, the expectations for gel coats have become more severe year by year, and since these resins do not fully satisfy the above properties, products with particularly excellent properties have been desired.
この要望に応えるものとして、フッ素を分子内に導入す
ると効果的であることか見出され、フ・ν素化されたア
ルキル基及び／またはアルキレン基を有するアルコール
のアクリル酸エステル及び／またはメタアクリル酸エス
テルを含む熱硬化性樹脂組成物か開発された。（特願昭
５７−６８７７１号）（発明か解決しようとする課題）
しかし、］二記のフッ素化されたアルキレン、（及び／
またはアルキレンツ＾を有するアルコールのアクリル酸
エステル及び／またはメタアクリル酸エステルは、不飽
和ポリエステル樹脂及び／または不飽和ビニルエステル
樹脂との相溶性かよくないため、配合量を低くせざるを
得す、硬化物の耐候性、耐腐食性、耐汚染性などのＷＪ
′Ａな改Ｒのためには、必ずしも十分に満足てきるもの
とはｄい難い。In order to meet this demand, it has been found that it is effective to introduce fluorine into the molecule, and acrylic esters and/or methacrylic esters of alcohols having fluorinated alkyl groups and/or alkylene groups have been found to be effective. Thermosetting resin compositions containing acid esters have been developed. (Japanese Patent Application No. 57-68771) (Problem to be solved by the invention) However, the two fluorinated alkylenes (and/
Alternatively, acrylic esters and/or methacrylic esters of alcohols having alkylene ^ are not compatible with unsaturated polyester resins and/or unsaturated vinyl ester resins, so the blending amount must be lowered. WJ of weather resistance, corrosion resistance, stain resistance, etc. of cured products
'It is difficult to be completely satisfied with A reform.
また、■−記アクリル酸エステル及びメタアクリル酸エ
ステルは硬化時に嫌気性を示すのて、空気と接した面を
完全に硬化させるため、表面をパラフィンて被覆し、空
気を遮断した状ｙ島での硬化か必要である。In addition, since the acrylic esters and methacrylic esters described in ■- are anaerobic during curing, in order to completely cure the surface in contact with the air, the surface is coated with paraffin and the air is blocked. curing is required.
木５１明者らは、−Ｌ述した実情に鑑みて鋭意検討を重
ねた結果、不飽和ポリエステル樹脂及び／または不飽和
ビニルエステル樹脂を主成分とする熱硬化性樹脂におい
て、該樹脂中のビニルモノマーかフッ素化されたアルキ
ル基及び／またはアルキレン基を、ウレタン基の両方を
分子中に有するアクリル酸エステル及び／またはメタア
クリル酸エステルを含むことを特徴とする熱硬化性樹脂
組成物か＋１候性、＃腐食性、耐汚染性などに秀れてい
る・１１か′Ｉ明し、本発明を完成するに至った。As a result of extensive studies in view of the actual situation mentioned above, the authors found that, in thermosetting resins whose main components are unsaturated polyester resins and/or unsaturated vinyl ester resins, vinyl in the resin A thermosetting resin composition characterized by containing an acrylic ester and/or a methacrylic ester having both a fluorinated alkyl group and/or alkylene group and a urethane group in the molecule as a monomer. The present invention has been completed based on the results of the present invention.
即ち末完ＩＪ＋は、
（＋）不飽和ポリエステル樹脂または不飽和ビニルエス
テル樹脂
（２）ビニルモノマ−
（３）フッ素化されたアルキル基及び／またはアルキレ
ン基とウレタン基の両方を有するアクリル酸エステル及
び／またはメタアクリル酸エステル
（４）１合触媒
からなる熱硬化性樹脂組成物に関する。That is, the terminal IJ+ is (+) an unsaturated polyester resin or an unsaturated vinyl ester resin (2) a vinyl monomer (3) an acrylic ester having both a fluorinated alkyl group and/or an alkylene group and a urethane group; Alternatively, the present invention relates to a thermosetting resin composition comprising a methacrylic acid ester (4) and a combined catalyst.
〔作用）
本発明に使用するフッ素化されたアルキル基及び／また
はアルキレン基とウレタン基の両方を有するアクリル酸
エステル及び／またはメタアクリル酸エステルは、不飽
和ポリエステル樹脂またはビニルエステル樹脂と任意の
割合て混合することかてき、また共重合性か非常に良好
て、［［つ嫌気性か少ないという大きな特徴を有するた
め、ゲルコート用樹脂としては特に有用である。[Function] The acrylic ester and/or methacrylic ester having both a fluorinated alkyl group and/or alkylene group and a urethane group used in the present invention can be mixed with the unsaturated polyester resin or vinyl ester resin in any proportion. It is particularly useful as a gel coat resin because it can be mixed easily, has very good copolymerizability, and has little anaerobic properties.
以ド１本発明の構成について詳しく説明する。Below, the configuration of the present invention will be explained in detail.
本発明による組成物の特徴は、不飽和ポリエステル樹脂
、不飽和ビニルエステル樹脂の成分のうちのビニルモノ
マー（一般にはスチレンモノマー）の０．１〜５０屯埴
％、好ましくは０．５〜４０爪礒％をフッ素化されたア
ルキル基及び／またはアルキレン）Ｋとウレタン基の両
方を有するアクリル酸エステルまたはメタアクリル酸エ
ステルを使用するものである。フッ素化されたアルキル
基及び／またはアルキレン基とウレタン基の両方を有す
るアクリル酸エステルまたはメタアクリル酸エステルの
使用にか０．１１礒％未満ては耐候性、耐水性、耐腐食
性、耐汚染性か不十分てあり、一方、使用１遥か５０虫
礒％を超えるときには、抗張力、硬度１曲げ強さなどの
機械的性質か低下する。The composition according to the invention is characterized in that 0.1 to 50% of the vinyl monomer (generally styrene monomer) among the components of the unsaturated polyester resin and unsaturated vinyl ester resin, preferably 0.5 to 40% of the vinyl monomer (generally styrene monomer) An acrylic ester or a methacrylic ester having both a fluorinated alkyl group and/or alkylene group and a urethane group is used. The use of acrylic esters or methacrylic esters having both fluorinated alkyl and/or alkylene groups and urethane groups provides weather resistance, water resistance, corrosion resistance, and stain resistance of less than 0.11%. On the other hand, when it is used in excess of 50%, mechanical properties such as tensile strength, hardness, and bending strength are decreased.
かくして得られた樹脂に通常のゲルコート用樹脂の配合
に従って揺変則、着色剤、場合によっては充填剤、硬化
促進剤、右釈剤を加えてゲルコート用組成物を製造する
。A gel coat composition is prepared by adding a thixotropy, a coloring agent, and in some cases a filler, a curing accelerator, and a diluting agent to the thus obtained resin in accordance with the usual blending of gel coat resins.
本発明において使用される不飽和ポリエステル樹脂は、
不飽和ポリエステルをビニルモノマーに溶解して得られ
るものである。不飽和ポリエステルは慣用のものてもよ
く、不飽和多塩基酸及び／またはその無水物、飽和多塩
基醜またはその無水物、クリコール、多価アルコールを
混合して脱水縮合させた分子埴約５００〜５０００のオ
リゴマーであり、その原料を例示すると次のよってある
。The unsaturated polyester resin used in the present invention is
It is obtained by dissolving unsaturated polyester in vinyl monomer. The unsaturated polyester may be a conventional unsaturated polyester, and may be a polyester having a molecular weight of about 500 or more, which is obtained by dehydrating and condensing a mixture of an unsaturated polybasic acid and/or its anhydride, a saturated polybasic acid or its anhydride, glycol, and a polyhydric alcohol. 5000 oligomer, and examples of its raw materials are as follows.
不飽和多１′！！基酸またはその無水物二無水マレイン
酸、マレイン酸、フマル触、イタコン酸、力−ヒック酸
、無水カービ・ンク酸等
飽和多Ｉｔ！基酸またはその無水物：無水フタル酸、フ
タル酸、イソフタル酸、テレフタル酸、デトラヒトロフ
タル酸、コハク酸、アジピン酸、アゼライン酸、セハチ
ン酸、ヘット酸、無水ヘット酸象
多価アルコール：
（１）クリコール エチレンクリコール、ジエチレンク
リコール、プロピレンクリコール１ ジプロピレンクリ
コール、トリエチレンクリコール、ブタンジオール、ネ
オペンチルクリコール、本末化ビスフェノールＡ、ヒス
フェノールＡエチレンオキサイド付加Ｔｈ等。Unsaturated 1'! ! Base acids or anhydrides such as maleic dianhydride, maleic acid, fumaric acid, itaconic acid, hic acid, carboxylic anhydride, etc. Base acids or their anhydrides: phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, detrahydrophthalic acid, succinic acid, adipic acid, azelaic acid, cehatic acid, het acid, het acid anhydride Polyhydric alcohol: ( 1) Glycol Ethylene glycol, diethylene glycol, propylene glycol 1, dipropylene glycol, triethylene glycol, butanediol, neopentyl glycol, powdered bisphenol A, hisphenol A with ethylene oxide added Th, etc.
（２）３価以りのアルコール−ペンタエリスリ・ント、
グリセリン、トリメチロールプロパン等。(2) Trihydric or higher alcohol - pentaerythrin,
Glycerin, trimethylolpropane, etc.
また、本発明において使用される不飽和ビニルエステル
樹脂は、不飽和ビニルエステルをビニルモノマーに溶解
して得られるものである。不飽和ビニルエステルは、多
価エポキシ化合物に不飽和酸をエボキシノ６（／カルボ
キシル基の比かほぼ当１直て反応して製必するもので１
次に例示するような原料か使用される。Moreover, the unsaturated vinyl ester resin used in the present invention is obtained by dissolving an unsaturated vinyl ester in a vinyl monomer. Unsaturated vinyl esters are produced by reacting a polyvalent epoxy compound with an unsaturated acid, with the ratio of eboxyno 6 (/carboxyl group) approximately equal to 1.
Raw materials such as those exemplified below are used.
多価エポキシ化合物：ビスフェノールＡとエピクロルヒ
ドリン縮合物、フタル酸とエピクロルヒドリンの縮合物
、ツタジエンオリゴマーの酸化物、インプレンオリゴマ
ーの酸化物、ユノックス２０１（商品名、ユニオンカー
バイト社製、３．４−エポキシ−６−メチルシクロヘキ
ジルメチルー３．１−エポキシ−６メチルシクロヘキサ
ンカルボキシレー１−）、ユノックス２８９（商品名、
ユニオンカーハイトンＦ製、エポキシシクロヘキシルア
シベート）、ノボラックエポキシ等
不飽和酸：メタアクリル酸、アクリル酸、クロトン酸、
イタコン酸、等
」−記の不飽和ポリエステル、不飽和ビニルエステルに
配合されるビニルモノマーを例示すると次のよってある
゛
スチレン、メタアクリル酸メチル、メタアクリル酸エチ
ル、アクリル酸メチル、アクリル酸２エチルヘキシル、
エチレンクリコールジアクリレート、ポリエチレングリ
コールジアクリレート、エチレンクリコールジメタクリ
レート、ポリエチレンクリコールジメタクリレート、プ
ロピレンクリコールジアクリレート、ポリプロピレンク
リコールジアクリレート、プロピレングリコールジメタ
クリレート、ポリプロピレンクリコールジメタクリレー
ト、トリメチロールプロパンジアクリレート、トリメチ
ロールプロパントリアクリレートトリメチロールプロパ
ンシメタクリレート、トリメチロールプロパントリメタ
クリレート、ペンタエリスリットトリアクツレート、ペ
ンタエリスリットテトラアクリレート、ペンタエリスリ
ット１−リメタクリレート、ペンタエリスリットテトラ
メタクリレート等。Polyvalent epoxy compounds: bisphenol A and epichlorohydrin condensate, phthalic acid and epichlorohydrin condensate, tutadiene oligomer oxide, imprene oligomer oxide, UNOX 201 (trade name, manufactured by Union Carbide Co., Ltd., 3.4- Epoxy-6-methylcyclohexylmethyl-3,1-epoxy-6methylcyclohexanecarboxylene 1-), Yunox 289 (trade name,
Union Kerhighton F, epoxycyclohexyl acylate), novolak epoxy, etc. Unsaturated acids: methacrylic acid, acrylic acid, crotonic acid,
Examples of vinyl monomers that can be added to the unsaturated polyesters and unsaturated vinyl esters described in "Itaconic acid, etc." are as follows: styrene, methyl methacrylate, ethyl methacrylate, methyl acrylate, 2-ethylhexyl acrylate. ,
Ethylene glycol diacrylate, polyethylene glycol diacrylate, ethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, propylene glycol diacrylate, polypropylene glycol diacrylate, propylene glycol dimethacrylate, polypropylene glycol dimethacrylate, trimethylol propane diacrylate acrylate, trimethylolpropane triacrylate, trimethylolpropane dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacturate, pentaerythrittetraacrylate, pentaerythritol 1-remethacrylate, pentaerythritol tetramethacrylate, etc.
これらのビニルモノマーの配合には不飽和ポリエステル
樹脂、または不飽和ビニルエステル樹脂の全重量の２０
〜７０％である。The blending of these vinyl monomers includes unsaturated polyester resin or 20% of the total weight of the unsaturated vinyl ester resin.
~70%.
未発明に使用されるフッ素化されたアルキル基及び／ま
たはアルキレン基と、ウレタン基の両方を分子中に有す
るアクリル酸エステル及び／またはメタアクリル酸エス
テルは水素の一部または全部かツウ素によって置換され
、かつ炭素数の合計か １〜３（］であるアルキル基及
び／またはアルキレン基とウレタン基を共に有するアル
コールのアクリル酸エステルまたはメタアクリル酸エス
テルてあって、次に例示されるような化合物である（
イ！ｌ し 、 ｍ＝ ０〜 ＋８ 、
ｎ＝ ０〜１８ 、 ｐ＝ ｌ 〜 ｂＲ
＝１１またはＣＩｌ Ｇｏ、×＝１１またはＣＩｌ 、
Ｒ＝ｌ＋またはＣ１ｌ （Ｃ１＋ ）である）。Acrylic esters and/or methacrylic esters that have both a fluorinated alkyl group and/or alkylene group and a urethane group in the molecule used in the uninvention are partially or completely substituted with hydrogen. and an acrylic ester or methacrylic ester of an alcohol having both an alkyl group and/or an alkylene group and a urethane group with a total carbon number of 1 to 3 (], as exemplified below) It is (
stomach! l, m=0~+8,
n=0~18, p=l~bR
= 11 or CIl Go, × = 11 or CIl,
R=l+ or C1l (C1+)).
これらの化合物は、たとえば、インシアナトアルキルア
クリレートまたはインシアナトアルキルメタクリレート
とフッ素化されたアルコールとをシフチルスズジラウレ
ートなどを触媒として反応させることにより容易に合成
することかてきる。These compounds can be easily synthesized, for example, by reacting incyanatoalkyl acrylate or incyanatoalkyl methacrylate with a fluorinated alcohol using cyphthyltin dilaurate or the like as a catalyst.
フッ素化されたアルキル、！、（及び／またはアルキレ
ン基とウレタン基の両方を分子中に右するアルコールの
アクリル酸エステルまたはメタアクリル酸エステルの配
合量は、不飽和ポリエステルまたは不飽和ビニルエステ
ルに配合するビニルモノマーの（）、１〜５０重量％、
好ましくは０．５〜４０屯ｖ％であることか望ましい。Fluorinated alkyl,! , (and/or the amount of the acrylic ester or methacrylic ester of an alcohol containing both an alkylene group and a urethane group in the molecule is determined by the amount of the vinyl monomer blended into the unsaturated polyester or unsaturated vinyl ester), 1 to 50% by weight,
Preferably, it is 0.5 to 40 ton v%.
これらの原料を用いて不飽和ポリエステル樹脂または不
飽和ビニルエステル樹脂を製造するには、常法によって
行う。即ち、不飽和ポリエステル樹脂は、不飽和多塩基
酸ｌＯ〜５０モル％、飽和多ｌ！！基酸０〜４０モル％
、多価アルコール４１１〜６０モル％を混合し、撹拌し
ながら窒素気流中て １８０〜２３０℃において １〜
１２時間加熱する。生成した水を分離し、酸価、木酸価
、粘度か所定の値に達したときに反応を止め、冷却し、
禁１Ｅ剤（たとえばハイドロキノン０．０１〜０．１．
’１１７ｄ％／全量）を加え、ビニルモノマー（２０〜
７ｆｌｉｉ％／全量）を混合することによって作ること
かてきる。In order to produce an unsaturated polyester resin or an unsaturated vinyl ester resin using these raw materials, a conventional method is used. That is, the unsaturated polyester resin contains an unsaturated polybasic acid lO~50 mol% and a saturated polybasic acid lO~50 mol%. ! Base acid 0-40 mol%
, 411 to 60 mol% of polyhydric alcohol was mixed, and the temperature was 1 to 180°C at 180 to 230°C in a nitrogen stream while stirring.
Heat for 12 hours. Separate the produced water, stop the reaction when the acid value, wood acid value, and viscosity reach the predetermined values, cool it,
1E drugs (e.g. hydroquinone 0.01-0.1.
'117d%/total amount) was added, and vinyl monomer (20~
7flii%/total amount).
不飽和ビニルエステル樹脂は、多価エポキシ化合物ｌち
ｊｌｉに対し、不飽和酸ｌ当ｈ１、ハイドロキノン０．
０１〜０．１ ｉｌｊψ％／全に、触媒としてアミンな
ど０．１〜１虫星％／全場を加え、ビニルモノマ−（２
０〜７０屯７ｄ％／全に）の存在下、空気の雰囲気て撹
拌しながら徐々に昇温し、 １１０〜Ｉ：ｌＯ’Ｃに
１〜５時間保って、酸価、エポキシ価、粘度か所定の値
に達したとき冷却することによって造ることかてきる。The unsaturated vinyl ester resin contains 1 h of unsaturated acid and 0.0 of hydroquinone per 1 of the polyvalent epoxy compound.
01 to 0.1 iljψ%/total, add 0.1 to 1 insect star%/total, such as amine as a catalyst, and add vinyl monomer (2
In the presence of 0 to 70 tons (7 d%/total), the temperature was gradually raised with stirring in an air atmosphere to 110 to 1:1O'C.
It can be made by keeping it for 1 to 5 hours and cooling it when the acid value, epoxy value, and viscosity reach predetermined values.
必要に応しさらにビニルモノマーを添加してもよい。A vinyl monomer may be further added if necessary.
このようにして製造した不飽和ポリエステル樹脂または
不飽和ビニルエステル樹脂に揺変剤、着色剤、場合によ
っては充、填剤、硬化促進剤、希釈剤を常法により配合
してゲルコート用組成物をつくる。A gel coat composition is prepared by adding a thixotropic agent, a coloring agent, and in some cases a filler, a curing accelerator, and a diluent to the unsaturated polyester resin or unsaturated vinyl ester resin thus produced. to make.
揺変剤としては、シソ力微粉末、高分子縫のウレタン樹
脂、アクリル樹脂、ポリエステル樹脂などが使われる。As the thixotropic agent, fine powder, polymer-stitched urethane resin, acrylic resin, polyester resin, etc. are used.
青色剤としては、白色または色顔料か使われたとえばチ
タン白、酸化鉄、酸化クロムなどがある。As the blue agent, white or colored pigments are used, such as titanium white, iron oxide, chromium oxide, etc.
充填剤としては、炭酸カルシウム、シリカ粉末、クレー
、ガラス粉末、ガラスフレーク、マイカフレークなどが
ある。Examples of fillers include calcium carbonate, silica powder, clay, glass powder, glass flakes, and mica flakes.
硬化促進剤には、ナフデン酸コバルト、オクトエ酸コバ
ルトなどが使われる。Cobalt naphdate, cobalt octoate, etc. are used as hardening accelerators.
希釈剤としては、少埴の溶剤、たとえばキジロール、フ
チルカービトール、ラウリルアセテート、ジメチルフタ
レートなどが使われる。その他消泡剤、レベリング剤な
ども適宜添加される。As the diluent, suitable solvents such as quidylol, phthyl carbitol, lauryl acetate, dimethyl phthalate, etc. are used. Other antifoaming agents, leveling agents, etc. may also be added as appropriate.
ゲルコート用組成物の混合には、ホモミキサー、ルータ
−、ニーダ−か使われる。A homo mixer, router, or kneader is used to mix the gel coat composition.
本発明の組成物を用いてゲルコートを行うには１組成物
に重合触媒（過酸化ベンソイル、過酸化ラウリル、メチ
ルエチルケトンペルオキシド。To perform gel coating using the composition of the present invention, one composition includes a polymerization catalyst (benzoyl peroxide, lauryl peroxide, methyl ethyl ketone peroxide).
キュメンヒドロペルオキシドなど）を、ＭＩａＳに対し
０．１〜２屯量部を加え型に塗布する。塗布方法は刷毛
塗、ローラーコート、スプレーなとである。塗１＋ｊ
Ｌ／たのちは通常のＦＲＰ成形注形法たかりて、不飽和
ポリエステル樹脂及び／または不飽和ヒニルエスデル樹
脂と繊維とを植層する。cumene hydroperoxide, etc.) in an amount of 0.1 to 2 parts by volume based on MIaS is applied to the mold. Application methods include brushing, roller coating, and spraying. Paint 1+j
L/Tanochi uses a normal FRP molding and casting method to layer unsaturated polyester resin and/or unsaturated hinyl Esder resin and fibers.
以ド、実施例に）＆き本発明をさらに具体的に説明する
。The present invention will now be described in more detail with reference to Examples.
実施例１
５５モルのプロピレンクリコールと２０モルのイソフタ
ル酸とを混合し、撹拌しなから窒素雰囲気中て １８０
〜１９０℃において約２時間反応し、酸価か８０になっ
たとき反応物の温度を１５０°Ｃに下げ、次いて３０モ
ルの無水マレイン酸を加え２１０〜２２０°Ｃて約６時
間加熱し、酸価か３０に達したとき反応を中Ｉトする。Example 1 55 moles of propylene glycol and 20 moles of isophthalic acid were mixed and mixed in a nitrogen atmosphere at 180 mols.
The reaction was carried out at ~190°C for about 2 hours, and when the acid value reached 80, the temperature of the reactant was lowered to 150°C, and then 30 mol of maleic anhydride was added and heated at 210-220°C for about 6 hours. When the acid number reaches 30, the reaction is stopped.
次に１反応物を冷却して Ｉ［ｉ０’Ｃになったときパ
イトロキノン０．０３重量％を加え、さらに１３０℃に
なったときスチレン３２玉績％。Next, 1 reactant was cooled, and when the temperature reached I[i0'C, 0.03% by weight of pytroquinone was added, and when the temperature reached 130°C, 32% by weight of styrene was added.
および式（Ｉ）て示されるモノマー５１７ｉｉ−％を添
加して均一に混合し冷却する。この不飽和ボリエステル
樹脂１０ ｔ１１重部に対しＪ、ｆ変則として工ロンー
ル（商品名、デクサ社製、酸化ｆ１素粉末）２玉礒部１
着色剤としてチタン白 ３屯賃部、鉄鎖系ピンク顔料Ｑ
、 ５ Ｉｊ ＋逢部、充填剤として石英粉末５屯清
部、硬化促進剤としてナフテン酸コバルトｏ、ｓＢ著部
を加え、ホモミキサーてよ・〈混合してケルコート用組
成物を造った。and 517ii-% of the monomer represented by formula (I) are added, mixed uniformly, and cooled. This unsaturated polyester resin has 10 t11 parts, J and f irregularities, such as Koronol (trade name, Dexa Co., Ltd., oxidized f1 elementary powder), 2 parts 1 part
Titanium white 3 tons as a coloring agent, iron chain pink pigment Q
, 5 Ij+Aibe, 5 tons of quartz powder as a filler, and 5 tons of cobalt naphthenate and sB as hardening accelerators were added and mixed in a homomixer to prepare a composition for Kelcoat.
この組成物１００屯着部に過酸化ベンゾイルのジメチル
フタレート中の５０％ペースト ｌ、１（ｊｉ１部を加
え、浄化槽の型にゲルコートを施し、 ＦＲＰの部分は
オルソフタル酸を用いた通常のポリエステル樹脂て慣用
のハントレイアップ法により製造した。Add 1 part of 50% benzoyl peroxide paste in dimethyl phthalate to 100 parts of this composition, gel coat the septic tank mold, and coat the FRP part with ordinary polyester resin using orthophthalic acid. Manufactured by the conventional Hunt lay-up method.
ゲルコートと １１（Ｐ層の密着性はよく、この浄化槽
を屋外に１年間暴露したか全く表面光沢の変化かなかっ
た。これに対しフッ素化アルキルウレタンメタクリレー
トを省略して製造したゲルコートを施した場合には、１
年間の屋外暴露て光沢はなくなり ＦＲＰ層部分のガラ
ス目か浮き出した。The adhesion between the gel coat and the 11 (P layer) was good, and there was no change in surface gloss even after exposing this septic tank outdoors for one year.On the other hand, when a gel coat manufactured by omitting the fluorinated alkyl urethane methacrylate was applied. For, 1
After years of outdoor exposure, the luster has disappeared and the glass grains in the FRP layer have become visible.
また、本発明による組成物を施した浄化槽は表面の汚れ
かほとんどなく、水洗によって外観がもと通り美しくな
ったか、フッ素化アルキルメタクリレ−１〜を省略して
製造した浄化槽は表面のｌりれか大きく、水洗によって
も外観か美しくならなかった。In addition, the septic tanks treated with the composition of the present invention had almost no dirt on the surface, and the appearance returned to its original beauty after washing with water, or the septic tanks manufactured by omitting the fluorinated alkyl methacrylates had less dirt on the surface. It was so large that even washing it with water did not improve its appearance.
実施例２〜１２．および比較例１〜３
フツ素化アルキルウレタン（メタ）アクリレートの種類
と添加埴を変えた以外は実施例１と同様の試験を行なっ
た。Examples 2-12. and Comparative Examples 1 to 3 The same tests as in Example 1 were conducted except that the type of fluorinated alkyl urethane (meth)acrylate and the additive were changed.
配合例および試験結果を表１に示す。Table 1 shows formulation examples and test results.
（以Ｆ余白） フッ素化ウレタンアクリレートの種類 ４￥許出願人 昭和ロープイア化学株式会社 代 理 人(below F margin) Types of fluorinated urethane acrylate 4￥ permit applicant Showa Ropeia Chemical Co., Ltd. teenager Reason Man
Claims (1)
テル樹脂を主成分とする熱硬化性樹脂組成物において、
該樹脂中のビニルモノマーがフッ素化されたアルキル基
及び／またはアルキレン基を、ウレタン基の両方を分子
中に有するアクリル酸エステル及び／またはメタアクリ
ル酸エステルを含むことを特徴とする熱硬化性樹脂組成
物。In a thermosetting resin composition containing an unsaturated polyester resin and/or an unsaturated vinyl ester resin as a main component,
A thermosetting resin characterized in that the vinyl monomer in the resin contains an acrylic ester and/or a methacrylic ester having both a fluorinated alkyl group and/or alkylene group and a urethane group in the molecule. Composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16533988A JPH0216112A (en) | 1988-07-02 | 1988-07-02 | Thermosetting resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16533988A JPH0216112A (en) | 1988-07-02 | 1988-07-02 | Thermosetting resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0216112A true JPH0216112A (en) | 1990-01-19 |
Family
ID=15810460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16533988A Pending JPH0216112A (en) | 1988-07-02 | 1988-07-02 | Thermosetting resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0216112A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7754838B2 (en) * | 2006-08-08 | 2010-07-13 | E.I. Du Pont De Nemours And Company | Poly(meth)acrylamides and poly(meth)acrylates containing fluorinated amide |
-
1988
- 1988-07-02 JP JP16533988A patent/JPH0216112A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7754838B2 (en) * | 2006-08-08 | 2010-07-13 | E.I. Du Pont De Nemours And Company | Poly(meth)acrylamides and poly(meth)acrylates containing fluorinated amide |
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