CN107835736A - 衬里用组合物 - Google Patents
衬里用组合物 Download PDFInfo
- Publication number
- CN107835736A CN107835736A CN201680041133.0A CN201680041133A CN107835736A CN 107835736 A CN107835736 A CN 107835736A CN 201680041133 A CN201680041133 A CN 201680041133A CN 107835736 A CN107835736 A CN 107835736A
- Authority
- CN
- China
- Prior art keywords
- ester
- allyl ester
- lining
- diallyl
- multifunctional
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 150000002148 esters Chemical group 0.000 claims abstract description 42
- 229920005989 resin Polymers 0.000 claims abstract description 35
- 239000011347 resin Substances 0.000 claims abstract description 35
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 29
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 26
- -1 allyl ester Chemical class 0.000 claims description 119
- 239000000463 material Substances 0.000 claims description 45
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 15
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 13
- 125000002723 alicyclic group Chemical group 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- ZPOLOEWJWXZUSP-AATRIKPKSA-N bis(prop-2-enyl) (e)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C\C(=O)OCC=C ZPOLOEWJWXZUSP-AATRIKPKSA-N 0.000 claims description 7
- HABAXTXIECRCKH-UHFFFAOYSA-N bis(prop-2-enyl) butanedioate Chemical group C=CCOC(=O)CCC(=O)OCC=C HABAXTXIECRCKH-UHFFFAOYSA-N 0.000 claims description 7
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 claims description 7
- VVYDVQWJZWRVPE-UHFFFAOYSA-L dimethyltin(2+);diiodide Chemical compound C[Sn](C)(I)I VVYDVQWJZWRVPE-UHFFFAOYSA-L 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 239000003431 cross linking reagent Substances 0.000 abstract description 13
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 abstract description 3
- 239000002585 base Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000003822 epoxy resin Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 229920000647 polyepoxide Polymers 0.000 description 19
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 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 14
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000008595 infiltration Effects 0.000 description 5
- 238000001764 infiltration Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012719 thermal polymerization Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 241001614291 Anoplistes Species 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000746 allylic group Chemical group 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001880 copper compounds Chemical class 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 3
- 125000002347 octyl 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])[H] 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 3
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 3
- 229920006337 unsaturated polyester resin Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- LAWHHRXCBUNWFI-UHFFFAOYSA-N 2-pentylpropanedioic acid Chemical compound CCCCCC(C(O)=O)C(O)=O LAWHHRXCBUNWFI-UHFFFAOYSA-N 0.000 description 2
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-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
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- BKXRKRANFLFTFU-UHFFFAOYSA-N bis(prop-2-enyl) oxalate Chemical compound C=CCOC(=O)C(=O)OCC=C BKXRKRANFLFTFU-UHFFFAOYSA-N 0.000 description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
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- 235000002639 sodium chloride Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 150000000094 1,4-dioxanes Chemical class 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical class CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
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Abstract
课题在于，提供一种衬里用组合物，其可以解决海洋污染等环境问题、VOC的问题之类的问题，具有良好的固化速度。发现：通过将乙烯基酯树脂作为预聚物成分、并含有脂肪族或脂环式的多官能烯丙基酯化合物作为交联剂的组合物，可以解决课题。
Description
技术领域
本发明涉及衬里用组合物。衬里例如用于下水道处理设施的管状成型体内面、方形管内面等的复原用。
背景技术
最近的建筑结构物基本以混凝土、钢材为结构材料。然而，这些混凝土、钢材存在经年发生劣化的问题。近年来，为了防止建筑、隧道、桥墩、排水沟、上下水道管、燃气管道等使用混凝土、钢材的结构物的劣化、更正劣化进行了的结构物，实施了衬里。
如果对衬里方法进行具体说明，则将燃气管道、水道管、下水道管等管进行衬里的情况下，通过将含有热固性树脂的衬里材料进行管内插入后，利用热水使衬里材料固化等方法，可以将既定管内进行衬里(参照专利文献1)。
作为衬里中使用的树脂，可以举出环氧树脂、聚氨酯树脂、不饱和聚酯树脂、乙烯基酯树脂等，其中，从固化性、经济性的方面出发，主要使用有不饱和聚酯树脂、乙烯基酯树脂。这些树脂是含有预聚物成分和交联剂的组合物，通过自由基聚合反应使其固化。
公知的不饱和聚酯树脂组合物、乙烯基酯树脂组合物之类的树脂组合物中，作为交联剂，一般使用有苯乙烯(参照专利文献2)。然而，由于存在海洋污染等环境问题和挥发性有机化合物(VOC)的问题，因此期望开发除苯乙烯以外的交联剂。
作为除苯乙烯以外的交联剂，可以使用邻苯二甲酸二烯丙酯单体，但为了充分使其固化，需要较长的时间，要求进一步的研究。
现有技术文献
专利文献
专利文献1：日本特开2003-165158号公报
专利文献2：日本专利第2981330号公报
发明内容
发明要解决的问题
本发明的课题在于，提供：可以解决海洋污染等环境问题、VOC之类的问题、具有良好的固化速度的衬里用的树脂组合物。
用于解决问题的方案
本发明人等发现：通过含有乙烯基酯树脂作为预聚物成分、含有选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯作为交联剂的衬里用组合物，可以解决上述课题。
即，本发明可以如以下记载。
项1.一种衬里用组合物，其特征在于，含有：
乙烯基酯树脂；和，
选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯。
项2.根据项1所述的衬里用组合物，其特征在于，选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯为通式(1)所示的多官能烯丙基酯。
[式中，n表示2～4中的任意整数，z为n价的脂肪族烃基、n价的脂环式烃基或键合部(其中，仅n是2的情况)。]
项3.根据项1或2所述的衬里用组合物，其特征在于，选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯为琥珀酸二烯丙酯、富马酸二烯丙酯、马来酸二烯丙酯、衣康酸二烯丙酯、己二酸二烯丙酯、环己烷二羧酸二烯丙酯中的任意者。
项4.根据项1～3中任一项所述的衬里用组合物，其特征在于，相对于乙烯基酯树脂100重量份，含有20重量份以上且80重量份以下的选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯。
项5.一种衬里材料，其特征在于，其是使项1～4中任一项所述的衬里用组合物浸渗于基材而得到的。
发明的效果
本发明的含有乙烯基酯树脂和选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯的组合物无海洋污染等环境问题、VOC之类的问题，组合物的粘度低，操作优异，具有良好的固化速度、保存稳定性，因此，适合作为衬里用组合物。
具体实施方式
以下，对衬里用组合物进行详细说明。本发明的衬里用组合物中至少含有乙烯基酯树脂、和选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯。
本发明的衬里用组合物中使用的乙烯基酯树脂是通过环氧树脂与不饱和一元酸的反应而得到的反应产物。
作为前述环氧树脂，例如可以举出双酚A型环氧树脂、双酚F型环氧树脂等双酚型环氧树脂类、苯酚酚醛清漆型环氧树脂、甲酚酚醛清漆型环氧树脂等酚醛清漆型环氧树脂类、这些树脂的溴化环氧树脂等酚类的缩水甘油醚类、二丙二醇二缩水甘油醚、三羟甲基丙烷三缩水甘油醚、双酚A的环氧烷加成物的二缩水甘油醚、氢化双酚A的二缩水甘油醚等多元醇类的缩水甘油醚类、3,4-环氧-6-甲基环己基甲基-3,4-环氧-6-甲基环己烷羧酸酯、1-环氧乙基-3,4-环氧环己烷等脂环式环氧树脂类、邻苯二甲酸二缩水甘油酯、四氢邻苯二甲酸二缩水甘油酯、二缩水甘油-对羟基苯甲酸酯、二聚酸缩水甘油酯等缩水甘油酯类、四缩水甘油二氨基二苯基甲烷、四缩水甘油-间二甲苯二胺、三缩水甘油-对氨基苯酚、N,N-二缩水甘油苯胺等缩水甘油胺类、1,3-二缩水甘油-5,5-二甲基乙内酰脲、三缩水甘油异氰脲酸酯等杂环式环氧树脂等。另外，这些环氧树脂可以单独使用或组合使用2种以上。其中，优选双酚型环氧树脂类、更优选双酚A型环氧树脂。
作为不饱和一元酸，例如可以举出丙烯酸、甲基丙烯酸、巴豆酸、肉桂酸、丙烯酸二聚物、马来酸单甲酯、富马酸单甲酯、富马酸单环己酯、或山梨酸等。这些酸可以单独使用或组合2种以上使用。其中，优选丙烯酸、甲基丙烯酸。
乙烯基酯树脂的重均分子量(Mw)没有特别限定，优选2000～500000、更优选4000～100000。乙烯基酯树脂的数均分子量(Mn)没有特别限定，优选250～5000、更优选500～3000。需要说明的是，本说明书中，“重均分子量”和“数均分子量”如下：使用凝胶渗透色谱仪(株式会社岛津制作所制、GPC系统)在常温下测定，利用标准聚苯乙烯标准曲线可以求出。
作为乙烯基酯树脂，没有特别限定，可以单独使用或组合使用2种以上，出于可以更适合地得到本发明的效果、可以降低衬里用组合物的粘度、对基材的浸渗性也更良好的理由，作为前述环氧树脂，优选使用双酚型环氧树脂类的、双酚型乙烯基酯树脂，作为前述环氧树脂，更优选使用双酚A型环氧树脂的、双酚A型乙烯基酯树脂。
本发明的衬里用组合物中，使用选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯，优选为通式(1)所示的多官能烯丙基酯。选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯可以为1种、或组合2种以上。此处，本说明书中，多官能烯丙基酯是指，具有2个以上的烯丙基酯基(-COOCH2-CH＝CH2基)的化合物，脂肪族多官能烯丙基酯是指，具有脂肪族烃基和2个以上的烯丙基酯基的化合物，脂环式多官能烯丙基酯是指，具有脂环式烃基和2个以上的烯丙基酯基的化合物。需要说明的是，本说明书中，脂肪族多官能烯丙基酯为包含直接键合有2个烯丙基酯基的草酸二烯丙酯的概念。
[式中，n表示2～4中的任意整数，z为n价的脂肪族烃基、n价的脂环式烃基或键合部(其中，仅n是2的情况)。]
通式(1)中，n优选2或3，特别优选2。
通式(1)中，n价的脂肪族烃基的碳数优选1～18、更优选2～12、进一步优选2～6、特别优选2～4、最优选2～3。
n价的脂肪族烃基可以为饱和的n价的脂肪族烃基，也可以在一部分中具有不饱和键。其中，出于未反应直接残留的交联剂量(多官能烯丙基酯量)减少、可以使所得固化物的物性更良好的理由，优选具有不饱和键。
n价的脂肪族烃基可以具有支链结构，优选不具有支链结构的直链状的烃基。
n价的脂肪族烃基可以具有碳数为1～6的烷氧基、卤素原子、烯丙基、乙烯基、羟基等取代基，优选不具有n个的烯丙基酯基以外的取代基。
作为2价的脂肪族烃基，可以举出碳数1～18的亚烷基、亚烯基、亚炔基，优选亚烯基。作为亚烯基，可以举出亚乙烯基、1-亚丙烯基、2-亚丙烯基、1-亚丁烯基、2-亚丁烯基、1-亚戊烯基、2-亚戊烯基、1-亚己烯基、2-亚己烯基、1-亚辛烯基等。其中，优选亚乙烯基。
通式(1)中，n价的脂环式烃基的碳数优选3～18、更优选4～12、特别优选4～10。其中，构成脂环式烃基的全部碳原子优选形成环结构。即，n价的脂环式烃基优选3～18元环、更优选4～12元环、特别优选4～10元环。
n价的脂环式烃基可以为饱和的n价的脂环式烃基，也可以在一部分中具有不饱和键。其中，优选饱和的n价的脂环式烃基。需要说明的是，本发明中，脂环式是指，具备不具有芳香性的环状结构，脂环式烃基是指，具备不具有芳香性的环状结构的烃基。
n价的脂环式烃基可以具有碳数为1～6的烷基、碳数为1～6的烷氧基、卤素原子、烯丙基、乙烯基、羟基等取代基，优选不具有n个的烯丙基酯基以外的取代基。
通式(1)中，z为键合部的情况下，通式(1)所示的多官能烯丙基酯为草酸二烯丙酯。
通式(1)中，z优选n价的脂肪族烃基。
如果示例通式(1)所示的多官能烯丙基酯，则可以举出草酸二烯丙酯、丙二酸二烯丙酯、琥珀酸二烯丙酯、戊二酸二烯丙酯、己二酸二烯丙酯、庚二酸二烯丙酯、辛二酸二烯丙酯、壬二酸二烯丙酯、癸二酸二烯丙酯、富马酸二烯丙酯、马来酸二烯丙酯、柠檬酸三烯丙酯、衣康酸二烯丙酯等脂肪族多官能烯丙基酯、1,2,3,4-丁烷四羧酸四烯丙酯、环丁烷二羧酸二烯丙酯、环丁烯二羧酸二烯丙酯、环己烷二羧酸二烯丙酯(六氢邻苯二甲酸二烯丙酯)、四氢邻苯二甲酸二烯丙酯等通式(2)～通式(9)所示的化合物等脂环式多官能烯丙基酯，优选琥珀酸二烯丙酯、富马酸二烯丙酯、己二酸二烯丙酯、马来酸二烯丙酯、衣康酸二烯丙酯、环己烷二羧酸二烯丙酯(六氢邻苯二甲酸二烯丙酯)、四氢邻苯二甲酸二烯丙酯。
(式中，n为2～4中的任意整数。)
(式中，n为2～4中的任意整数。)
(式中，n为2～4中的任意整数。)
(式中，n为2～4中的任意整数。)
(式中，n为2～4中的任意整数。)
(式中，n为2～4中的任意整数。)
(式中，n为2～4中的任意整数。)
(式中，n为2～4中的任意整数。)
需要说明的是，通式(2)～(9)中的n与前述通式(1)中的n为相同含义。
式(2)～(9)中，可以在环结构内进行交联，作为在环结构内进行交联的例子，可以举出金刚烷、降冰片烷等。
式(2)～(9)的环上的COOCH2-CH＝CH2基的取代位置可以为任何组合，也可以为它们的混合物。特别是，2个COOCH2-CH＝CH2基与6元环键合时，2个COOCH2-CH＝CH2基可以为邻取向或间取向或对取向中的任一者，优选邻取向或对取向。
作为脂环式多官能烯丙基酯，可以举出环丁烷二羧酸二烯丙酯、环庚烷二羧酸二烯丙酯、环己烷二羧酸二烯丙酯(六氢邻苯二甲酸二烯丙酯)、降冰片烷二羧酸二烯丙酯、环丁烯二羧酸二烯丙酯、环庚烯二羧酸二烯丙酯、环己烯二羧酸二烯丙酯(四氢邻苯二甲酸二烯丙酯)、降冰片烯二羧酸二烯丙酯、3-甲基-六氢-1,2-邻苯二甲酸二烯丙酯、4-甲基-六氢-1,2-邻苯二甲酸二烯丙酯、3-甲基-1,2,3,6-四氢-1,2-邻苯二甲酸二烯丙酯、4-甲基-1,2,3,6-四氢-1,2-邻苯二甲酸二烯丙酯、3,6-内亚甲基-3-甲基-1,2,3,6-四氢-1,2-邻苯二甲酸二烯丙酯、3,6-内亚甲基-4-甲基-1,2,3,6-四氢-1,2-邻苯二甲酸二烯丙酯、4-环己烯-1,2-二羧酸二烯丙酯、2-环己烯-1,2-二羧酸二烯丙酯、1,2,3,4-丁烷四羧酸四烯丙酯等。其中，优选1,2-环己烷二羧酸二烯丙酯、1,3-环己烷二羧酸二烯丙酯、1,4-环己烷二羧酸二烯丙酯、降冰片烷二羧酸二烯丙酯。
本发明的选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯可以如下制造：使下述通式(10)所示的羧酸化合物、或它们的酸酐与烯丙基卤化物或烯丙基醇例如在酸性物质、碱性物质、催化剂、溶剂的存在下反应而制造。通式(10)所示的羧酸化合物可以以试剂、工业药品的形式获得。
[式中，关于n和z，与前述通式(1)中的n和z为相同含义。]
作为烯丙基卤化物，例如可以举出烯丙基氯、烯丙基溴、烯丙基碘等。烯丙基卤化物的用量没有特别限制，相对于通式(10)所示的羧酸化合物，通常优选2～20当量的范围，从反应速度和容积效率的观点出发，更优选2.3～10当量的范围。这些烯丙基卤化物化合物可以以试剂、工业药品的形式获得。
烯丙基醇可以以试剂、工业药品的形式获得。对烯丙基醇的用量没有特别限制，相对于通式(10)所示的羧酸化合物，通常优选2～10当量的范围、更优选2～5当量的范围。
作为酸性物质，可以举出对甲苯磺酸、十二烷基苯磺酸、硫酸，酸性物质的用量相对于通式(10)所示的羧酸化合物，优选0.001～0.1当量的范围、更优选0.005～0.05当量的范围。
作为碱性物质，例如一般使用氢氧化钠、氢氧化钾等碱金属的氢氧化物；氢化钠、氢化钾等碱金属的氢化物、碳酸钠、碳酸钾等碳酸化物、碳酸氢钠、碳酸氢钾等碳酸氢化物、醇化物等，也可以使用季铵化合物、脂肪族胺、芳香族胺那样的有机碱。碱性物质的用量相对于通式(10)所示的羧酸化合物，优选0.5～30当量的范围、更优选2～15当量的范围。
作为催化剂，例如可以使用铜、铁、钴、镍、铬、钒等过渡金属、过渡金属盐，其中，适合使用铜化合物。
作为铜化合物，没有特别限定，可以使用大部分的铜化合物，优选氯化亚铜、溴化亚铜、氧化亚铜、碘化亚铜、氰化亚铜、硫酸亚铜、硫酸铜、氯化铜、氢氧化铜、溴化铜、磷酸铜、硝酸亚铜、硝酸铜、碳酸铜、乙酸亚铜、乙酸铜等。其中，从能容易获得且廉价的方面出发，特别适合的是氯化亚铜、氯化铜、溴化亚铜、溴化铜、碘化亚铜、硫酸铜、乙酸铜。
反应可以在溶剂的存在下或不存在下实施。作为溶剂，只要对反应不造成不良影响就没有特别限制，例如可以举出苯、甲苯、二甲苯等芳香族烃；己烷、庚烷、辛烷、环己烷、甲基环己烷等饱和脂肪族烃；二乙基醚、二乙二醇二甲基醚、1,4-二氧杂环己烷、四氢呋喃等醚；乙酸乙酯、乙酸丁酯等酯；二氯甲烷、氯仿、四氯化碳等卤代烃；二甲基甲酰胺、N-甲基吡咯烷酮、环丁砜等。它们可以单独使用一种，也可以组合使用二种以上。使用溶剂时，对其用量没有特别限制，相对于通式(10)所示的羧酸化合物，通常优选0.01～20倍重量的范围、更优选0.1～10倍重量的范围。本反应的情况下，即使不特别使用溶剂也可以效率良好地制造选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯。
将碱性物质制成水溶液用于反应时，为了促进反应，特别优选使用相转移催化剂。对相转移催化剂没有特别限制，例如可以举出三辛基甲基氯化铵、四丁基氯化铵、四丁基溴化铵等季铵盐；四丁基氯化鏻等鏻盐；15-冠-5、18-冠-6等冠醚等。使用相转移催化剂时，其用量相对于通式(10)所示的羧酸化合物，通常优选0.001～1当量的范围、更优选0.01～0.4当量的范围。
在得到充分的反应速度、且有效地抑制副反应而得到高收率的含义上，反应温度通常优选-30～150℃的范围、更优选-10～120℃的范围。另外，反应时间优选10分钟～15小时的范围，从抑制副反应的观点出发，优选10分钟～10小时的范围。
反应优选在氮气、氩气那样的非活性气体气氛下实施。另外，反应可以在大气压下实施也可以在加压下实施，从制造设备方面的观点出发，优选在大气压下实施。反应例如可以如下进行：在搅拌型反应装置中一次性或分批投入原料，在上述第9页第7～13行记载的规定温度下使其反应规定时间从而可以进行。
反应结束后，将所得反应混合液中和后，根据需要用水、饱和食盐水等清洗后浓缩，进一步进行蒸馏、柱色谱法等有机化合物的纯化中通常使用的纯化操作，从而可以取得纯度高的选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯。
本发明的衬里用组合物中，相对于乙烯基酯树脂100重量份，优选含有20重量份以上的选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯、更优选含有25重量份以上、特别优选含有35重量份以上、优选含有80重量份以下、更优选含有75重量份以下、特别优选含有70重量份以下。
本发明的衬里用组合物中，在选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯的基础上，可以根据需要使用多官能(甲基)丙烯酸酯。通过配混多官能(甲基)丙烯酸酯，可以进一步加快固化速度。
此处，本说明书中，多官能(甲基)丙烯酸酯是指，具有2个以上(甲基)丙烯酸酯基的化合物。需要说明的是，(甲基)丙烯酸酯是指，丙烯酸酯和甲基丙烯酸酯中的一者或两者。
作为多官能(甲基)丙烯酸酯，可以举出新戊二醇二丙烯酸酯、新戊二醇二甲基丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、乙二醇二甲基丙烯酸酯、二乙二醇二甲基丙烯酸酯、1,3-丁二醇二甲基丙烯酸酯、1,6-己二醇二甲基丙烯酸酯、1,6-己二醇二丙烯酸酯等。另外，这些多官能(甲基)丙烯酸酯可以单独使用，也可以组合使用2种以上。
多官能(甲基)丙烯酸酯所具有的(甲基)丙烯酸酯基的数量优选2～6、更优选2～4。
作为多官能(甲基)丙烯酸酯，出于未反应而直接残留的交联剂量(多官能烯丙基酯量、多官能(甲基)丙烯酸酯量)减少、可以使所得固化物的物性更良好的理由，优选多官能甲基丙烯酸酯。
本发明的衬里用组合物中，相对于乙烯基酯树脂100重量份，优选含有5重量份以上的多官能(甲基)丙烯酸酯、更优选含有10重量份以上、特别优选含有12重量份以上、优选含有80重量份以下、更优选含有75重量份以下、特别优选含有70重量份以下。
本发明的衬里用组合物中，可以没有限定地使用热聚合引发剂、光聚合引发剂。
作为热聚合引发剂，没有特别限定，优选过氧化物化合物、偶氮化合物，具体而言，可以举出苯甲酰过氧化物、月桂酰过氧化物等二酰基过氧化物类、二枯基过氧化物、二叔丁基过氧化物等二烷基过氧化物类、过氧化二碳酸二异丙酯、过氧化二碳酸双(4-叔丁基环己基)酯等过氧化碳酸酯类、过氧化辛酸叔丁酯、过氧化苯甲酸叔丁酯等过氧化烷基酯类等过氧化物化合物、1,1’-偶氮双环己烷-1-腈、2,2’-偶氮双-(2,4-二甲基戊腈)、2,2’-偶氮双-(4-甲氧基-2,4-二甲基戊腈)、2,2’-偶氮双-(甲基异丁酯)、α,α-偶氮双-(异丁腈)、4,4’-偶氮双-(4-氰基戊酸)等偶氮化合物。另外，这些热聚合引发剂可以单独使用，也可以组合使用2种以上。
本发明的衬里用组合物中，相对于乙烯基酯树脂100重量份，优选含有0.001重量份以上的热聚合引发剂、更优选含有0.005重量份以上、进一步优选含有0.01重量份以上、特别优选含有0.5重量份以上、优选含有10重量份以下、更优选含有8重量份以下、特别优选含有5重量份以下。
作为光聚合引发剂，没有特别限定，优选苯偶姻醚化合物、二苯甲酮化合物、苯乙酮化合物、噻吨酮化合物，可以举出苯偶姻烷基醚等苯偶姻醚化合物、二苯甲酮、苯偶酰、甲基邻苯甲酰苯甲酸酯等二苯甲酮化合物、苯偶酰二甲基缩酮、2,2-二乙氧基苯乙酮、2-羟基-2-甲基苯丙酮、4-异丙基-2-羟基-2-甲基苯丙酮、1,1-二氯苯乙酮等苯乙酮化合物、2-氯噻吨酮、2-甲基噻吨酮、2-异丙基噻吨酮等噻吨酮化合物。
光聚合引发剂中，可以组合使用金属皂类、金属螯合物类、苯胺类、胺类作为促进剂。具体而言，可以举出环烷酸钴、辛基酸钴、辛基酸锌、辛基酸钒、环烷酸铜、环烷酸钡等金属皂类、乙酰乙酸钒、乙酰乙酸钴、乙酰丙酮化铁等金属螯合物类、苯胺、N,N-二甲基苯胺、N,N-二乙基苯胺、对甲苯胺、N,N-二甲基-对甲苯胺、N,N-双(2-羟基乙基)-对甲苯胺、4-(N,N-二甲基氨基)苯甲醛、4-[N,N-双(2-羟基乙基)氨基]苯甲醛、4-(N-甲基-N-羟基乙基氨基)苯甲醛、N,N-双(2-羟基丙基)-对甲苯胺、N-乙基-间甲苯胺、三乙醇胺、间甲苯胺、二亚乙基三胺、吡啶、4-苯基吗啉、哌啶、N,N-双(羟基乙基)苯胺、二乙醇苯胺等苯胺类、N,N-取代-对甲苯胺、4-(N,N-取代氨基)苯甲醛等胺类。另外，这些光聚合引发剂可以单独使用，也可以组合使用2种以上。
本发明的衬里用组合物中，相对于乙烯基酯树脂100重量份，优选含有0.001重量份以上的光聚合引发剂、更优选含有0.005重量份以上、特别优选含有0.01重量份以上、优选含有10重量份以下、更优选含有8重量份以下、特别优选含有5重量份以下。
另外，本发明的衬里用组合物中，在不妨碍本发明的效果的范围内也可以包含增稠剂、着色剂、增塑剂、填充剂、阻燃剂等。
对使用本发明的衬里用组合物的衬里方法没有特别限定，可以举出如下方法：利用流体压力等将包含浸渗有本发明的衬里用组合物的基材的衬里材料插入至既定管内，在既定管内面内覆并压接，进行加热或光照射，形成强化塑料管。
即，为一种衬里方法，其特征在于，将衬里材料插入至既定管内并将既定管内衬里的方法中，包括如下工序：使本发明的衬里用组合物浸渗于基材的工序；将由浸渗得到的衬里材料插入至既定管内的工序；和，对插入的衬里材料进行加热或光照射，将既定管内被覆的工序。
作为使衬里用组合物浸渗的基材，只要为可以浸渗本发明的衬里用组合物的基材就没有特别限定，可以使用无纺布、毡、短切原丝垫等，可以举出聚烯烃系、聚酯系、聚酰胺系、芳香族系树脂等无纺布、聚酯、聚酰胺、聚丙烯等毡、玻璃纤维、碳纤维、金属纤维等无机系纤维、芳族聚酰胺纤维、聚酯纤维、乙烯基酯纤维、使用聚乙烯、聚丙烯等烯烃系纤维的短切原丝垫。无纺布、毡、短切原丝垫可以组合而形成层来使用。
作为使衬里用组合物浸渗于基材的方法，没有特别限定。通过使衬里用组合物与基材接触，衬里用组合物浸渗于基材。例如，通过使基材浸渍于衬里用组合物溶液，可以使衬里用组合物浸渗于基材。
另外，本发明的衬里材料通过使本发明的衬里用组合物浸渗于基材而得到，可以为在其单面、或两面用聚氨酯等透过性塑料薄膜覆盖的构成。
将通过浸渗而得到的衬里材料插入至既定管内的工序中，对于其方法没有特别限制，可以示例日本特开2003-165158号公报等中记载的方法。即，可以举出：使衬里材料形成平坦状，在密闭容器内以折叠并堆积的状态配置，将其一端向外侧折回，将其安装于与前述密闭容器连接的倒置喷嘴的开口端外周，使水压等流体压作用于前述密闭容器内，将管衬里材料倒置插入至管路内，形成将衬里材料挤压至管路内面的状态等。
对插入的衬里材料进行加热或光照射，将既定管内被覆的工序中，对加热·光照射的方法没有特别限定。
衬里材料中，使衬里用组合物热固化的情况下，可以举出通过供给加压蒸汽而使其固化的方法；通过供给热水而使其固化的方法等。
衬里材料中，使衬里用组合物光固化的情况下，通过使持续照射紫外线的光源在管路内以一定速度移动，管体衬里材料固化，在管体内部形成结构物。作为来自光放射源的照射时间，根据光源的有效波长区域、输出、照射距离、衬里材料的厚度等而不同，为0.05～1小时。
另外，通过在被衬里体(衬里对象物)上直接涂布衬里用组合物，进行加热或光照射，从而也可以进行衬里。需要说明的是，对于加热或光照射，可以以与上述第13页第11～13行同样的方法·条件进行。
在被衬里体(衬里对象物)上涂布衬里用组合物时，通过使用球形或胶囊型的生铁块、使用加压、或利用抽吸的气流，从而可以更均匀地进行涂布。
以下，根据实施例对本发明更详细地进行说明，但本发明不受实施例的任何限定。
以下说明后述的实施例和比较例中使用的材料。
乙烯基酯树脂
乙烯基酯树脂：昭和电工株式会社制RIPOXY VR-90(双酚A型乙烯基酯树脂、数均分子量＝1000、软化点＝60℃)
引发剂
过氧化二碳酸双(4-叔丁基环己基)酯：KAYAKU AKZO CO.,LTD.制Perkadox 16
过氧化苯甲酸叔丁酯：日油株式会社制Perbutyl Z
交联剂
邻苯二甲酸二烯丙酯：株式会社大阪曹达制DAISO DAP monomer
马来酸二烯丙酯：和光纯药工业株式会社制
富马酸二烯丙酯：合成例1
琥珀酸二烯丙酯：合成例2
己二酸二烯丙酯：合成例3
衣康酸二烯丙酯：合成例4
1,2-环己烷二羧酸二烯丙酯：合成例5
1,4-环己烷二羧酸二烯丙酯：合成例6
1,6-己二醇二甲基丙烯酸酯：共荣社株式会社制
合成例1：富马酸二烯丙酯的合成
在500mL的烧瓶中投入烯丙基醇145.2g(2.50mol)、甲苯137.5(1.49mol)、富马酸116.1g(1.00mol)、十二烷基苯磺酸6.53g(0.02mol)，用磁搅拌子搅拌并在油浴中回流。24小时后停止加热，将烧瓶冷却。对所得反应液进行中和、水洗，将低沸成分用旋转蒸发仪蒸馏去除，将所得浓缩液减压蒸馏，从而得到目标富马酸二烯丙酯74.0g。将所得化合物用于实施例2。
合成例2：琥珀酸二烯丙酯的合成
在500mL的烧瓶中投入烯丙基醇159.7g(2.75mol)、甲苯151.3(1.64mol)、琥珀酸酐110.1g(1.10mol)、十二烷基苯磺酸7.18g(0.022mol)，用磁搅拌子搅拌并在油浴中回流。8小时后停止加热，将烧瓶冷却。对所得反应液进行中和、水洗，将低沸成分用旋转蒸发仪蒸馏去除，将所得浓缩液减压蒸馏，从而得到目标琥珀酸二烯丙酯184.4g。将所得化合物用于实施例3。
合成例3：己二酸二烯丙酯的合成
在500mL的烧瓶中投入烯丙基醇159.7g(2.75mol)、甲苯151.3(1.64mol)、己二酸146.1g(1.00mol)、十二烷基苯磺酸7.18g(0.022mol)，用磁搅拌子搅拌并在油浴中回流。10小时后停止加热，将烧瓶冷却。对所得反应液进行中和、水洗，将低沸成分用旋转蒸发仪蒸馏去除，将所得浓缩液减压蒸馏，从而得到目标己二酸二烯丙酯181.0g。将所得化合物用于实施例4。
合成例4：衣康酸二烯丙酯的合成
在500mL的烧瓶中投入烯丙基醇275.9g(4.75mol)、甲苯261.3(2.83mol)、衣康酸248.9g(1.90mol)、十二烷基苯磺酸12.41g(0.038mol)，用磁搅拌子搅拌并在油浴中回流。30小时后停止加热，将烧瓶冷却。对所得反应液进行中和、水洗，将低沸成分用旋转蒸发仪蒸馏去除，将所得浓缩液减压蒸馏，从而得到目标衣康酸二烯丙酯145g。将所得化合物用于实施例5。
合成例5：1,2-环己烷二羧酸二烯丙酯的合成
在500mL的烧瓶中投入烯丙基醇150.5g(2.59mol)、甲苯160.5(1.74mol)、1,2-环己烷二羧酸酐200.0g(1.30mol)、十二烷基苯磺酸7.18g(0.022mol)，用磁搅拌子搅拌并在油浴中回流。10小时后停止加热，将烧瓶冷却。对所得反应液进行中和、水洗，将低沸成分用旋转蒸发仪蒸馏去除，将所得浓缩液减压蒸馏，从而得到目标1,2-环己烷二羧酸二烯丙酯124.1g。将所得化合物用于实施例6。
合成例6：1,4-环己烷二羧酸二烯丙酯的合成
在500mL的烧瓶中投入烯丙基醇170.5g(2.93mol)、甲苯150.1(1.63mol)、1,4-环己烷二羧酸241.1g(1.40mol)、十二烷基苯磺酸7.18g(0.022mol)，用磁搅拌子搅拌并在油浴中回流。20小时后停止加热，将烧瓶冷却。对所得反应液进行中和、水洗，将低沸成分用旋转蒸发仪蒸馏去除，将所得浓缩液减压蒸馏，从而得到目标1,4-环己烷二羧酸二烯丙酯110.6g。将所得化合物用于
实施例7。
引发剂稀释剂
邻苯二甲酸二烯丙酯：株式会社大阪曹达制DAISO DAP monomer
将实施例和比较例中使用的乙烯基酯树脂组合物的成分的组成示于表1。表内组成的数值单位为重量份，()内数字为相对于乙烯基酯树脂100重量份的重量份。
[表1]
单位：重量份
衬里用组合物的制备
按照表1所示的组成，分别称量树脂和交联剂使得乙烯基酯树脂与交联剂的重量总计成为50g，使用行星式磨机(KURABO INDUSTRIES LTD.制Mazerustar KK250S)混炼总计5分钟。接着，加温至80～90℃，并且利用行星式磨机进行搅拌直至乙烯基酯树脂溶解于交联剂。乙烯基酯树脂溶解于交联剂成为均匀后停止加温和搅拌，冷却直至室温。冷却直至室温后，添加用引发剂稀释剂稀释的引发剂，用行星式磨机进行搅拌使其不过度具有30℃以上的热，制备衬里用组合物。
粘度测定
所得衬里用组合物的粘度如下测定：使用E型粘度计BROOKFIELD RV DV2T，在锥角3°、半径12mm、温度25℃的条件下读取转速1rpm下的粘度，从而测定。将结果示于表2。
另外，将在衬里用组合物制备后的0小时后、18小时后以25℃保管时的粘度示于表3。
高温固化特性试验
在外径18mm×高度165mm的试验管(型号：P-18SM(日电理化硝子株式会社制))中，注入衬里用组合物直至距离底部7.62cm的位置，使K型热电偶对准所注入的树脂的高度的中心部(距离底部3.81cm)的位置。接着，在加温至65.5℃的油浴中以所注入的树脂的液面成为油浴的液面的1cm下的方式，调节试验管的高度，记录凝胶化时间(60.0℃～71.1℃为止的时间)、固化时间(60.0℃～最高达到温度为止的时间)、最高达到温度。将测定结果示于表2。
拉伸弹性模量测定
制作纵×横×厚为5mm×22mm×1mm的衬里用组合物的固化物试验片，根据参考JIS K 7161将其进行拉伸试验时得到的应力-应变曲线的斜率算出拉伸弹性模量。试验片如下制作：准备具有上述尺寸的浇铸框的由聚二甲基硅氧烷形成的块，向其中注入上述衬里用组合物，在80℃恒温烘箱内使其固化8小时，从而制作。拉伸试验使用Toyo SeikiSeisaku-sho,Ltd.制Strograph E3-L，以拉伸速度20mm/分钟进行测定。测定结果示于表4。
[表2]
[表3]
如表2所示那样，使用选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯的实施例1～7与比较例1相比，衬里用组合物的粘度低，操作优异。即，暗示了，相对于乙烯基酯树脂，通式(1)所示的多官能烯丙基酯的稀释性优异，为了降低粘度，也可以不过剩加入交联剂，不会破坏进行衬里时的固化物的物性，因此，是非常有用的。
需要说明的是，比较例1中，衬里用组合物的粘度高，因此，对基材的浸渗耗费工夫，而实施例1～7中，衬里用组合物的粘度低，因此，可以容易进行对基材的浸渗。
另外，如表2所示那样，使用选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯的实施例1～7与比较例1相比，凝胶化时间和最高达到温度为止的时间(固化时间)短，反应性优异。
进而，如表2所示那样，实施例2中，最高达到温度高，暗示了，利用产生的热量，容易加速度地推进反应，参与反应的交联剂增加，因此暗示了，降低未反应交联剂的残留率，可以得到良好的固化物的物性。
如表3所示那样，使用选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯的实施例1～7与比较例1相比，粘度变化量少，保存稳定性优异。
[表4]
如表4所示那样，使用选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯的实施例1～7与比较例1相比，拉伸弹性模量显示出高的值，作为衬里结构材料是优异的。
产业上的可利用性
将下水道管、上水道管、农业用水管、燃气管道等埋设管等各种既定管的内周面复原时，本发明的衬里材料用组合物是有用的。
Claims (5)
1.一种衬里用组合物，其特征在于，含有：
乙烯基酯树脂；和，
选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯。
2.根据权利要求1所述的衬里用组合物，其特征在于，选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯为通式(1)所示的多官能烯丙基酯，
式中，n表示2～4中的任意整数，z为n价的脂肪族烃基、n价的脂环式烃基或键合部，其中，仅n是2的情况下z为键合部。
3.根据权利要求1或2所述的衬里用组合物，其特征在于，选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯为琥珀酸二烯丙酯、富马酸二烯丙酯、马来酸二烯丙酯、衣康酸二烯丙酯、己二酸二烯丙酯、环己烷二羧酸二烯丙酯中的任意者。
4.根据权利要求1～3中任一项所述的衬里用组合物，其特征在于，相对于乙烯基酯树脂100重量份，含有20重量份以上且80重量份以下的选自脂肪族多官能烯丙基酯和脂环式多官能烯丙基酯中的多官能烯丙基酯。
5.一种衬里材料，其特征在于，其是使权利要求1～4中任一项所述的衬里用组合物浸渗于基材而得到的。
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| PCT/JP2016/066613 WO2017013950A1 (ja) | 2015-07-21 | 2016-06-03 | ライニング用組成物 |
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| WO2017169661A1 (ja) * | 2016-03-31 | 2017-10-05 | 株式会社大阪ソーダ | 光硬化性樹脂組成物、及びその硬化物 |
| JP2021105068A (ja) * | 2018-03-30 | 2021-07-26 | 株式会社大阪ソーダ | 熱硬化性樹脂組成物 |
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| EP0143216A2 (en) * | 1983-09-06 | 1985-06-05 | The Dow Chemical Company | Polymer compositions, methods for lining pipes and for filling girthweld concrete cutbacks, and a reusable mould for filling said cutbacks |
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| JPS4939177B1 (zh) * | 1970-12-08 | 1974-10-23 | ||
| CA1171191A (en) * | 1981-04-03 | 1984-07-17 | Larry C. Muszynski | Polymer concrete compositions and their use in preparing articles |
| US5134175A (en) * | 1987-12-16 | 1992-07-28 | Michael Lucey | Curable composition for electrical and electronic components |
| US5925409A (en) * | 1997-08-27 | 1999-07-20 | Reichhold, Inc. | Resins for lining surfaces |
| JP5189379B2 (ja) * | 2008-02-20 | 2013-04-24 | リンテック株式会社 | 樹脂組成物及びこれを用いたフィルム、ならびにフィルムの製造方法 |
| CN102027231B (zh) * | 2008-05-16 | 2013-07-03 | 陶氏环球技术公司 | 风车螺旋桨叶片及其制造方法 |
| JP6372922B2 (ja) * | 2012-12-27 | 2018-08-15 | 昭和電工株式会社 | 樹脂組成物、それを用いた被覆工法およびその方法により被覆された被覆構造体 |
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| EP0143216A2 (en) * | 1983-09-06 | 1985-06-05 | The Dow Chemical Company | Polymer compositions, methods for lining pipes and for filling girthweld concrete cutbacks, and a reusable mould for filling said cutbacks |
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| CN111868123A (zh) * | 2018-03-28 | 2020-10-30 | 株式会社大阪曹达 | 热固化性树脂组合物 |
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| US20180186064A1 (en) | 2018-07-05 |
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| EP3326784A1 (en) | 2018-05-30 |
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