JP2016529350A - 改良した表面硬化特性を有するフリーラジカルコーティング組成物 - Google Patents
改良した表面硬化特性を有するフリーラジカルコーティング組成物 Download PDFInfo
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- JP2016529350A JP2016529350A JP2016524832A JP2016524832A JP2016529350A JP 2016529350 A JP2016529350 A JP 2016529350A JP 2016524832 A JP2016524832 A JP 2016524832A JP 2016524832 A JP2016524832 A JP 2016524832A JP 2016529350 A JP2016529350 A JP 2016529350A
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- acrylate
- monomer
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- 150000003254 radicals Chemical class 0.000 title claims description 13
- 239000008199 coating composition Substances 0.000 title description 15
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- 239000000178 monomer Substances 0.000 claims abstract description 79
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 62
- 238000004132 cross linking Methods 0.000 claims abstract description 43
- 150000002978 peroxides Chemical class 0.000 claims abstract description 34
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 31
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 9
- 238000000576 coating method Methods 0.000 claims description 50
- 239000011248 coating agent Substances 0.000 claims description 35
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
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- 239000002904 solvent Substances 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 14
- 229910017052 cobalt Inorganic materials 0.000 claims description 11
- 239000010941 cobalt Substances 0.000 claims description 11
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 11
- 239000004567 concrete Substances 0.000 claims description 11
- 239000000565 sealant Substances 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011253 protective coating Substances 0.000 claims description 8
- 229920001567 vinyl ester resin Polymers 0.000 claims description 8
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical group CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 claims description 7
- 150000004696 coordination complex Chemical class 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 6
- BDKDHWOPFRTWPP-UHFFFAOYSA-N 2,2-bis(prop-2-enoxymethyl)butan-1-ol Chemical group C=CCOCC(CO)(CC)COCC=C BDKDHWOPFRTWPP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 claims description 3
- SGLXWMAOOWXVAM-UHFFFAOYSA-L manganese(2+);octanoate Chemical compound [Mn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O SGLXWMAOOWXVAM-UHFFFAOYSA-L 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
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- 238000010030 laminating Methods 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims 1
- 239000008393 encapsulating agent Substances 0.000 claims 1
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- -1 allyl ester Chemical class 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
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- 238000000034 method Methods 0.000 description 12
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- 239000000463 material Substances 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 6
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- 239000012855 volatile organic compound Substances 0.000 description 6
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- 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 4
- KEHNRUNQZGRQHU-UHFFFAOYSA-N 4-oxopentanal Chemical compound CC(=O)CCC=O KEHNRUNQZGRQHU-UHFFFAOYSA-N 0.000 description 4
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
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- 239000004925 Acrylic resin Substances 0.000 description 3
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 3
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
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- 238000004806 packaging method and process Methods 0.000 description 3
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical class NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- UEEXJPSXCVCMBY-UHFFFAOYSA-N 3,3-dimethylundecan-6-yl hydroxy carbonate Chemical compound CCCCCC(OC(=O)OO)CCC(C)(C)CC UEEXJPSXCVCMBY-UHFFFAOYSA-N 0.000 description 2
- 240000002834 Paulownia tomentosa Species 0.000 description 2
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
- 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 2
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 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
- 125000000524 functional group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000002383 tung oil Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- XTJDUBPOTVNQPI-UHFFFAOYSA-N (2-nonylphenyl) 2-methylprop-2-enoate Chemical class CCCCCCCCCC1=CC=CC=C1OC(=O)C(C)=C XTJDUBPOTVNQPI-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- CYXMOAZSOPXQOD-UHFFFAOYSA-N 1-methyl-2-(2-methylphenoxy)benzene Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1C CYXMOAZSOPXQOD-UHFFFAOYSA-N 0.000 description 1
- HYQASEVIBPSPMK-UHFFFAOYSA-N 12-(2-methylprop-2-enoyloxy)dodecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCCOC(=O)C(C)=C HYQASEVIBPSPMK-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
- 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
- LELKUNFWANHDPG-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxymethyl)oxirane;prop-2-enoic acid Chemical compound OC(=O)C=C.C1OC1COCC1CO1 LELKUNFWANHDPG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-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
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical class C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
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- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 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
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 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 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
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- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 1
- MKVYSRNJLWTVIK-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O MKVYSRNJLWTVIK-UHFFFAOYSA-N 0.000 description 1
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- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
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- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 1
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- 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
- 230000001681 protective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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Classifications
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- 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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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
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- C08F222/10—Esters
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Abstract
Description
メタクリレートモノマーに基づく二成分過酸化物硬化性コーティング組成物を表1に従って調製した。部分Aの成分は均一になるまで低いせん断力で記載した順番で一緒に混合した。本発明の表面硬化促進剤としてのジアリルトリメチロールプロパンエーテルメタクリレートを、実施例1の組成物の部分Aに対して17重量%添加した。比較例2には、表面硬化剤としてのジシクロペンテニルメタクリレート。部分Bは、最初にテトラアリルウレタンオリゴマーを強制空気オーブン内で40℃に温め、次いで、それをクメンヒドロペルオキシド開始剤にゆっくり添加し、そして均一になるまで低いせん断力で混合して調製した。次いで、部分Aおよび部分Bは均一になるまで低いせん断力で一緒に混合した。
繊維複合材料のためのゲルコートとして有用であるビニルエステル樹脂に基づく二成分過酸化物熱硬化コーティング組成物を表2に従って調製した。最初に、PRO10364ビニルエステル樹脂を強制空気オーブンで50℃に温めて部分Aを調製した。次いで、ビニルエステル樹脂をSR349 3モル−エチレンオキシドビスフェノールAジメタクリレートに添加し、そしてSR206 エチレングリコールジメタクリレート(比較例4)および本発明のジアリルメタクリレート表面硬化促進剤(実施例3)をそれぞれ添加した。次いで、1.0pbwの6%2−エチルヘキシル酸コバルトおよび0.05pbwのジメチル−パラ−トルイジン(DMPT)を各々の部分Aに添加し、均一になるまで低いせん断力で混合した。クメンヒドロペルオキシドおよびtert−アミルエチルヘキシルペルオキシカーボネートを手作業によりガラス棒で攪拌することによって均一になるまで混合して、部分Bを調製した。
コンクリートまたは金属のための保護白色上塗りとして有用であるウレタンメタクリレートオリゴマーに基づく二成分過酸化物硬化性コーティング組成物は表3に従って調製した。部分Aは最初に、顔料分散剤として湿潤分散剤を用いて、TiO2顔料をウレタンジメタクリレートオリゴマーに高速分散ミキサーで分散させて調製した。配合物は、次いでSR834ジメタクリレートモノマーおよびジアリルメタクリレートモノマーでレットダウンした(letdown)。次いで、0.3pbwの6%の2−エチルヘキシル酸コバルトおよび0.1pbwのジMPTを添加し、均一になるまで低いせん断力で混合した。部分Bは、最初にテトラアリルウレタンを強制空気オーブンで40℃に温め、次いで、それをクメンヒドロペルオキシド開始剤およびtert−アミルエチルヘキシルペルオキシカーボネート開始剤にゆっくり添加し、均一になるまで低いせん断力で混合して調製した。次いで、部分Aと部分Bは均一になるまで低いせん断力で一緒に混合した。
Claims (23)
- 架橋モノマーおよび少なくとも1つの(メタ)アクリレートモノマーを含む組成物であって、前記架橋モノマーが少なくとも2個のアリル基、好ましくは2から10個、さらに好ましくは2から6個、よりさらに好ましくは2から4個のアリル基および少なくとも1個の(メタ)アクリレート基、好ましくは1から5個、さらに好ましくは1から3個の(メタ)アクリレート基を含む二重官能性モノマーである、組成物。
- 前記架橋モノマーが、少なくとも2個のアリル基および少なくとも2個の(メタ)アクリレート基を含む、請求項1に記載の組成物。
- 前記架橋モノマーが、トリメチロールプロパン、ペンタエリスリトール(PET)、ジトリメチロールプロパン(ジTMP)、ジペンタエリスリトール(ジPET)、対応するアルコキシ化ポリオールまたはこれらの混合物の群からなる選択されるポリオールのポリアリルグリシジルエーテルから調製される、請求項1または2に記載の組成物。
- 架橋モノマーが、ジアリルトリメチロールプロパンエーテル(メタ)アクリレートである、請求項1から3のいずれか一項に記載の組成物。
- 組成物が、ウレタン(メタ)アクリレートオリゴマーをさらに含む、請求項1から4のいずれか一項に記載の組成物。
- 組成物が、ビニルエステルをさらに含む、請求項1から5のいずれか一項に記載の組成物。
- 架橋モノマーが、約400ダルトン未満、好ましくは約350ダルトン未満、さらに好ましくは約300ダルトン未満の分子量を有する、請求項1から6のいずれか一項に記載の組成物。
- 組成物が、溶媒を含まない、請求項1から7のいずれか一項に記載の組成物。
- 組成物が、金属錯体ドライヤーをさらに含む、請求項1から8のいずれか一項に記載の組成物。
- 前記金属錯体ドライヤーが、ナフテン酸コバルト、オクチル酸コバルト、ナフテン酸バナジウム、オクチル酸バナジウム、ナフテン酸マンガンまたはオクチル酸マンガンからなる群から選択される、好ましくはナフテン酸コバルトまたはオクチル酸コバルトからなる群から選択される、請求項9に記載の組成物。
- 前記少なくとも1つの(メタ)アクリレートモノマーが、2個を超える(メタ)アクリレート官能基を有する、請求項1から10のいずれか一項に記載の組成物。
- 組成物が、テトラアリルウレタンオリゴマーをさらに含む、請求項1から11のいずれか一項に記載の組成物。
- 組成物が、顔料をさらに含む、請求項1から12のいずれか一項に記載の組成物。
- 組成物が、スチレンを含まない、請求項1から13のいずれか一項に記載の組成物。
- 部分Aおよび部分Bを含む二成分フリーラジカル硬化性組成物であって、部分Aが請求項1から14のいずれか一項に記載の少なくとも1つの組成物を含み、および部分Bが有機過酸化物開始剤を含む、二成分フリーラジカル硬化性組成物。
- 前記部分Aまたは/および前記部分Bが、テトラアリルウレタンオリゴマーをさらに含む、請求項15に記載の二成分フリーラジカル硬化性組成物。
- 請求項1から4または7のいずれか一項に定義される、架橋モノマー。
- コンクリートコーティングのための、特に装飾コーティングもしくは保護コーティングのための、コンクリートシーリングおよび修復のための、繊維複合材料におけるゲルコートおよび積層用樹脂のための、または木材、プラスチック、金属のための装飾コーティングもしくは保護コーティングのための、または絶縁保護コーティングのための、およびカプセル材料のための、請求項1から14のいずれか一項に記載の組成物、請求項15もしくは16に記載の二成分組成物、または請求項17に記載の架橋モノマーの使用。
- 過酸化物硬化性組成物のための、請求項18に記載の使用。
- 請求項1から14のいずれか一項に記載の少なくとも1つの組成物、または請求項15もしくは16に記載の少なくとも1つの二成分組成物、または請求項17に記載の少なくとも1つの架橋モノマーを含む、コーティング硬化性組成物。
- 請求項1から14のいずれか一項に記載の少なくとも1つの組成物、または請求項15もしくは16に記載の少なくとも1つの二成分組成物、または請求項17に記載の少なくとも1つの架橋モノマーを含む、シーラント硬化性組成物。
- 請求項1から14のいずれか一項に記載の少なくとも1つの組成物、または請求項15もしくは16に記載の少なくとも1つの二成分組成物、または請求項17に記載の少なくとも1つの架橋モノマーが硬化した、架橋(硬化)製品。
- コーティングまたはシーラントから選択される、請求項22に記載の架橋製品。
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CN107922755B (zh) | 2021-04-06 |
WO2015004258A2 (en) | 2015-01-15 |
KR20160014023A (ko) | 2016-02-05 |
CN107922755A (zh) | 2018-04-17 |
EP3019561B1 (en) | 2018-11-21 |
US20150018479A1 (en) | 2015-01-15 |
CA2914795C (en) | 2019-02-19 |
US10179865B2 (en) | 2019-01-15 |
WO2015004258A3 (en) | 2015-04-02 |
CA2914795A1 (en) | 2015-01-15 |
EP3019561A2 (en) | 2016-05-18 |
MX2016000092A (es) | 2016-03-01 |
ES2711370T3 (es) | 2019-05-03 |
KR101838869B1 (ko) | 2018-03-16 |
JP6193489B2 (ja) | 2017-09-06 |
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