JP6182852B2 - プライマー組成物の製造方法及びプライマー組成物 - Google Patents
プライマー組成物の製造方法及びプライマー組成物 Download PDFInfo
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- JP6182852B2 JP6182852B2 JP2012258467A JP2012258467A JP6182852B2 JP 6182852 B2 JP6182852 B2 JP 6182852B2 JP 2012258467 A JP2012258467 A JP 2012258467A JP 2012258467 A JP2012258467 A JP 2012258467A JP 6182852 B2 JP6182852 B2 JP 6182852B2
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- Prior art keywords
- diisocyanate compound
- group
- primer composition
- mass
- diisocyanate
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 89
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- -1 diisocyanate compound Chemical class 0.000 claims description 123
- 239000003566 sealing material Substances 0.000 claims description 61
- 239000003054 catalyst Substances 0.000 claims description 53
- 239000005056 polyisocyanate Substances 0.000 claims description 53
- 229920001228 polyisocyanate Polymers 0.000 claims description 53
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 43
- 229920000642 polymer Polymers 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 33
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 18
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- 239000010703 silicon Substances 0.000 claims description 14
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 229920000620 organic polymer Polymers 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 6
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- 239000007795 chemical reaction product Substances 0.000 claims description 4
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- 150000001412 amines Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
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- 239000000975 dye Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
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- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
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- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
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- 229920001577 copolymer Polymers 0.000 description 3
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
- 238000004070 electrodeposition Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
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- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
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- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- QIJRBQDGQLSRLG-UHFFFAOYSA-N magnesium;pentane-2,4-dione Chemical compound [Mg].CC(=O)CC(C)=O QIJRBQDGQLSRLG-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- SQZZGEUJERGRIN-UHFFFAOYSA-N manganese;pentane-2,4-dione Chemical compound [Mn].CC(=O)CC(C)=O SQZZGEUJERGRIN-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- DLHSYEIDHYUMMQ-UHFFFAOYSA-N n-[3-[diethoxy(methyl)silyl]propyl]-4-methylpentan-2-imine Chemical compound CCO[Si](C)(OCC)CCCN=C(C)CC(C)C DLHSYEIDHYUMMQ-UHFFFAOYSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FLESAADTDNKLFJ-UHFFFAOYSA-N nickel;pentane-2,4-dione Chemical compound [Ni].CC(=O)CC(C)=O FLESAADTDNKLFJ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004762 orthosilicates Chemical class 0.000 description 1
- WATYAKBWIQTPDE-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O WATYAKBWIQTPDE-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000004587 polysulfide sealant Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000004588 polyurethane sealant Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000013615 primer Substances 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- ACECBHHKGNTVPB-UHFFFAOYSA-N silylformic acid Chemical class OC([SiH3])=O ACECBHHKGNTVPB-UHFFFAOYSA-N 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- GPMKKHIGAJLBMZ-UHFFFAOYSA-J titanium(4+);tetraacetate Chemical compound [Ti+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O GPMKKHIGAJLBMZ-UHFFFAOYSA-J 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LSZKGNJKKQYFLR-UHFFFAOYSA-J tri(butanoyloxy)stannyl butanoate Chemical compound [Sn+4].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O LSZKGNJKKQYFLR-UHFFFAOYSA-J 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Landscapes
- Paints Or Removers (AREA)
Description
(1) 溶剤(A)と、
塩素化重合体(B)と、
ジイソシアネート化合物(C)と、
ポリイソシアネート化合物(D)と、
メルカプト基を有するシランカップリング剤(E)と、
触媒(F)と、
を含み、
前記溶剤(A)と前記塩素化重合体(B)と前記ジイソシアネート化合物(C)と前記メルカプト基を有するシランカップリング剤(E)と前記触媒(F)とを混合した後、前記ポリイソシアネート化合物(D)を混合して得られることを特徴とするプライマー組成物。
(2) 溶剤(A)と、
塩素化重合体(B)と、
ジイソシアネート化合物(C)と、
ポリイソシアネート化合物(D)と、
メルカプト基を有するシランカップリング剤(E)と、
触媒(F)と、
を含み、
前記ジイソシアネート化合物(C)が芳香族系ジイソシアネート化合物であることを特徴とするプライマー組成物。
(3) 前記触媒(F)が錫系触媒である上記(1)または(2)に記載のプライマー組成物。
(4) 2成分形変成シリコーン系シーリング材用に用いられる上記(1)から(3)の何れか1つに記載のプライマー組成物。
(5) シーリング材とシーリング材との打ち継ぎ用に用いられる上記(1)から(4)の何れか1つに記載のプライマー組成物。
(6) 前記シーリング材が、加水分解性ケイ素含有基を有する有機重合体を含む上記(4)または(5)に記載のプライマー組成物。
(1) 溶剤(A)と塩素化重合体(B)とジイソシアネート化合物(C)とメルカプト基を有するシランカップリング剤(E)と前記ジイソシアネート化合物(C)100質量部に対して1.0質量部以上5.0質量部以下の触媒(F)とを混合して反応させる第1工程と、前記第1工程後にポリイソシアネート化合物(D)を混合する第2工程とを含むことを特徴とするプライマー組成物の製造方法。
(2) 溶剤(A)と、
塩素化重合体(B)と、
ジイソシアネート化合物(C)と、
ポリイソシアネート化合物(D)と、
メルカプト基を有するシランカップリング剤(E)と、
前記ジイソシアネート化合物(C)100質量部に対して1.0質量部以上5.0質量部以下の触媒(F)と、
を含み、
前記ジイソシアネート化合物(C)が芳香族系ジイソシアネート化合物であることを特徴とするプライマー組成物。
(3) 前記触媒(F)が錫系触媒である上記(2)に記載のプライマー組成物。
(4) 2成分形変成シリコーン系シーリング材に用いられる上記(2)または(3)に記載のプライマー組成物。
(5) シーリング材とシーリング材との打ち継ぎ用に用いられる上記(2)から(4)の何れか1つに記載のプライマー組成物。
(6) 前記シーリング材が、加水分解性ケイ素含有基を有する有機重合体を含む上記(4)または(5)に記載のプライマー組成物。
(7) 溶剤(A)と塩素化重合体(B)とジイソシアネート化合物(C)とメルカプト基を有するシランカップリング剤(E)と前記ジイソシアネート化合物(C)100質量部に対して1.0質量部以上5.0質量部以下の触媒(F)とが混合されて反応し、前記ジイソシアネート化合物(C)中の未反応のイソシアネート基が前記反応前に対して低減された反応物と、
ポリイソシアネート化合物(D)とを含むことを特徴とするプライマー組成物。
本実施形態の組成物に含まれる溶剤(A)は、塩素化重合体(B)と、ジイソシアネート化合物(C)と、ポリイソシアネート化合物(D)と、メルカプト基を有するシランカップリング剤(E)および触媒(F)に対して不活性であれば従来公知の各種の溶剤を用いることができる。溶剤(A)としては、特に制限はなく、有機溶剤、水溶性溶媒等、広く公知のものを使用することができる。溶剤(A)としては、具体的には、例えば、ベンゼン、トルエン、キシレン、ヘキサン、ヘプタン、オクタン、シクロヘキサン等の炭化水素系;テトラクロロメタン、メチレンクロリド等のハロゲン化炭化水素系;アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系;ジエチルエーテル、テトラヒドロフラン、ジオキサン等のエーテル系;酢酸メチル、酢酸エチル、酢酸ブチル等のエステル系;セロソルブアセテート、ブチルセロソルブアセテート等のエーテルエステル系;メタノール、エタノール、プロパノール、i−プロパノール、n−ブタノール等のアルコール系;ミネラルスピリッツ等のガソリンから灯油留分に至る石油系;その他に、N−メチル−2−ピロリドン、N,N−ジメチルホルムアミド、ジメチルアセトアミド等が挙げられる。これらの溶剤は、1種単独でも2種以上を併用して使用してもよい。
本実施形態の組成物に含まれる塩素化重合体(B)は、塩素化された重合体であれば特に限定されないが、好ましくは、例えば、イソプレン系合成ゴムの塩素化物、塩素化ポリエチレン、塩素化ポリプロピレン、塩素化ポリエチレン・プロピレン共重合体、塩素化ポリブタジエン、塩素化ポリスチレン、塩素化ポリブタジエン・スチレン共重合体、クロロスルフォン化ポリエチレン、クロロスルフォン化ポリエチレン・酢酸ビニル共重合体等から好適に選択される。また、塩素化重合体(B)は、上記例示した塩素化重合体を2種以上併用してもよい。
本実施形態の組成物に含まれるジイソシアネート化合物(C)は、分子内にイソシアネート基(NCO基)を2個有するものであれば特に限定されない。ジイソシアネート化合物(C)としては、具体的には、例えば、パラフェニレンジイソシアネート、トリレンジイソシアネート(TDI)、ナフタレンジイソシアネート(NDI)、4、4’ージフェニルメタンジイソシアネート(4,4’−MDI)、2,4’−ジフェニルメタンジイソシアネート(2,4’−MDI)、トリジンジイソシアネート(TODI)等の芳香族イソシアネート;テトラメチレンジイソシアネート、ヘキサメチレンジイソシアネート(HDI)、トリメチルヘキサメチレンジイソシアネート(TMHDI)、リジンジイソシアネート、ノルボルナンジイソシアネート(NBDI)、オクタデシルジイソシアネート等の脂肪族イソシアネート;トランスシクロヘキサン−1,4−ジイソシアネート、イソホロンジイソシアネート(IPDI)、ジシクロヘキシルメタンジイソシアネート(H12MDI)等の脂環式イソシアネート;キシレンジイソシアネート(XDI)、テトラメチルキシリレンジイソシアネート(TMXDI)等のアリール脂肪族イソシアネート;上記各イソシアネートの変性イソシアネート等が挙げられる。これらは、それぞれ1種単独でまたは2種以上を組み合わせて使用することができる。
本実施形態の組成物に含まれるポリイソシアネート化合物(D)は、分子内にイソシアネート基を2個以上有するものであれば特に限定されない。分子内にイソシアネート基を2個有するポリイソシアネート化合物(D)としては、上記のジイソシアネート化合物(C)と同様のものを用いることができる。上記のジイソシアネート化合物(C)以外のポリイソシアネート化合物(D)としては、例えば、ポリメチレンポリフェニレンポリイソシアネート、トリフェニルメタントリイソシアネート等のような芳香族ポリイソシアネート;ヘキサメチレンジイソシアネート(HDI)、トリメチルヘキサメチレンジイソシアネート(TMHDI)、リジンジイソシアネート、ノルボルナンジイソシアネート(NBDI)等のような脂肪族ポリイソシアネート;ビス(イソシアネートメチル)シクロヘキサン(H6XDI)等のような脂環式ポリイソシアネート;上記のジイソシアネート化合物(C)及び上記のポリイソシアネート化合物(D)のカルボジイミド変性ポリイソシアネート;上記のジイソシアネート化合物(C)及び上記のポリイソシアネート化合物(D)のイソシアヌレート変性ポリイソシアネート等が挙げられる。このようなポリイソシアネート化合物は、それぞれ1種単独でまたは2種以上を組み合わせて使用することができる。
本実施形態の組成物に含まれるシランカップリング剤(E)は、分子内にメルカプト基を有するシランカップリング剤であれば特に限定されない。シランカップリング剤(E)としては、接着発現を促進させるという観点から分子内にメルカプト基を有するものが好ましい。
本実施形態の組成物は、触媒(F)を含有することにより接着発現が速くなりシーリング材の打ち継ぎ面に対しても十分な接着性が得られる。本実施形態の組成物では、触媒(F)を塩素化重合体(B)の硬化剤として用いることができる。本実施形態の組成物に含有される触媒(F)としては、硬化性樹脂と反応可能なものであれば特に制限されない。
表1に示す各成分のうち、溶剤(A)と塩素化重合体(B)とジイソシアネート化合物(C)とメルカプト基を有するシランカップリング剤(E)と触媒(F)とを、同表に示す配合量(質量部)で配合しこれらを均一に混合(約5時間)した後、ポリイソシアネート化合物(D)を、同表に示す配合量(質量部)で配合し、さらに均一に混合(約1時間)して表1に示される実施例1〜8の各プライマー組成物を調製した。各々の実施例における各成分の配合量を表1に示す。
表1に示す各成分を、同表に示す配合量(質量部)で配合しこれらを均一に混合(約1時間)して表1に示される実施例9〜12、比較例1〜4の各プライマー組成物を調製した。各々の実施例、比較例における各成分の配合量を表1に示す。
図1は、剥離試験の様子を示す斜視図である。メラミン樹脂コートの超耐候性アクリル電着塗装板(アルミニウム板)11に変成シリコーン系のシーリング材12(商品名:スーパーII、横浜ゴム株式会社製)を塗布し、20℃で15時間養生して硬化させた後、カッターにてシーリング材12の表面を削り取った。その後、上記で得られた各プライマー組成物13を削り取ったシーリング材12の表面に塗布し、20℃で2分間放置した後、変成シリコーン系のシーリング材14(商品名:スーパーII、横浜ゴム株式会社製)を塗布し、以下に示す硬化・養生条件で硬化させて試験体とした。
(硬化・養生条件)
・接着性:20℃で15時間養生、及び20℃で30時間養生
(評価基準)
○:プライマーとシーリング材との接着界面が硬化している
×:プライマーとシーリング材との接着界面が未硬化である
・溶剤(A):酢酸エチル、関東化学株式会社製
・塩素化重合体(B):商品名「ペルグートS170」、住化バイエルウレタン株式会社製
・ジイソシアネート化合物(C1):芳香族イソシアネート、ジフェニルメタンジイソシアネート(MDI)、商品名「スミジュール44S」、住友バイエルジャパン株式会社製
・ジイソシアネート化合物(C2):芳香族イソシアネート、トリレンジイソシアネート(TDI)、商品名「TDI80」、三井化学株式会社製
・ジイソシアネート化合物(C3):脂肪族イソシアネート、キシレンジイソシアネート(XDI)、商品名「タケネート500」、三井化学ポリウレタン株式会社製
・ジイソシアネート化合物(C4):脂肪族イソシアネート、ヘキサメチレンジイソシアネート(HDI)、商品名「デュラネート50M」、旭化成ケミカルズ株式会社製
・ポリイソシアネート化合物(D):TDI−TMP付加体、商品名「スミジュールL−75」、NCO基含有率13.0質量%、固形分65%、住化バイエルウレタン株式会社製
・メルカプト基を有するシランカップリング剤(E):γ−メルカプトプロピルトリメトキシシラン、商品名「KBM−803」、信越化学工業株式会社製
・触媒(F):DINP変性錫系触媒、商品名「MSCAT−02」、日本化学産業株式会社製
12 シーリング材
13 プライマー組成物
14 シーリング材
Claims (7)
- 溶剤(A)と塩素化重合体(B)とジイソシアネート化合物(C)とメルカプト基を有するシランカップリング剤(E)と前記ジイソシアネート化合物(C)100質量部に対して1.0質量部以上5.0質量部以下の触媒(F)とを混合して反応させる第1工程と、前記第1工程後にポリイソシアネート化合物(D)を混合する第2工程とを含むことを特徴とするプライマー組成物の製造方法。
- 溶剤(A)と、
塩素化重合体(B)と、
ジイソシアネート化合物(C)と、
ポリイソシアネート化合物(D)と、
メルカプト基を有するシランカップリング剤(E)と、
前記ジイソシアネート化合物(C)100質量部に対して1.0質量部以上5.0質量部以下の触媒(F)と、
を含み、
前記ジイソシアネート化合物(C)が芳香族系ジイソシアネート化合物であることを特徴とするプライマー組成物。 - 前記触媒(F)が錫系触媒である請求項2に記載のプライマー組成物。
- 2成分形変成シリコーン系シーリング材に用いられる請求項2または3に記載のプライマー組成物。
- シーリング材とシーリング材との打ち継ぎ用に用いられる請求項2から4の何れか1項に記載のプライマー組成物。
- 前記シーリング材が、加水分解性ケイ素含有基を有する有機重合体を含む請求項4または5に記載のプライマー組成物。
- 溶剤(A)と塩素化重合体(B)とジイソシアネート化合物(C)とメルカプト基を有するシランカップリング剤(E)と前記ジイソシアネート化合物(C)100質量部に対して1.0質量部以上5.0質量部以下の触媒(F)とが混合されて反応し、前記ジイソシアネート化合物(C)中の未反応のイソシアネート基が前記反応前に対して低減された反応物と、
ポリイソシアネート化合物(D)とを含むことを特徴とするプライマー組成物。
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