JP2017537885A - フェニルヒドラジン/無水物付加物およびこれらを使用する嫌気性硬化性組成物 - Google Patents
フェニルヒドラジン/無水物付加物およびこれらを使用する嫌気性硬化性組成物 Download PDFInfo
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- JP2017537885A JP2017537885A JP2017522118A JP2017522118A JP2017537885A JP 2017537885 A JP2017537885 A JP 2017537885A JP 2017522118 A JP2017522118 A JP 2017522118A JP 2017522118 A JP2017522118 A JP 2017522118A JP 2017537885 A JP2017537885 A JP 2017537885A
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- acrylate
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- 239000000203 mixture Substances 0.000 title claims abstract description 122
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 title abstract description 10
- 229940067157 phenylhydrazine Drugs 0.000 title abstract description 10
- 150000008064 anhydrides Chemical class 0.000 title abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 230000001939 inductive effect Effects 0.000 claims description 11
- -1 hydroxypropyl Chemical group 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- RSUCJIJELNXPQI-UHFFFAOYSA-N [4-[[4-(2-methylprop-2-enoyloxy)phenyl]methyl]phenyl] 2-methylprop-2-enoate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1CC1=CC=C(OC(=O)C(C)=C)C=C1 RSUCJIJELNXPQI-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000013466 adhesive and sealant Substances 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 description 26
- 239000000853 adhesive Substances 0.000 description 22
- 230000001070 adhesive effect Effects 0.000 description 22
- 229910000831 Steel Inorganic materials 0.000 description 16
- 239000010959 steel Substances 0.000 description 16
- RGMMTOZHCJCZRW-UHFFFAOYSA-N 2,4,6-trihydroxyphenylhexan-1-one Chemical compound CCCCCC(=O)C1=C(O)C=C(O)C=C1O RGMMTOZHCJCZRW-UHFFFAOYSA-N 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 11
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 10
- 229940081974 saccharin Drugs 0.000 description 9
- 235000019204 saccharin Nutrition 0.000 description 9
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 9
- 150000002431 hydrogen Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 4
- 0 CC(C)(C(*)(*)C(NNc1ccccc1)=*)C(O)=O Chemical compound CC(C)(C(*)(*)C(NNc1ccccc1)=*)C(O)=O 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000002738 chelating agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 150000004031 phenylhydrazines Chemical class 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 3
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 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
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- 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 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 229910001369 Brass Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
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- 239000002253 acid Substances 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
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- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- JUDOLRSMWHVKGX-UHFFFAOYSA-N 1,1-dioxo-1$l^{6},2-benzodithiol-3-one Chemical compound C1=CC=C2C(=O)SS(=O)(=O)C2=C1 JUDOLRSMWHVKGX-UHFFFAOYSA-N 0.000 description 1
- NCYNKWQXFADUOZ-UHFFFAOYSA-N 1,1-dioxo-2,1$l^{6}-benzoxathiol-3-one Chemical compound C1=CC=C2C(=O)OS(=O)(=O)C2=C1 NCYNKWQXFADUOZ-UHFFFAOYSA-N 0.000 description 1
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- MWOODERJGVWYJE-UHFFFAOYSA-N 1-methyl-1-phenylhydrazine Chemical compound CN(N)C1=CC=CC=C1 MWOODERJGVWYJE-UHFFFAOYSA-N 0.000 description 1
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- RTMKOJVCQFWHFA-UHFFFAOYSA-N 2-(anilinocarbamoyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)C(=O)NNC1=CC=CC=C1 RTMKOJVCQFWHFA-UHFFFAOYSA-N 0.000 description 1
- HGIPIEYZJPULIQ-UHFFFAOYSA-N 2-(methylazaniumyl)-2-phenylacetate Chemical compound CNC(C(O)=O)C1=CC=CC=C1 HGIPIEYZJPULIQ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- WFXFDWVEXFKVHF-UHFFFAOYSA-N 4-(n-(methylideneamino)anilino)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)N(N=C)C1=CC=CC=C1 WFXFDWVEXFKVHF-UHFFFAOYSA-N 0.000 description 1
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- ILBKZWDNZQWQGY-UHFFFAOYSA-N 4-(n-aminoanilino)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)N(N)C1=CC=CC=C1 ILBKZWDNZQWQGY-UHFFFAOYSA-N 0.000 description 1
- GDZIMHQTKFQCFV-UHFFFAOYSA-N 4-[n-(methylamino)anilino]-4-oxobut-2-enoic acid Chemical compound OC(=O)C=CC(=O)N(NC)C1=CC=CC=C1 GDZIMHQTKFQCFV-UHFFFAOYSA-N 0.000 description 1
- PRIFQAHGLOJLKQ-UHFFFAOYSA-N 4H-trithiolo[4,5-c]pyrazole Chemical compound C1=NNC2=C1SSS2 PRIFQAHGLOJLKQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
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- YNDXITUSQAMBKZ-UHFFFAOYSA-N C(C1C(C(=O)O)CCC=C1)(=O)O.C1(=CC=CC=C1)NN Chemical compound C(C1C(C(=O)O)CCC=C1)(=O)O.C1(=CC=CC=C1)NN YNDXITUSQAMBKZ-UHFFFAOYSA-N 0.000 description 1
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- 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
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
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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 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
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- 230000002028 premature Effects 0.000 description 1
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- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
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- 125000006413 ring segment Chemical group 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
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Abstract
Description
によって包含され、その例は、3−カルボキシアクリロイルフェニルヒドラジン、メチル−3−カルボキシアクリロイルフェニルヒドラジン、3−カルボキシプロパノイルフェニルヒドラジンおよびメチレン−3−カルボキシプロパノイルフェニルヒドラジンである。
の嫌気性硬化促進化合物(その例は、フェニルグリシンおよびN−メチルフェニルグリシンである)をベースにした嫌気性硬化性組成物を提供している。
(式中、Yは、C1〜6アルキルもしくはアルコキシ、またはハロ基によって最大5つの位置において場合によって置換されている芳香環であり、Aは、C=O、S=OまたはO=S=Oであり、Xは、NH、OまたはSであり、Zは、C1〜6アルキルもしくはアルコキシ、またはハロ基によって最大5つの位置において場合によって置換されている芳香環であり、あるいはYおよびZは、一緒になって同じ芳香環または芳香環系に結合することができ、但しXがNHである場合、o−安息香酸スルフィミドは該構造から除外される。)
上記の構造によって包含される嫌気性硬化促進化合物の例には、2−スルホ安息香酸環状無水物および3H−1,2−ベンゾジチオール−3−オン−1,1−ジオキシドが含まれる。
Xは、H、C1〜20アルキル、C2〜20アルケニル、またはC7〜20アルカリールであり、後者の3つのいずれかは、1以上のヘテロ原子で遮断されていてもよいか、−OH、−NH2または−SHから選択される1つ以上の基によって官能化されているか、またはXとYは一緒になって5〜7個の環原子を有する炭素環を形成してもよい。;Zは、O、SまたはNX’であり、ここでX’は、H、C1〜20アルキル、C2〜20アルケニルまたはC7〜20アルカリールであり、後者の3つのうちのいずれかが1以上のヘテロ原子によって遮断されていてもよいか、−OH、−NH2または−SHから選択される1つ以上の基によって官能化されてもよい。;Rは、任意であるが、存在する場合、芳香族環上に3回まで存在することができ、存在する場合、C1〜20アルキル、C2〜20アルケニル、またはC7〜20アルカリールであり、後者の3つのいずれかは、1以上のヘテロ原子で遮断されていてもよいか、−OH、−NH2または−SHから選択される1つ以上の基によって官能化されてもよい。;nは、0および1であり、zは1〜3であり、但し、XがHである場合、zは2ではなく、好ましくは1である。より具体的には、THQベースまたはインドリンベースの付加物が包含され得る。(米国特許第8,481,659号参照)。
R1は、HまたはC1〜4アルキルから選択され;pは、1〜5の整数であり;Oは、1個以上のC1〜4アルキル置換基を有するか、または有さない、シクロアルキル、シクロアルケニル、ビシクロアルキルまたはビシクロアルケニルを表す。
本発明は、同じ分子上に結合−C(=O)−NH−NH−およびカルボン酸官能基を有する嫌気性硬化促進剤を提供する。このような硬化促進剤化合物を従来の硬化促進剤のいくらかまたはすべての代替として嫌気性硬化性組成物へ添加することによって、驚くべきことに形成された反応生成物へ、少なくとも同程度の硬化速度および物理的特性を提供する。
式中
R1は、HまたはC1〜4アルキルから選択され;pは、1〜5の整数であり;Oは、1個以上のC1〜4アルキル置換基を有するか、または有さない、シクロアルキル、シクロアルケニル、ビシクロアルキルまたはビシクロアルケニルを表す。
式中、
R4は、水素、ハロゲンまたは1〜約4個の炭素原子を有するアルキルから選択される基であり;qは、少なくとも1、好ましくは、1〜約4に等しい整数であり;Xは、少なくとも2個の炭素原子を含み、総結合容量がq+1である有機基である。X中の炭素原子の数の上限に関し、本質的にいかなる値でも機能できるモノマーが存在する。しかし、実際、一般的な上限値は、約50個の炭素原子、望ましくは30個、最も望ましくは約20個である。
Y1およびY2の各々は、少なくとも2個の炭素原子、望ましくは2個〜約10個の炭素原子を含む有機基(例えば、炭化水素基)であり、Zは、有機基、好ましくは少なくとも1個の炭素原子、好ましくは2〜約10個の炭素原子を含む炭化水素基である。
mは、少なくとも1に等しい整数、例えば1〜約15またはそれ以上、望ましくは、1〜約8であり;nは、少なくとも1に等しい整数、例えば1〜約40以上、望ましくは、約2〜約10であり;pは、0または1である。
R9は、水素または1〜7個の炭素原子を有する低級アルキルから選択され;R7は、水素、ハロゲン(例えば塩素)またはアルキル(例えばメチルおよびエチル基)から選択され、R8は、1〜8個の炭素原子を有する低級アルキレン、フェニレンおよびナフチレンから選択される二価の有機基である。
<HHPH>
上記と同じ手順をTHPA(76.8g、0.505mol)に使用した。粗収率= 85.8(66%)。融点=149℃。生成物をCH3CNからから再結晶した。結晶化収量=53.9g(41%):1H NMR(d6−DMSO)δδ12.1(br s,1,OH),9.5(s,1,NH),7.7(s,1,NH),7.1(m,2,Ar−H),6.7(m,3,Ar−H),5.6(m,2,HC=CH),2.9(m,2,CO−CH),2.1−2.6(m,4,=C−CH2−);13C NMR(d6−DMSO)175,173,150,128,126,125,118,38,27,26,22;IR (純粋)3276,1704,1633,1601,1494,1258,1211,921,749,690cm−1。
THPHおよびHHPHは、APH/マレイン酸およびコハク酸フェニルヒドラジン(「SPH」)をコントロールとして用いて、脱脂された軟鋼製ナットおよびボルト、ステンレス鋼製ナットおよびボルト、および軟鋼製ピンおよびカラー上の2つのモデル嫌気性接着剤組成物中の嫌気性接着硬化剤として評価した。
これらの新しい硬化システムを、従来の硬化成分、APH/MAおよびサッカリンを含有する対照配合物と、ナット/ボルトおよびピン/カラー試験片について82℃の加速安定性および15分/1時間/24時間の接着試験を比較した。
配合物の82℃の安定性は、接着剤配合物が82℃で3.5時間以上液体である続ける場合に、配合物が許容可能な保存安定性を有すると判断される評価に従って決定された。以下の表Bから分かるように、各配合物は24時間以上液体のままであった。
破断/プリベール接着試験のために、試験片を、組み立て後、周囲温度で15分、1時間および24時間硬化させ、以下のように試験した。
表7および図7は、SPH含有組成物と比較して、本発明の組成物は、室温で鋼製ナットおよびボルト上で15分硬化させたときの強度発現の改善を示す。表9および図9は、SPH含有組成物と比較して、本発明の組成物は、鋼製のナットおよびボルト上で室温で1時間硬化したときの強度発現の改善を示す。
Claims (13)
- (a)(メタ)アクリレート成分、(b)嫌気性硬化誘発性組成物および(c)請求項1に記載の化合物を含む嫌気性硬化性組成物。
- (メタ)アクリレート成分は、H2C=CGCO2R10
(式中、Gは、H、ハロゲンおよび1〜約4個の炭素原子を有するアルキルからなる群から選択されるメンバーであり、R10は、1〜約16個の炭素原子を有するアルキル、シクロアルキル、アルケニル、シクロアルケニル、アルカリールおよびアリール基からなる群から選択されるメンバーであり、シラン、ケイ素、酸素、ハロゲン、カルボニル、ヒドロキシル、エステル、カルボン酸、尿素、ウレタン、カルバメート、アミン、アミド、硫黄、スルホネートおよびスルホンからなる群から選択されるメンバーで置換または遮断されているまたはされていない)によって表される、請求項2に記載の組成物。 - (メタ)アクリレート成分は、シリコーン(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、テトラヒドロフラン(メタ)アクリレートおよびジ(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、ヘキサンジオールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、テトラエチレンジグリコールジ(メタ)アクリレート、ジグリセロールテトラ(メタ)アクリレート、テトラメチレンジ(メタ)アクリレート、エチレンジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、ビスフェノール−A−(メタ)アクリレート、エトキシ化ビスフェノール−A−(メタ)アクリレート、ビスフェノール−F−(メタ)アクリレート、エトキシ化ビスフェノール−F−(メタ)アクリレート、およびビスフェノール−A−ジ(メタ)アクリレート、エトキシ化ビスフェノール−A−ジ(メタ)アクリレート、ビスフェノール−F−ジ(メタ)アクリレートおよびエトキシ化ビスフェノール−F−ジメタクリレートからなる群から選択されるメンバーである、請求項2に記載の組成物。
- 共促進剤をさらに含む、請求項1に記載の組成物。
- 請求項2に記載の組成物の反応生成物。
- 嫌気性硬化性組成物から反応生成物を調製する方法であって、請求項2に記載の嫌気性硬化性組成物を所望の基材表面に塗布するステップと、組成物を硬化させるのに十分な時間、組成物を嫌気性環境に暴露することを含む方法。
- 嫌気性硬化促進剤として請求項1に記載の化合物とメタ)アクリレート成分と嫌気性硬化誘発性組成物を一緒に混合するステップを含む嫌気性硬化性組成物を調製する方法。
- 嫌気性硬化誘発性組成物が、フリーラジカル開始剤とフリーラジカル共促進剤との組み合わせを含む、請求項2に記載の組成物。
- 嫌気硬化促進剤としての化合物の使用方法であって、(I)化合物を(メタ)アクリレート成分、嫌気性硬化誘発性組成物と混合するか、または(II)基材表面に化合物を塗布してその上に塗布することを含む方法。
- アクリル酸をさらに含む、請求項1に記載の組成物。
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