JP5697977B2 - 耐熱性の嫌気的に硬化する組成物 - Google Patents
耐熱性の嫌気的に硬化する組成物 Download PDFInfo
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- JP5697977B2 JP5697977B2 JP2010516998A JP2010516998A JP5697977B2 JP 5697977 B2 JP5697977 B2 JP 5697977B2 JP 2010516998 A JP2010516998 A JP 2010516998A JP 2010516998 A JP2010516998 A JP 2010516998A JP 5697977 B2 JP5697977 B2 JP 5697977B2
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- 239000000203 mixture Substances 0.000 title claims description 83
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 30
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 21
- 229910052710 silicon Inorganic materials 0.000 claims description 21
- 239000010703 silicon Substances 0.000 claims description 21
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 17
- 229910052796 boron Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- -1 hydroxypropyl Chemical group 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 230000001939 inductive effect Effects 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 150000002825 nitriles Chemical group 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- PRIFQAHGLOJLKQ-UHFFFAOYSA-N 4H-trithiolo[4,5-c]pyrazole Chemical group C1=NNC2=C1SSS2 PRIFQAHGLOJLKQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 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
- 239000004202 carbamide Substances 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 2
- 229940081974 saccharin Drugs 0.000 claims description 2
- 235000019204 saccharin Nutrition 0.000 claims description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 150000004992 toluidines Chemical class 0.000 claims 1
- 239000000523 sample Substances 0.000 description 40
- 239000000853 adhesive Substances 0.000 description 21
- 230000001070 adhesive effect Effects 0.000 description 21
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 14
- 235000010338 boric acid Nutrition 0.000 description 13
- 238000001723 curing Methods 0.000 description 11
- 239000004327 boric acid Substances 0.000 description 10
- 230000014759 maintenance of location Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 230000000712 assembly Effects 0.000 description 4
- 238000000429 assembly Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 3
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-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
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-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
- 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
- 0 COC*c1cc(**OC)cc(*2O*2)c1 Chemical compound COC*c1cc(**OC)cc(*2O*2)c1 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- ISRJTGUYHVPAOR-UHFFFAOYSA-N dihydrodicyclopentadienyl acrylate Chemical compound C1CC2C3C(OC(=O)C=C)C=CC3C1C2 ISRJTGUYHVPAOR-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
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- 239000011347 resin Substances 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- MYOQALXKVOJACM-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy pentaneperoxoate Chemical compound CCCCC(=O)OOOC(C)(C)C MYOQALXKVOJACM-UHFFFAOYSA-N 0.000 description 1
- 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
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- UBRWPVTUQDJKCC-UHFFFAOYSA-N 1,3-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC(C(C)(C)OOC(C)(C)C)=C1 UBRWPVTUQDJKCC-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-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
- JFZBUNLOTDDXNY-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)propoxy]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)OCC(C)OC(=O)C(C)=C JFZBUNLOTDDXNY-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
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- ODMBLKQTVUQJFT-UHFFFAOYSA-N 3,7-dimethyloct-6-enyl 2-methylprop-2-enoate Chemical compound CC(C)=CCCC(C)CCOC(=O)C(C)=C ODMBLKQTVUQJFT-UHFFFAOYSA-N 0.000 description 1
- QPBVYDIIQIYFQO-UHFFFAOYSA-N 3,7-dimethyloct-6-enyl prop-2-enoate Chemical compound CC(C)=CCCC(C)CCOC(=O)C=C QPBVYDIIQIYFQO-UHFFFAOYSA-N 0.000 description 1
- SWDGWQVRDKNNBV-UHFFFAOYSA-N 3-[2-[[2-[bis(2,5-dioxopyrrol-3-yl)amino]phenyl]methyl]-n-(2,5-dioxopyrrol-3-yl)anilino]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(N(C=2C(NC(=O)C=2)=O)C=2C(=CC=CC=2)CC=2C(=CC=CC=2)N(C=2C(NC(=O)C=2)=O)C=2C(NC(=O)C=2)=O)=C1 SWDGWQVRDKNNBV-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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- 229930192627 Naphthoquinone Natural products 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 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 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
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Description
本発明は、高温条件に対して耐久性を示す嫌気的に硬化する組成物に関する。
嫌気性接着剤組成物は、一般的によく知られている。例えば、R.D.Richの「嫌気性接着剤(Anaerobic Adhesive)」[Handbook of Adhesive Technology,29,467−79,A.Pizzi and K.L.Mittal,eds.,Marcel Dekker,Inc.,New York(1994)]およびここに挙げられている参考文献を参照されたし。それら組成物は多く使用されており、新規用途の開発が続いている。
シクロヘキセニルメタノールメタクリレート;エポキシ化シクロヘキセニルメタノールメタクリレート;ジヒドロジシクロペンタジエニルアクリレート;エポキシ化ジヒドロジシクロペンタジエニルアクリレート;ジヒドロジシクロペンタジエニルメタクリレート;エポキシ化ジヒドロジシクロペンタジエニルメタクリレート;エポキシ化2−プロペノイック酸;2−[(3a,3,4,5,6,7,7a−ヘキサヒドロ−4,7−メタノ−1H−インデニル)オキシ]エチルエステル;エポキシ化2−プロペノイック酸;2−メチル−2−[(3a,3,4,5,6,7,7a−ヘキサヒドロ−4,7−メタノ−1H−インデニル)オキシ]エチルエステル;およびこれらの組合せを例とする、特定の構造の共反応物成分、ならびに(c)嫌気硬化を誘導する組成物のようなラジカル硬化を誘導する組成物、を含む。本発明では、組成物中に共反応物が存在することで改良された接着力および熱劣化に対する耐久性を有する、そのラジカル硬化反応生成物を提供する。また、この組成物は、耐熱性付与剤を含んでいてもよく、例えば、イミジゾール誘導体(例えば、ベンゾイルイミジゾール、メチルイミジゾール、ベンゾイルメチルイミジゾール、フタロイルジイミジゾールおよびこれらの組合せ)、潜在性イミジゾール、および活性水素を有する化合物を分子中の第3級アミノ基、エポキシ化合物およびカルボン酸無水物と共に反応させることによって得られる付加物から選択されるものである。
R、R1、R2およびR3は、同じであっても、または異なっていてもよく、上記の定義と同じもの、および1から約30個の炭素原子を有するシクロアルキル、シクロアルケニル、およびアリールであり、ヘテロ原子、およびヘテロ環構造で置換されていても、または割り込まれていてもよく、もしくは
統合されたR1およびR3は、結合して約20から約28個の環原子を有する環状構造を形成してもよく、R1およびR3は共に、ジアルキル置換ポリエーテル構造を表し、この構造はトリチアジアザペンタレン構造で置換されていても、または割り込まれていてもよく、これ自体は、上の定義と同様のA1、R2、またはR3で置換されていても、置換されていなくてもよい)。米国特許第6,583,289号(McArdle)公報を参照されたし。
最初に、相対的な高温強度値を決定するために、異なった濃度でホウ酸を使う場合およびホウ酸を使わない場合でLOCTITE272を評価した。
Claims (12)
- 嫌気硬化性組成物であって、
(a)(メタ)アクリレート成分、
(b)嫌気性硬化を誘導する組成物、および
(c)構造単位:MO−X(Y)−OM’を含む成分(式中、MおよびM’は、独立して、水素、ナトリウム、カリウム、およびリチウムからなる群より選択され、Xは、シリコンまたはボロンであり、Xがシリコンの場合、Yは=Oであり、Xがボロンの場合、YはOHであり、ただしYはOHで、Xがボロンの場合、前記(c)成分は、25重量%から75重量%の範囲内の量で存在し、あるいは、Yは=Oで、Xがシリコンの場合、前記(c)成分は、10重量%から75重量%の範囲内の量で存在するという条件においてである)を含む組成物。 - 前記嫌気性硬化を誘導する組成物が、フリーラジカル重合の開始剤を含む、請求項1に記載の組成物。
- 前記成分中のXがボロンであり、前記(c)成分は組成物中に35重量%から60重量%の範囲内の量で存在する、請求項1または2に記載の組成物。
- 前記成分中のXがボロンであり、前記(c)成分は組成物中に40重量%から50重量%の範囲内の量で存在する、請求項1〜3のいずれか1項に記載の組成物。
- 前記(メタ)アクリレート成分が、H2C=CGCO2R1(式中、Gは、H、ハロゲンおよび1から4個の炭素原子を有するアルキルからなる群より選択されるものであり、R1は、1から16個の炭素原子を有し、シラン、シリコン、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、スルホンからなる群より選択されるもので置換されているか、または置換されていないか、もしくは割り込まれているアルキル、シクロアルキル、アルケニル、シクロアルケニル、アルカリル、およびアリール基からなる群より選択されるものである)で表される、請求項1〜4のいずれか1項に記載の組成物。
- 前記(メタ)アクリレート成分が、シリコン(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、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、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、ならびにトリメチロールプロパントリ(メタ)アクリレートからなる群より選択される、請求項1〜5のいずれか1項に記載の組成物。
- 前記嫌気性硬化を誘導する組成物が、下記:
A.サッカリン、トルイジン、アセチルフェニルヒドラジン、マレイン酸、およびキノンの組合せ;
B.
C.
D.
E.下記の構造:
F.トリアジンおよびチオールの組合せ、
の1つ以上を含む、請求項1〜6のいずれか1項に記載の組成物。
- さらに、共反応物を含み、
前記共反応物が:
構造IIの式中、X1は、少なくとも1個は存在し、HまたはO=CDnAから選択され、少なくとも1個のX1は、O=CDnAであり、ここでDnおよびAは、上記の定義と同じものであり;
構造IVの式中、DおよびAは、上記と同じものであり、少なくとも1個は存在し、また、DおよびAは共に、互いにα−β関係にある環原子に結合して存在することができる]
からなる群より選択される、請求項1〜7のいずれか1項に記載の組成物。 - 請求項1〜9のいずれか1項に記載の組成物の反応生成物。
- 嫌気硬化性組成物から反応生成物を製造するための方法であって、以下のステップ、
請求項1〜9のいずれか1項に記載の嫌気硬化性組成物を、所望の基体表面に塗布するステップおよび
前記組成物を前記組成物が硬化するのに十分な時間、嫌気性環境に曝すステップ
を含む、方法。 - 2つの対になった基体の間で、請求項1〜9のいずれか1項に記載の組成物でもって形成された結合を含む、組成物。
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US11/778,190 US20090022894A1 (en) | 2007-07-16 | 2007-07-16 | Thermally Resistant Anaerobically Curable Compositions |
US11/778,190 | 2007-07-16 | ||
PCT/US2008/008582 WO2009011819A2 (en) | 2007-07-16 | 2008-07-14 | Thermally resistant anaerobically curable compositions |
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JPWO2012086445A1 (ja) * | 2010-12-24 | 2014-05-22 | スリーボンドファインケミカル株式会社 | 嫌気硬化性組成物 |
CN102604547A (zh) * | 2012-02-23 | 2012-07-25 | 北京天山新材料技术股份有限公司 | 一种耐高温厌氧锁固胶及其制备方法 |
JP2015525263A (ja) * | 2012-05-30 | 2015-09-03 | ヘンケル ユーエス アイピー エルエルシー | シール性能を改善する基材を被覆するための樹脂組成物 |
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Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3218305A (en) * | 1963-12-26 | 1965-11-16 | Loctite Corp | Accelerated anaerobic compositions and method of using same |
US3988299A (en) * | 1974-10-10 | 1976-10-26 | Loctite Corporation | Anaerobic adhesive composition having improved strength at elevated temperature consisting of unsaturated diacrylate monomer and maleimide additive |
US4287330A (en) * | 1975-05-23 | 1981-09-01 | Loctite Corporation | Accelerator for curable compositions |
US4321349A (en) * | 1975-05-23 | 1982-03-23 | Loctite Corporation | Accelerator for curable compositions |
IE43811B1 (en) * | 1976-11-08 | 1981-06-03 | Loctite Ltd | Curable acrylate ester compositions containing hydrazine acelerators and acid co-accelerators |
JPS5582157A (en) * | 1978-12-18 | 1980-06-20 | Asahi Chem Ind Co Ltd | Curable molding compound |
US4500608A (en) * | 1980-11-03 | 1985-02-19 | Minnesota Mining And Manufacturing Company | Anaerobically-curing compositions |
US4447588A (en) * | 1980-11-03 | 1984-05-08 | Minnesota Mining & Manufacturing Company | Anaerobically-curing compositions |
US4413108A (en) * | 1980-11-03 | 1983-11-01 | Minnesota Mining & Manufacturing Company | Anaerobically-curing compositions |
US4320221A (en) * | 1980-12-12 | 1982-03-16 | The Dow Chemical Company | Addition polymerizable isocyanate-polyol anaerobic adhesives |
US4528059A (en) * | 1981-08-03 | 1985-07-09 | Minnesota Mining & Manufacturing Company | Anaerobically-cuting compositions |
EP0081326B1 (en) * | 1981-12-09 | 1986-05-21 | Lingner + Fischer GmbH | Curing compositions |
US4451627A (en) * | 1982-09-07 | 1984-05-29 | The Dow Chemical Company | Addition polymerizable urethane-based anaerobic adhesives made from tin (II) organoesters |
JPS59207977A (ja) * | 1983-05-12 | 1984-11-26 | Okura Ind Co Ltd | 嫌気硬化性接着剤 |
JPS61185573A (ja) * | 1985-02-12 | 1986-08-19 | Chisso Corp | 硬化性組成物 |
JP2815233B2 (ja) | 1990-01-08 | 1998-10-27 | 大倉工業株式会社 | 嫌気性接着剤 |
JPH0853506A (ja) * | 1994-08-11 | 1996-02-27 | Okura Ind Co Ltd | 嫌気硬化性組成物の空気接触面の硬化方法 |
US5605999A (en) * | 1995-06-05 | 1997-02-25 | Loctite Corporation | Anaerobically curable silicones |
US5811473A (en) * | 1996-04-02 | 1998-09-22 | Loctite Corporation | Primer activator composition for anaerobic adhesives |
DE69841485D1 (de) * | 1997-07-03 | 2010-03-18 | Henkel Corp | Anaerobe klebstoffzusammensetzungen kontrollierter stärke für hohe temperaturen welche bei umgebungsbedingungen härtbar sind |
US6043327A (en) * | 1997-07-03 | 2000-03-28 | Loctite Corporation | Anaerobic adhesive compositions of acrylates coreactants and maleimides curable under ambient conditions |
US6150479A (en) * | 1998-11-23 | 2000-11-21 | Loctite Corporation | Radical-curable adhesive compositions, reaction products of which demonstrate superior resistance to thermal degradation |
US6342545B1 (en) * | 1998-11-23 | 2002-01-29 | Loctite Corporation | Radical-curable adhesive compositions, reaction products of which demonstrate superior resistance to thermal degradation |
AU1998100A (en) * | 1999-01-08 | 2000-07-24 | Loctite (R&D) Limited | Novel curative for anaerobic adhesive compositions |
AU5107300A (en) * | 1999-06-11 | 2001-01-02 | Three Bond Co. Ltd. | Anaerobically curable composition |
US6835762B1 (en) * | 2002-05-31 | 2004-12-28 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
US6958368B1 (en) * | 2002-05-31 | 2005-10-25 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
US6897277B1 (en) * | 2003-12-22 | 2005-05-24 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
US20060047046A1 (en) * | 2004-08-30 | 2006-03-02 | Illinois Tool Works, Inc. | Thixotropic anaerobic adhesive |
JP2006104312A (ja) * | 2004-10-05 | 2006-04-20 | Three Bond Co Ltd | プレコート型接着剤組成物 |
-
2007
- 2007-07-16 US US11/778,190 patent/US20090022894A1/en not_active Abandoned
-
2008
- 2008-07-14 CA CA2691947A patent/CA2691947C/en not_active Expired - Fee Related
- 2008-07-14 CN CN200880024813.7A patent/CN101743260B/zh active Active
- 2008-07-14 WO PCT/US2008/008582 patent/WO2009011819A2/en active Application Filing
- 2008-07-14 KR KR1020107003244A patent/KR101520513B1/ko active IP Right Grant
- 2008-07-14 JP JP2010516998A patent/JP5697977B2/ja active Active
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2016
- 2016-05-03 US US15/145,167 patent/US10100226B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
KR20100046009A (ko) | 2010-05-04 |
WO2009011819A3 (en) | 2009-03-05 |
WO2009011819A2 (en) | 2009-01-22 |
US10100226B2 (en) | 2018-10-16 |
CN101743260A (zh) | 2010-06-16 |
KR101520513B1 (ko) | 2015-05-21 |
JP2010533768A (ja) | 2010-10-28 |
US20090022894A1 (en) | 2009-01-22 |
CA2691947C (en) | 2016-05-24 |
CN101743260B (zh) | 2015-12-16 |
CA2691947A1 (en) | 2009-01-22 |
US20160319162A1 (en) | 2016-11-03 |
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