JP4633053B2 - エポキシキャップ化ポリチオエーテル - Google Patents
エポキシキャップ化ポリチオエーテル Download PDFInfo
- Publication number
- JP4633053B2 JP4633053B2 JP2006518645A JP2006518645A JP4633053B2 JP 4633053 B2 JP4633053 B2 JP 4633053B2 JP 2006518645 A JP2006518645 A JP 2006518645A JP 2006518645 A JP2006518645 A JP 2006518645A JP 4633053 B2 JP4633053 B2 JP 4633053B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy
- group
- capped polythioether
- compound
- capped
- 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.)
- Expired - Lifetime
Links
- 229920006295 polythiol Polymers 0.000 title claims abstract description 59
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000004593 Epoxy Substances 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 10
- -1 alkyl peroxides Chemical class 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 9
- 239000011953 free-radical catalyst Substances 0.000 claims description 8
- 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 description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000007514 bases Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- MOWJPXLTZMVEHR-UHFFFAOYSA-N SC(OO)(CCCCC)S Chemical compound SC(OO)(CCCCC)S MOWJPXLTZMVEHR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 42
- 239000003795 chemical substances by application Substances 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 15
- 150000004662 dithiols Chemical class 0.000 description 14
- 239000000178 monomer Substances 0.000 description 13
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 9
- 229920001289 polyvinyl ether Polymers 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 8
- 229960000834 vinyl ether Drugs 0.000 description 8
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000005077 polysulfide Substances 0.000 description 5
- 229920001021 polysulfide Polymers 0.000 description 5
- 150000008117 polysulfides Polymers 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- QEBJRRFIWCWPMA-UHFFFAOYSA-N diethyl-bis(sulfanyl)-$l^{4}-sulfane Chemical compound CCS(S)(S)CC QEBJRRFIWCWPMA-UHFFFAOYSA-N 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000000034 method Methods 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
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920002266 Pluriol® Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N cyclohexene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006395 saturated elastomer Chemical class 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 description 1
- XMEPRJBZFCWFKN-UHFFFAOYSA-N 1,3-Butanedithiol Chemical compound CC(S)CCS XMEPRJBZFCWFKN-UHFFFAOYSA-N 0.000 description 1
- XDWRKTULOHXYGN-UHFFFAOYSA-N 1,3-bis(ethenoxy)-2,2-bis(ethenoxymethyl)propane Chemical compound C=COCC(COC=C)(COC=C)COC=C XDWRKTULOHXYGN-UHFFFAOYSA-N 0.000 description 1
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 1
- UEIPWOFSKAZYJO-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-[2-(2-ethenoxyethoxy)ethoxy]ethane Chemical compound C=COCCOCCOCCOCCOC=C UEIPWOFSKAZYJO-UHFFFAOYSA-N 0.000 description 1
- WIERREHJAVDNEX-UHFFFAOYSA-N 1-chloro-n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NC(Cl)NC1=CC=CC=C1 WIERREHJAVDNEX-UHFFFAOYSA-N 0.000 description 1
- CZAVRNDQSIORTH-UHFFFAOYSA-N 1-ethenoxy-2,2-bis(ethenoxymethyl)butane Chemical compound C=COCC(CC)(COC=C)COC=C CZAVRNDQSIORTH-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- PIBIAJQNHWMGTD-UHFFFAOYSA-N 1-n,3-n-bis(4-methylphenyl)benzene-1,3-diamine Chemical compound C1=CC(C)=CC=C1NC1=CC=CC(NC=2C=CC(C)=CC=2)=C1 PIBIAJQNHWMGTD-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- MUUOUUYKIVSIAR-UHFFFAOYSA-N 2-but-3-enyloxirane Chemical compound C=CCCC1CO1 MUUOUUYKIVSIAR-UHFFFAOYSA-N 0.000 description 1
- UKTHULMXFLCNAV-UHFFFAOYSA-N 2-hex-5-enyloxirane Chemical compound C=CCCCCC1CO1 UKTHULMXFLCNAV-UHFFFAOYSA-N 0.000 description 1
- FCZHJHKCOZGQJZ-UHFFFAOYSA-N 2-oct-7-enyloxirane Chemical compound C=CCCCCCCC1CO1 FCZHJHKCOZGQJZ-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- OEBNAGGBGILICS-UHFFFAOYSA-N 3h-dithiole-3-thiol Chemical compound SC1SSC=C1 OEBNAGGBGILICS-UHFFFAOYSA-N 0.000 description 1
- KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920010299 Orgasol® 1002 D NAT 1 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- SMTOKHQOVJRXLK-UHFFFAOYSA-N butane-1,4-dithiol Chemical compound SCCCCS SMTOKHQOVJRXLK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical class 0.000 description 1
- QVTZUVMKKRFSCC-UHFFFAOYSA-N cyclohexanamine;methane Chemical compound C.NC1CCCCC1.NC1CCCCC1 QVTZUVMKKRFSCC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- KMTUBAIXCBHPIZ-UHFFFAOYSA-N pentane-1,5-dithiol Chemical compound SCCCCCS KMTUBAIXCBHPIZ-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/302—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Epoxy Compounds (AREA)
- Sealing Material Composition (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、一般に、エポキシキャップ化ポリチオエーテルおよびエポキシキャップ化ポリチオエーテルの硬化可能組成物に関する。
航空および航空宇宙用途で使用されるシーラント、コーティングおよび接着剤は、可撓性、耐燃料油性および耐熱性を示すことが望ましい。一般に、これらの特性は、高分子樹脂の骨格にポリエーテル結合を組み込むことにより、達成され得る。
航空および宇宙航空用途に公知のエポキシドの限界に取り組むために、エポキシキャップ化ポリチオエーテルおよびエポキシキャップ化ポリチオエーテルの硬化可能組成物が提供されている。
R1は、C2〜6n−アルキレン、C3〜6分枝アルキレン、C6〜8シクロアルキレン、C6〜10アルキルシクロアルキレンおよび−[−(CHR3)p−X−]q−(CHR3)r−からなる群から選択され、
ここで、
各R3は、別個に、HおよびCH3から選択される;
各Xは、別個に、O、S、−NH−および−NR4−から選択される;
R4は、Hおよび−CH3から選択される;
pは、2〜6の整数である;
qは、1〜5の整数である;そして
rは、2〜10の整数である;そして
各R2は、二価連結基である。
特に明記しない限り、本明細書および請求の範囲で使用される成分の量、反応条件などを示す全ての数値は、いずれの場合にも、「約」との用語により修飾されることが理解できるはずである。従って、以下の明細書および添付の請求の範囲で述べた数値パラメータは、他にそうでないことが示されていない限り、近似値であり、これは、本発明で得られる所望の特性に依存して、変わり得る。少なくとも、この請求の範囲への均等論の適用を限定しようとするのではなく、各数値パラメータは、少なくとも、報告された有効数字の数に照らして、通常の端数計算技術を適用することにより、解釈すべきである。
R1は、C2〜6n−アルキレン、C3〜6分枝アルキレン、C6〜8シクロアルキレン、C6〜10アルキルシクロアルキレン、−[−(CHR3)p−X−]q−(CHR3)r−からなる群から選択され、
ここで、
各R3は、別個に、Hおよび−CH3から選択される;
各Xは、別個に、O、S、−NH−および−NR4−から選択される;
R4は、Hおよび−CH3から選択される;
pは、2〜6の整数である;
qは、1〜5の整数である;そして
rは、2〜10の整数である;そして
各R2は、二価連結基(典型的には、3個〜20個の炭素原子を含有するアルキレンまたはオキシアルキレン)である。
耐薬品性は、ASTM D 1308、24 Hour Spot Testに従って、決定した。
1リットルの四ッ口フラスコに、窒素雰囲気下にて、ジメルカプトジオキサオクタン(DMDO)253.4g(1.39モル)を加えた。撹拌しながら、このフラスコの内容物を50℃まで加熱し、そして1時間にわたって、ジエチレングリコールジビニルエーテル(DEG−DVE)146.6g(0.93モル)を加えた。その反応混合物の温度を70℃まで上げ、そしてフリーラジカル開始剤であるVazo(登録商標)67(2,2’−アゾビス(2−メチルブチロニトリル)、Du Pont)0.05gを加えた。この反応混合物の温度を、70℃で、さらに1時間維持した。DEG−DVEとDMDOとの反応の完結は、420のメルカプタン当量値により、明らかとなった。70℃で、1時間にわたって、アリルグリシジルエーテル(AGE)(110.87g、0.97モル、化学量論量より2%過剰)を加え、その反応混合物を、70℃で、さらに1時間加熱した。次いで、70℃で、3時間間隔で、10個の部分のVazo(登録商標)67(各0.165g)を加えた。Vazo(登録商標)67を加えたのに続いて、この反応混合物を、70℃で、5時間加熱した。次いで、この反応混合物を、70℃/4〜5mmHgで、3時間脱気して、液状エポキシキャップ化ポリチオエーテル(これは、かすかな黄色、5.0ポアズの粘度および563のエポキシ当量を有している)を得た。その反応収量は、508.7g(100%)であった。
250mLの三ッ口フラスコに、窒素雰囲気下にて、DMDO(62.17g(モル))を加えた。撹拌しながら、DMDOを60℃まで加熱し、その反応物の温度を60℃〜70℃で維持しつつ、その反応混合物に、50分間にわたって、DEG−DVE(44.88g(モル))を加えた。この反応混合物を、70℃で、さらに4時間加熱した。この反応混合物に、1.5時間間隔で、2個の部分のVazo(登録商標)67(各0.036g)を加え、70℃で、1.5時間加熱した。この反応混合物のメルカプタン当量値は、890であった。追加部分のVazo(登録商標)67(0.036g)を加え、その反応混合物をさらに1.5時間加熱した。893のメルカプタン当量値により、DEG−DVEとDMDOとの反応が完結したことが明らかとなった。70°で、AGE(13.21g、0.116モル、化学量論量より2%過剰)を一度に加え、この反応混合物を2時間加熱した。70℃で、3時間間隔で、8個の部分のVazo(登録商標)67(各0.035g)を加え、そして加熱をさらに4時間継続した。この段階で、この反応混合物のメルカプタン当量値は、28,642であった。この反応を完結するために、AGE(4.8g、0.042モル、化学量論量より38%過剰)を追加し、その反応混合物を、70℃で、1時間加熱した。3時間間隔で、2個の部分のVazo(登録商標)67(各0.036g)を加えた。Vazo(登録商標)67を加えたのに続いて、この反応混合物を、70℃で、5時間加熱した。次いで、この反応混合物を、70℃/4〜5mmHgで、2時間脱気して、僅かに濁った液状エポキシキャップ化ポリチオエーテル(これは、かすかな黄色、26ポアズの粘度および1,217のエポキシ当量値を有している)を得た。その反応収量は、120.0g(100%)であった。
Claims (10)
- エポキシキャップ化ポリチオエーテルであって、該エポキシキャップ化ポリチオエーテルは、
式IIの構造を有する化合物であって:
式IVの構造を有する化合物であって:
pは、2〜6の範囲の別個に選択された整数であり、
qは、1〜5の範囲の別個に選択された整数であり、そして
rは、2〜10の範囲の別個に選択された整数であり、
R3は、水素またはメチルであり、
Xは、別個に、O、S、−NH−および−NR4−から選択され、
ここで、R4は、Hおよび−CH3から選択され、そして
mは、1〜10の有理数である、化合物
との反応によって形成される生成物を、
式IIIの構造を有する化合物であって:
エポキシキャップ化ポリチオエーテル。 - 式IIの構造を有する化合物が、ジメルカプトジオキサオクタンである、請求項1に記載のエポキシキャップ化ポリチオエーテル。
- 式IIIの構造を有する化合物が、アリルグリシジルエーテルである、請求項1に記載のエポキシキャップ化ポリチオエーテル。
- 加水分解性塩素を含まない、請求項1に記載のエポキシキャップ化ポリチオエーテル。
- 300未満のエポキシ当量重量範囲を有する、請求項1に記載のエポキシキャップ化ポリチオエーテル。
- 150未満のエポキシ当量重量範囲を有する、請求項1に記載のエポキシキャップ化ポリチオエーテル。
- フリーラジカル触媒、イオン触媒および紫外線からなる群から選択される触媒の存在下にて形成される、請求項1に記載のエポキシキャップ化ポリチオエーテル。
- 前記触媒が、酸性または塩基性化合物を含まず、そして分解しても酸性または塩基性化合物を生成しない、請求項7に記載のエポキシキャップ化ポリチオエーテル。
- 前記触媒が、フリーラジカル触媒を含む、請求項7に記載のエポキシキャップ化ポリチオエーテル。
- 前記フリーラジカル触媒が、アゾ型触媒および過酸化アルキルからなる群から選択される、請求項9に記載のエポキシキャップ化ポリチオエーテル。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/617,582 US20050010003A1 (en) | 2003-07-11 | 2003-07-11 | Epoxy-capped polythioethers |
PCT/US2004/018926 WO2005014564A1 (en) | 2003-07-11 | 2004-07-09 | Epoxy-capped polythioethers |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009201129A Division JP2009280617A (ja) | 2003-07-11 | 2009-08-31 | エポキシキャップ化ポリチオエーテル |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007520439A JP2007520439A (ja) | 2007-07-26 |
JP4633053B2 true JP4633053B2 (ja) | 2011-02-16 |
Family
ID=33565004
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006518645A Expired - Lifetime JP4633053B2 (ja) | 2003-07-11 | 2004-07-09 | エポキシキャップ化ポリチオエーテル |
JP2009201129A Withdrawn JP2009280617A (ja) | 2003-07-11 | 2009-08-31 | エポキシキャップ化ポリチオエーテル |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009201129A Withdrawn JP2009280617A (ja) | 2003-07-11 | 2009-08-31 | エポキシキャップ化ポリチオエーテル |
Country Status (16)
Country | Link |
---|---|
US (2) | US20050010003A1 (ja) |
EP (1) | EP1644348B1 (ja) |
JP (2) | JP4633053B2 (ja) |
KR (1) | KR100741201B1 (ja) |
CN (1) | CN100408568C (ja) |
AT (1) | ATE365727T1 (ja) |
AU (1) | AU2004262642B2 (ja) |
BR (1) | BRPI0412385B1 (ja) |
CA (1) | CA2531794C (ja) |
DE (1) | DE602004007272T2 (ja) |
DK (1) | DK1644348T3 (ja) |
ES (1) | ES2288264T3 (ja) |
IL (1) | IL172949A (ja) |
MX (1) | MXPA06000349A (ja) |
RU (1) | RU2342372C2 (ja) |
WO (1) | WO2005014564A1 (ja) |
Families Citing this family (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7622548B2 (en) * | 2003-07-11 | 2009-11-24 | Prc Desoto International, Inc. | Epoxy- or amine/hydroxy-capped polythioethers |
US20050010003A1 (en) * | 2003-07-11 | 2005-01-13 | Prc-Desoto International, Inc. | Epoxy-capped polythioethers |
US8003748B2 (en) | 2004-02-17 | 2011-08-23 | Chevron Phillips Chemical Company, Lp | Polythiourethane compositions and processes for making and using same |
DE602005024664D1 (de) | 2004-02-17 | 2010-12-23 | Chevron Phillips Chemical Co | Schwefelhaltige zusammensetzungen und verfahren zu deren herstellung |
US7498384B2 (en) * | 2005-02-04 | 2009-03-03 | Ppg Industries Ohio, Inc. | Multi-component epoxy-amine primer systems comprising a polythioether |
EA200800597A1 (ru) * | 2005-08-16 | 2008-08-29 | Шеврон Филлипс Кемикал Компани Лп | Композиции отвержденного меркаптаном эпоксидного полимера и способы производства и применения таких композиций |
EP1940917A2 (en) | 2005-08-16 | 2008-07-09 | Chevron Phillips Chemical Company LP | Polymer compositions and processes for making and using same |
US20070096396A1 (en) * | 2005-10-27 | 2007-05-03 | Sawant Suresh G | Dimercaptan terminated polythioether polymers and methods for making and using the same |
US8623989B1 (en) * | 2006-05-05 | 2014-01-07 | PRC De Soto International, Inc. | Polyurea/polythiourea coatings |
CN102030902B (zh) * | 2006-05-05 | 2014-06-11 | Ppg工业俄亥俄公司 | 由硫醚官能的低聚多硫醇制备的组合物和制品 |
US7569163B2 (en) * | 2007-03-16 | 2009-08-04 | Prc Desoto International, Inc. | Polythioether amine resins and compositions comprising same |
US7879955B2 (en) | 2007-05-01 | 2011-02-01 | Rao Chandra B | Compositions including a polythioether |
US7875666B2 (en) * | 2008-04-24 | 2011-01-25 | Prc-De Soto International, Inc. | Thioethers, methods for their preparation, and compositions including such thioethers |
US8466220B2 (en) * | 2008-04-24 | 2013-06-18 | PRC DeSoto International, Inc | Thioethers, methods for their preparation, and compositions including such thioethers |
US9080004B2 (en) * | 2010-10-07 | 2015-07-14 | Prc-Desoto International, Inc. | Diethylene glycol monomethyl ether resistant coating |
US8816044B2 (en) | 2011-09-21 | 2014-08-26 | PRC DeSoto International, Inc | Flexible polyamines, flexible amine-terminated adducts, compositions thereof and methods of use |
US9018322B2 (en) | 2012-06-21 | 2015-04-28 | FRC-DeSoto International, Inc. | Controlled release amine-catalyzed, Michael addition-curable sulfur-containing polymer compositions |
US9056949B2 (en) | 2013-06-21 | 2015-06-16 | Prc-Desoto International, Inc. | Michael addition curing chemistries for sulfur-containing polymer compositions employing bis(sulfonyl)alkanols |
US8952124B2 (en) | 2013-06-21 | 2015-02-10 | Prc-Desoto International, Inc. | Bis(sulfonyl)alkanol-containing polythioethers, methods of synthesis, and compositions thereof |
US8871896B2 (en) | 2012-06-21 | 2014-10-28 | Prc Desoto International, Inc. | Michael addition curing chemistries for sulfur-containing polymer compositions |
US9303149B2 (en) | 2012-06-21 | 2016-04-05 | Prc-Desoto International, Inc. | Adhesion promoting adducts containing metal ligands, compositions thereof, and uses thereof |
US8513339B1 (en) * | 2012-06-21 | 2013-08-20 | Prc-Desoto International, Inc. | Copolymerizable sulfur-containing adhesion promoters and compositions thereof |
US8710159B2 (en) | 2012-06-21 | 2014-04-29 | Prc Desoto International, Inc. | Polyfunctional sulfur-containing epoxies and compositions thereof |
US9006360B2 (en) | 2012-10-24 | 2015-04-14 | Prc-Desoto International, Inc. | Controlled-release amine-catalyzed, sulfur-containing polymer and epdxy compositions |
CA2889344C (en) * | 2012-10-24 | 2018-06-12 | Prc-Desoto International, Inc. | Uses of uv-curable polythioether sealants for sealing fasteners and for smoothing surfaces |
US9062162B2 (en) | 2013-03-15 | 2015-06-23 | Prc-Desoto International, Inc. | Metal ligand-containing prepolymers, methods of synthesis, and compositions thereof |
US9062139B2 (en) | 2013-03-15 | 2015-06-23 | Prc-Desoto International, Inc. | Sulfone-containing polythioethers, compositions thereof, and methods of synthesis |
US9650552B2 (en) | 2013-03-15 | 2017-05-16 | Prc-Desoto International, Inc. | Energy curable sealants |
CN104558584B (zh) * | 2013-10-18 | 2017-02-01 | 锦西化工研究院有限公司 | 一种环氧端基聚硫代醚液体橡胶的合成方法 |
WO2015066135A2 (en) | 2013-10-29 | 2015-05-07 | Prc-Desoto International, Inc. | Metal ligand-containing prepolymers, methods of synthesis, and compositions thereof |
US9611359B2 (en) | 2013-10-29 | 2017-04-04 | Prc-Desoto International, Inc. | Maleimide-terminated sulfur-containing polymers, compositions thereof, and uses thereof |
JP6606495B2 (ja) | 2013-10-29 | 2019-11-13 | ピーアールシー−デソト インターナショナル,インコーポレイティド | 金属リガンドを含有する接着促進性付加体、その組成物、及びその使用 |
US9328275B2 (en) | 2014-03-07 | 2016-05-03 | Prc Desoto International, Inc. | Phosphine-catalyzed, michael addition-curable sulfur-containing polymer compositions |
US9328274B2 (en) | 2014-03-07 | 2016-05-03 | Prc-Desoto International, Inc. | Michael acceptor-terminated urethane-containing fuel resistant prepolymers and compositions thereof |
US9518197B2 (en) | 2014-03-07 | 2016-12-13 | Prc-Desoto International, Inc. | Cure-on-demand moisture-curable urethane-containing fuel resistant prepolymers and compositions thereof |
US9382448B2 (en) * | 2014-08-29 | 2016-07-05 | Prc-Desoto International, Inc. | Polythioether sealants with enhanced thermal resistance |
CN104262624B (zh) * | 2014-09-03 | 2017-05-17 | 浙江大学 | 一种多环氧基聚合物的合成方法 |
CN104448314B (zh) * | 2014-12-08 | 2017-07-25 | 郑州中原思蓝德高科股份有限公司 | 一种环氧基封端的聚硫聚合物、其制备方法及用途、包含其的室温快固型环氧树脂胶粘剂 |
US9422451B2 (en) | 2015-01-09 | 2016-08-23 | Prc-Desoto International, Inc. | Low density fuel resistant sulfur-containing polymer compositions and uses thereof |
CN105837820B (zh) * | 2015-01-16 | 2018-07-03 | 中国科学院宁波材料技术与工程研究所 | 一种潜伏型聚硫醚基聚硫醇、其合成方法与应用 |
KR20170116114A (ko) | 2015-02-13 | 2017-10-18 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 내한성 실란트 및 그의 성분 |
US9951252B2 (en) | 2015-08-10 | 2018-04-24 | Prc-Desoto International, Inc. | Moisture-curable fuel-resistant sealant systems |
US9777139B2 (en) | 2015-10-26 | 2017-10-03 | Prc-Desoto International, Inc. | Reactive antioxidants, antioxidant-containing prepolymers, and compositions thereof |
US10053606B2 (en) | 2015-10-26 | 2018-08-21 | Prc-Desoto International, Inc. | Non-chromate corrosion inhibiting polythioether sealants |
US9902799B2 (en) | 2015-11-11 | 2018-02-27 | Prc-Desoto International, Inc. | Urethane-modified prepolymers containing pendent alkyl groups, compositions and uses thereof |
US9988487B2 (en) | 2015-12-10 | 2018-06-05 | Prc-Desoto International, Inc. | Blocked 1,8-diazabicyclo[5.4.0]undec-7-ene bicarbonate catalyst for aerospace sealants |
US10035926B2 (en) | 2016-04-22 | 2018-07-31 | PRC—DeSoto International, Inc. | Ionic liquid catalysts in sulfur-containing polymer compositions |
US10370561B2 (en) | 2016-06-28 | 2019-08-06 | Prc-Desoto International, Inc. | Urethane/urea-containing bis(alkenyl) ethers, prepolymers prepared using urethane/urea-containing bis(alkenyl) ethers, and uses thereof |
CN107312174B (zh) * | 2017-07-19 | 2019-10-18 | 北京化工大学 | 一种聚硫醚的合成方法 |
US10351674B2 (en) | 2017-10-17 | 2019-07-16 | Prc-Desoto International, Inc. | Sulfur-containing polymeric particles and compositions |
US20210246266A1 (en) * | 2018-06-08 | 2021-08-12 | The Regents Of The University Of Colorado, A Body Corporate | High dynamic range two-stage photopolymers |
US11098222B2 (en) | 2018-07-03 | 2021-08-24 | Prc-Desoto International, Inc. | Sprayable polythioether coatings and sealants |
EP3628505A1 (en) | 2018-09-25 | 2020-04-01 | Sihl GmbH | Inkjet printable film for packaging applications |
US10843180B2 (en) | 2018-10-02 | 2020-11-24 | Prc-Desoto International, Inc. | Delayed cure micro-encapsulated catalysts |
US11015097B2 (en) * | 2019-03-06 | 2021-05-25 | Prc-Desoto International, Inc. | Chemically resistant sealant compositions and uses thereof |
CN109970951B (zh) * | 2019-03-25 | 2021-09-17 | 烟台大学 | 一种多环氧基环氧树脂的合成方法 |
CN109929091A (zh) * | 2019-03-25 | 2019-06-25 | 烟台大学 | 一种柔性环氧树脂及其合成方法 |
EP3738782A1 (en) | 2019-05-16 | 2020-11-18 | Sihl GmbH | Inkjet printed film for decorative applications |
US11437162B2 (en) | 2019-12-31 | 2022-09-06 | Industrial Technology Research Institute | Conductive material composition and conductive material prepared therefrom |
CN113913150B (zh) * | 2021-11-18 | 2023-03-14 | 中国航发北京航空材料研究院 | 用于飞机钣金件的贴合面密封剂 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3454539A (en) * | 1967-08-11 | 1969-07-08 | Ciba Ltd | Polyepoxides |
NL7000025A (ja) * | 1969-01-08 | 1970-07-10 | ||
US4046729A (en) * | 1975-06-02 | 1977-09-06 | Ppg Industries, Inc. | Water-reduced urethane coating compositions |
US4366307A (en) * | 1980-12-04 | 1982-12-28 | Products Research & Chemical Corp. | Liquid polythioethers |
US4374945A (en) * | 1981-03-11 | 1983-02-22 | Witco Chemical Corporation | Thioglycolate and thiopropionate secondary stabilizers |
US4609762A (en) * | 1984-01-30 | 1986-09-02 | Products Research & Chemical Corp. | Thioethers having a high sulfur content and method therefor |
EP0166695B1 (de) * | 1984-06-29 | 1989-10-18 | Ciba-Geigy Ag | Verfahren zur Herstellung von Glycidythioethern |
US4681811A (en) * | 1985-08-19 | 1987-07-21 | Ppg Industries, Inc. | Color plus clear coatings employing polyepoxides and polyacid curing agents in the clear coat |
EP0237489B1 (de) * | 1986-03-13 | 1989-11-29 | Ciba-Geigy Ag | Umsetzungsprodukte von Bis-glycidylthioethern |
JPH02111950A (ja) * | 1988-10-21 | 1990-04-24 | Hitachi Chem Co Ltd | 感光性樹脂組成物および感光性エレメント |
JPH02175749A (ja) * | 1988-12-28 | 1990-07-09 | Nippon Steel Chem Co Ltd | 封止用樹脂組成物 |
SU1743160A1 (ru) * | 1990-09-04 | 1998-02-20 | Институт физико-органической химии и углехимии АН УССР | 1,2-бис-(1-глицидилбензимидазол-2-илтио)этан в качестве соотвердителя эпоксидных смол и 1,2-бис-(бензимидазол-2-илтио)этан как промежуточный продукт в синтезе 1,2-бис-(1-глицидилбензимидазол-2-илтио)этана в качестве соотвердителя эпоксидных смол |
US5225472A (en) * | 1992-05-19 | 1993-07-06 | Courtaulds Aerospace, Inc. | Low viscosity polythiol and method therefor |
JP3403590B2 (ja) * | 1996-10-15 | 2003-05-06 | 三井化学株式会社 | 含硫エポキシ化合物及び含硫エポキシ樹脂 |
US6372849B2 (en) * | 1997-02-19 | 2002-04-16 | Prc-Desoto International, Inc. | Sealants and potting formulations including polymers produced by the reaction of a polythiol and polyvinyl ether monomer |
US5912319A (en) * | 1997-02-19 | 1999-06-15 | Courtaulds Aerospace, Inc. | Compositions and method for producing fuel resistant liquid polythioether polymers with good low temperature flexibility |
JP2000309584A (ja) * | 1999-02-24 | 2000-11-07 | Mitsubishi Gas Chem Co Inc | エピスルフィド化合物およびそれを用いた高屈折率樹脂の製造方法。 |
JP3405934B2 (ja) * | 1999-03-10 | 2003-05-12 | 三井化学株式会社 | 新規な光学用樹脂 |
JP3563006B2 (ja) * | 1999-12-10 | 2004-09-08 | 三井化学株式会社 | (チオ)エポキシ系重合性組成物 |
US6800371B2 (en) * | 2001-03-07 | 2004-10-05 | 3M Innovative Properties Company | Adhesives and adhesive compositions containing thioether groups |
US7097883B2 (en) * | 2003-06-05 | 2006-08-29 | Ppg Industries Ohio, Inc. | Low temperature liquid polythioether polymers |
US7622548B2 (en) * | 2003-07-11 | 2009-11-24 | Prc Desoto International, Inc. | Epoxy- or amine/hydroxy-capped polythioethers |
US20050010003A1 (en) * | 2003-07-11 | 2005-01-13 | Prc-Desoto International, Inc. | Epoxy-capped polythioethers |
-
2003
- 2003-07-11 US US10/617,582 patent/US20050010003A1/en not_active Abandoned
-
2004
- 2004-07-09 EP EP04755235A patent/EP1644348B1/en not_active Expired - Lifetime
- 2004-07-09 RU RU2006103988/04A patent/RU2342372C2/ru active
- 2004-07-09 JP JP2006518645A patent/JP4633053B2/ja not_active Expired - Lifetime
- 2004-07-09 BR BRPI0412385A patent/BRPI0412385B1/pt not_active IP Right Cessation
- 2004-07-09 DE DE602004007272T patent/DE602004007272T2/de not_active Expired - Lifetime
- 2004-07-09 ES ES04755235T patent/ES2288264T3/es not_active Expired - Lifetime
- 2004-07-09 MX MXPA06000349A patent/MXPA06000349A/es active IP Right Grant
- 2004-07-09 DK DK04755235T patent/DK1644348T3/da active
- 2004-07-09 CN CNB2004800199306A patent/CN100408568C/zh not_active Expired - Lifetime
- 2004-07-09 WO PCT/US2004/018926 patent/WO2005014564A1/en active IP Right Grant
- 2004-07-09 AU AU2004262642A patent/AU2004262642B2/en not_active Ceased
- 2004-07-09 CA CA2531794A patent/CA2531794C/en not_active Expired - Lifetime
- 2004-07-09 AT AT04755235T patent/ATE365727T1/de not_active IP Right Cessation
- 2004-07-09 KR KR1020067000648A patent/KR100741201B1/ko not_active IP Right Cessation
-
2006
- 2006-01-02 IL IL172949A patent/IL172949A/en active IP Right Grant
- 2006-03-07 US US11/369,490 patent/US7671145B2/en active Active
-
2009
- 2009-08-31 JP JP2009201129A patent/JP2009280617A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
ATE365727T1 (de) | 2007-07-15 |
EP1644348B1 (en) | 2007-06-27 |
RU2342372C2 (ru) | 2008-12-27 |
AU2004262642B2 (en) | 2007-07-26 |
JP2009280617A (ja) | 2009-12-03 |
WO2005014564A1 (en) | 2005-02-17 |
DE602004007272D1 (de) | 2007-08-09 |
US7671145B2 (en) | 2010-03-02 |
DK1644348T3 (da) | 2007-10-22 |
ES2288264T3 (es) | 2008-01-01 |
EP1644348A1 (en) | 2006-04-12 |
CA2531794A1 (en) | 2005-02-17 |
CN1823050A (zh) | 2006-08-23 |
AU2004262642A1 (en) | 2005-02-17 |
MXPA06000349A (es) | 2006-03-28 |
KR100741201B1 (ko) | 2007-07-19 |
JP2007520439A (ja) | 2007-07-26 |
US20050010003A1 (en) | 2005-01-13 |
IL172949A (en) | 2012-07-31 |
IL172949A0 (en) | 2006-06-11 |
KR20060040673A (ko) | 2006-05-10 |
RU2006103988A (ru) | 2006-06-27 |
BRPI0412385B1 (pt) | 2016-04-19 |
CA2531794C (en) | 2011-01-18 |
US20070299217A1 (en) | 2007-12-27 |
BRPI0412385A (pt) | 2006-09-19 |
DE602004007272T2 (de) | 2007-10-11 |
CN100408568C (zh) | 2008-08-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4633053B2 (ja) | エポキシキャップ化ポリチオエーテル | |
JP5194109B2 (ja) | ポリチオエーテルを含むシーラント組成物 | |
JP5107059B2 (ja) | 燃料耐性を示す組成物およびその組成物を製造する方法 | |
US20040247792A1 (en) | Low temperature liquid polythioether polymers | |
ES2362464T3 (es) | Composición selladora que comprende politioéter. |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090601 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090831 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090928 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20091215 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100114 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100212 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100309 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100608 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100629 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100928 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20101021 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20101116 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4633053 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131126 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |