JP2009513790A - ジメルカプタン末端ポリチオエーテルポリマー、ならびにその合成方法および使用方法 - Google Patents
ジメルカプタン末端ポリチオエーテルポリマー、ならびにその合成方法および使用方法 Download PDFInfo
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- JP2009513790A JP2009513790A JP2008537931A JP2008537931A JP2009513790A JP 2009513790 A JP2009513790 A JP 2009513790A JP 2008537931 A JP2008537931 A JP 2008537931A JP 2008537931 A JP2008537931 A JP 2008537931A JP 2009513790 A JP2009513790 A JP 2009513790A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 40
- 229920006295 polythiol Polymers 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 title claims description 3
- 238000003786 synthesis reaction Methods 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 claims description 46
- 239000000565 sealant Substances 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 150000001993 dienes Chemical group 0.000 claims description 13
- 150000005671 trienes Chemical group 0.000 claims description 10
- 229920001021 polysulfide Polymers 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- 238000007789 sealing Methods 0.000 claims description 7
- 239000005077 polysulfide Substances 0.000 claims description 6
- 150000008117 polysulfides Polymers 0.000 claims description 6
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical group C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 claims description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
- 229920002959 polymer blend Polymers 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 13
- 239000011593 sulfur Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000000446 fuel Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000002318 adhesion promoter Substances 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- -1 aromatic dienes Chemical class 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229920001079 Thiokol (polymer) Polymers 0.000 description 2
- 239000011825 aerospace material Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- LHJQIRIGXXHNLA-UHFFFAOYSA-N calcium peroxide Chemical compound [Ca+2].[O-][O-] LHJQIRIGXXHNLA-UHFFFAOYSA-N 0.000 description 2
- 235000019402 calcium peroxide Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000002828 fuel tank Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- 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
- COXCGWKSEPPDAA-UHFFFAOYSA-N 2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)C#N COXCGWKSEPPDAA-UHFFFAOYSA-N 0.000 description 1
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 description 1
- 239000004343 Calcium peroxide Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229920000271 Kevlar® Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- MOWJPXLTZMVEHR-UHFFFAOYSA-N SC(OO)(CCCCC)S Chemical compound SC(OO)(CCCCC)S MOWJPXLTZMVEHR-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012812 sealant material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940105296 zinc peroxide Drugs 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/12—Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/04—Polysulfides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- C09J181/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- C09J181/04—Polysulfides
Abstract
Description
メカニカルスターラー、温度計および2つのガス吹き込み管(1つは窒素の入口用、およびもう1つは排出口用)を取り付けた1Lの4口丸底フラスコに、1,8−ジメルカプト−3,6−ジオキサオクタン(616.95g,3.38モル CAS #14970−87−7)を充填した。フラスコに乾燥した窒素を流し込み、内容物を32℃に加熱した。
表1に記載の構成要素を、ダブルシャフトカウル型(double shaft cowles type)バッチミキサー内で、水銀柱27インチまたはそれより大きい減圧度で、均一になるまで混合し、クラスBの密閉剤を調製した。構成要素AおよびBを
100:12の重量比で混合し、最終生成物である密閉剤を調製した。
2米国特許第4,623,711号に従って調製された(分子量約2500)。
3THIOKOL LP−55 ポリスルフィドポリマー、Toray Fine Chemicalsより市販されている。
4米国特許第6,172,179号に従って調製された(分子量約3000)。
5ORGASOL、Atofinaより市販されている。
6EXPANCEL、Akzoより市販されている。
7OSiより市販されている。
8OSiより市販されている。
10アルカリ金属アルミノ−シリケート 3Å粉末、UOPより市販されている。
11Akrochem Accelerator DPTT Powder、Akrochem Corp.より市販されている。
Claims (18)
- 請求項1に記載のポリマーであって、XがOであり;aが2であり;bが2であり;cが2であり;nが1であり、ならびにR2がビニルシクロヘキセン残基である、ポリマー。
- 請求項1に記載のポリマーを含有する、組成物。
- 請求項2に記載のポリマーを含有する、組成物。
- 請求項1に記載のポリマーおよび硬化剤を含有する、密閉剤。
- 請求項2に記載のポリマーおよび硬化剤を含有する、密閉剤。
- 前記硬化剤がMnO2である、請求項5に記載の密閉剤。
- 前記硬化剤がMnO2である、請求項6に記載の密閉剤。
- 粘性が10〜20,000ポイズである、請求項5に記載の密閉剤。
- 粘性が10〜20,000ポイズである、請求項6に記載の密閉剤。
- 請求項9に記載の方法であって、XがOであり;a、bおよびcが2であり;nが1であり、ならびに前記ジエンがビニルシクロヘキセンである、方法。
- 開口部をシールする方法であって、請求項5に記載の密閉剤を該開口部と関係した表面へ塗布する工程を含有する、方法。
- 開口部をシールする方法であって、請求項6に記載の密閉剤を該開口部と関係した表面へ塗布する工程を含有する、方法。
- 請求項3に記載の組成物であって、さらにポリスルフィドとポリチオエーテルを含有するポリマー混合物を含有する、組成物。
- 請求項4に記載の組成物であって、さらにポリスルフィドとポリチオエーテルを含有するポリマー混合物を含有する、組成物。
- 請求項13に記載の方法であって、前記表面が航空機または航空宇宙機の表面である、方法。
- 請求項14に記載の方法であって、前記表面が航空機または航空宇宙機の表面である、方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/260,553 US20070096396A1 (en) | 2005-10-27 | 2005-10-27 | Dimercaptan terminated polythioether polymers and methods for making and using the same |
US11/260,553 | 2005-10-27 | ||
PCT/US2006/041723 WO2007050725A1 (en) | 2005-10-27 | 2006-10-26 | Dimercaptan terminated polythioether polymers and methods for making and using the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009513790A true JP2009513790A (ja) | 2009-04-02 |
JP4937267B2 JP4937267B2 (ja) | 2012-05-23 |
Family
ID=37834204
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008537931A Active JP4937267B2 (ja) | 2005-10-27 | 2006-10-26 | ジメルカプタン末端ポリチオエーテルポリマー、ならびにその合成方法および使用方法 |
Country Status (15)
Country | Link |
---|---|
US (3) | US20070096396A1 (ja) |
EP (1) | EP1940918B1 (ja) |
JP (1) | JP4937267B2 (ja) |
KR (1) | KR100996757B1 (ja) |
CN (2) | CN102585501B (ja) |
AT (1) | ATE497984T1 (ja) |
AU (1) | AU2006306139B2 (ja) |
BR (1) | BRPI0619332B8 (ja) |
CA (1) | CA2627040C (ja) |
DE (1) | DE602006020056D1 (ja) |
DK (1) | DK1940918T3 (ja) |
ES (1) | ES2358278T3 (ja) |
HK (2) | HK1122583A1 (ja) |
RU (1) | RU2391357C2 (ja) |
WO (1) | WO2007050725A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012532955A (ja) * | 2009-07-09 | 2012-12-20 | 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 | 1成分の水分硬化性シーラントおよびその作製方法 |
JP2019530784A (ja) * | 2016-10-06 | 2019-10-24 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性組成物及び関連方法 |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070096396A1 (en) * | 2005-10-27 | 2007-05-03 | Sawant Suresh G | Dimercaptan terminated polythioether polymers and methods for making and using the same |
US20110319559A1 (en) * | 2010-06-25 | 2011-12-29 | PRC-DeSolo International, Inc. | Polythioether polymers, methods for preparation thereof, and compositions comprising them |
US8541513B2 (en) * | 2011-03-18 | 2013-09-24 | Prc-Desoto International, Inc. | Terminal-modified difunctional sulfur-containing polymers, compositions thereof and methods of use |
US8729216B2 (en) | 2011-03-18 | 2014-05-20 | Prc Desoto International, Inc. | Multifunctional sulfur-containing polymers, compositions thereof and methods of use |
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JP2012532955A (ja) * | 2009-07-09 | 2012-12-20 | 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 | 1成分の水分硬化性シーラントおよびその作製方法 |
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CA2627040C (en) | 2011-04-05 |
HK1122583A1 (en) | 2009-05-22 |
US20100036063A1 (en) | 2010-02-11 |
US20110060091A1 (en) | 2011-03-10 |
DE602006020056D1 (de) | 2011-03-24 |
CN101296968B (zh) | 2012-04-25 |
US20070096396A1 (en) | 2007-05-03 |
US7858704B2 (en) | 2010-12-28 |
ATE497984T1 (de) | 2011-02-15 |
CN102585501A (zh) | 2012-07-18 |
WO2007050725A1 (en) | 2007-05-03 |
EP1940918B1 (en) | 2011-02-09 |
RU2391357C2 (ru) | 2010-06-10 |
BRPI0619332A2 (pt) | 2011-09-27 |
BRPI0619332B1 (pt) | 2017-12-19 |
EP1940918A1 (en) | 2008-07-09 |
KR100996757B1 (ko) | 2010-11-25 |
BRPI0619332B8 (pt) | 2018-02-27 |
ES2358278T3 (es) | 2011-05-09 |
DK1940918T3 (da) | 2011-05-16 |
US8076420B2 (en) | 2011-12-13 |
HK1173169A1 (en) | 2013-05-10 |
RU2008121225A (ru) | 2009-12-10 |
AU2006306139B2 (en) | 2010-07-01 |
KR20080046748A (ko) | 2008-05-27 |
JP4937267B2 (ja) | 2012-05-23 |
AU2006306139A1 (en) | 2007-05-03 |
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CN102585501B (zh) | 2014-07-30 |
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