JP2006525390A - ポリスルフィドとポリエポキシドとからプレポリマーを製造する方法 - Google Patents
ポリスルフィドとポリエポキシドとからプレポリマーを製造する方法 Download PDFInfo
- Publication number
- JP2006525390A JP2006525390A JP2006505353A JP2006505353A JP2006525390A JP 2006525390 A JP2006525390 A JP 2006525390A JP 2006505353 A JP2006505353 A JP 2006505353A JP 2006505353 A JP2006505353 A JP 2006505353A JP 2006525390 A JP2006525390 A JP 2006525390A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- process according
- polysulfide
- polyepoxide
- carried out
- 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.)
- Pending
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 34
- 229920001021 polysulfide Polymers 0.000 title claims abstract description 31
- 239000005077 polysulfide Substances 0.000 title claims abstract description 31
- 150000008117 polysulfides Polymers 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 15
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 3
- 150000002118 epoxides Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 6
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920003986 novolac Polymers 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 19
- 125000003700 epoxy group Chemical group 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920003344 Epilox® Polymers 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 3
- 229920001342 Bakelite® Polymers 0.000 description 3
- 239000004637 bakelite Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920003319 Araldite® Polymers 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic amines Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- NUPDFKWZQURWCC-UHFFFAOYSA-M benzyl-(2-hydroxyethyl)-dimethylazanium;chloride Chemical compound [Cl-].OCC[N+](C)(C)CC1=CC=CC=C1 NUPDFKWZQURWCC-UHFFFAOYSA-M 0.000 description 1
- ICNMZKKYPHCYAG-UHFFFAOYSA-M benzyl-dimethyl-[4-methyl-2-(2-methylpropyl)-2-(2-phenoxyethoxy)pentyl]azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1OCCOC(CC(C)C)(CC(C)C)C[N+](C)(C)CC1=CC=CC=C1 ICNMZKKYPHCYAG-UHFFFAOYSA-M 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940112041 peripherally acting muscle relaxants other quaternary ammonium compound in atc Drugs 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10320543A DE10320543B4 (de) | 2003-05-07 | 2003-05-07 | Verfahren zur Herstellung von Präpolymeren auf der Basis von Polysulfiden und Polyepoxiden |
| PCT/EP2004/004643 WO2004099283A1 (de) | 2003-05-07 | 2004-05-03 | Verfahren zur herstellung von präpolymeren auf der basis von polysulfiden und polyepoxiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006525390A true JP2006525390A (ja) | 2006-11-09 |
| JP2006525390A5 JP2006525390A5 (https=) | 2007-07-05 |
Family
ID=33426700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006505353A Pending JP2006525390A (ja) | 2003-05-07 | 2004-05-03 | ポリスルフィドとポリエポキシドとからプレポリマーを製造する方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20060287466A1 (https=) |
| EP (1) | EP1620484B1 (https=) |
| JP (1) | JP2006525390A (https=) |
| CN (1) | CN1802398A (https=) |
| AT (1) | ATE360655T1 (https=) |
| DE (2) | DE10320543B4 (https=) |
| ES (1) | ES2285467T3 (https=) |
| WO (1) | WO2004099283A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010516831A (ja) * | 2007-01-23 | 2010-05-20 | アクゾ ノーベル ナムローゼ フェンノートシャップ | チイランで末端停止されたポリスルフィドポリマー |
| JP2022000498A (ja) * | 2020-05-19 | 2022-01-04 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップNouryon Chemicals International B.V. | 脂肪族エポキシ末端ポリスルフィドポリマー |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2060593A1 (de) | 2007-11-13 | 2009-05-20 | Karl Nestler | Verwendung einer Abdichtungsmasse zur Herstellung einer Wasserdampfsperrschicht |
| EP2085415A1 (de) | 2008-01-28 | 2009-08-05 | Karl Nestler | Verbundsystem, Verfahren zur Herstellung desselben sowie mehrschichtiges Flächengebilde |
| CN101983217B (zh) | 2008-04-07 | 2013-10-09 | 陶氏环球技术公司 | 具有改善的低温固化性质的环氧树脂组合物和用于制备该组合物的方法和中间体 |
| EP2700683B1 (en) | 2012-08-23 | 2016-06-08 | 3M Innovative Properties Company | Structural adhesive film |
| CN113683753A (zh) * | 2020-05-19 | 2021-11-23 | 诺力昂化学品国际有限公司 | 脂族环氧封端的多硫化物聚合物 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789958A (en) * | 1951-10-30 | 1957-04-23 | Thiokol Chemical Corp | Resinous reaction products of polyepoxides and polysulfide polymers and methods of making the same |
| JPS63314233A (ja) * | 1984-07-26 | 1988-12-22 | モートン チオコール リミテッド | メルカプタン末端硬化性液体共重合体 |
| JPH02173116A (ja) * | 1988-11-29 | 1990-07-04 | Dow Chem Co:The | 硫化物含有脂肪族エポキシ樹脂 |
| JPH0693084A (ja) * | 1992-09-10 | 1994-04-05 | Toray Chiokoole Kk | 溶液型ポリサルファイド変性エポキシ樹脂、及びそれを用いた炭素繊維プリプレグ用エポキシ樹脂組成物 |
| JPH06128353A (ja) * | 1992-10-19 | 1994-05-10 | Toray Chiokoole Kk | 一液型エポキシ樹脂組成物 |
| JPH11100430A (ja) * | 1997-09-26 | 1999-04-13 | Toray Thiokol Co Ltd | ポリサルファイドポリエーテル変性エポキシ樹脂 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE528443A (https=) * | 1953-04-29 | |||
| US3017387A (en) * | 1958-07-21 | 1962-01-16 | Shell Oil Co | Polyepoxy ethers of polyhydric phenols and cured products obtained therefrom |
| US3297635A (en) * | 1963-05-31 | 1967-01-10 | Shell Oil Co | Process for curing polyepoxides and resulting products |
| BE649472A (https=) * | 1963-06-20 | 1964-12-18 | ||
| US3411940A (en) * | 1963-06-20 | 1968-11-19 | Shell Oil Co | Process for coating surfaces with polyepoxide compositions |
| US3663464A (en) * | 1970-08-13 | 1972-05-16 | Nasa | Polymeric vehicles as carriers for sulfonic acid salt of nitrosubstituted aromatic amines |
| DE3573778D1 (en) * | 1984-06-29 | 1989-11-23 | Ciba Geigy Ag | Process for the preparation of glycidyl thioethers |
| GB8419036D0 (en) * | 1984-07-26 | 1984-08-30 | Thiokol Chemicals Ltd | Liquid copolymers |
| DD232057A1 (de) * | 1984-11-30 | 1986-01-15 | Univ Schiller Jena | Verfahren zur herstellung von alpha, omega-dufinktionellen prepolymeren mit zwei glycidylendgruppen |
| US5173549A (en) * | 1988-06-17 | 1992-12-22 | Morton International, Inc. | Process for synthesizing epoxidized polysulfides |
| DE4141858A1 (de) * | 1990-12-21 | 1992-06-25 | Ciba Geigy Ag | Mit mercaptoverbindungen vorverlaengerte bisphenol a-diglycidylether |
| US5610243A (en) * | 1993-12-20 | 1997-03-11 | Morton International, Inc. | Polysulfide-epoxy thermoplastic elastomers |
| EP0901481B1 (en) * | 1996-05-21 | 2003-10-22 | ExxonMobil Chemical Patents Inc. | Purification of glycidyl esters by thin film evaporation |
| US6617399B2 (en) * | 1999-12-17 | 2003-09-09 | Henkel Loctite Corporation | Thermosetting resin compositions comprising epoxy resins, adhesion promoters, curatives based on the combination of nitrogen compounds and transition metal complexes, and polysulfide tougheners |
-
2003
- 2003-05-07 DE DE10320543A patent/DE10320543B4/de not_active Expired - Fee Related
-
2004
- 2004-05-03 AT AT04739125T patent/ATE360655T1/de active
- 2004-05-03 JP JP2006505353A patent/JP2006525390A/ja active Pending
- 2004-05-03 CN CNA2004800123453A patent/CN1802398A/zh active Pending
- 2004-05-03 US US10/555,726 patent/US20060287466A1/en not_active Abandoned
- 2004-05-03 ES ES04739125T patent/ES2285467T3/es not_active Expired - Lifetime
- 2004-05-03 EP EP04739125A patent/EP1620484B1/de not_active Expired - Lifetime
- 2004-05-03 WO PCT/EP2004/004643 patent/WO2004099283A1/de not_active Ceased
- 2004-05-03 DE DE502004003614T patent/DE502004003614D1/de not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789958A (en) * | 1951-10-30 | 1957-04-23 | Thiokol Chemical Corp | Resinous reaction products of polyepoxides and polysulfide polymers and methods of making the same |
| JPS63314233A (ja) * | 1984-07-26 | 1988-12-22 | モートン チオコール リミテッド | メルカプタン末端硬化性液体共重合体 |
| JPH02173116A (ja) * | 1988-11-29 | 1990-07-04 | Dow Chem Co:The | 硫化物含有脂肪族エポキシ樹脂 |
| JPH0693084A (ja) * | 1992-09-10 | 1994-04-05 | Toray Chiokoole Kk | 溶液型ポリサルファイド変性エポキシ樹脂、及びそれを用いた炭素繊維プリプレグ用エポキシ樹脂組成物 |
| JPH06128353A (ja) * | 1992-10-19 | 1994-05-10 | Toray Chiokoole Kk | 一液型エポキシ樹脂組成物 |
| JPH11100430A (ja) * | 1997-09-26 | 1999-04-13 | Toray Thiokol Co Ltd | ポリサルファイドポリエーテル変性エポキシ樹脂 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010516831A (ja) * | 2007-01-23 | 2010-05-20 | アクゾ ノーベル ナムローゼ フェンノートシャップ | チイランで末端停止されたポリスルフィドポリマー |
| JP2022000498A (ja) * | 2020-05-19 | 2022-01-04 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップNouryon Chemicals International B.V. | 脂肪族エポキシ末端ポリスルフィドポリマー |
| JP7394807B2 (ja) | 2020-05-19 | 2023-12-08 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップ | 脂肪族エポキシ末端ポリスルフィドポリマー |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10320543A1 (de) | 2004-12-16 |
| WO2004099283A1 (de) | 2004-11-18 |
| ATE360655T1 (de) | 2007-05-15 |
| WO2004099283A8 (de) | 2006-03-09 |
| CN1802398A (zh) | 2006-07-12 |
| DE502004003614D1 (de) | 2007-06-06 |
| DE10320543B4 (de) | 2006-02-02 |
| US20060287466A1 (en) | 2006-12-21 |
| EP1620484A1 (de) | 2006-02-01 |
| EP1620484B1 (de) | 2007-04-25 |
| ES2285467T3 (es) | 2007-11-16 |
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