JP5256217B2 - エポキシ樹脂重合用促進剤 - Google Patents
エポキシ樹脂重合用促進剤 Download PDFInfo
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- JP5256217B2 JP5256217B2 JP2009551023A JP2009551023A JP5256217B2 JP 5256217 B2 JP5256217 B2 JP 5256217B2 JP 2009551023 A JP2009551023 A JP 2009551023A JP 2009551023 A JP2009551023 A JP 2009551023A JP 5256217 B2 JP5256217 B2 JP 5256217B2
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- 229920000647 polyepoxide Polymers 0.000 title claims description 30
- 239000003822 epoxy resin Substances 0.000 title claims description 29
- 238000006116 polymerization reaction Methods 0.000 title description 7
- 150000001412 amines Chemical class 0.000 claims description 106
- 239000000203 mixture Substances 0.000 claims description 105
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 74
- 239000004593 Epoxy Substances 0.000 claims description 47
- 239000003795 chemical substances by application Substances 0.000 claims description 44
- 235000011187 glycerol Nutrition 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 16
- 150000003512 tertiary amines Chemical group 0.000 claims description 13
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 10
- 150000003141 primary amines Chemical group 0.000 claims description 9
- 150000003335 secondary amines Chemical group 0.000 claims description 9
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 claims description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 2
- YONXRSPFKCGRNL-UHFFFAOYSA-N 4-piperazin-1-ylbutan-1-amine Chemical compound NCCCCN1CCNCC1 YONXRSPFKCGRNL-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 2
- XMSVKICKONKVNM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-diamine Chemical compound C1CC2(N)C(N)CC1C2 XMSVKICKONKVNM-UHFFFAOYSA-N 0.000 claims description 2
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 claims description 2
- KEJJRKANNZHYOB-UHFFFAOYSA-N 1,3-bis(aminomethyl)cyclohexan-1-amine Chemical compound NCC1CCCC(N)(CN)C1 KEJJRKANNZHYOB-UHFFFAOYSA-N 0.000 claims 1
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 19
- 229920000768 polyamine Polymers 0.000 description 10
- 238000009472 formulation Methods 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000004848 polyfunctional curative Substances 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- -1 amine compound Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZSSVGSJIAFEHDW-WYIOCLOVSA-N (4r,4ar,7s,7ar,12bs)-9-(3-aminopropoxy)-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol Chemical compound O[C@H]([C@@H]1O2)C=C[C@H]3[C@]4([H])N(C)CC[C@]13C1=C2C(OCCCN)=CC=C1C4 ZSSVGSJIAFEHDW-WYIOCLOVSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- ILVAQMRNWMBWFC-UHFFFAOYSA-N n'-cyclohexylmethanediamine Chemical compound NCNC1CCCCC1 ILVAQMRNWMBWFC-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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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
- C08G59/18—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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
-
- 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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Description
た水素原子の数で該分子の分子量を割ることにより計算することができる。一例としてAEPに対してはAEPの分子量(129.2)を3で割って43.07のAHEWを得ることができる。2種以上の成分の配合物のAHEWは、アミンのAHEWで割った各アミンの重量分率の和の逆数をとることにより計算される。また重量分率を用いる代わりに、アミンのAHEWで割った各アミンの重量%の値の和により100を割った値もまた配合物のAHEWである。グリセリンのような非反応性の成分に対してはAHEWは無限大と考えられるので、非反応性の成分に対する%の項は0になり、含ませる必要はない。例えば重量分率を用いるとアミンA(AHEW=40)が1/3、アミンB(AHEW=60)が1/3、およびアミン性水素基をもたない非反応性のヒドロキシル含有化合物が1/3の配合物のAHEWは1を((1/3)/40+(1/3)/60+0)で割った72に等しい。エポキシ硬化剤がポリアミド硬化剤の場合には、アミド基の窒素原子に結合した水素原子は含まれない。これらの水素原子は一般にエポキシ基とは反応しないからである。
のようなポリエポキシと、エポキシ硬化剤、例えばポリアミンまたはポリアミンの配合物との間の反応から得られる。ここでポリアミンは式
H2N−R−NH2
のジアミンまたはこのようなアミンと他のアミンとの配合物であることができ、Rは炭素数1〜50の炭化水素基であるか炭素数1〜50のポリエーテル基であり、特に式
てAHEW=81の促進剤組成物をつくった。
Claims (16)
- a.N−アミノエチルピペラジンを必須成分とする少なくとも1種のアミン;および
b.グリセリン
を含んで成る、エポキシ硬化剤含有エポキシ樹脂の硬化に有用な促進剤組成物であって、該促進剤組成物は10〜300の範囲のアミン水素当量(AHEW)を有し、該促進剤組成物のAHEWは該エポキシ硬化剤のAHEWに合致することを特徴とする促進剤組成物。 - 該促進剤組成物は55〜65の範囲のAHEWを有することを特徴とする請求項1記載の促進剤組成物。
- 該促進剤組成物は75〜90の範囲のAHEWを有することを特徴とする請求項1記載の促進剤組成物。
- 該促進剤組成物は140〜160の範囲のAHEWを有することを特徴とする請求項1記載の促進剤組成物。
- 該促進剤組成物は60のAHEWを有することを特徴とする請求項1記載の促進剤組成物。
- 該促進剤組成物は81のAHEWを有することを特徴とする請求項1記載の促進剤組成物。
- 該少なくとも1種のアミンはN−アミノブチルピペラジン、1,4−ビス−(3−アミノプロピル)ピペラジン、およびそれらの組合わせから成る群から選ばれるピペラジンを含んで成ることを特徴とする請求項1記載の促進剤組成物。
- 該少なくとも1種のアミンはイソフォロンジアミン、ノルボルナンジアミン、m−キシレンジアミン、メンタンジアミン、エチレンジアミン、およびそれらの組合わせから成る群から選ばれるジアミンを含んで成ることを特徴とする請求項1記載の促進剤組成物。
- 該少なくとも1種のアミンはビス(p−アミノシクロヘキシル)メタン、ビス(4−アミノ−3−メチルシクロヘキシル)メタン、ジアミノシクロヘキサン、1,3−ビス(アミノメチル)シクロヘキシルアミン、およびそれらの組合わせから成る群から選ばれるアミンを含んで成ることを特徴とする請求項1記載の促進剤組成物。
- 該少なくとも1種のアミンはジエチレントリアミン、トリエチレンテトラミン、アミノプロピルモルフォリン、アミノエチルエタノールアミン、およびそれらの組合わせから成る群から選ばれることを特徴とする請求項1記載の促進剤組成物。
- 該少なくとも1種のアミンはエチレンアミン、エタノールアミン、およびそれらの組合わせから成る群から選ばれることを特徴とする請求項1記載の促進剤組成物。
- 該少なくとも1種のアミンは第1級アミン基を有するアミン、第2級アミン基を有するアミン、第3級アミン基を有するアミン、第1級アミン基および第2級アミン基を有するアミン、第1級アミン基および第3級アミン基を有するアミン、第2級アミン基および第3級アミン基を有するアミン、第1級アミン基、第2級アミン基および第3級アミン基を有するアミン、およびそれらの組合わせから成る群から選ばれることを特徴とする請求項1記載の促進剤組成物。
- 請求項1記載の促進剤組成物を製造する方法であって、
a.N−アミノエチルピペラジンを必須成分とする少なくとも1種のアミンおよびグリ
セリンを用意し、
b.該少なくとも1種のアミンとグリセリンとを接触させる
段階を含んで成ることを特徴とする方法。 - 該促進剤組成物は60または81のAHEWをもっていることを特徴とする請求項13記載の方法。
- a.N−アミノエチルピペラジンを必須成分とする少なくとも1種のアミン、グリセリ
ン、エポキシ硬化剤およびポリエポキシを用意し、
b.該少なくとも1種のアミンとグリセリンとを含んで成る促進剤組成物の存在下にお
いてエポキシ硬化剤およびポリエポキシを接触させる
段階を含んで成り、該促進剤組成物は10〜300の範囲のAHEWを有し、該促進剤組成物のAHEWは該エポキシ硬化剤のAHEWに合致することを特徴とするエポキシ樹脂の製造方法。 - 促進剤組成物は60または81のAHEWを有し、エポキシ硬化剤は60または81のAHEWを有することを特徴とする請求項15記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US90278707P | 2007-02-22 | 2007-02-22 | |
US60/902,787 | 2007-02-22 | ||
PCT/US2008/054646 WO2008103868A1 (en) | 2007-02-22 | 2008-02-22 | Accelerators for polymerization of epoxy resins |
Publications (2)
Publication Number | Publication Date |
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JP2010534250A JP2010534250A (ja) | 2010-11-04 |
JP5256217B2 true JP5256217B2 (ja) | 2013-08-07 |
Family
ID=39710507
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2009551023A Expired - Fee Related JP5256217B2 (ja) | 2007-02-22 | 2008-02-22 | エポキシ樹脂重合用促進剤 |
Country Status (8)
Country | Link |
---|---|
US (2) | US20100099842A1 (ja) |
EP (1) | EP2114669A4 (ja) |
JP (1) | JP5256217B2 (ja) |
CN (1) | CN101616793B (ja) |
AU (1) | AU2008218296B2 (ja) |
CA (1) | CA2678017A1 (ja) |
MX (1) | MX2009008947A (ja) |
WO (1) | WO2008103868A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8980979B2 (en) | 2009-03-17 | 2015-03-17 | Dow Global Technologies Llc | Curable compositions containing cyclic diamine and cured products therefrom |
WO2011112405A1 (en) * | 2010-03-11 | 2011-09-15 | Huntsman Petrochemical Llc | Cycloaliphatic carbonates as reactive diluents in epoxy resins |
EP2386599A1 (en) * | 2010-04-30 | 2011-11-16 | Cognis IP Management GmbH | Epoxy curing compositions and methods |
US9550912B2 (en) * | 2014-12-19 | 2017-01-24 | Hexion Inc | Curing agent for epoxy coatings |
EP3577152B1 (en) * | 2017-02-06 | 2023-04-19 | Huntsman Petrochemical LLC | Curing agent for epoxy resins |
US11542364B2 (en) | 2017-02-06 | 2023-01-03 | Huntsman Petrochemical Llc | Curing agent for epoxy resins |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4195153A (en) * | 1978-10-19 | 1980-03-25 | Texaco Development Corporation | Non-crystallizing epoxy resin accelerator |
US4818801A (en) * | 1982-01-18 | 1989-04-04 | Minnesota Mining And Manufacturing Company | Ophthalmic device comprising a polymer of a telechelic perfluoropolyether |
US4495081A (en) * | 1982-07-13 | 1985-01-22 | The Dow Chemical Company | Compositions containing polyether polyols and aliphatic primary amines |
JPS59232118A (ja) | 1983-06-15 | 1984-12-26 | Matsushita Electric Works Ltd | 封止用注型材料 |
US4521572A (en) * | 1984-02-22 | 1985-06-04 | Texaco Inc. | Epoxy resin modified polyether polyols from mixed initiators |
JPS62280216A (ja) * | 1986-05-28 | 1987-12-05 | Aica Kogyo Co Ltd | エポキシ系樹脂組成物 |
US4724253A (en) * | 1986-06-13 | 1988-02-09 | The Dow Chemical Company | Adducts of partially hydrolyzed epoxy resins and polyamines |
JPH0714995B2 (ja) * | 1986-12-27 | 1995-02-22 | 東洋電機製造株式会社 | エポキシ樹脂硬化促進剤 |
CA1338243C (en) * | 1989-01-30 | 1996-04-09 | Steven Andrew Lohnes | Additive for two component epoxy resin compositions |
US5243014A (en) * | 1990-07-25 | 1993-09-07 | Shomer John A | Homogeneous accelerator system for epoxy resins |
JP3092249B2 (ja) * | 1991-10-11 | 2000-09-25 | 味の素株式会社 | 酸無水物系一液性エポキシ樹脂組成物 |
JP3153046B2 (ja) | 1993-05-31 | 2001-04-03 | 日東電工株式会社 | 液晶表示素子用透明樹脂基板 |
US6962964B2 (en) * | 2003-02-06 | 2005-11-08 | Air Products And Chemicals, Inc. | Hydrogenation of methylenedianiline homologs and epoxy resins cured with same |
US7504460B2 (en) | 2005-03-07 | 2009-03-17 | Delphi Technologies, Inc. | Composition of aromatic or cycloaliphatic amine-derived polyepoxide and polyamine |
JP5279176B2 (ja) * | 2006-06-29 | 2013-09-04 | エア プロダクツ アンド ケミカルズ インコーポレイテッド | エポキシ樹脂用硬化剤および塗料組成物 |
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2008
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- 2008-02-22 WO PCT/US2008/054646 patent/WO2008103868A1/en active Application Filing
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Also Published As
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WO2008103868A1 (en) | 2008-08-28 |
US20130090450A1 (en) | 2013-04-11 |
JP2010534250A (ja) | 2010-11-04 |
EP2114669A1 (en) | 2009-11-11 |
MX2009008947A (es) | 2009-09-03 |
AU2008218296B2 (en) | 2012-05-24 |
CA2678017A1 (en) | 2008-08-28 |
EP2114669A4 (en) | 2015-08-26 |
CN101616793A (zh) | 2009-12-30 |
US9505875B2 (en) | 2016-11-29 |
US20100099842A1 (en) | 2010-04-22 |
CN101616793B (zh) | 2015-11-25 |
AU2008218296A1 (en) | 2008-08-28 |
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