CA1224299A - Process for improving mechanical properties of epoxy resins by addition of cobalt ions - Google Patents
Process for improving mechanical properties of epoxy resins by addition of cobalt ionsInfo
- Publication number
- CA1224299A CA1224299A CA000465621A CA465621A CA1224299A CA 1224299 A CA1224299 A CA 1224299A CA 000465621 A CA000465621 A CA 000465621A CA 465621 A CA465621 A CA 465621A CA 1224299 A CA1224299 A CA 1224299A
- Authority
- CA
- Canada
- Prior art keywords
- cobalt
- epoxy
- iii
- epoxy resin
- solvent
- 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
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 41
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 35
- 229910001429 cobalt ion Inorganic materials 0.000 title claims abstract description 25
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 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 title abstract description 8
- 229920005989 resin Polymers 0.000 claims abstract description 27
- 239000011347 resin Substances 0.000 claims abstract description 27
- 230000001976 improved effect Effects 0.000 claims abstract description 18
- 150000002500 ions Chemical class 0.000 claims abstract description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 54
- 239000004593 Epoxy Substances 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 150000002924 oxiranes Chemical class 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 14
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229920003986 novolac Polymers 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- JAWGVVJVYSANRY-UHFFFAOYSA-N cobalt(3+) Chemical compound [Co+3] JAWGVVJVYSANRY-UHFFFAOYSA-N 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 7
- 239000010941 cobalt Substances 0.000 claims description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 7
- 238000007872 degassing Methods 0.000 claims description 7
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 claims description 6
- -1 cobalt (III) ions Chemical class 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 150000004984 aromatic diamines Chemical class 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000011417 postcuring Methods 0.000 claims description 3
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical class NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 claims description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical class C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 230000000704 physical effect Effects 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- JUPWRUDTZGBNEX-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical group [Co].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O JUPWRUDTZGBNEX-UHFFFAOYSA-N 0.000 claims 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- ITNADJKYRCCJNX-UHFFFAOYSA-N 3-(2,3-diaminophenyl)sulfonylbenzene-1,2-diamine Chemical class NC1=CC=CC(S(=O)(=O)C=2C(=C(N)C=CC=2)N)=C1N ITNADJKYRCCJNX-UHFFFAOYSA-N 0.000 claims 1
- YQIMPOZJASMUNN-UHFFFAOYSA-N 4-(4,4-diaminocyclohexa-1,5-dien-1-yl)sulfonylcyclohexa-2,4-diene-1,1-diamine Chemical group C1=CC(N)(N)CC=C1S(=O)(=O)C1=CCC(N)(N)C=C1 YQIMPOZJASMUNN-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000012258 stirred mixture Substances 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 6
- 230000001070 adhesive effect Effects 0.000 abstract description 6
- 238000005266 casting Methods 0.000 abstract description 6
- 239000002131 composite material Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 19
- 238000007792 addition Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 238000009835 boiling Methods 0.000 description 6
- 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 5
- 238000009472 formulation Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000004700 cobalt complex Chemical class 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000005009 epoxy-anhydride resin Substances 0.000 description 1
- JDVIRCVIXCMTPU-UHFFFAOYSA-N ethanamine;trifluoroborane Chemical compound CCN.FB(F)F JDVIRCVIXCMTPU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011031 topaz Substances 0.000 description 1
- 229910052853 topaz Inorganic materials 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
- C08G59/18—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
- C08G59/70—Chelates
-
- 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
- C08G59/32—Epoxy compounds containing three or more epoxy groups
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)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/548,584 US4473674A (en) | 1983-11-03 | 1983-11-03 | Process for improving mechanical properties of epoxy resins by addition of cobalt ions |
| US548,584 | 1995-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1224299A true CA1224299A (en) | 1987-07-14 |
Family
ID=24189499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000465621A Expired CA1224299A (en) | 1983-11-03 | 1984-10-17 | Process for improving mechanical properties of epoxy resins by addition of cobalt ions |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4473674A (en, 2012) |
| EP (1) | EP0145165B1 (en, 2012) |
| JP (1) | JPS60124621A (en, 2012) |
| CA (1) | CA1224299A (en, 2012) |
| DE (1) | DE3462904D1 (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4473674A (en) * | 1983-11-03 | 1984-09-25 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Process for improving mechanical properties of epoxy resins by addition of cobalt ions |
| US4786668A (en) * | 1986-06-09 | 1988-11-22 | Shell Oil Company | Resin materials |
| US4861810A (en) * | 1986-06-09 | 1989-08-29 | Shell Oil Company | Resin materials based on amines |
| EP0518908B1 (de) * | 1990-03-09 | 1995-03-01 | Rütgerswerke Aktiengesellschaft | Verfahren zur polymerisation von epoxidverbindungen |
| DD292468A5 (de) | 1990-03-09 | 1991-08-01 | Zeiss Carl Jena Gmbh | Verfahren zur polymerisation von epoxidverbindungen |
| DK0508951T3 (da) * | 1991-04-08 | 1996-09-09 | Ciba Geigy Ag | Varmehærdelige blandinger |
| DE4208518A1 (de) * | 1992-03-17 | 1993-09-23 | Ruetgerswerke Ag | Hochtemperaturbestaendige elektro-laminate, verfahren zu ihrer herstellung und verwendung |
| US5541000A (en) * | 1993-08-17 | 1996-07-30 | Minnesota Mining And Manufacturing Company | Latent, thermal cure accelerators for epoxy-aromatic amine resins having lowered peak exotherms |
| DE4408865C2 (de) * | 1994-03-16 | 2001-05-17 | Raymond A & Cie | Verwendung einer einkomponentigen, adhäsiven Beschichtungsmasse zum Ausrüsten der Oberflächen von Befestigungselementen mit einer reaktiven Klebschicht |
| 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 |
| US6670430B1 (en) * | 1999-12-17 | 2003-12-30 | Henkel Loctite Corporation | Thermosetting resin compositions comprising epoxy resins, adhesion promoters, and curatives based on the combination of nitrogen compounds and transition metal complexes |
| US6893736B2 (en) * | 2001-11-19 | 2005-05-17 | Henkel Corporation | Thermosetting resin compositions useful as underfill sealants |
| US6951907B1 (en) | 2001-11-19 | 2005-10-04 | Henkel Corporation | Composition of epoxy resin, secondary amine-functional adhesion promotor and curative of nitrogen-compound and transition metal complex |
| KR100637322B1 (ko) * | 2004-10-22 | 2006-10-20 | 도레이새한 주식회사 | 전자부품용 접착테이프 조성물 |
| KR100635053B1 (ko) * | 2005-06-21 | 2006-10-16 | 도레이새한 주식회사 | 전자부품용 접착테이프 |
| EP2508546A1 (en) | 2009-12-01 | 2012-10-10 | Nagase ChemteX Corporation | Epoxy resin composition |
| TWI757508B (zh) | 2017-08-02 | 2022-03-11 | 日商笹倉機械工程股份有限公司 | 造水裝置 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1402899A (en) * | 1971-10-28 | 1975-08-13 | Gen Electric | Curable epoxy resin compositons |
| US3812214A (en) * | 1971-10-28 | 1974-05-21 | Gen Electric | Hardenable composition consisting of an epoxy resin and a metal acetylacetonate |
| US3792016A (en) * | 1972-01-06 | 1974-02-12 | Minnesota Mining & Mfg | Metal imidazolate-catalyzed systems |
| US4137275A (en) * | 1976-04-27 | 1979-01-30 | Westinghouse Electric Corp. | Latent accelerators for curing epoxy resins |
| US4113791A (en) * | 1977-03-03 | 1978-09-12 | Westinghouse Electric Corp. | Fluid solventless epoxy-anhydride compositions containing metal acetylacetonate accelerators and organic carboxylic acid co-accelerators |
| DE3135636A1 (de) * | 1981-09-09 | 1983-03-17 | Basf Ag, 6700 Ludwigshafen | Haertbare epoxidharze |
| US4473674A (en) * | 1983-11-03 | 1984-09-25 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Process for improving mechanical properties of epoxy resins by addition of cobalt ions |
-
1983
- 1983-11-03 US US06/548,584 patent/US4473674A/en not_active Expired - Fee Related
-
1984
- 1984-10-11 DE DE8484306958T patent/DE3462904D1/de not_active Expired
- 1984-10-11 EP EP84306958A patent/EP0145165B1/en not_active Expired
- 1984-10-17 CA CA000465621A patent/CA1224299A/en not_active Expired
- 1984-10-25 JP JP59223103A patent/JPS60124621A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60124621A (ja) | 1985-07-03 |
| DE3462904D1 (en) | 1987-05-07 |
| JPS6261211B2 (en, 2012) | 1987-12-21 |
| US4473674A (en) | 1984-09-25 |
| EP0145165A1 (en) | 1985-06-19 |
| EP0145165B1 (en) | 1987-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |