CA1278641C - Interpolymers of bicyclic amide acetals/dicarboxylic acid anhydrides/polyepoxides - Google Patents
Interpolymers of bicyclic amide acetals/dicarboxylic acid anhydrides/polyepoxidesInfo
- Publication number
- CA1278641C CA1278641C CA000517504A CA517504A CA1278641C CA 1278641 C CA1278641 C CA 1278641C CA 000517504 A CA000517504 A CA 000517504A CA 517504 A CA517504 A CA 517504A CA 1278641 C CA1278641 C CA 1278641C
- Authority
- CA
- Canada
- Prior art keywords
- anhydride
- bicyclic amide
- polyepoxide
- amide acetal
- group
- 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
- -1 bicyclic amide acetals Chemical class 0.000 title claims abstract description 35
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 22
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 25
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 21
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 20
- 150000008064 anhydrides Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 13
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 12
- 229940106691 bisphenol a Drugs 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 24
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- 150000001241 acetals Chemical class 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 150000002118 epoxides Chemical group 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- IQRKXTUDTIUWBP-UHFFFAOYSA-N spiro[bicyclo[2.2.1]hept-2-ene-5,3'-oxetane]-2',4'-dione Chemical compound O=C1OC(=O)C11C(C=C2)CC2C1 IQRKXTUDTIUWBP-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- HTJFSXYVAKSPNF-UHFFFAOYSA-N 2-[2-(oxiran-2-yl)ethyl]oxirane Chemical compound C1OC1CCC1CO1 HTJFSXYVAKSPNF-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 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
- C08G59/40—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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4284—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with other curing agents
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)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/772,821 US4600763A (en) | 1985-09-05 | 1985-09-05 | Interpolymers of bicyclic amide acetals/dicarboxylic acid anhydrides/polyepoxides |
| US772,821 | 1991-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1278641C true CA1278641C (en) | 1991-01-02 |
Family
ID=25096349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000517504A Expired - Lifetime CA1278641C (en) | 1985-09-05 | 1986-09-04 | Interpolymers of bicyclic amide acetals/dicarboxylic acid anhydrides/polyepoxides |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4600763A (enExample) |
| EP (1) | EP0216208B1 (enExample) |
| JP (1) | JPS62116622A (enExample) |
| AT (1) | ATE60343T1 (enExample) |
| CA (1) | CA1278641C (enExample) |
| DE (1) | DE3677111D1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4701513A (en) * | 1986-12-15 | 1987-10-20 | W. R. Grace & Co. | Novel epoxy hardeners |
| US4757125A (en) * | 1987-07-08 | 1988-07-12 | Ashland Oil, Inc. | Bicyclic amide acetal-based cure accelerators for amine curing of epoxy compositions |
| US4766196A (en) * | 1987-08-14 | 1988-08-23 | Ashland Oil, Inc. | Accelerators for the cure of epoxy resins with amine curing agents |
| US4783518A (en) * | 1987-09-28 | 1988-11-08 | Ashland Oil, Inc. | Rapid curing epoxy compositions |
| JPH0229308A (ja) * | 1988-07-19 | 1990-01-31 | Nippon Zeon Co Ltd | 反応射出成形方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1720361A1 (de) * | 1967-01-31 | 1971-07-08 | Huels Chemische Werke Ag | Verfahren zur Herstellung linearer Polyesteramide |
| CH556819A (de) * | 1970-04-22 | 1974-12-13 | Ciba Geigy Ag | Verfahren zur herstellung von neuen aminoacetalen und aminoketalen, und ihre anwendung. |
| US3673274A (en) * | 1971-03-29 | 1972-06-27 | Dow Chemical Co | Polymeric adhesive containing a polyepoxide, a carboxy terminated polybutadiene and a bis-2-oxazoline |
| US3822237A (en) * | 1971-10-22 | 1974-07-02 | Dow Chemical Co | Reaction products of polyepoxide and excess di-2-oxazoline |
| US4327200A (en) * | 1979-11-05 | 1982-04-27 | Vianova Kunstharz, A.G. | Water-dilutable oxazolidine group containing epoxy resin esters, coating compositions prepared therefrom, and their use as cathodically depositable paints |
| US4480083A (en) * | 1983-03-21 | 1984-10-30 | Desoto, Inc. | Oxazolidine-blocked amine polymers |
| US4540767A (en) * | 1984-12-04 | 1985-09-10 | Ashland Oil, Inc. | Polymers based on bicyclic amide acetals/polyepoxides/polyisocyanates |
-
1985
- 1985-09-05 US US06/772,821 patent/US4600763A/en not_active Expired - Fee Related
-
1986
- 1986-09-01 EP EP86112102A patent/EP0216208B1/en not_active Expired - Lifetime
- 1986-09-01 DE DE8686112102T patent/DE3677111D1/de not_active Expired - Lifetime
- 1986-09-01 AT AT86112102T patent/ATE60343T1/de not_active IP Right Cessation
- 1986-09-04 CA CA000517504A patent/CA1278641C/en not_active Expired - Lifetime
- 1986-09-05 JP JP61208083A patent/JPS62116622A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0216208A1 (en) | 1987-04-01 |
| ATE60343T1 (de) | 1991-02-15 |
| JPS62116622A (ja) | 1987-05-28 |
| DE3677111D1 (de) | 1991-02-28 |
| JPH0152408B2 (enExample) | 1989-11-08 |
| EP0216208B1 (en) | 1991-01-23 |
| US4600763A (en) | 1986-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |