WO1994019403B1 - Unsaturated polyester resin compositions - Google Patents
Unsaturated polyester resin compositionsInfo
- Publication number
- WO1994019403B1 WO1994019403B1 PCT/US1994/001209 US9401209W WO9419403B1 WO 1994019403 B1 WO1994019403 B1 WO 1994019403B1 US 9401209 W US9401209 W US 9401209W WO 9419403 B1 WO9419403 B1 WO 9419403B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- unsaturated polyester
- methyl
- polyester
- amended
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract 18
- 229920001225 Polyester resin Polymers 0.000 title 1
- 229920000728 polyester Polymers 0.000 claims abstract 10
- 239000002253 acid Substances 0.000 claims abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N Glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims 2
- 229940117969 NEOPENTYL GLYCOL Drugs 0.000 claims 2
- 239000003677 Sheet moulding compound Substances 0.000 claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims 2
- 238000005191 phase separation Methods 0.000 claims 2
- 238000006068 polycondensation reaction Methods 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 229920001169 thermoplastic Polymers 0.000 claims 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N Maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- -1 acrylic compound Chemical class 0.000 abstract 1
- 238000000465 moulding Methods 0.000 abstract 1
Abstract
Resinous composition for sheet molding comprising glycidyl (meth)acrylic compound and an unsaturated polyester from polyhydric alcohol(s) and ethylenically unsaturated polycarboxylic acid(s) provides high performance structural SMC products. The acrylate increases the reactivity of the polyester for preparing 'zero-shrinkage' parts.
Claims
AMENDED CLAIMS
[received by the International Bureau on 30 August 1994 (30.08.94); original claims 1 and 18 amended; remaining claims unchanged (3 pages)]
1. (Amended) A resinous composition for a sheet molding compound comprising the reaction product of:
(a) an unsaturated polyester comprising a polycondensation product of one or more polyhydric alcohols and one or more ethylenically unsaturated polycarboxylic acids; and
(b) one or more glycidyl-acrylates which copolymerize with the unsaturated polyester wherein the glycidy-acrylates are represented by the formula O R-,
II I
R2— O— C— C=CH2 wherein R, is hydrogen or an alkyl radical having 1 to 5 carbon atoms, and R2 is a glycidyl ester group having the formula
O
/ \
CH2 — CH — CH2 — R3 wherein R3 ranges from C2H2O4- to C10H8O4-
2. The composition of claim 1 wherein R-, is hydrogen or an alkyl radical having 1 to 3 carbon atoms, R2 ranges from C3H5O- to C13H13O5- and R3 ranges from C2H2O4- to C10H8O4-.
3. The composition of claim 1 wherein R-, is hydrogen or a methyl group and R2 is C3H5O-.
-16- 12. The composition of claim 8 wherein the polyhydric alcohol is a combination that includes at least one of neopentyl glycol, 1 ,4-cyclohexanedimethanol2,2,4-trimethylpantane-1 -3-pentanediol, or 2-methyl-1 ,3-propanediol.
13. The composition of claim 9 wherein the polyhydric alcohol is a combination that includes at least one of neopentyl glycol, 1 ,4-cyclohexanedimethanol,2,2,4-trimethylpantane-1 -3-pentanediol, or 2-methyl-1 ,3-propanediol.
14. The composition of claim 1 wherein the polyhydric alcohol is the combination of ethylene glycol and 2-methyl-1 ,3- propanediol.
1 5. The composition of claim 1 including: (c) one or more olefinically unsaturated monomers which copolmerizes with the unsaturated polyester.
1 6. The composition of claim 15 including:
(d) one or more low-profile thermoplastic polymers which cause phase separation and porosity during a curing reaction.
17. The composition of claim 1 6 including:
(e) one or more compatible components which are compatible with the reacted unsaturated polyester and monomer during cure.
18. (Amended) A resinous composition for a sheet molding compound comprising the reaction product of:
(a) an unsaturated polyester comprising a polycondensation product of 2-methyl-1 ,3-propanediol, ethylene glycol, phthalic anhydride and maleic anhydride; and
-17- (b) glycidyl methacrylate which copolymerizes with the unsaturated polyester.
19. The composition of claim 18 including styrene which copolymerizes with the polyester.
20. The composition of claim 18 wherein the polyester has residual acid wherein the residual acid reacts with the glycidyl methacrylate.
21. The composition of claim 18 including one or more low- profile thermoplastic polymers which cause phase separation and porosity during a curing reaction.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69425731T DE69425731T2 (en) | 1993-02-18 | 1994-02-15 | UNSATURATED POLYESTER RESIN COMPOSITIONS |
| EP94908695A EP0684969B1 (en) | 1993-02-18 | 1994-02-15 | Unsaturated polyester resin compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/019,007 US5373058A (en) | 1993-02-18 | 1993-02-18 | Unsaturated polyester resin compositions |
| US019,007 | 1993-02-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1994019403A1 WO1994019403A1 (en) | 1994-09-01 |
| WO1994019403B1 true WO1994019403B1 (en) | 1994-10-27 |
Family
ID=21790921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/001209 WO1994019403A1 (en) | 1993-02-18 | 1994-02-15 | Unsaturated polyester resin compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5373058A (en) |
| EP (1) | EP0684969B1 (en) |
| DE (1) | DE69425731T2 (en) |
| ES (1) | ES2149260T3 (en) |
| TW (1) | TW305862B (en) |
| WO (1) | WO1994019403A1 (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0719810A3 (en) * | 1994-12-27 | 1996-10-16 | Owens Corning Fiberglass Corp | Unsaturated polyester resins |
| US5688867A (en) * | 1995-05-01 | 1997-11-18 | Ferro Corporation | Low VOC unsaturated polyester systems and uses thereof |
| US5614299A (en) * | 1996-02-26 | 1997-03-25 | Kabushiki Kaisha Kobe Seiko Sho | Heat-resistant unsaturated polyester resin composition and heat-resistant fiber-reinforced composite material |
| US6358620B1 (en) * | 2000-03-02 | 2002-03-19 | Bp Corporation North America Inc. | Unsaturated polyester resin compositions |
| US6414085B1 (en) | 2000-11-22 | 2002-07-02 | Arco Chemical Technology, L.P. | Polyester resins based on terephthalic acid and 2-methyl-1,3-propanediol and processes for the preparation thereof |
| US6696521B2 (en) * | 2002-07-29 | 2004-02-24 | Arco Chemical Technology, Lp | High performance ortho UPR |
| US6986948B2 (en) * | 2002-10-21 | 2006-01-17 | Ashland, Inc. | Polyester-based dimethacrylates designed for laminating applications |
| DE10336387A1 (en) * | 2003-08-06 | 2005-03-03 | Basf Ag | Biodegradable polyester blend |
| US20050065633A1 (en) * | 2003-11-14 | 2005-03-24 | Michael Wynblatt | Systems and methods for relative control of load motion actuators |
| US20080142568A1 (en) * | 2005-04-11 | 2008-06-19 | Electrolock, Inc. | Circuit carrier board/solder pallett |
| US20070179250A1 (en) * | 2006-01-30 | 2007-08-02 | Reichhold, Inc. | Laminating resin with reduced styrene monomer |
| US20110207950A1 (en) | 2010-02-24 | 2011-08-25 | Hildeberto Nava | Vinyl-containing compounds and processes for making the same |
| DE102015100563B4 (en) * | 2015-01-15 | 2019-07-25 | Schill + Seilacher "Struktol" Gmbh | Polyester for flexibilized epoxy resins and their use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5048033A (en) * | 1973-08-31 | 1975-04-28 | ||
| NL8701932A (en) * | 1987-08-18 | 1989-03-16 | Dsm Resins Bv | THERMO-HARDBAR COMPOSITION. |
| JPH0532803A (en) * | 1991-07-26 | 1993-02-09 | Sekisui Chem Co Ltd | Thermosetting resin composition for in-mold coating molding and coated molding |
-
1993
- 1993-02-18 US US08/019,007 patent/US5373058A/en not_active Expired - Lifetime
-
1994
- 1994-02-08 TW TW083101101A patent/TW305862B/zh active
- 1994-02-15 DE DE69425731T patent/DE69425731T2/en not_active Expired - Fee Related
- 1994-02-15 EP EP94908695A patent/EP0684969B1/en not_active Expired - Lifetime
- 1994-02-15 WO PCT/US1994/001209 patent/WO1994019403A1/en active IP Right Grant
- 1994-02-15 ES ES94908695T patent/ES2149260T3/en not_active Expired - Lifetime
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