CA1081890A - Polyester resins - Google Patents
Polyester resinsInfo
- Publication number
- CA1081890A CA1081890A CA288,746A CA288746A CA1081890A CA 1081890 A CA1081890 A CA 1081890A CA 288746 A CA288746 A CA 288746A CA 1081890 A CA1081890 A CA 1081890A
- Authority
- CA
- Canada
- Prior art keywords
- polyester resin
- solution
- resin composition
- composition according
- ester
- 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
- 229920001225 polyester resin Polymers 0.000 title claims abstract description 39
- 239000004645 polyester resin Substances 0.000 title claims abstract description 39
- 229920000642 polymer Polymers 0.000 claims abstract description 43
- 239000000178 monomer Substances 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 230000009974 thixotropic effect Effects 0.000 claims abstract description 21
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 229920006337 unsaturated polyester resin Polymers 0.000 claims abstract description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 52
- 229920005989 resin Polymers 0.000 claims description 28
- 239000011347 resin Substances 0.000 claims description 28
- -1 aralkyl ester Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 3
- 239000013008 thixotropic agent Substances 0.000 claims description 3
- JELFVXVEOTVGKC-UHFFFAOYSA-N 3-dodecoxycarbonylbut-3-enoic acid Chemical compound CCCCCCCCCCCCOC(=O)C(=C)CC(O)=O JELFVXVEOTVGKC-UHFFFAOYSA-N 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229940063559 methacrylic acid Drugs 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229920000728 polyester Polymers 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- QMFMKJYWNVEZCV-UHFFFAOYSA-N C1(=CC=CC=C1)C.C(C(=C)C)(=O)O.C=CC1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C.C(C(=C)C)(=O)O.C=CC1=CC=CC=C1 QMFMKJYWNVEZCV-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- LGDAGYXJBDILKZ-UHFFFAOYSA-N [2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LGDAGYXJBDILKZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000129 polyhexylmethacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater 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
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polyesters Or Polycarbonates (AREA)
- Developing Agents For Electrophotography (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB43076/76A GB1592352A (en) | 1976-10-16 | 1976-10-16 | Preparation of polyester resin/fibre laminates and compositions for use therein |
| GB43076/76 | 1976-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1081890A true CA1081890A (en) | 1980-07-15 |
Family
ID=10427229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA288,746A Expired CA1081890A (en) | 1976-10-16 | 1977-10-14 | Polyester resins |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4218546A (enExample) |
| JP (1) | JPS5356253A (enExample) |
| AU (1) | AU519321B2 (enExample) |
| BE (1) | BE859773A (enExample) |
| BR (1) | BR7706901A (enExample) |
| CA (1) | CA1081890A (enExample) |
| DE (1) | DE2746357A1 (enExample) |
| DK (1) | DK458077A (enExample) |
| FI (1) | FI773059A7 (enExample) |
| FR (1) | FR2367796A1 (enExample) |
| GB (1) | GB1592352A (enExample) |
| IL (1) | IL53136A (enExample) |
| NL (1) | NL7711300A (enExample) |
| NO (1) | NO773532L (enExample) |
| PT (1) | PT67158B (enExample) |
| SE (1) | SE7711597L (enExample) |
| ZA (1) | ZA776130B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE4221T1 (de) * | 1979-10-12 | 1983-08-15 | Dsm Resins Bv | Ungesaettigte polyesterzusammensetzungen und ihre anwendung. |
| US4294941A (en) * | 1979-12-14 | 1981-10-13 | Owens-Corning Fiberglas Corporation | Compatible low shrink resin systems |
| US5198480A (en) * | 1990-08-08 | 1993-03-30 | The Standard Oil Company | Suppressants for unsaturated polyester resins |
| US5206077A (en) * | 1991-11-25 | 1993-04-27 | The Dow Chemical Company | Low vaporizable ethylenically unsaturated monomer emission vinyl ester and polyester resin compositions |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3014001A (en) * | 1957-01-04 | 1961-12-19 | Reichhold Chemicals Inc | Production of glossy, air-curing, noninhibited polyester coatings |
| NL235151A (enExample) | 1958-01-15 | |||
| US3225117A (en) * | 1962-06-15 | 1965-12-21 | Cincinnati Milling Machine Co | Weather-resistant plastics |
| US3701748A (en) * | 1966-07-20 | 1972-10-31 | Rohm & Haas | Unsaturated polyester resinous compositions |
| US3449468A (en) * | 1967-01-20 | 1969-06-10 | Ppg Industries Inc | Method of reducing porosity and pinholes in unsaturated polyester resin coatings |
| JPS5222977B2 (enExample) * | 1971-08-06 | 1977-06-21 | ||
| US3879318A (en) * | 1972-06-02 | 1975-04-22 | Rohm & Haas | Organic amide containing compositions and process for thickening control of polyesters |
| JPS5416693B2 (enExample) * | 1972-06-14 | 1979-06-25 | ||
| IT1004335B (it) | 1973-03-15 | 1976-07-10 | Koppers Co Inc | Composizione da stampaggio di poliestere ritardante la fiamma |
| US4008294A (en) * | 1974-11-27 | 1977-02-15 | W. R. Grace & Co. | Thickened polyester composition containing ultrafine polypropylene fibers |
| DE2513255C2 (de) | 1975-03-26 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Stabile organische, schwundarm härtbare Dispersionen auf Basis ungesättigter Polyesterharze und thermoplastischer Polymerer |
-
1976
- 1976-10-16 GB GB43076/76A patent/GB1592352A/en not_active Expired
-
1977
- 1977-10-14 BR BR7706901A patent/BR7706901A/pt unknown
- 1977-10-14 US US05/842,269 patent/US4218546A/en not_active Expired - Lifetime
- 1977-10-14 SE SE7711597A patent/SE7711597L/xx not_active Application Discontinuation
- 1977-10-14 BE BE181786A patent/BE859773A/xx unknown
- 1977-10-14 JP JP12342077A patent/JPS5356253A/ja active Granted
- 1977-10-14 DE DE19772746357 patent/DE2746357A1/de not_active Withdrawn
- 1977-10-14 ZA ZA00776130A patent/ZA776130B/xx unknown
- 1977-10-14 NO NO773532A patent/NO773532L/no unknown
- 1977-10-14 FI FI773059A patent/FI773059A7/fi not_active Application Discontinuation
- 1977-10-14 CA CA288,746A patent/CA1081890A/en not_active Expired
- 1977-10-14 NL NL7711300A patent/NL7711300A/xx not_active Application Discontinuation
- 1977-10-14 DK DK458077A patent/DK458077A/da unknown
- 1977-10-14 PT PT67158A patent/PT67158B/pt unknown
- 1977-10-14 FR FR7730929A patent/FR2367796A1/fr not_active Withdrawn
- 1977-10-14 IL IL53136A patent/IL53136A/xx unknown
- 1977-10-17 AU AU29793/77A patent/AU519321B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4218546A (en) | 1980-08-19 |
| ZA776130B (en) | 1978-06-28 |
| FI773059A7 (fi) | 1978-04-17 |
| FR2367796A1 (fr) | 1978-05-12 |
| GB1592352A (en) | 1981-07-08 |
| BR7706901A (pt) | 1978-07-18 |
| NO773532L (no) | 1978-04-18 |
| AU519321B2 (en) | 1981-11-26 |
| JPS5356253A (en) | 1978-05-22 |
| AU2979377A (en) | 1979-04-26 |
| DE2746357A1 (de) | 1978-04-27 |
| NL7711300A (nl) | 1978-04-18 |
| IL53136A0 (en) | 1977-12-30 |
| BE859773A (fr) | 1978-04-14 |
| DK458077A (da) | 1978-04-17 |
| PT67158B (en) | 1979-03-20 |
| PT67158A (en) | 1977-11-01 |
| SE7711597L (sv) | 1978-04-17 |
| IL53136A (en) | 1981-01-30 |
| JPS571531B2 (enExample) | 1982-01-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |