CA1131831A - Low viscosity unsaturated polyester resins - Google Patents
Low viscosity unsaturated polyester resinsInfo
- Publication number
- CA1131831A CA1131831A CA342,793A CA342793A CA1131831A CA 1131831 A CA1131831 A CA 1131831A CA 342793 A CA342793 A CA 342793A CA 1131831 A CA1131831 A CA 1131831A
- Authority
- CA
- Canada
- Prior art keywords
- alkyd
- unsaturated polyester
- styrene
- acid
- employed
- 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
- 229920006337 unsaturated polyester resin Polymers 0.000 title claims abstract description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229920000180 alkyd Polymers 0.000 claims abstract description 23
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 9
- 239000001530 fumaric acid Substances 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 8
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims abstract description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims abstract description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000032050 esterification Effects 0.000 claims abstract description 3
- 238000005886 esterification reaction Methods 0.000 claims abstract description 3
- 150000002334 glycols Chemical class 0.000 claims abstract description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 claims abstract description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000003021 phthalic acid derivatives Chemical class 0.000 claims abstract description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 7
- 235000011037 adipic acid Nutrition 0.000 claims description 7
- VMKMZRBPOSNUMX-UHFFFAOYSA-N 2-(1-hydroxypropan-2-yloxy)propan-1-ol Chemical compound OCC(C)OC(C)CO VMKMZRBPOSNUMX-UHFFFAOYSA-N 0.000 claims description 4
- 238000005266 casting Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229920005989 resin Polymers 0.000 abstract description 16
- 239000011347 resin Substances 0.000 abstract description 16
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 abstract description 4
- 229940044603 styrene Drugs 0.000 description 9
- 239000004645 polyester resin Substances 0.000 description 4
- 229920006305 unsaturated polyester Polymers 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940113120 dipropylene glycol Drugs 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D19/00—Producing buttons or semi-finished parts of buttons
- B29D19/04—Producing buttons or semi-finished parts of buttons by cutting, milling, turning, stamping, or perforating moulded parts; Surface treatment of buttons
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyesters Or Polycarbonates (AREA)
- Developing Agents For Electrophotography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT31406/78A IT1160418B (it) | 1978-12-29 | 1978-12-29 | Resine poliestere insature a bassa viscosita' |
| IT31406A/78 | 1978-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1131831A true CA1131831A (en) | 1982-09-14 |
Family
ID=11233585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA342,793A Expired CA1131831A (en) | 1978-12-29 | 1979-12-28 | Low viscosity unsaturated polyester resins |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4292218A (OSRAM) |
| JP (1) | JPS55112224A (OSRAM) |
| CA (1) | CA1131831A (OSRAM) |
| DE (1) | DE2952678A1 (OSRAM) |
| FR (1) | FR2445358A1 (OSRAM) |
| GB (1) | GB2039508B (OSRAM) |
| GR (1) | GR74017B (OSRAM) |
| IT (1) | IT1160418B (OSRAM) |
| NO (1) | NO794339L (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1212746B (it) * | 1983-05-24 | 1989-11-30 | Snial Resine Poliestere Spa | Prodotti a base di poliesteri insaturi. |
| FR2571730B1 (fr) * | 1984-10-12 | 1986-12-12 | Charbonnages Ste Chimique | Procede de fabrication de resines polyesters insatures presentant un murissement lineaire avec la magnesie |
| US4546142A (en) * | 1985-01-08 | 1985-10-08 | United States Steel Corporation | Inhibiting styrene emissions in unsaturated polyester resins |
| CN105131194B (zh) * | 2015-09-30 | 2018-04-17 | 浙江伟星实业发展股份有限公司 | 一种人造牛骨纽扣及其制备方法 |
| CN114262510B (zh) * | 2022-01-17 | 2023-08-01 | 浙江飞素服饰有限公司 | 一种环保谷物树脂纽扣及其制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2944994A (en) * | 1954-07-07 | 1960-07-12 | Robertson Co H H | Method of making transparent unsaturated polyester-styrene-glass fiber composition |
| US2951823A (en) * | 1956-02-11 | 1960-09-06 | Ruetgerswerke Ag | Unsaturated polyesters of unsaturated alpha, beta-dicarboxylic acids and polyvalent alcohols |
| DE1694951A1 (de) * | 1966-07-09 | 1971-07-22 | Schering Ag | Ungesaettigte Polyesterharzmassen |
| DE1769496A1 (de) * | 1967-06-02 | 1971-09-23 | Gen Tire & Rubber Co | Polyesterharz und seine Herstellung |
| GB1276198A (en) * | 1968-10-23 | 1972-06-01 | Rohm & Haas | Moulding compositions |
| GB1295371A (OSRAM) * | 1969-12-23 | 1972-11-08 | ||
| US3715233A (en) * | 1970-09-18 | 1973-02-06 | Standard Oil Co | Process for preparing fiberglass preforms |
| US3721642A (en) * | 1970-12-10 | 1973-03-20 | Diamond Shamrock Corp | Polymerizable unsaturated polyester composition containing thermoplastic additive |
| JPS4926712B1 (OSRAM) * | 1970-12-23 | 1974-07-11 | ||
| DE2124939A1 (de) * | 1971-05-19 | 1972-12-14 | Albert Ag Chem Werke | Wärmehärtbare Formmassen und Verfahren zu deren Herstellung |
| DE2258863A1 (de) * | 1971-12-10 | 1973-06-20 | Koppers Co Inc | Aushaertbare polyesterharzpraeparate |
| DE2445958B2 (de) * | 1974-09-26 | 1978-10-12 | Hoechst Ag, 6000 Frankfurt | Knöpfe, Knopfplatten, Schnallen und Bijouterieartikel oder ihre Rohlinge, Verfahren und Formmasse zu ihrer Herstellung |
| DE2509236A1 (de) * | 1975-03-04 | 1976-09-16 | Bayer Ag | Rieselfaehige, schwundarm haertbare formmassen auf basis ungesaettigter polyesterharze |
-
1978
- 1978-12-29 IT IT31406/78A patent/IT1160418B/it active
-
1979
- 1979-12-27 GR GR60857A patent/GR74017B/el unknown
- 1979-12-27 US US06/107,710 patent/US4292218A/en not_active Expired - Lifetime
- 1979-12-27 JP JP17389579A patent/JPS55112224A/ja active Pending
- 1979-12-28 FR FR7932051A patent/FR2445358A1/fr active Granted
- 1979-12-28 GB GB7944482A patent/GB2039508B/en not_active Expired
- 1979-12-28 CA CA342,793A patent/CA1131831A/en not_active Expired
- 1979-12-28 DE DE19792952678 patent/DE2952678A1/de not_active Ceased
- 1979-12-28 NO NO794339A patent/NO794339L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4292218A (en) | 1981-09-29 |
| IT7831406A0 (it) | 1978-12-29 |
| FR2445358B1 (OSRAM) | 1984-05-18 |
| NO794339L (no) | 1980-07-01 |
| IT1160418B (it) | 1987-03-11 |
| GB2039508B (en) | 1983-03-02 |
| GB2039508A (en) | 1980-08-13 |
| FR2445358A1 (fr) | 1980-07-25 |
| JPS55112224A (en) | 1980-08-29 |
| GR74017B (OSRAM) | 1984-06-06 |
| DE2952678A1 (de) | 1980-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |