CA1043498A - Unsaturated polyester, cobalt salt, amine accelerator composition - Google Patents
Unsaturated polyester, cobalt salt, amine accelerator compositionInfo
- Publication number
- CA1043498A CA1043498A CA251,567A CA251567A CA1043498A CA 1043498 A CA1043498 A CA 1043498A CA 251567 A CA251567 A CA 251567A CA 1043498 A CA1043498 A CA 1043498A
- Authority
- CA
- Canada
- Prior art keywords
- unsaturated polyester
- polyester resin
- resin composition
- amine
- cobalt salt
- 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
- 150000001412 amines Chemical class 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- 229920006305 unsaturated polyester Polymers 0.000 title claims description 10
- 150000001868 cobalt Chemical class 0.000 title claims description 9
- 229920006337 unsaturated polyester resin Polymers 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 13
- -1 methyl ethyl keton peroxide Chemical class 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- JZBZLRKFJWQZHU-UHFFFAOYSA-N n,n,2,4,6-pentamethylaniline Chemical group CN(C)C1=C(C)C=C(C)C=C1C JZBZLRKFJWQZHU-UHFFFAOYSA-N 0.000 claims description 4
- 125000005474 octanoate group Chemical group 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 claims 1
- MDTLAOQITLWKDN-UHFFFAOYSA-N 3-[n-(3-hydroxypropyl)-2,4,6-trimethylanilino]propan-1-ol Chemical compound CC1=CC(C)=C(N(CCCO)CCCO)C(C)=C1 MDTLAOQITLWKDN-UHFFFAOYSA-N 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 2
- 238000001879 gelation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- NGZXDRGWBULKFA-NSOVKSMOSA-N (+)-Bebeerine Chemical compound C([C@@H]1N(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CCN3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 NGZXDRGWBULKFA-NSOVKSMOSA-N 0.000 description 1
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
- ULFJMPCWXPSJQL-UHFFFAOYSA-N 1-amino-2-phenylbutan-2-ol Chemical compound CCC(O)(CN)C1=CC=CC=C1 ULFJMPCWXPSJQL-UHFFFAOYSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 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
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- GQBWTAGIANQVGB-UHFFFAOYSA-N 2-[n-(carboxymethyl)anilino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)C1=CC=CC=C1 GQBWTAGIANQVGB-UHFFFAOYSA-N 0.000 description 1
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical group CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical class [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0442—Catalysts
- C08F299/0457—Nitrogen containing compounds
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)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB18198/75A GB1535787A (en) | 1975-05-01 | 1975-05-01 | Polymerizable unsaturated polyester composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043498A true CA1043498A (en) | 1978-11-28 |
Family
ID=10108340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,567A Expired CA1043498A (en) | 1975-05-01 | 1976-04-30 | Unsaturated polyester, cobalt salt, amine accelerator composition |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4046740A (forum.php) |
| JP (1) | JPS51134783A (forum.php) |
| AU (1) | AU1353676A (forum.php) |
| BE (1) | BE841306A (forum.php) |
| CA (1) | CA1043498A (forum.php) |
| DE (1) | DE2619291A1 (forum.php) |
| FR (1) | FR2309598A1 (forum.php) |
| GB (1) | GB1535787A (forum.php) |
| IT (1) | IT1059244B (forum.php) |
| NL (1) | NL7604524A (forum.php) |
| NO (1) | NO761485L (forum.php) |
| ZA (1) | ZA762379B (forum.php) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5360983A (en) * | 1976-11-12 | 1978-05-31 | Dainippon Ink & Chem Inc | Preparation of molded product |
| US4243763A (en) * | 1978-03-10 | 1981-01-06 | American Dental Association Health Foundation | Tertiary aromatic amine accelerators in acrylic resin |
| US4439554A (en) * | 1980-07-07 | 1984-03-27 | American Dental Association Health Foundation | Dioxo-piperidine substituted tertiary aromatic amine accelerators in acrylic resin |
| DE3136292A1 (de) * | 1981-09-12 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | Verwendung 3,4-disubstituierter aniline als beschleuniger fuer ungesaettigte polyesterharze |
| EP3368303B1 (en) * | 2015-10-30 | 2023-08-16 | SP Advanced Engineering Materials PVT. Ltd. | Glass laminates |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3367994A (en) * | 1965-07-20 | 1968-02-06 | Pittsburgh Plate Glass Co | Novel accelerator for unsaturated polyester resins |
| FR1490033A (fr) * | 1965-08-18 | 1967-07-28 | Basf Ag | Emploi d'amines comme activateurs de polymérisation dans le durcissement des matières à mouler à base de polyesters |
| US3541153A (en) * | 1966-07-21 | 1970-11-17 | Mobay Chemical Corp | Reductive alkylation of aniline and nitrobenzene |
| US3522309A (en) * | 1967-08-31 | 1970-07-28 | Du Pont | Reductive alkylation process for production of n-alkylated amines |
| US3504033A (en) * | 1967-09-08 | 1970-03-31 | American Cyanamid Co | Process for preparing n-tertiary-alkylanilines and their hydrohalide salts |
| US3558706A (en) * | 1968-03-14 | 1971-01-26 | Gen Electric | Alkylation of aromatic primary amino group |
| GB1218587A (en) * | 1968-07-23 | 1971-01-06 | Nat Rubber Producers Res Ass | Oxidative degradation |
| US3546295A (en) * | 1968-08-01 | 1970-12-08 | Exxon Research Engineering Co | N-cycloalkyl anilines |
| DE1769898B2 (de) * | 1968-08-02 | 1978-08-24 | Peroxid-Chemie Gmbh, 8023 Hoellriegelskreuth | Härtung ungesättigter Polyesterharze |
| US3950287A (en) * | 1971-01-29 | 1976-04-13 | Ashland Oil, Inc. | Production of thermoset water-in-oil emulsions |
| US3988272A (en) | 1971-04-20 | 1976-10-26 | Ashland Oil, Inc. | Production of thermoset water-in-oil emulsions |
| US4012512A (en) * | 1972-09-05 | 1977-03-15 | Ciba-Geigy Corporation | Animal feeds containing quinoxaline-di-n-oxide derivatives |
| DE2335906C3 (de) * | 1973-07-14 | 1978-06-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen Herstellung von N-Alkylarylaminen |
-
1975
- 1975-05-01 GB GB18198/75A patent/GB1535787A/en not_active Expired
-
1976
- 1976-04-20 US US05/678,701 patent/US4046740A/en not_active Expired - Lifetime
- 1976-04-21 ZA ZA762379A patent/ZA762379B/xx unknown
- 1976-04-28 NL NL7604524A patent/NL7604524A/xx not_active Application Discontinuation
- 1976-04-29 FR FR7612684A patent/FR2309598A1/fr not_active Withdrawn
- 1976-04-29 NO NO761485A patent/NO761485L/no unknown
- 1976-04-29 BE BE166597A patent/BE841306A/xx unknown
- 1976-04-30 DE DE19762619291 patent/DE2619291A1/de active Pending
- 1976-04-30 CA CA251,567A patent/CA1043498A/en not_active Expired
- 1976-04-30 JP JP51049770A patent/JPS51134783A/ja active Pending
- 1976-04-30 IT IT7622875A patent/IT1059244B/it active
- 1976-04-30 AU AU13536/76A patent/AU1353676A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1059244B (it) | 1982-05-31 |
| US4046740A (en) | 1977-09-06 |
| NL7604524A (nl) | 1976-11-03 |
| JPS51134783A (en) | 1976-11-22 |
| NO761485L (forum.php) | 1976-11-02 |
| FR2309598A1 (fr) | 1976-11-26 |
| ZA762379B (en) | 1977-11-30 |
| DE2619291A1 (de) | 1976-11-11 |
| AU1353676A (en) | 1977-11-03 |
| GB1535787A (en) | 1978-12-13 |
| BE841306A (fr) | 1976-10-29 |
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