GB1158841A - Improvements relating to Polyester Resins - Google Patents
Improvements relating to Polyester ResinsInfo
- Publication number
- GB1158841A GB1158841A GB16431/66A GB1643166A GB1158841A GB 1158841 A GB1158841 A GB 1158841A GB 16431/66 A GB16431/66 A GB 16431/66A GB 1643166 A GB1643166 A GB 1643166A GB 1158841 A GB1158841 A GB 1158841A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- tris
- aminomethane
- hydroxymethyl
- ethylene glycol
- 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 1
- 239000004645 polyester resin Substances 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 12
- 239000002253 acid Substances 0.000 abstract 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 abstract 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 4
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 abstract 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 abstract 2
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 abstract 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000000524 functional group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000005462 imide group Chemical group 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 150000005846 sugar alcohols Polymers 0.000 abstract 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 abstract 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 abstract 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- RLMZHOIDXMRYMJ-UHFFFAOYSA-J 2-methylphenolate;titanium(4+) Chemical compound [Ti+4].CC1=CC=CC=C1[O-].CC1=CC=CC=C1[O-].CC1=CC=CC=C1[O-].CC1=CC=CC=C1[O-] RLMZHOIDXMRYMJ-UHFFFAOYSA-J 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229960004050 aminobenzoic acid Drugs 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 210000003298 dental enamel Anatomy 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 abstract 1
- 125000006839 xylylene group Chemical group 0.000 abstract 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/42—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes polyesters; polyethers; polyacetals
-
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/16—Polyester-imides
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/303—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups H01B3/38 or H01B3/302
- H01B3/306—Polyimides or polyesterimides
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
1,158,841. Polyesters containing oxazoline and imide groups. ASSOCIATED ELECTRICAL INDUSTRIES Ltd. 31 Jan., 1967 [14 April, 1966], No. 16431/66. Heading C3R. Thermosetting resins are made by (a) reacting at least one primary amine containing at least two hydroxyl groups one of which is in vicinal relationship to the amino group with one or more polycarboxylic acids to produce at least one hydroxycarboxylic acid containing at least one oxazoline ring between functional groups, (b) forming a reaction mass comprising the oxazoline ring-containing hydroxycarboxylic acid, at least one polycarboxylic acid and at least one polyhydric alcohol, in which reaction mass at least one imide ring is included between functional groups of a hydroxycarboxylic acid or a polycarboxylic acid and (c) heating the reaction mass to effect esterification and resinification. Specified hydroxyamines are those of formula where R<SP>111</SP> is hydrogen or an organic radical and R<SP>1</SP> and R<SP>11</SP> are organic radicals at least one of which contains a hydroxyl group, preferred hydroxyamines being tris(hydroxymethyl)- aminomethane and/or 2-amino-2-methyl-1:3- propanediol. Specified polycarboxylic acids are terephthalic acid, isophthalic acid, an imidecontaining polycarboxylic acid derived by reacting 1 mol of trimellitic anhydride with 1 mol of p-aminobenzoic acid, and imide-containing polycarboxylic acids derived by reacting 2 mols of trimellitic acid with 1 mol of a diprimary amine. Specified polyhydric alcohols are (i) those of formula where a = 1-3, b = 1-3, c = 1-3, n = 1 or 2, m = 0 or 1, X is an aromatic radical radical (especially phenylene or xylylene) and R<SP>1</SP>, R<SP>11</SP> and R<SP>111</SP> are aliphatic, cycloaliphatic or heterocycloaliphatic radicals, and (ii) those of formula where R<SP>1</SP>, R<SP>11</SP> and R<SP>111</SP> are aliphatic, cycloaliphatic or heterocycloaliphatic radicals and a, b and c are 1, 2 or 3. The alcohol components of the above may be derived from ethylene glycol, propylene glycol, neopentyl glycol, 1:4-cyclohexanedimethanol, glycerol, trimethylol ethane, trimethylol propane, pentaerythritol or tris(2-hydroxyethyl)isocyanurate. The polymers when dissolved in a solvent (e.g. cresol, xylol and naphtha) and after addition of a catalyst (e.g. tetracresyl titanate) are useful as wire enamels. In examples, the polymers were formed from (1) dimethyl terephthalate, ethylene glycol, tris(hydroxymethyl)aminomethane, isophthalic acid, 4:4<SP>1</SP>-diaminodiphenyl methane and trimellitic anhydride; (2) dimethyl terephthalate, ethylene glycol, 4:4<SP>1</SP>-diaminodiphenyl methane, trimellitic anhydride and tris(hydroxymethyl)aminomethane ; (3) dimethyl terephthalate, ethylene glycol, tris(2-hydroxyethyl)isocyanurate, tris(hydroxymethyl)aminomethane, isophthalic acid, 4:4<SP>1</SP>- diaminodiphenyl methane and trimellitic anhydride.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16431/66A GB1158841A (en) | 1966-04-14 | 1966-04-14 | Improvements relating to Polyester Resins |
| FR102786A FR1519168A (en) | 1966-04-14 | 1967-04-14 | Improved polyester resins |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16431/66A GB1158841A (en) | 1966-04-14 | 1966-04-14 | Improvements relating to Polyester Resins |
| FR102786A FR1519168A (en) | 1966-04-14 | 1967-04-14 | Improved polyester resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1158841A true GB1158841A (en) | 1969-07-23 |
Family
ID=26175602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16431/66A Expired GB1158841A (en) | 1966-04-14 | 1966-04-14 | Improvements relating to Polyester Resins |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1519168A (en) |
| GB (1) | GB1158841A (en) |
-
1966
- 1966-04-14 GB GB16431/66A patent/GB1158841A/en not_active Expired
-
1967
- 1967-04-14 FR FR102786A patent/FR1519168A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1519168A (en) | 1968-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |