GB1130558A - Processes for preparing polyesters - Google Patents
Processes for preparing polyestersInfo
- Publication number
- GB1130558A GB1130558A GB5188565A GB5188565A GB1130558A GB 1130558 A GB1130558 A GB 1130558A GB 5188565 A GB5188565 A GB 5188565A GB 5188565 A GB5188565 A GB 5188565A GB 1130558 A GB1130558 A GB 1130558A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- cyclobutanediol
- tetramethyl
- acids
- 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
- 229920000728 polyester Polymers 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 11
- -1 aliphatic diester Chemical class 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
- 239000000539 dimer Substances 0.000 abstract 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 abstract 3
- 150000002334 glycols Chemical class 0.000 abstract 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 2
- 150000002531 isophthalic acids Chemical class 0.000 abstract 2
- 150000002611 lead compounds Chemical class 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 150000003330 sebacic acids Chemical class 0.000 abstract 2
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 abstract 1
- RGCVYEOTYJCNOS-UHFFFAOYSA-N (4-cyano-2-methylphenyl)boronic acid Chemical compound CC1=CC(C#N)=CC=C1B(O)O RGCVYEOTYJCNOS-UHFFFAOYSA-N 0.000 abstract 1
- LMIDQHXGBYBMLR-UHFFFAOYSA-N 1,4-dimethylcyclohexane-1,4-dicarboxylic acid Chemical compound OC(=O)C1(C)CCC(C)(C(O)=O)CC1 LMIDQHXGBYBMLR-UHFFFAOYSA-N 0.000 abstract 1
- WWYFPDXEIFBNKE-UHFFFAOYSA-N 4-(hydroxymethyl)benzoic acid Chemical class OCC1=CC=C(C(O)=O)C=C1 WWYFPDXEIFBNKE-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- DRUKNYVQGHETPO-UHFFFAOYSA-N Nonanedioic acid dimethyl ester Natural products COC(=O)CCCCCCCC(=O)OC DRUKNYVQGHETPO-UHFFFAOYSA-N 0.000 abstract 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 150000001279 adipic acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 abstract 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 abstract 1
- 229920001748 polybutylene Polymers 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 229920006324 polyoxymethylene Polymers 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 abstract 1
- 229960001860 salicylate Drugs 0.000 abstract 1
- 239000007790 solid phase Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 150000003504 terephthalic acids Chemical class 0.000 abstract 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 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
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
-
- 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
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
1,130,558. Polyesters. EASTMAN KODAK CO. 7 Dec., 1965 [7 Dec., 1964], No. 51885/65. Heading C3R. In the manufacture of linear polyesters by reacting an aliphatic diester of a dicarboxylic acid or carbonic acid with a dihydroxy compound at least 10 mol per cent of which consists of a 2:2:4:4-tetraalkyl-1 :3-cyclobutanediol, a lead compound is used as a catalyst. Specified lead compounds are the nitrate (which may be ethylene glycol treated), sulphate, silicate, phosphite, carbonate, borate, acetate, propionate, butyrate, stearate, tartarate, salicylate, phthalate, maleate, oxide (e.g. PhO, PhO 2 or Ph 3 O 4 ) and organo-lead compounds wherein the organic radicals are C 1-25 alkyls, C 6-10 cycloalkyls or C 6-10 aryls. Specified dicarboxylic acids are terephthalic, hexahydroterephthalic, p : p<SP>1</SP> - sulphonyldibenzoic, 4 : 1<SP>1</SP> - dipheylether dicarboxylic 4 : 4<SP>1</SP> - diphenic, 4 : 41 - ethylenedioxydibenzoic, 4 : 4<SP>1 </SP>- methylenedibenzoic, 4 : 4<SP>1</SP> - benzophenonedicarboxylic, 4 : 4<SP>1</SP> - vinylenedibenzoic, 1 : 4-, 1: 5- or 2 : 6-naphthalenedicarboxylic, 2 : 5- or 2 : 6-norcamphanedicarboxylic, isophthalic, orthophthalic, hexahydrophthalic, 1 : 4- phenylenediacetic, 1 : 4 - cyclohexanediacetic, oxalic, succinic, adipic, 2 : 2 : 4 - trimethyladipic, sebacic, azelaic 2 - ethylsuberic, 2 : 2- diethyladipic, dimethylmalonic and dimer acids; also dicarboxy diethyl ether. Suitable modifying glycols are C 2-10 polymethylene glycols, 2 : 2 - dimethyl - 1: 3 - propanediol, 2 - methyl - 1 : 5 - pentanediol, p - xylylene glycol, 1 :4 - di-(hydroxyethyl)benzene quinitol, 1 : 4 - cyclohexanedimethanol, dimer glycols and polyglycols of formula where R 4 is a hydrogen atom or an aliphatic, aromatic or cycloaliphatic hydrocarbon radical, a is 1-4 and b is 2-100. The reaction mixture may also include hydroxycarboxylic acids (e.g. 4 - hydroxybutanoic, 6-hydroxyhexanoic, 2 : 2 - dimethyl - 3 - hydroxypropionic or p - hydroxymethylbenzoic acids. The process for making the polyesters comprises a normal ester-interchange reaction followed by a normal melt polymerization or solid phase polymerization reaction. Examples describe the manufacture of polyesters by reacting (1)-(5) 2 : 2 4 : 4 - tetramethyl - 1 : 3 - cyclobutanediol and dialkyl esters of terephthalic, azalaic, 4 : 4<SP>1</SP> - sulphonyldibenzoic or transcyclohexane - 1 : 4 - dicarboxylic acids; (6) and (7) 2 : 4 - dimethyl - 2:4 - diisopropyl - 1:3 - cyclobutanediol (or a mixture thereof with 1 : 6 - hexanediol) and dimethyl terephthalate; (8), (9), (10), (12), (13), (14) and (15) 2 : 2 : 4 : 4- tetramethyl - 1 : 3 - cyclobutanediol, dimethyl terephthalate and 1 : 4 - cyclohexanedimethanol, polytetramethylene glycol (M.W. 3100), mixed polytetramethylene glycols (M.W.'s 1600 and 3100), polybutylene glycol (M.W. 1000), polyethylene glycol (M.W. 1000) and dimer glycol; (11) 2 : 2 : 4 : 4- (18) 2 : 2 : 4 : 4-tetramethyl - 1 : 3- cyclobutanediol and dimethyl hexahydroterephthalic acid; tetramethyl - 1 : 3 - cyclobutanediol, polytetramethylene glycol (M.W. 1000), dimethyl terephthalate and dimethyl azelate; (17) and (20) 2 : 2 : 4 : 4 - tetramethyl- 1 : 3 - cyclobutanediol and dimethylisophthalate or dimethyl - 2,6 - naphthalenedicarboxylate; (18), (19) and (21) 2 : 2 : 4 : 4 - tetramethyl - 1 : 3 - cyclobutane - diol and mixtures of dimethyl esters of terephthalic and succinic, azolaic, adipic, sepacic, dimer or isophthalic acids, mixtures of dimethyl esters isophathalic and azeloic or adipic acids and a mixture of the dimethyl esters of 2 : 6 - naphthalenedicarboxylic and sebacic acids; (18) 2 : 2 4 : 4- tetramethyl - plus 2 : 2 : 4 : 4 - tetraethyl- 1 : 3 - cyclobutanediol and dimethyl isophthalate (16) and (21) 2 :2 : 4 :4 - tetramethyl- : 1 : 3- cyclobutanediol and dibutyl carbonate with or without the dimethyl esters of sebacic, isophthalic or terephthalic acids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41624164A | 1964-12-07 | 1964-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1130558A true GB1130558A (en) | 1968-10-16 |
Family
ID=23649161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5188565A Expired GB1130558A (en) | 1964-12-07 | 1965-12-07 | Processes for preparing polyesters |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1456345A (en) |
| GB (1) | GB1130558A (en) |
Cited By (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007001570A1 (en) * | 2005-06-17 | 2007-01-04 | Eastman Chemical Company | Film(s) and/or sheet(s) made from polyester compositions containing cyclobutanediol and articles made therefrom |
| US7462684B2 (en) | 2005-03-02 | 2008-12-09 | Eastman Chemical Company | Preparation of transparent, multilayered articles containing polyesters comprising a cyclobutanediol and homogeneous polyamide blends |
| JP2009513791A (en) * | 2005-10-28 | 2009-04-02 | イーストマン ケミカル カンパニー | Polyester composition comprising cyclobutanediol and certain heat stabilizers and / or reaction products thereof |
| US7704605B2 (en) | 2006-03-28 | 2010-04-27 | Eastman Chemical Company | Thermoplastic articles comprising cyclobutanediol having a decorative material embedded therein |
| US7737246B2 (en) | 2005-12-15 | 2010-06-15 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol, cyclohexanedimethanol, and ethylene glycol and manufacturing processes therefor |
| US7786252B2 (en) | 2005-03-02 | 2010-08-31 | Eastman Chemical Company | Preparation of transparent multilayered articles |
| WO2010114508A1 (en) * | 2009-04-01 | 2010-10-07 | Eastman Chemical Company | Improved process for the production of polyesters |
| US7955533B2 (en) | 2005-03-02 | 2011-06-07 | Eastman Chemical Company | Process for the preparation of transparent shaped articles |
| US7955674B2 (en) | 2005-03-02 | 2011-06-07 | Eastman Chemical Company | Transparent polymer blends containing polyesters comprising a cyclobutanediol and articles prepared therefrom |
| US7959836B2 (en) | 2005-03-02 | 2011-06-14 | Eastman Chemical Company | Process for the preparation of transparent, shaped articles containing polyesters comprising a cyclobutanediol |
| US7959998B2 (en) | 2005-03-02 | 2011-06-14 | Eastman Chemical Company | Transparent, oxygen-scavenging compositions containing polyesters comprising a cyclobutanediol and articles prepared therefrom |
| US7964258B2 (en) | 2005-03-02 | 2011-06-21 | Eastman Chemical Company | Transparent, oxygen-scavenging compositions and articles prepared therefrom |
| US7968164B2 (en) | 2005-03-02 | 2011-06-28 | Eastman Chemical Company | Transparent polymer blends and articles prepared therefrom |
| US8163850B2 (en) | 2009-02-06 | 2012-04-24 | Eastman Chemical Company | Thermosetting polyester coating compositions containing tetramethyl cyclobutanediol |
| US8168721B2 (en) | 2009-02-06 | 2012-05-01 | Eastman Chemical Company | Coating compositions containing tetramethyl cyclobutanediol |
| US8193302B2 (en) | 2005-10-28 | 2012-06-05 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol and certain phosphate thermal stabilizers, and/or reaction products thereof |
| US8198371B2 (en) | 2008-06-27 | 2012-06-12 | Eastman Chemical Company | Blends of polyesters and ABS copolymers |
| CN101193932B (en) * | 2005-06-17 | 2012-08-08 | 伊士曼化工公司 | Polyester compositions which comprise cyclobutanediol and have a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom |
| US8287970B2 (en) | 2007-11-21 | 2012-10-16 | Eastman Chemical Company | Plastic baby bottles, other blow molded articles, and processes for their manufacture |
| US8324316B2 (en) | 2009-02-06 | 2012-12-04 | Eastman Chemical Company | Unsaturated polyester resin compositions containing 2,2,2,4-tetramethyl-1,3-cyclobutanediol and articles made therefrom |
| US8394997B2 (en) | 2010-12-09 | 2013-03-12 | Eastman Chemical Company | Process for the isomerization of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
| US8420869B2 (en) | 2010-12-09 | 2013-04-16 | Eastman Chemical Company | Process for the preparation of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
| US8420868B2 (en) | 2010-12-09 | 2013-04-16 | Eastman Chemical Company | Process for the preparation of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
| US8501287B2 (en) | 2007-11-21 | 2013-08-06 | Eastman Chemical Company | Plastic baby bottles, other blow molded articles, and processes for their manufacture |
| US8586701B2 (en) | 2005-10-28 | 2013-11-19 | Eastman Chemical Company | Process for the preparation of copolyesters based on 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
| US8895654B2 (en) | 2008-12-18 | 2014-11-25 | Eastman Chemical Company | Polyester compositions which comprise spiro-glycol, cyclohexanedimethanol, and terephthalic acid |
| US9029461B2 (en) | 2009-02-06 | 2015-05-12 | Eastman Chemical Company | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
| US9029460B2 (en) | 2009-02-06 | 2015-05-12 | Stacey James Marsh | Coating compositions containing acrylic and aliphatic polyester blends |
| US9169388B2 (en) | 2006-03-28 | 2015-10-27 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof |
| US9487619B2 (en) | 2014-10-27 | 2016-11-08 | Eastman Chemical Company | Carboxyl functional curable polyesters containing tetra-alkyl cyclobutanediol |
| US9598533B2 (en) | 2005-11-22 | 2017-03-21 | Eastman Chemical Company | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom |
| US9598602B2 (en) | 2014-11-13 | 2017-03-21 | Eastman Chemical Company | Thermosetting compositions based on phenolic resins and curable poleyester resins made with diketene or beta-ketoacetate containing compounds |
| US9650539B2 (en) | 2014-10-27 | 2017-05-16 | Eastman Chemical Company | Thermosetting compositions based on unsaturated polyesters and phenolic resins |
| US9982125B2 (en) | 2012-02-16 | 2018-05-29 | Eastman Chemical Company | Clear semi-crystalline articles with improved heat resistance |
| US9988553B2 (en) | 2016-02-22 | 2018-06-05 | Eastman Chemical Company | Thermosetting coating compositions |
| US10011737B2 (en) | 2016-03-23 | 2018-07-03 | Eastman Chemical Company | Curable polyester polyols and their use in thermosetting soft feel coating formulations |
| US10526444B2 (en) | 2015-09-25 | 2020-01-07 | Eastman Chemical Company | Polymers containing cyclobutanediol and 2,2-bis(hydroxymethyl)alkylcarboxylic acid |
| US10676565B2 (en) | 2015-05-19 | 2020-06-09 | Eastman Chemical Company | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3489721A (en) * | 1967-06-01 | 1970-01-13 | Fmc Corp | Process for preparing polyesters with cadmium,lead,zinc,or manganese-hydroxide as a transesterification catalyst |
| US3522216A (en) * | 1967-06-21 | 1970-07-28 | Fmc Corp | Preparation of polyesters with nickel,manganese,aluminum,or cadmium borate as polycondensation catalysts |
| US3507836A (en) * | 1967-07-19 | 1970-04-21 | Fmc Corp | Preparation of polyesters from a bis-hydroxyalkyl ester of an aromatic dicarboxylic acid |
| US4076693A (en) * | 1975-12-22 | 1978-02-28 | Owens-Illinois, Inc. | Terephthalic acid/p,p-sulfonyldibenzoic acid/ethylene glycol/neopentyl glycol polyester compositions and containers made therefrom |
| US4049631A (en) * | 1975-12-22 | 1977-09-20 | Owens-Illinois, Inc. | Isophthalic acid/p,p-sulfonyldibenzoic acid/ethylene glycol/neopentyl glycol polyester compositions and containers made therefrom |
| JP3448158B2 (en) * | 1995-05-31 | 2003-09-16 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | Copolyester composition |
-
1965
- 1965-12-06 FR FR41008A patent/FR1456345A/en not_active Expired
- 1965-12-07 GB GB5188565A patent/GB1130558A/en not_active Expired
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|---|---|
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