GB1047072A - Production of linear polyesters of high molecular weight - Google Patents
Production of linear polyesters of high molecular weightInfo
- Publication number
- GB1047072A GB1047072A GB904064A GB904064A GB1047072A GB 1047072 A GB1047072 A GB 1047072A GB 904064 A GB904064 A GB 904064A GB 904064 A GB904064 A GB 904064A GB 1047072 A GB1047072 A GB 1047072A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reaction
- ethylene glycol
- terephthalic
- chloride
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 229920000728 polyester Polymers 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 abstract 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 abstract 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- RCZKTFHQZNLYAR-UHFFFAOYSA-N bis(2-hydroxyethyl) hexanedioate Chemical compound OCCOC(=O)CCCCC(=O)OCCO RCZKTFHQZNLYAR-UHFFFAOYSA-N 0.000 abstract 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 abstract 1
- 239000001639 calcium acetate Substances 0.000 abstract 1
- 235000011092 calcium acetate Nutrition 0.000 abstract 1
- 229960005147 calcium acetate Drugs 0.000 abstract 1
- 239000006229 carbon black Substances 0.000 abstract 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 abstract 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 abstract 1
- 229940097267 cobaltous chloride Drugs 0.000 abstract 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001261 hydroxy acids Chemical class 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000011565 manganese chloride Substances 0.000 abstract 1
- 235000002867 manganese chloride Nutrition 0.000 abstract 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 238000006068 polycondensation reaction Methods 0.000 abstract 1
- -1 polyethylene terephthalate Polymers 0.000 abstract 1
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract 1
- 239000005020 polyethylene terephthalate Substances 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 229940001593 sodium carbonate Drugs 0.000 abstract 1
- 235000017550 sodium carbonate Nutrition 0.000 abstract 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 abstract 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 abstract 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 150000003609 titanium compounds Chemical class 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 abstract 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, 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
- 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
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
-
- 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
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
In the manufacture of polyethylene terephthalate by (a) effecting an esterification or esterinterchange reaction between terephthalic acid or a dialkyl ester thereof and (b) polycondensing the product, zinc chloride or manganous chloride is used as a catalyst for the polycondensation reaction and also, possibly, for the esterification or ester-interchange reaction. Additional catalysts may also be used, e.g. titanium compounds of formula Ti(OR)4, where R is an alkyl, aryl, aralkyl, acyl, aroyl or hydroxyalkyl group; also silicic acid, caustic potash, sodium carbonate, tetraethyl ammonium hydroxide, calcium acetate, cobaltous acetate or cobaltous chloride. Reaction may also be effected in the presence of titanium dioxide, carbon black, phthalocyanine pigments or the usual phosphorous compounds, e.g. trimethyl phosphate, triethyl phosphate, triphenyl phosphite, phosphoric acid or phosphorous acid. Up to 20 mol. per cent of the terephthalic component may be replaced by another dicarboxylic acid and up to 20 mol. per cent of the ethylene glycol may be replaced by other glycols or thioglycols. Hydroxyacids may also be included as copolymerizable components. Examples describe the manufacture of polyesters by reacting (i) dimethyl terephthalate and ethylene glycol, with or without the addition of bis-(2-hydroxyethyl) adipate or bis-(2-hydroxyethyl isophthalate or (ii) terephthalic acid and ethylene glycol, with or without isophthalic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB904064A GB1047072A (en) | 1964-03-03 | 1964-03-03 | Production of linear polyesters of high molecular weight |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB904064A GB1047072A (en) | 1964-03-03 | 1964-03-03 | Production of linear polyesters of high molecular weight |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1047072A true GB1047072A (en) | 1966-11-02 |
Family
ID=9864239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB904064A Expired GB1047072A (en) | 1964-03-03 | 1964-03-03 | Production of linear polyesters of high molecular weight |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1047072A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3669921A (en) * | 1971-02-08 | 1972-06-13 | Eastman Kodak Co | Copolyester melt adhesive |
| FR2355048A1 (en) * | 1976-06-15 | 1978-01-13 | Bayer Ag | STABILIZERS FOR POLYETHYLENE TEREPHTHALATES |
| EP0044221A1 (en) * | 1980-07-14 | 1982-01-20 | E.I. Du Pont De Nemours And Company | Improved bicomponent filament and process for making same |
| US5132391A (en) * | 1990-07-02 | 1992-07-21 | Eastman Kodak Company | Polyester compositions |
| US6132868A (en) * | 1997-11-06 | 2000-10-17 | Eastman Chemical Company | Copolyester binder fibers |
| US6139954A (en) * | 1997-08-28 | 2000-10-31 | Eastman Chemical Company | Polyesters containing neopentyl glycol and fibers formed therefrom |
| US6231976B1 (en) | 1997-08-28 | 2001-05-15 | Eastman Chemical Company | Copolyester binder fibers |
| US6495656B1 (en) | 1990-11-30 | 2002-12-17 | Eastman Chemical Company | Copolyesters and fibrous materials formed therefrom |
| EP1593702A1 (en) * | 2004-05-05 | 2005-11-09 | Saudi Basic Industries Corporation | Process for the production of polyethylene terephthalate copolyester, copolyester obtained thereby and its use and catalyst useful in the process |
-
1964
- 1964-03-03 GB GB904064A patent/GB1047072A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3669921A (en) * | 1971-02-08 | 1972-06-13 | Eastman Kodak Co | Copolyester melt adhesive |
| FR2355048A1 (en) * | 1976-06-15 | 1978-01-13 | Bayer Ag | STABILIZERS FOR POLYETHYLENE TEREPHTHALATES |
| EP0044221A1 (en) * | 1980-07-14 | 1982-01-20 | E.I. Du Pont De Nemours And Company | Improved bicomponent filament and process for making same |
| US5132391A (en) * | 1990-07-02 | 1992-07-21 | Eastman Kodak Company | Polyester compositions |
| US6495656B1 (en) | 1990-11-30 | 2002-12-17 | Eastman Chemical Company | Copolyesters and fibrous materials formed therefrom |
| US6139954A (en) * | 1997-08-28 | 2000-10-31 | Eastman Chemical Company | Polyesters containing neopentyl glycol and fibers formed therefrom |
| US6197856B1 (en) * | 1997-08-28 | 2001-03-06 | Eastman Chemical Company | Copolymer binder fibers |
| US6231976B1 (en) | 1997-08-28 | 2001-05-15 | Eastman Chemical Company | Copolyester binder fibers |
| US6132868A (en) * | 1997-11-06 | 2000-10-17 | Eastman Chemical Company | Copolyester binder fibers |
| US6562938B2 (en) | 2000-05-12 | 2003-05-13 | Eastman Chemical Company | Copolyesters and fibrous materials formed therefrom |
| EP1593702A1 (en) * | 2004-05-05 | 2005-11-09 | Saudi Basic Industries Corporation | Process for the production of polyethylene terephthalate copolyester, copolyester obtained thereby and its use and catalyst useful in the process |
| WO2005105888A1 (en) * | 2004-05-05 | 2005-11-10 | Saudi Basic Industries Corporation | Process for the production of polyethylene terephthalate copolyester; copolyester obtained thereby and its use and catalyst useful in the process |
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