CA2111969A1 - Method of producing a polyester, and use of the polyester thus produced - Google Patents
Method of producing a polyester, and use of the polyester thus producedInfo
- Publication number
- CA2111969A1 CA2111969A1 CA 2111969 CA2111969A CA2111969A1 CA 2111969 A1 CA2111969 A1 CA 2111969A1 CA 2111969 CA2111969 CA 2111969 CA 2111969 A CA2111969 A CA 2111969A CA 2111969 A1 CA2111969 A1 CA 2111969A1
- Authority
- CA
- Canada
- Prior art keywords
- ppm
- polyester
- polycondensation
- antimony
- germanium
- 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.)
- Abandoned
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000000835 fiber Substances 0.000 claims abstract description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 150000002290 germanium Chemical class 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- -1 polyethylene Polymers 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 229920001634 Copolyester Polymers 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229910052787 antimony Inorganic materials 0.000 abstract description 9
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052732 germanium Inorganic materials 0.000 abstract description 9
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052744 lithium Inorganic materials 0.000 abstract description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract description 2
- 239000005020 polyethylene terephthalate Substances 0.000 abstract description 2
- MMINFSMURORWKH-UHFFFAOYSA-N 3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical group O=C1OCCOC(=O)C2=CC=C1C=C2 MMINFSMURORWKH-UHFFFAOYSA-N 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 26
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000011572 manganese Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000556720 Manga Species 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- FNIHDXPFFIOGKL-UHFFFAOYSA-N disodium;dioxido(oxo)germane Chemical compound [Na+].[Na+].[O-][Ge]([O-])=O FNIHDXPFFIOGKL-UHFFFAOYSA-N 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- WYOFTXWVYIGTCT-UHFFFAOYSA-K [OH-].[Sb+3].OCC([O-])=O.OCC([O-])=O Chemical compound [OH-].[Sb+3].OCC([O-])=O.OCC([O-])=O WYOFTXWVYIGTCT-UHFFFAOYSA-K 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- XWTXZJITNNRDLC-UHFFFAOYSA-K bis[(2-hydroxyacetyl)oxy]alumanyl 2-hydroxyacetate Chemical compound [Al+3].OCC([O-])=O.OCC([O-])=O.OCC([O-])=O XWTXZJITNNRDLC-UHFFFAOYSA-K 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229940119177 germanium dioxide Drugs 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229940096055 prax Drugs 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 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 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater 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
- C08G63/78—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
- C08G63/78—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
- C08G63/86—Germanium, antimony, or compounds thereof
- C08G63/863—Germanium 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)
- Artificial Filaments (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH134892 | 1992-04-27 | ||
| CH1348/92-0 | 1992-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2111969A1 true CA2111969A1 (en) | 1993-11-11 |
Family
ID=4208378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2111969 Abandoned CA2111969A1 (en) | 1992-04-27 | 1993-04-21 | Method of producing a polyester, and use of the polyester thus produced |
Country Status (11)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE145656T1 (de) * | 1991-01-16 | 1996-12-15 | Schweizerische Viscose | Verfahren zur herstellung eines polyesters. |
| WO1994013732A1 (en) * | 1992-12-04 | 1994-06-23 | Toray Industries, Inc. | Thermal lamination polyester film |
| EP0745629A3 (en) * | 1995-06-01 | 1997-05-07 | Enichem Spa | Low crystallization rate polyester and catalyst system for its manufacture |
| US6953768B2 (en) | 2002-11-26 | 2005-10-11 | Teck Cominco Metals Ltd. | Multi-component catalyst system for the polycondensation manufacture of polyesters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3651017A (en) * | 1967-12-29 | 1972-03-21 | Kurashiki Rayon Co | Process for the preparation of polyesters |
| US3635900A (en) * | 1969-10-28 | 1972-01-18 | Fmc Corp | Polyester condensation process using alkali metal germanates |
-
1993
- 1993-04-21 CZ CZ94174A patent/CZ17494A3/cs unknown
- 1993-04-21 WO PCT/CH1993/000105 patent/WO1993022367A1/de not_active Application Discontinuation
- 1993-04-21 HU HU9400236A patent/HU212446B/hu not_active IP Right Cessation
- 1993-04-21 CA CA 2111969 patent/CA2111969A1/en not_active Abandoned
- 1993-04-21 JP JP5518809A patent/JPH06509386A/ja active Pending
- 1993-04-21 SK SK90-94A patent/SK9094A3/sk unknown
- 1993-04-21 AU AU38865/93A patent/AU3886593A/en not_active Abandoned
- 1993-04-21 PL PL30637593A patent/PL306375A1/xx unknown
- 1993-04-21 TW TW82103064A patent/TW227006B/zh active
- 1993-04-21 EP EP93907749A patent/EP0591488A1/de not_active Withdrawn
- 1993-04-26 AR AR32482293A patent/AR246751A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| TW227006B (enrdf_load_html_response) | 1994-07-21 |
| AU3886593A (en) | 1993-11-29 |
| PL306375A1 (en) | 1995-03-20 |
| HUT69043A (en) | 1995-08-28 |
| WO1993022367A1 (de) | 1993-11-11 |
| CZ17494A3 (en) | 1994-06-15 |
| EP0591488A1 (de) | 1994-04-13 |
| HU212446B (en) | 1996-06-28 |
| SK9094A3 (en) | 1994-08-10 |
| AR246751A1 (es) | 1994-09-30 |
| HU9400236D0 (en) | 1994-05-30 |
| JPH06509386A (ja) | 1994-10-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |