DE1770547C3 - Verfahren zur Herstellung von Polyestern durch Polykondensation eines Glykolterephthalats in Gegenwart einer vorher hergestellten Lösung von Germaniumdioxid - Google Patents
Verfahren zur Herstellung von Polyestern durch Polykondensation eines Glykolterephthalats in Gegenwart einer vorher hergestellten Lösung von GermaniumdioxidInfo
- Publication number
- DE1770547C3 DE1770547C3 DE1770547A DE1770547A DE1770547C3 DE 1770547 C3 DE1770547 C3 DE 1770547C3 DE 1770547 A DE1770547 A DE 1770547A DE 1770547 A DE1770547 A DE 1770547A DE 1770547 C3 DE1770547 C3 DE 1770547C3
- Authority
- DE
- Germany
- Prior art keywords
- germanium dioxide
- solution
- glycol
- polycondensation
- water
- 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
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 title claims description 128
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 96
- 229940119177 germanium dioxide Drugs 0.000 title claims description 64
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 37
- 238000006068 polycondensation reaction Methods 0.000 title claims description 26
- 229920000728 polyester Polymers 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 19
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 title claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 description 47
- 239000003054 catalyst Substances 0.000 description 18
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 230000008901 benefit Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- -1 glycol terephthalates Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000009884 interesterification Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- PACUAVNICWDZOT-UHFFFAOYSA-M manganese(2+) 4-methoxycarbonylbenzoate Chemical compound COC(C1=CC=C(C(=O)[O-])C=C1)=O.[Mn+2] PACUAVNICWDZOT-UHFFFAOYSA-M 0.000 description 1
- CESXSDZNZGSWSP-UHFFFAOYSA-L manganese(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].CC([O-])=O.CC([O-])=O CESXSDZNZGSWSP-UHFFFAOYSA-L 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C08G63/85—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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25645/67A GB1221788A (en) | 1967-06-02 | 1967-06-02 | Process for the preparation of polyestesters of terephthalic acid and glycols |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1770547A1 DE1770547A1 (de) | 1972-01-13 |
| DE1770547B2 DE1770547B2 (de) | 1979-08-09 |
| DE1770547C3 true DE1770547C3 (de) | 1983-03-10 |
Family
ID=10231032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1770547A Expired DE1770547C3 (de) | 1967-06-02 | 1968-05-31 | Verfahren zur Herstellung von Polyestern durch Polykondensation eines Glykolterephthalats in Gegenwart einer vorher hergestellten Lösung von Germaniumdioxid |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3511811A (ref) |
| AT (1) | AT279177B (ref) |
| BE (1) | BE715933A (ref) |
| CH (1) | CH517134A (ref) |
| CS (1) | CS166683B2 (ref) |
| DE (1) | DE1770547C3 (ref) |
| FR (1) | FR1567637A (ref) |
| GB (1) | GB1221788A (ref) |
| NL (1) | NL150816B (ref) |
| SE (1) | SE342050B (ref) |
| YU (1) | YU31829B (ref) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119614A (en) * | 1977-12-22 | 1978-10-10 | Monsanto Company | Process for making polyester polymer |
| JPH07507831A (ja) * | 1992-06-15 | 1995-08-31 | アライド−シグナル・インコーポレーテッド | 鎖長延長ポリエステル類およびブロックまたはグラフトコポリエステル類を製造する改良された方法 |
| CN113480719B (zh) * | 2021-07-16 | 2023-03-10 | 武汉科技大学 | 一种基于高香草酸的生物质聚酯p、制备及其应用 |
| CN114031755B (zh) * | 2021-12-24 | 2023-04-07 | 苏州苏震生物工程有限公司 | 一种聚对苯二甲酸乙二酯的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2578660A (en) * | 1949-09-21 | 1951-12-18 | Du Pont | Process for polymerizing ethylene glycol terephthalate |
| BE536161A (ref) * | 1954-03-02 | |||
| GB911245A (en) * | 1960-02-11 | 1962-11-21 | Ici Ltd | Manufacture of filament and film-forming polyesters |
| BE614859A (ref) * | 1961-03-09 | |||
| NL297106A (ref) * | 1962-08-27 | |||
| NL121071C (ref) * | 1964-03-03 |
-
1967
- 1967-06-02 GB GB25645/67A patent/GB1221788A/en not_active Expired
-
1968
- 1968-05-27 US US732017A patent/US3511811A/en not_active Expired - Lifetime
- 1968-05-27 SE SE7072/68A patent/SE342050B/xx unknown
- 1968-05-31 BE BE715933D patent/BE715933A/xx not_active IP Right Cessation
- 1968-05-31 AT AT525368A patent/AT279177B/de active
- 1968-05-31 YU YU1272/68A patent/YU31829B/xx unknown
- 1968-05-31 CH CH814268A patent/CH517134A/de not_active IP Right Cessation
- 1968-05-31 DE DE1770547A patent/DE1770547C3/de not_active Expired
- 1968-05-31 NL NL686807741A patent/NL150816B/xx not_active IP Right Cessation
- 1968-06-01 CS CS4066A patent/CS166683B2/cs unknown
- 1968-06-04 FR FR1567637D patent/FR1567637A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE715933A (ref) | 1968-10-16 |
| AT279177B (de) | 1970-02-25 |
| GB1221788A (en) | 1971-02-10 |
| DE1770547B2 (de) | 1979-08-09 |
| YU127268A (en) | 1973-06-30 |
| SE342050B (ref) | 1972-01-24 |
| FR1567637A (ref) | 1969-05-16 |
| YU31829B (en) | 1973-12-31 |
| CS166683B2 (ref) | 1976-03-29 |
| CH517134A (de) | 1971-12-31 |
| NL6807741A (ref) | 1968-11-25 |
| NL150816B (nl) | 1976-09-15 |
| US3511811A (en) | 1970-05-12 |
| DE1770547A1 (de) | 1972-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8381 | Inventor (new situation) |
Free format text: CONIX, ANDRE JAN, DR., ANTWERPEN, BE JEURISSEN, LAMBERT GASTON, MORTSEL, BE |
|
| C3 | Grant after two publication steps (3rd publication) |