DE1645394A1 - Verfahren zur Herstellung von Polyestern,insbesondere von linearen Polyaethylenterephthalaten - Google Patents
Verfahren zur Herstellung von Polyestern,insbesondere von linearen PolyaethylenterephthalatenInfo
- Publication number
- DE1645394A1 DE1645394A1 DE19661645394 DE1645394A DE1645394A1 DE 1645394 A1 DE1645394 A1 DE 1645394A1 DE 19661645394 DE19661645394 DE 19661645394 DE 1645394 A DE1645394 A DE 1645394A DE 1645394 A1 DE1645394 A1 DE 1645394A1
- Authority
- DE
- Germany
- Prior art keywords
- production
- compounds
- stabilizing
- polymer
- reaction mixture
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 19
- 229920000728 polyester Polymers 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- -1 polyethylene terephthalates Polymers 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 title claims description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 20
- 230000000087 stabilizing effect Effects 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 238000002845 discoloration Methods 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- QPGQPZQYAMNOPE-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate;sodium Chemical compound [Na].COC(=O)C1=CC=CC(C(=O)OC)=C1 QPGQPZQYAMNOPE-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 239000004246 zinc acetate Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- HTXMGVTWXZBZNC-UHFFFAOYSA-N 3,5-bis(methoxycarbonyl)benzenesulfonic acid Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(S(O)(=O)=O)=C1 HTXMGVTWXZBZNC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 2
- REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 1
- JBZUQIYXDGKYRA-UHFFFAOYSA-N COC(C1=CC=C(C(=O)OC)C=C1)=O.[Na] Chemical compound COC(C1=CC=C(C(=O)OC)C=C1)=O.[Na] JBZUQIYXDGKYRA-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 229910010252 TiO3 Inorganic materials 0.000 description 1
- YAPRQJNRASHMAZ-UHFFFAOYSA-N [Ca].COC(=O)C1=CC=CC=C1 Chemical compound [Ca].COC(=O)C1=CC=CC=C1 YAPRQJNRASHMAZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000035899 viability Effects 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2316465 | 1965-10-16 | ||
| IT1020765 | 1965-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1645394A1 true DE1645394A1 (de) | 1970-05-14 |
Family
ID=26326319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661645394 Pending DE1645394A1 (de) | 1965-10-16 | 1966-10-06 | Verfahren zur Herstellung von Polyestern,insbesondere von linearen Polyaethylenterephthalaten |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1645394A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| NL (1) | NL6614483A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0399742A3 (en) * | 1989-05-22 | 1991-11-21 | Hoechst Celanese Corporation | Catalyst system and process for preparing polyethylene terephthalate |
-
1966
- 1966-10-06 DE DE19661645394 patent/DE1645394A1/de active Pending
- 1966-10-14 NL NL6614483A patent/NL6614483A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0399742A3 (en) * | 1989-05-22 | 1991-11-21 | Hoechst Celanese Corporation | Catalyst system and process for preparing polyethylene terephthalate |
| US5153164A (en) * | 1989-05-22 | 1992-10-06 | Hoechst Celanese Corporation | Catalyst system for preparing polyethylene terephthalate |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6614483A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-04-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE976641C (de) | Verfahren zur Herstellung von polymeren AEthern | |
| DE2224562A1 (de) | Verfahren zur Gewinnung von Polyestern hohen Molekulargewichts | |
| DE1645494A1 (de) | Verfahren zur Herstellung von faserbildenden Polyestern | |
| DE2600701A1 (de) | Flammwidrige polyester und ihre verwendung | |
| DE10322099A1 (de) | Polymerisationskatalysator für die Herstellung von Polyestern, Verfahren zur Herstellung von Polyethylenterephthalat und Verwendung des Polymerisationskatalysators | |
| DE1292398B (de) | Verfahren zur Herstellung von hochpolymeren Polyestern | |
| DE1108432B (de) | Verfahren zur Herstellung von Polyaethylenterephthalat | |
| DE1959436A1 (de) | Verfahren zur Herstellung von modifizierten film- oder faserbildenden Polyestern | |
| DE1520079A1 (de) | Verfahren zur Herstellung hochpolymerer Polymethylenterephthalate | |
| CH495395A (de) | Verfahren zur Herstellung von synthetischen hochmolekularen Polyestern | |
| DE1595378C3 (de) | Verfahren zur Herstellung von modifizierten Polyestern | |
| DE1645394A1 (de) | Verfahren zur Herstellung von Polyestern,insbesondere von linearen Polyaethylenterephthalaten | |
| DE1247542B (de) | Spinnmassen auf Grundlage von Gemischen, die lineare Polyester und Zusatzstoffe enthalten | |
| DE1469143B2 (de) | Polyesterformmassen | |
| DE1950553A1 (de) | Verfahren zur Herstellung von Polyaethylenterephthalat | |
| DE1945594A1 (de) | Verfahren zur Herstellung von aromatischen Polyestern | |
| CH410414A (de) | Verfahren zur Herstellung von Mischpolyestern aus Diglykolestern aromatischer Dicarbonsäuren und Phosphorsäure | |
| DE1669445C3 (de) | Verfahren zur Herstellung von modifizierten Polyestern | |
| DE1720237A1 (de) | Verfahren zur Herstellung von Polyesteraethern | |
| DE2526749C2 (de) | Verfahren zur Herstellung von flammwidrigem Polybutylenterephthalat | |
| DE1058256B (de) | Verfahren zur Herstellung von hochpolymeren Polymethylenterephthalaten | |
| CH417113A (de) | Verfahren zur Herstellung von Metallsalzen von w-Oxy-polyoxyalkylenoxybenzol-sulfonsäuren | |
| DE2303350C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2105928A1 (de) | Lineare Polyatherester, Verfahren zu derer. Herstellung und hieraus ge formte Gegen Stande | |
| DE2336640A1 (de) | Verfahren zur herstellung von sulfonatmodifizierten polyestern |