FI108039B - Förfarande för framställning av högmolekylära polyestrar - Google Patents
Förfarande för framställning av högmolekylära polyestrar Download PDFInfo
- Publication number
- FI108039B FI108039B FI944037A FI944037A FI108039B FI 108039 B FI108039 B FI 108039B FI 944037 A FI944037 A FI 944037A FI 944037 A FI944037 A FI 944037A FI 108039 B FI108039 B FI 108039B
- Authority
- FI
- Finland
- Prior art keywords
- polyester
- process according
- weight
- viscosity number
- value
- Prior art date
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 61
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000007790 solid phase Substances 0.000 claims abstract description 20
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 14
- 238000009833 condensation Methods 0.000 claims description 22
- -1 aromatic dicarboxylic acids Chemical class 0.000 claims description 17
- 238000005886 esterification reaction Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 230000032050 esterification Effects 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000001451 organic peroxides Chemical class 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 16
- 150000002009 diols Chemical class 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 229920001169 thermoplastic Polymers 0.000 description 8
- 239000004416 thermosoftening plastic Substances 0.000 description 8
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 5
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 5
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 5
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 229910052756 noble gas Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 230000006911 nucleation Effects 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- WQJUBZMZVKITBU-UHFFFAOYSA-N (3,4-dimethyl-4-phenylhexan-3-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(CC)C(C)(CC)C1=CC=CC=C1 WQJUBZMZVKITBU-UHFFFAOYSA-N 0.000 description 1
- TWUDHDJKTHYMGY-QHHAFSJGSA-N (e)-3-methylpent-2-ene-1,5-diol Chemical compound OCCC(/C)=C/CO TWUDHDJKTHYMGY-QHHAFSJGSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 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
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000009420 retrofitting Methods 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C08G63/80—Solid-state polycondensation
-
- 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
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
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)
- Injection Moulding Of Plastics Or The Like (AREA)
Claims (12)
1. Förfarande för framställning av högmolekylär polyester genom förestring eller omestring och därefter polykonden-sation av aromatiska dikarboxylsyror eller deras poly-esterbildande derivat med en blandning av alkan- och al-25 kendioler väsentligen utan syre och i närvaro av en kata-lysator, kännetecknat därav, att polykondensationssteget förs tili ett viskositetstal i omrädet 50 - 140 cm1/g, och den sälunda erhällna polyestern underkastas sedan en fast-fasefterkondensation till dess att erfordrat vis-30 kositetstal uppnätts. : - - 2. Förfarande enligt krav 1, kännetecknat därav, att det första polykondensationssteget förs tili ett viskositetstal i omrädet 60 - 120 cm1/g. 35 Förfarande enligt kraven 1 och 2, kännetecknat därav, att fastfaskondensationen utförs vid en temperatur, som är 5-60°C under polyesterns smältpunkt. 108039
4. Förfarande enligt kraven 1-3, kännetecknat därav, att där används dessutom en radikalbildare i en mängd i omrä-det 0,001 - 8 vikt%. 5 5. Förfarande enligt kraven 1-3, kännetecknat därav, att radikalbildaren används i en mängd i omrädet 0,01 - 5 vikt%.
6. Förfarande enligt kraven 1-5, kännetecknat därav, att 10 radikalbildaren sönderfaller vid en temperatur i omrädet 180 - 280°C.
7. Förfarande enligt kraven 1-6, käiinetecknat därav, att radikalbildaren sönderfaller med en halveringstid i omrä- 15 det 5 s - 18 h.
8. Förfarande enligt kraven 1-7, kännetecknat därav, att som radikalbildare används organiska peroxider. 20 9. Förfarande enligt kraven 1-7, kännetecknat därav, att radikalbildaren uppvisar en labil C-C-bindning.
10. Förfarande enligt kraven 1-7, kännetecknat därav, att radikalbildaren uppvisar en labil organisk N-N-bindning. 25
11. Förfarande enligt kraven 1-10, kännetecknat därav, att till slutviskositetstal installs £ 500 cm3/g.
12. Förfarande enligt kraven 1-11, kännetecknat därav, 30 att ett slutviskositetstal i omrädet 100 - 450 cm3/g installs. «
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4330062 | 1993-09-06 | ||
| DE4330062A DE4330062A1 (de) | 1993-09-06 | 1993-09-06 | Verfahren zur Herstellung hochmolekularer Polyester |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI944037A0 FI944037A0 (sv) | 1994-09-02 |
| FI944037A FI944037A (sv) | 1995-03-07 |
| FI108039B true FI108039B (sv) | 2001-11-15 |
Family
ID=6496939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI944037A FI108039B (sv) | 1993-09-06 | 1994-09-02 | Förfarande för framställning av högmolekylära polyestrar |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5468441A (sv) |
| EP (1) | EP0641813B1 (sv) |
| JP (1) | JP3266420B2 (sv) |
| AT (1) | ATE166899T1 (sv) |
| CA (1) | CA2131396A1 (sv) |
| DE (2) | DE4330062A1 (sv) |
| DK (1) | DK0641813T3 (sv) |
| ES (1) | ES2118288T3 (sv) |
| FI (1) | FI108039B (sv) |
| NO (1) | NO306023B1 (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4423141A1 (de) * | 1994-07-01 | 1996-01-04 | Hoechst Ag | Polyester-Dispersionen als Additiv in Beschichtungsmitteln |
| KR101068030B1 (ko) * | 2011-06-03 | 2011-09-28 | 주식회사 지오솔테크 | 내가수분해성 및 생분해성 지방족/방향족 코폴리에스테르 수지 조성물 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2509790A1 (de) * | 1975-03-06 | 1976-09-16 | Basf Ag | Verfahren zur herstellung hochviskoser thermoplastischer polyester-formmassen |
| US4355155A (en) * | 1980-10-14 | 1982-10-19 | Gaf Corporation | Thermoplastic copolyester elastomer |
| US5051531A (en) * | 1988-05-31 | 1991-09-24 | Atochem North America, Inc. | Antioxidant-peroxides |
| DE3820362A1 (de) * | 1988-06-15 | 1990-03-15 | Basf Ag | Verfahren zur kontinuierlichen herstellung von linearen thermoplastischen polyestern |
| DE4308049A1 (de) * | 1993-03-13 | 1994-09-15 | Huels Gaf Chemie Gmbh | Verfahren zur Herstellung hochmolekularer Polyester |
-
1993
- 1993-09-06 DE DE4330062A patent/DE4330062A1/de not_active Withdrawn
-
1994
- 1994-07-07 DK DK94110562T patent/DK0641813T3/da active
- 1994-07-07 DE DE59406120T patent/DE59406120D1/de not_active Expired - Fee Related
- 1994-07-07 AT AT94110562T patent/ATE166899T1/de not_active IP Right Cessation
- 1994-07-07 ES ES94110562T patent/ES2118288T3/es not_active Expired - Lifetime
- 1994-07-07 EP EP94110562A patent/EP0641813B1/de not_active Expired - Lifetime
- 1994-08-22 US US08/293,557 patent/US5468441A/en not_active Expired - Lifetime
- 1994-09-02 CA CA002131396A patent/CA2131396A1/en not_active Abandoned
- 1994-09-02 FI FI944037A patent/FI108039B/sv active
- 1994-09-05 NO NO943282A patent/NO306023B1/no unknown
- 1994-09-05 JP JP21150594A patent/JP3266420B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FI944037A0 (sv) | 1994-09-02 |
| EP0641813B1 (de) | 1998-06-03 |
| ES2118288T3 (es) | 1998-09-16 |
| NO306023B1 (no) | 1999-09-06 |
| NO943282D0 (no) | 1994-09-05 |
| CA2131396A1 (en) | 1995-03-07 |
| JP3266420B2 (ja) | 2002-03-18 |
| DE4330062A1 (de) | 1995-03-09 |
| ATE166899T1 (de) | 1998-06-15 |
| FI944037A (sv) | 1995-03-07 |
| DK0641813T3 (da) | 1999-03-22 |
| NO943282L (no) | 1995-03-07 |
| US5468441A (en) | 1995-11-21 |
| DE59406120D1 (de) | 1998-07-09 |
| EP0641813A1 (de) | 1995-03-08 |
| JPH0782360A (ja) | 1995-03-28 |
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