SK87496A3 - Process for producing polyester and copolyester by using polycondensation of initial components creating polyester and use of the polycondensing catalysts - Google Patents

Process for producing polyester and copolyester by using polycondensation of initial components creating polyester and use of the polycondensing catalysts Download PDF

Info

Publication number: SK87496A3
Authority: SK; Slovakia
Prior art keywords: polycondensation; titanium dioxide; precipitate; mol; production
Prior art date: 1994-01-07

Application number

SK874-96A

Other languages

English (en)

Slovak (sk)

Inventor

Michael Martl

Thomas Mezger

Gerriet Oberlein

Klaus Haferland

Bertram Boehringer

Ulrich Berger

Original Assignee

Akzo Nobel Nv

Priority date (The priority date 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 date listed.)

1994-01-07

Filing date

1994-12-28

Publication date

1997-04-09

1994-12-28 Application filed by Akzo Nobel Nv filed Critical Akzo Nobel Nv

1997-04-09 Publication of SK87496A3 publication Critical patent/SK87496A3/sk

Links

238000006068 polycondensation reaction Methods 0.000 title claims abstract description 79
239000003054 catalyst Substances 0.000 title claims abstract description 70
229920000728 polyester Polymers 0.000 title claims abstract description 46
229920001634 Copolyester Polymers 0.000 title claims abstract description 17
238000000034 method Methods 0.000 title claims description 32
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 110
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 52
239000004408 titanium dioxide Substances 0.000 claims abstract description 51
150000002148 esters Chemical class 0.000 claims abstract description 33
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims abstract description 28
239000000377 silicon dioxide Substances 0.000 claims abstract description 26
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims abstract description 13
229920002601 oligoester Polymers 0.000 claims abstract description 12
235000012239 silicon dioxide Nutrition 0.000 claims abstract description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 55
239000002244 precipitate Substances 0.000 claims description 43
-1 phosphorus compound Chemical class 0.000 claims description 41
238000004519 manufacturing process Methods 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 28
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 19
229910010413 TiO 2 Inorganic materials 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
229920000139 polyethylene terephthalate Polymers 0.000 claims description 14
239000005020 polyethylene terephthalate Substances 0.000 claims description 14
229910004298 SiO 2 Inorganic materials 0.000 claims description 10
239000000725 suspension Substances 0.000 claims description 10
239000010936 titanium Substances 0.000 claims description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
229910052719 titanium Inorganic materials 0.000 claims description 8
229920000180 alkyd Polymers 0.000 claims description 7
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
239000011574 phosphorus Substances 0.000 claims description 6
229920001169 thermoplastic Polymers 0.000 claims description 6
239000004416 thermosoftening plastic Substances 0.000 claims description 6
239000004721 Polyphenylene oxide Substances 0.000 claims description 5
229920000570 polyether Polymers 0.000 claims description 5
229920002635 polyurethane Polymers 0.000 claims description 5
239000004814 polyurethane Substances 0.000 claims description 5
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
229920001707 polybutylene terephthalate Polymers 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
ODTQUKVFOLFLIQ-UHFFFAOYSA-N 2-[di(propan-2-yloxy)phosphorylmethyl-propan-2-yloxyphosphoryl]oxypropane Chemical compound CC(C)OP(=O)(OC(C)C)CP(=O)(OC(C)C)OC(C)C ODTQUKVFOLFLIQ-UHFFFAOYSA-N 0.000 claims description 3
229920001225 polyester resin Polymers 0.000 claims description 3
239000004645 polyester resin Substances 0.000 claims description 3
239000002243 precursor Substances 0.000 claims description 3
JVUAGOBFIHGRCI-UHFFFAOYSA-N 1,4-dimethylidenecyclohexane;terephthalic acid Chemical compound C=C1CCC(=C)CC1.OC(=O)C1=CC=C(C(O)=O)C=C1 JVUAGOBFIHGRCI-UHFFFAOYSA-N 0.000 claims description 2
239000004973 liquid crystal related substance Substances 0.000 claims description 2
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims 1
150000002334 glycols Chemical class 0.000 claims 1
229910001928 zirconium oxide Inorganic materials 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 18
230000003197 catalytic effect Effects 0.000 abstract description 10
238000002360 preparation method Methods 0.000 abstract description 5
GHPGOEFPKIHBNM-UHFFFAOYSA-N antimony(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Sb+3].[Sb+3] GHPGOEFPKIHBNM-UHFFFAOYSA-N 0.000 abstract description 2
229910052681 coesite Inorganic materials 0.000 abstract description 2
229910052906 cristobalite Inorganic materials 0.000 abstract description 2
229910052682 stishovite Inorganic materials 0.000 abstract description 2
229910052905 tridymite Inorganic materials 0.000 abstract description 2
239000000243 solution Substances 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
229920000642 polymer Polymers 0.000 description 21
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 15
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
238000009833 condensation Methods 0.000 description 11
230000005494 condensation Effects 0.000 description 11
WOZVHXUHUFLZGK-UHFFFAOYSA-N terephthalic acid dimethyl ester Natural products COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000002253 acid Substances 0.000 description 9
230000000052 comparative effect Effects 0.000 description 9
239000012153 distilled water Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
125000004185 ester group Chemical group 0.000 description 8
239000000126 substance Substances 0.000 description 8
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical group OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 7
125000001931 aliphatic group Chemical group 0.000 description 7
230000035484 reaction time Effects 0.000 description 7
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000835 fiber Substances 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
150000001991 dicarboxylic acids Chemical class 0.000 description 5
238000004821 distillation Methods 0.000 description 5
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 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
229910008051 Si-OH Inorganic materials 0.000 description 4
229910006358 Si—OH Inorganic materials 0.000 description 4
BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 4
229910007926 ZrCl Inorganic materials 0.000 description 4
125000003158 alcohol group Chemical group 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000008188 pellet Substances 0.000 description 4
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical group OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
229910052726 zirconium Inorganic materials 0.000 description 4
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 3
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000003973 paint Substances 0.000 description 3
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
239000007790 solid phase Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
150000003609 titanium compounds Chemical class 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
229920001283 Polyalkylene terephthalate Polymers 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
SHPBBNULESVQRH-UHFFFAOYSA-N [O-2].[O-2].[Ti+4].[Zr+4] Chemical compound [O-2].[O-2].[Ti+4].[Zr+4] SHPBBNULESVQRH-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
150000008064 anhydrides Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000000470 constituent Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000001746 injection moulding Methods 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
239000004922 lacquer Substances 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
238000000465 moulding Methods 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000002245 particle Substances 0.000 description 2
150000003018 phosphorus compounds Chemical class 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
150000003077 polyols Chemical class 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
230000002269 spontaneous effect Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 0.000 description 2
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
FWQNYUYRXNWOOM-UHFFFAOYSA-N 2-nonylpropanedioic acid Chemical class CCCCCCCCCC(C(O)=O)C(O)=O FWQNYUYRXNWOOM-UHFFFAOYSA-N 0.000 description 1
WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-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 group O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 1
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
BCBHDSLDGBIFIX-UHFFFAOYSA-N 4-[(2-hydroxyethoxy)carbonyl]benzoic acid Chemical compound OCCOC(=O)C1=CC=C(C(O)=O)C=C1 BCBHDSLDGBIFIX-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
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FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
WJJGAKCAAJOICV-UHFFFAOYSA-N N-dimethyltyrosine Natural products CN(C)C(C(O)=O)CC1=CC=C(O)C=C1 WJJGAKCAAJOICV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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229910002661 O–Ti–O Inorganic materials 0.000 description 1
229910002655 O−Ti−O Inorganic materials 0.000 description 1
239000005643 Pelargonic acid Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910018557 Si O Inorganic materials 0.000 description 1
229910020175 SiOH Inorganic materials 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
229910007746 Zr—O Inorganic materials 0.000 description 1
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000006085 branching agent Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
239000006261 foam material Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000003607 modifier Substances 0.000 description 1
RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920000909 polytetrahydrofuran Polymers 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003755 zirconium compounds Chemical class 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
- 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
- C08G63/87—Non-metals or inter-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)
Inorganic Compounds Of Heavy Metals (AREA)

SK874-96A 1994-01-07 1994-12-28 Process for producing polyester and copolyester by using polycondensation of initial components creating polyester and use of the polycondensing catalysts SK87496A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4400300A DE4400300A1 (de)	1994-01-07	1994-01-07	Verfahren zur Herstellung von film- und faserbildenden Polyestern und Copolyestern
PCT/EP1994/004333 WO1995018839A1 (de)	1994-01-07	1995-01-02	Verfahren zur herstellung von polyestern und copolyestern

Publications (1)

Publication Number	Publication Date
SK87496A3 true SK87496A3 (en)	1997-04-09

Family

ID=6507556

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK874-96A SK87496A3 (en)	1994-01-07	1994-12-28	Process for producing polyester and copolyester by using polycondensation of initial components creating polyester and use of the polycondensing catalysts

Country Status (28)

Country	Link
US (1)	US5684116A (tr)
EP (1)	EP0738292B1 (tr)
JP (1)	JP3266265B2 (tr)
KR (1)	KR100341042B1 (tr)
CN (1)	CN1069662C (tr)
AT (1)	ATE207095T1 (tr)
AU (1)	AU685213B2 (tr)
BG (1)	BG63398B1 (tr)
BR (1)	BR9506428A (tr)
CA (1)	CA2179632A1 (tr)
CO (1)	CO4410247A1 (tr)
CZ (1)	CZ288250B6 (tr)
DE (2)	DE4400300A1 (tr)
ES (1)	ES2165413T3 (tr)
HR (1)	HRP941024A2 (tr)
HU (1)	HU214670B (tr)
MX (1)	MX9602662A (tr)
NZ (1)	NZ278069A (tr)
PL (2)	PL181186B1 (tr)
PT (1)	PT738292E (tr)
RU (1)	RU2151779C1 (tr)
SG (1)	SG70952A1 (tr)
SK (1)	SK87496A3 (tr)
TR (1)	TR28770A (tr)
TW (1)	TW393495B (tr)
UA (1)	UA41970C2 (tr)
WO (1)	WO1995018839A1 (tr)
ZA (1)	ZA9410366B (tr)

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US4421908A (en) *	1982-03-08	1983-12-20	Celanese Corporation	Preparation of polyesters by direct condensation of hydroxynaphthoic acids, aromatic diacids and aromatic diols
DE3370489D1 (en) *	1982-11-11	1987-04-30	Akzo Nv	Thermoplastic block copolyester resin composition containing a nucleating agent and an accelerator
FR2570077B1 (fr) *	1984-09-11	1987-05-29	Rhone Poulenc Films	Procede de preparation de polyester
DD279490A1 (de) *	1984-09-17	1990-06-06	Guben Chemiefaserwerk	Verfahren zur katalytischen herstellung von polyester
US5216109A (en) *	1990-08-22	1993-06-01	Teijin Limited	Crystalline wholly aromatic polyester, process for its production, resin composition containing it, and articles from the resin composition
IT1253357B (it) *	1991-01-25	1995-07-25	Montedipe Srl	Processo per la preparazione di poliesteri aromatici
US5143984A (en) *	1992-01-21	1992-09-01	Eastman Kodak Company	Process to prepare high molecule weight polyester
DE4400300A1 (de) *	1994-01-07	1995-07-13	Akzo Nobel Nv	Verfahren zur Herstellung von film- und faserbildenden Polyestern und Copolyestern

1994
- 1994-01-07 DE DE4400300A patent/DE4400300A1/de not_active Withdrawn
- 1994-12-23 CO CO94058158A patent/CO4410247A1/es unknown
- 1994-12-28 SK SK874-96A patent/SK87496A3/sk unknown
- 1994-12-28 ZA ZA9410366A patent/ZA9410366B/xx unknown
- 1994-12-29 TR TR01377/94A patent/TR28770A/tr unknown
- 1994-12-29 HR HRP4400300.5A patent/HRP941024A2/hr not_active Application Discontinuation
1995
- 1995-01-02 PL PL95342385A patent/PL181186B1/pl not_active IP Right Cessation
- 1995-01-02 WO PCT/EP1994/004333 patent/WO1995018839A1/de not_active Ceased
- 1995-01-02 EP EP95905605A patent/EP0738292B1/de not_active Expired - Lifetime
- 1995-01-02 CA CA002179632A patent/CA2179632A1/en not_active Abandoned
- 1995-01-02 NZ NZ278069A patent/NZ278069A/en unknown
- 1995-01-02 AU AU14156/95A patent/AU685213B2/en not_active Ceased
- 1995-01-02 SG SG1996000151A patent/SG70952A1/en unknown
- 1995-01-02 HU HU9601853A patent/HU214670B/hu not_active IP Right Cessation
- 1995-01-02 CN CN95191164A patent/CN1069662C/zh not_active Expired - Fee Related
- 1995-01-02 MX MX9602662A patent/MX9602662A/es unknown
- 1995-01-02 CZ CZ19961993A patent/CZ288250B6/cs not_active IP Right Cessation
- 1995-01-02 ES ES95905605T patent/ES2165413T3/es not_active Expired - Lifetime
- 1995-01-02 UA UA96072678A patent/UA41970C2/uk unknown
- 1995-01-02 KR KR1019960703627A patent/KR100341042B1/ko not_active Expired - Fee Related
- 1995-01-02 PT PT95905605T patent/PT738292E/pt unknown
- 1995-01-02 US US08/669,363 patent/US5684116A/en not_active Expired - Fee Related
- 1995-01-02 DE DE59509722T patent/DE59509722D1/de not_active Expired - Lifetime
- 1995-01-02 RU RU96117260/04A patent/RU2151779C1/ru not_active IP Right Cessation
- 1995-01-02 JP JP51830395A patent/JP3266265B2/ja not_active Expired - Fee Related
- 1995-01-02 PL PL95315746A patent/PL181123B1/pl not_active IP Right Cessation
- 1995-01-02 BR BR9506428A patent/BR9506428A/pt not_active IP Right Cessation
- 1995-01-02 AT AT95905605T patent/ATE207095T1/de not_active IP Right Cessation
- 1995-04-10 TW TW084103408A patent/TW393495B/zh not_active IP Right Cessation
1996
- 1996-07-26 BG BG100750A patent/BG63398B1/bg unknown

Also Published As

Publication number	Publication date
TR28770A (tr)	1997-02-28
ATE207095T1 (de)	2001-11-15
PT738292E (pt)	2002-04-29
CA2179632A1 (en)	1995-07-13
JPH09507514A (ja)	1997-07-29
BG100750A (bg)	1997-03-31
CN1138339A (zh)	1996-12-18
AU1415695A (en)	1995-08-01
CO4410247A1 (es)	1997-01-09
DE4400300A1 (de)	1995-07-13
AU685213B2 (en)	1998-01-15
ES2165413T3 (es)	2002-03-16
MX9602662A (es)	1997-05-31
HU9601853D0 (en)	1996-09-30
BG63398B1 (bg)	2001-12-29
HU214670B (hu)	1998-04-28
TW393495B (en)	2000-06-11
HRP941024A2 (en)	1997-10-31
US5684116A (en)	1997-11-04
JP3266265B2 (ja)	2002-03-18
DE59509722D1 (de)	2001-11-22
EP0738292B1 (de)	2001-10-17
KR100341042B1 (ko)	2002-11-29
WO1995018839A1 (de)	1995-07-13
HUT75491A (en)	1997-05-28
RU2151779C1 (ru)	2000-06-27
CZ199396A3 (en)	1997-02-12
EP0738292A1 (de)	1996-10-23
BR9506428A (pt)	1997-03-04
CZ288250B6 (en)	2001-05-16
PL315746A1 (en)	1996-11-25
PL181186B1 (pl)	2001-06-29
SG70952A1 (en)	2000-03-21
NZ278069A (en)	1998-01-26
CN1069662C (zh)	2001-08-15
ZA9410366B (en)	1995-09-01
PL181123B1 (pl)	2001-05-31
UA41970C2 (uk)	2001-10-15

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SK87496A3 (en)	1997-04-09	Process for producing polyester and copolyester by using polycondensation of initial components creating polyester and use of the polycondensing catalysts
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CN100413908C (zh)	2008-08-27	用于制造酯的催化剂
WO2001056694A1 (en)	2001-08-09	Esterification catalyst compositions
KR100372965B1 (ko)	2003-05-01	폴리에스테르및코폴리에스테르의제조방법
US3758535A (en)	1973-09-11	Process of reacting a silicon compound with a titanium compound
KR20070030730A (ko)	2007-03-16	에스테르 제조를 위한 촉매
MXPA99011497A (en)	2000-06-01	Method for producing polyesters and copolyesters