DE2713679A1 - Verfahren zur herstellung eines polyesters - Google Patents
Verfahren zur herstellung eines polyestersInfo
- Publication number
- DE2713679A1 DE2713679A1 DE19772713679 DE2713679A DE2713679A1 DE 2713679 A1 DE2713679 A1 DE 2713679A1 DE 19772713679 DE19772713679 DE 19772713679 DE 2713679 A DE2713679 A DE 2713679A DE 2713679 A1 DE2713679 A1 DE 2713679A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- compound
- acid
- monocarboxylic
- zirconium
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 229920000728 polyester Polymers 0.000 title description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000003054 catalyst Substances 0.000 claims description 46
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- -1 alkylene glycol Chemical compound 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 238000006068 polycondensation reaction Methods 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 20
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 19
- 229910052725 zinc Inorganic materials 0.000 claims description 19
- 239000011701 zinc Substances 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 238000005809 transesterification reaction Methods 0.000 claims description 18
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 17
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 17
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
- 229910052791 calcium Inorganic materials 0.000 claims description 10
- 239000011575 calcium Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000002334 glycols Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052726 zirconium Chemical class 0.000 claims description 8
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical class [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- FAWGZAFXDJGWBB-UHFFFAOYSA-N antimony(3+) Chemical class [Sb+3] FAWGZAFXDJGWBB-UHFFFAOYSA-N 0.000 claims description 6
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 150000002696 manganese Chemical class 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229920001283 Polyalkylene terephthalate Polymers 0.000 claims description 2
- TXTQARDVRPFFHL-UHFFFAOYSA-N [Sb].[H][H] Chemical class [Sb].[H][H] TXTQARDVRPFFHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 5
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical class [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 claims 4
- 125000000732 arylene group Chemical group 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 150000003754 zirconium Chemical class 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 229920001281 polyalkylene Polymers 0.000 claims 2
- TUEGREKNWIPDRA-UHFFFAOYSA-N [Ca].[Mn] Chemical class [Ca].[Mn] TUEGREKNWIPDRA-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 21
- 238000009835 boiling Methods 0.000 description 17
- 229910052787 antimony Inorganic materials 0.000 description 16
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000007790 solid phase Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000001757 thermogravimetry curve Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical class [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 8
- 229910052748 manganese Inorganic materials 0.000 description 8
- 239000011572 manganese Substances 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229940082328 manganese acetate tetrahydrate Drugs 0.000 description 4
- 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 4
- LYTNHSCLZRMKON-UHFFFAOYSA-L oxygen(2-);zirconium(4+);diacetate Chemical compound [O-2].[Zr+4].CC([O-])=O.CC([O-])=O LYTNHSCLZRMKON-UHFFFAOYSA-L 0.000 description 4
- 239000003352 sequestering agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- DJTZIDSZSYWGKR-UHFFFAOYSA-N acetic acid tetrahydrate Chemical compound O.O.O.O.CC(O)=O DJTZIDSZSYWGKR-UHFFFAOYSA-N 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000001627 detrimental effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XQKKWWCELHKGKB-UHFFFAOYSA-L calcium acetate monohydrate Chemical compound O.[Ca+2].CC([O-])=O.CC([O-])=O XQKKWWCELHKGKB-UHFFFAOYSA-L 0.000 description 2
- 229940067460 calcium acetate monohydrate Drugs 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 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 2
- 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
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000289581 Macropus sp. Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001462 antimony Chemical class 0.000 description 1
- HMJCIIKLTQFEEN-UHFFFAOYSA-N antimony calcium Chemical compound [Ca].[Sb] HMJCIIKLTQFEEN-UHFFFAOYSA-N 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- OOBNORVQFIAGPT-UHFFFAOYSA-N antimony manganese Chemical compound [Mn].[Sb] OOBNORVQFIAGPT-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 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 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- YGBFTDQFAKDXBZ-UHFFFAOYSA-N tributyl stiborite Chemical compound [Sb+3].CCCC[O-].CCCC[O-].CCCC[O-] YGBFTDQFAKDXBZ-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- CPRNXYUBUMWONV-UHFFFAOYSA-N zinc butan-1-olate zirconium(4+) Chemical compound [Zn+2].[Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] CPRNXYUBUMWONV-UHFFFAOYSA-N 0.000 description 1
- ZRLVQXXKMXINBN-UHFFFAOYSA-N zinc zirconium(4+) Chemical compound [Zn+2].[Zr+4] ZRLVQXXKMXINBN-UHFFFAOYSA-N 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
- C08G63/83—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
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 |
|---|---|---|---|
| US05/670,654 US4122107A (en) | 1976-03-26 | 1976-03-26 | Reaction products of specific antimony compounds with a carboxylate of zinc calcium or manganese and an alcohol or glycol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2713679A1 true DE2713679A1 (de) | 1977-09-29 |
Family
ID=24691286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772713679 Withdrawn DE2713679A1 (de) | 1976-03-26 | 1977-03-28 | Verfahren zur herstellung eines polyesters |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4122107A (enExample) |
| JP (1) | JPS52125596A (enExample) |
| AU (1) | AU504820B2 (enExample) |
| BR (1) | BR7701865A (enExample) |
| CA (1) | CA1076128A (enExample) |
| DE (1) | DE2713679A1 (enExample) |
| ES (2) | ES457171A1 (enExample) |
| FR (1) | FR2345211A1 (enExample) |
| GB (1) | GB1535476A (enExample) |
| IT (1) | IT1081332B (enExample) |
| NL (1) | NL7702860A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0083746A1 (en) * | 1981-12-12 | 1983-07-20 | Toyo Boseki Kabushiki Kaisha | Biaxially stretched polyester films |
| DE102008044487A1 (de) * | 2008-08-29 | 2010-03-04 | Lurgi Zimmer Gmbh | Verfahren zur Herstellung von Polymeren mit neutralem Farbton |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2537593B1 (fr) * | 1982-12-10 | 1986-04-11 | Raffinage Cie Francaise | Compositions organometalliques mixtes comprenant des elements des groupes du fer et des lanthanides, procede de preparation et application desdites compositions comme additifs pour combustibles ou carburants |
| US4785060A (en) * | 1986-08-28 | 1988-11-15 | Colgate-Palmolive Company | Soil release promoting pet-poet copolymer, method of producing same and use thereof in detergent composition having soil release promoting property |
| US5166311A (en) * | 1989-05-22 | 1992-11-24 | Hoechst Celanese Corporation | Catalyst system and process for preparing high clarity, colorless polyethylene terephthalate |
| US5008230A (en) * | 1989-05-22 | 1991-04-16 | Hoechst Celanese Corporation | Catalyst for preparing high clarity, colorless polyethylene terephthalate |
| US5162488A (en) * | 1989-05-22 | 1992-11-10 | 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 |
| US5852164A (en) * | 1996-04-16 | 1998-12-22 | Mitsubishi Chemical Corporation | Polyester, process for producing the same and molding product therefrom |
| EP0864596A1 (en) * | 1997-03-14 | 1998-09-16 | Hoechst Diafoil GmbH | Process for the production of polyethylene terephthalate |
| AU2077601A (en) * | 1999-12-10 | 2001-06-18 | Dow Global Technologies Inc. | Catalyst systems for polycondensation reactions |
| KR20030084183A (ko) * | 2002-04-25 | 2003-11-01 | 켐엔텍 주식회사 | 폴리에스테르의 제조방법 |
| WO2004014982A2 (en) | 2002-05-09 | 2004-02-19 | Equipolymers Gmbh | Catalyst systems for polycondensation reactions |
| GB0305817D0 (en) * | 2003-03-13 | 2003-04-16 | Ic Innovations Ltd | Polymerisation initiators |
| ATE382066T1 (de) * | 2004-05-05 | 2008-01-15 | Saudi Basic Ind Corp | Verfahren zur herstellung von copolyestern aus polyethylenterephthalat |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1307860A (en) * | 1919-06-24 | Seymour m | ||
| BE365818A (enExample) * | 1928-11-30 | |||
| US2281735A (en) * | 1939-10-20 | 1942-05-05 | Stauffer Chemical Co | Dusting composition |
| US2720504A (en) * | 1952-10-03 | 1955-10-11 | Eastman Kodak Co | Organo-metallic zirconium catalysts for the preparation of polyesters |
| BE536161A (enExample) * | 1954-03-02 | |||
| US2892782A (en) * | 1955-08-29 | 1959-06-30 | Texaco Inc | Mixtures of metal salts of organic hydroxy compounds |
| GB828707A (en) * | 1956-05-18 | 1960-02-24 | British Celanese | Improvements in the manufacture of high linear polyesters |
| US2927870A (en) * | 1956-08-28 | 1960-03-08 | Dow Corning | Zirconium acetate-zinc acetate catalyzed organohydrogenosiloxane emulsions and the treatment of fabrics therewith |
| NL256567A (enExample) * | 1959-10-06 | |||
| NL302660A (enExample) * | 1962-12-24 | 1900-01-01 | ||
| GB1058395A (en) * | 1964-05-20 | 1967-02-08 | Hardman & Holden Ltd | Improvements relating to zirconium compounds |
| GB1138332A (en) * | 1965-02-11 | 1969-01-01 | United States Borax Chem | Arsenic and antimony derivatives |
| FR1478334A (fr) * | 1965-05-06 | 1967-04-28 | Inst Francais Du Petrole | Catalyseur à base de métaux bivalents, sa préparation et ses applications, en particulier pour la polymérisation d'éthers cycliques |
| US3415860A (en) * | 1966-03-18 | 1968-12-10 | Monsanto Co | Preparation of antimony triacetate |
| US3484410A (en) * | 1966-11-23 | 1969-12-16 | Allied Chem | Process for preparing polyesters with antimony catalysts |
| FR1542470A (fr) | 1966-12-02 | 1968-10-18 | Inst Francais Du Petrole | Nouveaux catalyseurs de polymérisation d'oxydes d'alcoylènes |
| GB1284658A (en) * | 1969-05-02 | 1972-08-09 | Goodyear Tire & Rubber | Improved process for the preparation of polyesters |
| US3624049A (en) * | 1969-06-23 | 1971-11-30 | M & T Chemicals Inc | The preparation of poly (ethylene terephthalate) using trivalent antimony compounds as catalysts |
| US3705133A (en) * | 1969-08-21 | 1972-12-05 | Allied Chem | Polyester process |
| US3873451A (en) * | 1970-11-30 | 1975-03-25 | Du Pont | Flame retardant antimony compounds |
| US3836557A (en) * | 1971-12-03 | 1974-09-17 | Du Pont | Salts of antimony (v) esters as flame retardants |
| US3899522A (en) * | 1973-08-24 | 1975-08-12 | Nl Industries Inc | Trivalent antimony catalyst |
-
1976
- 1976-03-26 US US05/670,654 patent/US4122107A/en not_active Expired - Lifetime
-
1977
- 1977-01-21 US US05/761,338 patent/US4104263A/en not_active Expired - Lifetime
- 1977-03-04 GB GB9267/77A patent/GB1535476A/en not_active Expired
- 1977-03-08 AU AU23012/77A patent/AU504820B2/en not_active Expired
- 1977-03-16 NL NL7702860A patent/NL7702860A/xx not_active Application Discontinuation
- 1977-03-23 CA CA274,538A patent/CA1076128A/en not_active Expired
- 1977-03-24 FR FR7708844A patent/FR2345211A1/fr active Granted
- 1977-03-24 ES ES457171A patent/ES457171A1/es not_active Expired
- 1977-03-24 IT IT09385/77A patent/IT1081332B/it active
- 1977-03-25 JP JP3231077A patent/JPS52125596A/ja active Pending
- 1977-03-25 BR BR7701865A patent/BR7701865A/pt unknown
- 1977-03-28 DE DE19772713679 patent/DE2713679A1/de not_active Withdrawn
-
1978
- 1978-05-02 ES ES469365A patent/ES469365A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0083746A1 (en) * | 1981-12-12 | 1983-07-20 | Toyo Boseki Kabushiki Kaisha | Biaxially stretched polyester films |
| DE102008044487A1 (de) * | 2008-08-29 | 2010-03-04 | Lurgi Zimmer Gmbh | Verfahren zur Herstellung von Polymeren mit neutralem Farbton |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1081332B (it) | 1985-05-21 |
| JPS52125596A (en) | 1977-10-21 |
| NL7702860A (nl) | 1977-09-28 |
| ES457171A1 (es) | 1978-08-16 |
| GB1535476A (en) | 1978-12-13 |
| CA1076128A (en) | 1980-04-22 |
| ES469365A1 (es) | 1978-11-16 |
| US4122107A (en) | 1978-10-24 |
| FR2345211B1 (enExample) | 1982-02-19 |
| AU2301277A (en) | 1978-09-14 |
| BR7701865A (pt) | 1977-11-08 |
| FR2345211A1 (fr) | 1977-10-21 |
| AU504820B2 (en) | 1979-11-01 |
| US4104263A (en) | 1978-08-01 |
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