CA1081675A - Procede et systemes catalyseur-inhibiteur pour la preparation de polyesters lineaires synthetiques - Google Patents

Procede et systemes catalyseur-inhibiteur pour la preparation de polyesters lineaires synthetiques

Info

Publication number: CA1081675A
Authority: CA; Canada
Prior art keywords: manganese; ester; phosphate; antimony; amount
Prior art date: 1976-03-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA271,069A

Other languages

English (en)

Inventor

Nicholas C. Russin

Ronald A. Tershansy

Charles J. Kibler

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eastman Kodak Co

Original Assignee

Eastman Kodak Co

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.)

1976-03-01

Filing date

1977-02-04

Publication date

1980-07-15

1976-03-01 Priority claimed from US05/662,672 external-priority patent/US4010145A/en

1977-02-04 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1980-07-15 Application granted granted Critical

1980-07-15 Publication of CA1081675A publication Critical patent/CA1081675A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 39
229920000728 polyester Polymers 0.000 title claims abstract description 31
230000008569 process Effects 0.000 title claims description 24
239000003060 catalysis inhibitor Substances 0.000 title abstract description 13
-1 titanium alkoxides Chemical class 0.000 claims abstract description 91
239000010936 titanium Substances 0.000 claims abstract description 65
229910019142 PO4 Inorganic materials 0.000 claims abstract description 51
239000010452 phosphate Substances 0.000 claims abstract description 50
239000011572 manganese Substances 0.000 claims abstract description 49
238000004519 manufacturing process Methods 0.000 claims abstract description 25
229910052719 titanium Inorganic materials 0.000 claims abstract description 20
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical class [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 16
229910052748 manganese Inorganic materials 0.000 claims abstract description 15
239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 15
150000001463 antimony compounds Chemical class 0.000 claims abstract description 14
229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 14
239000010941 cobalt Chemical class 0.000 claims abstract description 9
229910017052 cobalt Chemical class 0.000 claims abstract description 9
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical class [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 101
150000002148 esters Chemical class 0.000 claims description 51
235000021317 phosphate Nutrition 0.000 claims description 50
239000003054 catalyst Substances 0.000 claims description 49
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 48
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 27
229910052751 metal Inorganic materials 0.000 claims description 26
239000002184 metal Substances 0.000 claims description 26
229910052787 antimony Inorganic materials 0.000 claims description 17
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 17
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
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 claims description 14
239000007795 chemical reaction product Substances 0.000 claims description 12
230000000694 effects Effects 0.000 claims description 11
150000002696 manganese Chemical class 0.000 claims description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
239000000061 acid fraction Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000001868 cobalt Chemical class 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004437 phosphorous atom Chemical group 0.000 claims description 7
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 6
AHALDBHNNHQQGN-UHFFFAOYSA-N benzoic acid;tetrahydrate Chemical compound O.O.O.O.OC(=O)C1=CC=CC=C1 AHALDBHNNHQQGN-UHFFFAOYSA-N 0.000 claims description 6
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 claims description 6
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical group [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 6
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 claims description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
229910052698 phosphorus Inorganic materials 0.000 claims description 5
239000011574 phosphorus Substances 0.000 claims description 5
UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
GIMXAEZBXRIECN-UHFFFAOYSA-J 2-hydroxyacetate;titanium(4+) Chemical class [Ti+4].OCC([O-])=O.OCC([O-])=O.OCC([O-])=O.OCC([O-])=O GIMXAEZBXRIECN-UHFFFAOYSA-J 0.000 claims description 3
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 3
229910021380 Manganese Chloride Inorganic materials 0.000 claims description 3
GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 3
150000001462 antimony Chemical class 0.000 claims 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 claims description 3
UNRVMLDKEXPNDG-UHFFFAOYSA-N butanedioic acid;manganese Chemical compound [Mn].OC(=O)CCC(O)=O UNRVMLDKEXPNDG-UHFFFAOYSA-N 0.000 claims description 3
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 3
JTGXMEBOJMMMSH-UHFFFAOYSA-N cobalt;(2-hydroxyphenyl)methyl 2-hydroxybenzoate Chemical compound [Co].OC1=CC=CC=C1COC(=O)C1=CC=CC=C1O JTGXMEBOJMMMSH-UHFFFAOYSA-N 0.000 claims description 3
FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 claims description 3
229940097267 cobaltous chloride Drugs 0.000 claims description 3
229940045032 cobaltous nitrate Drugs 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
229940051250 hexylene glycol Drugs 0.000 claims description 3
150000004679 hydroxides Chemical class 0.000 claims description 3
229940071125 manganese acetate Drugs 0.000 claims description 3
239000011565 manganese chloride Substances 0.000 claims description 3
229940099607 manganese chloride Drugs 0.000 claims description 3
235000002867 manganese chloride Nutrition 0.000 claims description 3
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 3
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [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 claims description 3
SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 claims description 3
229910001092 metal group alloy Inorganic materials 0.000 claims description 3
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 claims description 3
TWHXWYVOWJCXSI-UHFFFAOYSA-N phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O TWHXWYVOWJCXSI-UHFFFAOYSA-N 0.000 claims description 3
VGWDZDOVIHVYBQ-UHFFFAOYSA-N (2-hydroxyphenyl)methyl 2-hydroxybenzoate;manganese Chemical compound [Mn].OC1=CC=CC=C1COC(=O)C1=CC=CC=C1O VGWDZDOVIHVYBQ-UHFFFAOYSA-N 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 claims description 2
HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 claims 2
WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 claims 2
150000003568 thioethers Chemical class 0.000 claims 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
229960000953 salsalate Drugs 0.000 claims 1
239000000835 fiber Substances 0.000 abstract description 4
238000006116 polymerization reaction Methods 0.000 abstract description 3
229920000642 polymer Polymers 0.000 description 45
239000000243 solution Substances 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 25
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000006068 polycondensation reaction Methods 0.000 description 19
239000000047 product Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
238000004043 dyeing Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000000975 dye Substances 0.000 description 6
YIHQSMBNBPAEJC-UHFFFAOYSA-L manganese(2+);dibenzoate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YIHQSMBNBPAEJC-UHFFFAOYSA-L 0.000 description 6
GKMVCDATACEPQS-UHFFFAOYSA-L O.O.O.[Co+2].CC([O-])=O.CC([O-])=O Chemical compound O.O.O.[Co+2].CC([O-])=O.CC([O-])=O GKMVCDATACEPQS-UHFFFAOYSA-L 0.000 description 5
239000011701 zinc Substances 0.000 description 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
230000003301 hydrolyzing effect Effects 0.000 description 4
239000008188 pellet Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000004744 fabric Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
230000001105 regulatory effect Effects 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
230000004580 weight loss Effects 0.000 description 3
239000004971 Cross linker Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
239000000654 additive Substances 0.000 description 2
239000001000 anthraquinone dye Substances 0.000 description 2
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 2
239000011575 calcium Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000009998 heat setting Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
IAQLJCYTGRMXMA-UHFFFAOYSA-M lithium;acetate;dihydrate Chemical compound [Li+].O.O.CC([O-])=O IAQLJCYTGRMXMA-UHFFFAOYSA-M 0.000 description 2
UMDUWSQLUFPGLC-UHFFFAOYSA-N magnesium butan-1-olate titanium(4+) Chemical compound [O-]CCCC.[Ti+4].[Mg+2].[O-]CCCC.[O-]CCCC.[O-]CCCC.[O-]CCCC.[O-]CCCC UMDUWSQLUFPGLC-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000013014 purified material Substances 0.000 description 2
230000005855 radiation Effects 0.000 description 2
230000000191 radiation effect Effects 0.000 description 2
230000000007 visual effect Effects 0.000 description 2
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
VOCYGZAHYQXJOF-UHFFFAOYSA-N 1,8-dihydroxy-4-[4-(2-hydroxyethyl)anilino]-5-nitroanthracene-9,10-dione Chemical compound C1=CC(CCO)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=C([N+]([O-])=O)C=CC(O)=C1C2=O VOCYGZAHYQXJOF-UHFFFAOYSA-N 0.000 description 1
RQLMZSLFKGNXTO-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(6-hydroxyhexoxy)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(OCCCCCCO)=C2N RQLMZSLFKGNXTO-UHFFFAOYSA-N 0.000 description 1
MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 1
KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 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
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 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910014130 Na—P Inorganic materials 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000008030 elimination Effects 0.000 description 1
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239000012362 glacial acetic acid Substances 0.000 description 1
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150000002367 halogens Chemical class 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
QMZIDZZDMPWRHM-UHFFFAOYSA-L manganese(2+);dibenzoate Chemical compound [Mn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 QMZIDZZDMPWRHM-UHFFFAOYSA-L 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical compound [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-UHFFFAOYSA-N 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
230000037048 polymerization activity Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
FHWAGNWFJRJDBG-UHFFFAOYSA-N trimagnesium distiborate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-][Sb]([O-])([O-])=O.[O-][Sb]([O-])([O-])=O FHWAGNWFJRJDBG-UHFFFAOYSA-N 0.000 description 1
NSBGJRFJIJFMGW-UHFFFAOYSA-N trisodium;stiborate Chemical compound [Na+].[Na+].[Na+].[O-][Sb]([O-])([O-])=O NSBGJRFJIJFMGW-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1
YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 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

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)
Artificial Filaments (AREA)

CA271,069A 1976-03-01 1977-02-04 Procede et systemes catalyseur-inhibiteur pour la preparation de polyesters lineaires synthetiques Expired CA1081675A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/662,672 US4010145A (en)	1975-05-12	1976-03-01	Process and catalyst inhibitor systems for preparing synthetic linear polyesters
US662,672		1976-03-01

Publications (1)

Publication Number	Publication Date
CA1081675A true CA1081675A (fr)	1980-07-15

Family

ID=24658694

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA271,069A Expired CA1081675A (fr)	1976-03-01	1977-02-04	Procede et systemes catalyseur-inhibiteur pour la preparation de polyesters lineaires synthetiques

Country Status (6)

Country	Link
JP (1)	JPS52105591A (fr)
CA (1)	CA1081675A (fr)
DE (1)	DE2707832A1 (fr)
FR (1)	FR2343011A1 (fr)
GB (1)	GB1569799A (fr)
IT (1)	IT1113758B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5153164A (en) *	1989-05-22	1992-10-06	Hoechst Celanese Corporation	Catalyst system for preparing polyethylene terephthalate
KR100343406B1 (ko) *	1997-09-03	2002-07-11	야마모토 카즈모토	폴리에스테르 수지 조성물
US7358322B2 (en)	2004-03-09	2008-04-15	Eastman Chemical Company	High IV melt phase polyester polymer catalyzed with antimony containing compounds
US8557950B2 (en)	2005-06-16	2013-10-15	Grupo Petrotemex, S.A. De C.V.	High intrinsic viscosity melt phase polyester polymers with acceptable acetaldehyde generation rates

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1424811A (fr) *	1965-02-16	1966-01-14	Schwarza Chemiefaser	Procédé de fabrication de fils, fibres, feuilles et corps analogues à partir de polyesters et de polyesters mixtes linéaires

1977
- 1977-02-04 CA CA271,069A patent/CA1081675A/fr not_active Expired
- 1977-02-23 DE DE19772707832 patent/DE2707832A1/de not_active Withdrawn
- 1977-02-28 JP JP2143177A patent/JPS52105591A/ja active Pending
- 1977-03-01 GB GB858877A patent/GB1569799A/en not_active Expired
- 1977-03-01 FR FR7705889A patent/FR2343011A1/fr active Granted
- 1977-03-01 IT IT2080677A patent/IT1113758B/it active

Also Published As

Publication number	Publication date
FR2343011B1 (fr)	1984-06-08
DE2707832A1 (de)	1977-09-08
JPS52105591A (en)	1977-09-05
FR2343011A1 (fr)	1977-09-30
GB1569799A (en)	1980-06-18
IT1113758B (it)	1986-01-20

Legal Events

Date	Code	Title	Description
1997-07-15	MKEX	Expiry

Publication	Publication Date	Title
US4010145A (en)	1977-03-01	Process and catalyst inhibitor systems for preparing synthetic linear polyesters
US3962189A (en)	1976-06-08	Process and catalyst-inhibitor systems for preparing synthetic linear polyesters
US3907754A (en)	1975-09-23	Process and catalyst-inhibitor system for preparing synthetic linear polyester
US2720507A (en)	1955-10-11	Organo-metallic tin catalysts for preparation of polyesters
US5017680A (en)	1991-05-21	Process and catalyst-inhibitor systems for preparing poly(ethylene terephthalate)
CA1057734A (fr)	1979-07-03	Procede et systeme catalyseur-inhibiteur pour la preparation de polyesters synthetiques a chaines lineaires
US4501878A (en)	1985-02-26	Process for the preparation of high molecular weight polyesters
US3594347A (en)	1971-07-20	Polyesters containing aryl phosphinates
EP1384740A1 (fr)	2004-01-28	Procede de preparation de copolyesters d'acide terephtalique, d'ethylene glycol et de 1,4-cyclohexandimethanol de coloration neutre, tres clairs et a degre de blancheur accru
US4156072A (en)	1979-05-22	Coordination complexes as polyesterification catalysts
US3528946A (en)	1970-09-15	Acetylacetonates as polycondensation catalysts in transesterification method of preparing polyesters
WO2002057335A1 (fr)	2002-07-25	Catalyseur de polymerisation de polyester, polyester et procede de fabrication de celui-ci
US4104263A (en)	1978-08-01	Process for producing film and fiber-forming polyalkylene terephthalate
US3060152A (en)	1962-10-23	Process for preparing polyesters from aromatic dicarboxylic acids and polymethylene glycols in the presence of certain tertiary amines
CA1081675A (fr)	1980-07-15	Procede et systemes catalyseur-inhibiteur pour la preparation de polyesters lineaires synthetiques
US3444139A (en)	1969-05-13	Preparation of highly polymeric polyesters in the presence of catalytic titanium compounds containing ester groups
JPH0925337A (ja)	1997-01-28	ポリ（エチレンテレフタレート）合成用高活性触媒系
US3927052A (en)	1975-12-16	Catalyst
US3852247A (en)	1974-12-03	Polymerization catalyst
US4116942A (en)	1978-09-26	Process for catalytic production of polyesters
US2711402A (en)	1955-06-21	Aluminates as ester-interchange catalysts in making polyesters
US2956985A (en)	1960-10-18	Metal salts of dithiocarbamic acids as catalysts in the production of polyesters
USRE30554E (en)	1981-03-24	Coordination complexes as catalysts
US3057826A (en)	1962-10-09	Copolyesters having carboxylate salt groups
US3385830A (en)	1968-05-28	Process for manufacturing polyethylene terephthalate employing metal salts of halogenated haliphatic acids