CA1057734A - Procede et systeme catalyseur-inhibiteur pour la preparation de polyesters synthetiques a chaines lineaires - Google Patents

Procede et systeme catalyseur-inhibiteur pour la preparation de polyesters synthetiques a chaines lineaires

Info

Publication number: CA1057734A
Authority: CA; Canada
Prior art keywords: manganese; acetate; benzoate; lithium; acetylacetonate
Prior art date: 1974-11-01
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

CA236,847A

Other languages

English (en)

Other versions

CA236847S (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.)

1974-11-01

Filing date

1975-10-01

Publication date

1979-07-03

1975-10-01 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1976-03-01 Priority to US05/662,672 priority Critical patent/US4010145A/en

1979-07-03 Application granted granted Critical

1979-07-03 Publication of CA1057734A publication Critical patent/CA1057734A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 30
229920000728 polyester Polymers 0.000 title claims description 29
239000003060 catalysis inhibitor Substances 0.000 title description 3
-1 titanium alkoxides Chemical class 0.000 claims abstract description 71
239000003054 catalyst Substances 0.000 claims abstract description 48
239000010936 titanium Substances 0.000 claims abstract description 44
239000011572 manganese Substances 0.000 claims abstract description 36
229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 18
229910052719 titanium Inorganic materials 0.000 claims abstract description 18
239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 16
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical class [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052784 alkaline earth metal Chemical class 0.000 claims abstract description 14
229910052748 manganese Inorganic materials 0.000 claims abstract description 14
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 13
150000001340 alkali metals Chemical class 0.000 claims abstract description 12
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 12
239000010941 cobalt Chemical class 0.000 claims abstract description 7
229910017052 cobalt Chemical class 0.000 claims abstract description 7
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical class [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 82
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 59
229910019142 PO4 Inorganic materials 0.000 claims description 42
235000021317 phosphate Nutrition 0.000 claims description 42
239000010452 phosphate Substances 0.000 claims description 41
150000002148 esters Chemical class 0.000 claims description 32
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 22
235000002908 manganese Nutrition 0.000 claims description 13
229910052751 metal Inorganic materials 0.000 claims description 12
239000002184 metal Substances 0.000 claims description 12
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 12
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
150000002696 manganese Chemical class 0.000 claims description 8
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
239000000061 acid fraction Substances 0.000 claims description 7
150000001868 cobalt Chemical class 0.000 claims description 7
ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical group O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 claims description 7
229910052744 lithium Inorganic materials 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 6
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-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
230000000694 effects Effects 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
239000011777 magnesium Substances 0.000 claims description 6
229910052700 potassium Inorganic materials 0.000 claims description 6
239000011591 potassium Substances 0.000 claims description 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 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 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
239000011575 calcium Substances 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
125000004437 phosphorous atom Chemical group 0.000 claims description 4
239000001632 sodium acetate Substances 0.000 claims description 4
235000017281 sodium acetate Nutrition 0.000 claims description 4
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 3
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 description 3
RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 claims description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 claims description 3
DJHZYHWLGNJISM-FDGPNNRMSA-L barium(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ba+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O DJHZYHWLGNJISM-FDGPNNRMSA-L 0.000 claims description 3
HFAQXXPQBRIXGD-UHFFFAOYSA-L barium(2+);butanedioate Chemical compound [Ba+2].[O-]C(=O)CCC([O-])=O HFAQXXPQBRIXGD-UHFFFAOYSA-L 0.000 claims description 3
MJIAXOYYJWECDI-UHFFFAOYSA-L barium(2+);dibenzoate Chemical compound [Ba+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 MJIAXOYYJWECDI-UHFFFAOYSA-L 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
229910052791 calcium Inorganic materials 0.000 claims description 3
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 3
239000001639 calcium acetate Substances 0.000 claims description 3
235000011092 calcium acetate Nutrition 0.000 claims description 3
229960005147 calcium acetate Drugs 0.000 claims description 3
239000004301 calcium benzoate Substances 0.000 claims description 3
235000010237 calcium benzoate Nutrition 0.000 claims description 3
QAZYYQMPRQKMAC-FDGPNNRMSA-L calcium;(z)-4-oxopent-2-en-2-olate Chemical compound [Ca+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O QAZYYQMPRQKMAC-FDGPNNRMSA-L 0.000 claims description 3
PBUBJNYXWIDFMU-UHFFFAOYSA-L calcium;butanedioate Chemical compound [Ca+2].[O-]C(=O)CCC([O-])=O PBUBJNYXWIDFMU-UHFFFAOYSA-L 0.000 claims description 3
HZQXCUSDXIKLGS-UHFFFAOYSA-L calcium;dibenzoate;trihydrate Chemical compound O.O.O.[Ca+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HZQXCUSDXIKLGS-UHFFFAOYSA-L 0.000 claims description 3
JHLCADGWXYCDQA-UHFFFAOYSA-N calcium;ethanolate Chemical compound [Ca+2].CC[O-].CC[O-] JHLCADGWXYCDQA-UHFFFAOYSA-N 0.000 claims description 3
AMJQWGIYCROUQF-UHFFFAOYSA-N calcium;methanolate Chemical compound [Ca+2].[O-]C.[O-]C AMJQWGIYCROUQF-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
230000003197 catalytic effect Effects 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
UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 claims description 3
BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 claims description 3
CVOQYKPWIVSMDC-UHFFFAOYSA-L dipotassium;butanedioate Chemical compound [K+].[K+].[O-]C(=O)CCC([O-])=O CVOQYKPWIVSMDC-UHFFFAOYSA-L 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229940051250 hexylene glycol Drugs 0.000 claims description 3
229960001078 lithium Drugs 0.000 claims description 3
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 3
229940071257 lithium acetate Drugs 0.000 claims description 3
229940031993 lithium benzoate Drugs 0.000 claims description 3
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 claims description 3
WAHQBNXSPALNEA-UHFFFAOYSA-L lithium succinate Chemical compound [Li+].[Li+].[O-]C(=O)CCC([O-])=O WAHQBNXSPALNEA-UHFFFAOYSA-L 0.000 claims description 3
229960004254 lithium succinate Drugs 0.000 claims description 3
IAQLJCYTGRMXMA-UHFFFAOYSA-M lithium;acetate;dihydrate Chemical compound [Li+].O.O.CC([O-])=O IAQLJCYTGRMXMA-UHFFFAOYSA-M 0.000 claims description 3
LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 claims description 3
AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 claims description 3
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 claims description 3
239000011654 magnesium acetate Substances 0.000 claims description 3
235000011285 magnesium acetate Nutrition 0.000 claims description 3
229940069446 magnesium acetate Drugs 0.000 claims description 3
PJJZFXPJNUVBMR-UHFFFAOYSA-L magnesium benzoate Chemical compound [Mg+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 PJJZFXPJNUVBMR-UHFFFAOYSA-L 0.000 claims description 3
AKTIAGQCYPCKFX-FDGPNNRMSA-L magnesium;(z)-4-oxopent-2-en-2-olate Chemical compound [Mg+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AKTIAGQCYPCKFX-FDGPNNRMSA-L 0.000 claims description 3
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 claims description 3
229940071125 manganese acetate Drugs 0.000 claims description 3
239000011565 manganese chloride Substances 0.000 claims description 3
235000002867 manganese chloride Nutrition 0.000 claims description 3
229940099607 manganese chloride Drugs 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
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
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
235000011056 potassium acetate Nutrition 0.000 claims description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
239000004300 potassium benzoate Substances 0.000 claims description 3
235000010235 potassium benzoate Nutrition 0.000 claims description 3
229940103091 potassium benzoate Drugs 0.000 claims description 3
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 3
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 3
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 3
239000004299 sodium benzoate Substances 0.000 claims description 3
235000010234 sodium benzoate Nutrition 0.000 claims description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
229940074404 sodium succinate Drugs 0.000 claims description 3
ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 claims description 3
AIWZOHBYSFSQGV-LNKPDPKZSA-M sodium;(z)-4-oxopent-2-en-2-olate Chemical compound [Na+].C\C([O-])=C\C(C)=O AIWZOHBYSFSQGV-LNKPDPKZSA-M 0.000 claims description 3
KEPTYGWAYFIRNU-UHFFFAOYSA-N sodium;2-hydroxyethanolate Chemical compound [Na+].OCC[O-] KEPTYGWAYFIRNU-UHFFFAOYSA-N 0.000 claims description 3
OKUCEQDKBKYEJY-UHFFFAOYSA-N tert-butyl 3-(methylamino)pyrrolidine-1-carboxylate Chemical compound CNC1CCN(C(=O)OC(C)(C)C)C1 OKUCEQDKBKYEJY-UHFFFAOYSA-N 0.000 claims description 3
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 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 claims description 2
ZEZNFXXLELDHHV-UHFFFAOYSA-M C(CO)(=O)[O-].[Ti+4].CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] Chemical class C(CO)(=O)[O-].[Ti+4].CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] ZEZNFXXLELDHHV-UHFFFAOYSA-M 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 14
239000000835 fiber Substances 0.000 abstract description 4
239000003381 stabilizer Substances 0.000 abstract description 4
150000003014 phosphoric acid esters Chemical class 0.000 abstract description 3
238000006116 polymerization reaction Methods 0.000 abstract description 2
229920000642 polymer Polymers 0.000 description 32
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
238000006068 polycondensation reaction Methods 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
239000000047 product Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
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
239000002904 solvent Substances 0.000 description 6
238000004043 dyeing Methods 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
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 4
230000004580 weight loss Effects 0.000 description 4
239000011701 zinc Substances 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000000975 dye Substances 0.000 description 3
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 3
150000002739 metals Chemical class 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
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 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
229960000583 acetic acid Drugs 0.000 description 2
239000001000 anthraquinone dye Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000004744 fabric Substances 0.000 description 2
238000009998 heat setting Methods 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
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 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000008188 pellet Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000013014 purified material Substances 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
238000011282 treatment Methods 0.000 description 2
230000000007 visual effect Effects 0.000 description 2
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
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
241000282326 Felis catus Species 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
229910006710 Li—P Inorganic materials 0.000 description 1
229910014130 Na—P Inorganic materials 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229940011182 cobalt acetate Drugs 0.000 description 1
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000001465 metallisation Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-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
BEAZKUGSCHFXIQ-UHFFFAOYSA-L zinc;diacetate;dihydrate Chemical compound O.O.[Zn+2].CC([O-])=O.CC([O-])=O BEAZKUGSCHFXIQ-UHFFFAOYSA-L 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)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA236,847A 1974-11-01 1975-10-01 Procede et systeme catalyseur-inhibiteur pour la preparation de polyesters synthetiques a chaines lineaires Expired CA1057734A (fr)

Priority Applications (1)

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

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US51995374A	1974-11-01	1974-11-01

Publications (1)

Publication Number	Publication Date
CA1057734A true CA1057734A (fr)	1979-07-03

Family

ID=24070560

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA236,847A Expired CA1057734A (fr)	1974-11-01	1975-10-01	Procede et systeme catalyseur-inhibiteur pour la preparation de polyesters synthetiques a chaines lineaires

Country Status (6)

Country	Link
JP (1)	JPS5168489A (fr)
CA (1)	CA1057734A (fr)
DE (1)	DE2548630A1 (fr)
FR (1)	FR2289524A1 (fr)
GB (1)	GB1522656A (fr)
IT (1)	IT1044090B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2637814A1 (de) *	1976-08-21	1978-02-23	Bayer Ag	Verfahren zur herstellung hochmolekularer polyester
DE2637813A1 (de) *	1976-08-21	1978-02-23	Bayer Ag	Verfahren zur herstellung hochmolekularer polyester
US5019640A (en) *	1989-10-23	1991-05-28	Hoechst Celanese Corporation	Producing a polyethylene terephthalate based polymer from a lower dialkyl ester of a dicarboxylic acid and a glycol
US5101008A (en) *	1990-03-07	1992-03-31	Hoechst Celanese Corporation	Producing a copolyester from two lower dialkyl esters of dicarboxylic acid and a glycol
US4990594A (en) *	1990-03-07	1991-02-05	Hoechst Celanese Corporation	Producing a copolyester from a lower dialkyl ester of terephthalic acid, a glycol and a dicarboxylic acid
US5106944A (en) *	1990-07-03	1992-04-21	Eastman Kodak Company	Process and catalyst-inhibitor systems for preparing poly(1,4-cyclohexenedimethylene terephthalate)
KR100343406B1 (ko)	1997-09-03	2002-07-11	야마모토 카즈모토	폴리에스테르 수지 조성물
US6034202A (en) *	1998-03-06	2000-03-07	Alliedsignal Inc.	Polymerization catalysts for polyesters
US8445555B2 (en)	2006-07-13	2013-05-21	Air Products And Chemicals, Inc.	Stabilized carbanions as trimerization catalysts
WO2016149550A1 (fr)	2015-03-17	2016-09-22	Niagara Bottling, Llc	Polyéthylène téréphtalate renforcé de graphène
CN111253618A (zh)	2015-03-17	2020-06-09	尼亚加拉装瓶有限责任公司	石墨烯增强的聚对苯二甲酸乙二醇酯
MX2018000003A (es)	2015-07-08	2019-01-31	Niagara Bottling Llc	Tereftalato de polietileno reforzado con grafeno.
AU2019267690B2 (en)	2018-05-09	2024-11-14	Niagara Bottling, Llc	Poly (ethylene terephthalate)-graphene nanocomposites from improved dispersion
US11472940B2 (en)	2019-04-01	2022-10-18	Niagara Bottling, Llc	Graphene polyethylene terephthalate composite for improving reheat energy consumption
CN114790282B (zh) *	2021-12-30	2023-03-21	康辉新材料科技有限公司	一种纳米微颗粒原位聚合催化剂的制备方法及其应用
CN116003821B (zh) *	2023-02-23	2024-03-05	西安交通大学	Mof纳米材料及制备方法、负载金属单原子mof纳米材料的制备方法和应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1235867A (fr) *	1958-09-17	1960-07-08	Westinghouse Electric Corp	Résines polyesters
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
US3907754A (en) *	1974-06-19	1975-09-23	Eastman Kodak Co	Process and catalyst-inhibitor system for preparing synthetic linear polyester

1975
- 1975-10-01 CA CA236,847A patent/CA1057734A/fr not_active Expired
- 1975-10-30 IT IT2884675A patent/IT1044090B/it active
- 1975-10-30 JP JP13095175A patent/JPS5168489A/ja active Pending
- 1975-10-30 DE DE19752548630 patent/DE2548630A1/de not_active Withdrawn
- 1975-10-31 FR FR7533316A patent/FR2289524A1/fr active Granted
- 1975-10-31 GB GB4535375A patent/GB1522656A/en not_active Expired

Also Published As

Publication number	Publication date
IT1044090B (it)	1980-03-20
GB1522656A (en)	1978-08-23
FR2289524A1 (fr)	1976-05-28
FR2289524B1 (fr)	1979-06-22
DE2548630A1 (de)	1976-05-06
JPS5168489A (ja)	1976-06-14

Publication	Publication Date	Title
US3962189A (en)	1976-06-08	Process and catalyst-inhibitor systems for preparing synthetic linear polyesters
US4010145A (en)	1977-03-01	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
CA1057734A (fr)	1979-07-03	Procede et systeme catalyseur-inhibiteur pour la preparation de polyesters synthetiques a chaines lineaires
US2720507A (en)	1955-10-11	Organo-metallic tin catalysts for preparation of polyesters
US4501878A (en)	1985-02-26	Process for the preparation of high molecular weight polyesters
US3361846A (en)	1968-01-02	Phenolic phosphate and phosphite esters as stabilizers for saturated polyester resins
US3528946A (en)	1970-09-15	Acetylacetonates as polycondensation catalysts in transesterification method of preparing polyesters
KR101386223B1 (ko)	2014-04-17	폴리에스테르 제조용 촉매 조성물, 및 이를 이용한 폴리에스테르의 제조 방법
US4156072A (en)	1979-05-22	Coordination complexes as polyesterification catalysts
US4104263A (en)	1978-08-01	Process for producing film and fiber-forming polyalkylene terephthalate
WO2002057335A1 (fr)	2002-07-25	Catalyseur de polymerisation de polyester, polyester et procede de fabrication de celui-ci
US3444139A (en)	1969-05-13	Preparation of highly polymeric polyesters in the presence of catalytic titanium compounds containing ester groups
US3321444A (en)	1967-05-23	Process for the manufacture of high molecular weight linear polyesters
US3852247A (en)	1974-12-03	Polymerization catalyst
CA1081675A (fr)	1980-07-15	Procede et systemes catalyseur-inhibiteur pour la preparation de polyesters lineaires synthetiques
US2956985A (en)	1960-10-18	Metal salts of dithiocarbamic acids as catalysts in the production of polyesters
US4067857A (en)	1978-01-10	Polyester catalyst system comprising an antimony-containing polycondensation catalyst and an ethylenically unsaturated compound and process employing same
US3758535A (en)	1973-09-11	Process of reacting a silicon compound with a titanium compound
KR101385721B1 (ko)	2014-04-15	복합 금속 산화물, 및 이를 이용하여 폴리에스테르를 제조하는 방법
KR102718885B1 (ko)	2024-10-16	티타늄계 촉매를 포함하는 필름용 폴리에스테르 수지 조성물 및 그 제조방법
US3654233A (en)	1972-04-04	Process for the manufacture of linear polyesters using metal germanates and metal glycol germanates as the catalyst
US4082724A (en)	1978-04-04	Production of aromatic polyesters of improved color
US2998412A (en)	1961-08-29	Process for manufacture of polyethylene terephthalate with zinc acetateantimony trifluoride catalyst system
US3706711A (en)	1972-12-19	Process for the manufacture of highly polymeric polyesters utilizing samarium compound catalysts