CS201046B2 - Polycondensation catalytic system for polyesters preparing - Google Patents

Polycondensation catalytic system for polyesters preparing Download PDF

Info

Publication number: CS201046B2
Authority: CS; Czechoslovakia
Prior art keywords: group; ethylenically unsaturated; formula; unsaturated compound; catalyst system
Prior art date: 1976-05-21

Application number

CS772600A

Other languages

Czech (cs)

English (en)

Inventor

Ronald L Muntz

Original Assignee

Stauffer Chemical 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.)

1976-05-21

Filing date

1977-04-19

Publication date

1980-10-31

1977-04-19 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1980-10-31 Publication of CS201046B2 publication Critical patent/CS201046B2/cs

Links

238000006068 polycondensation reaction Methods 0.000 title claims abstract description 44
230000003197 catalytic effect Effects 0.000 title claims description 7
229920000728 polyester Polymers 0.000 title claims description 6
239000003054 catalyst Substances 0.000 claims abstract description 52
150000001875 compounds Chemical class 0.000 claims abstract description 49
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
-1 polyol methacrylate Chemical class 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 14
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
150000002431 hydrogen Chemical group 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
FAWGZAFXDJGWBB-UHFFFAOYSA-N antimony(3+) Chemical compound [Sb+3] FAWGZAFXDJGWBB-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
229920005862 polyol Polymers 0.000 claims description 4
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
ZCJLOOJRNPHKAV-ONEGZZNKSA-N (e)-3-(furan-2-yl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CO1 ZCJLOOJRNPHKAV-ONEGZZNKSA-N 0.000 claims description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000000468 ketone group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 3
150000003077 polyols Chemical class 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
150000007942 carboxylates Chemical group 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000003172 aldehyde group Chemical group 0.000 claims 2
125000003368 amide group Chemical group 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 2
125000000879 imine group Chemical group 0.000 claims 2
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 2
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
150000001244 carboxylic acid anhydrides Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
125000005067 haloformyl group Chemical group 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
229910052787 antimony Inorganic materials 0.000 abstract description 20
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract description 18
HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 abstract description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 15
239000007795 chemical reaction product Substances 0.000 description 15
229920000642 polymer Polymers 0.000 description 13
239000002253 acid Substances 0.000 description 12
150000002148 esters Chemical group 0.000 description 9
238000000034 method Methods 0.000 description 9
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 7
KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
YGBFTDQFAKDXBZ-UHFFFAOYSA-N tributyl stiborite Chemical compound [Sb+3].CCCC[O-].CCCC[O-].CCCC[O-] YGBFTDQFAKDXBZ-UHFFFAOYSA-N 0.000 description 5
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical class [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 2
150000001463 antimony compounds Chemical class 0.000 description 2
229910000410 antimony oxide Inorganic materials 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical compound NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 2
229930016911 cinnamic acid Natural products 0.000 description 2
235000013985 cinnamic acid Nutrition 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
239000000835 fiber Substances 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical class [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
239000003039 volatile agent Substances 0.000 description 2
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 1
WBGKAOURNYRYBT-UHFFFAOYSA-N 2-sulfopropanoic acid Chemical compound OC(=O)C(C)S(O)(=O)=O WBGKAOURNYRYBT-UHFFFAOYSA-N 0.000 description 1
LVNFDRRMQPYNBD-UHFFFAOYSA-N 4-ethoxy-2-methylidenebutanoic acid Chemical compound CCOCCC(=C)C(O)=O LVNFDRRMQPYNBD-UHFFFAOYSA-N 0.000 description 1
REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
241000208202 Linaceae Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 1
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YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001462 antimony Chemical class 0.000 description 1
FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
XQRVLQLHRAJWLU-UHFFFAOYSA-K antimony(3+);butanoate Chemical compound [Sb+3].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O XQRVLQLHRAJWLU-UHFFFAOYSA-K 0.000 description 1
JEPVJCOLPSALKN-UHFFFAOYSA-N antimony(3+);ethane-1,2-diolate Chemical compound O1CCO[Sb]2OCCO[Sb]1OCCO2 JEPVJCOLPSALKN-UHFFFAOYSA-N 0.000 description 1
PALVEAZBDSAOLL-UHFFFAOYSA-K antimony(3+);tribenzoate Chemical compound [Sb+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 PALVEAZBDSAOLL-UHFFFAOYSA-K 0.000 description 1
RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical compound Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000001743 benzylic group Chemical group 0.000 description 1
BMYPOELGNTXHPU-UHFFFAOYSA-H bis(4,5-dioxo-1,3,2-dioxastibolan-2-yl) oxalate Chemical compound [Sb+3].[Sb+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O BMYPOELGNTXHPU-UHFFFAOYSA-H 0.000 description 1
YXEDCURRROXRPL-UHFFFAOYSA-K bis[(2-hydroxyacetyl)oxy]stibanyl 2-hydroxyacetate Chemical class [Sb+3].OCC([O-])=O.OCC([O-])=O.OCC([O-])=O YXEDCURRROXRPL-UHFFFAOYSA-K 0.000 description 1
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KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
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238000003776 cleavage reaction Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
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BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
PFJCGWXJUOZSJT-UHFFFAOYSA-N ethyl phenyl sulfate Chemical compound CCOS(=O)(=O)OC1=CC=CC=C1 PFJCGWXJUOZSJT-UHFFFAOYSA-N 0.000 description 1
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BQIGMBPWIKZNQY-UHFFFAOYSA-N n-aminothiohydroxylamine Chemical compound NNS BQIGMBPWIKZNQY-UHFFFAOYSA-N 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
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ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
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239000001384 succinic acid Substances 0.000 description 1
YPMOSINXXHVZIL-UHFFFAOYSA-N sulfanylideneantimony Chemical compound [Sb]=S YPMOSINXXHVZIL-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
229940093635 tributyl phosphate Drugs 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
GUXFCNIUPCZBHE-UHFFFAOYSA-N trimethyl stiborate Chemical compound CO[Sb](=O)(OC)OC GUXFCNIUPCZBHE-UHFFFAOYSA-N 0.000 description 1
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
BIDDLDNGQCUOJQ-SDNWHVSQSA-N α-phenylcinnamic acid Chemical compound C=1C=CC=CC=1/C(C(=O)O)=C\C1=CC=CC=C1 BIDDLDNGQCUOJQ-SDNWHVSQSA-N 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
- C08G63/87—Non-metals or inter-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
- C08G63/86—Germanium, antimony, or compounds thereof
- C08G63/866—Antimony 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)

CS772600A 1976-05-21 1977-04-19 Polycondensation catalytic system for polyesters preparing CS201046B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/688,796 US4067857A (en)	1976-05-21	1976-05-21	Polyester catalyst system comprising an antimony-containing polycondensation catalyst and an ethylenically unsaturated compound and process employing same

Publications (1)

Publication Number	Publication Date
CS201046B2 true CS201046B2 (en)	1980-10-31

Family

ID=24765812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS772600A CS201046B2 (en)	1976-05-21	1977-04-19	Polycondensation catalytic system for polyesters preparing

Country Status (12)

Country	Link
US (1)	US4067857A (nl)
JP (1)	JPS52142690A (nl)
BE (1)	BE854838A (nl)
BR (1)	BR7702729A (nl)
CA (1)	CA1094536A (nl)
CS (1)	CS201046B2 (nl)
DD (1)	DD130255A5 (nl)
DE (1)	DE2716558A1 (nl)
FR (1)	FR2352014A1 (nl)
GB (1)	GB1540213A (nl)
IE (1)	IE44800B1 (nl)
NL (1)	NL7705452A (nl)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4187257A (en) *	1978-04-18	1980-02-05	The Dow Chemical Company	Radiation curable vinyl ester resin
ATE293652T1 (de) *	1999-12-10	2005-05-15	Equipolymers Gmbh	Katalysatorsysteme für polykondensationsreaktionen
ATE344817T1 (de)	2002-05-09	2006-11-15	Equipolymers Gmbh	Katalysatorsystem für polykondensationsreaktionen
US20050010017A1 (en) *	2003-07-11	2005-01-13	Blakely Dale Milton	Addition of UV inhibitors to pet process for maximum yield
US20050277716A1 (en) *	2004-05-27	2005-12-15	Pearson Jason C	Furyl-2-methylidene UV absorbers and compositions incorporating the UV absorbers
US20050267283A1 (en) *	2004-05-27	2005-12-01	Weaver Max A	Process for adding nitrogen containing methine light absorbers to poly(ethylene terephthalate)
US20050277759A1 (en) *	2004-05-27	2005-12-15	Pearson Jason C	Process for adding furyl-2-methylidene UV light absorbers to poly(ethylene terephthalate)
US7541407B2 (en) *	2004-05-27	2009-06-02	Eastman Chemical Company	Process for adding methine UV light absorbers to PET prepared by direct esterification

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3484410A (en) *	1966-11-23	1969-12-16	Allied Chem	Process for preparing polyesters with antimony catalysts
US3687860A (en) *	1969-11-06	1972-08-29	Okura Industrial Co Ltd	Polymerizable mixtures comprising a halogenated bivalent metal salt of an acrylate- or methacrylate-phthalate ester of an alkylene glycol

1976
- 1976-05-21 US US05/688,796 patent/US4067857A/en not_active Expired - Lifetime
1977
- 1977-03-28 IE IE641/77A patent/IE44800B1/en unknown
- 1977-03-30 CA CA275,164A patent/CA1094536A/en not_active Expired
- 1977-04-05 GB GB14310/77A patent/GB1540213A/en not_active Expired
- 1977-04-14 DE DE19772716558 patent/DE2716558A1/de not_active Withdrawn
- 1977-04-19 CS CS772600A patent/CS201046B2/cs unknown
- 1977-04-19 FR FR7711679A patent/FR2352014A1/fr active Granted
- 1977-04-21 JP JP4632177A patent/JPS52142690A/ja active Pending
- 1977-04-28 BR BR7702729A patent/BR7702729A/pt unknown
- 1977-05-09 DD DD7700198829A patent/DD130255A5/xx unknown
- 1977-05-17 NL NL7705452A patent/NL7705452A/nl not_active Application Discontinuation
- 1977-05-20 BE BE2055922A patent/BE854838A/nl unknown

Also Published As

Publication number	Publication date
US4067857A (en)	1978-01-10
CA1094536A (en)	1981-01-27
DD130255A5 (de)	1978-03-15
BR7702729A (pt)	1978-03-21
DE2716558A1 (de)	1977-12-01
FR2352014A1 (fr)	1977-12-16
JPS52142690A (en)	1977-11-28
FR2352014B1 (nl)	1981-02-27
IE44800B1 (en)	1982-04-07
IE44800L (en)	1977-11-21
NL7705452A (nl)	1977-11-23
BE854838A (nl)	1977-11-21
GB1540213A (en)	1979-02-07

Publication	Publication Date	Title
RU2181307C2 (ru)	2002-04-20	Катализаторы этерификации
US3907754A (en)	1975-09-23	Process and catalyst-inhibitor system for preparing synthetic linear polyester
BE1008343A3 (nl)	1996-04-02	Bidentaat fosfineligand
CS201046B2 (en)	1980-10-31	Polycondensation catalytic system for polyesters preparing
US2820023A (en)	1958-01-14	Ester interchange reaction using a lanthanum catalyst
JP2002512267A (ja)	2002-04-23	チタン化合物とアミンと燐化合物を含んで成る触媒組成物、それの製造および使用
CZ20014470A3 (cs)	2002-05-15	Způsob přípravy bisfenolalkoxylátů
US4087408A (en)	1978-05-02	Bromine and phosphorus containing polyester
EP0160427B1 (en)	1988-07-06	Alcoholysis of esters and metal alcoholates used in this process
RU2048465C1 (ru)	1995-11-20	Способ получения сложных органических эфиров или амидов
CZ157896A3 (en)	1996-12-11	Highly active catalytic system for poly/ethyleneterephthalate/ synthesis
US3538045A (en)	1970-11-03	Thermal stabilization of polyesters
US4142904A (en)	1979-03-06	Flame retardant polycarboxy alkyl and aryl phosphonates
US2652416A (en)	1953-09-15	Reaction of lactones with trialkyl phosphite
US3533994A (en)	1970-10-13	Stabilized polyesters
CA1047523A (en)	1979-01-30	Processes for preparing phenolic diesters
US4234496A (en)	1980-11-18	Complex organo-metallic compounds of boron or phosphorus
US3053809A (en)	1962-09-11	Phosphine-metal compound catalyst
US3305608A (en)	1967-02-21	Phenolic phosphites
JPH0565339A (ja)	1993-03-19	難燃性ポリエステルの製法
JPH04364196A (ja)	1992-12-16	ホスフィン酸誘導体からなる反応性難燃剤およびこの誘導体の製法
EP0244916A1 (en)	1987-11-11	Method of making organic solvent soluble zinc alkoxy alkoxides
KR800000447B1 (ko)	1980-05-29	폴리에스테르 제조용 촉매조성물
US20070179045A1 (en)	2007-08-02	Mixed catalytic composition
US3962378A (en)	1976-06-08	Preparation of phosphorus-organic esters