CA2666585A1 - Polyester compositions - Google Patents
Polyester compositions Download PDFInfo
- Publication number
- CA2666585A1 CA2666585A1 CA002666585A CA2666585A CA2666585A1 CA 2666585 A1 CA2666585 A1 CA 2666585A1 CA 002666585 A CA002666585 A CA 002666585A CA 2666585 A CA2666585 A CA 2666585A CA 2666585 A1 CA2666585 A1 CA 2666585A1
- Authority
- CA
- Canada
- Prior art keywords
- mole
- polyester
- ppm
- tetramethyl
- atoms
- 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.)
- Abandoned
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 654
- 239000000203 mixture Substances 0.000 title claims abstract description 262
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 1305
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical group CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 claims abstract description 328
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 152
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 106
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 93
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims abstract description 91
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 87
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 48
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims abstract description 44
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- -1 phosphorus compound Chemical class 0.000 claims description 307
- 238000000034 method Methods 0.000 claims description 215
- 230000008569 process Effects 0.000 claims description 187
- 229910052698 phosphorus Inorganic materials 0.000 claims description 114
- 239000011574 phosphorus Substances 0.000 claims description 114
- 239000003054 catalyst Substances 0.000 claims description 79
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 72
- 229910019142 PO4 Inorganic materials 0.000 claims description 55
- 235000021317 phosphate Nutrition 0.000 claims description 55
- 150000003609 titanium compounds Chemical class 0.000 claims description 41
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- 238000010438 heat treatment Methods 0.000 claims description 33
- 239000003017 thermal stabilizer Substances 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 27
- 229910052718 tin Inorganic materials 0.000 claims description 25
- 150000003606 tin compounds Chemical class 0.000 claims description 24
- 239000007795 chemical reaction product Substances 0.000 claims description 20
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 19
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 18
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 16
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 14
- 229910052749 magnesium Inorganic materials 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 14
- 229920000515 polycarbonate Polymers 0.000 claims description 14
- 239000004417 polycarbonate Substances 0.000 claims description 14
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 13
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 13
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052782 aluminium Inorganic materials 0.000 claims description 13
- 229910052787 antimony Inorganic materials 0.000 claims description 13
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 13
- 239000006085 branching agent Substances 0.000 claims description 13
- 229910017052 cobalt Inorganic materials 0.000 claims description 13
- 239000010941 cobalt Substances 0.000 claims description 13
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 13
- 229910052733 gallium Inorganic materials 0.000 claims description 13
- 229910052732 germanium Inorganic materials 0.000 claims description 13
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 13
- 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 claims description 13
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- 239000011701 zinc Substances 0.000 claims description 13
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 239000004609 Impact Modifier Substances 0.000 claims description 5
- 229920002959 polymer blend Polymers 0.000 claims description 5
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 4
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 4
- 229920002492 poly(sulfone) Polymers 0.000 claims description 4
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 4
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- YICSVBJRVMLQNS-UHFFFAOYSA-N dibutyl phenyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OC1=CC=CC=C1 YICSVBJRVMLQNS-UHFFFAOYSA-N 0.000 claims description 3
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 239000012963 UV stabilizer Substances 0.000 claims description 2
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000003365 glass fiber Substances 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 239000006082 mold release agent Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 2
- 229920012287 polyphenylene sulfone Polymers 0.000 claims description 2
- 229920005990 polystyrene resin Polymers 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 229940043375 1,5-pentanediol Drugs 0.000 claims 1
- FQXGHZNSUOHCLO-IZLXSQMJSA-N CC1(C)[C@H](O)C(C)(C)[C@H]1O Chemical group CC1(C)[C@H](O)C(C)(C)[C@H]1O FQXGHZNSUOHCLO-IZLXSQMJSA-N 0.000 claims 1
- 229920000049 Carbon (fiber) Polymers 0.000 claims 1
- 239000004917 carbon fiber Substances 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 45
- 239000010452 phosphate Substances 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 25
- 229920001634 Copolyester Polymers 0.000 description 24
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 23
- 239000010936 titanium Substances 0.000 description 23
- 229910052719 titanium Inorganic materials 0.000 description 22
- 239000002253 acid Substances 0.000 description 21
- 150000002009 diols Chemical class 0.000 description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 20
- 239000011521 glass Substances 0.000 description 20
- 230000009477 glass transition Effects 0.000 description 20
- 239000000178 monomer Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 18
- 230000004888 barrier function Effects 0.000 description 15
- 238000005886 esterification reaction Methods 0.000 description 15
- 150000002334 glycols Chemical class 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 239000000976 ink Substances 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 12
- 238000006068 polycondensation reaction Methods 0.000 description 12
- 150000003014 phosphoric acid esters Chemical class 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 10
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 10
- 238000001125 extrusion Methods 0.000 description 10
- 239000005340 laminated glass Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000010924 continuous production Methods 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 239000012974 tin catalyst Substances 0.000 description 6
- 239000004408 titanium dioxide Substances 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 239000004970 Chain extender Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000003490 calendering Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- WNVQCJNZEDLILP-UHFFFAOYSA-N dimethyl(oxo)tin Chemical compound C[Sn](C)=O WNVQCJNZEDLILP-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- 229910000634 wood's metal Inorganic materials 0.000 description 5
- WBWXVCMXGYSMQA-UHFFFAOYSA-N 3,9-bis[2,4-bis(2-phenylpropan-2-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C=1C=C(OP2OCC3(CO2)COP(OC=2C(=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C(C)(C)C=2C=CC=CC=2)OC3)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 WBWXVCMXGYSMQA-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000000020 Nitrocellulose Substances 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 4
- 238000013480 data collection Methods 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920001220 nitrocellulos Polymers 0.000 description 4
- 238000004886 process control Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000003856 thermoforming Methods 0.000 description 4
- 229910001887 tin oxide Inorganic materials 0.000 description 4
- WIGMBAFWGLANJY-UHFFFAOYSA-N 2,3-dihydroindene-1,1-dicarboxylic acid Chemical class C1=CC=C2C(C(=O)O)(C(O)=O)CCC2=C1 WIGMBAFWGLANJY-UHFFFAOYSA-N 0.000 description 3
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000010943 off-gassing Methods 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 3
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- 229910052708 sodium Inorganic materials 0.000 description 1
- VVNRQZDDMYBBJY-UHFFFAOYSA-M sodium 1-[(1-sulfonaphthalen-2-yl)diazenyl]naphthalen-2-olate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 VVNRQZDDMYBBJY-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 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 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- WBVCLUDHJDTUAU-UHFFFAOYSA-N tetrabenzylstannane Chemical compound C=1C=CC=CC=1C[Sn](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 WBVCLUDHJDTUAU-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 description 1
- KCSOHLKZTZMKQA-UHFFFAOYSA-M tetraheptylazanium;iodide Chemical compound [I-].CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC KCSOHLKZTZMKQA-UHFFFAOYSA-M 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- OACSUWPJZKGHHK-UHFFFAOYSA-N tribenzyl phosphate Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)(=O)OCC1=CC=CC=C1 OACSUWPJZKGHHK-UHFFFAOYSA-N 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- OHRVKCZTBPSUIK-UHFFFAOYSA-N tridodecyl phosphate Chemical compound CCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCC)OCCCCCCCCCCCC OHRVKCZTBPSUIK-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- HNJXPTMEWIVQQM-UHFFFAOYSA-M triethyl(hexadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](CC)(CC)CC HNJXPTMEWIVQQM-UHFFFAOYSA-M 0.000 description 1
- XWSLYQXUTWUIKM-UHFFFAOYSA-N trimethoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC XWSLYQXUTWUIKM-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
-
- 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
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- 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)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (47)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| USPCT/US06/42069 | 2006-10-27 | ||
| PCT/US2006/042069 WO2007053460A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions which comprise cyclobutanediol and at least one phosphorus compound |
| PCT/US2006/041917 WO2007053434A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof |
| US11/588,883 US20070105993A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions which comprise cyclobutanediol and at least one phosphorus compound |
| USPCT/US06/42293 | 2006-10-27 | ||
| US11/588,458 US20070100122A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions containing cyclobutanediol and articles made therefrom |
| USPCT/US06/42292 | 2006-10-27 | ||
| US11/588,883 | 2006-10-27 | ||
| US11/588,554 | 2006-10-27 | ||
| PCT/US2006/042293 WO2007053550A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions containing cyclobutanediol having high glass transition temperature and articles made therefrom |
| US11/588,527 | 2006-10-27 | ||
| USPCT/US06/42291 | 2006-10-27 | ||
| US11/588,906 US8193302B2 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions which comprise cyclobutanediol and certain phosphate thermal stabilizers, and/or reaction products thereof |
| US11/588,906 | 2006-10-27 | ||
| PCT/US2006/042291 WO2007053548A2 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions comprising minimal amounts of cyclobutanediol |
| US11/588,524 US20100096589A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions containing low amounts of cyclobutanediol and articles made therefrom |
| US11/588,458 | 2006-10-27 | ||
| US11/588,554 US20070100125A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions comprising minimal amounts of cyclobutanediol |
| US11/588,907 | 2006-10-27 | ||
| US11/588,524 | 2006-10-27 | ||
| US11/588,907 US20070106054A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and high glass transition temperature and articles made therefrom |
| PCT/US2006/042292 WO2007053549A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom |
| US11/588,527 US20100087574A1 (en) | 2005-10-28 | 2006-10-27 | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom |
| USPCT/US06/41917 | 2006-10-27 | ||
| US11/635,434 | 2006-12-07 | ||
| US11/635,433 US20070142511A1 (en) | 2005-12-15 | 2006-12-07 | Polyester compositions which comprise cyclobutanediol ethylene glycol, titanium, and phosphorus with improved color and manufacturing processes therefor |
| US11/635,433 | 2006-12-07 | ||
| US11/635,434 US7737246B2 (en) | 2005-12-15 | 2006-12-07 | Polyester compositions which comprise cyclobutanediol, cyclohexanedimethanol, and ethylene glycol and manufacturing processes therefor |
| US11/706,476 | 2007-02-14 | ||
| US11/706,476 US20070232778A1 (en) | 2006-03-28 | 2007-02-14 | Certain polyester compositions which comprise cyclobutanediol, cyclohexanedimethanol, and high trans-cyclohexanedicarboxylic acid |
| US11/706,791 US20070232779A1 (en) | 2006-03-28 | 2007-02-14 | Certain polyester compositions which comprise cyclohexanedimethanol, moderate cyclobutanediol, cyclohexanedimethanol, and high trans cyclohexanedicarboxylic acid |
| US11/706,791 | 2007-02-14 | ||
| PCT/US2007/007532 WO2007123631A1 (en) | 2006-03-28 | 2007-03-27 | Polyester compositions which comprise cyclobutanediol and at least one phosphorus compound |
| USPCT/US07/07632 | 2007-03-27 | ||
| PCT/US2007/007632 WO2007126855A1 (en) | 2006-03-28 | 2007-03-27 | Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof |
| USPCT/US07/07532 | 2007-03-27 | ||
| PCT/US2007/010590 WO2007139655A1 (en) | 2006-05-23 | 2007-05-02 | Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof |
| PCT/US2007/010551 WO2007139653A1 (en) | 2006-05-23 | 2007-05-02 | Lcd films or sheets comprising films comprising polyester compositions formed from 2,2,4,4,-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
| USPCT/US07/10551 | 2007-05-02 | ||
| USPCT/US07/10590 | 2007-05-02 | ||
| PCT/US2007/011150 WO2007139663A1 (en) | 2006-05-23 | 2007-05-09 | Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof |
| USPCT/US07/11150 | 2007-05-09 | ||
| US91731607P | 2007-05-10 | 2007-05-10 | |
| US60/917,316 | 2007-05-10 | ||
| US11/773,275 | 2007-07-03 | ||
| US11/773,275 US8586701B2 (en) | 2005-10-28 | 2007-07-03 | Process for the preparation of copolyesters based on 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
| PCT/US2007/015704 WO2008051321A1 (en) | 2006-10-27 | 2007-07-10 | Polyester compositions which comprise cyclobutanediol, ethylene glycol, titanium, and phosphorus with improved color and manufacturing processes therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2666585A1 true CA2666585A1 (en) | 2008-05-02 |
Family
ID=47831243
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002666585A Abandoned CA2666585A1 (en) | 2006-10-27 | 2007-07-10 | Polyester compositions |
| CA002666571A Abandoned CA2666571A1 (en) | 2006-10-27 | 2007-07-10 | Polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and ethylene glycol, and manufacturing processes therefor |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002666571A Abandoned CA2666571A1 (en) | 2006-10-27 | 2007-07-10 | Polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and ethylene glycol, and manufacturing processes therefor |
Country Status (8)
| Country | Link |
|---|---|
| EP (2) | EP2074174A1 (pt) |
| JP (2) | JP2010507716A (pt) |
| KR (2) | KR20090079211A (pt) |
| BR (2) | BRPI0717761A2 (pt) |
| CA (2) | CA2666585A1 (pt) |
| MX (2) | MX2009003375A (pt) |
| TW (2) | TW200819497A (pt) |
| WO (4) | WO2008054559A1 (pt) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8163850B2 (en) * | 2009-02-06 | 2012-04-24 | Eastman Chemical Company | Thermosetting polyester coating compositions containing tetramethyl cyclobutanediol |
| US8168721B2 (en) * | 2009-02-06 | 2012-05-01 | Eastman Chemical Company | Coating compositions containing tetramethyl cyclobutanediol |
| US9029460B2 (en) * | 2009-02-06 | 2015-05-12 | Stacey James Marsh | Coating compositions containing acrylic and aliphatic polyester blends |
| US7915374B2 (en) * | 2009-04-27 | 2011-03-29 | Eastman Chemical Company | Copolyesters having improved thermal stability and methods for making them |
| US9156941B2 (en) * | 2010-12-20 | 2015-10-13 | Eastman Chemical Company | Color in titanium catalyzed polyesters |
| US8309624B2 (en) * | 2011-01-17 | 2012-11-13 | Eastman Chemical Company | Haze reduction for blends of aromatic-aliphatic polyesters and antimicrobial additives |
| US8580872B2 (en) * | 2011-07-21 | 2013-11-12 | Eastman Chemical Company | Sulfopolyester polymer compositions with improved water dispersibility |
| EP2774950B1 (en) * | 2011-11-01 | 2019-03-27 | Midori Anzen Co., Ltd. | Resin composition and molded body |
| US8623483B1 (en) * | 2012-10-23 | 2014-01-07 | Eastman Chemical Company | Copolyesters containing neopentyl glycol and 2,2,4,4-tetraalkyl 1,3-cyclobutanediol |
| WO2015125644A1 (ja) * | 2014-02-24 | 2015-08-27 | 東レ株式会社 | ポリエステルフィルム |
| WO2015129500A1 (ja) * | 2014-02-27 | 2015-09-03 | 東レ株式会社 | 積層フィルム |
| JP6323871B2 (ja) * | 2014-07-31 | 2018-05-16 | 花王株式会社 | 電子写真用トナー |
| JP6323872B2 (ja) * | 2014-07-31 | 2018-05-16 | 花王株式会社 | 電子写真用トナー |
| JP2015028177A (ja) * | 2014-09-22 | 2015-02-12 | イーストマン ケミカル カンパニー | ポリエステルを製造するための改善された方法 |
| JP7130621B2 (ja) * | 2016-08-18 | 2022-09-05 | イーストマン ケミカル カンパニー | 改良された触媒系による、テトラメチルシクロブタンジオール及びエチレングリコールを含むポリエステル組成物 |
| WO2018035341A1 (en) * | 2016-08-18 | 2018-02-22 | Eastman Chemical Company | Polyester compositions which comprise tetramethylcyclobutanediol and ethylene glycol for calendering |
| EP3500616B1 (en) * | 2016-08-18 | 2021-03-24 | Eastman Chemical Company | Polyester compositions which comprise tetramethylcyclobutandiol and ethylene glycol, with improved catalyst system |
| KR102589382B1 (ko) * | 2018-08-08 | 2023-10-12 | 에스케이케미칼 주식회사 | 폴리에스테르 수지 및 이의 제조방법 |
| JP7565337B2 (ja) * | 2019-08-02 | 2024-10-10 | イーストマン ケミカル カンパニー | 多層シート |
| JP2022552206A (ja) * | 2019-10-08 | 2022-12-15 | イーストマン ケミカル カンパニー | 結晶化可能な反応器級樹脂のための触媒システム |
| US11788317B2 (en) * | 2020-09-28 | 2023-10-17 | Kathryn Corcoran | Cell phone canopy |
| WO2024164223A1 (en) * | 2023-02-09 | 2024-08-15 | Eastman Chemical (China) Co., Ltd. | Molded polyester articles with improved aesthetic chemical resistance |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4525504A (en) * | 1983-10-24 | 1985-06-25 | Eastman Kodak Company | Stabilized polyester compositions suitable for outdoor applications |
| US6495656B1 (en) * | 1990-11-30 | 2002-12-17 | Eastman Chemical Company | Copolyesters and fibrous materials formed therefrom |
| US5498668A (en) * | 1994-10-31 | 1996-03-12 | Eastman Chemical Company | Blends of certain polyesters with acrylics |
| US6043322A (en) * | 1996-12-28 | 2000-03-28 | Eastman Chemical Company | Clear polycarbonate and polyester blends |
| US6037424A (en) * | 1996-12-28 | 2000-03-14 | Eastman Chemical Company | Clear blends of polycarbonates and polyesters |
| US5989663A (en) * | 1996-12-30 | 1999-11-23 | Eastman Chemical Company | Blow-molding polyesters from terephthalic acid, 2, 2, 4, 4-tetramethyl-1,3-cyclobutanediol, and ethylene glycol |
| US6120889A (en) * | 1999-06-03 | 2000-09-19 | Eastman Chemical Company | Low melt viscosity amorphous copolyesters with enhanced glass transition temperatures |
| US20050010017A1 (en) * | 2003-07-11 | 2005-01-13 | Blakely Dale Milton | Addition of UV inhibitors to pet process for maximum yield |
| BRPI0412403A (pt) * | 2003-07-11 | 2006-09-05 | Eastman Chem Co | método para incorporar um absorvedor de uv em uma resina de poliéster, composição de poliéster, e, artigo termoplástico |
| US20060094858A1 (en) * | 2004-10-28 | 2006-05-04 | Turner Sam R | Novel copolyester compositions with improved impact strength at low temperatures |
| WO2007053549A1 (en) * | 2005-10-28 | 2007-05-10 | Eastman Chemical Company | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom |
| JP2009513799A (ja) * | 2005-10-28 | 2009-04-02 | イーストマン ケミカル カンパニー | 最小量のシクロブタンジオールを含むポリエステル組成物 |
-
2007
- 2007-07-10 KR KR1020097008483A patent/KR20090079211A/ko not_active Application Discontinuation
- 2007-07-10 EP EP07836026A patent/EP2074174A1/en not_active Withdrawn
- 2007-07-10 EP EP07836029A patent/EP2074158A1/en not_active Withdrawn
- 2007-07-10 KR KR1020097008484A patent/KR20090079212A/ko not_active Application Discontinuation
- 2007-07-10 WO PCT/US2007/015702 patent/WO2008054559A1/en active Application Filing
- 2007-07-10 CA CA002666585A patent/CA2666585A1/en not_active Abandoned
- 2007-07-10 TW TW096125125A patent/TW200819497A/zh unknown
- 2007-07-10 WO PCT/US2007/015713 patent/WO2008054560A2/en active Application Filing
- 2007-07-10 JP JP2009534565A patent/JP2010507716A/ja not_active Withdrawn
- 2007-07-10 WO PCT/US2007/015701 patent/WO2008051320A1/en active Application Filing
- 2007-07-10 MX MX2009003375A patent/MX2009003375A/es unknown
- 2007-07-10 JP JP2009534566A patent/JP2010507717A/ja not_active Withdrawn
- 2007-07-10 TW TW096125089A patent/TW200819496A/zh unknown
- 2007-07-10 WO PCT/US2007/015704 patent/WO2008051321A1/en active Application Filing
- 2007-07-10 BR BRPI0717761-5A patent/BRPI0717761A2/pt not_active Application Discontinuation
- 2007-07-10 MX MX2009003369A patent/MX2009003369A/es unknown
- 2007-07-10 CA CA002666571A patent/CA2666571A1/en not_active Abandoned
- 2007-07-10 BR BRPI0717755-0A patent/BRPI0717755A2/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010507717A (ja) | 2010-03-11 |
| BRPI0717761A2 (pt) | 2013-03-12 |
| MX2009003369A (es) | 2009-04-14 |
| EP2074174A1 (en) | 2009-07-01 |
| JP2010507716A (ja) | 2010-03-11 |
| TW200819497A (en) | 2008-05-01 |
| CA2666571A1 (en) | 2008-05-02 |
| BRPI0717755A2 (pt) | 2013-03-12 |
| WO2008054559A1 (en) | 2008-05-08 |
| KR20090079211A (ko) | 2009-07-21 |
| WO2008054560A2 (en) | 2008-05-08 |
| TW200819496A (en) | 2008-05-01 |
| EP2074158A1 (en) | 2009-07-01 |
| WO2008054560A3 (en) | 2008-07-24 |
| WO2008051321A8 (en) | 2008-07-10 |
| MX2009003375A (es) | 2009-04-14 |
| WO2008051321A1 (en) | 2008-05-02 |
| WO2008051320A1 (en) | 2008-05-02 |
| KR20090079212A (ko) | 2009-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |