DE2261503C3 - Verfahren zur Herstellung eines zweiten Polyesters aus einem ersten Polyester - Google Patents
Verfahren zur Herstellung eines zweiten Polyesters aus einem ersten PolyesterInfo
- Publication number
- DE2261503C3 DE2261503C3 DE2261503A DE2261503A DE2261503C3 DE 2261503 C3 DE2261503 C3 DE 2261503C3 DE 2261503 A DE2261503 A DE 2261503A DE 2261503 A DE2261503 A DE 2261503A DE 2261503 C3 DE2261503 C3 DE 2261503C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- polymer
- mol
- poly
- polyester
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 59
- 229920000728 polyester Polymers 0.000 title claims description 38
- -1 alkylene radical Chemical class 0.000 description 69
- 229920000642 polymer Polymers 0.000 description 50
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- 238000004519 manufacturing process Methods 0.000 description 25
- 239000000463 material Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 18
- AREMQPPGVQNRIE-UHFFFAOYSA-N acetic acid;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CC(O)=O.CC(O)=O.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 AREMQPPGVQNRIE-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000005977 Ethylene Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000000155 melt Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000010309 melting process Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- AKOGNYJNGMLDOA-UHFFFAOYSA-N (4-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=C(OC(C)=O)C=C1 AKOGNYJNGMLDOA-UHFFFAOYSA-N 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-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
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- STOUHHBZBQBYHH-UHFFFAOYSA-N (3-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(OC(C)=O)=C1 STOUHHBZBQBYHH-UHFFFAOYSA-N 0.000 description 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- XFQHIELVPOKJIM-UHFFFAOYSA-N 1,4-dioxacyclotetradecane-5,14-dione Chemical compound O=C1CCCCCCCCC(=O)OCCO1 XFQHIELVPOKJIM-UHFFFAOYSA-N 0.000 description 1
- QABJRPWOBYCMBO-UHFFFAOYSA-N 1,4-dioxacyclotridecane-5,13-dione Chemical compound O=C1CCCCCCCC(=O)OCCO1 QABJRPWOBYCMBO-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- PNKBWDYDQQBDSN-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=C(C=3C(O)=O)C(=O)O)=CC=CC2=C1 PNKBWDYDQQBDSN-UHFFFAOYSA-N 0.000 description 1
- PQHRHABVSWOYPG-UHFFFAOYSA-N 2,9-dioxatricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaene-3,8-dione Chemical compound O1C(=O)C(C=C2)=CC=C2C(=O)OC2=CC=C1C=C2 PQHRHABVSWOYPG-UHFFFAOYSA-N 0.000 description 1
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- QPGBFKDHRXJSIK-UHFFFAOYSA-N 2-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=C(C(O)=O)C=CC=C1C(O)=O QPGBFKDHRXJSIK-UHFFFAOYSA-N 0.000 description 1
- CSSJQJWTYJODDJ-UHFFFAOYSA-N 3,10-dioxatricyclo[10.2.2.04,9]hexadeca-1(15),4,6,8,12(16),13-hexaene-2,11-dione Chemical compound O1C(=O)C(C=C2)=CC=C2C(=O)OC2=C1C=CC=C2 CSSJQJWTYJODDJ-UHFFFAOYSA-N 0.000 description 1
- MMINFSMURORWKH-UHFFFAOYSA-N 3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical compound O=C1OCCOC(=O)C2=CC=C1C=C2 MMINFSMURORWKH-UHFFFAOYSA-N 0.000 description 1
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 1
- VTXUGHWRBWRSDI-UHFFFAOYSA-N 3,9-dioxatricyclo[9.2.2.14,8]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-2,10-dione Chemical compound O1C(=O)C(C=C2)=CC=C2C(=O)OC2=CC1=CC=C2 VTXUGHWRBWRSDI-UHFFFAOYSA-N 0.000 description 1
- BCERVBGVOSICNO-UHFFFAOYSA-N 3-[2-(2-carboxyethyl)phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1CCC(O)=O BCERVBGVOSICNO-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- RHKYINYUOWWCHP-UHFFFAOYSA-N 4-[(2,4-dichlorophenyl)-(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C(=CC(Cl)=CC=1)Cl)C1=CC=C(O)C=C1 RHKYINYUOWWCHP-UHFFFAOYSA-N 0.000 description 1
- SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RYCIIXKBLGUHMY-UHFFFAOYSA-N 9,9-dimethylxanthene-3,6-diol Chemical compound OC1=CC=C2C(C)(C)C3=CC=C(O)C=C3OC2=C1 RYCIIXKBLGUHMY-UHFFFAOYSA-N 0.000 description 1
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 1
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- XSRZEDGZPKVDHC-UHFFFAOYSA-N C1(C2=CC=C(C(=O)OC3=CC=C(C=C3)C(C)(C)C3=CC=C(C=C3)O1)C=C2)=O Chemical compound C1(C2=CC=C(C(=O)OC3=CC=C(C=C3)C(C)(C)C3=CC=C(C=C3)O1)C=C2)=O XSRZEDGZPKVDHC-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920000562 Poly(ethylene adipate) Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- NSNHONPMCQYMNT-UHFFFAOYSA-N [4-[2-(4-acetyloxyphenyl)propan-2-yl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C(C)(C)C1=CC=C(OC(C)=O)C=C1 NSNHONPMCQYMNT-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 229920006127 amorphous resin Polymers 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004976 cyclobutylene group Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- HPGJOUYGWKFYQW-UHFFFAOYSA-N diphenyl benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OC=2C=CC=CC=2)C=CC=1C(=O)OC1=CC=CC=C1 HPGJOUYGWKFYQW-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical class 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011089 mechanical engineering Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- JSKSILUXAHIKNP-UHFFFAOYSA-N naphthalene-1,7-dicarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=CC(C(=O)O)=CC=C21 JSKSILUXAHIKNP-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/795—Photosensitive materials characterised by the base or auxiliary layers the base being of macromolecular substances
- G03C1/7954—Polyesters
-
- 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
- C08G63/19—Hydroxy compounds containing aromatic 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
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
- C08G63/80—Solid-state polycondensation
-
- 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
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
- G03C1/498—Photothermographic systems, e.g. dry silver
- G03C1/49836—Additives
- G03C1/49863—Inert additives, e.g. surfactants, binders
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US22297772A | 1972-02-02 | 1972-02-02 |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2261503A1 DE2261503A1 (de) | 1973-08-09 |
DE2261503B2 DE2261503B2 (de) | 1978-02-09 |
DE2261503C3 true DE2261503C3 (de) | 1978-09-28 |
Family
ID=22834486
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2261503A Expired DE2261503C3 (de) | 1972-02-02 | 1972-12-15 | Verfahren zur Herstellung eines zweiten Polyesters aus einem ersten Polyester |
Country Status (7)
Country | Link |
---|---|
US (1) | US3772405A ( ) |
JP (1) | JPS4888193A ( ) |
BE (1) | BE794938A ( ) |
CA (1) | CA1008588A ( ) |
DE (1) | DE2261503C3 ( ) |
FR (1) | FR2170166B1 ( ) |
GB (1) | GB1402973A ( ) |
Families Citing this family (129)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3856526A (en) * | 1973-08-06 | 1974-12-24 | Eastman Kodak Co | Protective layer for photothermographic elements |
US3856527A (en) * | 1973-08-06 | 1974-12-24 | Eastman Kodak Co | Protective layer for photothermographic elements |
US3890256A (en) * | 1974-06-07 | 1975-06-17 | Eastman Kodak Co | Copolyester prepared by contacting acyloxy benzoic acid with a polyester of ethylene glycol and dicarboxylic acid |
JPS5921888B2 (ja) * | 1974-11-07 | 1984-05-23 | 帝人株式会社 | ポリエステルの製造法 |
US4115362A (en) * | 1975-10-03 | 1978-09-19 | Teijin Limited | Process for preparing polyesters |
US4124566A (en) * | 1976-06-16 | 1978-11-07 | Teijin Limited | Process for preparing polyesters |
US4128526A (en) * | 1976-12-23 | 1978-12-05 | General Electric Company | Copolyesters of poly(alkylene glycol aromatic acid esters) and diesters comprising aromatic diols |
US4250281A (en) * | 1979-03-21 | 1981-02-10 | Eastman Kodak Company | Melt process for preparing copolyesters using triarylphosphine catalysts |
JPS5887125A (ja) * | 1981-11-18 | 1983-05-24 | Asahi Chem Ind Co Ltd | 液晶性ポリエステルの重合法 |
US4474918A (en) * | 1983-05-31 | 1984-10-02 | Eastman Kodak Company | Thermoplastic polyester compositions having improved barrier properties |
JPS60161425A (ja) * | 1984-01-31 | 1985-08-23 | Kishimoto Akira | プラスチツク容器 |
US4612362A (en) * | 1985-03-27 | 1986-09-16 | Allied Corporation | Thermotropic polyester-carbonates containing 2,2-dimethyl-1,3-propanediol |
US4612360A (en) * | 1985-10-11 | 1986-09-16 | Monsanto Company | Melt polymerization process for preparing polyarylates |
US4816552A (en) * | 1987-03-30 | 1989-03-28 | Kolon Industries, Inc. | Aromatic polyester compounds and process for preparing them |
US5248305A (en) * | 1989-08-04 | 1993-09-28 | Cordis Corporation | Extruded tubing and catheters having helical liquid crystal fibrils |
US5156785A (en) * | 1991-07-10 | 1992-10-20 | Cordis Corporation | Extruded tubing and catheters having increased rotational stiffness |
US5149757A (en) * | 1990-05-01 | 1992-09-22 | University Of Massachusetts At Amherst | Process to synthesize liquid crystalline polyesters |
US5196502A (en) * | 1991-11-05 | 1993-03-23 | Eastman Kodak Company | Method for the preparation of multiply-branched aromatic polyesters |
US5321118A (en) * | 1993-09-30 | 1994-06-14 | Eastman Chemical Company | 1-acetoacetamido-2,3-propane diol monomer and polyesters prerpared therefrom |
US5638172A (en) * | 1994-05-27 | 1997-06-10 | Eastman Chemical Company | On-line quantitative analysis of chemical compositions by raman spectrometry |
US5714567A (en) * | 1996-02-15 | 1998-02-03 | Council Of Scientific & Ind. Research | Process for the preparation of aromatic polyesters |
US6043322A (en) * | 1996-12-28 | 2000-03-28 | Eastman Chemical Company | Clear polycarbonate and polyester blends |
EP0850970A3 (en) * | 1996-12-28 | 1999-02-24 | Eastman Chemical Company | Process for preparing the polycarbonate of 2,2,4,4-tetramethyl-1,3-cyclobutanediol |
US6114474A (en) * | 1996-12-28 | 2000-09-05 | Eastman Chemical Company | Process for deactivating polycarbonate catalyst residues |
EP0850914A1 (en) * | 1996-12-28 | 1998-07-01 | Eastman Chemical Company | Carbonic acid 3-methoxycarbonyl-oxl-2,2,4,4-tetramethyl-cyclo-butyl ester methyl ester and method making therefor |
EP0857743A3 (en) * | 1996-12-28 | 1999-02-24 | Eastman Chemical Company | Process for preparing poly(2,2,4,4-tetramethyl-1,3-cyclobutylene carbonate) |
US5955565A (en) * | 1996-12-28 | 1999-09-21 | Eastman Chemical Company | Polyesters from terephthalic acid, 2,2,4,4-tetramethyl-1,3-cyclobutanediol and ethylene glycol |
US6005059A (en) * | 1996-12-28 | 1999-12-21 | Eastman Chemical Company | Clear polycarbonate and polyester blends |
US6011124A (en) * | 1996-12-28 | 2000-01-04 | Eastman Chemical Company | Blends of bisphenol a polycarbonate and polyesters |
US5942585A (en) * | 1996-12-28 | 1999-08-24 | Eastman Chemical Company | Polycarbonate and polyester blends |
US6037424A (en) * | 1996-12-28 | 2000-03-14 | Eastman Chemical Company | Clear blends of polycarbonates and polyesters |
US6180748B1 (en) | 1996-12-30 | 2001-01-30 | Eastman Chemical Company | Process for deactivating alkali metal catalyst residues in poly(2,2,4,4-tetramethyl-1,3-cyclobutylene carbonate residues |
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 |
US20020082360A1 (en) * | 2000-11-03 | 2002-06-27 | Conn Roy Lee | Films and articles formed from blends of polycarbonate and polyester |
US6569957B2 (en) | 2000-11-03 | 2003-05-27 | Eastman Chemical Company | Blends of polycarbonate and polyester and sheets and films formed therefrom |
US6723768B2 (en) | 2002-03-27 | 2004-04-20 | Eastman Chemical Company | Polyester/polycarbonate blends with reduced yellowness |
EP2329856B1 (en) | 2003-04-29 | 2019-07-24 | Eastman Chemical Company | Containers comprising polyester compositions which comprise cyclobutanediol |
US8119761B2 (en) | 2005-06-17 | 2012-02-21 | Eastman Chemical Company | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and high glass transition temperature and articles made therefrom |
US7704605B2 (en) | 2006-03-28 | 2010-04-27 | Eastman Chemical Company | Thermoplastic articles comprising cyclobutanediol having a decorative material embedded therein |
US7226985B2 (en) * | 2005-07-12 | 2007-06-05 | Eastman Chemical Company | Polyester-polycarbonate compositions |
US8193302B2 (en) | 2005-10-28 | 2012-06-05 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol and certain phosphate thermal stabilizers, and/or reaction products thereof |
ATE505500T1 (de) | 2005-10-28 | 2011-04-15 | Eastman Chem Co | Polyesterzusammensetzungen mit cyclobutandiol mit hoher glasübergangstemperatur und daraus hergestellte artikel |
ATE444981T1 (de) | 2005-10-28 | 2009-10-15 | Eastman Chem Co | Aus 2,2,4,4-tetramethyl-1,3-cyclobutandiol und 1, 4-cyclohexandimethanol gebildete polyesterzusammensetzungen umfassendes restaurantgeschirr |
EP2444440B1 (en) | 2005-10-28 | 2019-12-18 | Eastman Chemical Company | Polyester compositions containing cyclobutanediol having high glass transition temperature and articles made therefrom |
US9598533B2 (en) | 2005-11-22 | 2017-03-21 | Eastman Chemical Company | Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom |
US7737246B2 (en) | 2005-12-15 | 2010-06-15 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol, cyclohexanedimethanol, and ethylene glycol and manufacturing processes therefor |
US9169388B2 (en) | 2006-03-28 | 2015-10-27 | Eastman Chemical Company | Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof |
US20080085390A1 (en) | 2006-10-04 | 2008-04-10 | Ryan Thomas Neill | Encapsulation of electrically energized articles |
US8287991B2 (en) * | 2006-10-04 | 2012-10-16 | Eastman Chemical Company | Using branched polymers to control the dimensional stability of articles in the lamination process |
US20080103235A1 (en) * | 2006-11-01 | 2008-05-01 | Wesley Raymond Hale | Clear blends of bisphenol a polycarbonate and copolyesters |
CA2705870A1 (en) | 2007-11-21 | 2009-06-04 | Eastman Chemical Company | Plastic baby bottles, other blow molded articles, and processes for their manufacture |
US8501287B2 (en) | 2007-11-21 | 2013-08-06 | Eastman Chemical Company | Plastic baby bottles, other blow molded articles, and processes for their manufacture |
US8980389B2 (en) * | 2008-01-14 | 2015-03-17 | Eastman Chemical Company | Copolyesters and blends with improved recyclability, processes for their manufacture, and articles prepared therefrom |
US8198371B2 (en) | 2008-06-27 | 2012-06-12 | Eastman Chemical Company | Blends of polyesters and ABS copolymers |
US9289795B2 (en) | 2008-07-01 | 2016-03-22 | Precision Coating Innovations, Llc | Pressurization coating systems, methods, and apparatuses |
US20100015456A1 (en) | 2008-07-16 | 2010-01-21 | Eastman Chemical Company | Thermoplastic formulations for enhanced paintability toughness and melt process ability |
US8895654B2 (en) | 2008-12-18 | 2014-11-25 | Eastman Chemical Company | Polyester compositions which comprise spiro-glycol, cyclohexanedimethanol, and terephthalic acid |
US9029460B2 (en) * | 2009-02-06 | 2015-05-12 | Stacey James Marsh | Coating compositions containing acrylic and aliphatic polyester blends |
US8168721B2 (en) * | 2009-02-06 | 2012-05-01 | Eastman Chemical Company | Coating compositions containing tetramethyl cyclobutanediol |
US8163850B2 (en) * | 2009-02-06 | 2012-04-24 | Eastman Chemical Company | Thermosetting polyester coating compositions containing tetramethyl cyclobutanediol |
US20100210775A1 (en) | 2009-02-13 | 2010-08-19 | Eastman Chemical Company | Reinforced polyester compositions having improved toughness |
US8734909B2 (en) | 2010-03-10 | 2014-05-27 | Eastman Chemical Company | Methods and apparatus for coating substrates |
US8604105B2 (en) | 2010-09-03 | 2013-12-10 | Eastman Chemical Company | Flame retardant copolyester compositions |
US8394997B2 (en) | 2010-12-09 | 2013-03-12 | Eastman Chemical Company | Process for the isomerization of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
US8420869B2 (en) | 2010-12-09 | 2013-04-16 | Eastman Chemical Company | Process for the preparation of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
US8420868B2 (en) | 2010-12-09 | 2013-04-16 | Eastman Chemical Company | Process for the preparation of 2,2,4,4-tetraalkylcyclobutane-1,3-diols |
US9150006B2 (en) | 2011-06-23 | 2015-10-06 | Eastman Chemical Company | Lamination process optimization utilizing neopentyl glycol-modified polyesters |
US10000588B2 (en) | 2011-07-28 | 2018-06-19 | Eastman Chemical Company | Coating for the inner surface of plastic bottles for protection against degradation from volatile organic compounds |
US20130095271A1 (en) | 2011-10-14 | 2013-04-18 | Eastman Chemical Company | Polyester compositions containing furandicarboxylic acid or an ester thereof, ethylene glycol and cyclohexanedimethanol |
US20130217830A1 (en) | 2012-02-16 | 2013-08-22 | Eastman Chemical Company | Clear Semi-Crystalline Articles with Improved Heat Resistance |
US9616457B2 (en) | 2012-04-30 | 2017-04-11 | Innovative Coatings, Inc. | Pressurization coating systems, methods, and apparatuses |
WO2013172812A1 (en) | 2012-05-14 | 2013-11-21 | Bayer Materialscience Ag | Multi-layer film with improved modulus properties |
US8623483B1 (en) | 2012-10-23 | 2014-01-07 | Eastman Chemical Company | Copolyesters containing neopentyl glycol and 2,2,4,4-tetraalkyl 1,3-cyclobutanediol |
US9127122B2 (en) | 2012-10-23 | 2015-09-08 | Eastman Chemical Company | Copolyesters containing neopentyl glycol and 2,2,4,4-tetraalkyl 1,3-cyclobutanediol |
US8865261B2 (en) | 2012-12-06 | 2014-10-21 | Eastman Chemical Company | Extrusion coating of elongated substrates |
US10329393B2 (en) | 2012-12-12 | 2019-06-25 | Eastman Chemical Company | Copolysters plasticized with polymeric plasticizer for shrink film applications |
US9920526B2 (en) | 2013-10-18 | 2018-03-20 | Eastman Chemical Company | Coated structural members having improved resistance to cracking |
US9744707B2 (en) | 2013-10-18 | 2017-08-29 | Eastman Chemical Company | Extrusion-coated structural members having extruded profile members |
US9447257B2 (en) | 2014-02-10 | 2016-09-20 | Eastman Chemical Company | Polymers combined with certain additives and devices made thererom |
US10711133B2 (en) | 2014-12-12 | 2020-07-14 | Eastman Chemical Company | Flame retardant copolyester compositions |
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 |
US11072684B2 (en) | 2016-08-18 | 2021-07-27 | Eastman Chemical Company | Polyester compositions which comprise tetramethylcyclobutandiol and ethylene glycol, with improved catalyst system |
WO2018035341A1 (en) | 2016-08-18 | 2018-02-22 | Eastman Chemical Company | Polyester compositions which comprise tetramethylcyclobutanediol and ethylene glycol for calendering |
US11427688B2 (en) | 2017-04-17 | 2022-08-30 | Eastman Chemical Company | Copolyesters plasticized with polymeric plasticizer |
US10308799B2 (en) | 2017-06-21 | 2019-06-04 | Eastman Chemical Company | Fiber reinforced polyvinyl chloride and copolyester compositions and articles made using these compositions |
US11512198B2 (en) | 2017-06-21 | 2022-11-29 | Eastman Chemical Company | Polyvinyl chloride and copolyester compositions and articles made using these compositions |
KR102470432B1 (ko) | 2017-10-30 | 2022-11-23 | 이스트만 케미칼 컴파니 | 저밀도 공극-함유 필름 |
US10543656B2 (en) | 2018-01-11 | 2020-01-28 | Eastman Chemical Company | Tough shrinkable films |
EP3863832A1 (en) | 2018-10-08 | 2021-08-18 | Eastman Chemical Company | Crystallizable shrinkable films and thermoformable sheets made from resin blends |
CN112789155B (zh) | 2018-10-08 | 2024-03-15 | 伊士曼化工公司 | 由反应器级树脂制成的可结晶收缩膜和可热成形片材 |
US11198782B2 (en) | 2018-12-14 | 2021-12-14 | Eastman Chemical Company | Polyvinyl chloride, polycarbonate and copolyester compositions and articles made using these compositions |
US11198781B2 (en) | 2018-12-14 | 2021-12-14 | Eastman Chemical Company | Polyvinyl chloride, polycarbonate and copolyester compositions and articles made using these compositions |
CN113785002A (zh) | 2019-05-10 | 2021-12-10 | 伊士曼化工公司 | 来自共聚酯和再生pet的共混物的可再生模制品 |
WO2020231781A1 (en) | 2019-05-10 | 2020-11-19 | Eastman Chemical Company | Recyclable extrusion blow molded articles from blends of copolyesters and recycled pet |
US11365357B2 (en) | 2019-05-24 | 2022-06-21 | Eastman Chemical Company | Cracking C8+ fraction of pyoil |
CN114423803A (zh) | 2019-07-29 | 2022-04-29 | 伊士曼化工公司 | 用来自热解与甲醇分解的再循环单体制备聚酯的方法 |
WO2021016911A1 (en) | 2019-07-31 | 2021-02-04 | Eastman Chemical (China) Co., Ltd. | Polyester articles having an improved hard-coat |
CN114787233A (zh) | 2019-10-08 | 2022-07-22 | 伊士曼化工公司 | 用于具有回收料含量的可结晶反应器级树脂的催化剂体系 |
EP4041796A1 (en) | 2019-10-08 | 2022-08-17 | Eastman Chemical Company | Catalyst systems for crystallizable reactor grade resins |
BR112022007592A2 (pt) | 2019-10-25 | 2022-07-05 | Eastman Chem Co | Processo para produzir uma composição de poliéster, filme retrátil, filme vazio, artigo moldado, artigo termoformável, filme ou folha extrudada, filme soprado, artigo moldado por extrusão por sopro, e, método para introduzir ou estabelecer conteúdo de reciclagem em um poliéster |
US11319262B2 (en) | 2019-10-31 | 2022-05-03 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
US11945998B2 (en) | 2019-10-31 | 2024-04-02 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
EP4103644A1 (en) | 2020-02-10 | 2022-12-21 | Eastman Chemical Company | Flame retardant copolyester compositions |
WO2021163124A1 (en) | 2020-02-10 | 2021-08-19 | Eastman Chemical Company | Non-halogenated flame retardant copolyester compositions |
EP4132991A1 (en) | 2020-04-06 | 2023-02-15 | Eastman Chemical Company | Crystallizable shrinkable films and thermoformable sheets made from resin blends |
JP2023522001A (ja) | 2020-04-13 | 2023-05-26 | イーストマン ケミカル カンパニー | 多層の熱成形可能なフィルム及びシートから作られた熱充填可能な物品 |
JP2023530126A (ja) | 2020-06-15 | 2023-07-13 | イーストマン ケミカル カンパニー | ポリ塩化ビニル、ポリカーボネートおよびコポリエステル組成物、ならびにこれらの組成物を使用して作製された物品 |
EP4225827A1 (en) | 2020-10-08 | 2023-08-16 | Eastman Chemical Company | Shrinkable polyester films |
US20240011217A1 (en) | 2020-11-09 | 2024-01-11 | Eastman Chemical Company | Washing machine door assembly |
WO2022108783A1 (en) | 2020-11-17 | 2022-05-27 | Eastman Chemical Company | Molded articles for use with terpene containing oils |
US20240117106A1 (en) | 2020-12-18 | 2024-04-11 | Eastman Chemical Company | Polyester compositions comprising tetramethyl cyclobutanediol and 1,4-cyclohexanedimethanol having an improved catalyst system comprising titanium and zinc |
WO2023275618A1 (en) | 2021-06-30 | 2023-01-05 | Bostik Sa | (co)polyester resins for use as heat seal layers for containers and films incorporating such layers to seal and reseal containers |
CN117813337A (zh) | 2021-08-03 | 2024-04-02 | 伊士曼化工公司 | 阻燃共聚酯组合物 |
EP4384564A1 (en) | 2021-08-12 | 2024-06-19 | Eastman Chemical Company | Molded articles for use with degredation chemicals |
TW202315906A (zh) | 2021-10-08 | 2023-04-16 | 美商伊士曼化學公司 | 具有減少收縮之可收縮聚酯膜 |
CN118215648A (zh) | 2021-10-25 | 2024-06-18 | 伊士曼化工公司 | 回收聚(对苯二甲酸乙二酯)的低温工艺 |
WO2023091542A1 (en) | 2021-11-22 | 2023-05-25 | Eastman Chemical Company | Process for making recyclable copolyesters articles with living hinges |
WO2023091544A1 (en) | 2021-11-22 | 2023-05-25 | Eastman Chemical Company | Process for making recyclable copolyesters articles with living hinges |
WO2023091539A1 (en) | 2021-11-22 | 2023-05-25 | Eastman Chemical Company | Recyclable copolyesters articles with living hinges |
WO2023091540A1 (en) | 2021-11-22 | 2023-05-25 | Eastman Chemical Company | Recyclable copolyesters articles with living hinges |
WO2023114062A1 (en) | 2021-12-16 | 2023-06-22 | Eastman Chemical Company | Polyester compositions comprising cyclohexanedimethanol or 2,2,4,4-tetramethyl-1,3-cyclobutanediol with improved catalyst systems therefor |
WO2023178221A1 (en) | 2022-03-18 | 2023-09-21 | Eastman Chemical Company | Multilayer crystallizable shrinkable film and sheet |
WO2023196829A1 (en) | 2022-04-06 | 2023-10-12 | Eastman Chemical Company | Multilayer shrinkable polyester films with improved toughness |
WO2023244953A1 (en) | 2022-06-13 | 2023-12-21 | Eastman Chemical Company | Copolyesters compositions having low coefficient of friction |
WO2023244956A1 (en) | 2022-06-13 | 2023-12-21 | Eastman Chemical Company | Copolyester compositions having low coefficient of friction |
WO2024026335A1 (en) | 2022-07-27 | 2024-02-01 | Eastman Chemical Company | Thermosetting powder coating compositions |
WO2024026334A1 (en) | 2022-07-27 | 2024-02-01 | Eastman Chemical Company | Thermosetting powder coating compositions |
WO2024054767A1 (en) | 2022-09-06 | 2024-03-14 | Eastman Chemical Company | Copolyester blow molded articles with a transparent view stripe |
WO2024092080A1 (en) | 2022-10-28 | 2024-05-02 | Eastman Chemical Company | Recycleable hot melt adhesive copolyester compositions |
-
0
- BE BE794938D patent/BE794938A/xx unknown
-
1972
- 1972-02-02 US US00222977A patent/US3772405A/en not_active Expired - Lifetime
- 1972-12-15 DE DE2261503A patent/DE2261503C3/de not_active Expired
-
1973
- 1973-01-05 CA CA160,691A patent/CA1008588A/en not_active Expired
- 1973-02-01 GB GB511773A patent/GB1402973A/en not_active Expired
- 1973-02-02 FR FR7303638A patent/FR2170166B1/fr not_active Expired
- 1973-02-02 JP JP48013639A patent/JPS4888193A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
US3772405A (en) | 1973-11-13 |
DE2261503B2 (de) | 1978-02-09 |
DE2261503A1 (de) | 1973-08-09 |
JPS4888193A ( ) | 1973-11-19 |
FR2170166A1 ( ) | 1973-09-14 |
GB1402973A (en) | 1975-08-13 |
BE794938A (fr) | 1973-08-02 |
FR2170166B1 ( ) | 1976-09-10 |
CA1008588A (en) | 1977-04-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE2261503C3 (de) | Verfahren zur Herstellung eines zweiten Polyesters aus einem ersten Polyester | |
DE2342415A1 (de) | Neue, lineare homo- und copolyester auf basis von tere- und/oder isophthalsaeure | |
EP0041496B1 (de) | Verfahren zur Herstellung aromatischer Polyester | |
DE2703376A1 (de) | Verfahren zur herstellung aromatischer copolyester | |
EP0346735B1 (de) | Verfahren zur kontinuierlichen Herstellung von linearen thermoplastischen Polyestern | |
EP0245691B1 (de) | Verwendung von Folien aus Polykondensaten | |
EP0189073B1 (de) | Thermotrope aromatische Polyester mit hoher thermischer Stabilität, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Formkörpern, Filamenten, Fasern und Folien | |
US3651172A (en) | Method for preparing linear block copolyesters and product produced thereby | |
DE2744648C2 ( ) | ||
EP0097861B1 (de) | Aromatische Polyestercarbonate mit hoher Kerbschlagzähigkeit und Verfahren zu ihrer Herstellung | |
EP0201830B1 (de) | Verfahren zur Herstellung von Copolyphosphonaten mit hoher Kerbschlagzähigkeit | |
DE2342431A1 (de) | Neue, lineare homo- und copolyester auf basis von terephthal- und/oder isophthalsaeure | |
DE1495265B2 (de) | Verfahren zur herstellung linearer, thermoplastischer polyester mit einfriertemperatur ueber 100 grad c | |
US2960493A (en) | Fiber and film-forming polycondensates | |
EP0064971A2 (de) | Hochmolekularer aromatischer Polyester, Verfahren zur Herstellung von Folien aus diesen Polyestern und Folie aus diesen Polyestern, ein elektrischer Leiter mit einer Isolierung aus diesen Polyestern und Verfahren zur Herstellung solcher Isolierungen | |
DE2533675A1 (de) | Lineare copolyester auf basis von terephthal- und/oder isophthalsaeure | |
DE2453448A1 (de) | Lineare, thermoplastische polyester und verfahren zu ihrer herstellung | |
DE3009911A1 (de) | Verfahren zur herstellung von copolyestern nach dem schmelzphasenprozess | |
DE2720844A1 (de) | Thermoplastische polyester | |
DE2601958A1 (de) | Loesungspolymerisationsverfahren fuer die herstellung von linearen aromatischen polyestern | |
DE2720835A1 (de) | Thermoplastische polyester und verfahren zu ihrer herstellung | |
DE1445394C3 (de) | Verfahren zur Herstellung von voll standig aromatischen Polyestern | |
AT247613B (de) | Verfahren zur Herstellung von linearen, thermoplastischen Mischpolyestern | |
DE1495667A1 (de) | Verfahren zur Herstellung linearer Polykondensate | |
DE2243488A1 (de) | Verfahren zur herstellung von thermoplastischen copolyesterformmassen |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C3 | Grant after two publication steps (3rd publication) | ||
EHJ | Ceased/non-payment of the annual fee |