TWI279409B - Process for making poly(ethylene-co-isosorbide) terephthalate polymer - Google Patents
Process for making poly(ethylene-co-isosorbide) terephthalate polymer Download PDFInfo
- Publication number
- TWI279409B TWI279409B TW92116130A TW92116130A TWI279409B TW I279409 B TWI279409 B TW I279409B TW 92116130 A TW92116130 A TW 92116130A TW 92116130 A TW92116130 A TW 92116130A TW I279409 B TWI279409 B TW I279409B
- Authority
- TW
- Taiwan
- Prior art keywords
- isosorbide
- polymer
- ethylene glycol
- temperature
- mixture
- Prior art date
Links
- 229960002479 isosorbide Drugs 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 54
- 229920000642 polymer Polymers 0.000 title claims description 41
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 160
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims abstract description 58
- 239000000835 fiber Substances 0.000 claims abstract description 13
- 230000003287 optical effect Effects 0.000 claims abstract description 7
- 229920002959 polymer blend Polymers 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 49
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 12
- -1 poly(ethyl ester) Polymers 0.000 claims description 12
- 238000006068 polycondensation reaction Methods 0.000 claims description 12
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000008188 pellet Substances 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 239000000975 dye Substances 0.000 claims description 9
- 235000019441 ethanol Nutrition 0.000 claims description 9
- 238000002835 absorbance Methods 0.000 claims description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910002804 graphite Inorganic materials 0.000 claims description 7
- 239000010439 graphite Substances 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 229930182558 Sterol Natural products 0.000 claims description 5
- 239000006096 absorbing agent Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims description 5
- 229960001826 dimethylphthalate Drugs 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 150000003432 sterols Chemical class 0.000 claims description 5
- 235000003702 sterols Nutrition 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- 239000012963 UV stabilizer Substances 0.000 claims description 3
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- MPCYPRXRVWZKGF-UHFFFAOYSA-J tetrasodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(N=NC3=CC=C(C=C3)C3=CC=C(C=C3)N=NC3=C(C=C4C=C(C=C(C4=C3O)N)S([O-])(=O)=O)S([O-])(=O)=O)=C(O)C2=C1N MPCYPRXRVWZKGF-UHFFFAOYSA-J 0.000 claims description 3
- 206010036790 Productive cough Diseases 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229940011182 cobalt acetate Drugs 0.000 claims description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 210000003802 sputum Anatomy 0.000 claims description 2
- 208000024794 sputum Diseases 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 3
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims 2
- 239000001263 FEMA 3042 Substances 0.000 claims 2
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims 2
- 229940033123 tannic acid Drugs 0.000 claims 2
- 235000015523 tannic acid Nutrition 0.000 claims 2
- 229920002258 tannic acid Polymers 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 239000002250 absorbent Substances 0.000 claims 1
- 230000002745 absorbent Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 239000006229 carbon black Substances 0.000 claims 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 claims 1
- 229940093476 ethylene glycol Drugs 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 150000005846 sugar alcohols Chemical class 0.000 claims 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract description 5
- 229920001577 copolymer Polymers 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 2
- 239000000956 alloy Substances 0.000 abstract 1
- 229910045601 alloy Inorganic materials 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 62
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000000155 melt Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000014755 Eruca sativa Nutrition 0.000 description 3
- 244000024675 Eruca sativa Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-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
- OMIHCBSQSYMFDP-UHFFFAOYSA-N 3-hydroxy-5-methoxy-3-methoxycarbonyl-5-oxopentanoic acid Chemical compound COC(=O)CC(O)(CC(O)=O)C(=O)OC OMIHCBSQSYMFDP-UHFFFAOYSA-N 0.000 description 1
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 101150055297 SET1 gene Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 210000000078 claw Anatomy 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- WOYXQCUBRRZMPN-UHFFFAOYSA-N ethene;hydrochloride Chemical compound Cl.C=C.C=C.C=C WOYXQCUBRRZMPN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
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- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 102200017272 rs28931576 Human genes 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- DVUVKWLUHXXIHK-UHFFFAOYSA-N tetraazanium;tetrahydroxide Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[OH-].[OH-].[OH-].[OH-] DVUVKWLUHXXIHK-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- 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
-
- 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
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/171,924 US6656577B1 (en) | 2002-06-14 | 2002-06-14 | Process for making poly(ethylene-co-isosorbide) terephthalate polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200401791A TW200401791A (en) | 2004-02-01 |
| TWI279409B true TWI279409B (en) | 2007-04-21 |
Family
ID=29549481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW92116130A TWI279409B (en) | 2002-06-14 | 2003-06-13 | Process for making poly(ethylene-co-isosorbide) terephthalate polymer |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6656577B1 (enExample) |
| JP (1) | JP4368791B2 (enExample) |
| KR (1) | KR100967289B1 (enExample) |
| CN (1) | CN1675282B (enExample) |
| MY (1) | MY135718A (enExample) |
| TW (1) | TWI279409B (enExample) |
| WO (1) | WO2003106531A1 (enExample) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6914120B2 (en) * | 2002-11-13 | 2005-07-05 | Eastman Chemical Company | Method for making isosorbide containing polyesters |
| US7052764B2 (en) * | 2002-12-19 | 2006-05-30 | E. I. Du Pont De Nemours And Company | Shaped articles comprising poly[(trimethylene-co-dianhydrosugar ester) dicarboxylate] or poly(trimethylene-co-dianhydro-dicarboxylate with improved stability |
| US7179881B2 (en) * | 2003-09-19 | 2007-02-20 | Eastman Chemical Company | Process for heating PET pellet feed to a solid stating process by heat exchange with hot solid stated pellets |
| US7642032B2 (en) * | 2003-10-22 | 2010-01-05 | Ricoh Company, Limited | Toner, developer, image forming apparatus and image forming method |
| JP4692057B2 (ja) * | 2004-04-22 | 2011-06-01 | 宇部興産株式会社 | 新規ポリオキサレート |
| EP1838770A1 (en) * | 2004-09-14 | 2007-10-03 | E.I. Dupont De Nemours And Company | Processes for making low color poly(ethylene-co-isosorbide) terephthalate polymers |
| JP4276267B2 (ja) * | 2004-11-30 | 2009-06-10 | 旭化成ケミカルズ株式会社 | 重縮合ポリマー及びその成形体の製造方法及び製造装置 |
| US8293162B2 (en) * | 2004-11-30 | 2012-10-23 | Asahi Kasei Chemicals Corporation | Method and apparatus for producing molded product |
| US20070010650A1 (en) | 2005-06-17 | 2007-01-11 | Crawford Emmett D | Tough amorphous polyester compositions |
| US20100184940A1 (en) * | 2005-03-02 | 2010-07-22 | Eastman Chemical Company | Polyester Compositions Which Comprise Cyclobutanediol and Certain Thermal Stabilizers, and/or Reaction Products Thereof |
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| US20060199871A1 (en) * | 2005-03-02 | 2006-09-07 | Hale Wesley R | Multilayered, transparent articles and a process for their preparation |
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| US8895654B2 (en) * | 2008-12-18 | 2014-11-25 | Eastman Chemical Company | Polyester compositions which comprise spiro-glycol, cyclohexanedimethanol, and terephthalic acid |
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| DE102010045778A1 (de) | 2010-09-17 | 2012-03-22 | Polyprec Gmbh | Neue amphiphile Polykondensate und ihre Verwendung in Kombination mit Polyester oder polyesterhaltigen Oberflächen |
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| KR101796764B1 (ko) | 2011-01-31 | 2017-11-10 | 에스케이케미칼주식회사 | 공중합 폴리에스테르 수지 조성물 및 그 제조방법 |
| CN102250330B (zh) * | 2011-05-05 | 2013-03-13 | 常州大学 | 利用源于生物质资源单体合成的高透明共聚酯及制备方法 |
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| US9434813B2 (en) | 2012-12-07 | 2016-09-06 | Mitsubishi Rayon Co., Ltd. | Polyester resin for toners, method for producing same, and toner |
| CN103044671B (zh) * | 2012-12-19 | 2014-10-08 | 中国纺织科学研究院 | 一种含二失水糖醇共聚酯的制备方法 |
| EP2999733B1 (en) * | 2013-05-21 | 2025-12-31 | Ester Industries Limited | HEAT-RESISTANT POLYETHYLENE TEREPHLATE AND ITS PREPARATION PROCESS |
| KR102049410B1 (ko) | 2013-06-11 | 2019-11-27 | 에스케이케미칼 주식회사 | 자동차, 전기전자기기, 가전기기, 사무기기 또는 생활용품용 부품 |
| KR102049411B1 (ko) * | 2013-06-11 | 2019-11-27 | 에스케이케미칼 주식회사 | 내약품성이 우수한 고분자 수지 조성물 |
| CA2941489C (en) | 2014-03-11 | 2022-05-31 | Furanix Technologies B.V. | Polyester comprising 2,5-furandicarboxylate moieties and ethylene glycolresidues and method for making such polyester |
| TWI506055B (zh) * | 2014-12-31 | 2015-11-01 | Far Eastern New Century Corp | Preparation of modified copolyester |
| JP6936802B6 (ja) * | 2015-12-24 | 2021-10-20 | エスケー ディスカバリー カンパニー リミテッドＳＫ Ｄｉｓｃｏｖｅｒｙ Ｃｏ．， Ｌｔｄ． | ポリエステル樹脂、その製造方法およびこれから形成された樹脂成形品 |
| KR102302973B1 (ko) * | 2016-01-29 | 2021-09-16 | 효성티앤씨 주식회사 | 투명성이 높은 비결정성 폴리에틸렌테레프탈레이트 중합물의 제조방법 |
| KR20170090707A (ko) * | 2016-01-29 | 2017-08-08 | 주식회사 효성 | 고점도 아이소소바이드 폴리에틸렌테레프탈레이트 중합물의 제조방법 |
| KR102553772B1 (ko) * | 2016-04-06 | 2023-07-07 | 에스케이케미칼 주식회사 | 폴리에스테르 수지 |
| KR101694189B1 (ko) | 2016-06-17 | 2017-01-23 | (주)씨티에스 | 폴리에스테르 공중합체 및 그 제조방법 |
| WO2018221944A1 (ko) | 2017-05-31 | 2018-12-06 | 에스케이케미칼 주식회사 | 폴리에스테르 수지， 이의 제조 방법 및 이로부터 형성된 수지 성형품 |
| KR102568693B1 (ko) | 2017-06-02 | 2023-08-21 | 에스케이케미칼 주식회사 | 폴리에스테르 섬유, 이의 제조 방법 및 이로부터 형성된 성형체 |
| WO2018236111A2 (ko) | 2017-06-22 | 2018-12-27 | 에스케이케미칼주식회사 | 폴리에스테르 용기, 이의 제조 방법 |
| KR102684863B1 (ko) | 2017-06-26 | 2024-07-15 | 에스케이케미칼 주식회사 | 폴리에스테르 필름 및 이의 제조 방법 |
| CN107394264B (zh) * | 2017-07-12 | 2020-03-20 | 安徽大学 | 耐高温的水性聚氨酯固态电解质及其制备方法 |
| FR3086662B1 (fr) * | 2018-10-01 | 2021-11-05 | Roquette Freres | Procede de cristallisation d'un polyester comprenant au moins un motif 1,4 : 3,6-dianhydrohexitol. |
| TWI800981B (zh) * | 2021-11-16 | 2023-05-01 | 南亞塑膠工業股份有限公司 | 聚合物樹脂及其製造方法 |
| CN117659368A (zh) * | 2022-08-31 | 2024-03-08 | 科泽新材料股份有限公司 | 一种制备peit共聚酯的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3651017A (en) * | 1967-12-29 | 1972-03-21 | Kurashiki Rayon Co | Process for the preparation of polyesters |
| US5912307A (en) | 1996-05-03 | 1999-06-15 | Bp Amoco Corporation | Polyester compositions |
| US6025061A (en) * | 1998-04-23 | 2000-02-15 | Hna Holdings, Inc. | Sheets formed from polyesters including isosorbide |
| US6063464A (en) | 1998-04-23 | 2000-05-16 | Hna Holdings, Inc. | Isosorbide containing polyesters and methods for making same |
| US6063495A (en) | 1998-04-23 | 2000-05-16 | Hna Holdings, Inc. | Polyester fiber and methods for making same |
| US5959066A (en) | 1998-04-23 | 1999-09-28 | Hna Holdings, Inc. | Polyesters including isosorbide as a comonomer and methods for making same |
| US5958581A (en) | 1998-04-23 | 1999-09-28 | Hna Holdings, Inc. | Polyester film and methods for making same |
| US6140422A (en) * | 1998-04-23 | 2000-10-31 | E.I. Dupont De Nemours And Company | Polyesters including isosorbide as a comonomer blended with other thermoplastic polymers |
| US6063465A (en) | 1998-04-23 | 2000-05-16 | Hna Holdings, Inc. | Polyester container and method for making same |
| US6126992A (en) * | 1998-04-23 | 2000-10-03 | E.I. Dupont De Nemours And Company | Optical articles comprising isosorbide polyesters and method for making same |
-
2002
- 2002-06-14 US US10/171,924 patent/US6656577B1/en not_active Expired - Lifetime
-
2003
- 2003-06-12 JP JP2004513358A patent/JP4368791B2/ja not_active Expired - Fee Related
- 2003-06-12 CN CN038193248A patent/CN1675282B/zh not_active Expired - Lifetime
- 2003-06-12 WO PCT/US2003/018622 patent/WO2003106531A1/en not_active Ceased
- 2003-06-12 KR KR1020047020336A patent/KR100967289B1/ko not_active Expired - Lifetime
- 2003-06-13 TW TW92116130A patent/TWI279409B/zh not_active IP Right Cessation
- 2003-06-13 MY MYPI20032209A patent/MY135718A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR100967289B1 (ko) | 2010-07-01 |
| JP4368791B2 (ja) | 2009-11-18 |
| MY135718A (en) | 2008-06-30 |
| US20030232959A1 (en) | 2003-12-18 |
| CN1675282B (zh) | 2010-05-26 |
| KR20050012278A (ko) | 2005-01-31 |
| US6656577B1 (en) | 2003-12-02 |
| CN1675282A (zh) | 2005-09-28 |
| JP2005530000A (ja) | 2005-10-06 |
| TW200401791A (en) | 2004-02-01 |
| WO2003106531A1 (en) | 2003-12-24 |
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