AU2005265323C1 - Copolyetherester compositions containing hydroxyalkanoic acids and shaped articles produced therefrom - Google Patents
Copolyetherester compositions containing hydroxyalkanoic acids and shaped articles produced therefrom Download PDFInfo
- Publication number
- AU2005265323C1 AU2005265323C1 AU2005265323A AU2005265323A AU2005265323C1 AU 2005265323 C1 AU2005265323 C1 AU 2005265323C1 AU 2005265323 A AU2005265323 A AU 2005265323A AU 2005265323 A AU2005265323 A AU 2005265323A AU 2005265323 C1 AU2005265323 C1 AU 2005265323C1
- Authority
- AU
- Australia
- Prior art keywords
- acid
- mole percent
- glycol
- dimethyl
- lactate
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims description 127
- 239000002253 acid Substances 0.000 title claims description 116
- 150000007513 acids Chemical class 0.000 title description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 383
- -1 poly(alkylene ether Chemical compound 0.000 claims description 309
- 239000011541 reaction mixture Substances 0.000 claims description 205
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 171
- 125000003118 aryl group Chemical group 0.000 claims description 169
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 162
- 238000000034 method Methods 0.000 claims description 158
- 229920000642 polymer Polymers 0.000 claims description 154
- 239000000758 substrate Substances 0.000 claims description 129
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 127
- 230000008569 process Effects 0.000 claims description 115
- 229960000448 lactic acid Drugs 0.000 claims description 85
- 239000000463 material Substances 0.000 claims description 85
- 239000004310 lactic acid Substances 0.000 claims description 79
- 235000014655 lactic acid Nutrition 0.000 claims description 79
- 238000000576 coating method Methods 0.000 claims description 78
- 239000011087 paperboard Substances 0.000 claims description 73
- 239000000945 filler Substances 0.000 claims description 66
- 239000000835 fiber Substances 0.000 claims description 62
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 57
- 239000006260 foam Substances 0.000 claims description 50
- 239000011248 coating agent Substances 0.000 claims description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 43
- 239000002245 particle Substances 0.000 claims description 42
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 40
- 239000000123 paper Substances 0.000 claims description 38
- 239000011521 glass Substances 0.000 claims description 36
- 239000006085 branching agent Substances 0.000 claims description 35
- 229920001634 Copolyester Polymers 0.000 claims description 31
- 239000003638 chemical reducing agent Substances 0.000 claims description 30
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 27
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 26
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 26
- 229940035437 1,3-propanediol Drugs 0.000 claims description 26
- 229920002472 Starch Polymers 0.000 claims description 26
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 26
- 235000019698 starch Nutrition 0.000 claims description 24
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 20
- 239000008107 starch Substances 0.000 claims description 20
- 229920002678 cellulose Polymers 0.000 claims description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 239000007983 Tris buffer Substances 0.000 claims description 17
- 125000005907 alkyl ester group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 17
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 claims description 15
- 239000001913 cellulose Substances 0.000 claims description 15
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 15
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 14
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 14
- 229940065514 poly(lactide) Drugs 0.000 claims description 14
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 13
- 229920003023 plastic Polymers 0.000 claims description 13
- 239000004033 plastic Substances 0.000 claims description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 10
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 claims description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 8
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 8
- 239000004753 textile Substances 0.000 claims description 8
- MJHNUUNSCNRGJE-UHFFFAOYSA-N trimethyl benzene-1,2,4-tricarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(C(=O)OC)=C1 MJHNUUNSCNRGJE-UHFFFAOYSA-N 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
- 150000002334 glycols Chemical class 0.000 claims description 7
- GJBXIPOYHVMPQJ-UHFFFAOYSA-N hexadecane-1,16-diol Chemical compound OCCCCCCCCCCCCCCCCO GJBXIPOYHVMPQJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000010030 laminating Methods 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 7
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 6
- YVOWOLLEVWDWOH-SCSAIBSYSA-N 2-hydroxyethyl (2r)-2-hydroxypropanoate Chemical compound C[C@@H](O)C(=O)OCCO YVOWOLLEVWDWOH-SCSAIBSYSA-N 0.000 claims description 6
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 claims description 6
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims description 6
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 6
- LZCLXQDLBQLTDK-SCSAIBSYSA-N ethyl (2R)-lactate Chemical compound CCOC(=O)[C@@H](C)O LZCLXQDLBQLTDK-SCSAIBSYSA-N 0.000 claims description 6
- LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 claims description 6
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 claims description 6
- 229940116333 ethyl lactate Drugs 0.000 claims description 6
- 229960004275 glycolic acid Drugs 0.000 claims description 6
- 229940057867 methyl lactate Drugs 0.000 claims description 6
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 5
- ZZERATCPJYKORA-YFKPBYRVSA-N 3-hydroxypropyl (2s)-2-hydroxypropanoate Chemical compound C[C@H](O)C(=O)OCCCO ZZERATCPJYKORA-YFKPBYRVSA-N 0.000 claims description 5
- ZZERATCPJYKORA-UHFFFAOYSA-N 3-hydroxypropyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OCCCO ZZERATCPJYKORA-UHFFFAOYSA-N 0.000 claims description 5
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 5
- JSPHZDHJXBRGFI-UHFFFAOYSA-N 4-hydroxybutyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OCCCCO JSPHZDHJXBRGFI-UHFFFAOYSA-N 0.000 claims description 5
- ZHVZTRUUPYIJTQ-UHFFFAOYSA-N bis(3-hydroxypropyl) benzene-1,4-dicarboxylate Chemical compound OCCCOC(=O)C1=CC=C(C(=O)OCCCO)C=C1 ZHVZTRUUPYIJTQ-UHFFFAOYSA-N 0.000 claims description 5
- MRLFFZIIRRKXBJ-UHFFFAOYSA-N bis(4-hydroxybutyl) benzene-1,4-dicarboxylate Chemical compound OCCCCOC(=O)C1=CC=C(C(=O)OCCCCO)C=C1 MRLFFZIIRRKXBJ-UHFFFAOYSA-N 0.000 claims description 5
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 claims description 5
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims description 5
- LPEKGGXMPWTOCB-GSVOUGTGSA-N methyl (R)-lactate Chemical compound COC(=O)[C@@H](C)O LPEKGGXMPWTOCB-GSVOUGTGSA-N 0.000 claims description 5
- 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 claims description 5
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 claims description 5
- 229920001610 polycaprolactone Polymers 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- 239000004417 polycarbonate Substances 0.000 claims description 5
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 5
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 4
- HVXQNGWJNMRWIP-UHFFFAOYSA-N 2,5-dihydroxypentanoic acid Chemical compound OCCCC(O)C(O)=O HVXQNGWJNMRWIP-UHFFFAOYSA-N 0.000 claims description 4
- GPSQXVSPHYKFTO-UHFFFAOYSA-N 2,6-dihydroxyhexanoic acid Chemical compound OCCCCC(O)C(O)=O GPSQXVSPHYKFTO-UHFFFAOYSA-N 0.000 claims description 4
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 claims description 4
- YVOWOLLEVWDWOH-BYPYZUCNSA-N 2-hydroxyethyl (2s)-2-hydroxypropanoate Chemical compound C[C@H](O)C(=O)OCCO YVOWOLLEVWDWOH-BYPYZUCNSA-N 0.000 claims description 4
- KXYYLPXFBMMURF-UHFFFAOYSA-N 3,5,6-tris(2-hydroxyethyl)benzene-1,2,4-tricarboxylic acid Chemical compound OCCC1=C(CCO)C(C(O)=O)=C(C(O)=O)C(CCO)=C1C(O)=O KXYYLPXFBMMURF-UHFFFAOYSA-N 0.000 claims description 4
- ZZERATCPJYKORA-RXMQYKEDSA-N 3-hydroxypropyl (2r)-2-hydroxypropanoate Chemical compound C[C@@H](O)C(=O)OCCCO ZZERATCPJYKORA-RXMQYKEDSA-N 0.000 claims description 4
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 claims description 4
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 claims description 4
- ULCGAWLDXLEIIR-UHFFFAOYSA-N bis(2-hydroxyethyl) benzene-1,3-dicarboxylate Chemical compound OCCOC(=O)C1=CC=CC(C(=O)OCCO)=C1 ULCGAWLDXLEIIR-UHFFFAOYSA-N 0.000 claims description 4
- ILHNTBVQTUBETD-UHFFFAOYSA-N bis(4-hydroxybutyl) benzene-1,3-dicarboxylate Chemical compound OCCCCOC(=O)C1=CC=CC(C(=O)OCCCCO)=C1 ILHNTBVQTUBETD-UHFFFAOYSA-N 0.000 claims description 4
- 239000011111 cardboard Substances 0.000 claims description 4
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000539 dimer Substances 0.000 claims description 4
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011888 foil Substances 0.000 claims description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 claims description 4
- 229960002479 isosorbide Drugs 0.000 claims description 4
- FAFKIXPMYWNHGF-UHFFFAOYSA-N methyl 4-[(4-methoxycarbonylphenyl)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CC1=CC=C(C(=O)OC)C=C1 FAFKIXPMYWNHGF-UHFFFAOYSA-N 0.000 claims description 4
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 claims description 4
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 claims description 4
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 claims description 4
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 4
- 238000009466 skin packaging Methods 0.000 claims description 4
- XLKZJJVNBQCVIX-UHFFFAOYSA-N tetradecane-1,14-diol Chemical compound OCCCCCCCCCCCCCCO XLKZJJVNBQCVIX-UHFFFAOYSA-N 0.000 claims description 4
- UFYGCFHQAXXBCF-UHFFFAOYSA-N 2,4-dihydroxybutanoic acid Chemical compound OCCC(O)C(O)=O UFYGCFHQAXXBCF-UHFFFAOYSA-N 0.000 claims description 3
- KTFJPMPXSYUEIP-UHFFFAOYSA-N 3-benzoylphthalic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C(O)=O KTFJPMPXSYUEIP-UHFFFAOYSA-N 0.000 claims description 3
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 claims description 3
- 229920003232 aliphatic polyester Polymers 0.000 claims description 3
- SZQOVRVUEBDBJG-UHFFFAOYSA-N bis(3-hydroxypropyl) benzene-1,3-dicarboxylate Chemical compound OCCCOC(=O)C1=CC=CC(C(=O)OCCCO)=C1 SZQOVRVUEBDBJG-UHFFFAOYSA-N 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 239000004745 nonwoven fabric Substances 0.000 claims description 3
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 claims description 3
- 229920006280 packaging film Polymers 0.000 claims description 3
- 239000012785 packaging film Substances 0.000 claims description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
- 239000011094 fiberboard Substances 0.000 claims description 2
- 229920005615 natural polymer Polymers 0.000 claims description 2
- 229920006327 polystyrene foam Polymers 0.000 claims description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- GSOQHYDVLMGLDS-UHFFFAOYSA-N 3,5,6-tris(3-hydroxypropyl)benzene-1,2,4-tricarboxylic acid Chemical compound OCCCC1=C(CCCO)C(C(O)=O)=C(C(O)=O)C(CCCO)=C1C(O)=O GSOQHYDVLMGLDS-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UWTATZPHSA-M (R)-lactate Chemical compound C[C@@H](O)C([O-])=O JVTAAEKCZFNVCJ-UWTATZPHSA-M 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 claims 1
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- 238000010998 test method Methods 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- TUUQISRYLMFKOG-UHFFFAOYSA-N trihexyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCOC(=O)CC(C(=O)OCCCCCC)(OC(C)=O)CC(=O)OCCCCCC TUUQISRYLMFKOG-UHFFFAOYSA-N 0.000 description 1
- GWVUTNGDMGTPFE-UHFFFAOYSA-N trihexyl 2-butanoyloxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCOC(=O)CC(C(=O)OCCCCCC)(OC(=O)CCC)CC(=O)OCCCCCC GWVUTNGDMGTPFE-UHFFFAOYSA-N 0.000 description 1
- APVVRLGIFCYZHJ-UHFFFAOYSA-N trioctyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCC)CC(=O)OCCCCCCCC APVVRLGIFCYZHJ-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000007666 vacuum forming Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/10—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of paper or cardboard
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising 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
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- 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
- 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
- C08L67/025—Polyesters derived from dicarboxylic acids and dihydroxy compounds containing polyether sequences
-
- 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
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/12—Polyester-amides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyesters Or Polycarbonates (AREA)
- Laminated Bodies (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/888,225 | 2004-07-09 | ||
| US10/888,225 US7144972B2 (en) | 2004-07-09 | 2004-07-09 | Copolyetherester compositions containing hydroxyalkanoic acids and shaped articles produced therefrom |
| PCT/US2005/024385 WO2006010061A1 (en) | 2004-07-09 | 2005-07-08 | Copolyetherester compositions containing hydroxyalkanoic acids and shaped articles produced therefrom |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2005265323A1 AU2005265323A1 (en) | 2006-01-26 |
| AU2005265323B2 AU2005265323B2 (en) | 2010-07-08 |
| AU2005265323C1 true AU2005265323C1 (en) | 2011-01-06 |
Family
ID=35124602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005265323A Ceased AU2005265323C1 (en) | 2004-07-09 | 2005-07-08 | Copolyetherester compositions containing hydroxyalkanoic acids and shaped articles produced therefrom |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7144972B2 (enExample) |
| EP (1) | EP1789470B1 (enExample) |
| JP (1) | JP4950043B2 (enExample) |
| CN (1) | CN1980976B (enExample) |
| AU (1) | AU2005265323C1 (enExample) |
| WO (1) | WO2006010061A1 (enExample) |
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|---|---|---|---|---|
| DE10144717A1 (de) * | 2001-09-11 | 2003-03-27 | Bakelite Ag | Verfahren zur Herstellung von Isolationsplatten und Bindemittelgemisch hierzu |
| US7357985B2 (en) * | 2005-09-19 | 2008-04-15 | E.I. Du Pont De Nemours And Company | High crimp bicomponent fibers |
| US7669348B2 (en) * | 2006-10-10 | 2010-03-02 | Rdp Company | Apparatus, method and system for treating sewage sludge |
| GB2443625A (en) * | 2006-11-08 | 2008-05-14 | Tate & Lyle Plc | Lactic acid polymer |
| US20080108759A1 (en) * | 2006-11-08 | 2008-05-08 | Sodergard Nils D A | Lactic Acid Polymers |
| PL1923423T3 (pl) * | 2006-11-14 | 2013-11-29 | Sa Minera Catalano Aragonesa | Proces wprowadzania dodatków do włókien syntetycznych, włókien sztucznych i polimerów o specjalnych własnościach |
| US20080122141A1 (en) * | 2006-11-29 | 2008-05-29 | Bryan Bedal | Sinterable Powder |
| JP5055294B2 (ja) * | 2006-12-06 | 2012-10-24 | 帝人化成株式会社 | 眼鏡レンズ |
| US20090131625A1 (en) * | 2007-11-21 | 2009-05-21 | Kurian Joseph V | Processes for making elastomeric polyester esters from post-consumer polyester |
| US20090047523A1 (en) * | 2007-08-13 | 2009-02-19 | Keedy Jr Vincent W | Production of discrete shaped article |
| US7951438B2 (en) * | 2007-12-10 | 2011-05-31 | Toray Plastics (America), Inc. | Biaxially oriented polylactic acid film with high barrier |
| WO2009076541A1 (en) * | 2007-12-11 | 2009-06-18 | Toray Plastics (America), Inc. | Process to produce biaxially oriented polylactic acid film at high transverse orientation rates |
| US20090186177A1 (en) * | 2008-01-22 | 2009-07-23 | Eastman Chemical Company | Polyester melt phase products and process for making the same |
| US8071690B2 (en) | 2008-01-23 | 2011-12-06 | Tate & Lyle Ingredients Americas Llc | Lactic acid based compositions with enhanced properties |
| WO2009142978A1 (en) | 2008-05-19 | 2009-11-26 | Molecon, Inc. | Synthesis of polyesters with precisely sequenced two or more structural units |
| WO2010014785A1 (en) * | 2008-07-30 | 2010-02-04 | E. I. Du Pont De Nemours And Company | Heat resistant thermoplastic articles including co-stabilizers |
| US9314999B2 (en) * | 2008-08-15 | 2016-04-19 | Toray Plastics (America), Inc. | Biaxially oriented polylactic acid film with high barrier |
| WO2010030599A2 (en) * | 2008-09-09 | 2010-03-18 | Molecon, Inc. | Novel polymers with hydroxyl acid blocks |
| US8016980B2 (en) | 2008-11-25 | 2011-09-13 | Dixie Consumer Products Llc | Paper products |
| US20100143546A1 (en) * | 2008-12-09 | 2010-06-10 | The Coca-Cola Company | Container and composition for enhanced gas barrier properties |
| US8110265B2 (en) | 2008-12-09 | 2012-02-07 | The Coca-Cola Company | Pet container and compositions having enhanced mechanical properties and gas barrier properties |
| US9150004B2 (en) | 2009-06-19 | 2015-10-06 | Toray Plastics (America), Inc. | Biaxially oriented polylactic acid film with improved heat seal properties |
| US9221213B2 (en) * | 2009-09-25 | 2015-12-29 | Toray Plastics (America), Inc. | Multi-layer high moisture barrier polylactic acid film |
| EP2480710B1 (en) | 2009-09-25 | 2018-01-24 | Toray Plastics (America) , Inc. | Multi-layer high moisture barrier polylactic acid film and its method of forming |
| US9492962B2 (en) | 2010-03-31 | 2016-11-15 | Toray Plastics (America), Inc. | Biaxially oriented polylactic acid film with reduced noise level and improved moisture barrier |
| WO2011123165A1 (en) | 2010-03-31 | 2011-10-06 | Toray Plastics (America), Inc. | Biaxially oriented polyactic acid film with reduced noise level |
| US9056950B2 (en) | 2010-07-23 | 2015-06-16 | Ticona Gmbh | Composite polymeric articles formed from extruded sheets containing a liquid crystal polymer |
| KR101769560B1 (ko) * | 2011-03-29 | 2017-08-18 | 에스케이케미칼주식회사 | 젖산과 아이소소바이드가 공중합된 폴리에스테르 수지 및 그 제조방법 |
| KR101775620B1 (ko) * | 2011-04-06 | 2017-09-07 | 에스케이케미칼주식회사 | 코팅용 폴리에스테르 바인더 수지 및 이를 함유하는 코팅 조성물 |
| 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 |
| ITMI20111273A1 (it) * | 2011-07-08 | 2013-01-09 | Fond Cariplo | Polimeri ramificati di acido lattico ad alta viscosita' nel fuso e alta shear sensitivity e loro nano compositi |
| US20130158168A1 (en) * | 2011-12-19 | 2013-06-20 | E I Du Pont De Nemours And Company | Aliphatic-aromatic copolyetheresters |
| US9394402B2 (en) | 2012-12-20 | 2016-07-19 | Dow Global Technologies Llc | Glycolide-based polyesters made with isosorbide |
| US9580594B2 (en) | 2012-12-20 | 2017-02-28 | Dow Global Technologies Llc | FDCA-based polyesters |
| EP2934890B1 (en) | 2012-12-20 | 2018-09-26 | Dow Global Technologies LLC | Multilayer films of fdca-based polyesters |
| CN104968716A (zh) | 2012-12-20 | 2015-10-07 | 陶氏环球技术有限责任公司 | 乙交酯基聚酯 |
| EP4357434A3 (en) | 2014-09-26 | 2024-11-20 | Renmatix, Inc. | Adhesive compositions comprising type-ii cellulose |
| EP3201264A1 (en) * | 2014-10-01 | 2017-08-09 | Colormatrix Holdings Inc. | Nucleating agent additive compositions for polymeric materials |
| US10400105B2 (en) | 2015-06-19 | 2019-09-03 | The Research Foundation For The State University Of New York | Extruded starch-lignin foams |
| EP3559081B1 (en) * | 2016-12-22 | 2023-11-22 | Solvay SA | Glycolic acid polymer |
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| CN111363328B (zh) * | 2020-05-12 | 2022-08-23 | 山西浩博瑞新材料有限公司 | 一种高强度阻燃性壳聚糖-聚乳酸复合材料及其制法 |
| JP7654095B2 (ja) * | 2021-02-10 | 2025-03-31 | キャボット コーポレイション | 熱可塑性エラストマーの製造方法及びそれにより得られるポリマー複合体 |
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| CN117757048B (zh) * | 2023-12-20 | 2025-03-11 | 中国地质大学（武汉） | 一种超支化聚己内酯-聚乳酸共聚物及其制备方法和应用 |
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2005
- 2005-07-08 CN CN2005800226399A patent/CN1980976B/zh not_active Expired - Fee Related
- 2005-07-08 EP EP05772855A patent/EP1789470B1/en not_active Revoked
- 2005-07-08 JP JP2007520565A patent/JP4950043B2/ja not_active Expired - Fee Related
- 2005-07-08 WO PCT/US2005/024385 patent/WO2006010061A1/en not_active Ceased
- 2005-07-08 AU AU2005265323A patent/AU2005265323C1/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| US7144972B2 (en) | 2006-12-05 |
| US20060009611A1 (en) | 2006-01-12 |
| EP1789470A1 (en) | 2007-05-30 |
| AU2005265323B2 (en) | 2010-07-08 |
| AU2005265323A1 (en) | 2006-01-26 |
| WO2006010061A1 (en) | 2006-01-26 |
| CN1980976A (zh) | 2007-06-13 |
| JP4950043B2 (ja) | 2012-06-13 |
| CN1980976B (zh) | 2010-08-11 |
| JP2008506020A (ja) | 2008-02-28 |
| EP1789470B1 (en) | 2012-10-31 |
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