JP2022506851A - ポリマー組成物 - Google Patents
ポリマー組成物 Download PDFInfo
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- JP2022506851A JP2022506851A JP2021524463A JP2021524463A JP2022506851A JP 2022506851 A JP2022506851 A JP 2022506851A JP 2021524463 A JP2021524463 A JP 2021524463A JP 2021524463 A JP2021524463 A JP 2021524463A JP 2022506851 A JP2022506851 A JP 2022506851A
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- acid
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- 229920000642 polymer Polymers 0.000 title claims abstract description 163
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 229920000954 Polyglycolide Polymers 0.000 claims abstract description 55
- 239000004633 polyglycolic acid Substances 0.000 claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 229920000728 polyester Polymers 0.000 claims abstract description 7
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 58
- -1 polyethylene isophthalate Polymers 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 29
- 229920005989 resin Polymers 0.000 claims description 25
- 239000011347 resin Substances 0.000 claims description 25
- 150000001261 hydroxy acids Chemical class 0.000 claims description 24
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 18
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 17
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 229920001169 thermoplastic Polymers 0.000 claims description 16
- 239000004416 thermosoftening plastic Substances 0.000 claims description 16
- 239000000155 melt Substances 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 13
- 150000003077 polyols Chemical class 0.000 claims description 12
- 229920008790 Amorphous Polyethylene terephthalate Polymers 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 229920001225 polyester resin Polymers 0.000 claims description 6
- 239000004645 polyester resin Substances 0.000 claims description 6
- 229920001634 Copolyester Polymers 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 claims description 4
- 239000011112 polyethylene naphthalate Substances 0.000 claims description 4
- 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 4
- 238000001816 cooling Methods 0.000 claims description 3
- 238000001746 injection moulding Methods 0.000 claims description 3
- 238000003303 reheating Methods 0.000 claims description 3
- MFJDFPRQTMQVHI-UHFFFAOYSA-N 3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound O=C1OCOC(=O)C2=CC=C1C=C2 MFJDFPRQTMQVHI-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 2
- 229920005668 polycarbonate resin Polymers 0.000 claims description 2
- 239000004431 polycarbonate resin Substances 0.000 claims description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 2
- 229920005990 polystyrene resin Polymers 0.000 claims description 2
- 241001272567 Hominoidea Species 0.000 claims 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 229920002215 polytrimethylene terephthalate Polymers 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract 1
- 229920006125 amorphous polymer Polymers 0.000 description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 238000010438 heat treatment Methods 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 14
- 230000004888 barrier function Effects 0.000 description 13
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 238000000113 differential scanning calorimetry Methods 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 230000004927 fusion Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 6
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 4
- 229920008651 Crystalline Polyethylene terephthalate Polymers 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 3
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- FMHKPLXYWVCLME-UHFFFAOYSA-N 4-hydroxy-valeric acid Chemical compound CC(O)CCC(O)=O FMHKPLXYWVCLME-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 244000178870 Lavandula angustifolia Species 0.000 description 2
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002564 cardiac stress test Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000001102 lavandula vera Substances 0.000 description 2
- 235000018219 lavender Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical group C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000005498 phthalate group Chemical class 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 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 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- GSJAEHIASJBUKQ-UHFFFAOYSA-N 1-methyl-1-[2-(1-methylcyclohexyl)propan-2-yl]cyclohexane Chemical group CC1(CCCCC1)C(C)(C)C1(CCCCC1)C GSJAEHIASJBUKQ-UHFFFAOYSA-N 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
- WXSVCGWHWWPQKF-UHFFFAOYSA-N 2,3-bis(2-hydroxyethyl)cyclohexan-1-ol Chemical compound OCCC1CCCC(O)C1CCO WXSVCGWHWWPQKF-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- WUIXEIPAPIJUGW-UHFFFAOYSA-N 2-[1,1-bis(2-hydroxyphenyl)propyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C=1C(=CC=CC=1)O)(CC)C1=CC=CC=C1O WUIXEIPAPIJUGW-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- XFDQLDNQZFOAFK-UHFFFAOYSA-N 2-benzoyloxyethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOC(=O)C1=CC=CC=C1 XFDQLDNQZFOAFK-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- CCXLOQVMDTWRSP-UHFFFAOYSA-N 2-cyclohexylpropan-2-ylcyclohexane Chemical group C1CCCCC1C(C)(C)C1CCCCC1 CCXLOQVMDTWRSP-UHFFFAOYSA-N 0.000 description 1
- ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 2-dodecanoyloxyethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCC ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 0.000 description 1
- RSROEZYGRKHVMN-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.CCC(CO)(CO)CO RSROEZYGRKHVMN-UHFFFAOYSA-N 0.000 description 1
- MQUMNTKHZXNYGW-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;propane-1,3-diol Chemical compound OCCCO.CCC(CO)(CO)CO MQUMNTKHZXNYGW-UHFFFAOYSA-N 0.000 description 1
- FZLHLGUYHAXYNA-UHFFFAOYSA-N 2-fluoro-3,3-bis(fluorooxycarbonyl)-2-(trifluoromethyl)butanedioic acid Chemical compound OC(=O)C(F)(C(F)(F)F)C(C(O)=O)(C(=O)OF)C(=O)OF FZLHLGUYHAXYNA-UHFFFAOYSA-N 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical group OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- YHXNHYKKDRMEEH-UHFFFAOYSA-N 3-(2-hydroxyethoxy)propane-1,2-diol Chemical compound OCCOCC(O)CO YHXNHYKKDRMEEH-UHFFFAOYSA-N 0.000 description 1
- WQYPVEKEHDLOBS-UHFFFAOYSA-N 3-(2-hydroxypropoxy)propane-1,2-diol Chemical compound CC(O)COCC(O)CO WQYPVEKEHDLOBS-UHFFFAOYSA-N 0.000 description 1
- RBQRPOWGQURLEU-UHFFFAOYSA-N 3-[(3-carboxyphenyl)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CC=2C=C(C=CC=2)C(O)=O)=C1 RBQRPOWGQURLEU-UHFFFAOYSA-N 0.000 description 1
- LJPXCZADJYRIMX-UHFFFAOYSA-N 3-[2-(3-carboxyphenoxy)phenoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=CC=CC=2)OC=2C=C(C=CC=2)C(O)=O)=C1 LJPXCZADJYRIMX-UHFFFAOYSA-N 0.000 description 1
- CVPWXYQTHJVBDP-UHFFFAOYSA-N 3-[2-(3-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C(C=2C=C(C=CC=2)C(O)=O)(C(F)(F)F)C(F)(F)F)=C1 CVPWXYQTHJVBDP-UHFFFAOYSA-N 0.000 description 1
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-
- 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
- B32B2250/00—Layers arrangement
- B32B2250/05—5 or more layers
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- 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
- B32B2250/00—Layers arrangement
- B32B2250/24—All layers being polymeric
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- 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
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-
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
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- B32B2307/7242—Non-permeable
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Abstract
Description
本出願は、米国で2018年11月12日に出願された米国特許出願第62/759960号及び欧州で2019年3月20日に出願された欧州特許出願第19163927.7号に基づく優先権を主張し、これらの出願の全内容は、あらゆる目的のために参照により本明細書に組み込まれる。
i)少なくとも1種のポリグリコール酸ポリマー[ポリマー(PGA)]と、
ii)ポリマー(PGA)及びポリマー(APES)の合計重量に対して少なくとも0.10重量%且つ最大45重量%の量で組成物(M)中に存在する、少なくとも1種のアモルファスポリエステル[ポリマー(APES)]と、
を含有するポリマー組成物[組成物(M)]に関する。
(i)グリコール酸(GA)と、
(ii)1つのみのヒドロキシル基と1つのみのカルボン酸基とを有する、GAとは異なる任意選択的な少なくとも1種のヒドロキシル酸[ヒドロキシ酸(A)]であって、GAとヒドロキシ酸(A)の合計のモル数に対して有利には最大5モル%である[ヒドロキシ酸(A)]と、
(iii)グリコール酸とヒドロキシ酸(A)(存在する場合)のヒドロキシル基の総数に対して、そのヒドロキシル基の数が有利には少なくとも0.050%、有利には最大0.750%であるような量の、少なくとも3つのヒドロキシル基を含み且つカルボン酸基を含まない少なくとも1種のポリオール[ポリオール(H)]と、
(iv)グリコール酸とヒドロキシ酸(A)(存在する場合)のヒドロキシル基の総数に対して、そのカルボキシル基の数が有利には少なくとも0.050%、有利には最大0.750%であるような量の、少なくとも2つのカルボン酸基を含み且つヒドロキシル基を含まない任意選択的な少なくとも1種のポリ酸[ポリ酸(O)]と、
の重縮合に由来する単位を含む。
- 具体的にはグリセロール、トリメチロールプロパン、トリメチロールブタン、2,3-ジ(2’-ヒドロキシエチル)-シクロヘキサン-1-オール、ヘキサン-1,2,6-トリオール、1,1,1-トリス(ヒドロキシメチル)エタン、3-(2’-ヒドロキシエトキシ)プロパン-1,2-ジオール、3-(2’-ヒドロキシプロポキシ)-プロパン-1,2-ジオール、2-(2’-ヒドロキシエトキシ)-ヘキサン-1,2-ジオール、6-(2’ヒドロキシプロポキシ)-ヘキサン-1,2-ジオール、1,1,1-トリス-[(2’-ヒドロキシエトキシ)-メチルエタン、1,1,1-トリス-[(2’-ヒドロキシプロポキシ)-メチル-プロパン、1,1,1-トリス-(4’-ヒドロキシフェニル)エタン、1,1,1-トリス-(ヒドロキシフェニル)-プロパン、1,1,5-トリス-(ヒドロキシフェニル)-3-メチルペンタン、トリメチロールプロパンエトキシレート、トリメチロールプロパンプロポキシレート、トリス(ヒドロキシメチル)アミノメタンからなる群から選択されるトリオール、
- 具体的にはジグリセロール、ジ(トリメチロールプロパン)、ペンタエリスリトール、1,1,4-トリス-(ジヒドロキシフェニル)-ブタンからなる群から選択されるテトラオール、
- 5つのヒドロキシル基を含むポリオール、具体的にはトリグリセロール、
- 6つのヒドロキシル基を含むポリオール、特にジペンタエリスリトール、及び
- 8つのヒドロキシル基を含むポリオール、特にトリペンタエリスリトール
からなる群から選択され得る。
- プロパン-1,2,3-トリカルボン酸(別名トリカルバリル酸);
- エタン-1,1,2,2テトラカルボン酸;
- ブタン-1,2,3,4テトラカルボン酸;
- ペンタン-1,2,4,5-テトラカルボン酸
である。
- 1,2,3,4-シクロブタンテトラカルボン酸;
- 2,2,6,6-テトラ-(カルボキシエチル)シクロヘキサノン;
- (+)-(18-クラウン-6)-2,3,11,12-テトラカルボン酸;
- シクロペンタン-1,2,3,4テトラカルボン酸;
- シクロヘキサン-1,2,4,5テトラカルボン酸;
- シクロヘキサン-2,3,5,6テトラカルボン酸;
- 3-エチルシクロヘキサン-1,2,4,5テトラカルボン酸;
- 1-メチル-3-エチルシクロヘキサン-3-(1,2)5,6テトラカルボン酸;
- 1-エチルシクロヘキサン-1-(1,2),3,4テトラカルボン酸;
- 1-プロピルシクロヘキサン-1-(2,3),3,4テトラカルボン酸;
- 1,3-ジプロピルシクロヘキサン-1-(2,3),3-(2,3)テトラカルボン酸;
- ジシクロヘキシル-3,4,3’,4’テトラカルボン酸
である。
- ピロメリット酸(1,2,4,5-ベンゼンテトラカルボン酸);
- トリメシン酸(1,3,5-ベンゼントリカルボン酸);
- トリメリット酸(1,3,4-ベンゼントリカルボン酸);
- ベンゾフェノン-3,3’,4,4’-テトラカルボン酸;
- テトラヒドロフラン-2,3,4,5-テトラカルボン酸;
- 4,4’-(ヘキサフルオロイソプロピリデン)ジフタル酸;
- 4,4’-オキシジフタル酸無水物;
- 4,4’-(4,4’-イソプロピリデンジフェノキシ)ビス(フタル酸);
- 3,3’,4,4’-ビフェニルテトラカルボン酸;
- 2,3,3’,4’-ビフェニルテトラカルボン酸;
- 2,2’,3,3’-ビフェニルテトラカルボン酸;
- 1,2,5,6-ナフタレンテトラカルボン酸;
- 2,3,6,7-ナフタレンテトラカルボン酸;
- ペリレン-3,4,9,10テトラカルボン酸;
- プロパン 2,2-ビス(3,4-ジカルボキシフェニル)酸;
- エタン 1,1-ビス(2,3-ジカルボキシフェニル)酸;
- エタン 1,1-ビス(3,4-ジカルボキシフェニル)酸;
- フェナントレン-1,8,9,10-テトラカルボン酸;
- テトラヒドロフラン-2,3,4,5-テトラカルボン酸;
- 3,3’,4,4’-ベンゾフェノンテトラカルボン酸;
- 2,2’,3,3’-ベンゾフェノンテトラカルボン酸;
- 2,3,5,6-ピリジンテトラカルボン酸;
- 3,3’,4,4’-テトラフェニルシランテトラカルボン酸;
- 2,2’-ビス(3,4-ビカルボキシフェニル)ヘキサフルオロプロパンテトラカルボン酸;
- 2,2-ビス(3,4-ジカルボキシフェニル)スルホン酸;
- 4,4’-(ヘキサフルオロイソプロピリデン)ジフタル酸;
- 3,3’,4,4’-ジフェニルスルホンテトラカルボン酸;
- エチレングリコールビストリメリット酸;
- ヒドロキノンジフタル酸;
- ピラジン-2,3,5,6-テトラカルボン酸;
- チオフェン-2,3,4,5-テトラカルボン酸
である。
RHm-COOH (式C-1)
(式中、RHmは、1つ以上の炭素原子、特には3つ以上の炭素原子を有する一価の脂肪族基である)。
(i)溶融物から加工することにより、上で詳述した組成物(M)の少なくとも1つの層と、ポリグリコール酸ポリマーとは異なる熱可塑性プラスチックの少なくとも1つの層とを含む多層樹脂ラミネートを形成すること;
(ii)多層樹脂ラミネートを延伸して多層延伸製品を製造すること;
を含む。
b-PGAは、メタンスルホン酸(GAlkgあたり1.350g)の存在下、GAと、トリメチロールプロパン(GA100モルに対して0.14モル)と、イソフタル酸(GA100モルに対して0.21モル)との混合物から得られる、国際公開第2018/115008号パンフレット(SOLVAY S.A.)の教示に従って製造される分岐PGAである。b-PGAは、ISO 11357-3(欧州規格)又はASTM D3418(米国規格)に準拠したDSCによって、10mgのサンプルで窒素下で10℃/分で20℃から270℃までの1回目の加熱中に共に測定される、Tmについては236℃、Tgについては45℃の溶融温度(Tm)及びガラス転移温度(Tg)によって特徴付けられる。b-PGAは、ASTM D4440-08に準拠して260℃の温度で平行板を使用して10秒-1のせん断速度(10rad/秒の振動速度)で測定される527Pa×秒の溶融粘度によっても特徴付けられる。
以下の実施例に記載の組成物を、表1に規定の温度プロファイルで運転される二軸押出機Clextral BC21(直径21mm、長さ43D、9バレルゾーン、ゾーン7で真空、窒素流下の2つの重量計量フィーダー及び1つのホッパー、2つのロンドホールを有するダイ、水浴及び空気乾燥機、ペレタイザー)を使用して混錬し、ペレットの形態でこれらの混合物を回収する。
結晶化のピーク温度(Tc)及び融解熱(ΔH)は、ISO 11357-3(欧州規格)又はASTM D3418(米国規格)に準拠した10°K/分でのDSCによって、10mgのサンプルで窒素下で10℃/分で20℃から270℃までの1回目の加熱中に測定した。
以下の実施例に記載されている組成物それぞれの10グラムのペレットを、栓をしたガラス瓶中の250mlの脱塩水の中に入れた。38℃のオーブン中でエージングした後、水の導電率の測定を24時間おきに行い、水の導電率の増加(グリコール酸の放出による)に必要な時間量を耐加水分解性として採用した。
以下の実施例に記載の通りに組成物からフィルムを製造した。
酸素透過の測定は、ASTM D3985に従って行った。
耐剥離性の測定は、上述した通りに製造したフィルム(サンプルのサイズ:25×200mm)に対するT剥離試験ASTM D1876に従って行った。フィルムサンプルの一端を65℃の苛性ソーダ溶液に浸して層Bを層Cから分離し、フィルムの2つの部分を引張ジョーでクランプ固定した。
上で詳述した配合手順に従って、90重量%のb-PGAと10重量%のATBPEとを含有する組成物を調製した。
上で詳述した配合手順に従って、90重量%のb-PGAと10重量%のCPETとを含有する組成物を調製した。
上で詳述した配合手順に従って、100重量%のb-PGAを含有する組成物を調製した。
Claims (15)
- i)少なくとも1種のポリグリコール酸ポリマー[ポリマー(PGA)]と、
ii)ポリマー(PGA)及びポリマー(APES)の合計重量に対して少なくとも0.10重量%且つ最大45重量%の量で組成物(M)中に存在する、少なくとも1種のアモルファスポリエステル[ポリマー(APES)]と、
を含有するポリマー組成物[組成物(M)]。 - ポリマー(PGA)が分岐ポリグリコール酸ポリマー[ポリマー(b-PGA)]である、請求項1に記載の組成物(M)。
- ポリマー(b-PGA)が:
(i)グリコール酸(GA)と、
(ii)1つのみのヒドロキシル基と1つのみのカルボン酸基とを有する、GAとは異なる任意選択的な少なくとも1種のヒドロキシル酸[ヒドロキシ酸(A)]であって、GAとヒドロキシ酸(A)の合計のモル数に対して有利には最大5モル%である[ヒドロキシ酸(A)]と、
(iii)グリコール酸と前記ヒドロキシ酸(A)(存在する場合)のヒドロキシル基の総数に対して、そのヒドロキシル基の数が有利には少なくとも0.050%、有利には最大0.750%であるような量の、少なくとも3つのヒドロキシル基を含み且つカルボン酸基を含まない少なくとも1種のポリオール[ポリオール(H)]と、
(iv)グリコール酸と前記ヒドロキシ酸(A)(存在する場合)のヒドロキシル基の総数に対して、そのカルボキシル基の数が有利には少なくとも0.050%、有利には最大0.750%であるような量の、少なくとも2つのカルボン酸基を含み且つヒドロキシル基を含まない任意選択的な少なくとも1種のポリ酸[ポリ酸(O)]と、
の重縮合に由来する単位を含む、請求項2に記載の組成物(M)。 - 前記ポリマー(APES)が、アモルファステレフタレートベースのコポリエステル[ポリマー(ATBPE)]、アモルファスポリエチレンイソフタレート[ポリマー(APEI)]、アモルファスポリエチレンナフタレート[ポリマー(APEN)]、アモルファスポリエチレンフラノエート[ポリマー(APEF)]、及びアモルファスポリトリメチレンフランジカルボキシレート[ポリマー(APTF)]から選択される、請求項1~3のいずれか一項に記載の組成物(M)。
- 前記ポリマー(APES)がポリマー(ATBPE)である、請求項4に記載の組成物(M)。
- ポリマー(ATBPE)が、アモルファスポリエチレンテレフタレート[ポリマー(APET)]、アモルファスポリシクロヘキシレンジメチレンテレフタレート[ポリマー(APCT)]、アモルファスポリブチレンテレフタレート[ポリマー(APBT)]、及びアモルファスポリトリメチレンテレフタレート[ポリマー(APTT)]から選択される、請求項5に記載の組成物(M)。
- ポリマー(APES)が、ポリマー(PGA)とポリマー(APES)の合計重量に対して少なくとも0.50重量%且つ最大25重量%の量で組成物(M)中に存在する、請求項1~6のいずれか一項に記載の組成物(M)。
- ポリマー(APES)が、ポリマー(PGA)とポリマー(APES)の合計重量に対して少なくとも1重量%且つ最大20重量%の量で組成物(M)中に存在する、請求項1~7のいずれか一項に記載の組成物(M)。
- ポリマー(PGA)と、ポリマー(APES)と、任意選択的な追加の成分とを混合することを含む、請求項1~8のいずれか一項に記載の組成物(M)の製造方法。
- 前記方法が、ポリマー(PGA)と、ポリマー(APES)と、任意選択的な追加の成分とを溶融状態で混合する工程を含む、請求項9に記載の方法。
- (i)溶融物から加工することにより、請求項1~8のいずれか一項に記載の組成物(M)の少なくとも1つの層と、ポリグリコール酸ポリマーとは異なる熱可塑性プラスチックの少なくとも1つの層とを含む多層樹脂ラミネートを形成すること;
(ii)前記多層樹脂ラミネートを延伸して多層延伸製品を製造すること;
を含む、多層延伸製品の製造方法。 - 前記熱可塑性プラスチックが、ポリエチレンテレフタレート、ポリエチレンフラノエート、及びポリエチレンナフタレートなどのポリエステル樹脂、ポリスチレン樹脂、アクリル酸又はメタクリル酸樹脂、ナイロン樹脂、ポリフェニレンスルフィドなどのスルフィド樹脂、並びにポリカーボネート樹脂からなる群から選択される、請求項11に記載の方法。
- 前記多層樹脂ラミネートを形成する工程が共押出成形又は共射出成形によって行われる、請求項11又は12に記載の方法。
- 前記多層樹脂ラミネートが、工程(i)後且つ工程(ii)を受ける前に冷却及び固化される、請求項11~13のいずれか一項に記載の方法。
- 前記多層樹脂ラミネートが、中間の冷却及び再加熱工程なしで工程(ii)を受ける、請求項11~13のいずれか一項に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201862759960P | 2018-11-12 | 2018-11-12 | |
US62/759,960 | 2018-11-12 | ||
EP19163927.7 | 2019-03-20 | ||
EP19163927 | 2019-03-20 | ||
PCT/EP2019/080606 WO2020099246A1 (en) | 2018-11-12 | 2019-11-07 | Polymer composition |
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EP (1) | EP3880753A1 (ja) |
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US4156676A (en) * | 1978-03-27 | 1979-05-29 | Chevron Research Company | Hot melt adhesives having improved thermal stability |
US5914381A (en) * | 1996-09-12 | 1999-06-22 | Mitsui Chemicals, Inc. | Degradable polymer and preparation process of the same |
WO2010010803A1 (ja) * | 2008-07-23 | 2010-01-28 | 株式会社クレハ | 耐剥離ガスバリア性積層体 |
JP2012011776A (ja) * | 2010-06-03 | 2012-01-19 | Ube Industries Ltd | フィルム |
JPWO2012073764A1 (ja) * | 2010-11-29 | 2014-05-19 | 株式会社クレハ | 延伸成形用積層体およびそれを用いた延伸積層体 |
WO2013099692A1 (ja) * | 2011-12-28 | 2013-07-04 | 株式会社クレハ | 延伸成形用積層体およびそれを用いた延伸積層体 |
WO2018115008A1 (en) * | 2016-12-22 | 2018-06-28 | Solvay Sa | Glycolic acid polymer |
EP3339372A1 (en) * | 2016-12-22 | 2018-06-27 | Solvay SA | Glycolic acid polymer composition |
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WO2020099246A1 (en) | 2020-05-22 |
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US20210347936A1 (en) | 2021-11-11 |
CA3115733A1 (en) | 2020-05-22 |
CN113015768A (zh) | 2021-06-22 |
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