JP2020537010A - 1,4:3,6−ジアンヒドロ−l−イジトール単位の高い取込み度を有する熱可塑性ポリエステル - Google Patents
1,4:3,6−ジアンヒドロ−l−イジトール単位の高い取込み度を有する熱可塑性ポリエステル Download PDFInfo
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- JP2020537010A JP2020537010A JP2020520480A JP2020520480A JP2020537010A JP 2020537010 A JP2020537010 A JP 2020537010A JP 2020520480 A JP2020520480 A JP 2020520480A JP 2020520480 A JP2020520480 A JP 2020520480A JP 2020537010 A JP2020537010 A JP 2020537010A
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010041 electrostatic spinning Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010096 film blowing Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002290 germanium Chemical class 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- SRTQDAZYCNOJON-UHFFFAOYSA-N methyl 4-cyano-5-[[5-cyano-2,6-bis(3-methoxypropylamino)-4-methylpyridin-3-yl]diazenyl]-3-methylthiophene-2-carboxylate Chemical compound COCCCNC1=NC(NCCCOC)=C(C#N)C(C)=C1N=NC1=C(C#N)C(C)=C(C(=O)OC)S1 SRTQDAZYCNOJON-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002863 poly(1,4-phenylene oxide) polymer Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 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 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 235000013618 yogurt Nutrition 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
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- 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
-
- 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
-
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- 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
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- 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
- C08L23/14—Copolymers of propene
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- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
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- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
− 少なくとも1種の1,4:3,6−ジアンヒドロ−L−イジトール単位(A)、
− 少なくとも1種の直鎖状脂肪族ジオール単位(B)、
− 少なくとも1種の芳香族ジカルボン酸単位(C)、
前記ポリエステルは、25mL/gより大の、溶液中(25℃;フェノール(50重量%):オルト−ジクロロベンゼン(50重量%);5gのポリエステル/L)の還元粘度を有する。
− 少なくとも1種の1,4:3,6−ジアンヒドロ−L−イジトール単位(A)、
− 少なくとも1種の直鎖状脂肪族ジオール単位(B)、
− 少なくとも1種の芳香族ジカルボン酸単位(C)、
前記熱可塑性ポリエステルは、25mL/gより大の、溶液中(25℃;フェノール(50重量%):オルト−ジクロロベンゼン(50重量%);5gのポリエステル/L)の還元粘度を有する。
− 4〜90mol%の範囲のモル量の1,4:3,6−ジアンヒドロ−L−イジトール単位(A)(その量は、ジオールの合計量を基準にして表されている)、
− 10〜96mol%の範囲のモル量の直鎖状脂肪族ジオール単位(B)(その量は、ジオールの合計量を基準にして表されている)、
− 80〜100mol%の範囲のモル量の芳香族ジカルボン酸単位(C)(その量は、二酸の合計量を基準にして表されている)。
− 反応器の中に、少なくとも1種の1,4:3,6−ジアンヒドロ−L−イジトール(A)、少なくとも1種の直鎖状脂肪族ジオール(B)、及び少なくとも1種の芳香族ジカルボン酸(C)を含むモノマーを導入するステップ;
− その反応器の中に触媒系を導入するステップ;
− 前記モノマーを重合させて熱可塑性ポリエステルを形成させるステップであって、前記ステップは、以下のステップからなっている:
・ オリゴマー化の第一のステップであって、その間に、230〜280℃、有利には240〜270℃の範囲、たとえば250℃の温度で、不活性雰囲気下で、反応媒体を撹拌するステップ;
・ そのオリゴマーを縮合させる第二のステップであって、その間に、形成されたそのオリゴマーを、真空下に250〜300℃、有利には260〜280℃の範囲、たとえば265℃の温度で撹拌して、熱可塑性ポリエステルを形成させる、ステップ;
− その熱可塑性ポリエステルを回収するステップ。
8、ADK STAB 3010、又はIrgafos 168。
ができる。その組成物には、その組成物の合計重量を規準にして、重量で0.1%〜75%、たとえば0.5%〜50%の充填剤及び/又は繊維を含むことができる。本発明による組成物において使用される添加剤としてはさらに、乳白剤、染料及び顔料が挙げられる。それらは、酢酸コバルト及び以下の化合物から選択することができる:HS−325 Sandoplast(登録商標)Red BB(これは、アゾ官能基を担持する化合物であって、ソルベントレッド 195とも呼ばれている)、HS−510 Sandoplast(登録商標)Blue 2B(これは、アントラキノンである)、Polysynthren(登録商標)Blue R、及びClariant(登録商標)RSB Violet。
プロセスは、パドル式若しくはローター式のインターナルミキサー、外部ミキサー、又は単軸スクリュー若しくは二軸スクリューの同方向回転若しくは異方向回転のエクストルーダーの中で実施することができる。しかしながら、押出し法、特に同方向回転のエクストルーダーを使用してこの混合物を製造するのが好ましい。組成物の構成成分の混合は、不活性な雰囲気下で実施してもよい。
させたりすることもまた可能である。
引張試験:ISO 527
ポリエステルの熱的性質は、示差走査熱量測定(DSC)によって測定した:最初にサンプルを、窒素雰囲気下、オープンなるつぼの中で、10℃から280℃へと加熱し(10℃・min−1)、冷却して10℃とし(10℃・min−1)、次いで、第一のステップと同じ条件下でもう一度加熱して320℃とする。ガラス転移温度としては、第二の加熱の中点をとった。各種の融点は、第一の加熱の吸熱ピーク(ピーク開始点)として求める。同様にして、第一の加熱で、融解エンタルピー(曲線より下の面積)を求める。
− エチレングリコール(純度>99.8%)、Sigma−Aldrich製、
− 水中52.5%のイソイディド溶液(純度>99.5%)、Roquette調製、
− テレフタル酸(純度、99+%)、Accros製、
− 二酸化ゲルマニウム(>99.99%)、Sigma Aldrich製
− 酢酸コバルト四水和物(99.999%)、Sigma Aldrich製、
− Irganox 1010、BASF SE製:抗酸化剤、
− Hostanox P−EPQ、Clariant製:抗酸化剤、
− リン酸(99.999+%)、Sigma Aldrich製:抗酸化剤、
− 水酸化テトラエチルアンモニウム(水中40%溶液)、Sigma Aldrich製:エーテル化反応を抑制する重合添加剤。
実施例1
1079g(17.40mol)のエチレングリコール、281gのイソイディド溶液(1.01mol)、2656g(16.00mol)のテレフタル酸、0.5gの水酸化テトラエチルアンモニウム、1.6gのIrganox 1010、0.29gの酢酸コバルト、及び0.96gの二酸化ゲルマニウムを、7.5Lの反応器に加える。
実施例1のポリエステルを、固相状態での後縮合反応ステップにおいて使用する。まず、襞付きの丸底フラスコを備えた油浴を用い、ロータリーエバポレーター中、120℃、窒素気流下で、2時間30分かけてポリマーを結晶化させる。
1004.4g(16.2mol)のエチレングリコール、614.2gのイソイディド溶液(2.2mol%のイソイディドに相当)、2656.1g(16.0mol)のテレフタル酸、0.5gの水酸化テトラエチルアンモニウム、1.6gのIrganox
1010、0.34gの酢酸コバルト、及び1.07gの二酸化ゲルマニウムを、7.5Lの反応器に加える。
実施例2のポリエステルを、固相状態での後縮合反応ステップにおいて使用する。まず、そのポリマーを、襞付きの丸底フラスコを備えた油浴を用い、ロータリーエバポレーター中で、窒素気流下、温度を130から170℃まで徐々に上げながら、7時間かけて、結晶化させる。次いで、その結晶化させたポリマーを、210℃の温度及び2L/分の窒素気流の条件下に置く。
855.9g(13.80mol)のエチレングリコール、1279.5gのイソイディド溶液(4.6mol)、2656.1g(16.0mol)のテレフタル酸、0.5
gの水酸化テトラエチルアンモニウム、1.6gのIrganox 1010、0.49gの酢酸コバルト、及び1.32gの二酸化ゲルマニウムを、7.5Lの反応器に加える。
反証例1
1069.7g(17.25mol)のエチレングリコール、169.7g(1.16mol)のイソソルビド、2656.1g(16.00mol)のテレフタル酸、0.5gの水酸化テトラエチルアンモニウム、1.6gのIrganox 1010、0.29gの酢酸コバルト、及び0.96gの二酸化ゲルマニウムを、7.5Lの反応器に加える。
反証例1のポリエステルを、固相状態での後縮合反応ステップにおいて使用する。まず、襞付きの丸底フラスコを備えた油浴を用い、ロータリーエバポレーター中、120℃、窒素気流下で、2時間30分かけてそのポリマーを結晶化させる。次いで、その結晶化させたポリマーを、230℃の温度(油浴の温度)及び3.7L/分の窒素気流の条件下に置く。
1004.4g(16.2mol)のエチレングリコール、322.4g(2.2mol)のイソソルビド、2656.1g(16.0mol)のテレフタル酸、0.5gの水酸化テトラエチルアンモニウム、1.6gのIrganox 1010、0.34gの酢酸コバルト、及び1.07gの二酸化ゲルマニウムを、7.5Lの反応器に加える。
反証例2のポリエステルを、固相状態での後縮合反応ステップにおいて使用する。まず、そのポリマーを、襞付きの丸底フラスコを備えた油浴を用い、ロータリーエバポレーター中で、窒素気流下、130の温度で、3時間15、結晶化させる。次いで、その結晶化させたポリマーを、210℃の温度及び2L/分の窒素気流の条件下に置く。
856.1g(13.8mol)のエチレングリコール、672.0g(4.6mol)のイソソルビド、2656.1g(16.0mol)のテレフタル酸、0.5gの水酸化テトラエチルアンモニウム、1.6gのIrganox 1010、0.49gの酢酸コバルト、及び1.32gの二酸化ゲルマニウムを、7.5Lの反応器に加える。
同等の調製条件下では、本発明の熱可塑性ポリマーが、イソソルビドベースのポリエステルよりも、硬度及び破断時伸びにおける改良を示すが、さらに、より高い取込み度も示す。
Claims (10)
- 熱可塑性ポリエステルであって、
− 少なくとも1種の1,4:3,6−ジアンヒドロ−L−イジトール単位(A)、
− 少なくとも1種の直鎖状脂肪族ジオール単位(B)、
− 少なくとも1種の芳香族ジカルボン酸単位(C)、
を含み、
前記熱可塑性ポリエステルが、25mL/gより大の、溶液中(25℃;フェノール(50重量%):オルト−ジクロロベンゼン(50重量%);5gのポリエステル/L)の還元粘度を有する、
熱可塑性ポリエステル。 - 前記直鎖状脂肪族ジオール単位(B)が、エチレングリコール、1,3−プロパンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、1,8−オクタンジオール、及び1,10−デカンジオールから選択される、飽和で非環状の直鎖状脂肪族ジオールであることを特徴とする、請求項1に記載の熱可塑性ポリエステル。
- 前記飽和で直鎖状の非環状脂肪族ジオールが、エチレングリコールであることを特徴とする、請求項2に記載の熱可塑性ポリエステル。
- 前記芳香族ジカルボン酸単位(C)がテレフタル酸であることを特徴とする、請求項1〜3のいずれか1項に記載の熱可塑性ポリエステル。
- ガラス転移温度が、75℃〜115℃であることを特徴とする、請求項1〜4のいずれか1項に記載の熱可塑性ポリエステル。
- − 4〜90mol%の範囲のモル量の1,4:3,6−ジアンヒドロ−L−イジトール単位(A)(その量は、ジオールの合計量を基準にして表されている)、
− 10〜96mol%の範囲のモル量の直鎖状脂肪族ジオール単位(B)(その量は、ジオールの合計量を基準にして表されている)、
− 80〜100mol%の範囲のモル量の芳香族ジカルボン酸単位(C)(その量は、二酸の合計量を基準にして表されている)、
を含むことを特徴とする、請求項1〜5のいずれか1項に記載の熱可塑性ポリエステル。 - 請求項1〜6のいずれか1項に記載の熱可塑性ポリエステルを調製するためのプロセスであって、
− 反応器の中に、少なくとも1種の1,4:3,6−ジアンヒドロ−L−イジトール(A)、少なくとも1種の直鎖状脂肪族ジオール(B)、及び少なくとも1種の芳香族ジカルボン酸(C)を含むモノマーを導入するステップ;
− 前記反応器の中に触媒系を導入するステップ;
− 前記モノマーを重合させて前記熱可塑性ポリエステルを形成させるステップであって、前記ステップが、以下のステップからなっている:
・ オリゴマー化の第一のステップであって、その間に、230〜280℃、有利には240〜270℃の範囲、たとえば250℃の温度で、不活性雰囲気下で、前記反応媒体を撹拌するステップ;
・ 前記オリゴマーを縮合させる第二のステップであって、その間に、形成された前記オリゴマーを、真空下に250〜300℃、有利には260〜280℃の範囲、たとえば265℃の温度で撹拌して、前記熱可塑性ポリエステルを形成させる、ステップ;
− 前記熱可塑性ポリエステルを回収するステップ、
を含む、プロセス。 - 請求項1〜6のいずれか1項に記載の前記熱可塑性ポリエステルを含む、組成物。
- 前記ポリマーの衝撃性能を改良することを可能とする追加のポリマーを含み、前記ポリマーが、官能化ポリオレフィンたとえば、官能化エチレン若しくはプロピレンポリマー及びコポリマー、コア−シェルコポリマー、又はブロックコポリマーから選択されることを特徴とする、請求項8に記載の組成物。
- 完成品若しくは半完成品のプラスチック物品を製造するための、請求項1〜6のいずれか1項に記載の熱可塑性ポリエステル、又は請求項8及び9のいずれかに記載の組成物の使用。
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FR1759525 | 2017-10-11 | ||
FR1759525A FR3072094B1 (fr) | 2017-10-11 | 2017-10-11 | Polyester thermoplastique hautement incorpore en motif 1,4 : 3,6-dianhydro-l-iditol |
PCT/FR2018/052505 WO2019073169A1 (fr) | 2017-10-11 | 2018-10-10 | Polyester thermoplastique hautement incorpore en motif 1,4 : 3,6-dianhydro-l-iditol |
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PT3694903T (pt) | 2022-07-04 |
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EP3694903B1 (fr) | 2022-03-30 |
ES2920602T3 (es) | 2022-08-05 |
WO2019073169A1 (fr) | 2019-04-18 |
EP3694903A1 (fr) | 2020-08-19 |
KR20200059241A (ko) | 2020-05-28 |
US11866546B2 (en) | 2024-01-09 |
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