JP7037987B6 - ヒドロキシアルカン酸エステル及びそれを含む樹脂組成物 - Google Patents
ヒドロキシアルカン酸エステル及びそれを含む樹脂組成物 Download PDFInfo
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- JP7037987B6 JP7037987B6 JP2018069245A JP2018069245A JP7037987B6 JP 7037987 B6 JP7037987 B6 JP 7037987B6 JP 2018069245 A JP2018069245 A JP 2018069245A JP 2018069245 A JP2018069245 A JP 2018069245A JP 7037987 B6 JP7037987 B6 JP 7037987B6
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- 239000011342 resin composition Substances 0.000 title claims description 36
- 239000002253 acid Substances 0.000 title claims description 27
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 title description 2
- 238000002425 crystallisation Methods 0.000 claims description 75
- 230000008025 crystallization Effects 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 32
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 29
- 229920006167 biodegradable resin Polymers 0.000 claims description 24
- 229920005992 thermoplastic resin Polymers 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 claims description 16
- 229920000903 polyhydroxyalkanoate Polymers 0.000 claims description 15
- 239000002028 Biomass Substances 0.000 claims description 14
- 229920006038 crystalline resin Polymers 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 230000001737 promoting effect Effects 0.000 claims description 7
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- 239000011347 resin Substances 0.000 description 41
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- 238000006243 chemical reaction Methods 0.000 description 24
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000000465 moulding Methods 0.000 description 12
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000003484 crystal nucleating agent Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 238000005886 esterification reaction Methods 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000004631 polybutylene succinate Substances 0.000 description 4
- 229920002961 polybutylene succinate Polymers 0.000 description 4
- 229920001610 polycaprolactone Polymers 0.000 description 4
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- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000747 poly(lactic acid) Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical group C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical group C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
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- 238000004440 column chromatography Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
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- 125000003438 dodecyl group Chemical group [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])* 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 239000001307 helium Substances 0.000 description 2
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- QPWZVDFFNUROJF-UHFFFAOYSA-N hexadecyl 3-hydroxybutanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CC(C)O QPWZVDFFNUROJF-UHFFFAOYSA-N 0.000 description 2
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- 125000001204 arachidyl 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])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
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Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明の3-ヒドロキシアルカン酸アルキルエステル(化合物(1))は、樹脂の結晶化(又は結晶性)を促進(又は向上)する結晶化促進剤(結晶性向上剤、結晶核剤)として有用な化合物である。
本発明の化合物(1)は、3-ヒドロキシアルカン酸(3-HA)又はその反応性誘導体とアルキルアルコール(例えば、天然由来の高級アルコール)又はその反応性誘導体とを反応させ、エステル化することにより調製できる。
3-ヒドロキシアルカン酸(3-HA)としては、例えば、3-ヒドロキシブタン酸(3-ヒドロキシ酪酸、3-HB)、3-ヒドロキシペンタン酸(3-ヒドロキシ吉草酸)、3-ヒドロキシ-3-メチル-ブタン酸(3-ヒドロキシイソ吉草酸)、3-ヒドロキシヘキサン酸、3-ヒドロキシへプタン酸などの3-ヒドロキシC4-7アルカン酸などが挙げられる。特に、嫌気性条件下における生分解性を有する点から、3-ヒドロキシブタン酸であることが好ましい。
化合物(1)は、慣用の方法で3-ヒドロキシアルカン酸又はその反応性誘導体とアルキルアルコール又はその反応性誘導体とを反応させ、エステル化することにより調製できる。前記エステル化反応は、化学反応であっても、酵素反応であってもよい。
本発明の化合物(1)は、樹脂の結晶化を促進(又は改善)させるための結晶化促進剤(結晶化改善剤、結晶核剤)として使用できる。すなわち、化合物(1)を樹脂に添加又は混合(配合)することにより、樹脂の結晶性を向上させることができる。本発明の化合物(1)は、樹脂の結晶化速度の向上、結晶化温度の低下、結晶化温度におけるエンタルピー増大、微結晶化などに起因して、樹脂の結晶化を促進又は結晶性を改善できる。
樹脂組成物は、少なくとも結晶性樹脂を含む熱可塑性樹脂と、化合物(1)を含む結晶化促進剤とを含んでいればよい。
3-ヒドロキシ酪酸(3-HB):(純度99%、光学純度R体99%ee以上)
ポリヒドロキシ酪酸(PHB):メタボリックス社製「M1200」
[評価方法]
[引張試験]
プレス機により作製した厚さ約400μmのプレスシートをJIS K 6251に準拠したダンベル状6号形試験片に切り抜いた。このダンベル状試験片を、万能材料試験機(ミネベアミツミ(株)製「LTS-1kNB-S50」)を用い、チャック間距離30mm、引張速度5mm/分で引張試験を実施し、破断伸度(%)、初期弾性率(MPa)、最大点強度(MPa)を測定した。なお、破断伸度(%)は、初期のチャック間距離を基準とし、破断時のチャック間距離の増加割合を表す。
示差走査熱量計DSC(ネッチ・ジャパン(株)製「DSC 214 Polyma」)を用いて、190℃で融解した樹脂組成物を冷却速度-100℃/分で-50℃まで急冷し、その後、昇温速度10℃/分の条件で昇温した際の発熱ピーク面積を結晶化温度におけるエンタルピー変化とした。
示差走査熱量計DSC(ネッチ・ジャパン(株)製「DSC 214 Polyma」)を用いて、190℃で融解した樹脂組成物を冷却速度-100℃/分で-50℃まで急冷し、その後、昇温速度10℃/分の条件で昇温した際の発熱ピーク温度を結晶化温度とした。
示差走査熱量計DSC(ネッチ・ジャパン(株)製「DSC 214 Polyma」)を用いて、190℃で融解した樹脂組成物を冷却速度-100℃/分で-30℃まで急冷し、その後、昇温速度10℃/分の条件で昇温した際の吸熱ピーク温度を融点とした。
(アルキルアルコールの反応性誘導体の合成)
セチルアルコール57.7g(0.24mol)をフラスコに入れ、窒素置換し、その後、ジクロロメタン500ml及びピリジン38.5mlを前記フラスコに添加し、攪拌して、セチルアルコールを溶解させた。その後、p-トルエンスルホニルクロライド68.1g(0.36mol)を10分間にわたって分割添加し、室温で24.5時間攪拌した。反応液に2N塩酸250mlを添加し、30分間攪拌した後、水層をジクロロメタン100mlで3度抽出し、抽出物を硫酸マグネシウムで乾燥させた。乾燥後、硫酸マグネシウムをろ別し、減圧乾固により、濃縮固化し、半透粘稠液体110gを得た。この半透明粘稠液体をテトラヒドロフラン500mlに溶解させ、水酸化ナトリウム14.3gを添加し、19時間攪拌分散させた。分散液を減圧乾燥し、テトラヒドロフランを留去した後、ジエチルエーテル750mlを添加して、30分間攪拌し、不溶部分をろ別し、ろ液を減圧乾燥して、ジエチルエーテルを留去して減圧乾固することにより、下記式(2)で表されるセチルアルコールの反応性誘導体(p-トルエンスルホン酸セチルエステル;淡褐色固体78.3g)を単離収率83.1%で得た。
PHB10.8gと3-HBセチルエステル(3)0.57gとを、バッチ式のラボプラストミル((株)東洋精機製作所製、「4M150」)を用いてコンポジット化を行った。混練条件は、トルク:3~4N・m、混練温度:190℃、混練時間:3分間、スクリュー回転数:90rpmであった。コンポジット化により得られた樹脂組成物(3-HBセチルエステル含有率5重量%)を、プレス機にて、190℃で30秒間熱プレスした後、33℃で10分間冷却プレスすることにより、厚さ約400μmのプレスシートを調製した。このプレスシートを用いて、引張試験を行った。また、コンポジット化により得られた樹脂組成物を用いて、DSC測定を行った。
PHBを10.26g、3-HBセチルエステルを1.14gとし、3-HBセチルエステルの含有量を樹脂組成物の10重量%とした以外は、実施例1と同様にプレスシートを調製し、引張試験及びDSC測定を行った。
3-HBセチルエステルを添加することなく、PHBを11.4g用いて実施例1と同様にプレスシートを調製し、引張試験及びDSC測定を行った。
Claims (14)
- 式(1)において、R1がC 1-2 アルキル基である請求項1に記載の化合物。
- 式(1)において、R2がC 14-20 アルキル基である請求項1又は2に記載の化合物。
- 式(1)において、R2がC14-18アルキル基である請求項1~3のいずれかに記載の化合物。
- 式(1)で表される化合物が、R体である請求項1~4のいずれかに記載の化合物。
- 式(1)で表される化合物を製造する方法であって、3-ヒドロキシアルカン酸又はその反応性誘導体とアルキルアルコール又はその反応性誘導体とを反応させて請求項1~5のいずれかに記載の化合物を製造する方法。
- エステル結合を有する生分解性結晶性樹脂の結晶化を促進するための結晶化促進剤であって、請求項1~5のいずれかに記載の化合物を含む結晶化促進剤。
- 少なくとも結晶性樹脂を含む熱可塑性樹脂と、請求項7に記載の結晶化促進剤とを含む樹脂組成物であって、前記結晶性樹脂が、エステル結合を有する生分解性樹脂を含む、樹脂組成物。
- 熱可塑性樹脂が、バイオマス由来の生分解性樹脂を含む請求項8に記載の樹脂組成物。
- 熱可塑性樹脂が、ポリヒドロキシアルカノエートを含む請求項8又は9に記載の樹脂組成物。
- 熱可塑性樹脂が、3-ヒドロキシブタン酸の単独又は共重合体を含む請求項8~10のいずれかに記載の樹脂組成物。
- 熱可塑性樹脂100質量部に対して、請求項7に記載の結晶化促進剤を0.1~20質量部の割合で含む請求項8~11のいずれかに記載の樹脂組成物。
- 請求項8~12のいずれかに記載の樹脂組成物で形成された成形体。
- 少なくとも結晶性樹脂を含む熱可塑性樹脂に、請求項7に記載の結晶化促進剤を添加して、熱可塑性樹脂の結晶化を促進する方法であって、前記結晶性樹脂が、エステル結合を有する生分解性樹脂を含む、方法。
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