JP5777134B2 - ポリアミドの製造方法 - Google Patents
ポリアミドの製造方法 Download PDFInfo
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- JP5777134B2 JP5777134B2 JP2010256955A JP2010256955A JP5777134B2 JP 5777134 B2 JP5777134 B2 JP 5777134B2 JP 2010256955 A JP2010256955 A JP 2010256955A JP 2010256955 A JP2010256955 A JP 2010256955A JP 5777134 B2 JP5777134 B2 JP 5777134B2
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- polyamide
- diamine
- itaconic acid
- glass transition
- synthesized
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- 239000004952 Polyamide Substances 0.000 title claims description 64
- 229920002647 polyamide Polymers 0.000 title claims description 64
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 30
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000004677 Nylon Substances 0.000 claims description 17
- 229920001778 nylon Polymers 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- -1 diamine compound Chemical class 0.000 claims description 14
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 12
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 10
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 description 26
- 150000004985 diamines Chemical class 0.000 description 19
- 229920006351 engineering plastic Polymers 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 150000004984 aromatic diamines Chemical class 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 230000018044 dehydration Effects 0.000 description 10
- 238000006297 dehydration reaction Methods 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 7
- 235000019799 monosodium phosphate Nutrition 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 4
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 229920006122 polyamide resin Polymers 0.000 description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920000704 biodegradable plastic Polymers 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000003950 cyclic amides Chemical group 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 229920013724 bio-based polymer Polymers 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229920006130 high-performance polyamide Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DDLUSQPEQUJVOY-UHFFFAOYSA-N nonane-1,1-diamine Chemical compound CCCCCCCCC(N)N DDLUSQPEQUJVOY-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Polyamides (AREA)
Description
本発明によれば、いわゆるバイオプラスチックが実現され、二酸化炭素の長期固定化等において、その意義は大きい。また、バイオ由来のイタコン酸は、工業規模で安定供給が可能であるので、これを用いることで、バイオプラスチックの安定供給及び製造コストの削減が実現される。
使用した脂肪族系ジアミンは、炭素数n=2のジメチレンジアミン、炭素数n=3のトリメチレンジアミン、炭素数n=4のテトラメチレンジアミン、炭素数n=5のペンタメチレンジアミン、炭素数n=6のヘキサメチレンジアミンの5種類である。
イタコン酸と芳香族ジアミンとにより合成されるポリアミドの構造を図3に示す。図3において、(b)が合成されるポリアミドの構造であり、(c)が使用した芳香族系ジアミンの構造である。ここでは、芳香族系ジアミンとして、4,4’−ジアミノジフェニルエーテル、p−キシリレンジアミン、m−キシリレンジアミンを用いた場合を例にして、その構造を示している。
Claims (3)
- バイオ由来のイタコン酸と、ジアミン化合物のうちのジメチレンジアミン、トリメチレンジアミン、テトラメチレンジアミン、ペンタメチレンジアミン、ヘキサメチレンジアミンのいずれかを極性溶媒中で混合することによりナイロン塩の結晶性粉体を生成し、得られた前記ナイロン塩の結晶性粉体をその融点以上の温度に加熱することで重合して環状ポリアミドを合成することを特徴とするポリアミドの製造方法。
- 前記環状ポリアミドは、一般式1(化1)、一般式2(化2)、または、一般式3(化3)で表される構造を有することを特徴とする請求項1記載のポリアミドの製造方法。
- 前記極性溶媒はエタノールであることを特徴とする請求項1または2記載のポリアミドの製造方法。
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JP2010256955A JP5777134B2 (ja) | 2010-11-17 | 2010-11-17 | ポリアミドの製造方法 |
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JP2010256955A JP5777134B2 (ja) | 2010-11-17 | 2010-11-17 | ポリアミドの製造方法 |
Publications (2)
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JP2012107122A JP2012107122A (ja) | 2012-06-07 |
JP5777134B2 true JP5777134B2 (ja) | 2015-09-09 |
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JP2010256955A Active JP5777134B2 (ja) | 2010-11-17 | 2010-11-17 | ポリアミドの製造方法 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3420017B1 (de) * | 2016-02-22 | 2019-12-18 | Basf Se | Polyamidmischungen mit pyrrolidon enthaltenden polyamiden |
GB2575823B (en) * | 2018-07-24 | 2023-01-18 | Henkel Ag & Co Kgaa | Amine-based reaction products as functional additives |
JP7325777B2 (ja) * | 2020-10-29 | 2023-08-15 | 株式会社GRIPs | ポリアミド系ポリマー |
WO2023127264A1 (ja) * | 2021-12-29 | 2023-07-06 | 国立大学法人北陸先端科学技術大学院大学 | ポリアミド系ポリマー |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1026895A (en) * | 1973-02-21 | 1978-02-21 | Herbert H. Espy | Retention aid resins for paper fillers |
US4420608A (en) * | 1980-12-01 | 1983-12-13 | Standard Oil Company (Indiana) | Polyamides from itaconic acid and diamines |
DE4333238A1 (de) * | 1993-09-30 | 1995-04-06 | Basf Ag | Pyrrolidongruppenhaltige Polyester und Polyamide |
US5442038A (en) * | 1993-10-06 | 1995-08-15 | Srchem, Inc. | Polymers of maleic acid with amines |
JP2008061645A (ja) * | 2006-08-08 | 2008-03-21 | Toray Ind Inc | 連続発酵によるイタコン酸の製造方法 |
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