JP2018537573A5 - - Google Patents
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- Publication number
- JP2018537573A5 JP2018537573A5 JP2018531063A JP2018531063A JP2018537573A5 JP 2018537573 A5 JP2018537573 A5 JP 2018537573A5 JP 2018531063 A JP2018531063 A JP 2018531063A JP 2018531063 A JP2018531063 A JP 2018531063A JP 2018537573 A5 JP2018537573 A5 JP 2018537573A5
- Authority
- JP
- Japan
- Prior art keywords
- diamine
- reaction mixture
- diamines
- furan
- temperature
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 150000004985 diamines Chemical class 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- -1 ester derivative of 2,5-furan dicarboxylic acid Chemical class 0.000 claims description 8
- 239000004952 Polyamide Substances 0.000 claims description 6
- 229920002647 polyamide Polymers 0.000 claims description 6
- 150000005690 diesters Chemical class 0.000 claims description 5
- 150000004984 aromatic diamines Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-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 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- GMHHUVNHSIFZRG-UHFFFAOYSA-N 2-[4-(2-aminoethyl)-2,5-dimethylphenyl]ethanamine Chemical group CC1=CC(CCN)=C(C)C=C1CCN GMHHUVNHSIFZRG-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- RZPBZEISZUFQSV-UHFFFAOYSA-N 4-(4-aminonaphthalen-1-yl)naphthalen-1-amine Chemical compound C12=CC=CC=C2C(N)=CC=C1C1=CC=C(N)C2=CC=CC=C12 RZPBZEISZUFQSV-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- HDIHOAXFFROQHR-UHFFFAOYSA-N 6-aminohexylcarbamic acid Chemical compound NCCCCCCNC(O)=O HDIHOAXFFROQHR-UHFFFAOYSA-N 0.000 description 1
- IVIUYEGFAXKIDZ-UHFFFAOYSA-M ClCCCCO[Zn]O Chemical compound ClCCCCO[Zn]O IVIUYEGFAXKIDZ-UHFFFAOYSA-M 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- XMSVKICKONKVNM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-diamine Chemical compound C1CC2(N)C(N)CC1C2 XMSVKICKONKVNM-UHFFFAOYSA-N 0.000 description 1
- FQYHHEJETOLDHR-UHFFFAOYSA-K butyl(chloro)tin(2+);dihydroxide Chemical compound CCCC[Sn](O)(O)Cl FQYHHEJETOLDHR-UHFFFAOYSA-K 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 229910001380 potassium hypophosphite Inorganic materials 0.000 description 1
- CRGPNLUFHHUKCM-UHFFFAOYSA-M potassium phosphinate Chemical compound [K+].[O-]P=O CRGPNLUFHHUKCM-UHFFFAOYSA-M 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KOUDKOMXLMXFKX-UHFFFAOYSA-N sodium oxido(oxo)phosphanium hydrate Chemical compound O.[Na+].[O-][PH+]=O KOUDKOMXLMXFKX-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021105351A JP7296427B2 (ja) | 2015-12-15 | 2021-06-25 | フラン系ポリアミドを生成する無溶媒溶融重縮合プロセス |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562267344P | 2015-12-15 | 2015-12-15 | |
| US62/267,344 | 2015-12-15 | ||
| PCT/US2016/066761 WO2017106405A1 (en) | 2015-12-15 | 2016-12-15 | A solvent-free melt polycondensation process of making furan-based polyamides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021105351A Division JP7296427B2 (ja) | 2015-12-15 | 2021-06-25 | フラン系ポリアミドを生成する無溶媒溶融重縮合プロセス |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018537573A JP2018537573A (ja) | 2018-12-20 |
| JP2018537573A5 true JP2018537573A5 (enExample) | 2020-01-30 |
| JP6905983B2 JP6905983B2 (ja) | 2021-07-21 |
Family
ID=57714697
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018531063A Active JP6905983B2 (ja) | 2015-12-15 | 2016-12-15 | フラン系ポリアミドを生成する無溶媒溶融重縮合プロセス |
| JP2021105351A Active JP7296427B2 (ja) | 2015-12-15 | 2021-06-25 | フラン系ポリアミドを生成する無溶媒溶融重縮合プロセス |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021105351A Active JP7296427B2 (ja) | 2015-12-15 | 2021-06-25 | フラン系ポリアミドを生成する無溶媒溶融重縮合プロセス |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US20180371167A1 (enExample) |
| EP (1) | EP3390495A1 (enExample) |
| JP (2) | JP6905983B2 (enExample) |
| KR (1) | KR20180093026A (enExample) |
| CN (1) | CN108699240B (enExample) |
| AU (3) | AU2016370673A1 (enExample) |
| CA (1) | CA3006986C (enExample) |
| MX (1) | MX2018007279A (enExample) |
| WO (1) | WO2017106405A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256668B (zh) * | 2019-06-04 | 2021-12-10 | 中国科学技术大学 | 高分子量呋喃基芳香聚酰胺及其制备方法和应用 |
| CN111234207A (zh) * | 2020-03-04 | 2020-06-05 | 东华大学 | 一种透明生物基聚酰胺及其制备方法 |
| CN111961199B (zh) * | 2020-09-02 | 2022-01-28 | 中国科学院宁波材料技术与工程研究所 | 生物基耐高温聚酰胺复合材料、其制备方法及应用 |
| CN111995746B (zh) * | 2020-09-02 | 2022-01-28 | 中国科学院宁波材料技术与工程研究所 | 生物基耐高温聚酰胺复合材料、其低温预缩聚制法及应用 |
| CN112111058B (zh) * | 2020-10-16 | 2022-07-05 | 天津工业大学 | 一种呋喃二甲酸二胺高聚物的制备方法 |
| CN113429569B (zh) * | 2021-07-23 | 2022-08-16 | 四川大学 | 一种高分子量呋喃聚酰胺的制备方法 |
| CN113896886B (zh) * | 2021-09-24 | 2023-07-25 | 珠海万通特种工程塑料有限公司 | 一种呋喃二酸基聚酰胺及其制备方法和一种呋喃二酸基聚酰胺组合物 |
| CN116082634B (zh) * | 2022-12-30 | 2025-05-23 | 安徽利科新材料科技有限公司 | 磺酸基改性呋喃基聚酰胺及其制备方法及装置 |
| CN116815344B (zh) * | 2023-08-29 | 2023-11-21 | 泰和新材集团股份有限公司 | 一种生物基聚酰胺纤维及其制备方法 |
| EP4582466A1 (en) | 2024-01-05 | 2025-07-09 | Arkema France | Process for the manufacture of semi-aromatic polyamides |
| CN118745245B (zh) * | 2024-07-19 | 2025-10-31 | 南京工业大学 | 一种呋喃基聚酰胺及其制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101456949B (zh) * | 2007-12-14 | 2012-01-18 | 金发科技股份有限公司 | 一种半芳香族聚酰胺及其制备方法 |
| JP5812791B2 (ja) * | 2011-03-28 | 2015-11-17 | キヤノン株式会社 | プリンター、複写機 |
| JP6185981B2 (ja) * | 2012-03-30 | 2017-08-23 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | フラン系ポリアミド |
| KR101465466B1 (ko) * | 2013-02-12 | 2014-11-27 | 한국과학기술연구원 | 고상중합 방법을 이용한 바이오매스 유래 퓨란계 코폴리아미드의 제조방법 |
| WO2015060718A1 (en) * | 2013-10-21 | 2015-04-30 | Furanix Technologies B.V. | Process for preparing a furan-based polyamide, a furan-based oligomer and compositions and articles comprising the furan-based polyamide |
| JP6168985B2 (ja) * | 2013-12-24 | 2017-07-26 | 花王株式会社 | 接着剤 |
| DK3137547T3 (da) * | 2014-05-01 | 2023-09-18 | Covation Inc | Transesterificerede furanbaserede polyestere og genstand fremstillet deraf |
| PL3307515T3 (pl) * | 2015-06-11 | 2021-06-28 | Dupont Industrial Biosciences Usa, Llc | Zwiększona wydajność bariery dzięki mieszankom poli(furandikarboksylanu etylenu) i poli(tereftalanu etylenu) |
| US20230303825A1 (en) * | 2018-10-22 | 2023-09-28 | Covation Inc. | Process for producing polyester article |
-
2016
- 2016-12-15 MX MX2018007279A patent/MX2018007279A/es unknown
- 2016-12-15 KR KR1020187019507A patent/KR20180093026A/ko not_active Ceased
- 2016-12-15 CN CN201680081896.8A patent/CN108699240B/zh active Active
- 2016-12-15 US US16/062,204 patent/US20180371167A1/en not_active Abandoned
- 2016-12-15 WO PCT/US2016/066761 patent/WO2017106405A1/en not_active Ceased
- 2016-12-15 JP JP2018531063A patent/JP6905983B2/ja active Active
- 2016-12-15 CA CA3006986A patent/CA3006986C/en active Active
- 2016-12-15 EP EP16822341.0A patent/EP3390495A1/en not_active Withdrawn
- 2016-12-15 AU AU2016370673A patent/AU2016370673A1/en not_active Abandoned
-
2020
- 2020-05-22 US US16/881,441 patent/US20200283577A1/en not_active Abandoned
- 2020-12-17 US US17/125,366 patent/US20210108032A1/en not_active Abandoned
-
2021
- 2021-06-15 AU AU2021203972A patent/AU2021203972A1/en not_active Abandoned
- 2021-06-25 JP JP2021105351A patent/JP7296427B2/ja active Active
-
2023
- 2023-03-15 US US18/121,831 patent/US20230212354A1/en not_active Abandoned
- 2023-05-02 AU AU2023202677A patent/AU2023202677A1/en not_active Abandoned
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