CA3006986C - A solvent-free melt polycondensation process of making furan-based polyamides - Google Patents

A solvent-free melt polycondensation process of making furan-based polyamides Download PDF

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Publication number
CA3006986C
CA3006986C CA3006986A CA3006986A CA3006986C CA 3006986 C CA3006986 C CA 3006986C CA 3006986 A CA3006986 A CA 3006986A CA 3006986 A CA3006986 A CA 3006986A CA 3006986 C CA3006986 C CA 3006986C
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Prior art keywords
diamine
acid
furan
temperature
reaction mixture
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CA3006986A
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English (en)
French (fr)
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CA3006986A1 (en
Inventor
Simona Percec
Stephen Neal Bair
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EIDP Inc
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EI Du Pont de Nemours and Co
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Publication of CA3006986A1 publication Critical patent/CA3006986A1/en
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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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/40—Polyamides containing oxygen in the form of ether groups
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/28—Preparatory processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • B01J27/10—Chlorides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
    • B01J27/18—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr with metals other than Al or Zr
    • B01J27/1802—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates
    • B01J27/1806—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates with alkaline or alkaline earth metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B01J27/232—Carbonates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C49/00—Blow-moulding, i.e. blowing a preform or parison to a desired shape within a mould; Apparatus therefor
    • B29C49/0005—Blow-moulding, i.e. blowing a preform or parison to a desired shape within a mould; Apparatus therefor characterised by the material
    • 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
    • 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
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
    • C08G63/86—Germanium, antimony, or compounds thereof
    • C08G63/866—Antimony or compounds thereof
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/28—Preparatory processes
    • C08G69/30—Solid state polycondensation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2067/00—Use of polyesters or derivatives thereof, as moulding material
    • B29K2067/003—PET, i.e. poylethylene terephthalate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
    • B29K2995/0037—Other properties
    • B29K2995/0065—Permeability to gases
    • B29K2995/0067—Permeability to gases non-permeable
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2031/00—Other particular articles
    • B29L2031/712—Containers; Packaging elements or accessories, Packages
    • B29L2031/7158—Bottles
    • 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
    • C08G2230/00—Compositions for preparing biodegradable polymers

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Mechanical Engineering (AREA)
  • Polyamides (AREA)
CA3006986A 2015-12-15 2016-12-15 A solvent-free melt polycondensation process of making furan-based polyamides Active CA3006986C (en)

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

Publications (2)

Publication Number Publication Date
CA3006986A1 CA3006986A1 (en) 2017-06-22
CA3006986C true CA3006986C (en) 2024-01-02

Family

ID=57714697

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3006986A Active CA3006986C (en) 2015-12-15 2016-12-15 A solvent-free melt polycondensation process of making furan-based polyamides

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
JP2018537573A (ja) 2018-12-20
WO2017106405A1 (en) 2017-06-22
US20210108032A1 (en) 2021-04-15
EP3390495A1 (en) 2018-10-24
US20230212354A1 (en) 2023-07-06
AU2023202677A1 (en) 2023-05-18
KR20180093026A (ko) 2018-08-20
CA3006986A1 (en) 2017-06-22
CN108699240B (zh) 2024-06-25
CN108699240A (zh) 2018-10-23
US20180371167A1 (en) 2018-12-27
JP7296427B2 (ja) 2023-06-22
JP2021152183A (ja) 2021-09-30
AU2016370673A1 (en) 2018-06-14
AU2021203972A1 (en) 2021-07-08
JP6905983B2 (ja) 2021-07-21
US20200283577A1 (en) 2020-09-10
MX2018007279A (es) 2018-09-06

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