EP1994077A2 - Nouvelles utilisations d'un copolymere comprenant des blocs polyamide et des blocs polyethers provenant au moins en partie du polytrimethylene ether glycol - Google Patents

Nouvelles utilisations d'un copolymere comprenant des blocs polyamide et des blocs polyethers provenant au moins en partie du polytrimethylene ether glycol

Info

Publication number
EP1994077A2
EP1994077A2 EP07731641A EP07731641A EP1994077A2 EP 1994077 A2 EP1994077 A2 EP 1994077A2 EP 07731641 A EP07731641 A EP 07731641A EP 07731641 A EP07731641 A EP 07731641A EP 1994077 A2 EP1994077 A2 EP 1994077A2
Authority
EP
European Patent Office
Prior art keywords
blocks
polyamide
copolymer
ether glycol
use according
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.)
Withdrawn
Application number
EP07731641A
Other languages
German (de)
English (en)
French (fr)
Inventor
Frédéric MALET
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema France SA
Original Assignee
Arkema France SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Arkema France SA filed Critical Arkema France SA
Publication of EP1994077A2 publication Critical patent/EP1994077A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
    • B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
    • B01D71/80—Block polymers
    • 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
    • C08G69/44—Polyester-amides
    • 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
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • 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
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • 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
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
    • 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
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
    • C08G81/025—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyether sequences
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2325/00—Details relating to properties of membranes
    • B01D2325/36—Hydrophilic membranes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/52—Polyethers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/56—Polyamides, e.g. polyester-amides

Definitions

  • the present invention relates to a new use of a copolymer comprising polyamide blocks and polyether blocks, the latter being at least partly polytrimethylene ether glycol (abbreviated PO3G).
  • a copolymer comprising polyamide blocks and polyether blocks, the latter being at least partly polytrimethylene ether glycol (abbreviated PO3G).
  • polyether block blocks In polyether block blocks (PEBA), polyamide blocks are known to be rigid segments while polyether blocks are flexible segments.
  • PA Polyamide block copolymers
  • PE polyether blocks
  • PEBA PA and PE block copolymers
  • the polyamide sequences with dicarboxylic chain ends come for example from the condensation of polyamide precursors in the presence of a chain-control dicarboxylic acid.
  • the polyamide blocks with diamine chain ends come for example from the condensation of polyamide precursors in the presence of a chain-regulating diamine.
  • the polyamide block and polyether block polymers may also comprise randomly distributed units. Said polymers can be prepared by the simultaneous reaction of the polyether and the precursors of the polyamide blocks.
  • polyetherdiol, polyamide precursors, and a chain-regulating diacid can be reacted or polyetherdiamine, polyamide precursors, and a chain-regulating diacid can be reacted.
  • a polymer having essentially polyether blocks is obtained, polyamide blocks of very variable length depending on the moment in which the chain regulator intervenes during the formation of the PA block, but also the various reagents reacted randomly which are distributed in a Random (statistical) along the polymer chain.
  • the polyamide block may consist of a "homopolyamide” structure [polymerization of a single monomer, ie a single lactam, a single amino acid CC or a single pair (diacid, diamine)] or else of a "copolyamide” type structure. with the polymerization of a mixture of at least two monomers selected from the three types mentioned in the previous case.
  • the polyamide blocks are obtained in the presence of a diacid or a chain-control diamine depending on whether polyamide blocks with acid or amine ends are desired. If the precursors already comprise a diacid or a diamine, it suffices, for example, to use it in excess, but it is also possible to use another diacid or another diamine taken from the dicarboxylic acid and diamine groups defined below.
  • French patent application FR 88 15441 discloses a waterproof breathable film based on polyetheresteramide, in particular PA 12 - polytetramethylene glycol (PTMG).
  • PTMG polytetramethylene glycol
  • Another problem is the too low water uptake and the reduction of the water vapor permeability.
  • WO97 / 26020 discloses scented resins consisting of a polyetheresteramide type polymer resin for the regular diffusion of volatile substances. This document does not disclose selective diffusion of gases.
  • thermoplastic polymer compositions comprising a polyamide and at least one PEBA which is a hydrophilic modifier and / or antistaticity modifier.
  • EP0476963 relates to a polymer mixture comprising PEBA with polyether blocks predominant in PEG, and a polyether block PEBA containing no PEG but based on PTMG or PPG.
  • the PO3G-based PEBA polymer according to the invention not only has properties for improving the insulating matrix resistivity but also properties:
  • PA represents a polyamide block
  • PE represents a polyether block
  • n represents the number of units -PA-PE- of said copolymer, and in which said blocks come either entirely from polytrimethylene ether glycol (PO 3 G) or else come from a mixture or a copolymer of PO3G and at least one of polyethylene ether glycol (PEG), polypropylene ether glycol (PPG), polytetramethylene ether glycol (PTMG), polyhexamethylene ether glycol and copolymers of tetrahydrofuran (THF) and 3- alkyl tetrahydrofuran (3MeTHF); as breathable product or as an additive imparting breathability properties to thermoplastic polymers to form a selective diffusion membrane depending on the nature of the gas; as an additive to polyamide 6, polyamide 6.6 or copolyamide based on 6 / 6.6 to be converted into a film to improve the mechanical properties and / or processability of said polyamide.
  • PEG polyethylene ether glyco
  • said PE blocks have a molecular weight ⁇ 800.
  • said PE blocks have a molecular weight of at least 250.
  • said PE blocks have a molecular mass of between 250 and 650.
  • the copolymer is characterized in that at least 10%, preferably at least 20%, even more preferably at least 30%, advantageously at least 50%, still more advantageously at least 75% and, more preferably, 85 to 100% by weight of the PE blocks are from polytrimethylene ether glycol (% by weight based on the total weight of said PE blocks).
  • the percentage by weight of PA blocks relative to the total weight of said copolymer is in particular at least 10%, more preferably at least 15%, and preferably up to 90%, more preferably between 40 and 60%.
  • the PA blocks have in particular a number-average molecular mass of at least 300, preferably at least 600, and preferably ranging up to 10,000, more preferably up to 5000, and even more preferably up to at 3000.
  • n is 1, being in particular at least 5, more preferably at least 6, and up to an average of 60, preferably up to an average of 30, so more preferred up to an average of 25.
  • the PA blocks are in particular carboxylic ends so that the bonds between the PA and PE blocks are ester bonds.
  • the PA blocks having carboxylic end groups may be the condensation product of a lactam, in particular a lactam C 4 -C 4, an amino acid, in particular an amino acid, C 4 -C 4 or a combination of both with a dicarboxylic acid, in particular a C 4 -C 20 dicarboxylic acid;
  • lactams examples include caprolactam, oenantholactam and lauryllactam.
  • amino acids examples include aminocaproic acid, amino-7-heptanoic acid, amino-11-undecanoic acid and amino-12-dodecanoic acid.
  • dicarboxylic acids examples include 1,4-cyclohexyldicarboxylic acid, butanedioic, adipic, azelaic, suberic, sebacic, dodecanedicarboxylic and terephthalic and isophthalic acids, but also dimerized fatty acids.
  • the carboxyl-terminated PA blocks may also be the condensation product of a dicarboxylic acid such as a C 4 -C 20 alkyl dicarboxylic acid and a diamine, especially a C 2 -C 20 diamine.
  • a dicarboxylic acid such as a C 4 -C 20 alkyl dicarboxylic acid and a diamine, especially a C 2 -C 20 diamine.
  • diamines mention may be made of hexamethylenediamine, dodecamethylenediamine, trimethylhexamethylenediamine, isomers of bis (4-aminocyclohexyl) methane (BACM), bis (3-methyl-4-aminocyclohexyl) methane (BMACM), and 2-2-bis- (3-methyl-4-aminocyclohexyl) -propane (BMACP), and para-amino-di-cyclohexyl-methane (PACM), and isophoronediamine (IPDA), 2,6-bis (aminomethyl) norbornane (BAMN) and piperazine.
  • BCM bis (4-aminocyclohexyl) methane
  • BMACM bis (3-methyl-4-aminocyclohexyl) methane
  • BMACP 2-2-bis- (3-methyl-4-aminocyclohexyl) -propane
  • PAMN para-
  • the PA blocks can be chosen from the blocks PA 6, PA 11, PA 12, PA 6.6, PA 6.9, PA 6.10, PA 6.12, PA 6.14, PA 6.18, PA Pip.10 and PA 9.6.
  • the PE blocks come either entirely from polytrimethylene ether glycol (PO3G) or they also advantageously come from PO3G and from at least one of polyethylene ether glycol (PEG), polypropylene ether glycol (PPG), polytetramethylene ether glycol (PTMG), polyhexamethylene ether glycol and copolymers of tetrahydrofuran (THF) and 3-alkyl tetrahydrofuran (3MeTHF). It is also possible to envisage a PE block of "copolyether” type containing a series of PE blocks of the types mentioned above. The chain ends of the copolyethers can be diOH, diNH 2, diisocyanate or diacid according to their synthesis process.
  • the polyether glycols in addition to PO3G in the PE block have an average molecular weight such that the PE block the containers have an average molecular weight of at least about 800, more preferably at least about 1000, and preferably at least about 1500. Also, preferably at least about 50% by weight, more preferably at least about less than 75% by weight, and more preferably about 85 to 100% by weight, of the polyether glycol used to form the PE block is PO3G.
  • the present invention relates more specifically to the use of a copolymer of formula (I) as defined above as an antistatic product or as an additive imparting antistatic properties to thermoplastic polymers such as polyamides or elastomers.
  • the present invention also relates more particularly to the use of a copolymer of formula (I) as defined above as a breathable product or as an additive imparting properties of breathability to thermoplastic polymers such as polyamides. or elastomers.
  • the present invention also relates more particularly to the use of a copolymer of formula (I) as defined above to form a selective diffusion membrane depending on the nature of the gas.
  • the copolymer of formula (I) can be used as an additive to polyamide 6, polyamide 6.6 or a copolyamide based on 6 / 6.6 to be converted into a film to improve the mechanical properties and / or the the transformation of polyamide.
  • the copolymers of the invention may be prepared by any means for hanging the polyamide blocks and the polyether blocks.
  • essentially two methods are used, one said in two steps, the other in one step.
  • the polyamide blocks are first manufactured and then, in a second step, polyamide blocks and polyether blocks.
  • the polyamide precursors, the chain regulator (or the dicarboxylic acid or stoichiometric excess diamine) and the polyether are mixed; a polymer having essentially polyether blocks, polyamide blocks of very variable length, but also the various reagents reacted in a random manner which are distributed randomly (statistically) along the polymer chain.
  • Catalysts described in US Pat. Nos. 4,331,786, 4,155,475, 4,195,155, 4,839,441, 4,884,014, 4,230,838 and 4,332,920 can be used.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polyamides (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
EP07731641A 2006-02-16 2007-02-16 Nouvelles utilisations d'un copolymere comprenant des blocs polyamide et des blocs polyethers provenant au moins en partie du polytrimethylene ether glycol Withdrawn EP1994077A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0601354A FR2897354A1 (fr) 2006-02-16 2006-02-16 Nouvelle utilisation d'un copolymere comprenant des blocs polyamide et des blocs polyethers provenant au moins en partie du polytrimethylene ether glycol
US78435506P 2006-03-21 2006-03-21
PCT/FR2007/050817 WO2007093752A2 (fr) 2006-02-16 2007-02-16 Nouvelles utilisations d'un copolymere comprenant des blocs polyamide et des blocs polyethers provenant au moins en partie du polytrimethylene ether glycol

Publications (1)

Publication Number Publication Date
EP1994077A2 true EP1994077A2 (fr) 2008-11-26

Family

ID=36956178

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07731641A Withdrawn EP1994077A2 (fr) 2006-02-16 2007-02-16 Nouvelles utilisations d'un copolymere comprenant des blocs polyamide et des blocs polyethers provenant au moins en partie du polytrimethylene ether glycol

Country Status (9)

Country Link
US (1) US20090221767A1 (ko)
EP (1) EP1994077A2 (ko)
JP (1) JP2009526892A (ko)
KR (1) KR20080093056A (ko)
CN (1) CN101426567A (ko)
CA (1) CA2642439A1 (ko)
FR (1) FR2897354A1 (ko)
TW (1) TW200745221A (ko)
WO (1) WO2007093752A2 (ko)

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WO2010129328A2 (en) 2009-04-28 2010-11-11 Surmodics, Inc. Devices and methods for delivery of bioactive agents
US8883284B2 (en) * 2010-09-03 2014-11-11 Transhield Technology As Vapor permeable fabric constructs with static or dynamic antimicrobial compositions
FR2965269B1 (fr) * 2010-09-28 2013-10-04 Arkema France Composition a base de peba et son utilisation pour la fabrication d'objets transparents resistants a un impact de haute vitesse
FR2969525A1 (fr) * 2010-12-27 2012-06-29 Arkema France Composite bois/polymere a stabilite thermique amelioree
US9861727B2 (en) 2011-05-20 2018-01-09 Surmodics, Inc. Delivery of hydrophobic active agent particles
US10213529B2 (en) 2011-05-20 2019-02-26 Surmodics, Inc. Delivery of coated hydrophobic active agent particles
WO2013002602A2 (ko) * 2011-06-30 2013-01-03 코오롱인더스트리 주식회사 타이어 이너라이너용 필름 및 이의 제조 방법
US9399374B2 (en) 2011-06-30 2016-07-26 Kolon Industries, Inc. Film for a tire inner liner and preparation method therefor
US11246963B2 (en) 2012-11-05 2022-02-15 Surmodics, Inc. Compositions and methods for delivery of hydrophobic active agents
KR102062814B1 (ko) * 2012-12-31 2020-01-06 코오롱인더스트리 주식회사 가교 고분자, 고분자 수지 조성물 및 고분자 필름
US20150121888A1 (en) * 2013-11-05 2015-05-07 General Electric Company Gas turbine online wash control
WO2016047710A1 (ja) * 2014-09-24 2016-03-31 株式会社ブリヂストン タイヤ
FR3037961B1 (fr) * 2015-06-26 2019-12-20 Arkema France Peba pour adherence directe sur tpe
US10898446B2 (en) 2016-12-20 2021-01-26 Surmodics, Inc. Delivery of hydrophobic active agents from hydrophilic polyether block amide copolymer surfaces
US10525406B2 (en) * 2017-05-30 2020-01-07 Saudi Arabian Oil Company Polymer blended membranes for sour gas separation
US20220169596A1 (en) * 2019-03-26 2022-06-02 Jean-Christophe Raboin Derivatives of 10-methylene lipids, process for preparing such derivatives and use thereof
FR3096683B1 (fr) * 2019-05-27 2022-03-04 Arkema France copolyesteramide auto-ignifugé
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Also Published As

Publication number Publication date
WO2007093752A3 (fr) 2008-09-12
CA2642439A1 (fr) 2007-08-23
TW200745221A (en) 2007-12-16
KR20080093056A (ko) 2008-10-17
US20090221767A1 (en) 2009-09-03
WO2007093752A2 (fr) 2007-08-23
JP2009526892A (ja) 2009-07-23
CN101426567A (zh) 2009-05-06
FR2897354A1 (fr) 2007-08-17

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