Polyamides comprising me-bht, compositions comprising such a polyamide, shaped articles comprising such a polyamide or such a composition

Patent metadata

Field	Value
Publication number	US-2016108174-A1
Application number	US-201414894845-A
Country	US
Kind code	A1
Filing date	May 23, 2014
Priority date	May 30, 2013
Publication date	Apr 21, 2016
Grant date	—

Abstract

The invention concerns a polymer, chosen from polyamide, polyimide and polyamideimide, obtained through polymerisation of at least one or several alkyl-BHT diamine chosen from methyl-bis hexamethylene triamine, ethyl-bis hexamethylene triamine, n-propyl-bis hexamethylene triamine and/or i-propyl-bis hexamethylene triamine, and one or several polycarboxylic acid, chosen from aliphatic polycarboxylic acids, aryl polycarboxylic acids, alkylaryl polycarboxylic acids and arylalkyi polycarboxylic acids, said polymer comprising a minimum amount of alkyl-BHT diamine of 1 mol % relative to the total mole amount of diamine monomers comprised in the polymer, a composition comprising such a polyamide, a shaped article comprising such a composition or such a polyamide, a powder comprising particles comprising such a polyamide and a method of obtaining a shaped article comprising such a polyamide.

First claim

1 . A polymer selected from polyamide polymers, polyimide polymers and polyamideimide polymers, obtained through polymerisation of monomers comprising at least:
a. one or more alkyl-BHT diamines selected from methyl-bis hexamethylene triamine, ethyl-bis hexamethylene triamine, n-propyl-bis hexamethylene triamine, and i-propyl-bis hexamethylene triamine, and b. one or more polycarboxylic acids selected from aliphatic polycarboxylic acids, aryl polycarboxylic acids, alkylaryl polycarboxylic acids, and arylalkyl polycarboxylic acids, wherein the polymer comprises a minimum amount of recurring units derived from the one more alkyl-BHT diamines of 1 mol % relative to the total mole amount of recurring units of the polymer derived from diamine monomers, and when the polymer is an aliphatic homopolyamide, then the one or more dicarboxylic acids each comprise at least 8 carbon atoms.

2 . A polymer according to claim 1 , wherein the amount of the one or more alkyl-BHT diamines, is
more or equal to 10 mol %, more or equal to 20 mol %, more or equal to 30 mol %, more or equal to 40 mol %, more or equal to 50 mol %, more or equal to 60 mol %, more or equal to 70 mol %, more or equal to 80 mol %, more or equal to 90 mol %, more or equal to 95 mol %, or is 100 mol % relative to the total amount of diamine monomers and/or less than 100 mol %, in particular less than 99 mol %, and more particularly less than 98 mol %, or even less than 95 mol % relative to the total amount of diamine monomers.

3 . A polymer according to claim 1 wherein the polymer is obtained by polymerization of monomers comprising at least one other diamine in addition to one or more alkyl-BHT diamines, wherein the at least one other diamine is according to the formula H 2 N—R—NH 2 ,wherein R is an aliphatic, an aromatic, an arylaliphatic or an alkylaromatic radical.

4 . A polymer according to claim 1 , wherein the one or more polycarboxylic acids comprise at least one polycarboxylic acid selected from dicarboxylic acids, tricarboxylic acids and tetracarboxylic acids.

5 . Polymer A polymer according to claim 1 , wherein the polymer comprises repeating units derived from lactams or amino-acids.

6 . A polymer according to claim 1 , wherein the polymer is an aliphatic homopolyamide obtained through polymerisation of one alkyl-BHT diamine with a dicarboxylic acid comprising at least 8 carbon atoms.

7 . A polymer according to claim 1 , wherein the polymer is a co-polyamide obtained through polymerisation of at least three different monomers selected from diamines and dicarboxylic acids, wherein the at least three different monomers comprise at least:
one alkyl-BHT diamine, and one dicarboxylic acid.

8 . A polymer according to claim 1 , wherein the polymer is a polyamide comprising recurring units derived from:
(i-1) a dicarboxylic acid component [acid component (AA)], wherein said acid component (AA) comprises at least one long chain aliphatic dicarboxylic acid or derivative thereof [acid (AL long )], said acid (AL long ) having at least 8 carbon atoms, and, optionally, at least one diacid different from said acid (AL long ); and (i-2) a diamine component [amine component (NN)] comprising at least one alkyl-BHT diamine selected from the group consisting of methyl-bis hexamethylene triamine, ethyl-bis hexamethylene triamine, n-propyl-bis hexamethylene triamine and i-propyl-bis hexamethylene triamine, and, optionally, at least one amine different from alkyl-BHT diamine, and optionally recurring units derived from at least one of lactams and amino-acids.

9 . A polymer according to claim 8 , wherein said polyamide comprises recurring units derived from:
(i-1′) an acid component (AA) comprising at least one acid (AL long ) selected from the group consisting of suberic acid [HOOC—(CH 2 ) 6 —COOH], azelaic acid [HOOC—(CH 2 ) 7 —COOH], sebacic acid [HOOC—(CH 2 ) 8 —COOH], undecanedioic acid [HOOC—(CH 2 ) 9 —COOH], dodecandioic acid [HOOC—(CH 2 ) 10 —COOH], tetradecandioic acid [HOOC—(CH 2 ) 11 —COOH], pentadecanedioic acid [HOOC—(CH 2 ) 13 —COOH], hexanedecanedioic acid [HOOC—(CH 2 ) 14 —COOH], andoctanedecanedioic acid [HOOC—(CH 2 ) 16 —COOH], and, optionally, at least one diacid different from said acid (AL long ); and (i-2) an amine component (NN) comprising methyl-bis hexamethylene triamine, and, optionally, at least one amine different from said methyl-bis hexamethylene triamine, and optionally recurring units derived from at least one of lactams and amino-acids.

10 . A polymer according to claim 1 , wherein the polymer:
comprises at least one mono-functional compound, molecule having one functionality able to react with amine or carboxylic acid functions comprises at least one poly-functionnal compounds, molecules having more than three functionality able to react with amine or carboxylic acid functions, presents a stoichiometric disequilibrium r, wherein r=[poly carboxylic acid]/[diamine], wherein r may range from 0.8 to 1.2, and/or has a number average molecular weight, Mn, of at least 10 000 g/mol.

11 . A composition, comprising
at least 20% by weight of a polymer chosen from polyamide, polyimide and polyamideimide, obtained through polymerisation of at least one alkyl-BHT diamine monomer chosen from methyl-bis hexamethylene triamine, ethyl-bis hexamethylene triamine, n-propyl-bis hexamethylene triamine and/or i-propyl-bis hexamethylene triamine, the amount of recurring units derived from alkyl BHT diamine monomer being more than 1 mol % relative to the total mole amount of recurring units of the polymer derived from diamine monomers, and at least one polycarboxylic acid, chosen from aliphatic polycarboxylic acids, aryl polycarboxylic acids, alkylaryl polycarboxylic acids and arylalkyl polycarboxylic acids, optionally phosphorous acid, and at least 0.1% by weight of additional compound(s), wherein the % by weight are based on the total weight of the composition.

12 . A shaped article comprising of a polymer chosen from polyamide, polyimide and polyamideimide, wherein the polymer is obtained through polymerisation of at least:
a. one or more alkyl-BHT diamines selected from methyl-bis hexamethylene triamine, ethyl-bis hexamethylene triamine, n-propyl-bis hexamethylene triamine and/or i-propyl-bis hexamethylene triamine, and b. one or more polycarboxylic acids selected from aliphatic polycarboxylic acids, aryl polycarboxylic acids, alkylaryl polycarboxylic acids and arylalkyl polycarboxylic acids, said polymer comprising a minimum amount of recurring units derived from alkyl-BHT diamine of 1 mol % relative to the total mole amount of recurring units of the polymer derived from diamine monomers.

13 . A powder, comprising particles comprising the polymer of claim 1 , wherein the-powder has a D50 from 10 to 200 μm.

14 . A method for obtaining a shaped article or a powder, comprising:
a) heating a composition comprising at least 20% by weight of one or polymers selected from a polyamides, polyimides or polyamideimides obtained through polymerisation of at least: a. one or more alkyl-BHT diamines selected from methyl-bis hexamethylene triamine, ethyl-bis hexamethylene triamine, n-propyl-bis hexamethylene triamine and/or i-propyl-bis hexamethylene triamine, and b. one or more polycarboxylic acids selected from aliphatic polycarboxylic acids, aryl polycarboxylic acids, alkylaryl polycarboxylic acids and arylalkyl polycarboxylic acids, said polymer comprising an amount of recurring units derived from alkyl-BHT diamines of at least 1 mol % relative to the total mole amount of recurring units of the polymer derived from diamines b) shaping the heated compo

Assignees

• Solvay Specialty Polymers Usa
• Rhodia Operations

Inventors

• Jeol Stéphane
• Flores Joel

Classifications

• C08G73/1082

  wholly aromatic in the tetracarboxylic moiety · CPC title

• C08G69/26 Primary

  derived from polyamines and polycarboxylic acids · CPC title

• C08L79/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/10

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/14

  Polyamide-imides · CPC title