Biobased pre-polymers and uses thereof for preparing polymers which are of use as additives in a poly(lactic acid) matrix

Patent metadata

Field	Value
Publication number	US-9896608-B2
Application number	US-201314430187-A
Country	US
Kind code	B2
Filing date	Sep 20, 2013
Priority date	Sep 21, 2012
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

The present invention relates to the use of a compound having the following formula (I):

in which:
A 1 represents a divalent alkylene radical comprising from 2 to 20 carbon atoms; A 2 represents a divalent alkylene radical comprising from 2 to 20 carbon atoms; A 3 is selected from the group consisting of the following divalent radicals:
an alkylene comprising from 2 to 600; and an arylene comprising from 6 to 30 carbon atoms;
X 1 , X 3 and X 4 represent —O— or —NH—; X′ 2 is selected from the group consisting of: —S—, —CH 2 — and a bond; and n and m represent an integer ranging from 1 to 1000;

for the preparation of additives in a matrix of polyester, polyvinyl chloride, polyurethane, polyamide, poly(alkyl acrylate), poly(alkyl methacrylate), polystyrene or polyolefin.

First claim

What is claimed is:

1. A method for preparing additives selected from the group consisting of compounds having the following formulas (II), (III), (IV), (V) and (VI):

wherein:
A 1 represents a divalent alkylene radical, which is linear or branched, comprising from 2 to 20 carbon atoms, the said radical possibly comprising one or more unsaturations, and being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms;
A 2 represents a divalent alkylene radical, which is linear or branched, comprising from 2 to 20 carbon atoms, the said radical possibly comprising one or more unsaturations, and being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms;
A 3 is selected from the group consisting of the following divalent radicals:
a linear or branched alkylene, comprising from 2 to 600 carbon atoms, the said radical possibly comprising one or more unsaturations, being possibly interrupted by at least one heteroatom selected from O, N and S, and being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms; and
an arylene comprising from 6 to 30 carbon atoms, the said radical being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms;

X 1 , X 3 and X 4 , which may be identical or different, represent, independently of one another, —O— or —NH—;
X′ 2 is selected from the group consisting of: —S—, —CH 2 — and a bond; and
n and m represent, independently of one another, an integer ranging from 1 to 1000;

on the condition that the total number of carbon atoms of the radicals A 1 , A 2 and X′ 2 is greater than or equal to 8;
R 1 and R 2 represent, independently of one another, H or an alkyl group, which is linear or branched, comprising from 1 to 20 carbon atoms, wherein the said alkyl group may possibly comprise at least one double bond or one triple bond;
A 4 represents a divalent alkylene radical, which is linear or branched, comprising from 1 to 20 carbon atoms, the said radical possibly comprising at least one unsaturation;
A 5 is selected from the group consisting of the radicals:
alkylene, which is linear or branched, comprising from 1 to 20 carbon atoms, the said radical possibly comprising at least one unsaturation;
arylene, comprising from 6 to 20 carbon atoms, the said arylene radical being possibly substituted;
cycloalkylene, comprising from 3 to 20 carbon atoms, the said cycloalkylene radical being possibly substituted;
cycloalkylene-alkylene-cycloalkylene comprising from 6 to 30 carbon atoms; and
alkylene-cycloalkylene comprising from 4 to 15 carbon atoms;

v represents an integer ranging from 1 to 5000;
A and B represent the following radicals:

D and E represent the following radicals:

p and q represent, independently of one another, an integer ranging from 1 to 5000;
t and s represent, independently of one another, an integer ranging from 1 to 5000;

from a compound having the following formula (I):

wherein the additives are obtained by a polymerization step using the compound of formula I.

2. The method according to claim 1 , wherein the additives enhance the reinforcement against shocks of a matrix of polyester, poly(vinyl chloride), polyurethane, polyamide, poly(alkyl acrylate), poly(alkyl methacrylate), polystyrene or polyolefin, and/or to assist in the nanostructuring of the said matrix.

3. Compounds having the following formula (IA):

wherein:
A 1 represents a divalent alkylene radical, which is linear or branched, wherein the number of carbon atoms is greater than or equal to 10, the said radical possibly comprising one or more unsaturations, and being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms;
A 2 represents a divalent alkylene radical, which is linear or branched, wherein the number of carbon atoms is greater than or equal to 10, the said radical possibly comprising one or more unsaturations, and being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms;
A 3 is selected from the group consisting of the following divalent radicals:
a linear or branched alkylene, comprising from 2 to 600 carbon atoms, the said radical possibly comprising one or more unsaturations, being possibly interrupted by at least one heteroatom selected from O, N and S, and being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms; and
an arylene comprising from 6 to 30 carbon atoms, the said radical being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms;

X 1 , X 3 and X 4 , which may be identical or different, represent, independently of one another, —O— or —NH—;

n and m represent, independently of one another, an integer ranging from 1 to 1000;
X 2 represents —CH 2 — or a bond; and

on the condition that the total number of carbon atoms of the radicals A 1 , A 2 and X 2 is greater than or equal to 10;
with the exception of the following compounds:

4. A compound having the following formula (II):

wherein:
A 1 represents a divalent alkylene radical, which is linear or branched, comprising from 2 to 20 carbon atoms, the said radical possibly comprising one or more unsaturations, and being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms;
A 2 represents a divalent alkylene radical, which is linear or branched, comprising from 2 to 20 carbon atoms, the said radical possibly comprising one or more unsaturations, and being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms;
A 3 is selected from the group consisting of the following divalent radicals:
a linear or branched alkylene, comprising from 2 to 600 carbon atoms, the said radical possibly comprising one or more unsaturations, being possibly interrupted by at least one heteroatom selected from O, N and S, and being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms; and
an arylene comprising from 6 to 30 carbon atoms, the said radical being possibly substituted by at least one substituent —OAlk, Alk representing an alkyl group comprising from 1 to 10 carbon atoms;

X 1 , X 3 and X 4 , which may be identical or different, represent, independently of one another, —O— or —NH—;
X′ 2 is selected from the group consisting of: —S—, —CH 2 — and a bond;

on the condition that the total number of carbon atoms of the radicals A 1 , A 2 and X′ 2 is greater than o

Assignees

• Institut Des Corps Gras Etudes Et Rech Techniques—Iterg
• Centre Nat Rech Scient
• Univ De Bordeaux I
• Centre National De La Recherch Scient C N R S
• Univ Bordeaux

Inventors

• Cramail Henri
• Lebarbe Thomas
• Gadenne Benoit Jean Marie
• Alfos Carine

Classifications

• C08L67/04

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence) · CPC title

• C08L75/02

  Polyureas · CPC title

• D01F1/10

  Other agents for modifying properties · CPC title

• C09J167/04 Primary

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C09J167/06 takes precedence) · CPC title

• C08L67/00

  Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers · CPC title