Novel plasticizers, process for the preparation thereof, and use thereof

Patent metadata

Field	Value
Publication number	US-2025263523-A1
Application number	US-202318852573-A
Country	US
Kind code	A1
Filing date	Mar 31, 2023
Priority date	Mar 31, 2022
Publication date	Aug 21, 2025
Grant date	—

Abstract

The use of a composition including at least one compound derived from cashew nut shell oil (CNSL), which has at least one ester function and/or at least one epoxide function, as a plasticizing agent for cellulose acetate, for the preparation of a plastic material including or solely composed of cellulose acetate.

First claim

1 .- 25 . (canceled)

26 . A process for preparing a plastic material comprising or consisting of cellulose acetate, comprising a step of mixing cellulose acetate with a composition comprising
1) at least one primary plasticizer of cellulose acetate, in an extruder, said composition comprising as primary plasticizer at least one compound derived from CNSL which has at least one ester function and/or at least one epoxide function or at least one compound of formula (1), or 2) at least one primary plasticizer of cellulose acetate, in a solvent, to form a solution, said composition comprising as primary plasticizer at least one compound derived from CNSL which has at least one ester function and/or at least one epoxide function or at least one compound of formula (1),

formula (1) in which
R is selected from:
a hydrogen atom or
a CO—R1 group,

R 0 is selected from:
a linear alkyl group of 15 carbon atoms, optionally comprising from 1 to 3 epoxide functions or,
a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x+y being less than or equal to 3,

R 2 is selected from:
a hydrogen atom,
a COOH carboxylic acid function,
CO—O—R 5 with formula

R 3 is selected from:
a hydrogen atom,
an alcohol function —OH
OC—O—R 6 with formula

R 4 is selected from:
a hydrogen atom or
a methyl group CH 3 ;

R 1 , R 5 and R 6 are identical or different and are selected from:
a linear alkyl group of 1 to 30 carbon atoms, optionally containing 1 to 6 epoxide functions, or
a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide functions, said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atoms,

R 0 , R 1 , R 5 and R 6 optionally comprising one to six substituent(s) selected from —OH, —OR 7 or OCOR 7 , wherein R 7 is an alkyl group of 1 to 3 carbon atoms,
with the proviso that at least one of the OR, R 2 or R 3 groups is an ester function and/or at least one of R 0 , R 1 , R 5 or R 6 comprises at least one epoxide function.
or at least one of the compounds of the following formulae:

to obtain said plastic material.

27 . The process, according to claim 26 , comprising a step of evaporating said solvent from said solution, to obtain said plastic material.

28 . The process, according to claim 26 , wherein the total amount by weight of cellulose acetate and primary plasticizer is from 1 to 50% of the solution by weight, in particular from 10 to 30, preferably 10%.

30 . The process, according to claim 26 , wherein the ratio between the amount of primary plasticizer by weight and cellulose acetate by weight ranges from 1 to 50% by weight, in particular from 10 to 30%, preferably 30%.

31 . The process, according to claim 26 , wherein, in the composition comprising the primary plasticizer, the latter is a compound of formula (1)

formula (1) in which
R is selected from:
a hydrogen atom or
a CO—R1 group,

R 0 is selected from:
a linear alkyl group of 15 carbon atoms, optionally comprising from 1 to 3 epoxide functions or,
a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x+y being less than or equal to 3,

R 2 is selected from:
a hydrogen atom,
a COOH carboxylic acid function,
CO—O—R 5 of formula

R 3 is selected from:
a hydrogen atom,
an alcohol function —OH
OC—O—R 6 with formula

R 4 is selected from:
a hydrogen atom or
a methyl group CH 3 ;

R 1 , R 5 and R 6 are identical or different and are selected from:
a linear alkyl group of 1 to 30 carbon atoms, optionally containing 1 to 6 epoxide functions, or
a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide functions, said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atoms,

R 0 optionally comprising one to six substituent(s) selected from —OH, —OR 7 or OCOR 7 , wherein R 7 is an alkyl group of 1 to 3 carbon atoms,

R 1 , R 5 and R 6 optionally comprising one or two substituents selected from —OH, —OR 7 or OCOR 7 , with the proviso that at least one of the OR, R 2 or R 3 groups is an ester function and/or at least one of
R 0 , R 1 , R 5 or R 6 comprises at least one epoxide function.
or at least one of the compounds of the following formulae:

32 . The process, according to claim 26 , wherein, in the composition comprising the primary plasticizer, the latter is a compound of formula (1)

formula (1) in which
R is selected from:
a hydrogen atom or
a CO—R1 group,

R 0 is selected from:
a linear alkyl group of 15 carbon atoms, optionally comprising from 1 to 3 epoxide functions or,
a linear alkenyl group of 15 carbon atoms, comprising x alkenyl functions, x varying from 1 to 3, comprising y epoxide functions, y varying from 0 to 2, x+y being less than or equal to 3,

R 2 is selected from:
a hydrogen atom,
a COOH carboxylic acid function,
CO—O—R 5 of formula

R 3 is selected from:
a hydrogen atom,
an alcohol function —OH
OC—O—R 6 with formula

R 4 is selected from:
a hydrogen atom or
a methyl group CH 3 ;

R 1 , R 5 and R 6 are identical or different and are selected from:
a linear alkyl group of 1 to 30 carbon atoms, optionally containing 1 to 6 epoxide functions, or
a linear alkenyl group of 2 to 24 carbon atoms, optionally comprising 1 to 6 epoxide functions, said alkenyl group being optionally substituted by an alkyl group of 1 to 5 carbon atoms,

R 1 , R 5 and R 6 optionally comprising one or two substituents selected from —OH, —OR 7 or OCOR 7 , wherein R 7 is an alkyl group of 1 to 3 carbon atoms,
with the proviso that at least one of the OR, R 2 or R 3 groups is an ester function and/or at least one of R 0 , R 1 , R 5 or R 6 comprises at least one epoxide function.
or at least one of the compounds of the following formulae:

33 . The process, according to claim 26 , wherein, in the composition comprising the primary plasticizer, the latter is at least one compound of formula (1b)

formula (1b) in which
R is selected from:
a hydrogen at

Assignees

• Orpia Innovation
• Centre Nat Rech Scient
• Univ Montpellier
• Enscm

Inventors

• Caillol Sylvain
• Jego Lucas
• Lapinte Vincent
• Gartili Adélaïde
• Briou Benoît

Classifications

• C08K5/1515

  Three-membered rings · CPC title

• C08K5/1345

  Carboxylic esters of phenolcarboxylic acids · CPC title

• C08J2301/12

  Cellulose acetate · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C07D303/42

  Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats · CPC title