Grafted polymer bearing pendent cyclic carbonate functional groups
A modified polymer is obtained by grafting at least one compound of formula (I) to at least one unsaturation of the chain of an initial polymer in which Q represents a dipole comprising at least one nitrogen atom; A represents an arenediyl ring, optionally substituted by one or more hydrocarbon-based chains, which are identical or different, independent of one another, and are optionally substituted or interrupted by one or more heteroatoms; E represents a divalent hydrocarbon-based bonding group which may optionally contain one or more heteroatoms; R 1 , R 2 and R 3 represent, independently of one another, a hydrogen atom or a hydrocarbon-based chain which is optionally substituted or interrupted by one or more heteroatoms; and n is an integer having a value greater than or equal to 1.
1. A modified polymer obtained by grafting at least one compound of formula (I) to at least one unsaturation of a chain of an initial polymer
in which:
Q represents a dipole comprising at least one nitrogen atom;
A represents an arenediyl ring, optionally substituted by one or more hydrocarbon-based chains, which are identical or different, independent of one another, and are optionally substituted or interrupted by one or more heteroatoms;
E represents a divalent hydrocarbon-based bonding group which may optionally contain one or more heteroatoms;
R 1 , R 2 and R 3 represent, independently of one another, a hydrogen atom or a hydrocarbon-based chain which is optionally substituted or interrupted by one or more heteroatoms; and
n is an integer having a value greater than or equal to 1.
2. The modified polymer according to claim 1 , wherein the initial polymer is an elastomer.
3. The modified polymer according to claim 2 , wherein the initial polymer is a diene elastomer is selected from the group consisting of ethylene/propylene/diene monomer copolymers, butyl rubber, natural rubber, synthetic polyisoprenes, polybutadienes, butadiene copolymers, isoprene copolymers and mixtures thereof.
4. The modified polymer according to claim 1 , wherein a molar degree of grafting of the compound of formula (I) is within a range extending from 0.01% to 15%.
5. The modified polymer according to claim 1 , wherein Q is a group of formula (II), (III) or (IV)
in which:
the symbol * represents attachment of Q to A; and
R 4 , R 5 and R 6 are independently selected from the group consisting of a hydrogen atom, a linear or branched C 1 -C 20 alkyl, a C 3 -C 30 cycloalkyl which is optionally substituted by a hydrocarbon-based chain, and a C 6 -C 20 aryl which is optionally substituted by a hydrocarbon-based chain.
6. The modified polymer according to claim 1 , wherein A is a C 6 -C 14 arenediyl ring optionally substituted by one or more hydrocarbon-based chains, which are identical or different, independent of one another, and are optionally substituted or interrupted by one or more heteroatoms.
7. The modified polymer according to claim 1 , wherein the compound of formula (I) is selected from the group consisting of compounds of formulae (Ia) and (lb)
in which:
one group selected from R 7 to R 11 of the formula (Ia) and one group selected from R 7 to R 13 of the formula (Ib) denotes the following group of formula (V):
in which:
R groups other than the one group selected from R 7 to R 11 of the formula (Ia) and R groups other than the one group selected from R 7 to R 13 of the formula (Ib), which are identical or different, independently of one another represent a hydrogen atom or a linear or branched, hydrocarbon-based chain which is optionally substituted or interrupted by one or more heteroatoms.
8. The modified polymer according to claim 5 , wherein the compound of formula (I), when Q is a nitrile oxide, is selected from the compounds of formula (VI)
in which:
E represents a divalent hydrocarbon-based bonding group which may optionally contain one or more heteroatoms;
R 1 , R 2 and R 3 represent, independently of one another, a hydrogen atom or a hydrocarbon-based chain which is optionally substituted or interrupted by one or more heteroatoms; and
n is an integer having a value greater than or equal to 1.
9. The modified polymer according to claim 1 , wherein n=1, 2, 3 or 4.
10. The modified polymer according to claim 1 , wherein E is selected from the group consisting of —R— and —OR—, where R is a linear or branched C 1 -C 24 alkylene.
11. The modified polymer according to claim 1 , wherein R 1 , R 2 and R 3 represent, independently of one another, a hydrogen atom or a linear or branched C 1 -C 24 alkyl.
12. The modified polymer according to claim 1 , wherein the compound of formula (I) is selected from the group consisting of the compound of formula (VII) and the compound of formula (VIII)
13. A process for preparing the modified polymer according to claim 1 , the process process comprising a step of:
grafting, to the initial polymer comprising at least one unsaturation, the compound of formula (I) by [3+2] cycloaddition of Q of the compound of formula (I) to the unsaturation.
14. The process according to claim 13 , wherein the compound of formula (I) is selected from the group consisting of the compound of formula (VII) and the compound of formula (VIII)
15. A composition comprising at least one modified polymer according to claim 1 and at least one additive.