Grafted telechelic polyisobutylenes possessing reactive functionality, processes for preparing the same and curable compositions comprising the same

Patent metadata

Field	Value
Publication number	US-9790309-B2
Application number	US-201414488824-A
Country	US
Kind code	B2
Filing date	Sep 17, 2014
Priority date	Apr 27, 2012
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

Disclosed are reactive functionalized, PIB grafted polymers having an architecture of one or more pendent polyisobutylene moieties grafted on to an organic backbone, wherein the backbone is not polyisobutylene and contains at least one telechelic, reactive functionality. Also a process for making the reactive functionalized, PIB grafted polymer s and curable compositions comprising the reactive functionalized, PIB grafted polymers.

First claim

What is claimed:

1. A reactive functionalized, PIB grafted polymer comprising:
an organic backbone Z, the backbone including one or more aliphatic groups, one or more aromatic groups, one or more heteroatoms or any combination thereof, wherein the backbone Z is not polyisobutylene; at least one reactive functionality terminal to the backbone; and at least two polyisobutylene groups Y pendant from the organic backbone Z,
wherein the polymer is represented by one of the following formulas;

wherein organic backbone Z has a linear chain structure having 1 to about 50 atoms selected from the group consisting of C, H, N, O and S;
each M is independently selected from a covalent bond or an organic structure having 1 to about 20 atoms selected from the group consisting of C, H, N, O and S;
X, X 1 , X 2 , X 3 and X 4 are each independently H or a reactive functionality selected from acrylate, methacrylate, acrylamide, allyl, styrenic, vinyl ether, maleimide and N-vinylamide, but at least one of X, X 1 , X 2 , X 3 and X 4 in any formula must be a reactive functionality;
Y is a polyisobutylene group;
L connects one polyisobutylene group to one atom of the Z organic backbone or one atom of the M portion and each L is independently selected from a covalent bond or an organic structure having 1 to about 30 atoms selected from the group consisting of C, H, N, O and S;
R1 and R2 are each independently selected organic segments having 1 to about 30 atoms selected from the group consisting of C, H, N, O and S;
m is an integer from 2-10; and
n is an integer from 1-10.

2. The polymer of claim 1 , having a weight average molecular weight (Mw) of about 1,000 to about 30,000.

3. The polymer of claim 1 , in liquid form at room temperature.

4. The polymer of claim 1 , represented by the formula;

wherein
X 1 and X 2 are each independently H or a reactive functionality selected from acrylate, methacrylate, acrylamide, allyl, styrenic, vinyl ether, maleimide and N-vinylamide, but at least one of X 1 and X 2 must be a reactive functionality.

5. The polymer of claim 4 , wherein both X 1 and X 2 comprise an independently selected reactive functionality.

6. The polymer of claim 4 , wherein X 1 and X 2 are each a reactive functionality independently selected from acrylate or methacrylate.

7. The polymer of claim 1 , represented by the formula;
(Y-L) m -Z-(M-X) n
wherein
each X is independently H or a reactive functionality selected from acrylate, methacrylate, acrylamide, allyl, styrenic, vinyl ether, maleimide and N-vinylamide but at least one X must be a reactive functionality; and
L connects the polyisobutylene group Y to one atom of the Z organic backbone and each L is independently selected from a covalent bond or a structure having 1 to about 30 atoms selected from the group consisting of C, H, N, O and S.

8. The polymer of claim 7 , wherein L is selected from a covalent bond, C 1-5 alkyl, a heteroatom, ester, thioester, amide, imide, cyclic imide, ketone, carboxyl, urethane, carbonate, urea and combinations thereof.

9. The polymer of claim 1 , represented by the formula;

wherein
each Y is a polyisobutylene group.

10. The polymer of claim 9 , wherein all of X 1 , X 2 , X 3 and X 4 comprise an independently selected reactive functionality.

11. The polymer of claim 9 , wherein all of X 1 , X 2 , X 3 and X 4 comprise an independently selected acrylate reactive functionality or methacrylate reactive functionality.

12. The polymer of claim 9 , wherein R1 and R2 are the same.

13. A curable composition comprising the polymer of claim 1 .

14. The curable composition of claim 13 , further comprising a cure-inducing component and a co-reactant component.

15. Cured reaction products of the curable composition of claim 13 .

16. A method of making the reactive functionalized, PIB grafted polymer of claim 1 , comprising:
providing polyisobutylenesuccinic anhydride;
providing at least compound selected from a diacrylate, a monomethacrylate, an acrylamide, an amino alcohol, an allyl substituted monomer and a vinyl ether;
optionally providing one or more of a solvent, a Lewis acid and a Lewis base; and
reacting the polyisobutylenesuccinic anhydride with the at least compound selected from a diacrylate, a monomethacrylate, an acrylamide, an amino alcohol and an allyl substituted monomer.

17. The polymer of claim 1 , wherein Z comprises one or more aliphatic groups, one or more aromatic groups, one or more heteroatoms or any combination thereof; and Z can include one or more of branching, pendant aliphatic groups, pendant aromatic groups and pendant heteroatoms.

18. The polymer of claim 1 comprising L, wherein Y consists of a polyisobutylene group and L is selected from a covalent bond, C 1-5 alkyl, ester, thioester, amide, imide, cyclic imide, ketone, carboxyl, urethane, carbonate, urea and combinations thereof.

19. A reactive functionalized, PIB grafted polymer selected from the following structures:

20. The polymer of claim 1 comprising R 1 and R 2 , wherein Y consists of a polyisobutylene group and R1 and R2 are each independently selected from the group consisting of one or more C1-30 alkyl, C6-10 aryl, one or more heteroatoms selected from N, O or S atoms, or any combination thereof.

21. The polymer of claim 1 , wherein:
the Z organic backbone is selected from the group consisting of one or more aliphatic groups, one or more aromatic groups, one or more heteroatoms or any combination thereof and Z can include one or more of branching, pendant aliphatic groups, pendant aromatic groups and pendant heteroatoms;
M is selected from the group consisting of a covalent bond, heteroatom, C1-10 alkyl, C6-10 aryl, amide, urethane, urea, C3-6 cycloaliphatic, C6-10 cycloaryl, polyether and combinations thereof, and M may include within that structure one or more linear, branched or cyclic portions, one or more saturated, unsaturated or aromatic portions, one or more substituents selected from carbonyl, amide, alkyl, C3-6 cycloalkyl, C6-10 cycloaryl, one or more N, O or S atoms, or any combination thereof;
Y consists of a polyisobutylene group;
L is selected from the group consisting of a covalent bond, C 1-5 alkyl, ester, thioester, amide, imide, cyclic imide, ketone, carboxyl, urethane, carbonate, urea and combinations thereof; and
R1 and R2 are each independently selected from the group consisting of one or more C1-30 alkyl, C6-10 aryl, one or more heteroatoms selected from N, O or S atoms, or any combination thereof.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Sridhar Laxmisha
• Shah Smita
• Messana Andrew D
• Jacobine Anthony F

Classifications

• C08F290/042 Primary

  Polymers of hydrocarbons as defined in group C08F10/00 · CPC title

• C08F269/00 Primary

  Macromolecular compounds obtained by polymerising monomers on to polymers of heterocyclic oxygen-containing monomers as defined in group C08F24/00 · CPC title

• C08F8/14

  Esterification · CPC title

• C08L51/06

  grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond · CPC title

• C08F265/10

  on to polymers of amides or imides · CPC title