Hydrocarbon-based polymers bearing an alkoxysilane end group

Patent metadata

Field	Value
Publication number	US-10662265-B2
Application number	US-201414906737-A
Country	US
Kind code	B2
Filing date	Jul 22, 2014
Priority date	Jul 23, 2013
Publication date	May 26, 2020
Grant date	May 26, 2020

Abstract

Polymer of formula (1) bearing an alkoxysilane end group:

in which:
is a double or single bond; each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is H, a halo, an alkoxycarbonyl or an alkyl, m and p are each from 0 to 5, each of R and R′ is an alkyl, Z is an alkylene, optionally interrupted with COO, q is 0 or 1, r is 0, 1 or 2, and n is such that the number-average molar mass of the polymer (1) is from 400 to 50 000 g/mol, and the polydispersity index of the polymer (1) is from 1.0 to 2.0.

Preparation by ring-opening metathesis polymerization.
Use as an adhesion promoter or a reactive plasticizer.

First claim

The invention claimed is:

1. A hydrocarbon-based polymer bearing an alkoxysilane end group, said hydrocarbon-based polymer being of formula (1′):

in which:
the groups R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each, independently of each other, a hydrogen, a halo group, an alkoxycarbonyl group or an alkyl group, the groups R 1 to R 6 possibly being linked together as members of the same ring or heterocycle comprising at least one carbon-carbon double bond,
m and p are integers each within a range from 0 to 5, the sum m+p being within a range from 0 to 10,
R and R′, which may be identical or different, each represent a linear or branched, alkyl group comprising from 1 to 4 carbon atoms,
Z is a divalent group chosen from alkylene groups interrupted with an ester function, and comprising from 1 to 22 carbon atoms,
q is an integer equal to 1,
r is an integer equal to 0, 1 or 2, and
n is an integer such that the number-average molar mass Mn of the hydrocarbon-based polymer of formula (1′) is within a range from 400 to 50,000 g/mol, and the polydispersity index (PDI) of the hydrocarbon-based polymer of formula (1′) is within a range from 1.0 to 2.0.

2. The hydrocarbon-based polymer bearing an alkoxysilane end group as claimed in claim 1 , such that the group of formula —[Z] q —Si(R) r (OR′) 3-r is —CO—O—(CH 2 ) 3 Si(OCH 3 ) 3 ); or —CO—O—(CH 2 ) 3 SiCH 3 (OCH 3 ) 2 ).

3. The hydrocarbon-based polymer bearing an alkoxysilane end group as claimed in claim 1 , said hydrocarbon-based polymer being of formula (2):

wherein each carbon-carbon bond of the chain noted as is a single bond and the bond means that the bond is geometrically oriented on one side or the other relative to the double bond, cis (Z) or trans (E).

4. The hydrocarbon-based polymer bearing an alkoxysilane end group as claimed in claim 3 , wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are hydrogen.

5. The hydrocarbon-based polymer bearing an alkoxysilane end group as claimed in claim 1 , wherein each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are hydrogen.

6. A process for preparing at least one hydrocarbon-based polymer as claimed in claim 1 , said process comprising at least one ring-opening metathesis polymerization in the presence of:
at least one metathesis catalyst,
at least one chain-transfer agent (CTA) chosen from the group formed by alkenylsilanes bearing a monosubstituted carbon-carbon double bond, and
at least one compound chosen from compounds comprising at least one hydrocarbon-based ring, said ring comprising at least one carbon-carbon double bond, and substituted derivatives of this compound, said compound being of formula (7):

in which:
each carbon-carbon bond of the chain noted as is a double bond or a single bond, in accordance with the valency rules of organic chemistry;
the groups R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each, independently of the other groups or otherwise, a hydrogen, a halo group, an alkoxycarbonyl group or an alkyl group, the groups R 1 to R 6 possibly being linked together as members of the same saturated or unsaturated ring or heterocycle,
m and p are integers each within a range from 0 to 5, the sum m+p itself being within a range from 0 to 10,

said polymerization being performed for a time of less than 2 hours, when R 1 and R 6 are both equal to H; and said polymerization being performed for a time of less than or equal to 30 hours when at least one from among R 1 and R 6 is not H.

7. The preparation process as claimed in claim 6 , such that the chain-transfer agent has the formula CH 2 ═CH—[Z] q —Si(R) r (OR′) 3-r in which:
R and R′, which may be identical or different, each represent a linear or branched alkyl group comprising from 1 to 4 carbon atoms,
Z is a divalent alkylene group interrupted with an ester function, and comprising from 1 to 22 carbon atoms,
q is an integer equal to 1, and
r is an integer equal to 0, 1 or 2.

8. The preparation process as claimed in claim 6 , such that the chain-transfer agent is: CH 2 ═CH—CO—O—(CH 2 ) 3 Si(OCH 3 ) 3 ; or CH 2 ═CH—CO—O—(CH 2 ) 3 SiCH 3 (OCH 3 ) 2 .

9. The preparation process as claimed in claim 6 , said process being such that the mole ratio of the CTA to the compound comprising at least one hydrocarbon-based ring is within a range from 1 to 10 mol %.

10. The preparation process as claimed in claim 6 , said process also comprising at least one additional hydrogenation of double bonds.

11. The preparation process as claimed in claim 10 , such that the additional hydrogenation is performed by catalytic hydrogenation, under hydrogen pressure and in the presence of a hydrogenation catalyst.

12. In an adhesion promoter comprising a hydrocarbon-based polymer, the improvement wherein the hydrocarbon-based polymer is one according to claim 1 .

13. In an adhesive composition comprising a reactive plasticizer, the improvement wherein the reactive plasticizer is a hydrocarbon-based polymer according to claim 1 .

Assignees

• Bostik Sa

Inventors

• Michaud Guillaume
• Simon Frederic
• Fouquay Stephane
• Diallo Abdou Khadri
• Guillaume Sophie
• Carpentier Jean-Francois

Classifications

• C08G2261/76

  crosslinking · CPC title

• C08G2261/135

  Cross-linked structures · CPC title

• C08G2261/724

  Hydrogenation · CPC title

• C08G2261/3322

  derived from cyclooctene · CPC title

• C08G2261/726

  Silylation · CPC title