Polymers with graft .alpha.-alkylacrylate functionality

• US 4,504,629 A
• Filed: 07/20/1983
• Issued: 03/12/1985
• Est. Priority Date: 07/20/1983
• Status: Expired due to Term

• Current Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Original Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Inventors: Nakos, Steven T., Lien, Samuel Q. S.
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US06/515,702
• Time in Patent Office: 601 Days
• Field of Search: 525/288, 525/193, 525/284, 525/478, 525/479
• US Class Current: 525/288
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• CPC Class Codes: C07F 7/0896 Compounds with a Si-H linkage
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C08C 19/25 Incorporating silicon atoms into the molecule
• CPC Class Codes: C08F 290/128 Polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
• CPC Class Codes: C08F 299/00 Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/50 by carbon linkages C08G77/485 takes precedence
• CPC Class Codes: C08L 83/06 containing silicon bound to oxygen-containing groups C08L83/12 takes precedence
• CPC Class Codes: H05K 3/285 Permanent coating compositions

Abstract

Polymers having α-alkylacrylate functionality may be prepared by hydrosilating an aliphatically unsaturated polymer with a grafting agent of structure (A) or (B): ##STR1## where R¹ is an alkyl group; R² is a divalent group nonreactive under hydrosilation conditions; n is 0, 1, 2, 3, or 4; x and y are 0, 1, 2, 3 or 4 and x+y=1, 2, 3 or 4; and, the R³ groups are the same or different alkyl, substituted alkyl, aryl, substituted aryl or ##STR2## groups. Preferred olefinically unsaturated polymers include homopolymers and copolymers of butadiene or alkyl substituted butadiene and polyorganosiloxanes with unsaturated hydrocarbyl groups such as vinyl or allyl.

Claims

1. A method of adding α

-alkylacrylate functionality to an aliphatically unsaturated polymer, the method comprising reacting at temperatures between about 0°

C. and about 100°

C. a grafting agent consisting essentially of a compound selected from (A), (B) and mixtures thereof with said aliphatically unsaturated polymer in the presence of a hydrosilation catalyst selected from platinum-based catalysts and rhodium complex catalysts, said grafting agent compounds (A) and (B) having the respective structures;

##STR8## where R¹ is an alkyl group;

R² is a divalent group nonreactive under hydrosilation conditions;

n is 0, 1, 2, 3, or 4;

x and y are 0, 1, 2, 3 or 4 and x+y=1, 2, 3 or 4; and

, the R³ groups are the same or different alkyl, substituted alkyl, aryl, substituted aryl or ##STR9## groups.

2. A method as in claim 1 wherein said catalyst is chloroplatinic acid.

3. A method as in claim 1 wherein R² is alkyleneoxy, polyalkyleneoxy, alkylene, alkyleneoxyalkylene, arylene, alkylarylene, arylalkylene, or alkenylene.

5. A method as in claim 1 wherein said unsaturated polymer is selected from homopolymers and copolymers of butadiene or alkyl-substituted butadienes.

6. A method as in claim 5 wherein said unsaturated polymer is selected from block copolymers of styrene and butadiene or styrene and isoprene.

7. A method as in claim 1 wherein said unsaturated polymer is polyorganosiloxane having a plurality of unsaturated hydrocarbyl groups.

8. A method as in claim 7 wherein said polyorganosiloxane unsaturated hydrocarbyl groups are allyl or vinyl groups.

4. A method as in claim 4 wherein R² is propylene, propyleneoxy or ethyleneoxypropylene.

9. A polymer conprising the hydrosilation reaction product of an aliphatically unsaturated polymer and a grafting agent consisting essentially of a compound of structure (A), (B), or mixtures thereof:

##STR10## where R¹ is an alkyl group;

R² is a divalent group nonreactive under hydrosilation reaction conditions;

n is 0, 1, 2, 3, or 4;

x and y are 0, 1, 2, 3 or 4 and x+y=1, 2, 3 or 4; and

, the R³ groups are the same or different alkyl, substituted alkyl, aryl, substitute aryl or ##STR11## groups, said hydrosilation reaction being conducted in the presence of a platinium-based or rhodium complex hydrosilation catalyst at a temperature of between about 0°

C. and about 100°

C.

10. A polymer as in claim 9 wherein R¹ is methyl.

11. A polymer as in claim 9 wherein R² is alkyleneoxy, polyalkyleneoxy, alkylene, alkyleneoxyalkylene, arylene, alkylarylene or arylalkylene, or alkenylene.

12. A polymer as in claim 11 wherein R² is propylene, propyleneoxy or ethyleneoxypropylene.

13. A polymer as in claim 9 wherein said unsaturated polymer is selected from homopolymers and copolymers of butadiene or alkyl-substituted butadienes.

14. A polymer as in claim 13 wherein said unsaturated polymer is selected from block copolymers of styrene and butadiene or styrene and isoprene.

15. A polymer as in claim 9 wherein said unsaturated polymer is polyorganosiloxane having a plurality of unsaturated hydrocarbyl groups.

16. A polymer as in claim 15 wherein said polyorganosiloxane unsaturated hydrocarbyl groups are allyl or vinyl groups.