Method for the preparation of a fluorine-containing organopolysiloxane

• US 5,639,845 A
• Filed: 11/01/1995
• Issued: 06/17/1997
• Est. Priority Date: 06/10/1993
• Status: Expired due to Term

• Current Assignee: Shin-Etsu Chemical Company Limited
• Original Assignee: Shin-Etsu Chemical Company Limited
• Inventors: Inomata, Hiroshi, Ishida, Kouichi, Yamamoto, Yasushi, Koike, Noriyuki, Tarumi, Yasuo
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US08/551,339
• Time in Patent Office: 594 Days
• Field of Search: 528/15, 556/479, 586/450, 586/488, 586/454, 586/462
• US Class Current: 528/15
• CPC Class Codes: C08G 77/385 containing halogens

Abstract

A novel and very efficient method is disclosed for the introduction of perfluoroalkyl groups into an organopolysiloxane by utilizing the hydrosilation reaction with an organohydrogenpolysiloxane. Different from the conventional but inefficient hydrosilation reaction using a perfluoroalkyl-substituted ethylene as the olefin compound, the inventive method utilizes a propene-1 3-substituted by a perfluoroalkyl group compound as the olefin compound to react with an organohydrogenpolysiloxane by which a very high efficiency in the hydrosilation reaction can be obtained without side reactions which otherwise greatly decrease the yield of the desired perfluoroalkyl-containing organopolysiloxane product.

Claims

1. A method for the preparation of an organopolysiloxane compound having a 3-(perfluoroalkyl)propyl group represented by the general formula Rf--CH₂ CH₂ CH₂ --, Rf being a perfluoroalkyl group having from 1 to 10 carbon atoms, bonded to a silicon atom of the organopolysiloxane which comprises the steps of:

(a) blending an organohydrogenpolysiloxane having, in a molecule, at least one difunctional siloxane unit of the unit formula RSi(H)O, in which R is a monovalent hydrocarbon group free from aliphatic unsaturation having 1 to 10 carbon atoms, and a 3-substituted propene-1 compound represented by the general formula

space="preserve" listing-type="equation">Rf--CH.sub.2 --CH═

CH.sub.2,

in which Rf has the same meaning as defined above, with admixture of a catalytic compound for the hydrosilation reaction to form a reaction mixture; and

(b) heating the reaction mixture.

2. The method as claimed in claim 1 in which the catalytic compound is a compound of a noble metal element belonging to the VIIIth Group of the Periodic Table.

3. The method as claimed in claim 2 in which the amount of the catalytic compound is in the range from 1×

10^-3 to 1×

10^-5 mole calculated as the noble metal element per mole of the silicon-bonded hydrogen atoms in the organohydrogenpolysiloxane.

4. The method as claimed in claim 1 in which the reaction mixture is diluted by the admixture of an organic solvent.

5. The method as claimed in claim 4 in which the organic solvent is trifluoromethyl benzene or 1,3-bis(trifluoromethyl) benzene.

6. The method as claimed in claim 1 in which the temperature of heating in step (b) is in the range from 40°

C. to 160°

C.

7. An organopolysiloxane compound having a 3-(perfluoroalkyl)propyl group represented by the general formula Rf--CH₂ CH₂ CH₂ --, Rf being a perfluoroalkyl group having from 1 to 10 carbon atoms, bonded to a silicon atom of the organopolysiloxane which is a product prepared by the process comprising the steps of:

(a) blending an organohydrogenpolysiloxane having, in a molecule, at least one difunctional siloxane unit of the unit formula RSi(H)O, in which R is a monovalent hydrocarbon group free from aliphatic unsaturation having 1 to 10 carbon atoms, and a 3-substituted propene-1 compound represented by the general formula

space="preserve" listing-type="equation">Rf--CH.sub.2 --CH═

CH.sub.2,

in which Rf has the same meaning as defined above, with admixture of a catalytic compound for the hydrosilation reaction to form a reaction mixture; and

(b) heating the reaction mixture.

8. The organopolysiloxane compound as claimed in claim 7 in which the catalytic compound is a compound of a noble metal element belonging to the VIIIth Group of the Periodic Table.

9. The organopolysiloxane compound as claimed in claim 8 in which the amount of the catalytic compound is in the range from 1×

10^-3 to 1×

10^-5 mole calculated as the noble metal element per mole of the silicon-bonded hydrogen atoms in the organohydrogenpolysiloxane.

10. The organopolysiloxane compound as claimed in claim 7 in which the reaction mixture is diluted by the admixture of an organic solvent.

11. The organopolysiloxane compound as claimed in claim 10 in which the organic solvent is trifluoromethyl benzene or 1,3-bis(trifluoromethyl)ben-zene.

12. The organopolysiloxane compound as claimed in claim 7 in which the temperature of heating in step (b) is in the range from 40°

C. to 160°

C.