Radiation activated hydrosilation reaction

• US 5,145,886 A
• Filed: 10/22/1990
• Issued: 09/08/1992
• Est. Priority Date: 05/19/1988
• Status: Expired due to Term

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Oxman, Joel D., Boardman, Larry D.
• Primary Examiner(s): McCamish, Marion E.
• Assistant Examiner(s): BERMAN, SUSAN W
• Application Number:
  US07/602,411
• Time in Patent Office: 687 Days
• Field of Search: 528/15, 528/31, 528/32, 522/66, 522/99
• US Class Current: 522/66
• CPC Class Codes: A61K 6/76 comprising silicon-containing compounds
• CPC Class Codes: A61K 6/78 Pigments
• CPC Class Codes: A61K 6/90 Compositions for taking dental impressions
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/14 containing silicon bound to oxygen-containing groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/24 halogen-containing groups
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08G 77/70 Siloxanes defined by use of the MDTQ nomenclature
• CPC Class Codes: C08K 5/0091 Complexes with metal-heteroatom-bonds
• CPC Class Codes: C08L 2666/52 Metal-containing compounds
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

A process for the actinic radiation-activated addition reaction of a compound containing silicon-bonded hydrogen with a compound containing aliphatic unsaturation, said addition being referred to as hydrosilation, comprising using, as a platinum hydrosilation catalyst, a complex represented by the formula: ##STR1## wherein R¹ and R² independently represent hydrogen, an alkyl group, or an aryl group, R³, R⁴, R⁵, and R⁶ independently represent an alkyl group, an aryl group, or an alkoxy group. The invention also includes novel compositions, capable of undergoing hydrosilation, containing the platinum complexes disclosed herein. An important application of the process and compositions of the invention is as a visible light curable impression material for dental applications.

Claims

1. A hydrosilation process which comprises reacting a composition comprising a compound having aliphatic unsaturation and a compound containing at least one silicon-bonded hydrogen atom and not havng more than three hydrogen atoms attached to any one silicon atom, in the presence of a platinum (II) β

-diketonate complex catalyst, wherein said reaction is carried out by means of exposing said composition to actinic radiation having a wavelength of about 200 nm to about 800 nm.

2. The process of claim 1, wherein the platinum complex catalyst is represented by the formula:

##STR14## wherein R¹ and R² independently represent hydrogen, an alkyl group, or an aryl group, and R³, R⁴, R⁵, and R⁶ independently represent an alkyl group, an aryl group, or an alkoxy group.

3. The process of claim 1, wherein the composition comprises from 0.1 to 10.0 equivalent weights of the compound having silicon-bonded hydrogen per equivalent weight of the compound having aliphatic unsaturation, and, per 1,000,000 parts by weight of the total composition, from about 5 to about 5,000 parts by weight of the platinum complex catalyst.

4. The process of claim 1, wherein the compound containing aliphatic unsaturation is a polyorganosiloxane having the general formula:

##STR15## wherein each R⁹ independently represents a non-halogenated or halogenated ethylenically-unsaturated group, a non-halogenated or halogenated alkyl group or cycloalkyl group, or an aryl group, at least 70% of all R⁹ groups being methyl groups, but no more than 10% of all R⁹ groups being vinyl or other alkenyl, and at least one of the R⁹ radicals being vinyl or other alkenyl,

h represents a number having a value from about 1 to about 3000, and

g represents 0, 1, 2, or 3.

5. The process of claim 1, wherein the compound containing silicon-bonded hydrogen is a polyorganohydrosiloxane having the general formula:

##STR16## wherein each R¹¹ independently represents an alkyl group, a cycloalkyl group, a phenyl group, a hydroxyalkyl group, a (polyalkoxy)alkyl group, or hydrogen, at least one but no more than 50% of all R¹¹ groups being hydrogen,

m represents 0, 1, 2 or 3, and

n represents a number having an average value from about 1 to about 3000.

6. The process of claim 1, wherein the compound having aliphatic unsaturation is one having olefinic unsaturation.