Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2000-03-21
2001-01-09
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C556S445000
Reexamination Certificate
active
06172252
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to phenol group-containing organosilicon compounds, hereinafter referred to as phenol-functional organosilicon compounds, and to a method for the preparation thereof.
BACKGROUND OF THE INVENTION
A number of phenol-functional organosilicon compounds and methods for their synthesis are known. For example, U.S. Pat. No. 3,622,609 teaches a method for the synthesis of 1,3-bis-&ggr;-(ortho-hydroxyphenyl)propyl- 1,1,3,3-tetramethyldisiloxane by the dimethylsilylation of the hydroxyl group in 2-allylphenol, hydrosilylation polymerization of the reaction product, and then ring opening with sodium hydroxide followed by treatment with sulfuric acid. However, this method cannot provide compounds containing both a phenol group and a functional group other than a phenol group. Japanese Laid Open (Kokai or Unexamined) Patent Application Numbers Hei 2-166123 (166,123/1990) and Hei 2-225524 (225,524/1990) describe a method for synthesizing phenol-functional organosiloxanes by carrying out an addition reaction between an SiH-functional organosiloxane and tert-butoxystyrene (phenolic hydroxyl protected by the tert-butyl group) followed by de-tert-butylation in the presence of a strong acid. This method is, however, unable to produce compounds that contain the phenol group and alkenyl in the same molecule and also suffers from the disadvantage that the siloxane chain is susceptible to cleavage by the strong acid. Otherwise, Japanese Laid Open (Kokai or Unexamined) Patent Application Numbers Sho 62-275116 (275,116/1987) and Sho 61-84022 (84,02211986) describe phenol-functional silanes, but these compounds are limited to phenol-functional trialkylsilanes and do not include alkoxysilyl-functional or silanol-functional species. Moreover, the synthetic methods disclosed therein are very complex and do not provide high yields.
The present inventors have already disclosed organosiloxanes that contain both alkenyl and the phenol group as well as a method for the synthesis thereof (Japanese Patent Application Number Hei 10-294580 (294,580/1998)). Unfortunately, this method carries with it the risk that the alkenyl group-containing organosiloxane product will polymerize during the purification phase. In addition, this method cannot be used to synthesize compounds that contain both the phenol group and alkoxysilyl group or silanol group in the same molecule.
SUMMARY OF THE INVENTION
In specific terms, an object of this invention is to provide novel phenol-functional organosilicon compounds containing both a phenol group and alkoxysilyl, alkenyl, or silanol group in the same molecule. An additional object of this invention is to provide a method for preparing the novel phenol-functional organosilicon compounds.
The present invention is directed to a phenol-functional organosilicon compound having the formula:
wherein A is hydrogen or a residue afforded by the removal of n hydroxyl groups from an m-valent alcohol, each R is independently a monovalent hydrocarbon group free of aliphatic unsaturation, each R
1
is independently a divalent hydrocarbon group containing at least 2 carbon atoms, m and n are natural numbers wherein m≧n, p is 0 or 1, and Y is a phenol group having the formula:
wherein R
3
is alkyl and q is from 0 to 4.
The present invention is also directed to a method of preparing a phenol-functional organosilicon compound, said method comprising the steps of:
(A) reacting an aliphatically unsaturated SiH-functional organosilicon compound in the presence of a hydrosilylation catalyst to form an addition reaction product, wherein the SiH-functional organosilicon compound has the formula:
wherein each R is independently a monovalent hydrocarbon group free of aliphatic unsaturation, R
2
is an aliphatically unsaturated monovalent hydrocarbon group, R
3
is alkyl, p is 0 or 1, and q is from 0 to 4; and
(B) reacting the addition reaction product with an alcohol or water to produce a phenol-functional organosilicon compound, wherein the alcohol has the formula A(OH)
n
wherein A is hydrogen or a residue afforded by the removal of n hydroxyl groups from an m-valent alcohol and m and n are natural numbers wherein m≧n.
The phenol-functional organosilicon compounds of this invention contain both a phenol group and an alkoxysilyl, alkenyl, or silanol group in the same molecule. As a result, curable silicone compositions containing these phenol-functional organosilicon compound have excellent adhesion to glasses, organic resins such as phenolic resins and epoxy resins, and metals such as copper, aluminum, and stainless steel. The method of this invention is a highly productive method for producing the novel phenol-functional organosilicon compound.
The phenol-functional organosilicon compound of this invention can be used as adhesion promoters in curable silicone compositions. In particular the phenol-functional organosilicon compound of the instant invention is highly suitable for use as an adhesion promoter in addition reaction-curing silicone compositions. The phenol-functional organosilicon compound of this invention can also be used as an optical matching oil and as a polymerization terminator.
DETAILED DESCRIPTION OF THE INVENTION
A phenol-functional organosilicon compound according to the present invention has the formula:
wherein A is hydrogen or a residue afforded by the removal of n hydroxyl groups from an m-valent alcohol, each R is independently a monovalent hydrocarbon group free of aliphatic unsaturation, each R
1
is independently a divalent hydrocarbon group containing at least 2 carbon atoms, m and n are natural numbers wherein m≧n, p is 0 or 1, and Y is a phenol group having the formula:
wherein R
3
is alkyl and q is from 0 to 4.
In the formula of the phenol-functional organosilicon compound of the present invention, the subscripts m and n are typically in the range from 1 to 5, and m must be greater than or equal to n.
Examples of alcohol-derived residues represented by A include, but are not limited to, the following monovalent, divalent, and trivalent groups: unsubstituted hydrocarbyl, alkyloxyalkylene, alkenyloxyalkylene, phenyloxyalkylene, hydroxy-functional hydrocarbyl, hydroxy-functional alkyloxyalkylene, and hydroxy-functional alkenyloxyalkylene. The following are examples of residues afforded by removal of the hydroxyl group from a monovalent alcohol: methyl, ethyl, propyl, butyl, hexyl, allyl, butenyl, hexenyl, and propylene oxide. Residues afforded by the removal of 1 hydroxyl group from a divalent alcohol are exemplified by 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl, 3-hydroxybutyl, and 3-allyloxy-2-hydroxypropyl. Residues afforded by the removal of 2 hydroxyl groups from a divalent alcohol are exemplified by ethylene, propylene, butylene, hexylene, and ethyleneoxypropylene. Residues afforded by the removal of 1 hydroxyl group from a trivalent alcohol are exemplified by dihydroxypropyl, dihydroxybutyl, and dihydroxyhexyl. Residues afforded by the removal of 2 hydroxyl groups from a trivalent alcohol are exemplified by hydroxypropylene, hydroxybutylene, and hydroxyhexylene.
Preferred embodiments of the group A are as follows: the hydrogen atom; alkyl such as methyl and ethyl and aliphatically unsaturated groups such as allyl, butenyl, and hexenyl among the residues afforded by removal of the hydroxyl group from a monovalent alcohol; and hydroxyl-functional alkenyloxyalkylene groups such as 3-allyloxy-2-hydroxypropyl among the residues afforded by removal of1 hydroxyl group from a divalent alcohol. Aliphatically unsaturated groups are particularly preferred from the perspective of their adhesion-promoting performance.
Examples of the monovalent hydrocarbon groups represented by R include, but not limited to, alkyl such as methyl, ethyl, butyl, pentyl, and hexyl; aryl such as phenyl, tolyl, and xylyl; and aralkyl such as benzyl and phenethyl. Examples of the divalent hydrocarbon groups represented by R
1
include, but not limited to, alkylene groups such as ethylene, propylene, butylene, and h
Amako Masaaki
Okawa Tadashi
Dow Corning Toray Silicone Co. Ltd.
Milco Larry A.
Shaver Paul F.
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