Cyclic organosilicon endcapper having one aliphatic...

Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing

Reexamination Certificate

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C556S460000, C556S436000, C556S462000

Reexamination Certificate

active

06303811

ABSTRACT:

FIELD OF THE INVENTION
A cyclic organosilicon compound comprising one aliphatic unsaturation described by formula
where each R is an independently selected hydrocarbon radical free from aliphatic unsaturation comprising 1 to about 18 carbon atoms; each X is independently selected from the group consisting of halogen, alkoxy, acyloxy, and ketoximo; m is an integer from 2 to 7; p is an integer from 0 to 6; m+p is an integer from 2 to 8; n is 0, 1, or 2; each Z is independently selected from the group consisting of divalent hydrocarbon radicals free of aliphatic unsaturation comprising about 2 to 18 carbon atoms and a combination of divalent hydrocarbon radicals and siloxane segments; and Y is selected from the group consisting of hydrocarbon radicals comprising one aliphatic unsaturation and 2 to about 18 carbon atoms and a combination comprising one aliphatic unsaturation of hydrocarbon radicals, siloxane segments, and a divalent hydrocarbon radical free of aliphatic unsaturation comprising 2 to about 18 carbon atoms.
BACKGROUND OF THE INVENTION
Polyorganosiloxane compositions which cure to elastomeric materials at room temperature are well known. Such compositions can be obtained by mixing polydiorganosiloxanes having reactive or hydrolyzable groups, such as silanol or alkoxy groups, with silane crosslinking agents, for example, alkoxysilanes, acetoxysilanes, oximosilanes, or aminosilanes, and catalysts as needed. Generally, the polydiorganosiloxanes may have 1 to 3 reactive groups per chain end. Compositions comprising these ingredients can then be cured by exposure to atmospheric moisture at room temperature.
The cure rate of a particular composition is dependent on a number of factors including the type of reactive or hydrolyzable group utilized. It is known that different hydrolyzable groups have different reactivities and even the same type of hydrolyzable group can have different reactivities. For example, in the presence of moisture, a silicon-bonded acetoxy group will hydrolyze more rapidly than a silicon-bonded alkoxy group. In addition if, for example, a silicon-bonded trialkoxy group is present on a polymer, it is believed that each silicon-bonded alkoxy group has a different reactivity, with the alkoxy group first reacted being “most reactive.” Generally, once the first alkoxy group reacts it takes a longer time for the second alkoxy group on the same silicon atom to react, and even longer for the third. Therefore, it would be desirable to prepare an organosilicon compound which can endcap a polymer and be capable of providing more than one “most” reactive hydrolyzable group per polymer chain end.
The objective of the present invention is to prepare a cyclic organosilicon compound comprising one aliphatic unsaturation which is capable of endcapping a polymer and providing more than one “most” reactive hydrolyzable group per polymer chain end.
SUMMARY OF THE INVENTION
The present invention is a cyclic organosilicon compound comprising one aliphatic unsaturation described by formula
where each R is an independently selected hydrocarbon radical free from aliphatic unsaturation comprising 1 to about 18 carbon atoms; each X is independently selected from the group consisting of halogen, alkoxy, acyloxy, and ketoximo; m is an integer from 2 to 7; p is an integer from 0 to 6; m+p is an integer from 2 to 8; n is 0, 1, or 2; each Z is independently selected from the group consisting of divalent hydrocarbon radicals free of aliphatic unsaturation comprising about 2 to 18 carbon atoms and a combination of divalent hydrocarbon radicals and siloxane segments; and Y is selected from the group consisting of hydrocarbon radicals comprising one aliphatic unsaturation and 2 to about 18 carbon atoms and a combination comprising one aliphatic unsaturation of hydrocarbon radicals, siloxane segments, and a divalent hydrocarbon radical free of aliphatic unsaturation comprising 2 to about 18 carbon atoms.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is a cyclic organosilicon compound comprising one aliphatic unsaturation described by formula
where each R is an independently selected hydrocarbon radical free from aliphatic unsaturation comprising 1 to about 18 carbon atoms; each X is independently selected from the group consisting of halogen, alkoxy, acyloxy, and ketoximo; m is an integer from 2 to 7; p is an integer from 0 to 6; m+p is an integer from 2 to 8; n is 0, 1, or 2; each Z is independently selected from the group consisting of divalent hydrocarbon radicals free of aliphatic unsaturation comprising about 2 to 18 carbon atoms and a combination of divalent hydrocarbon radicals and siloxane segments described by formula
where R is as defined above; each G is an independently selected divalent hydrocarbon radical free of aliphatic unsaturation comprising about 2 to 18 carbon atoms; and c is a whole number from 1 to about 6; and Y is selected from the group consisting of hydrocarbon radicals comprising one aliphatic unsaturation and 2 to about 18 carbon atoms and a combination comprising one aliphatic unsaturation of hydrocarbon radicals, siloxane segments, and a divalent hydrocarbon radical free of aliphatic unsaturation comprising 2 to about 18 carbon atoms described by formula
where R, G, and c are as defined above and M is an independently selected hydrocarbon radical comprising one aliphatic unsaturation and 2 to about 18 carbon atoms.
In formula (I), each R is an independently selected hydrocarbon radical free from aliphatic unsaturation comprising 1 to about 18 carbon atoms. The hydrocarbon radicals free from aliphatic unsaturation represented by R may be substituted or unsubstituted. Examples of hydrocarbon radicals free from aliphatic unsaturation include alkyl radicals, aryl radicals, and aralkyl radicals. Examples of alkyl radicals include methyl, ethyl, hexyl, octadecyl, cyclobutyl, cyclopentyl, cyclohexyl, 3,3,3-trifluoropropyl, chloromethyl, and chlorocyclopentyl. Examples of aryl radicals include phenyl, tolyl, xylyl, 2,4-dichlorophenyl, and tetrachlorophenyl. Examples of aralkyl radicals include benzyl, beta-phenylethyl, gamma-tolylpropyl, para-chlorobenzyl, and 2-(bromophenyl)propyl. Preferably each R is an independently selected alkyl radical. More preferably each R is an independently selected alkyl radical comprising 1 to about 8 carbon atoms. Most preferably each R is methyl.
In formula (I), each X is independently selected from the group consisting of halogen, alkoxy, acyloxy, and ketoximo. The halogen atoms can be chlorine, bromine, fluorine, and iodine. Examples of alkoxy groups include methoxy, ethoxy, iso-propoxy, butoxy, cyclohexoxy, phenoxy, 2-chloroethoxy, 3,3,3-trifluoropropoxy, 2-methoxyethoxy, and p-methoxyphenoxy. Examples of acyloxy groups include acetoxy, propionoxy, benzoyloxy, and cyclohexoyloxy. Examples of ketoximo groups include dimethylketoximo, methylethylketoximo, methylpropylketoximo, methylbutylketoximo, and diethylketoximo. Preferably each X is independently selected from the group consisting of alkoxy, acyloxy, and ketoximo. More preferably each X is independently selected from the group consisting of alkoxy and acyloxy, with each X being an independently selected alkoxy group being most preferred.
In formula (I), each Z is independently selected from the group consisting of divalent hydrocarbon radicals free of aliphatic unsaturation comprising about 2 to 18 carbon atoms and a combination of divalent hydrocarbon radicals and siloxane segments described by formula
where R is as defined above; each G is an independently selected divalent hydrocarbon radical free of aliphatic unsaturation comprising about 2 to 18 carbon atoms; and c is a whole number from 1 to about 6.
Examples of the divalent hydrocarbon radicals free of aliphatic unsaturation represented by Z and G include alkylene radicals, arylene radicals and aralkylene radicals. The divalent hydrocarbon radicals represented by Z and G may be substituted or unsubstituted. Examples of alkylene radicals include ethylene, methylmethylene, propylene, b

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