Preparation of polyhedral oligomeric silsesquioxane silanols and siloxides functionalized with olefinic groups
AssigneeHybrid Plastics, Inc.
InventorsJoseph J. Schwab, Yi-Zhong An, Sukhendu B. Hait, William A. Reinerth, Sr., Hendrikus C. L. Abbenhuis
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Abstract
A synthetic process for polyhedral oligomeric silsesquioxanes (POSS) and polyhedral oligomeric silicates (POS) produces silanol and siloxide molecules containing both olefinic groups and alkyl or aromatic groups. Olefin-bearing POSS silanol/siloxides are derivatized into a variety of chemical species while retaining the ability to further derivatize the silanol/siloxide.
Claims10
A method for derivatizing olefinic functionalized polyhedral oligomeric silsesquioxane (POSS) or polyhedral oligomeric silicate (POS) silanol or siloxide molecules comprising the steps of:
- (a) reacting a silane coupling agent of the formula R2SiX3 in the presence of a hydroxide base to form POSS or POS silanol or siloxide molecules, wherein the R2 group contains an olefin group and X is selected from the group consisting of OH, ONa, OLi, OK, OCs, Cl, Br, I, alkoxide (OR), formate (OCH), acetate (OCOR), acid (OCOH), ester (OCOR), peroxide (OOR), amine (NR2), isocyanate (NCO), and R3, where R and R3 are the same or different and each represents an organic substituent group selected from the group consisting of H, siloxy, and aliphatic and aromatic groups that may contain additional reactive functionalities;
- (b) reacting a silane coupling agent of the formula R1SiX3 with the POSS or POS silanol or siloxide molecules in the presence of a hydroxide base, wherein the R1 group contains an alkyl or aromatic group, and wherein said POSS or POS silanol or siloxide molecules contain both R1 and R2;
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- (c) chemical derivatization of R2, wherein the derivatization is selected from the group consisting of oxidation, addition, and metathesis reactions, while preserving the R1 and silanol or siloxide functionality.
A method for modifying olefinic functionalized polyhedral oligomeric silsesquioxane (POSS) or polyhedral oligomeric silicate (POS) silanol or siloxide molecules comprising the steps of:
- (a) reacting a silane coupling agent of the formula R2SiX3 in the presence of a hydroxide base to form POSS or POS silanol or siloxide molecules, wherein the R2 group contains an olefin group and X is selected from the group consisting of OH, ONa, OLi, OK, OCs, Cl, Br, I, alkoxide (OR), formate (OCH), acetate (OCOR), acid (OCOH), ester (OCOR), peroxide (OOR), amine (NR2), isocyanate (NCO), and R3, where R and R3 are the same or different and each represents an organic substituent group selected from the group consisting of H, siloxy, and aliphatic and aromatic groups that may contain additional reactive functionalities;
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- (b) modification of the POSS or POS silanol or siloxide groups by a reaction selected from the group consisting of silation, reaction with a metal, or reaction with a surface.
A method for modifying olefinic functionalized polyhedral oligomeric silsesquioxane (POSS) or polyhedral oligomeric silicate (POS) silanol or siloxide molecules comprising the steps of:
- (a) reacting a silane coupling agent of the formula R2SiX3 in the presence of a hydroxide base to form POSS or POS silanol or siloxide molecules, wherein the R2 group contains an olefin group and X is selected from the group consisting of OH, ONa, OLi, OK, OCs, Cl, Br, I, alkoxide (OR), formate (OCH), acetate (OCOR), acid (OCOH), ester (OCOR), peroxide (OOR), amine (NR2), isocyanate (NCO), and R3, where R and R3 are the same or different and each represents an organic substituent group selected from the group consisting of H, siloxy, and aliphatic and aromatic groups that may contain additional reactive functionalities;
- (b) reacting a silane coupling agent of the formula R1SiX3 in the presence of a hydroxide base to form POSS or POS silanol or siloxide molecules, wherein the R1 group contains an alkyl or aromatic group, and wherein said POSS or POS silanol or siloxide molecules contain both R1 and R2;
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- (c) modification of the POSS or POS silanol or siloxide groups by a reaction selected from the group consisting of silation, reaction with a metal, or reaction with a surface.
A method for preparing olefinic functionalized polyhedral oligomeric silsesquioxane (POSS) or polyhedral oligomeric silicate (POS) silanol or siloxide molecules comprising reacting a plurality of silane coupling agents of the formula R2SiX3 in the presence of a hydroxide base to form POSS or POS silanol or siloxide molecules, wherein a plurality of R2 groups each containing an olefin group, are reacted to prepare POSS or POS silanol or siloxide molecules functionalized with different olefins, and X is selected from the group consisting of OH, ONa, OLi, OK, OCs, Cl, Br, I, alkoxide (OR), formate (OCH), acetate (OCOR), acid (OCOH), ester (OCOR), peroxide (OOR), amine (NR2), isocyanate (NCO), and R3, where R and R3 are the same or different and each represents an organic substituent group selected from the group consisting of H, siloxy, and aliphatic and aromatic groups that may contain additional reactive functionalities.
Dependencies are inferred from the claim text.