Aromatic-based polysiloxane prepolymers and ophthalmic devices produced therefrom
AssigneeBausch & Lomb Incorporated
InventorsYu-Chin Lai, Edmond Quinn
Life of this patent
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Abstract
A polysiloxane comprises diaryl, dialkyl, and arylalkyl siloxane units, and further has at least a functional group. Such polysiloxane can be further copolymerized with an additional monomer to produce polymeric compositions suitable for making ophthalmic devices. The additional monomer can be selected to produce desirable properties for ophthalmic applications, such as high refractive index and/or high elongation.
Claims35
A polysiloxane comprising diaryl siloxane, dialkyl siloxane, and arylalkyl siloxane units, and end capped with functional groups.
A polysiloxane having a formula of
- wherein R1 groups are the same or different and are selected from the group consisting of C1-C10 alkyl and C1-C10 haloalkyl;
- R2 is selected from the group consisting of C1-C10 alkyl and C1-C10 haloalkyl;
- R3 is selected from the group consisting (if C6-C36 aryl, substituted C6-C36 aryl, and aryl groups linked or fused with a heterocyclic group;
- R4 groups are the same or different and are selected from the group consisting of C6-C36 aryl, substituted C6-C36 aryl group, and aryl groups linked or fused with a heterocyclic group;
- R5 is selected from the group consisting of R1 and R4;
- D1 and D2 are the same or different and are selected from the group consisting of direct bonds, saturated and unsaturated straight C1-C10 hydrocarbon divalent groups, saturated and unsaturated branched C3-C10 hydrocarbon divalent groups, cyclic C3-C10 hydrocarbon divalent groups, with or without one or more heteroatoms therein;
- Z is a functional group selected from the group consisting of vinyl, allyl, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, epoxide, isocyanate, isothiocyanate, amino, hydroxyl, alkoxy, mercapto, anhydride, carboxylic, fumaryl, styryl, and combinations thereof;
- and m, n, and p are integers in the range from 1 to, and including, 1000.
A polysiloxane having a formula of
- wherein R1 groups are the same or different and are selected from the group consisting of C1-C10 alkyl and C1-C10 haloalkyl R2 is selected from the group consisting of C1-C10 alkyl and C1-C10 haloalkyl;
- R3 and R4 are independently selected from the group consisting of phenyl, cumenyl, mesityl, tolyl, xylyl, benzyl, benzhydryl, cinnamyl, phenethyl, styryl, trityl, naphthyl, anthryl, phenanthryl, chrysyl, and derivatives thereof;
- R5 is selected from the group consisting of R1 and R4;
- D1 and D2 are the same or different and are selected from the group consisting of direct bonds, saturated and unsaturated straight C1-C10 hydrocarbon divalent groups, saturated and unsaturated branched C3-C10 hydrocarbon divalent groups, cyclic C3-C10 hydrocarbon divalent groups, with or without one or more heteroatoms therein;
- Z is a functional group selected from the group consisting of vinyl, allyl, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, epoxide, isocyanate, isothiocyanate, amino, hydroxyl, anhydride, carboxylic, and combinations thereof;
- m, n, and p are integers in the range from 1 to, and including, 1000;
- and (2p+n)/(2m+n)≧0.25.
A polymeric composition comprising units of diaryl siloxane, dialkyl siloxane, arylalkyl siloxane units, and units of another monomer.
A polymeric composition comprising a copolymer of a polysiloxane prepolymer and another monomer, wherein the polysiloxane prepolymer has a formula of
- wherein R1 groups are the same or different and are selected from the group consisting of C1-C10 alkyl and C1-C10 haloalkyl;
- R2 is selected from the group consisting of C1-C10 alkyl and C1-C10 haloalkyl;
- R3 and R4 are independently selected from the group consisting of phenyl, cumenyl, mesityl, tolyl, xylyl, benzyl, benzhydryl, cinnamyl, phenethyl, styryl, trityl, naphthyl, anthryl, phenanthryl, chrysyl, and derivatives thereof;
- R5 is selected from the group consisting of R1 and R4;
- D1 and D2 are the same or different and are selected from the group consisting of direct bonds, saturated and unsaturated straight C1-C10 hydrocarbon divalent groups, saturated and unsaturated branched C3-C10 hydrocarbon divalent groups, cyclic C3-10 hydrocarbon divalent groups, with or without one or more heteroatoms therein;
- Z is a functional group selected from the group consisting of vinyl, allyl, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, epoxide, isocyanate, isothiocyanate, amino, hydroxyl, anhydride, carboxylic, and combinations thereof;
- m, n, and p are integers in the range from 1 to, and including, 1000;
- and (2p+n)/(2m+n)≧0.25;
- and wherein said another monomer is selected from the group consisting of aromatic monomers, alkyl monomers, hydrophilic monomers, or combinations thereof.
A method for making a polysiloxane prepolymer, the method comprising reacting at least one diarylalkoxy silane, at least one dialkylalkoxy silane, at least one arylalkylalkoxy silane, and at least one siloxane containing a functional group, wherein the polysiloxane prepolymer comprises said diaryl, dialkyl, and arylalkyl groups.
A method for making a siloxane-containing polymeric composition, the method comprising:
- producing a polysiloxane prepolymer by reacting at least one diarylalkoxy si lane, at least one dialkylalkoxy silane, at least one arylalkylalkoxy silane, and at least one siloxane containing a functional group, wherein the polysiloxane prepolymer comprises said diaryl, dialkyl, and arylalkyl groups;
- and
- reacting the polysiloxane prepolymer with an additional monomer at a temperature and for a time sufficient to produce the siloxane-containing polymeric composition.
A method for making an ophthalmic device, the method comprising:
- (a) providing a mixture comprising a functionally-capped polysiloxane prepolymer and a monomer;
- (b) disposing the mixture in a mold cavity, which forms a shape of the ophthalmic device;
- and
- (c) curing the mixture under a condition and for a time sufficient to form the ophthalmic device.
A method for making an ophthalmic device, the method comprising:
- (a) providing a mixture comprising a functionally-capped polysiloxane prepolymer and a monomer;
- (b) casting the mixture under a condition and for a time sufficient to form a solid block;
- and
- (c) shaping the block into the ophthalmic device.
Dependencies are inferred from the claim text.