Ester-functional polysiloxanes and copolymers made therefrom
View Patent ↗There is described a polysiloxane having the structure: wherein R 1 , R 2 , and R 3 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical, R 4 is independently a direct bond or hydrocarbon radical optionally substituted with oxygen and nitrogen, R 5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group, R 6 is independently a hydroxyl group, an amine group, an acid chloride group, or a sulfonyl halide group, x is from 1 to 300; y is from 0 to 50; and z is from 0 to 50. The polysiloxane is used to make various copolymers and polymer blends. A variety of articles can be made using the polysiloxane described as a polymer blend or copolymer.
1. A method of preparing the polyorganosiloxane having the structure of Formula I:
wherein R 1 , R 2 , and R 3 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical; R 4 is independently a direct bond or hydrocarbon radical optionally substituted with oxygen and nitrogen; R 5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group; R 6 is independently a hydroxyl group; x is from 1 to 300; y is from 0 to 50; and z is from 0 to 50 comprising:
reacting a hydride terminated siloxane represented by Formula II:
wherein R 1 , R 2 and R 3 , are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical; x is from 1 to 300; y is from 0 to 50; and z is from 0 to 50;
with a phenol protected compound having the general formula:
wherein R 4 is independently a direct bond or hydrocarbon radical optionally substituted with oxygen and nitrogen; R 5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group, at a temperature effective to produce a phenol-protected siloxane;
deprotecting the phenol-protected siloxane compound in a mixture of a polar solvent and a mineral acid to form a phenol-deprotected siloxane; and
purifying the phenol-deprotected siloxane.
2. The method of claim 1 , wherein the hydride terminated siloxane with the phenol protected compound is carried out at a temperature of about 80° C. to 200° C.
3. The method of claim 1 , wherein the phenol protected compound is allyl 4-((tetrahydro-2H-pyran-2-yl)oxy)benzoate or allyl 2-(4-((tetrahydro-2H-pyran-2-yl)phenyl acetate.
4. The method of claim 1 , wherein the mixture of polar solvent and mineral acid is tetrahydrofuran and hydrogen chloride.
5. The method of claim 1 , wherein the purifying phenol-deprotected siloxane is achieved by removal of organics.
6. The method of claim 5 , wherein the removal of organics is achieved at reduced pressure and at a temperature of about 150° C. to 300° C.