Method for manufacturing hydrophilic silicone macromer
A method for manufacturing a hydrophilic silicone macromer is provided. A hydrosilylation between a Si—H bond of a polysiloxane and a C═C bond of a hydrophilic monomer is performed by using a rhodium-containing catalyst to form the polysiloxane having a hydrophilic side chain having an amide group or a phosphoryl choline group. After performing an end-capping reaction, the hydrophilic silicone macromer is formed.
1. A hydrophilic silicone macromer fabricated according to a method for manufacturing a hydrophilic silicone macromer, comprising the steps of:
performing a ring-opening insertion, wherein a cyclic Sloane and a cyclic hydrogen Sloane are subject to a ring-opening reaction, and then are inserted into an asymmetrically end-capped polydialkylsiloxane having a terminal reactive hydrogen to form an asymmetrically end-capped polysiloxane having a silicon-hydrogen (Si—H) bond, in which the terminal reactive hydrogen is derived from a hydroxyl group or an amino group;
performing a hydrosilylation between the Si—H bond of the asymmetrically end-capped polysiloxane and a C═C bond of a hydrophilic monomer by using a rhodium-containing catalyst to form an asymmetrically end-capped polysiloxane intermediate having a hydrophilic side chain, wherein the hydrophilic monomer has an amide group or a phosphoryl choline group; and
performing an end-capping reaction between the terminal reactive hydrogen of the asymmetrically end-capped polysiloxane intermediate and an electrophilic group of an ethylenically unsaturated compound to form the hydrophilic silicone macromer having only one ethylenically unsaturated group.
2. The macromer of claim 1 , wherein the hydrophilic silicone macromer has a structure of chemical formula (1):
wherein
R1 is a C1-C12 alkyl group;
R2 is —(CH2) b -O—(CH2) c - or a C3-C6 alkyl group; b is 2 to 4; c is 2 to 4;
R3 is a hydrogen or a methyl group;
W is
R4 is a C1-C4 alkyl group; R5 is a C1-C2 alkyl group; R6 is a C1-C3 alkyl group;
d is 2 to 4; e is 2 to 4;
L is —COO—, —CONH—, —NHCOO— or —NHCONH—;
Y is —(CH2)f- or —COO(CH2)g-; f is 0 to 4; g is 2 to 4;
p is greater than 4; and q is greater than or equal to 4.
3. The macromer of claim 2 , wherein q/p is in a range of about 0.05 to about 0.9.
4. The macromer of claim 1 , wherein the hydrophilic silicone macromer is comprised in a polymeric material.
5. The macromer of claim 1 , wherein the hydrophilic silicone macromer is comprised in a silicone hydrogel lens.
6. A hydrophilic silicone macromer has a structure of chemical formula (1):
wherein
R1 is a C1-C12 alkyl group;
R2 is —(CH2)b-O—(CH2)c- or a C3-C6 alkyl group; b is 2 to 4; c is 2 to 4;
R3 is a hydrogen or a methyl group;
W is
R4 is a C1-C4 alkyl group; R5 is a C1-C2 alkyl group; R6 is a C1-C3 alkyl group;
d is 2 to 4; e is 2 to 4;
L is —COO—, —CONH—, —NHCOO— or —NHCONH—;
Y is —(CH2)f- or —COO(CH2)g-; f is 0 to 4; g is 2 to 4;
p is greater than 4; and q is greater than or equal to 4.
7. The macromer of claim 6 , wherein the hydrophilic silicone macromer is comprised in a polymeric material.
8. The macromer of claim 6 , wherein the hydrophilic silicone macromer is comprised in a silicone hydrogel lens.