Method of manufacturing hydrophilic silicone prepolymer

• US 9,056,879 B2
• Filed: 12/18/2012
• Issued: 06/16/2015
• Est. Priority Date: 12/29/2011
• Status: Active Grant

• Current Assignee: Pegavision Corporation (Pegatron Corporation)
• Original Assignee: Pegavision Corporation (Pegatron Corporation)
• Inventors: Li, Heng-Yi, Ting, Wei-Jia, Lai, Yu-Chin, Chang, Han-Yi
• Primary Examiner(s): Gonzalez, Porfirio Nazario
• Assistant Examiner(s): Adzamli, Kofi
• Application Number:
  US13/718,894
• Publication Number:
  US 20130172592A1
• Time in Patent Office: 910 Days
• Field of Search: 556/419
• US Class Current: 1/1
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C07F 7/0879 Hydrosilylation reactions
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/8116 esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
• CPC Class Codes: C08G 77/458 containing polyurethane sequences
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A method for manufacturing a hydrophilic silicone prepolymer is disclosed. The method comprises ring-opening polymerization (ROP) of cyclosiloxanes, hydrosilylation of polysiloxanes, copolymerization, and end-capping reaction. After the above processes, the hydrophilic silicone prepolymer can be obtained.

Claims

1. A hydrophilic silicone prepolymer, wherein a structure of the hydrophilic silicone prepolymer is shown as formula (I):

2. The hydrophilic silicone prepolymer of claim 1, wherein the molecular weight of the hydrophilic silicone prepolymer is less than 20000.

3. The hydrophilic silicone prepolymer of claim 1, wherein the weight percentage of the siloxane units with hydrophilic side chain in the prepolymer is in a range of 5 wt % to 90 wt % of the prepolymer.

4. The hydrophilic silicone prepolymer of claim 1, wherein the hydrophilic silicone prepolymer is comprised in a polymeric material.

5. The hydrophilic silicone prepolymer of claim 1, wherein the hydrophilic silicone prepolymer is comprised in a silicone hydrogel lens.

6. The hydrophilic silicone prepolymer of claim 2, wherein the molecular weight of the hydrophilic silicone prepolymer is in a range of 5000 to 20000.

7. A method for manufacturing a hydrophilic silicone prepolymer, comprising the steps of:

performing a ring-opening polymerization, wherein a cyclic siloxane and a cyclic hydrogen siloxane are catalyzed by a strong acid, and then inserted into a hydroxyl-terminated disiloxane, so as to form a hydroxyl-terminated polysiloxane containing multi silicon-hydrogen (Si—

H) groups;

performing a hydrosilation, wherein a carbon-carbon double bond of a hydrophilic monomer is added to the Si—

H groups of the polysiloxane by a rhodium-based catalyst, and then the hydrophilic monomer is connected to the polysiloxane to form a hydroxyl-terminated silicone diol containing a hydrophilic side-chain, in which the hydrophilic monomer is an amide-containing hydrophilic monomer or a phosphorylcholine-containing hydrophilic monomer;

performing a copolymerization, wherein p mole of the silicone diol produced under the hydrosilation is polymerized with q mole of a diisocyanate in a different molar ratio by a catalyst of dibutyltin dilaurate (DBTDL), so as to form a diol copolymer end-capped with hydroxyl groups as p>

q or form an isocyanate copolymer end-capped with isocyanate groups as p<

q; and

performing a end-capping reaction, wherein the diol copolymer is end-capped with an ethylenically unsaturated monomer containing electrophiles or the isocyanate copolymer is end-capped with an ethylenically unsaturated monomer containing nucleophiles, so as to give the hydrophilic silicone prepolymer end-capped with ethylenically unsaturated groups.

8. The method of claim 7, wherein the cyclic siloxane is octamethylcyclotetrasiloxane (D4), and the cyclic hydrogen siloxane is 1,3,5,7-tetramethylcyclotetrasiloxane (D4h).

9. The method of claim 7, wherein the disiloxane is 1,3-bis[3-(2-hydroxyethoxy)propyl]tetramethyl disiloxane or 1,3-bis[hydroxybutyl]tetramethyl disiloxane.

10. The method of claim 7, wherein the amide-containing hydrophilic monomer is selected from the group of amides comprising N-vinyl pyrrolidone, N-allyl pyrrolidone, N-vinyl-N-methyl acetamide and a combination thereof;

and the phosphorylcholine-containing hydrophilic monomer is 2-methacryloyloxyethyl phosphorylcholine (MPC).

11. The method of claim 7, wherein the rhodium-based catalyst is tris(dibutylsulfide) rhodium trichloride.

12. The method of claim 7, wherein the diisocyanate is isophorne diisocyanate (IPDI), toluene-2,4-diisocyanate, or toluene-2,6-diisocyanate.

13. The method of claim 7, wherein the ethylenically unsaturated monomer containing electrophiles is selected from the group of amides comprising isocyanatoethyl methacrylate, methacryloyl chloride and methacrylic anhydride;

and the ethylenically unsaturated monomer containing nucleophiles is 2-hydroxyethyl methacrylate (HEMA).