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Hydrophilic macromer and hydrogel comprising said monomer

A macromonomer, hydrogel technology, used in instruments, optical components, optics, etc., to achieve the effect of high oxygen permeability

Active Publication Date: 2019-06-07
MOMENTIVE PERFORMANCE MATERIALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] The state of the art for soft contact lenses (including the silicone based materials described in the above mentioned patents) still has major deficiencies like sub-optimal surface wettability and lipid deposition

Method used

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  • Hydrophilic macromer and hydrogel comprising said monomer
  • Hydrophilic macromer and hydrogel comprising said monomer
  • Hydrophilic macromer and hydrogel comprising said monomer

Examples

Experimental program
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Embodiment 1

[0091] A three-neck reactor equipped with a condenser, temperature probe and addition funnel was charged with 7.55 g of methallyl alcohol-initiated polyether having a hydroxyl content of 1.953 meq / g and 15 ppm (as Pt) in IPA (2 - 5% chloroplatinic acid in propanol). The mixture was heated to 85-90° C. and 5 g of α-dimethylbutylsiloxy-ω-dimethylhydrogensiloxy-terminated polydimethylsilyl with 2.950 meq / g hydride were added dropwise oxane. Once the exotherm ceased, the reaction was continued at 95-100°C for 6 hours, using 1 H and 29Si-NMR confirmed the completion of the reaction. About 30 mL of toluene was added to the material, the reactor was cooled in an ice / water bath and 2.7 g of triethylamine was added. To this cold solution was added dropwise 1.8 g of methacryloyl chloride and the reaction was allowed to continue for about 4 hours, after which time the material was filtered several times to remove any salt produced. The clear solution obtained after filtration was th...

Embodiment 2

[0093] A three-neck reactor equipped with a condenser and temperature probe was charged with 6.7 g of methallyl alcohol-initiated polyether with a hydroxyl content of 1.799 meq / g, 13 g of α-dimethyl butylbutylsiloxy-omega-dimethylhydrogensiloxy terminated polydimethylsiloxane and 75 ppm sodium propionate. The mixture was slowly heated to 95°C and 25 ppm of Pt(0) catalyst was added at 65°C. Once the exotherm ceased, the reaction was continued at 95-100°C for 6 hours, using 1 H and 29 Si-NMR confirmed the completion of the reaction. To this material was added approximately 30 mL of toluene, the reactor was cooled in an ice / water bath and 2.7 g of triethylamine was added. To this cold solution was added dropwise 1.9 g of methacryloyl chloride and the reaction was allowed to continue for about 4 hours, after which time the material was filtered several times to remove any salt produced. The clear solution obtained after filtration was then stirred over 40 g of a basic ion exch...

Embodiment 3

[0095] A three-neck reactor equipped with a condenser and temperature probe was charged with 16.3 g of methallyl alcohol-initiated polyether with a hydroxyl content of 1.953 meq / g, 10 g of di-alpha with 3.680 meq / g hydride, Omega-dimethylhydrogensiloxy terminated polydimethylsiloxane and 75 ppm sodium propionate. The mixture was slowly heated to 95°C and 25 ppm of Pt(0) catalyst was added at 65°C. Once the exotherm ceased, the reaction was continued at 95-100°C for 6 hours, using 1 H and 29 Si-NMR confirmed the completion of the reaction. To this material was added approximately 100 mL of hexane, the reactor was cooled in an ice / water bath and 7.5 g of triethylamine was added. To this cold solution was added dropwise 5 g of methacryloyl chloride and the reaction was allowed to continue for about 4 hours, after which time the material was filtered several times to remove any salt produced. The clear solution obtained after filtration was then stirred on 30 g of basic ion ex...

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Abstract

Compositions comprising at least one hydrophilic silicone macromer suitable for the production of hydrogel polymer films from which biomedical devices, such as contact lenses, can be prepared. In one aspect, the hydrophilic silicone macromer has the formula 1: X-Si(R1)(R2)O-(Si(R3)(R4)O)a-Si(R5)(R6)-Y(1 ) wherein R1, R2, R3, R4, R5 and R6 are independently selected from monovalent straight chain, branched or cyclic groups with 1-50 carbon atoms optionally containing heteroatoms, or I, wherein I is RL‑RP; Y is a free radical polymerization effective hydrophilic group with the general structure: RL‑RP‑Z; RL is derived from a non-differentiable group containing the general structure The hydrosilylation effective terminal olefin linking residue of structuring, subscript n is selected from the integer of 1-10; R7, R8 and R9 can be selected from hydrogen and optionally containing heteroatoms with 1-10 carbon atoms A monovalent hydrocarbon group; Rb is selected from a monovalent hydrocarbon group with 1-6 carbon atoms; RP is a spacer group, which includes a divalent hydrophilic organic group with 0-100 carbon atoms and optionally contains heteroatoms; and X is a radical polymerizable group. The compositions may be polymers and hydrogel films suitable for use in the preparation of contact lenses.

Description

[0001] Cross References to Related Applications [0002] This application claims a U.S. provisional patent entitled "Hydrophilic Silicone Monomers, Process for Preparation Thereof and Thin Films Containing Same," filed March 22, 2012 The benefit of application 61 / 614,222, which is hereby incorporated by reference in its entirety. technical field [0003] The present invention relates to hydrophilic organomodified silicone-containing macromers and polymers prepared therefrom. In one aspect, the invention relates to linear hydrophilic organo-polysiloxane macromers and polymers derived therefrom. The invention also relates to hydrogel compositions and films suitable for the production of biomedical products, including contact lenses. Background technique [0004] Silicone-hydrogel films are used in the preparation of extended-wear soft contact lenses due to their relatively high oxygen permeability, flexibility, comfort, and reduced corneal complications. Conventional hydrog...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08L83/14
CPCC08G77/20C08G77/46C08L83/04C08L83/08C08L2201/10G02B1/043
Inventor A.萨克斯纳M.普坎S.巴特K.M.刘易斯S.乌马帕赛
Owner MOMENTIVE PERFORMANCE MATERIALS INC