HYDROPHILIC AND OXYGEN PERMEABLE POLYMER MATERIAL

Abstract

Disclosed is a hydrophilic and oxygen permeable polymer material, including alicyclic Isocyanate, a grafted repeating unit with silicon-containing monomer, and a first hydrophilic moisturing grafted monomer. The grafted repeating unit has an average molecular weight less than or equal 5,000, and is in an amount of 20-60% based on the total weight of the hydrophilic and oxygen permeable polymer material. The first hydrophilic moisturing grafted monomer is in an amount of 1-40% based on the total weight of the hydrophilic and oxygen permeable polymer material.

Claims

1. A hydrophilic and oxygen permeable polymer material having a structure presented by formula A-(B).sub.b-C; wherein A is alicyclic Isocyanate; B is a silicon-containing monomer modified by grafting as a repeating unit; b is an integer of 1-30; (B).sub.b has an average molecular weight less than or equal 5,000, and in an amount of 20-60% based on the total weight of the hydrophilic and oxygen permeable polymer material; C is a first hydrophilic moisturing grafted monomer and in an amount of 1-40% based on the total weight of the hydrophilic and oxygen permeable polymer material; and the first hydrophilic moisturing grafted monomer comprises at least one of Allyl alcohol, 2-Methyl-2-propen-1-ol, 2-Allylethyl alcohol, 2-(Dimethylamino)ethyl methacrylate, 2-(Dimethylamino)ethyl acrylate, 4-Penten-2-ol, N-[3-(Dimethylamino)propyl]methac Rylamide, Hydroxypropyl methacrylate, Poly(propylene glycol) methacrylate, 3-Methyl-2-buten-1-ol, rans,trans-2,4-Hexadien-1-ol, 2-Hydroxypropyl methacrylamide, Poly(ethylene glycol) methacrylate, PLA methacrylate, and Poly(ethylene glycol) methacrylate.

2. The hydrophilic and oxygen permeable polymer material as claimed in claim 1, wherein the alicyclic Isocyanate comprises 3-Isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (IPDI) represented by a formula as: ##STR00045##

3. The hydrophilic and oxygen permeable polymer material as claimed in claim 1, wherein the silicon-containing monomer comprises at least one of 3-methacryloxypropyl tris(trimethylsiloxy)silane, 3-acryloxypropyl tris(trimethylsiloxy)silane, 3-acrylamidopropyl tris(trimethylsiloxy)silane, 3-methacrylamidopropyl tris(trimethylsiloxy)silane, 3-vinyl carbamatepropyl tris(trimethylsiloxy)silane, and (3-methacryloxy-2-hydroxyprpoxy) propylbis (trimethylsiloxy)methylsilane.

4. The hydrophilic and oxygen permeable polymer material as claimed in claim 1, further comprising a second hydrophilic moisturing grafted monomer, and the second hydrophilic moisturing grafted monomer comprising at least one of Allyl alcohol, 2-Methyl-2-propen-1-ol, 2-Allylethyl alcohol, 2-(Dimethylamino)ethyl methacrylate, 2-(Dimethylamino)ethyl acrylate, 4-Penten-2-ol. N[3-(Dimethylamino)propyl]methacrylamide, Hydroxypropyl methacrylate, Poly(propylene glycol) methacrylate, 3-Methyl-2-buten-1-ol, trans,trans-2,4-Hexadien-1-ol, N-3-Sulfopropyl-N,N-dimethyl ammonium)ethyl methacrylate, N,N-Dimethylacrylamide, Poly(ethylene glycol) methacrylate, 2-Hydroxypropyl methacrylamide, Poly(ethylene glycol) methacrylate, (Methacryloyloxy)ethyl]dimethylammoniol]propionate, 2-Hydroxyethyl methacrylate, PLA methacrylate, Phosphobetaine methacrylate, and Poly(ethylene glycol) methacrylate.

5. The hydrophilic and oxygen permeable polymer material as claimed in claim 1, wherein (B).sub.b is polydimethylsiloxane.

Description

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT

[0009] The present invention may be embodied in various forms and the details of the preferred embodiments of the present invention will be described in the subsequent content with reference to the accompanying drawings. The drawings (not to scale) show and depict only the preferred embodiments of the invention and shall not be considered as limitations to the scope of the present invention. Modifications of the shape of the present invention shall too be considered to be within the spirit of the present invention.

[0010] The hydrophilic and oxygen permeable polymer material according to the embodiment of the present invention has a structure presented by formula A-(B).sub.b-C, wherein A is alicyclic Isocyanate, B is a silicon-containing monomer modified by grafting as a repeating unit, b is an integer of 1-30, and , C is a first hydrophilic moisturing grafted monomer.

[0011] Specifically, (B).sub.b is preferably polydimethylsiloxane and has an average molecular weight less than or equal 5,000, and is in an amount of 20-60% based on the total weight of the hydrophilic and oxygen permeable polymer material. Further, the first hydrophilic moisturing grafted monomer is in an amount of 1-40% based on the total weight of the hydrophilic and oxygen permeable polymer material.

[0012] It is preferred that the first hydrophilic moisturing grafted monomer comprises at least one of Allyl alcohol, 2-Methyl-2-propen-1-ol, 2-Allylethyl alcohol, 2-(Dimethylamino)ethyl methacrylate, 2-(Dimethylamino)ethyl acrylate, 4-Penten-2-ol, N-[3-(Dimethylamino)propyl]methac Rylamide, Hydroxypropyl methacrylate, Poly(propylene glycol) methacrylate, 3-Methyl-2-buten-1-ol, rans,trans-2,4-Hexadien-1-ol, 2-Hydroxypropyl methacrylamide, Poly(ethylene glycol) methacrylate, PLA methacrylate, and Poly(ethylene glycol) methacrylate.

[0013] Furthermore, the chemical formula for the above first hydrophilic moisturing grafted monomer is summarized in Table 1.

TABLE-US-00001 TABLE 1 Allyl alcohol [00001] 2-Methyl-2-propen-1-ol [00002] 2-Allylethyl alcohol [00003] 3-Methyl-2-buten-1-ol [00004] trans,trans-2,4-Hexadien-1-ol [00005] 2-(Dimethylamino)ethyl methacrylate [00006] 2-(Dimethylamino) ethyl acrylate [00007] 4-Penten-2-ol [00008] 2-Hydroxypropyl methacrylamide [00009] Poly(ethylene glycol) methacrylate [00010] (Dimethylamino)propyl] methacrylamide [00011] Hydroxypropyl methacrylate [00012] Poly(propylene glycol) methacrylate [00013] PLA methacrylate [00014] Poly(ethylene glycol) methacrylate(PEGMA) [00015]

[0014] More specifically, the silicon-containing monomer comprises at least one of 3-methacryloxypropyl tris(trimethylsiloxy)silane, 3-acryloxypropyl tris(trimethylsiloxy)silane, 3-acrylamidopropyl tris(trimethylsiloxy)silane, 3-methacrylamidopropyl tris(trimethylsiloxy)silane, 3-vinyl carbamatepropyl tris(trimethylsiloxy)silane, and (3-methacryloxy-2-hydroxyprpoxy) propylbis (trimethylsiloxy)methylsilane.

[0015] The above silicon-containing monomer is further clearly expressed at Table 2 below.

TABLE-US-00002 TABLE 2 3-(Trimethoxysilyl)propylmethacrylate H.sub.2CC(CH.sub.3)CO.sub.2(CH.sub.2).sub.3Si(OCH.sub.3).sub.3) [00016] 3-(Trimethoxysilyl)propyl acrylate H.sub.2CCHCO.sub.2(CH.sub.2).sub.3Si(OCH.sub.3).sub.3) [00017] lamidopropyl tris(trimethylsiloxy)silane C15H37NO4Si4 [00018] 3-Methacrylamidopropyl tris(trimethylsiloxy)silane C.sub.16H.sub.39NO.sub.4Si.sub.4) [00019] 3-Methacryloxypropylmethyl dimethoxysilane C.sub.10H.sub.20O.sub.4Si [00020] Triethoxyvinylsilane H.sub.2CCHSi(OC.sub.2H.sub.5).sub.3) [00021]

[0016] Preferably, the alicyclic isocyanate comprises 3-Isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (IPDI), which is represented by a formula:

##STR00022##

[0017] Specifically, IPDI has lower reactivity and vapor pressure than aromatic isocyanate, and includes two NCO groups, which have different chemical activity. The NCO group on the cyclohexane ring has stronger reactivity by 1.3-2.5 times than the other NCO group bonded with a methyl group, which suffers from retardation due to the cyclohexane ring and the methyl group. As a result, IPDI has the reaction rate with the hydroxyl group faster than HDI by 4-5 times.

[0018] The polyurethane resin made from IPDI demonstrates excellent optical stability and chemical endurance, and is suitably applied to high end polyurethane coating with optical and weather endurance, and elastomer with abrasion and hydrolysis endurance.

[0019] In addition, the hydrophilic and oxygen permeable polymer material further comprises a second hydrophilic moisturing grafted monomer, and the second hydrophilic moisturing grafted monomer preferably comprises at least one of Allyl alcohol, 2-Methyl-2-propen-1-ol, 2-Allylethyl alcohol, 2-(Dimethylamino)ethyl methacrylate, 2-(Dimethylamino)ethyl acrylate, 4-Penten-2-ol. N-[3-(Dimethylamino)propyl]methac rylamide, Hydroxypropyl methacrylate, Poly(propylene glycol) methacrylate, 3-Methyl-2-buten-1-ol, trans,trans-2,4-Hexadien-1-ol, N-3-Sulfopropyl-N,N-dimethyl ammonium)ethyl methacrylate, N,N-Dimethylacrylamide, Poly(ethylene glycol) methacrylate, 2-Hydroxypropyl methacrylamide, Poly(ethylene glycol) methacrylate, (Methacryloyloxy)ethyl]dimethylammoniolpropionate, 2-Hydroxyethyl methacrylate, PLA methacrylate, Phosphobetaine methacrylate, and Poly(ethylene glycol) methacrylate.

[0020] Furthermore, the chemical formula for the above first hydrophilic moisturing grafted monomer is summarized in Table 3.

TABLE-US-00003 TABLE 3 Allyl alcohol [00023] 2-Methyl-2-propen-1-ol [00024] 2-Allylethyl alcohol [00025] 3-Methyl-2-buten-1-ol [00026] trans,trans-2,4-Hexadien- 1-ol [00027] -3-Sulfopropyl-N,N-dimethyl ammonium)ethyl methacrylate, (SBMA) [00028] N,N-Dimethylacrylamide [00029] Poly(ethylene glycol) methacrylate [00030] 2-(Dimethylamino)ethyl methacrylate [00031] 2-(Dimethylamino)ethyl acrylate [00032] 4-Penten-2-ol [00033] 2-Hydroxypropyl methacrylamide [00034] Poly(ethylene glycol) methacrylate [00035] Methacryloyloxy)ethyl] dimethylammonio]propionate (CBMA) [00036] 2-Hydroxyethyl methacrylate [00037] (Dimethylamino)propyl] methacrylamide [00038] Hydroxypropyl methacrylate [00039] Hydroxypropyl methacrylate [00040] PLA methacrylate [00041] Phosphobetaine methacrylate (PBMA) [00042] Poly(ethylene glycol) methacrylate(PEGMA) [00043] Polyvinylpyrrolidone cross- linked [00044]

[0021] From the above mention, one aspect of the present invention is that the polymer material is highly hydrophilic and oxygen permeable, and furthermore, optical stability and chemical endurance are enhanced by IPDI, particularly, weather, abrasion and hydrolysis endurance. As a result, the polymer material of the present invention is suitably applied to high end polyurethane coating and elastomer.

[0022] Another aspect of the present invention is that when SBMA and CBMA listed at table 2 are processed by the second hydrophilic grafting, SBMA and CBMA as zwitterionic monomers can self-combine and self-assemble with balanced and charged material. For example, hyaluronic acid (HA) with negative electricity are easily aligned on the surface of the contact lens to increase the effect of moisturing and wetness.

[0023] Although the present invention has been described with reference to the preferred embodiments, it will be understood that the invention is not limited to the details described thereof. Various substitutions and modifications have been suggested in the foregoing description, and others will occur to those of ordinary skill in the art. Therefore, all such substitutions and modifications are intended to be embraced within the scope of the invention as defined in the appended claims.