JPS60130714A - Material for contact lens - Google Patents

Abstract

PURPOSE:To provide superior oxygen permeability, suitability to wetting with water and water nonretentivity and to enable continuous wear by using a copoly mer consisting of a specified silicon compound, an ester produced from a polyhydric alcohol and methacrylic acid, an ester produced from a monohydric alcohol and methacrylic acid, and a hydrophilic monomer. CONSTITUTION:A copolymer as a material for a contact lens is prepd. by copolymerizing about 40-55pts.wt. methacryloxypropyltris(trimethylsiloxy)silane ( I ) represented by the formula with about 5-35pts.wt. ester (II) produced from 2- 8C polyhydric alcohol and methacrylic acid, about 20-35pts.wt. ester (III) produced from 1-10C monohydric alcohol and methacrylic acid, and about 1- 10pts.wt. hydrophilic monomer (IV) contg. essentially methacrylic acid or acrylic acid. Ethylene glycol dimethacrylate or the like is used as the component II, and methyl methacrylate or the like as the component III. When the copolymer is used, a contact lens having moderate hardness, a desired refractive index and a reduced thickness is obtd. The lens has high oxygen permeability and suitability to wetting with water and enables long-time continuous wear.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a contact lens material, particularly a contact lens material that has excellent oxygen permeability and water leakage properties, can be worn continuously for a long period of time, and is substantially water-free. This invention relates to a contact lens that is easy to handle. [Prior Art and Problems] Conventionally, contact lenses whose main component is, for example, polymethyl methacrylate have been put into practical use. Polymethyl methacrylate, which is the main component of contact lenses, has great advantages such as excellent optical properties and durability, but the wearability is not so good because the contact lens surface does not have good resistance to wood. Furthermore, it has a fatal drawback that it cannot be worn continuously for a long time due to corneal physiology because of poor oxygen permeability.

Therefore, as a solution to the above-mentioned drawbacks of hard type contact lenses, water-containing contact lenses containing poly-2-hydroxyethyl methacrylate as a main component have been put into practical use, and soft type contact lenses such as these have been put into practical use. Although the lenses have good water resistance and are comfortable to wear, they do not have sufficient oxygen permeability, so they cannot be worn continuously for long periods of time, and they are water-retaining, making them difficult to handle. be.

Contact lenses made from silicone resin have been proposed as contact lenses that exceed the above-mentioned contact lenses whose main ingredients are polymethyl methacrylate or poly 2-hydroxyethyl methacrylate. A contact lens made of a modified silicone resin has been proposed, and has been put into practical use in some cases. However, it is not 100% satisfactory in terms of comfort and long-term continuous wear.

[Disclosure of the invention]

The present inventor has discovered that the oxygen permeability of silicone resin contact lenses is greatly affected by the amount of alkylsiloxane bonds contained in the material, and that when the oxygen permeability is increased by increasing the alkylsiloxane bonds, the wettability decreases. We focused on methacryloxy-7propyltris(trimethylsiloxy)silane and silane with a carbon number of 2 to B.
A polymer copolymerized using at least an ester of a polyhydric alcohol and methacrylic acid, an ester of a monohydric alcohol having 1 to 10 carbon atoms and methacrylic acid, and a hydrophilic monomer has oxygen permeability. They have also found that they have excellent wettability, good hardness, and excellent dimensional stability. CH.

The proportions of methacryloxyglopyltris(trimethylsiloxy) silane represented by Product 3, ester of polyhydric alcohol and methacrylic acid, ester of monohydric alcohol and methacrylic acid, and hydrophilic monomer are as follows: 40-55
: 5 to 35 : 20 to 35 : Desirably within the range of 1 to 1 O, and these proportions are copolymerized using a suitable free radical polymerization initiator, for example, 3 weight or less. The contact lens material of the present invention is thereby obtained.

Examples of esters of polyhydric alcohol and methacrylic acid include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, 1,3-butanediol dimethacrylate, and 1,4-butane. Diol dimethacrylate, 1.
It is desirable to use 6-hexanethiol dimethacrylate, neopentyl glycol dimethacrylate, tetrapentaerythritol tetramethacrylate, trimethylolpropane trimethacrylate, and the like.

Examples of esters of monohydric alcohol and methacrylic acid include methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, 1so-propyl methacrylate, n-butyl methacrylate, 1so-butyl methacrylate, tert-butyl methacrylate, pentyl methacrylate, neo It is desirable to use pentyl methacrylate, hexyl methacrylate, cyclohexyl methacrylate, 2-ethylhexyl methacrylate, and the like.

Further, as the hydrophilic monomer for imparting hydrophilicity to the surface of the contact lens, it is desirable to use, for example, methacrylic acid, acrylic acid, or the like.

Furthermore, since the polymerization of the above monomers is carried out, for example, by radical polymerization, for example, dimethyl-2
, 2'-azobisisobutyrate, 2,2-azobis(
4-methquin-2,4-dimethylvaleronitrile), 2
．． 2'-azobis(2,4-dimethylvaleronitrile)
, 2'-azobisinbutylnitrile, benzoyl peroxide, di-tert-butyl peroxide,
It is desirable to use methyl ethyl ketone peroxide, imbutyryl peroxide, diimpropyl peroxydicarbonate, and the like.

Then, by polymerizing the above-mentioned material into a suitable block and subjecting it to ordinary mechanical processing, a contact lens can be obtained.

[Examples 1 to 10] Methacryloxyglopyltris (trimethylsiloxy)
Silane (hereinafter abbreviated as TRl5) 40 parts by weight, cyclohexyl methacrylate (hereinafter abbreviated as C-HMA) 24
．． 5 parts by weight of V-65 (trade name, , 2'-azobis(2,4-dimethylvaleronitrile)) was added and poured into a cylindrical polypropylene polymerization mold with a diameter of 16 cm and a height of 10 m, and the upper space was After purging with nitrogen, it was kept at 40°C for 20 hours in an open air purged with nitrogen, then held at 70°C and 90°C for 10 hours each, and then held at 100°C for 10 hours to complete the polymerization, resulting in a colorless product. Obtain a transparent hard rod-shaped block.

Finally, it undergoes normal processing and is made into contact lenses.

The characteristics of the contact lenses thus obtained are shown in Table 1. Table 1 EDMA: Ethylene glycol dimethacrylate DE
DMA diethylene glycol dimethacrylate TED
MA: ) IJ ethylene glycol dimethacrylate 4EDMA: tetraethylene glycol dimethacrylate 1.3BDMA: 1.3-butanediol dimethacrylate 1.4BDMA: 1,4-butanediol dimethacrylate 1,6HDMA: 1,6- Hexanethiol dimethacrylate NPDMA: Neopentyl glycol dimethacrylate PR4MA: Pentaerythritol tetramethacrylate TMTMA: ) Rimethylolpropane trimethacrylate rll elementary permeability coefficient unit t
;t-10-”cc (STP)cm/cIi・SS
eC-1111H [Examples 11 to 19] 40 parts by weight of TI (I8), 26.5 parts by weight of TEDMA, 8.0 parts by weight of acrylic acid (hereinafter abbreviated as AA), monohydric alcohol and methacrylic acid shown in Table 2 Esther 2
1 part by weight of a polymerization initiator of V-601 (trade name: dimethyl-2,2'-azobisisobutyrate) was added to 4.5 parts by weight of the mixture, and polymerization was carried out in the same manner as in Example 1. A colorless, transparent, hard rod-shaped block was obtained, which was then subjected to conventional processing to obtain contact lenses.

The characteristics of the contact lenses thus obtained are shown in Table 2.

Table '2 MMA: Methyl methacrylate HMA: Ethyl methacrylate i-PMA: Isoglobil methacrylate n-BMA:
n-butyl methacrylate 1-DMA: inbutyl methacrylate t-BMA: tert-butyl methacrylate rl-HMA: n-hexyl methacrylate 2-E
HMA: 2-ethylhexyl methacrylate The unit of oxygen permeability i is 10"cc (STP) cm/cIl-
sec-frame Hg [Examples 20 to 25] TRl 840 to 55 parts by weight, EDM & 8 to 32 parts by weight,
MMA 24-33 parts by weight, AA 4 parts by weight, -650.
A colorless, transparent, hard rod-shaped block was obtained in the same manner as in Example 1 using 01 parts by weight, and this was processed to obtain a contact lens.

The properties of the contact lenses obtained in this way are as shown in Table 3.0 Table 3 The unit of oxygen permeability coefficient is 10-”cc (ST, P)
crtt/cri 5ec-TsuruHg [Examples 26-32] TRl 840-48 parts by weight, TEDMA 12.5-28
．． 5 parts by weight, EDMA 14 parts by weight or less, MMA 4-14
．． 5 parts by weight, C-HMA 12-25 parts by weight, MA7.5
A colorless, transparent, hard rod-shaped block was obtained in the same manner as in Example 1 using ~9 parts by weight and 1 part by weight of V-650.0, and this was processed to obtain a contact lens.

The characteristics of the contact lens obtained in this way were investigated and found to be 9 as shown in Table 4.

Table 4 The unit of oxygen permeability coefficient is 10-”cc (8TP) crn
/dt-sec -HHg [Effect] The hydrophilic contact angle is small, so it has good water wettability.
Further, a contact lens having a large oxygen permeability coefficient and which can be worn continuously for a long period of time can be obtained.

Furthermore, since a substantially water-free and strong hard contact lens can be obtained, it is easy to handle and is less likely to be damaged.

In addition, since it has appropriate hardness when processed into contact lenses, it is easy to process, and the manufacturing cost of contact lenses is low.

Moreover, since it has a desirable refractive index, the thickness of the contact lens can be relatively thin, and a contact lens with improved wearability can be obtained.

Agent Katsu Udaka: Self.

゛・1. 6.7 '92 Procedural amendment (voluntary) June 1981 Hiroguchi Commissioner of the Patent Office ■Indication of incident Patent application No. 58-237871) Second brother Akira's name contact lens materials 3. Person who makes corrections Relationship to the incident: Patent applicant Nippon Kontata Torens Manufacturing Co., Ltd. 4. Agent The claims are amended as follows.

■ Methacryloxypropyltris(trimethylsiloxy)silane represented by CH3 I CH3, an ester of a polyhydric alcohol having 2 to 8 carbon atoms and methacrylic acid, and an ester of a monohydric alcohol having 1 to 10 carbon atoms and methacrylic acid. and a hydrophilic monomer containing a small amount of methacrylic acid or acrylic acid.

■ In the contact lens material according to claim 1, 40 to 55 parts by weight of methacryloxypropyltris(trimethylsiloxy)silane, 5 to 35 parts by weight of ester of polyhydric alcohol and methacrylic acid, and monohydric alcohol. and methacrylic acid in a ratio of 20 to 35 parts by weight and a hydrophilic monomer in a ratio of 1 to 10 parts by weight.

■ In the contact lens material according to claim 81 or 2, the ester of Tasen 1 alcohol and methacrylic acid is ethylene glycol dimethacrylate,
Diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, 1,3-butanediol dimethacrylate, 1,4-butanediol dimethacrylate-1
-, 1°6-hexa/diol dimethacrylate, neopentyl glycol dimethacrylate, pentaerythritol tetramethacrylate, ]-rimethylolpropane trimethacrylate, or a mixture thereof.

■ In the contact lens material according to claim 1 or 2, the ester of monohydric alcohol and methacrylic acid is methyl methacrylate-1. -Propyl methacrylate, n-butyl methacrylate, 1S
0-butyl methacrylate, tert-butyl methacrylate, pentyl methacrylate, neopentyl methacrylate, hexyl methacrylate, /chlorohexyl methacrylate, 2-ethylhexyl methacrylate, or a mixture thereof.

Claims (1)

[Claims] ■ CH. methacryloxypropyltris(trimethylsiloxy)silane represented by A contact lens material characterized by being copolymerized using at least a monomer. ■ In the contact lens material according to claim 1, 40 to 55 parts by weight of methacryloxypropyltris(trimethyl70xy)silane, 5 to 35 parts by weight of ester of polyhydric alcohol and methacrylic acid, and monovalent The proportion of the ester of alcohol and methacrylic acid is 20 to 35 parts by weight, and the proportion of the hydrophilic monomer is 1 to 10 parts by weight. ■ In the contact lens material according to claim 1 or 2, the ester of polyhydric alcohol and methacrylic acid is ethylene glycol dimethacrylate,
Diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, 1,3-butanediol dimethacrylate, l,4-butanediol dimethacrylate,
1,6-hexa/diol dimethacrylate, neopentyl glycol dimethacrylate, pentaerythritol tetramethacrylate, trimethylolpropane trimethacrylate, or a mixture thereof. ■ In the contact lens material according to claim 1 or 2, the ester of monohydric alcohol and methacrylic acid is methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, 1so-propyl methacrylate, n -butyl methacrylate, 1so
-butyl methacrylate, tert-butyl methacrylate, pentyl methacrylate, neopentyl methacrylate, hexyl methacrylate, cyclohexyl methacrylate, 2-ethylhexyl methacrylate or mixtures thereof. ■ In the contact lens material according to claim 1 or 2, the hydrophilic monomer is methacrylic acid,
Acrylic acid or mixtures thereof.