JPS62200321A - Contact lens - Google Patents

Abstract

PURPOSE:To improve resistance to contamination and permeability for oxygen of a contact lens and to lessen its unrecoverable deformability by using a specified siloxanyl methacrylate polymer, or a copolymer thereof with other vinyl monomer. CONSTITUTION:Polymer of siloxanyl methacrylate expressed by the formula, or copolymers thereof with other vinyl monomer is subjected to molding, and the product, as it is or after low temp. plasma treatment, is used for a material of a contact lens. In the formula, R<1> is H or methyl; Rr is 1-4C F-substituted alkyl; l is 1-4; m is 0, 1, or 2; n is 1-3. Further, (meth)acrylic acid or derivs. thereof is preferred as vinyl monomer to be copolymerized therewith. When this material is used, a contact lens having high resistance to contamination and permeability for oxygen, having reduced unrecoverable deformation is obtd.

Description

[Detailed Description of the Invention] (Field of Industrial Application) The present invention is a contact lens, and the second feature is that when used as a contact lens, it has excellent stain resistance and non-recoverable deformation, and has good oxygen permeability. A certain contact lens C:
It is related to

(Prior art) Eight-doped contact lenses C intended for continuous wear: Various types of contact lenses have recently been developed, but most of these are made from a combination of siloxanyl methacrylate and methacrylate. It is considered to be a polymer (Japanese Patent Application Laid-open No. 50-871)
(See Japanese Patent Application Laid-Open No. 54-55455). However, none of these have sufficient oxygen permeability to supply the cornea with all the oxygen it needs through the lens.
Furthermore, there is a problem with continuous adhesion due to the large amount of dirt that adheres during use.

For this reason, a hard contact lens was developed that is made from a copolymer of polyfluoroalkyl (meth)acrylate and other vinyl monomers with improved oxygen permeability and stain resistance (Unexamined Japanese Patent Publication No. 1986-21141
Refer to Publication No. 9, but if this lens is tried to have sufficient oxygen permeability and stain resistance, the hardness will be weakened and workability will deteriorate, and furthermore, the curvature of the lens will deform during long-term use. has a fatal drawback of large non-recoverable deformability.

(Structure of the Invention) The present invention relates to a contact lens which solves such disadvantages, and which has a general formula: Substituted alkyl group, j is an integer of 1 to 4, m
is 0.1 or ? , n is an integer of 1 to 3] or a copolymer with other vinyl monomers.

That is, as a result of various studies on the development of contact lenses that are oxygen permeable, non-recoverable deformable (varnish free), and also have good oxygen permeability, the present inventors found that the siloxitin group of the conventionally known siloxanyltutaglylate A siloxanyl methacrylate polymer or copolymer in which the alkyl group is a fluorine-substituted alkyl group is used as a material, and if this is formed into a material, it has high oxygen permeability and stain resistance, and is non-recoverable. The present invention was completed by discovering that it is possible to obtain a contact lens that is not deformable and therefore has a stable lens curvature with desirable hardness and good workability.

Siloxanyltutaglylate, which is the material for forming the contact lenses of the present invention, is represented by the general formula %, where R is a hydrogen atom or a methyl group, and R4 is OF3.
, O! F, ,O,H,F, ,O,F,,04 F@
A fluorine-substituted alkyl group having 1 to 4 carbon atoms, such as! is 1~
m is an integer of 4, m is Oll or 2% n is an integer of 1 to 3, and examples thereof include the following.

OOH, OH.

OOHOH.

0 0H, OH.

The siloxanyl methacrylate represented by this formula (1) is obtained by, for example, reacting a fluoroalkyl group-containing organosilochitin with a Grignard reagent to produce a Grignard reaction intermediate, and then reacting this with C dihalogenated organosilyl organometaacrylate. This polymerization can be carried out at a temperature of 50 to 150° C. in the presence of a polymerization catalyst such as azobisisobutyronitrile.

t+, this siloquitinyl methoxide polymer has the above formula [
It may be a copolymer of siloxanyl methacrylate shown in 1) and a l/vinyl monomer, and examples of the vinyl monomer include styrene, butadiene, vinylpyrrolidone, etc. is acrylic acid, methacrylic acid or derivatives thereof such as butyl acrylate, methacrylic acid, methyl methacrylate, 2-hydroxyethyl methacrylate, tris(trimethylsiloxyV]silylpropyl methacrylate, (di)ethylene glycol dimethacrylate, etc. Preferably, this copolymerization is carried out using a conventionally known vinyl copolymerization method, for example, at 50 to 150°C in the presence of a polymerization catalyst such as azobisisobutyronitrile.
Copolymerization may be carried out at a concentration of .

This siloxanyl methacrylate polymer or copolymer is then molded into a contact lens material, but this molding can be done by a conventionally known method; C: Place the 7-year-old pieces in a suitable container and perform bulk polymerization in the container C: Therefore, either form them into round rods or blocks, or dissolve them in a suitable solvent such as toluene or xylene and then place them in a mold. After casting to form a plate-shaped body, cutting,
The contact lens material obtained in this way may be used as a contact lens as it is by mechanical processing such as polishing, but if necessary, low-temperature plasma treatment may be applied to the lens surface. It may be made hydrophilic.

Next, C: Examples of the present invention will be given, where parts in the examples indicate parts by weight.

Example 1 Metallic magnesium 24.3.9 (1 mol) and tetrahydrofuran 300+7 were charged into a reactor, methyl chloride was blown into the reactor to prepare a tetrahydrofuran solution of methylmagnesilam cumylide, and then the mixture was heated under reflux. A solution of 156 g of trifluoropropylmethylsiloxane trimer dissolved in 200 g of tetrahydrofuran was added dropwise over 2 hours to react, and after refluxing for another 2 hours, the reaction solution was Diglolomethylsilylpropyl methacrylate (121.lil) represented by the formula was added dropwise under reflux to react, then poured into 1/2 water, and the organic layer separated from this was distilled under reduced pressure. However, bis(dimethyltrifluoropropylsiloxy)methylsilylpropyl methacrylate shown by the formula is 7
Obtained with a yield of 0%.

Next, 60 parts of this fluorinated siloxanyl methacrylate C: 27 parts of methyl methacrylate, 10 parts of 2-hydroxyethyl methacrylate, 3 parts of diethylene glycol dimethacrylate, and 3.1 parts of azobisdimethylvaleronitrile were added and mixed well at room temperature. After that, test tube C was exposed to ultraviolet rays for 10 hours at 20℃, and 1 hour at 40℃.
After polymerizing at 50'C for 10 hours, UV irradiation was stopped.

5 hours at 60℃ and 5 hours at 80℃ 12 parts 5 hours at ℃
After polymerization for a period of time, a colorless and transparent rod-shaped copolymer was obtained, which was cut using a conventional method.

I polished it and made contact lenses.

The oxygen permeability coefficient in physiological saline (DKJJ, bovine blood groove albumin g: contamination resistance, Shore hardness + D) and non-recoverable deformability of these two contact lenses were investigated. The results shown in Table 1 below were obtained.

Example 2 The trifluoropropylmethylsiloxane trimer 15fi, 9 in Example 1 was replaced with nonafluorohexane methyl ν-xane trimer 30611 shown by the formula, and the formula 0 formula % was substituted for the zig-mouth methyl ν-ripvir methacrylate 12111. When treated in the same manner as in Example 1 except that chlorodimethylsilylbrobyl methacrylate "14.5II" represented by Therefore, this was copolymerized with the same methacrylate as in Example 1, and the physical properties of a contact lens made from this copolymer were examined, and the results shown in @1 Table C2 below were obtained.

Example 3 The jig mouth methyl ν rilp mouth methyl methacrylate 1211I of Example 1 was converted to trichlorosilylpropyl methacrylate 8 represented by the formula % formula %
Tris(dimethyltrifluoropropylsiloxy)silylpropyl methacrylate represented by formula 1 was obtained by processing in the same manner as in Example 1 except that 4,9(0,33 solu) was used.
This was copolymerized with the same methacrylate as in Example 1, a contact lens was made from this copolymer in the same manner as in Example 1, and the physical properties of this product were examined, and the results were as shown in Table 1 below. Obtained.

Example 4 Same as Example 1 except that 121 g of jig mouth methyl νlylpropyl methacrylate in Example 1 was changed to 192.5# (1 mol) of chlorodimethylsilylmethyl methacrylate shown by the formula % (
As a result of the second treatment, dimethyltrifluoropropylvroxydimetersilylmethyl methacrylate represented by the formula % was obtained. To 50 parts of this, 0.02 part of azobisisobutyronitrile was added and placed in a test tube. Mix well and incubate at 55°C for 10 hours at 80°C.
Polymerization was carried out at 120°C for 10 hours, at 120°C for 5 hours, and then at 150°C for 5 hours to obtain a colorless and transparent rod.

Next, this product was treated in the same manner as in Example 1 to make contact lenses, and when the physical properties of this material were investigated, the following
The results shown in the table were obtained.

Table 1 (Notes) *Contamination resistance: Bovine serum albumin C: No contamination with bovine serum albumin C was designated as O.

**Non-recoverable deformability...0.5Kg/c from the top of the lens
Press J for 1 minute, and when you release it, the lens curvature C remains unchanged and is marked with an ○.

Claims (1)

[Claims] 1. General formula ▲ Numerical formulas, chemical formulas, tables, etc. ~4 integer, m is 0, 1 or 2, n is an integer from 1 to 3), or a copolymer with other vinyl monomers. A contact lens characterized by: