Side-chain urethane-modified silicone macromers and copolymers thereof

Abstract

To provide a silicone macromer having improved compatibility with polymerizable hydrophilic monomers.SOLUTION: The present invention provides a side-chain urethane-modified silicone macromer represented by a formula (1). (In the formula (1), R's independently represent a group selected from an alkyl group, an aryl group and an aralkyl group, X's independently represent a hydrogen atom or a methyl group, and R1 is a group represented by a formula (2) or formula (3).SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to side-chain urethane-modified silicone macromers and copolymers thereof. [Background technology]

[0002] Due to its high oxygen permeability, silicone is widely used as a material for contact lenses. However, because silicone is non-hydrophilic, the introduction of hydrophilic groups has been reported to improve its compatibility with polymerizable hydrophilic monomers. As silicones with hydrophilic groups (silicone macromers), compounds with introduced hydroxyl groups (Patent Document 1) have been disclosed to date. The introduction of hydroxyl groups improves the compatibility of silicone macromers with polymerizable hydrophilic monomers. However, in order to allow for more freedom in the formulation of polymerizable hydrophilic monomers used as materials for contact lenses, it is desirable to further improve the compatibility of silicone macromers with polymerizable hydrophilic monomers. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] U.S. Patent Application Publication No. 2017 / 0008990 [Overview of the project] [Problems that the invention aims to solve]

[0004] Therefore, the present invention aims to provide a silicone macromer with improved compatibility with polymerizable hydrophilic monomers. [Means for solving the problem]

[0005] As a result of diligent research to achieve the above objective, the inventors discovered that adding a urethane moiety to the side chain of a silicone macromer improves its compatibility with polymerizable hydrophilic monomers, thus completing the present invention. In other words, the present invention provides a side-chain urethane-modified silicone macromer and its copolymer as described below.

[0006] <1> A side-chain urethane-modified silicone macromer represented by the following formula (1). [ka] (In formula (1), R is independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms; X is independently a hydrogen atom or a methyl group; n1 is independently a number from 2 to 10; n2 is a number from 0 to 8; R 1 is the group represented by formula (2) or formula (3) below, where a is a number from 0 to 400, and b is a number from 1 to 100, where a+b is 1 ≤ a+b ≤ 500. Note that the bonding of the siloxane units enclosed by a and b may be in blocks or random. [ka] (In formula (2), R 2 is the group shown in formula (4) below, where R is in formula (3). 3 (This is an independent hydrogen atom or a group represented by the following formula (4), and formula (1) contains at least one group represented by the following formula (4).) [ka] (In formula (4), R 4 (This group is selected from alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 10 carbon atoms, or aralkyl groups having 7 to 10 carbon atoms.) <2> In equation (4), R 4 This group is selected from aryl groups with 6 to 10 carbon atoms, or aralkyl groups with 7 to 10 carbon atoms. <1> Side-chain urethane-modified silicone macromer as described above. <3> A copolymer of the side-chain urethane-modified silicone macromer described in <1> or <2> and a polymerizable hydrophilic monomer. <4> The polymerizable hydrophilic monomer is one or more selected from acrylamide, methacrylamide, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-methyl-N-vinylacetamide, N-vinylpyrrolidone, N-vinylcaprolactam, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, N-hydroxyethylacrylamide, N-hydroxyethylmethacrylamide, N,N-dimethylaminopropylacrylamide, N,N-dimethylaminopropylmethacrylamide, N,N-dimethylaminoethyl acrylate, N,N-dimethylaminoethyl methacrylate, acrylic acid, And, The copolymer described in <3>, which is one or more selected from methacrylic acid. <5> A contact lens containing the copolymer described in <3> or <4>.

Advantages of the Invention

[0007] The side-chain urethane-modified silicone macromer of the present invention has a urethane moiety in the side chain, which improves its compatibility with the polymerizable hydrophilic monomer. Therefore, the side-chain urethane-modified silicone macromer of the present invention is suitable as a material for contact lenses and the like.

Brief Description of the Drawings

[0008] [Figure 1] It is a chart of the 1H-NMR spectrum of the side-chain urethane-modified silicone macromer obtained in Example 1.

Modes for Carrying Out the Invention

[0009] Hereinafter, the present invention will be described in detail.

[0010] The side-chain urethane-modified silicone macromer of the present invention is represented by the following formula (1). [Chemical formula] (In formula (1), R is independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms; X is independently a hydrogen atom or a methyl group; n1 is independently a number from 2 to 10; n2 is a number from 0 to 8; R 1 is a group represented by the following formula (2) or formula (3); a is a number from 0 to 400; b is a number from 1 to 100, provided that 1 ≤ a + b ≤ 500. The bonds of the siloxane units enclosed by a and b may be block or random.) [Chemical formula] (In formula (2), R 2 is a group represented by the following formula (4); in formula (3), R 3 is independently a hydrogen atom or a group represented by the following formula (4); in the above formula (1), there is at least one group represented by the following formula (4).) [Chemical formula] (In formula (4), R 4 is a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.)

[0011] In the above formula (1), R is independently a group selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. Examples of the alkyl group having 1 to 10 carbon atoms include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, octyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; etc. Examples of the aryl group having 6 to 10 carbon atoms include phenyl group, methylphenyl group, and ethylphenyl group. Examples of the aralkyl group having 7 to 10 carbon atoms include phenylmethyl group and phenylethyl group.) In formula (1) above, R is independently a hydrogen atom or a methyl group. n1 is independently 2 n2 is a number between 10 and 10, preferably between 2 and 4, and n2 is a number between 0 and 8, preferably between 1 and 3. a is a number between 0 and 400, preferably between 5 and 100, and b is a number between 1 and 100, preferably between 1 and 20. However, a+b is 1≦a+b≦500, preferably 6≦a+b≦120. The bonding of siloxane units enclosed by a and b may be in blocks or random.

[0012] In equation (2) above, R 2 This is the group represented by formula (4) above. In equation (3) above, R 3 Each is independently a hydrogen atom or a group represented by formula (4) above, and formula (1) contains at least one group represented by formula (4) above. In the above equation (4), R 4 The group is selected from alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 10 carbon atoms, or aralkyl groups having 7 to 10 carbon atoms. Examples of alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, propyl, butyl, and octyl groups; and cycloalkyl groups such as cyclopentyl and cyclohexyl groups. Examples of aryl groups having 6 to 10 carbon atoms include phenyl, methylphenyl, and ethylphenyl groups. Examples of aralkyl groups having 7 to 10 carbon atoms include phenylmethyl and phenylethyl groups.

[0013] [Manufacturing method for side-chain urethane-modified silicone macromers] The present invention's method for producing a side-chain urethane-modified silicone macromer (hereinafter sometimes abbreviated as "the present invention's method") comprises the step of reacting an isocyanate represented by the following formula (5) with a side-chain hydroxy-modified silicone macromer represented by the following formula (6). [ka] (In formula (5), R 4 (This group is selected from alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 10 carbon atoms, or aralkyl groups having 7 to 10 carbon atoms.) [ka] (In formula (6), R is independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms; X is independently a hydrogen atom or a methyl group; n1 is independently a number from 2 to 10; n2 is a number from 0 to 8; R 5 is the group represented by formula (7) or (8) below, where a is a number from 0 to 400 and b is a number from 1 to 100, and where a+b is 1 ≤ a+b ≤ 500. Note that the bonding of the siloxane units enclosed by a and b may be in blocks or random. [ka]

[0014] In the above equation (5), R 4 The group is selected from alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 10 carbon atoms, or aralkyl groups having 7 to 10 carbon atoms. Examples of alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, propyl, butyl, and octyl groups; and cycloalkyl groups such as cyclopentyl and cyclohexyl groups. Examples of aryl groups having 6 to 10 carbon atoms include phenyl, methylphenyl, and ethylphenyl groups. Examples of aralkyl groups having 7 to 10 carbon atoms include phenylmethyl and phenylethyl groups.

[0015] In formula (6) above, R is independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. Examples of alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, propyl, butyl, and octyl groups; and cycloalkyl groups such as cyclopentyl and cyclohexyl groups. Examples of aryl groups having 6 to 10 carbon atoms include phenyl, methylphenyl, and ethylphenyl groups. Examples of aralkyl groups having 7 to 10 carbon atoms include phenylmethyl and phenylethyl groups. In formula (6) above, R is independently a hydrogen atom or a methyl group. n1 is independently 2 n2 is a number between 10 and 10, preferably between 2 and 4, and n2 is a number between 0 and 8, preferably between 1 and 3. a is a number between 0 and 400, preferably between 5 and 100, and b is a number between 1 and 100, preferably between 1 and 20. However, a+b is 1≦a+b≦500, preferably 6≦a+b≦120. The bonding of siloxane units enclosed by a and b may be in blocks or random.

[0016] In the manufacturing method of the present invention, the molar ratio of the isocyanate represented by formula (5) to the hydroxyl group in formula (6) is preferably 0.1 to 2 times, and more preferably 0.5 to 1 time.

[0017] As the catalyst used in the manufacturing method of the present invention, known urethane catalysts can be used. Examples of urethane catalysts include tertiary amines such as triethylamine and 1,4-diazabicyclo[2.2.2]octane; and organometallic compounds such as iron(III) acetylacetonate, dibutyltin dilaurate, dioctyltin dilaurate, bismuth 2-ethylhexanoate, bismuth octanoate, tetrabutyl orthotitanate, titanium diisopropoxide bis(acetylacetonate), zirconium tetrabutoxide, and zirconium tetraacetylacetonate. Among these, iron(III) acetylacetonate is preferred.

[0018] In the manufacturing method of the present invention, the amount of catalyst is not particularly limited. Preferably, it is 10 to 1,000 ppm relative to the weight of the hydroxy-modified silicone macromer represented by formula (6).

[0019] In the manufacturing method of the present invention, the reaction temperature in the step of reacting a hydroxy-modified silicone macromer represented by formula (6) with an isocyanate represented by formula (5) in the presence of a urethane catalyst is preferably 40°C or higher and 90°C or lower, and more preferably 50°C or higher and 70°C or lower.

[0020] In the manufacturing method of the present invention, the reaction conditions, such as the reaction time and the solvent used, are not particularly limited. The reaction time is preferably 1 to 24 hours, more preferably 1 to 12 hours, and most preferably 2 to 6 hours. The solvent is preferably an aromatic hydrocarbon solvent such as toluene or xylene.

[0021] The side-chain urethane-modified silicone macromer of the present invention exhibits excellent compatibility with polymerizable hydrophilic monomers, making it easy to form copolymers. Preferred examples of the polymerizable hydrophilic monomers include acrylamide-based monomers such as acrylamide, methacrylamide, N,N-dimethylacrylamide, and N,N-dimethylmethacrylamide; vinylamide-based monomers such as N-methyl-N-vinylacetamide; N-vinylcyclic amide-based monomers such as N-vinylpyrrolidone and N-vinylcaprolactam; hydroxyl-based monomers such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, N-hydroxyethylacrylamide, and N-hydroxyethyl methacrylamide; amino-based monomers such as N,N-dimethylaminopropylacrylamide, N,N-dimethylaminopropyl methacrylamide, N,N-dimethylaminoethyl acrylate, and N,N-dimethylaminoethyl methacrylate; and carboxylic acid-based monomers such as acrylic acid and methacrylic acid.

[0022] The amount of polymerizable hydrophilic monomer that forms the copolymer is preferably 50 to 1,000 parts by mass, more preferably 100 to 500 parts by mass, per 100 parts by mass of side-chain urethane-modified silicone macromer.

[0023] Polymerization is carried out by heat or ultraviolet irradiation. These methods are well known in the field. Polymerization by ultraviolet irradiation is carried out by adding a photopolymerization initiator to a side-chain urethane-modified silicone macromer and a polymerizable hydrophilic monomer, and then irradiating with ultraviolet light. A typical photopolymerization initiator is 2-hydroxy-2-methyl-1-phenylpropanone (trade name: Omnirad-1173, manufactured by IGM Resins BV), but is not limited to this. [Examples]

[0024] The present invention will be described in more detail below with reference to examples, but may be modified as appropriate without departing from the spirit of the invention. Accordingly, the scope of the present invention should not be interpreted as being limited by the specific examples shown below.

[0025] Synthesis of side-chain urethane-modified silicone macromers [Example 1] In a separable flask equipped with a thermometer, stirrer, and reflux condenser, 100.0 g of the side-chain hydroxy-modified silicone macromer shown in formula (a) below, 9.3 g of phenyl isocyanate (an amount such that the ratio of moles of isocyanate to the total number of moles of hydroxyl groups in the side-chain hydroxy-modified silicone macromer is 1.0), 0.0030 g of iron(III) acetylacetonate, 0.010 g of dibutylhydroxytoluene, 0.010 g of 4-methoxyphenol, and 30 g of toluene were charged and heated and stirred at 60°C for 5 hours. After the reaction was complete, 1.5 g of Kyoward 2000 (manufactured by Kyowa Chemical Industry Co., Ltd.) was added and stirred at room temperature for 1.5 hours. The solid was removed by pressure filtration. The low-boiling fraction was removed under reduced pressure of 0.4 kPa at 75°C for 2 hours to obtain 94.9 g of the side-chain urethane-modified silicone macromer shown in formula (b) below. [ka]

[0026] The following describes the side-chain urethane-modified silicone macromer obtained in Example 1. 1 The H-NMR spectrum and, as shown in Figure 1, 1 The 1H-NMR spectrum chart is shown. 1H-NMR(400MHz, CDCl3):δ -0.51~0.21(m,540H), 0.35~0.57(m,16H), 1.47~1.70(m,16H), 1.87(s,6H), 3.37(t,J=7.1Hz,12H), 3.59(t ,J=4.6Hz,12H), 4.03(t,J=7.0Hz,4H), 4.24(t,J=4.4Hz,12H), 5.46(s,2H), 6.03(s,2H), 6.49~7.41(m,30H)

[0027] [Example 2] The synthesis was carried out in the same manner as in Example 1, except that 100.0 g of the side-chain hydroxy-modified silicone macromer shown in formula (a) above, 9.8 g of cyclohexyl isocyanate (an amount such that the ratio of moles of isocyanate to the total number of moles of hydroxyl groups in the side-chain hydroxy-modified silicone macromer is 1.0), 0.0030 g of iron(III) acetylacetonate, 0.010 g of dibutylhydroxytoluene, 0.010 g of 4-methoxyphenol, and 30 g of toluene were used. 93.6 g of the side-chain urethane-modified silicone macromer shown in formula (c) below was obtained. [ka]

[0028] The following describes the side-chain urethane-modified silicone macromer obtained in Example 2. 1 The H-NMR spectrum is shown. 1 H-NMR(400MHz, CDCl3):δ -0.26~0.23(m,540H), 0.41~0.59(m,16H), 1.02~1.20(m,18H), 1.24~1.40(m,12H), 1.51~1.73(m,34H), 1.82~1.95(m,18H), 3.2 9~3.51(m,18H), 3.58(t,J=4.5Hz,12H), 4.08(t,J=6.8Hz,4H), 4.16(t,J=3.8Hz,12H), 4.63(brs,6H), 5.51(s,2H), 6.08(s,2H)

[0029] [Example 3] The synthesis was carried out in the same manner as in Example 1, except that 200.0 g of the side-chain hydroxy-modified silicone macromer shown in formula (d) below, 18.2 g of phenyl isocyanate (an amount such that the ratio of moles of isocyanate to the total number of moles of hydroxyl groups in the side-chain hydroxy-modified silicone macromer is 0.5), 0.0060 g of iron(III) acetylacetonate, 0.020 g of dibutylhydroxytoluene, 0.020 g of 4-methoxyphenol, and 70 g of toluene were used. 189 g of the side-chain urethane-modified silicone macromer shown in formula (e) below was obtained. [ka] (In the above formula (e), R 6 and R 7 (wherein is a hydrogen atom or a group represented by formula (9) above, and on average, one molecule contains six hydrogen atoms and six groups represented by formula (9) above.)

[0030] The following describes the side-chain urethane-modified silicone macromer obtained in Example 3. 1 The H-NMR spectrum is shown. 1 H-NMR(400MHz, CDCl3):δ -0.39~0.24(m,540H), 0.34~0.57(m,16H), 1.45~1.71(m,16H), 1.87(s,6H), 3.25~3.50(m,20H), 3.52~3.69(m,8H), 3.73 ~3.86(m,4H), 3.93~4.00(m,2H), 4.03(t,J=7.0Hz,4H), 4.07~4.41(m,8H), 5.47(s,2H), 6.03(s,2H), 6.61~7.43(m,30H)

[0031] [Example 4] The synthesis was carried out in the same manner as in Example 1, except that 200.0 g of the side-chain hydroxy-modified silicone macromer shown in formula (d) above, 34.6 g of phenyl isocyanate (an amount such that the ratio of moles of isocyanate to the total number of moles of hydroxyl groups in the side-chain hydroxy-modified silicone macromer is 1.0), 0.0120 g of iron(III) acetylacetonate, 0.020 g of dibutylhydroxytoluene, 0.020 g of 4-methoxyphenol, and 100 g of toluene were used. 197 g of the side-chain urethane-modified silicone macromer shown in formula (f) below was obtained. [ka]

[0032] The following describes the side-chain urethane-modified silicone macromer obtained in Example 4. 1 The H-NMR spectrum is shown. 1 H-NMR(400MHz, CDCl3):δ -0.37~0.16(m,540H), 0.34~0.54(m,16H), 1.44~1.68(m,16H), 1.87(s,6H), 3.28~3.43(m,12H), 3.53~ 3.63(m,12H), 4.03(t,J=6.8Hz,4H), 4.24~4.45(m,12H), 5.46(s,2H), 6.03(s,2H), 6.58~7.43(m,60H)

[0033] [Example 5] The synthesis was carried out in the same manner as in Example 1, except that 200.0 g of the side-chain hydroxy-modified silicone macromer shown in formula (d) above, 19.1 g of cyclohexyl isocyanate (an amount such that the ratio of moles of isocyanate to the total number of moles of hydroxyl groups in the side-chain hydroxy-modified silicone macromer is 0.5), 0.0060 g of iron(III) acetylacetonate, 0.020 g of dibutylhydroxytoluene, 0.020 g of 4-methoxyphenol, and 70 g of toluene were used. 195 g of the side-chain urethane-modified silicone macromer shown in formula (g) below was obtained.

[0034] [ka] (In the above formula (g), R 8 and R 9 (These are hydrogen atoms or the group represented by formula (10) above, and on average, one molecule contains six hydrogen atoms and six groups represented by formula (10) above.)

[0035] The following describes the side-chain urethane-modified silicone macromer obtained in Example 5. 1 The H-NMR spectrum is shown. 1 The 1H-NMR spectrum is shown below. 1 H-NMR(400MHz, CDCl3):δ -0.37~0.27(m,540H), 0.36~0.60(m,16H), 0.97~1.21(m,18H), 1.21~1.39(m,12H), 1 .47~1.78(m,34H), 1.80~1.98(m,18H), 3.21~4.29(m,52H), 5.51(s,2H), 6.07(s,2H)

[0036] [Compatibility Test] [Test Examples 1-3] Compatibility tests were conducted on the side-chain urethane-modified silicone macromers represented by formulas (b), (e), and (f) above. The same weight of polymerizable hydrophilic monomer was added to the silicone macromer to check for compatibility. The polymerizable hydrophilic monomers included dimethylacrylamide (DMAA) and N-vinylpyrrolic acid. Do NvP (NVP) and 2-hydroxyethyl methacrylate (HEMA) were used. A compatibility test was performed, with a "○" indicating a clear, homogeneous liquid mixture and a "×" indicating a non-clear, homogeneous liquid mixture. The results are shown in Table 1. [Comparative Test Examples 1-2] Compatibility tests were conducted in the same manner as in Test Examples 1-3, except that a side-chain hydroxy-modified silicone macromer was used instead of a side-chain urethane-modified silicone macromer. The results are shown in Table 1.

[0037] [Table 1]

[0038] The side-chain urethane-modified silicone macromer of the present invention showed higher compatibility with polymerizable hydrophilic monomers compared to the side-chain hydroxy-modified silicone macromers of Comparative Test Examples 1 and 2.

[0039] Synthesis of copolymers [Example 6] Three g of the side-chain urethane-modified silicone macromer shown in formula (b) above, three g of N-vinylpyrrolidone (NVP), and 0.02 g of 2-hydroxy-2-methyl-1-phenylpropanone (trade name: Omnirad-1173, manufactured by IGM Resins BV) were mixed and stirred until a homogeneous solution was obtained. After standing and degassing, the mixture was sealed in a mold. UV irradiation was performed using a metal halide lamp (wavelength 365 nm, irradiation dose 95,000 mJ / cm²). 2 The procedure was performed and cured at room temperature (20°C). The cured product was a transparent solid. [Industrial applicability]

[0040] The silicone macromer of the present invention has high compatibility with polymerizable hydrophilic monomers and is therefore useful as a material for contact lenses and the like.

Claims

1. A side-chain urethane-modified silicone macromer represented by the following formula (1). 【Chemistry 1】 (In formula (1), R is independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms; X is independently a hydrogen atom or a methyl group; n1 is independently a number from 2 to 10; n2 is a number from 0 to 8; R 1 is a group represented by formula (2) or formula (3) below, where a is a number from 0 to 400, and b is a number from 1 to 100, where a + b is 1 ≤ a + b ≤ 500. Note that the bonding of the siloxane units enclosed by a and b may be in blocks or random. 【Chemistry 2】 (In formula (2), R 2 is the group shown in formula (4) below, where R is in formula (3). 3 (This is an independent hydrogen atom or a group represented by the following formula (4), and formula (1) contains at least one group represented by the following formula (4).) 【Transformation 3】 (In formula (4), R 4 (This group is selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.)

2. In equation (4), R 4 The side-chain urethane-modified silicone macromer according to claim 1, wherein the group is selected from an aryl group having 6 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms.

3. A copolymer of a side-chain urethane-modified silicone macromer and a polymerizable hydrophilic monomer according to claim 1.

4. The copolymer according to claim 3, wherein the polymerizable hydrophilic monomer is one or more selected from acrylamide, methacrylamide, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-methyl-N-vinylacetamide, N-vinylpyrrolidone, N-vinylcaprolactam, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, N-hydroxyethyl acrylamide, N-hydroxyethyl methacrylamide, N,N-dimethylaminopropyl acrylamide, N,N-dimethylaminopropyl methacrylamide, N,N-dimethylaminoethyl acrylate, N,N-dimethylaminoethyl methacrylate, acrylic acid, and methacrylic acid.

5. A contact lens comprising the copolymer described in claim 3.

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