# US 5,708,049 A · Colored contact lens and method for producing the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,708,049 A - Document ID: US5708049A - Status: Granted - Kind: A - Application number: 08/597,811 - Filed: 1996-02-07 - Granted: 1998-01-13 - Earliest claimed: 1995-02-07 - Assignees: Seiko Epson Corporation - Inventors: Hiroshi Katagiri; Tadao Kojima; Youichi Ushiyama - Web page: https://patentgrep.com/patent/US5708049A ## CPC - C08F 2/44: Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers - C09B 69/108: {containing a phthalocyanine dye} - G02B 1/043: {Contact lenses} - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) - G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS ## Abstract A contact lens colored with a poly(meth)acrylate-combined metallophthalocyanine compound represented by the following formula (I): ##STR1## wherein M represents a metal atom to which phthalocyanine can coordinate, R represents a halogen atom, m is an integer of 0 to 4, R.sup.1 represents a hydrogen atom or a methyl group, and A represents a hydrogen atom, a C.sub.1-12 alkyl group, a hydroxyC.sub.1-12 alkyl group or a glycerol group. The colored contact lens has sufficiently high fastness, so that the lens undergoes neither color change nor color fading even when it is sterilized by boiling. ## Claims ### Claim 1 A colored contact lens comprising a polymer as a main component of the contact lens and a poly(meth) acrylate-combined metallopthalocyanine compound represented by the following formula (I) ##STR6## wherein M represents a metal atom to which phthalocyanine can coordinate, R represents a halogen atom or a bond with the poly(meth)acrylate moiety, m is an integer of 0 to 4, provided that one of Rs in the phthalocyanine group represents the bond with the poly(meth)acrylate moiety, R.sup.1 represents a hydrogen atom or a methyl group, A represents a hydrogen atom, a C.sub.1-12 alkyl group, a hydroxyC.sub.1-12 alkyl group or a glycerol group, and n is an integer sufficient to substantially prevent elution of the compound of formula (I) into the eye of the user. ### Claim 2 (depends on 1) The colored contact lens according to claim 1, wherein the polymer is a poly(meth)acrylate. ### Claim 3 (depends on 1) The colored contact lens according to claim 1, wherein the polymer is obtained by polymerizing monomers comprising N,N-dimethylacrylamide, a fluoroalkyl (meth)acrylate and a siloxanyl (meth)acrylate. ### Claim 4 (depends on 1) The colored contact lens according to claim 1 which is a soft contact lens having a water content of 45% or higher. ### Claim 5 (depends on 1) The colored contact lens according to claim 1, wherein M is copper. ### Claim 6 (depends on 1) The colored contact lens according to claim 1, wherein m is an integer of 1 to 4, and R represents chlorine or bromine. ### Claim 7 (depends on 1) The colored contact lens according to claim 1, wherein the poly(meth)acrylate-combined methallophthalocyanine compound represented by the formula (I) has a number-average molecular weight of 5,000 to 500,000. ### Claim 8 (depends on 1) The colored contact lens according to claim 1, wherein A is an alkyl group having 1 to 12 carbon atoms. ### Claim 9 (depends on 3) A process for producing a colored contact lens, comprising the steps of: dispersing and dissolving the coloring agent according to claim 3 in a polymerizable monomer as a starting material for the contact lens to obtain a mixture, polymerizing the polymerizable monomer contained in the mixture to obtain a polymer, and processing the polymer into a contact lens. ### Claim 10 A process for producing a colored contact lens, comprising the steps of: a) dispersing and dissolving a poly(meth) acrylate-combined metallophthalocyanine compound in a polymerizable monomer as a starting material for the contact lens to obtain a mixture, said compound having a formula (I) as follows: ##STR7## wherein M represents a metal atom to which phthalocyanine can coordinate, R represents a halogen atom or a bond with the poly(meth)acrylate moiety, m is an integer of 0 to 4, provided that one of Rs in the phthalocyanine group represents the bond with the poly(meth)acrylate moiety, R.sup.1 represents a hydrogen atom or a methyl group, A represents a hydrogen atom, a C.sub.1-12 alkyl group, a hydroxyC.sub.1-12 alkyl group or a glycerol group, and n is an integer sufficient to substantially prevent elution of the compound of formula (I) into the eye of the user, b) polymerizing the polymerizable monomer contained in the mixture to obtain a polymer, and c) processing the polymer into a contact lens. ### Claim 11 In a process for producing a contact lens comprising the steps of a) polymerizing a polymerizable monomer to obtain a polymer; b) processing the polymer into a contact lens having a shape and curvature to fit over the cornea of an eye of a user; and c) soaking the contact lens in water or saline and allowing it to swell so as to form the contact lens with a water contact of at least 45%, said contact lens having a measurable average breaking strength and average elongation, the improvement comprising dispersing and dissolving with the polymerizable monomer in step (a) a poly(meth) acrylate-combined metallophthalocyanine compound represented by the following formula (I): ##STR8## wherein M represents a metal atom to which phthalocyanine can coordinate, R represents a halogen atom or a bond with the poly(meth)acrylate moiety, m is an integer of 0 to 4, provided that one of Rs in the phthalocyanine group represents the bond with the poly(meth)acrylate moiety, R.sup.1 represents a hydrogen atom or a methyl group, A represents a hydrogen atom, a C.sub.1-12 alkyl group, a hydroxyC.sub.1-12 alkyl group or a glycerol group, and n is an integer sufficient to substantially prevent elution of the compound of formula (I) into the eye of the user, said compound of formula (I) being dispersed and dissolved in the polymerizable monomer in step (a) in an amount sufficient to form the contact lens with an improved average breaking strength and an improved average elongation and to impart color to the contact lens. ### Claim 12 (depends on 11) The process as claimed in claim 11, wherein the compound of formula (I) is dispersed and dissolved in the polymerizable monomer of step (a) in an amount sufficient to form the contact lens with an average breaking strength and an average elongation that is higher by at least 20% and 15% respectively as compared to the contact lens formed in step (c) without the compound of formula (I). ### Claim 13 (depends on 11) The contact lens obtained by the process of claim 11. ### Claim 14 (depends on 13) The contact lens of claim 13, wherein the compound (I) is present in an amount of about 0.001 to 2% by dry weight of the contact lens. ### Claim 15 (depends on 14) The contact lens of claim 14, wherein the contact lens has a thickness of between about 0.06 mm to 0.1 mm. ### Claim 16 (depends on 10) The colored contact lens obtained by the process according to claim 10. ### Claim 17 (depends on 10) The process for producing a colored contact lens according to claim 10, wherein the polymerizable monomer is a (meth)acrylate. ### Claim 18 (depends on 10) The process for producing a colored contact lens according to claim 10, wherein the polymerizable monomer comprises N,N-dimethylacrylamide, a fluoroalkyl (meth)acrylate and a siloxanyl (meth)acrylate.