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US20060115516A1 - Copolymerizable methine and anthraquinone compounds and articles containing them - Google Patents

Copolymerizable methine and anthraquinone compounds and articles containing themDownload PDF

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US20060115516A1
US20060115516A1US11/271,382US27138205AUS2006115516A1US 20060115516 A1US20060115516 A1US 20060115516A1US 27138205 AUS27138205 AUS 27138205AUS 2006115516 A1US2006115516 A1US 2006115516A1
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Jason Pearson
Max Weaver
Jean Fleischer
Gregory King
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Johnson and Johnson Surgical Vision Inc
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Assigned to EASTMAN CHEMICAL COMPANYreassignmentEASTMAN CHEMICAL COMPANYASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: FLEISCHER, JEAN CARROLL, KING, GREG ALAN, PETERSON, JASON CLAY, WEAVER, MAX ALLEN
Assigned to ADVANCED MEDICAL OPTICS, INC.reassignmentADVANCED MEDICAL OPTICS, INC.ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS).Assignors: EASTMAN CHEMICAL COMPANY
Assigned to BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENTreassignmentBANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENTINTELLECTUAL PROPERTY SECURITY AGREEMENTAssignors: ADVANCED MEDICAL OPTICS, INC.
Priority to US12/257,277prioritypatent/US8360576B2/en
Assigned to ADVANCED MEDICAL OPTICS, INC.reassignmentADVANCED MEDICAL OPTICS, INC.RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS).Assignors: BANK OF AMERICA, N.A. AS ADMINISTRATIVE AGENT
Priority to US13/622,160prioritypatent/US8501890B2/en
Priority to US13/959,404prioritypatent/US8785627B2/en
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Abstract

This invention relates to polymerizable ultraviolet light absorbers and yellow colorants and their use in ophthalmic lenses. In particular, this invention relates to polymerizable ultraviolet light absorbing methine compounds and yellow compounds of the methine and anthraquinone classes that block ultraviolet light and/or violet-blue light transmission through ophthalmic lenses.

Description

Claims (40)

Figure US20060115516A1-20060601-C00127
wherein:
R and R1are independently selected from C1-C12-alkyl, substituted C1-C12-alkyl, aryl, heteroaryl, C3-C8-cycloalkyl, C3-C8-alkenyl, —(CHR′CHR″O—)n—R4, C1-C6-alkylsulfonyl, arylsulfonyl, C1-C12-acyl, substituted-C1-C12-acyl, -L-Q and -Q; or R and R1are combined to make phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;
n is an integer from 1 to about 1000;
R2is selected from hydrogen or one or two groups selected from C1-C6alkyl, C1-C6alkoxy and halogen;
R3is selected from hydrogen, C1-C12-alkyl, substituted C1-C12-alkyl, aryl, C3-C8-cycloalkyl, C3-C8-alkenyl and —(CHR′CHR″O—)n—R4, C1-C12-acyl, substituted-C1-C12-acyl, -L-Q and Q;
R4is selected from hydrogen, C1-C12-alkyl, C1-C6-alkanoyl and aryl;
R′ and R″ are independently selected from hydrogen and C1-C12-alkyl;
L is a divalent organic radical selected from C1-C6-alkylene-O—, C1-C6-alkylene-NR′—; arylene-C1-C6-alkylene-O—, arylene-C1-C6-alkylene-NR′—, arylene-O(CHR′CHR″O)n—, C1-C6-alkylene-Y1—(CHR′CHR″O—)n—, and —(CHR′CHR″O—)n—;
Y is selected from —O-L-Q, —NR′-L-Q, —N-(L-Q)2, and —R5;
Y1is selected from —O—, —S—, —SO2—, —N(SO2R5)—, and —N(COR5)—;
R5is C1-C12-alkyl, substituted C1-C12-alkyl, C3-C8-cycloalkyl or aryl;
X1and X2are independently selected from cyano, —CO2C1-C6-alkyl, C1-C6-alkylsulfonyl, arylsulfonyl, carbamoyl, C1-C6-alkanoyl, aroyl, aryl, heteroaryl and —COY;
Q is a group that comprises an ethylenically unsaturated polymerizable group;
the molecule comprises at least one Q group.
7. The intraocular lens ofclaim 6, wherein the molecular structure is depicted by Formula II, wherein:
R and R1are independently selected from C1-C12-alkyl, substituted C1-C12-alkyl, aryl, heteroaryl, C3-C8-cycloalkyl, C3-C8-alkenyl, —(CHR′CHR″O—)n—R4, C1-C6-alkylsulfonyl, arylsulfonyl, C1-C12-acyl, substituted-C1-C12-acyl, -L-Q and -Q; or R and R1are combined to make cyclic phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;
n is an integer from 1 to about 1000;
R2is selected from hydrogen or one or two groups selected from hydroxy, C1-C6alkyl, C1-C6alkoxy and halogen;
R′ and R″ are independently selected from hydrogen and C1-C12-alkyl;
L is a divalent organic radical selected from C1-C6-alkylene-O—, C1-C6-alkylene-NR′—; arylene-C1-C6-alkylene-O—, arylene-C1-C6-alkylene-NR′—, arylene-O(CHR′CHR″O)n—, C1-C6-alkylene-Y1—(CHR′CHR″O—)n—, and —(CHR′CHR″O—)n—;
Y is selected from —O-L-Q, —NR′-L-Q, —N-(L-Q)2, and —R5;
Y1is selected from —O—, —S—, —SO2—, —N(SO2R5)—, and —N(COR5)—;
R4is selected from hydrogen, C1-C12-alkyl, C1-C6-alkanoyl and aryl;
R5is C1-C12-alkyl, substituted C1-C12-alkyl, C3-C8-cycloalkyl or aryl;
X1and X2are independently selected from cyano, —CO2C1-C6-alkyl, C1-C6-alkylsulfonyl, arylsulfonyl, carbamoyl, C1-C6-alkanoyl, aroyl, aryl, heteroaryl and —COY; and
Q is a group that comprises an ethylenically unsaturated polymerizable group that does not include any carbons actually pictured in Formula II.
8. The intraocular lens ofclaim 6, the molecular structure is depicted by Formula II, wherein:
R and R1are independently selected from C1-C12-alkyl, substituted C1-C12-alkyl, and aryl; or R and R1are combined to make phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;
R2is selected from hydrogen, C1-C6-alkyl, C1-C6-alkoxy and halogen;
R1is selected from hydrogen and C1-C12-alkyl;
L is C1-C6-alkylene-O;
Y is selected from —O-L-Q, —NR′-L-Q, and —N-(L-Q)2;
X1is selected from cyano, —CO2C1-C6-alkyl, C1-C6-alkylsulfonyl, arylsulfonyl, carbamoyl, C1-C6-alkanoyl, aroyl, aryl, and heteroaryl;
X2is —COY;
Q is:
(a) —COC(R6)═CH—R7,
(b) —CONHCOC(R6)═CH—R7,
(c) —CONH—C1-C6-alkylene-OCOC(R6)═CH—R7,
Figure US20060115516A1-20060601-C00128
Figure US20060115516A1-20060601-C00129
Figure US20060115516A1-20060601-C00142
wherein:
R2is selected from hydrogen or one or two groups selected from hydroxy, C1-C6alkyl, C1-C6alkoxy and halogen;
R3is selected from hydrogen, C1-C12-alkyl, substituted C1-C12-alkyl, aryl, C3-C8-cycloalkyl, C3-C8-alkenyl, —(CHR′CHR″O—)n—R4, C1-C12-acyl, substituted-C1-C12-acyl and -L-Q;
n is an integer selected from 1 to about 1000;
R4is selected from hydrogen, C1-C12-alkyl, C1-C6-alkanoyl and aryl;
R′ and R″ are independently selected from hydrogen and C1-C12-alkyl;
L is a divalent organic radical selected from C1-C6-alkylene-O—, C1-C6-alkylene-NR′—; arylene-C1-C6-alkylene-O—, arylene-C1-C6-alkylene-NR′—, arylene-O(CHR′CHR″O)n—, C1-C6-alkylene-Y1—(CHR′CHR″O—)n—, and —(CHR′CHR″O—)n—;
Y is selected from —NR′-L-Q, —N-(L-Q)2, and —R5;
Y1is selected from —O—, —S—, —SO2—, —N(SO2R5)—, and —N(COR5)—;
R5is C1-C12-alkyl, substituted C1-C12-alkyl, C3-C8-cycloalkyl or aryl;
X1and X2are independently selected from cyano, —CO2C1-C6-alkyl, C1-C6-alkylsulfonyl, arylsulfonyl, carbamoyl, C1-C6-alkanoyl, aroyl, aryl, heteroaryl and —COY;
Q is a group that includes an ethylenically-unsaturated polymerizable group;
the compound comprises at least one Q group.
Figure US20060115516A1-20060601-C00143
wherein:
R2is selected from hydrogen or one or two groups selected from hydroxy, C1-C6alkyl, C1-C6alkoxy and halogen;
R3is selected from hydrogen, C1-C12-alkyl, substituted C1-C12-alkyl, aryl, C3-C8-cycloalkyl, C3-C8-alkenyl, —(CHR′CHR″O—)n—R4, C1-C12-acyl, substituted-C1-C12-acyl and -L-Q;
n is an integer from 1 to about 1000;
R4is selected from hydrogen, C1-C12-alkyl, C1-C6-alkanoyl and aryl;
R′ and R″ are independently selected from hydrogen and C1-C12-alkyl;
L is a divalent organic radical selected from C1-C6-alkylene-O—, C1-C6-alkylene-NR′—; arylene-C1-C6-alkylene-O—, arylene-C1-C6-alkylene-NR′—, arylene-O(CHR′CHR″O)n—, C1-C6-alkylene-Y1—(CHR′CHR″O—)n—, and —(CHR′CHR″O—)n—;
Y is selected from —NR′-L-Q, —N-(L-Q)2, and —R5;
Y1is selected from —O—, —S—, —SO2—, —N(SO2R5)—, and —N(COR5)—;
R5is C1-C12-alkyl, substituted C1-C12-alkyl, C3-C8-cycloalkyl or aryl;
X1and X2are independently selected from cyano, —CO2C1-C6-alkyl, C1-C6-alkylsulfonyl, arylsulfonyl, carbamoyl, C1-C6-alkanoyl, aroyl, aryl, heteroaryl and —COY;
Q is:
(a) —COC(R6)═CH—R7,
(b) —CONHCOC(R6)═CH—R7,
(c) —CONH—C1-C6-alkylene-OCOC(R6)═CH—R7,
Figure US20060115516A1-20060601-C00144
Figure US20060115516A1-20060601-C00146
wherein:
R and R1are independently selected from C1-C12-alkyl, substituted C1-C12-alkyl, aryl, heteroaryl, C3-C8-cycloalkyl, C3-C8-alkenyl, —(CHR′CHR″O—)n—R4, C1-C6-alkylsulfonyl, arylsulfonyl, C1-C12-acyl, substituted-C1-C12-acyl, -L-Q and -Q; or R and R1are combined to make phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;
R2is selected from hydrogen or one or two groups selected from hydroxy, C1-C6alkyl, C1-C6alkoxy and halogen;
R′ and R″ are independently selected from hydrogen and C1-C12-alkyl;
L is a divalent organic radical selected from C1-C6-alkylene-O—, C1-C6-alkylene-NR′—; arylene-C1-C6-alkylene-O—, arylene-C1-C6-alkylene-NR′—, arylene-O(CHR′CHR″O)n—, C1-C6-alkylene-Y1—(CHR′CHR″O—)n—, and —(CHR′CHR″O—)n—;
Y is selected from —NR′-L-Q, and —N-(L-Q)2;
Y1is selected from —O—, —S—, —SO2—, —N(SO2R5)—, and —N(COR5)—;
R4is selected from hydrogen, C1-C12-alkyl, C1-C6-alkanoyl and aryl;
R5is C1-C12-alkyl, substituted C1-C12-alkyl, C3-C8-cycloalkyl or aryl;
n is an integer from 1 to 100;
X1is selected from cyano, —CO2—C1-C6-alkyl, C1-C6-alkylsulfonyl, arylsulfonyl, carbamoyl, C1-C6-alkanoyl, aroyl, aryl, heteroaryl and —COY;
X2is —COY or carbamoyl;
Q is:
(a) —COC(R6)═CH—R7,
(b) —CONHCOC(R6)═CH—R7,
(c) —CONH—C1-C6-alkylene-OCOC(R6)═CH—R7,
Figure US20060115516A1-20060601-C00147
Figure US20060115516A1-20060601-C00158
wherein:
R and R1are independently selected from C1-C12-alkyl, substituted C1-C12-alkyl, aryl, heteroaryl, C3-C8-cycloalkyl, C3-C8-alkenyl, —(CHR′CHR″O—)n—R4, C1-C6-alkylsulfonyl, arylsulfonyl, C1-C12-acyl, substituted-C1-C12-acyl, -L-Q and -Q; or R and R1are combined to make phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;
n is an integer between from 1 to about 1000;
R2is selected from hydrogen or one or two groups selected from C1-C6alkyl, C1-C6alkoxy and halogen;
R3is selected from hydrogen, C1-C12-alkyl, substituted C1-C12-alkyl, aryl, C3-C8-cycloalkyl, C3-C8-alkenyl and —(CHR′CHR″O—)n—R4, C1-C12-acyl, substituted-C1-C12-acyl, -L-Q and Q; or R and
R4is selected from hydrogen, C1-C12-alkyl, C1-C6-alkanoyl and aryl;
R′ and R″ are independently selected from hydrogen and C1-C12-alkyl;
L is a divalent organic radical selected from C1-C6-alkylene-O—, C1-C6-alkylene-NR′—; arylene-C1-C6-alkylene-O—, arylene-C1-C6-alkylene-NR′—, arylene-O(CHR′CHR″O)n—, C1-C6-alkylene-Y1—(CHR′CHR″O—)n—, and —(CHR′CHR″O—)n—;
Y is selected from —O-L-Q, —NR′-L-Q, —N-(L-Q)2, and —R5;
Y1is selected from —O—, —S—, —SO2—, —N(SO2R5)—, and —N(COR5)—;
R4is selected from hydrogen, C1-C12-alkyl, C1-C6-alkanoyl and aryl;
R5is C1-C12-alkyl, substituted C1-C12-alkyl, C3-C8-cycloalkyl or aryl;
X1and X2are independently selected from cyano, —CO2C1-C6-alkyl, C1-C6-alkylsulfonyl, arylsulfonyl, carbamoyl, C1-C6-alkanoyl, aroyl, aryl, heteroaryl and —COY;
Q is a group that comprises an ethylenically unsaturated polymerizable group;
the molecule, before copolymerization, comprises at least one Q group;
the residue comprises a reaction product of saturation of the Q group; and
the molecule optionally comprises one or more additional atoms or moieties not shown by Formula II, Formula III, Formula IV, Formula V, or Formula VI.
US11/271,3822004-11-222005-11-10Copolymerizable methine and anthraquinone compounds and articles containing themAbandonedUS20060115516A1 (en)

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US13/622,160US8501890B2 (en)2004-11-222012-09-18Copolymerizable methine and anthraquinone compounds and articles containing them
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US20090076235A1 (en)2009-03-19
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