Copolymerizable methine and anthraquinone compounds and articles containing them

1. An intraocular lens comprising a polymer, wherein the polymer comprises at least one residue of a molecule having a structure depicted by Formula II:

wherein:

R and R 1 are independently selected from C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, aryl, heteroaryl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -alkenyl, —(CHR′CHR″O—) n —R 4 , C 1 -C 6 -alkylsulfonyl, arylsulfonyl, C 1 -C 12 -acyl, substituted-C 1 -C 12 -acyl, -L-Q or -Q; or R and R 1 are combined to make phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;

R 2 is selected from hydrogen or one or two groups selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halogen;

X 1 and X 2 are independently selected from cyano, —CO 2 C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl, arylsulfonyl, carbamoyl, C 1 -C 6 -alkanoyl, aroyl, aryl, heteroaryl or —COY;

R′ and R″ are independently selected from hydrogen or C 1 -C 12 -alkyl;

n is an integer from 1 to about 1000;

R 4 is selected from hydrogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkanoyl or aryl;

Y is selected from —O-L-Q, —NR′-L-Q, —N-(L-Q) 2 , or —R 5 ;

L is a divalent organic radical selected from C 1 -C 6 -alkylene-O—, C 1 -C 6 -alkylene-NR′—; arylene-C 1 -C 6 -alkylene-O—, arylene-C 1 -C 6 -alkylene-NR′—, arylene-O(CHR′CHR″O) n —, C 1 -C 6 -alkylene -Y 1 —(CHR′CHR″O—) n —, or —(CHR′CHR″O—) n —;

Y 1 is selected from —O—, —S—, —SO 2 —, —N(SO 2 R 5 )—, or —N(COR 5 )—;

R 5 is C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or aryl;

Q is a group that comprises an ethylenically unsaturated polymerizable group; and

the molecule comprises at least one Q group.

2. The intraocular lens of claim 1 , wherein:

R and R1 are independently selected from C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, aryl, heteroaryl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -alkenyl, —(CHR′CHR″O—) n —R 4 , C 1 -C 6 -alkylsulfonyl, arylsulfonyl, C 1 -C 12 -acyl, substituted-C 1 -C 12 -acyl, -L-Q or -Q; or R and R 1 are combined to make cyclic phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;

R 2 is selected from hydrogen or one or two groups selected from hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halogen;

X 1 and X 2 are independently selected from cyano, —CO 2 C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl, arylsulfonyl, carbamoyl, C 1 -C 6 -alkanoyl, aroyl, aryl, heteroaryl or —COY;

R′ and R″ are independently selected from hydrogen or C 1 -C 12 -alkyl;

n is an integer from 1 to about 1000;

Y is selected from —O-L-Q, —NR′-L-Q, —N-(L-Q) 2 , or —R 5 ;

L is a divalent organic radical selected from C l -C 6 -alkylene-O—, C 1 -C 6 -alkylene-NR′—; arylene-C 1 -C 6 -alkylene-O—, arylene-C 1 -C 6 -alkylene-NR′—, arylene-O(CHR′CHR″O) n —, C 1 -C 6 -alkylene -Y 1 —(CHR′CHR″-O—) n —, or —(CHR′CHR″-O—) n —;

Y 1 is selected from —O—, —S—, —SO 2 —, —N(SO 2 R 5 )—, or —N(COR 5 )—;

R 4 is selected from hydrogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkanoyl or aryl;

R 5 is C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or aryl; and

Q is a group that comprises an ethylenically unsaturated polymerizable group that does not include the alkene group in Formula II.

3. The intraocular lens of claim 1 , wherein:

R and R 1 are independently selected from C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, or aryl; or R and R 1 are combined to make phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;

R 2 is selected from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or halogen;

X 1 is selected from cyano, —CO 2 C 1—C 6 -alkyl, C 1 -C 6 -alkylsulfonyl, arylsulfonyl, carbamoyl, C 1 -C 6 -alkanoyl, aroyl, aryl, or heteroaryl;

X 2 is —COY;

R′ is selected from hydrogen or C 1 -C 12 -alkyl;

Y is selected from —O-L-Q, —NR′-L-Q, or —N-(L-Q) 2 ;

L is C 1 -C 6 -alkylene-O;

Q is:

—COC(R 6 )═CH—R 7 ,  a)

—CONHCOC(R 6 )═CH—R 7 ,  b)

—CONH—C 1 -C 6 -alkylene-OCOC(R 6 )═CH—R 7 ,  c)

—COCH═CH—CO 2 R 10 ,  e)

wherein:

R 6 is hydrogen or C 1 -C 6 -alkyl;

R 7 is: hydrogen; C 1 -C 6 alkyl; phenyl; phenyl substituted with one or more groups selected from C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, —N(C 1 -C 6 -alkyl) 2 , nitro, cyano, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkanoyloxy or halogen; 1- or 2-naphthyl; 1- or 2-naphthyl substituted with C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy; 2- or 3-thienyl; 2- or 3-thienyl substituted with C 1 -C 6 -alkyl or halogen; 2- or 3-furyl; or 2- or 3-furyl substituted with C 1 -C 6 -alkyl;

R 8 and R 9 are, independently, hydrogen, C 1 -C 6 -alkyl, or aryl; or R 8 and R 9 are combined to represent a CH 2 3-5 radical;

R 10 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 8 -alkenyl, C 3 -C 8 -cycloalkyl or aryl;

R 11 is hydrogen, C 1 -C 6 -alkyl or aryl.

4. The intraocular lens of claim 1 , wherein:

R and R 1 are independently selected from methyl, ethyl, —CH 2 CH 2 CN, —CH 2 CH 2 OCOCH 3 , or —CH 2 CH(CH 3 )OCOCH 3 ; or R and R 1 are combined to make thiomorpholino-S,S-dioxide;

R 2 is hydrogen;

X 1 is cyano;

X 2 is —COY;

Y is selected from —O-L-Q, —NR′-L-Q, or —N-(L-Q) 2 ;

R′is hydrogen;

L is selected from —CH 2 CH 2 —O—, or —CH 2 CH(CH 3 )—O—; and

Q is —C(O)C(R 6 )═CHR 7 , wherein

R 6 is hydrogen or C 1 -C 6 -alkyl; and R 7 is: hydrogen; C 1 -C 6 alkyl; phenyl; phenyl substituted with one or more groups selected from C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, —N(C 1 -C 6 -alkyl) 2 , nitro, cyano, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkanoyloxy or halogen; 1- or 2-naphthyl; 1- or 2-naphthyl substituted with C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy; 2- or 3-thienyl; 2- or 3-thienyl substituted with C 1 -C 6 -alkyl or halogen; 2- or 3-furyl; or 2- or 3-furyl substituted with C 1 -C 6 -alkyl.

5. The intraocular lens of claim 1 , wherein:

R and R 1 are combined to make thiomorpholino-S,S-dioxide;

R 2 is hydrogen;

X 1 is cyano;

X 2 is —COY;

Y is selected from —O-L-Q, —NR′-L-Q, or —N-(L-Q) 2 ;

R′is hydrogen;

L is selected from —CH 2 CH 2 —O—, or —CH 2 CH(CH 3 )—-O—; and

Q is —C(O)C(R 6 )═CHR 7 , wherein R 6 is methyl and R 7 is hydrogen.

6. The intraocular lens of claim 1 , wherein:

R and R 1 are each —CH 2 CH 2 —CN;

R 2 is hydrogen;

X 1 is cyano;

X 2 is —COY;

R′ is hydrogen;

Y is selected from —O-L-Q, —NR′-L-Q, or —N-(L-Q) 2 ;

L is selected from —CH 2 CH 2 —O—, or —CH 2 CH(CH 3 )—-O—; and

Q is —C(O)C(R 6 )═CHR 7 , wherein R 6 is methyl and R 7 is hydrogen.

7. The intraocular lens of claim 1 , wherein:

R and R 1 are independently selected from —CH 2 CH 2 CN, —CH 2 CH 2 Cl, —CH 2 CH 2 —OCO—C 1 -C 4 -alkyl, —CH 2 CH 2 OCO-aryl, —CH 2 CH 2 —OC(O) NH-aryl,

—C 1 -C 4 -alkyl, or —CH 2 C 6 H 4 CO 2 —C 1 -C 4 -alkyl; or R and R 1 are combined to make the cyclic structure thiomorpholino-S,S-dioxide;

Y is —NH-L-Q;

L is —CH 2 CH 2 O—, —CH 2 CH(CH 3 )O—, —(CH 2 ) 3 O—, —(CH 2 ) 6 O—, —CH 2 C(CH 3 ) 2 CH 2 O—, —CH 2 —C 6 H 10 —CH 2 O—, —C 6 H 4 —CH 2 CH 2 O—, —C 6 H 4 -OCH 2 CH 2 O—, or —CH 2 CH 2 (OCH 2 CH 2 ) 1-3 O—, and

Q is

wherein R 6 is methyl; R 8 and R 9 are methyl.

8. The intraocular lens of claim 1 , wherein:

R and R 1 are independently selected from —CH 2 CH 2 CN, —CH 2 CH 2 C1, —CH 2 CH 2 —OCO—C 1 -C 4 -alkyl, —CH 2 CH 2 OCO-aryl, —CH 2 CH 2 —OC(O)NH-aryl,

—C 1 -C 4 -alkyl or —CH 2 C 6 H 4 CO 2 —C 1 -C 4 -alkyl; or R and R 1 are combined to make the cyclic structure thiomorpholino-S,S-dioxide;

Y is —NH-L-Q;

L is —CH 2 CH 2 O—, —CH2CH(CH 3 )O, —(CH 2 ) 3 O—, —(CH 2 ) 4 O—, —(CH 2 ) 6 O—, —CH 2 C(CH 3 ) 2 CH 2 —, —CH 2 —C 6 H 10 —CH 2 O—, —C 6 H 4 —CH 2 CH 2 O—, —C 6 H 4 —OCH 2 CH 2 O—, or —CH 2 CH 2 (OCH 2 CH 2 ) 1-3 O—; and

Q is —C(O)C(R 6 )═CHR 7

wherein R 6 is methyl; and R 7 is hydrogen.

9. The intraocular lens of claim 1 , wherein:

R is —CH 2 CH 2 CN;

R 1 is —CH 2 CH 2 CN, —CH 2 CH 2 Cl, —CH 2 CH 2 OCO—C 1 -C 4 -alkyl,

Y is —NH-L-Q;

L is —CH 2 CH 2 O—or —CH 2 CH(CH 3 )O—; and

Q is

wherein R 6 , R 8 and R 9 are methyl.

10. The intraocular lens of claim 1 , wherein:

R is —CH 2 CH 2 CN;

R 1 is —CH 2 CH 2 CN, —CH 2 CH 2 C1, —CH 2 CH 2 OCO—C 1 -C 4 -alkyl,

Y is —NH-L-Q;

L is —CH 2 CH 2 O—or —CH 2 CH(CH 3 )O—; and

Q is —C(O)C(R 6 )═CHR 7 ;

R 6 is methyl; and

R 7 is hydrogen.

11. An intraocular lens comprising a polymer, wherein the polymer comprises at least one residue of a molecule having a structure depicted by Formula VII:

wherein the residue is bonded to the polymer at a location depicted as a terminal ethene group in Formula VII.