Copolymerizable methine and anthraquinone compounds and articles containing them
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.
1 . An intraocular lens comprising a polymer, wherein the polymer comprises at least one residue of a molecule comprising a molecular structure depicted by Formula 1a, Formula 1b, Formula 1c or Formula 1d:
wherein:
X is one or two groups selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen;
the molecule has attached thereto at least one ethylenically unsaturated polymerizable group that is not shown by Formula 1a, Formula 1b, Formula 1c or Formula 1d;
the residue comprises a reaction product of the ethylenically unsaturated polymerizable group; and
the molecule optionally comprises one or more additional atoms or moieties not shown by Formula 1a, Formula 1b, Formula 1c or Formula 1d.
2 . The intraocular lens of claim 1 , wherein the molecular structure is depicted by Formula 1a.
3 . The intraocular lens of claim 1 , wherein the molecule is depicted by Formula 1b.
4 . The intraocular lens of claim 1 , wherein the molecular structure is depicted by Formula 1c.
5 . The intraocular lens of claim 1 , wherein the molecular structure is depicted by Formula 1d.
6 . An intraocular lens comprising a polymer, wherein the polymer comprises at least one residue of a molecule comprising a molecular structure depicted by Formula II, Formula III, Formula IV, Formula V, or Formula VI:
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 and -Q; or R and R 1 are combined to make phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;
n is an integer from 1 to about 1000;
R 2 is selected from hydrogen or one or two groups selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen;
R 3 is selected from hydrogen, C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, aryl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -alkenyl and —(CHR′CHR″O—) n —R 4 , C 1 -C 12 -acyl, substituted-C 1 -C 12 -acyl, -L-Q and Q;
R 4 is selected from hydrogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkanoyl and aryl;
R′ and R″ are independently selected from hydrogen and C 1 -C 12 -alkyl;
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 —, and —(CHR′CHR″O—) n —;
Y is selected from —O-L-Q, —NR′-L-Q, —N-(L-Q) 2 , and —R 5 ;
Y 1 is selected from —O—, —S—, —SO 2 —, —N(SO 2 R 5 )—, and —N(COR 5 )—;
R 5 is C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or aryl;
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 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 of claim 6 , wherein the molecular structure is 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 and -Q; or R and R 1 are 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;
R 2 is selected from hydrogen or one or two groups selected from hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen;
R′ and R″ are independently selected from hydrogen and C 1 -C 12 -alkyl;
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 —, and —(CHR′CHR″O—) n —;
Y is selected from —O-L-Q, —NR′-L-Q, —N-(L-Q) 2 , and —R 5 ;
Y 1 is selected from —O—, —S—, —SO 2 —, —N(SO 2 R 5 )—, and —N(COR 5 )—;
R 4 is selected from hydrogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkanoyl and aryl;
R 5 is C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or aryl;
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 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 of claim 6 , the molecular structure is depicted by Formula II, wherein:
R and R 1 are independently selected from C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, and 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 and halogen;
R 1 is selected from hydrogen and C 1 -C 12 -alkyl;
L is C 1 -C 6 -alkylene-O;
Y is selected from —O-L-Q, —NR′-L-Q, and —N-(L-Q) 2 ;
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, and heteroaryl;
X 2 is —COY;
Q is:
(a) —COC(R 6 )═CH—R 7 ,
(b) —CONHCOC(R 6 )═CH—R 7 ,
(c) —CONH—C 1 -C 6 -alkylene-OCOC(R 6 )═CH—R 7 ,
(e) —COCH═CH—CO 2 R 10 ,
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 and 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.
9 . The intraocular lens of claim 6 , wherein the molecular structure is depicted by Formula II, wherein:
R and R 1 are independently selected from methyl, ethyl, —CH 2 CH 2 CN, —CH 2 CH 2 OCOCH 3 , and —CH 2 CH(CH 3 )OCOCH 3 ; or R and R 1 are combined to make thiomorpholino-S,S-dioxide;
R 2 is hydrogen;
R′ is hydrogen;
L is selected from —CH 2 CH 2 —O—, and —CH 2 CH(CH 3 )—O—;
Y is selected from —O-L-Q, —NR′-L-Q, and —N-(L-Q) 2 ;
X 1 is cyano;
X 2 is —COY; and
Q is —C(O)C(R 6 )═CHR 7 .
10 . The intraocular lens of claim 6 , wherein the molecular structure is depicted by Formula II, wherein:
R and R 1 are combined to make thiomorpholino-S,S-dioxide;
R 2 is hydrogen;
R′ is hydrogen;
L is selected from —CH 2 CH 2 —O—, and —CH 2 CH(CH 3 )—O—;
Y is selected from —O-L-Q, —NR′-L-Q, and —N-(L-Q) 2 ;
X 1 is cyano;
X 2 is —COY; and
Q —C(O)C(R 6 )═CHR 7 , wherein R 6 is methyl and R 7 is hydrogen.
11 . The intraocular lens of claim 6 , wherein the molecular structure is depicted by Formula II, wherein:
R and R 1 are each —CH 2 CH 2 —CN;
R 2 is hydrogen;
R′ is hydrogen;
L is selected from —CH 2 CH 2 —O—, and —CH 2 CH(CH 3 )—O—;
Y is selected from —O-L-Q, —NR′-L-Q, and —N-(L-Q) 2 ;
X 1 is cyano;
X 2 is —COY; and
Q is —C(O)C(R 6 )═CHR 7 , wherein R 6 is methyl and R 7 is hydrogen.
12 . An intraocular lens comprising a polymer, wherein the polymer comprises at least one residue of a molecule comprising a molecular 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.
13 . The intraocular lens of claim 6 , wherein the molecular structure is depicted by Formula III, wherein:
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 and —COY;
R 2 is hydrogen or C 1 -C 6 -alkoxy; and
R 3 is hydrogen, C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, or LQ.
14 . The intraocular lens of claim 6 , wherein:
Q is —C(O)C(R 6 )═CHR 7
wherein R 6 is methyl and R 7 is hydrogen.
15 . The intraocular lens of claim 6 , wherein the molecular structure is depicted by Formula II, 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, and —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 ) 4 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.
16 . The intraocular lens of claim 6 , wherein the molecular structure is depicted by Formula II, 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 and —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 ) 4 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 —C(O)C(R 6 )═CHR 7
wherein R 6 is methyl; and R 7 is hydrogen.
17 . The intraocular lens of claim 6 , wherein the molecular structure is depicted by Formula II, 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.
18 . The intraocular lens of claim 6 , wherein the molecular structure is depicted by Formula II, 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 —C(O)C(R 6 )═CHR 7 ;
R 6 is methyl; and
R 7 is hydrogen.
19 . A compound comprising at least one moiety having the molecular structure of Formula 1a:
wherein:
the compound has attached thereto at least one ethylenically unsaturated polymerizable group that is not shown by Formula 1a; and
the compound optionally comprises one or more additional atoms or moieties not shown by Formula 1d.
20 . A compound comprising at least one moiety having the molecular structure of Formula 1d:
wherein:
the compound has attached thereto at least one ethylenically unsaturated polymerizable group; and
the compound optionally comprises one or more additional atoms or moieties not shown by Formula 1d.
21 . A compound comprising a molecular structure depicted by Formula III, Formula IV, Formula V, or Formula VI:
wherein:
R 2 is selected from hydrogen or one or two groups selected from hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen;
R 3 is selected from hydrogen, C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, aryl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -alkenyl, —(CHR′CHR″O—) n —R 4 , C 1 -C 12 -acyl, substituted-C 1 -C 12 -acyl and -L-Q;
n is an integer selected from 1 to about 1000;
R 4 is selected from hydrogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkanoyl and aryl;
R′ and R″ are independently selected from hydrogen and C 1 -C 12 -alkyl;
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 —, and —(CHR′CHR″O—) n —;
Y is selected from —NR′-L-Q, —N-(L-Q) 2 , and —R 5 ;
Y 1 is selected from —O—, —S—, —SO 2 —, —N(SO 2 R 5 )—, and —N(COR 5 )—;
R 5 is C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or aryl;
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 and —COY;
Q is a group that includes an ethylenically-unsaturated polymerizable group;
the compound comprises at least one Q group.
22 . A compound comprising the molecular structure of Formula III, Formula IV, Formula V, or Formula VI:
wherein:
R 2 is selected from hydrogen or one or two groups selected from hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen;
R 3 is selected from hydrogen, C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, aryl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -alkenyl, —(CHR′CHR″O—) n —R 4 , C 1 -C 12 -acyl, substituted-C 1 -C 12 -acyl and -L-Q;
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 and aryl;
R′ and R″ are independently selected from hydrogen and C 1 -C 12 -alkyl;
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 —, and —(CHR′CHR″O—) n —;
Y is selected from —NR′-L-Q, —N-(L-Q) 2 , and —R 5 ;
Y 1 is selected from —O—, —S—, —SO 2 —, —N(SO 2 R 5 )—, and —N(COR 5 )—;
R 5 is C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or aryl;
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 and —COY;
Q is:
(a) —COC(R 6 )═CH—R 7 ,
(b) —CONHCOC(R 6 )═CH—R 7 ,
(c) —CONH—C 1 -C 6 -alkylene-OCOC(R 6 )═CH—R 7 ,
(e) —COCH═CH—CO 2 R 10 ,
wherein:
R 6 is hydrogen or C 1 -C 6 -alkyl;
R 7 is: hydrogen; C 1 -C 6 alkyl; phenyl or 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 and 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 form 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; and
R 11 is hydrogen, C 1 -C 6 -alkyl or aryl;
wherein the compound comprises at least one Q group.
23 . A compound comprising the molecular structure of 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 and -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 hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen;
R′ and R″ are independently selected from hydrogen and C 1 -C 12 -alkyl;
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 —, and —(CHR′CHR″O—) n —;
Y is selected from —NR′-L-Q, and —N-(L-Q) 2 ;
Y 1 is selected from —O—, —S—, —SO 2 —, —N(SO 2 R 5 )—, and —N(COR 5 )—;
R 4 is selected from hydrogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkanoyl and aryl;
R 5 is C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or aryl;
n is an integer from 1 to 100;
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, heteroaryl and —COY;
X 2 is —COY or carbamoyl;
Q is:
(a) —COC(R 6 )═CH—R 7 ,
(b) —CONHCOC(R 6 )═CH—R 7 ,
(c) —CONH—C 1 -C 6 -alkylene-OCOC(R 6 )═CH—R 7 ,
(e) —COCH═CH—CO 2 R 10 ,
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 and 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; and
R 11 is hydrogen, C 1 -C 6 -alkyl or aryl; and
the compound comprises at least one Q group.
24 . The compound of claim 23 , wherein:
R and R 1 are independently selected from C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, and aryl; or R and R 1 are combined to make cyclic structures such as phthalimido, succinimido, morpholino, thiomorpholino, pyrrolidino, piperidino, piperazino, or thiomorpholino-S,S-dioxide;
R 2 is selected from hydrogen, C 1 -C 6 alkyl and halogen;
R′ is selected from hydrogen and C 1 -C 12 -alkyl;
L is C 1 -C 6 -alkylene-O;
Y is selected from —NR′-L-Q, and —N-(L-Q) 2 ;
X 1 is cyano;
X 2 is —COY;
Q is:
or —C(O)C(R 6 )═CHR 7 ;
wherein R 6 is hydrogen or methyl, R 7 is hydrogen and R 8 and R 9 are methyl.
25 . The compound of claim 23 , 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 —, C 1 -C 6 -alkylsulfonyl, arylsulfonyl, C 1 -C 12 -acyl, substituted-C 1 -C 12 -acyl, -L-Q and -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 hydrogen;
R′ is hydrogen;
L is selected from —CH 2 CH 2 —O—, —CH 2 CH(CH 3 )—O—;
Y is selected from —NR′-L-Q, —N-(L-Q) 2 ;
X 1 is cyano;
X 2 is —COY;
n is an integer selected from 1 to 3;
Q is —C(O)C(R 6 )═CHR 7 , wherein R 6 is methyl and R 7 is hydrogen.
26 . The compound of claim 23 , wherein:
R and R 1 are independently selected from methyl, ethyl, —CH 2 CH 2 CN, —CH 2 CH 2 OCOCH 3 ; —CH 2 CH(CH 3 )OCOCH 3 ; or R and R 1 are combined to make thiomorpholino-S,S-dioxide;
R 2 is hydrogen;
R′ is hydrogen;
L is selected from —CH 2 CH 2 —O—, and —CH 2 CH(CH 3 )—O—;
Y is selected from —NR′-L-Q, and —N-(L-Q) 2 ;
X 1 is cyano;
X 2 is —COY;
Q is —C(O)C(R 6 )═CHR 7 , wherein R 6 is methyl and R 7 is hydrogen.
27 . The compound of claim 23 , wherein:
R and R 1 combined to make thiomorpholino-S,S-dioxide;
R 2 is hydrogen;
R′ is hydrogen;
L is —CH 2 CH(CH 3 )—O—;
Y is —NR′-L-Q;
X 1 is cyano;
X 2 is —COY;
Q is —C(O)C(R 6 )═CHR 7 , wherein R 6 is methyl and R 7 is hydrogen.
28 . A compound comprising a molecular structure depicted by Formula VII:
29 . The compound of claim 21 , wherein the molecular structure is depicted by Formula III, wherein:
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 and —COY;
R 2 is hydrogen or C 1 -C 6 -alkoxy; and
R 3 is hydrogen, C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, or LQ.
30 . The compound of claim 24 , wherein:
Q is —C(O)C(R 6 )═CHR 7
wherein R 6 is methyl and R 7 is hydrogen.
31 . The compound of claim 23 , 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, and —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 ) 4 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 C 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.
32 . The compound of claim 23 , 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, and —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 ) 4 —, —(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—, 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.
33 . The compound of claim 23 , 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.
34 . The compound of claim 23 , 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 —C(O)C(R 6 )═CHR 7 ;
R 6 is methyl; and
R 7 is hydrogen.
35 . A composition comprising the compound of any of claims 19 - 34 .
36 . A polymer comprising at least one residue of a molecule comprising a molecular structure depicted by Formula 1a, Formula 1b, Formula 1c or Formula 1d:
wherein:
X is one or two groups selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen;
the molecule has attached thereto at least one ethylenically unsaturated polymerizable group that is not shown by Formula 1a, Formula 1b, Formula 1c or Formula 1d;
the residue comprises a reaction product of the ethylenically unsaturated polymerizable group; and
the molecule optionally comprises one or more additional atoms or moieties not shown by Formula 1a, Formula 1b, Formula 1c or Formula 1d.
37 . A polymer comprising at least one residue of a molecule comprising a molecular structure depicted by Formula II, Formula III, Formula IV, Formula V, or Formula VI:
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 and -Q; or R and R 1 are 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;
R 2 is selected from hydrogen or one or two groups selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy and halogen;
R 3 is selected from hydrogen, C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, aryl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -alkenyl and —(CHR′CHR″O—) n —R 4 , C 1 -C 12 -acyl, substituted-C 1 -C 12 -acyl, -L-Q and Q; or R and
R 4 is selected from hydrogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkanoyl and aryl;
R′ and R″ are independently selected from hydrogen and C 1 -C 12 -alkyl;
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 —, and —(CHR′CHR″O—) n —;
Y is selected from —O-L-Q, —NR′-L-Q, —N-(L-Q) 2 , and —R 5 ;
Y 1 is selected from —O—, —S—, —SO 2 —, —N(SO 2 R 5 )—, and —N(COR 5 )—;
R 4 is selected from hydrogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkanoyl and aryl;
R 5 is C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 8 -cycloalkyl or aryl;
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 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.
38 . A composition comprising the polymer of claim 36 or claim 37 .
39 . An article comprising the polymer of claim 36 or claim 37 .
40 . A method of making a polymer, comprising copolymerizing monomers wherein the monomers comprise the compound(s) of any of claims 19 - 34 .