Cure-indicating molding and coating composition

A curable composition, comprising:

• an ethylenically unsaturated compound having more than one ethylenically unsaturated group;
• a crosslinker compound containing a multiplicity of SiH groups;
• a catalyst capable of catalyzing a hydrosilation reaction;
• and a cure-indicating dye that exhibits a color change in a dye evaluation test, at 25.degree. C. when 500 mg of said dye, about 500 ml of dichloromethane, 100 ml of pentamethyldisiloxane, and 10 ml of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together,
• wherein said dye is represented by the formula ##STR39## wherein X.sup.4 is N--R.sup.67 R.sup.68, O--R.sup.69, S--R.sup.70 or CR.sup.71 R.sup.72 R.sup.73 and wherein each of R.sup.58, R.sup.59, R.sup.60, R.sup.61, R.sup.62, R.sup.63, R.sup.64, R.sup.65, R.sup.66, is independently selected from the group consisting of hydrogen, halogen, a hydrocarbyl group optionally interrupted with one or more heteroatoms and an acyclic, alicyclic or aromatic heterocyclic group, and each of R.sup.67, R.sup.68, R.sup.69, R.sup.70, R.sup.71, R.sup.72, and R.sup.73 is independently selected from the group consisting of hydrogen, a hydrocarbyl group optionally interrupted with one or more heteroatoms and an acyclic, alicyclic or aromatic heterocyclic group.

A curable composition, comprising:

• an ethylenically unsaturated compound having more than one ethylenically unsaturated group;
• a crosslinker compound containing a multiplicity of SiH groups;
• a catalyst capable of catalyzing a hydrosilation reaction;
• and
• a cure-indicating dye that exhibits a color change in a dye evaluation test, at 25.degree. C. when 500 mg of said dye, about 500 ml of dichloromethane, 100 ml of pentamethyldisiloxane, and 10 ml of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together, wherein said dye is selected from compounds of the formula ##STR40##

A curable composition, comprising:

• a compound having more than one ethylenically unsaturated group;
• a crosslinker compound containing a multiplicity of SiH groups;
• a catalyst capable of catalyzing a hydrosilation reaction;
• and
• a cure-indicating dye that exhibits a color change, in a dye evaluation test, at 25.degree. C. when 500 .mu.g of said dye, about 500 .mu.l of dichloromethane, 100 .mu.l of pentamethyldisiloxane, and 10 .mu.l of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together.

A curable composition, comprising:

• an ethylenic compound comprising a silicone backbone having two or more vinyl functional groups;
• a crosslinker compound comprising at least two SiH groups and being selected from the group consisting of organohydrosilanes, organohydrocyclopolysiloxanes, organohydropolysiloxanes, and branched organohydropolysiloxanes;
• a catalyst capable of catalyzing a hydrosilation reaction, wherein said catalyst comprises a complex of platinum and a vinylsiloxane and wherein said composition comprises a molar ratio of platinum to vinyl functional groups between 1:2 and 1:1,000;
• and
• a cure-indicating dye that exhibits a color change within about 10 minutes at 25.degree. C. when 500 mg of said dye, about 500 ml of dichloromethane, 100 ml of pentamethyldisiloxane, and 10 ml of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together, wherein said cure-indicating dye is selected from the group consisting of indoaniline dyes, indophenol dyes, quinone monoimine dyes, quinone diimine dyes, cyanine dyes, merocyanine dyes, cyclohexadieneone dyes, iminocyclohexadieneone dyes, imidazolylidinecyclohexadienone dyes, dihydronaphthalenone dyes, iminodihydronaphthalenone dyes, imidazolylidinedihydronaphthalenone dyes, cyclohexadienimine dyes, aryl substituted bis (trifluoromethylsulf-onyl)hexatrienyl dyes, aryl substituted bis (trifluoromethylsulfonyl)butadienyl dyes, aryl substituted bis (fluorosulfonyl)hexatrienyl dyes, aryl substituted bis (fluorosulfonyl)butadienyl dyes, oxazolone dyes, cationic dyes, anionic oxonol dyes and betaine dyes.

A curable composition, comprising:

• an ethylenic compound comprising a silicone backbone having two or more vinyl functional groups;
• a crosslinker compound comprising at least two SiH groups and being selected from the group consisting of organohydrosilanes, organohydrocyclopolysiloxanes, organohydropolysiloxanes, and branched organohydropolysiloxanes;
• a catalyst capable of catalyzing a hydrosilation reaction, wherein said catalyst comprises platinum and wherein said composition comprises a molar ratio of platinum to functional groups between 1:2 and 1:1,000;
• and
• a cure-indicating dye that exhibits a color change within about 10 minutes at 25.degree. C. when 500 mg of said dye, about 500 ml of dichloromethane, 100 ml of pentamethyldisiloxane, and 10 ml of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together, wherein said cure-indicating dye is selected from the group consisting of:
• neutral dyes represented by the following general formula:
• ##STR53## wherein:
• each R.sup.1, R.sup.2, R.sup.3, and R.sup.4 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, carboxamide (--C(O)NR.sup.1 R.sup.2), and wherein R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 may be connected to form a ring;
• A is O or NR.sup.22, wherein
• R.sup.22 is a group selected from the group consisting of:
• hydrogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.6 -C.sub.18 arylamino, and substituted sulfonyl;
• and
• B is any group capable of providing extended conjugation thereby rendering the dye capable of absorbing visible, near-UV, or near-infrared radiation including groups of formula D, E, F, H, or J, wherein
• D is represented by formula:
• ##STR54## wherein:
• each R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, morpholino, and alkylamido and wherein any two adjacent R.sup.5, R.sup.6, R.sup.7, R.sup.8, and R.sup.9 groups may be connected to form a ring;
• E is represented by formula:
• ##STR55## wherein:
• X.sup.1 is S or O;
• X.sup.2 is C(R.sup.12).sub.2 or NR.sup.12 ;
• and
• each R.sup.10, R.sup.11 and R.sup.12 group is independently selected from the group consisting of:
• hydrogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, and wherein R.sup.10 and R.sup.11 may be connected to form a ring;
• F is represented by formula:
• ##STR56## wherein:
• X.sup.3 is N or CR.sup.16 ;
• and
• each R.sup.13, R.sup.14, R.sup.15, and R.sup.16 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino and wherein any two adjacent R.sup.13, R.sup.14, R.sup.15, and R.sup.16 groups may be connected to form a ring;
• H is represented by formula:
• ##STR57## wherein:
• each R.sup.20 and R.sup.21 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, morpholino, and furyl and wherein R.sup.20 and R.sup.21 may be connected to form a ring;
• and
• J is represented by formula:
• ##STR58## wherein:
• each R.sup.5, R.sup.6, R.sup.7 and R.sup.8 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, morpholino, alkylamido and wherein R.sup.5 and R.sup.6 or R.sup.7 and R.sup.8 may be connected to form a ring;
• and
• R.sup.23 is a group selected from the group consisting of:
• hydrogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.8 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, and substituted sulfonyl;
• sulfonyl dyes represented by the following general formula:
• ##STR59## wherein:
• each R.sup.24 and R.sup.25 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino with the proviso that at least one of R.sup.24 and R.sup.25 is or contains a substituted aryl, aminoaryl or heterocyclic group;
• each R.sup.26 and R.sup.27 group is independently selected from the group consisting of:
• F and CF.sub.3 ;
• and
• n is 0 to 3;
• neutral dyes represented by the following general formula:
• ##STR60## wherein:
• each R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.29 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.8 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, carboxamide (--C(O)NR.sup.1 R.sup.2), and wherein any two adjacent R.sup.1, R.sup.2, R.sup.3, R.sup.4, or R.sup.29 groups may be connected to form a ring;
• R.sup.30 is a group selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino;
• and
• n is 1 or 2;
• anionic oxonol dyes having the following general formula:
• ##STR61## wherein:
• Z represents the non-metallic atoms necessary to complete a substituted or unsubstituted nitrogen-containing heterocyclic ring,
• each R.sup.28 is independently selected from the group consisting of:
• hydrogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.6 -C.sub.18 aminoaryl;
• n is 1 or 2;
• and wherein
• M+ is selected from any suitable cation;
• cationic dyes having the following general formula:
• ##STR62## wherein:
• each R.sup.31, R.sup.32, R.sup.33, and R.sup.34 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, carboxamide (--C(O)NR.sup.1 R.sup.2), and wherein any two adjacent R.sup.31, R.sup.32, R.sup.33, or R.sup.34 groups may be connected to form a ring;
• R.sup.35 and R.sup.36 are as defined above for R.sup.33 and R.sup.34 ;
• X is O or NR.sup.37 ;
• Y is N or CR.sup.38 ;
• R.sup.37 and R.sup.38 are as defined above for R.sup.33 ;
• and wherein
• M- is any suitable anion;
• cationic dyes having the following general formula:
• ##STR63## wherein:
• each R.sup.31, R.sup.32, R.sup.33, and R.sup.34 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, carboxamide (--C(O)NR.sup.1 R.sup.2), and wherein any two adjacent R.sup.31, R.sup.32, R.sup.33, or R.sup.34 groups may be connected to form a ring;
• each R.sup.39 is independently selected from the group consisting of:
• hydrogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino;
• R.sup.40 is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino, and carboxamide;
• X is C.dbd.R.sup.48, C(R.sup.38).sub.2 or S, wherein
• R.sup.38 is as defined above for R.sup.40 ;
• R.sup.48 is an oxo group, a divalent hydrocarbyl-containing group, or a divalent heterocyclic group;
• and wherein R.sup.48 and R.sup.34 may be connected to form an unsaturated ring;
• and wherein
• M- is any suitable anion;
• cationic dyes having the following general formula:
• ##STR64## wherein:
• each R.sup.42 to R.sup.45 group is independently selected from the group consisting of:
• hydrogen, halogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.1 -C.sub.20 alkoxy, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino;
• each R.sup.40, R.sup.41, R.sup.46 and R.sup.47 group is independently selected from the group consisting of:
• hydrogen, a C.sub.1 -C.sub.20 alkyl, a C.sub.3 -C.sub.18 cycloalkyl, a C.sub.6 -C.sub.18 aryl, a C.sub.6 -C.sub.18 aryloxy, a C.sub.6 -C.sub.18 hydroxyaryl, a C.sub.6 -C.sub.18 arylcarboxy, a C.sub.6 -C.sub.18 carboxyaryl, a C.sub.2 -C.sub.18 alkenyl, a C.sub.1 -C.sub.20 alkylamino, a C.sub.6 -C.sub.18 arylamino, a C.sub.6 -C.sub.18 aminoaryl, a C.sub.2 -C.sub.20 di(hydrocarbyl)amino and wherein any two adjacent R.sup.41 to R.sup.43 and R.sup.44 to R.sup.46 groups may be connected to form a ring;
• n is 1 or 2;
• and wherein
• M- is any suitable anion.

A curable composition, comprising:

• an ethylenic compound comprising a silicone backbone having two or more vinyl functional groups;
• a crosslinker compound comprising at least two SiH groups and being selected from the group consisting of organohydrosilanes, organohydrocyclopolysiloxanes, organohydropolysiloxanes, and branched organohydropolysiloxanes, wherein said composition comprises a ratio of SiH groups to functional groups between 1:1 and 10:1;
• a catalyst capable of catalyzing a hydrosilation reaction, wherein said catalyst comprises platinum and wherein said composition comprises a ratio of platinum to functional groups between 1:2 and 1:1,000;
• and
• a cure-indicating dye selected from the group consisting of 4-[[4-(Dimethylamino)phenyl]imino]-2,5-cyclohexadien-1-one;
• 2-Chloro-4-[[2-methyl-4-(diethylamino)phenyl]imino]-2,5-cyclohexadien-1-on e;
• 4-[[4-(Diethylamino)phenyl]imino]-1,4-dihydronaphthalen-1-one;
• 4-[[4-(Dimethylamino)phenyl]imino]-1,4-dihydronaphthalen-1-one;
• 4-[[2-methyl-4-(diethylamino)phenyl]imino]-1,4-dihydronaphthalen-1-one;
• 3-Methoxy-4-[[2-methyl-4-(diethylamino)phenyl]imino]-2,5-cyclohexadien-1-o ne;
• 2-Methyl-4-[[4-(4-morpholinyl)phenyl]imino]-2,5-cyclohexadien-1-one;
• 2,5-Dichloro-4-[[4-(diethylamino)phenyl]imino]-2,5-cyclohexadien-1-one;
• 3-[[4-(Diethylamino)-2-methylphenyl]imino]-6-oxo-N-phenyl-1,4-cyclohexadie ne-1-carboxamide;
• 5-[[4-(Diethylamino)-2-methylphenyl]imino]-8-(5H)-quinolinone;
• 2,6-Dichloro-4-[[4-(acetamido)phenyl]imino]-2,5-cyclohexadien-1-one;
• 4-(1-naphthylimino)-2,5-cyclohexadien-1-one;
• 4-(2-naphthylimino)-2,5-cyclohexadien-1-one;
• 2,5-Bis(phenylamino)-4(phenylimino)-2,5-cyclohexadien-1-one;
• 4-[5,5-Bis[(trifluoromethyl)sulfonyl]-2,4-pentadienylidene]-1,4-dihydro-1- methylquinoline;
• 6,6-Bis[4-(dimethylamino)phenyl]1,3,5-hexatriene-1,1-bis(sulfonylfluoride) ;
• 4-[4,4-Bis[(trifluoromethyl)sulfonyl]-1,3-butadienyl]-N,N-dimethylbenzena mine;
• and 4-[3-[4-(Dimethylamino)phenyl]-2-propenylidene]-2-phenyl-5(4H)-oxazolone.

A silicone composition comprising:

• a curable silicone polymer containing at least two functional groups capable of reacting with a SiH group in the presence of a catalyst;
• a crosslinker compound containing at least two SiH groups;
• a hydrosilation catalyst;
• and
• one or more cure-indicating dyes that exhibit a color change within about 10 minutes at 25.degree. C. when 500 mg of said dye, about 500 ml of dichloromethane, 100 ml of pentamethyldisiloxane, and 10 ml of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together.

A silicone composition comprising:

• a curable silicone polymer containing between 1 and 5,000 dimethyl siloxy bridging groups and at least two vinyl groups;
• a crosslinker compound containing at least two SiH groups and selected from the group consisting of organohydrosilanes, organohydrocyclopolysiloxanes, organohydropolysiloxanes, and branched organohydropolysiloxanes;
• a hydrosilation catalyst, wherein said catalyst comprises platinum and wherein said composition comprises a ratio of platinum to functional groups between 1:2 and 1:1,000;
• and
• one or more cure-indicating dyes that exhibit a color change within about 10 minutes at 25.degree. C. when 500 mg of said dye, about 500 ml of dichloromethane, 100 ml of pentamethyldisiloxane, and 10 ml of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together, wherein said composition comprises a ratio of SiH groups to functional groups between 1.3:1 and 4:1, and wherein said silicone composition exhibits a color change upon curing of at least 10 .DELTA.E* units.

A method of monitoring the curing of a curable composition, comprising the steps of:

• mixing a compound having two or more ethylenic functional groups;
• a crosslinker compound containing at least 2 SiH groups;
• a hydrosilation catalyst;
• and a cure-indicating dye that exhibits a color change, in a dye evaluation test, within about 10 minutes at 25.degree. C. when 500 mg of said dye, about 500 ml of dichloromethane, 100 ml of pentamethyldisiloxane, and 10 ml of a hydrosilation catalyst solution having between about 2 and 3 weight percent platinum are mixed together;
• and
• observing said composition, wherein said composition has a first color before the cure reaction is effected and a second color after the cure reaction has been effected and wherein said first and second colors differ by at least 5 .DELTA.E* units.