Claims
- 1. A process of making alpha-methylstyrene dimer derivatives represented by the formula wherein R1, R2, R3, R4, R5 and R6 are each independently selected from group consisting of hydrogen, —CH(O), —CN, isocyanato, thioisocyanato, SO3H and salts and esters thereof, NR7R8, a silane, a halogen, —C(O)OR9, —C(O)NR10R11, —CR12(O), —C(O)OC(O)R13, —C(O)NR14COR15, —OC(O)R16, —OR17, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, and substituted and unsubstituted aryl; R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 are each independently selected from the group consisting of H, alkyl, aryl, substituted alkyl or substituted aryl; R17 is selected from the group consisting of alkyl, aryl, substituted alkyl or substituted aryl; R1, R2, R3, R4, R5 and R6 cannot all simultaneously be hydrogen; and the alkyl and the substituted alkyls have a chain consisting of 1 to 12 carbons comprising the steps of:a) adding a cobalt chain transfer catalyst, a free-radical initiator and an alpha-methylstyrene monomer containing at least one functional group, in an inert atmosphere, to form a mixture; b) heating the mixture to a temperature in the range of 60° C. to 140° C.; and c) forming alpha-methylstyrene dimer derivatives containing intact functional groups and having less than 0.1% by weight of 2,4-diphenyl-4-methyl-2-pentene.
- 2. The process according to claim 1, wherein the free-radical initiator is selected from the group consisting of azcumene; 2,2′-azobis(2-methyl)-butanenitrile; 2,2′-azobis(isobutyronitrile)(AIBN); 4,4′-azobis(4-cyanovaleric acid); 2-(t-butylazo)-2-cyanopropane; 1,1′-azobis(cyclohexane-1-carbonitrile), and combinations thereof.
- 3. The process according to claim 1, wherein the cobalt chain transfer catalyst is selected from the group consisting of cobalt (II) and cobalt (III) chelates and combinations thereof.
- 4. The process according to claim 3, wherein the cobalt chain transfer catalyst comprises the general structure wherein Z is selected from the group consisting of hydrogen and BR20R21, where R20 and R21 are each independently selected from the group consisting of unsubstituted and substituted aryl, unsubstituted and substituted C1-C12 alkyl, unsubstituted and substituted C1-C12 alkoxy, unsubstituted and substituted aryloxy, and a halogen; J and K are each independently selected from the group consisting of phenyl, substituted phenyl, methyl, ethyl, and —(CH2)4—; and L is selected from the group consisting of water, an amine, an ammonia, a phosphine and combinations thereof.
- 5. The process according to claim 4 wherein Z is BF2.
- 6. The process according to claim 3, wherein the cobalt chain transfer catalyst comprises the general structure wherein Z is selected from the group consisting of hydrogen and BR20R21, where R20 and R21 are each independently selected from the group consisting of unsubstituted and substituted aryl, unsubstituted and substituted C1-C12 alkyl, unsubstituted and substituted C1-C12 alkoxy, unsubstituted and substituted aryloxy, and a halogen; J and K are each independently selected from the group consisting of phenyl, substituted phenyl, methyl, ethyl, and —(CH2)4—; and L is selected from the group consisting of water, an amine, an ammonia, a phosphine and combinations thereof; and Q is an organic radical.
- 7. The process according to claim 6 wherein Z is BF2.
- 8. The process according to claim 1, wherein the mixture of step b) is heated for at least 5 minutes.
- 9. The process according to claim 1, wherein the mixture of step b) is heated for approximately 10 hours to approximately 10 days.
- 10. The process according to claim 1, wherein the mixture of step b) is heated to a temperature in the range of 80° C. to 100° C.
- 11. The process according to claim 1, wherein step a solvent is added with the cobalt catalyst, the free radical initiator and the alpha-methylstyrene monomer to form a mixture.
- 12. A new process of making alpha-methylstyrene dimer derivatives represented by the formula wherein R1, R2, R3, R4, R5 and R6 are each independently selected from group consisting of hydrogen, —CH(O), —CN, isocyanato, thioisocyanato, SO3H and salts and esters thereof, NR7R8, a silane, a halogen, —C(O)OR9, —C(O)NR10R11, —CR12(O), —C(O)OC(O)R13, —C(O)NR14COR15, —OC(O)R16, —OR17, substituted and unsubstituted alkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, and substituted and unsubstituted aryl; R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 are each independently selected from the group consisting of H, alkyl, aryl, substituted alkyl or substituted aryl; R17 is selected from the group consisting of alkyl, aryl, substituted alkyl or substituted aryl; R1, R2, R3, R4, R5 and R6 cannot all simultaneously be hydrogen; and the alkyl and the substituted alkyls have a chain consisting of 1 to 12 carbons comprising the steps of:a) adding a cobalt chain transfer catalyst, a free-radical initiator and an alpha-methylstyrene monomer containing at least one functional group, in an inert atmosphere, to form a mixture; b) initiating polymerization with an external source comprising ultraviolet light, visible light, electron beam or combinations thereof; and c) forming alpha-methylstyrene dimers containing intact functional groups and having less than 0.1% by weight of 2,4-diphenyl-4-methyl-2-pentene.
CROSS REFERENCE TO RELATED APPLICATION
This application is a divisional of application Ser. No. 09/245,521, filed Feb. 5, 1999 now U.S. Pat. No. 6,294,708. This application claims the benefit of 60/074,322 filed on Feb. 11, 1998.
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