Ethynyl adamantane derivatives and methods of polymerization thereof
US5017734A · kind A · utility
Inventors
Key dates
| Filing date | Dec 11, 1989 |
| Grant date | May 21, 1991 |
| Priority date | — |
| Expiry date | Dec 11, 2009 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2603/90
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
1,3-Diethynyl-5,7-dimethyladamantane; 1,3,5-triethynyladamantane; 3,3'-diethynyl-1,1'-biadamantane; 1-ethynyldiamantane; 1,4-diethynyldiamantane; 1,6-diethynyldiamantane and 4,9-diethynyldiamantane as new compositions of matter, and a method of forming them in which adamantane; 1,3-dimethyladamatane; 1-hydroxy-3,5-dimethyladamantane; 1,1'-biadamantane and diamantane are each brominated to form a bromo derivative thereof; the bromo derivative is reacted with vinyl bromide in the presence of a Friedel-Crafts catalyst to convert it to its corresponding 2,2-dibromoethyl derivative and the 2,2-dibromoethyl derivative is subjected to dehydrohalogenation to convert it to its final ethynyl form. The 1,3-diethynyl-5,7-dimethyladamantane; 1,3,5-triethynyladamantane; 3,3'-diethynyl-1,1'-biadamantane; 1,4-diethynyldiamantane; 1,6-diethynyldiamantane and 4,9-diethynyldiamantane can be heat cured to form homopolymers having useful commercial properties. 1,3-Diethynyl-5,7-dimethyladamantane; 1,3,5-triethynyladamantane; 1,4-diethynyldiamantane; 1,6-diethynyldiamantane and 4,9-diethynyldiamantane can be polymerized in the presence of a suitable metal or peroxide catalyst.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.