Patent GB-882147-A (GB)
Title: Novel aliphatic carboxylic acid esters
Inventor: GREENSPAN FRANK PHILIP
IPC: C08G59/34
Filed: 1959-12-22
Abstract: Coating compositions comprise an ester of an epoxidized polycyclopentadiene or epoxided alkylcyclopentadiene having 3 to 6 cyclopentadiene units and an average of 1 to 2 epoxy groups in the molecule with a saturated or unsaturated mono- or poly-aliphatic carboxylic acid (see Groups IV(a) and IV(b)).  In examples: glass, tin and steel sheet are coated with compositions containing such esters derived from stearic acid, oleic acid or blends of polymerized C18 unsaturated fatty acid with dehydrated castor oil acid together with a melamine-formaldehyde resin and, in some cases, manganese octoate, air dried and baked. In another example glass, tin and steel sheets are coated with a solution of an ester of an epoxidized cyclopentadiene with a blend of polymerized C18 unsaturated fatty acids and soya fatty acids containing cobalt, manganese and lead naphthenates and air dried.ALSO:The invention comprises esters of epoxidized polycyclopentadienes or epoxidized alkyl substituted polycyclopentadienes and aliphatic carboxylic acids, said polycyclopentadiene having 3 to 6 cyclopentadiene units and an epoxy functionality of 2 to 4 (i.e. containing an average of 1 to 2 epoxy groups in the molecule).  The esters are prepared by reacting the epoxidized polycyclopentadiene and the acid at elevated temperatures. Generally 1 to 7 parts by weight of acid are used per part of epoxy compound.  An inert atmosphere may be used and a catalyst such as LiOH, trimethylbenzylammonium hydroxide or (CH3)3NHOH may be present. Suitable aliphatic carboxylic acids include saturated and unsaturated fatty acids, preferably having 4 to 24 carbon atoms and polycarboxylic acids such as maleic acid or polymerized fatty acids. Part of the epoxidized polycyclopentadiene may be replaced by polyhydroxy compounds or by other polyepoxy compounds reactive with the acids.  The products may contain free hydroxy groups.  Esters with drying oil fatty acids harden on exposure to air to hard, tough, alkali-resistant coatings.  The present esters may be blended with resins such as phenol or amine aldehyde resins, alkyd resins or resin gums, or with drying or semi-drying oils.  Plasticizers, pigments and dyes may be present.ALSO:The invention comprises esters of epoxidised polycyclopentadienes or epoxidised alkyl substituted polycyclopentadienes and aliphatic carboxylic acids, said polycyclopentadiene having 3 to 6 cyclopentadiene units and an epoxy functionality of 2 to 4 (i.e. containing an average of 1 to 2 epoxy groups in the molecule).  The esters are prepared by reacting the epoxidised polycyclopentadiene and the acid at elevated temperatures. Generally 1 to 7 parts by weight of acid are used per part of epoxy compound.  An inert atmosphere may be used and a catalyst such as LiOH, trimethylbenzylammonium hydroxide or (CH3)3 NHOH may be present.  Suitable aliphatic carboxylic acids include saturated and unsaturated fatty acids, preferably having 4 to 24 carbon atoms and polycarboxylic acids such as maleic acid or polymerised fatty acids. Part of the epoxidised polycyclopentadiene may be replaced by polyhydroxy compounds or by other polyepoxy compounds reactive with the acids.  The products may contain free hydroxy groups.  The epoxy compounds are prepared by reacting the polycyclopentadiene with an epoxidising agent, preferably a lower aliphatic peracid.  The peracid may be preformed or formed in situ from hydrogen peroxide and the corresponding carboxylic acid.  A solvent may be present.