Patent GB-1086355-A (GB)
Title: Decorative fire retardant paints
IPC: C07F9/6574
Filed: 1964-08-04
Abstract: A fine retardant paint comprises a vehicle component, an inert pigment and a fire retardant pigment selected from the group consisting of (a) bis(pentachlorocyclopentadienyl), (b) 2,21,-3,31,4,41,5,51,7,7,71,71 - dodecachloro - 1,1,6,6,- 61,61 - hexahydro - 2,5 - methano - 21,51 - methanobiphenyl, (c) compounds having the formula <FORM:1086355/C4-C5/1> wherein Z is selected from Cl2, O, (OH)2.xH2O, S, <FORM:1086355/C4-C5/2> and (OH)[NH(R4)3]+, <FORM:1086355/C4-C5/3> <FORM:1086355/C4-C5/4> <FORM:1086355/C4-C5/5> and (g) mixtures thereof, wherein R is H, alkyl, substituted alkyl, aryl, or substituted aryl, R1 is H, alkyl, substituted alkyl, aryl, substituted aryl, amino, substituted amino, alkoxy or aryl-alkoxy, or R and R1 conjoined are alkylene, sub stituted alkylene aryl or substituted amino, Y is S or O, R2 and R3 are H, alkyl, substituted alkyl (in which the substituents are halogen, alkyl, alkoxy, aryloxy, furyl, tetrahydrofuryl, alkyl-mercapto, arylmercapto, or alkenyl) aryl, substituted aryl (in which the substituents are as for substituted alkyl), or R2 and R3 conjoined are alkylene, substituted alkylene (in which the substituents are nitro or as for substituted alkyl), phenylene or substituted phenylene (in which the substituents are nitro or as for substituted alkyl), each R4 is independently selected from H, alkyl, or monohydroxyalkyl, each R5 is C2 to C6 alkylene, and x is 0 or an integer from 1 to 5.  The vehicle may be linseed oil, oleo-resin, polyamide resin, phenolic resin, epoxy resin, alkyd resin, linseed oil derivatives capable of being thinned by water, latices of polyvinyl alcohol or acetate, styrene-butadiene copolymers or polyacrylic polymers.ALSO:A fire retardant paint comprises a vehicle component, an inert pigment and a fire retardant pigment selected from the group consisting of (a) bis - (pentachlorocyclopentadienyl), (b) 2,21,3,31,4,41,5,51,7,7,71,71 - dodecachloro - 1,1, 6,6,61,61 - hexahydro - 2,5 - methano - 21,51-methanobiphenyl, (c) compounds having the formula <FORM:1086355/C3/1> wherein Z is selected from Cl2, O, (OH)2.xH2O, S, <FORM:1086355/C3/2> <FORM:1086355/C3/3> and (OH)[NH(R4)3]+ <FORM:1086355/C3/4> <FORM:1086355/C3/5> <FORM:1086355/C3/6> and (g) mixtures thereof, wherein R is H, alkyl, substituted alkyl, aryl, or substituted aryl, R1 is H, alkyl, substituted alkyl, aryl, substituted aryl, amino, substituted amino, alkoxy or arylalkoxy, or R and R1 conjoined are alkylene, substituted alkylene aryl or substituted amino, Y is S or O, R2 and R3 are H, alkyl, substituted alkyl (in which the substituents are halogen, alkyl, alkoxy, aryloxy, furyl, tetrahydrofuryl, alkylmercapto, arylmercapto, or alkenyl) aryl, substituted aryl (in which the substituents are as for substituted alkyl), or R2 and R3 conjoined are alkylene, substituted alkylene (in which the substituents are nitro or as for substituted alkyl), phenylene or substituted phenylene (in which the substituents are nitro or as for substituted alkyl), each R4 is independently selected from H, alkyl, or monohydroxyalkyl, each R5 is C2 to C6 alkylene, and x is 0 or an integer from 1 to 5.  The vehicle may be linseed oil, oleoresin, polyamide resin, phenolic resin, epoxy resin, alkyd resin, linseed oil derivatives capable of being thinned by water, latices of polyvinyl alcohol or acetate, styrene-butadiene copolymers or polyacrylic polymers.ALSO:Compounds having the formula <FORM:1086355/C2/1> where Z is selected from the group(s) consisting of Cl2, O, (OH)2.xH2O, S, <FORM:1086355/C2/2> and <FORM:1086355/C2/3> R is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl and substituted aryl; R1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, amino, substituted amino, alkoxy and aryl alkoxy; R and R1 conjoined are selected from alkylene, substituted alkylene, substituted aryl and substituted amino groups; Y is selected from the group consisting of O and S; R2 and R3 are selected from the group consisting of hydrogen; alkyl; substituted alkyl, in which the substituents are defined as halogen, alkyl, alkoxy, aryloxy, furyl, tetrahydrofuryl, alkylmercapto, arylmercapto and alkenyl groups; aryl; substituted aryl in which the substituents are defined as halogen, alkyl, alkoxy, aryloxy, furyl, tetrahydrofuryl, alkylmercapto, arylmercapto, and alkenyl groups; R2 and R3 when conjoined are defined as alkylene and substituted alkylene in which the substituents are defined as halogen, alkyl, nitro, alkyloxy, aryloxy, furyl, tetrahydrofuryl, alkylmercapto, arylmercapto and alkenyl groups; phenylene and substituted phenylene in which the substituents are as defined for substituted alkylene; each R4 expression is independently selected from the group consisting of hydrogen, alkyl and monohydroxyalkyl; each R5 is an alkylene group having from 2 to 6 carbon atoms; and x is an integer from zero to 5. The formula given above without the Z group is hereinafter referred to as C10Cl10. C10Cl10O may be prepared by reacting a hexachlorocyclopentadiene-chlorosulphonic acid reaction product with alcoholic alkali followed by acidification.  This ketone may be hydrolysed with water to yield a compound wherein the Z term is (OH)2 or (OH)2.H2O or (OH)2.xH2O. Compounds wherein the Z term is <FORM:1086355/C2/4> may be prepared by heating the said chlorosulphonic acid reaction product with an amide or thioamide. Many suitable amides are specified. Compounds where the Z term of the generic formula is <FORM:1086355/C2/5> may be prepared by reacting C10Cl10O with phosphorous acid or mono- or di-esters of phosphorous acid.  Many examples of such esters are given.  These phosphonates are prepared by mixing the two reactants, preferably in 1 : 1 molar ratio, or with an excess of phosphite and warming if necessary to complete the reaction.  Many phosphonates are listed in the Specification. Amine salts may be prepared by reacting the C10Cl10 hydrates with an amine such as triethanolamine, ethylenediamine, diethylamine, diethylene triamine, tetraethylenediamine, hexamethylenetetramine, butylamine, morpholine, pyridine or aminophenylamine. In examples, (32) C10Cl10O is reacted with water at room temperature to form a hydrate; (33) this hydrate dissolved in acetone is refluxed with triethanolamine and allowed to cool, whereupon the amine salt precipitated; (34) C10Cl10O and glycerol dissolved in carbon tetrachloride were refluxed in order to form a glycerol derivative; (35) C10Cl10O and ethylenediamine were refluxed in aqueous methanol and cooled whereupon the ethylenediamine derivative precipitated.  The compound <FORM:1086355/C2/6> is prepared by condensing two moles of hexachlorocyclopentadiene with one mole of butadiene. The compound bis(pentachlorocyclopentadienyl) is prepared by the dechlorination of hexachlorocyclopentadiene.ALSO:A fire retardant paint comprises a vehicle component, an inert pigment and a fire retardant pigment selected from the group consisting of (a) bis(pentachlorocyclopentadienyl), (b) 2,21, 3,31, 4,41, 5,51, 7,7,71,71, -dodecachloro- 1,1, 6,6,61,61-hexahydro-2, 5-methano-21,51,-methanobiphenyl, (c) compounds having the formula:- <FORM:1086355/B1-B2/1> wherein Z is selected from Cl2,O, (OH)2.xH2O, S, <FORM:1086355/B1-B2/2> and <FORM:1086355/B1-B2/3> and (g) mixtures thereof, wherein R is H, alkyl, substituted alkyl, aryl, or substituted aryl, R1 is H, alkyl, substituted alkyl, aryl, substituted aryl, amino, substituted amino, alkoxy or arylalkoxy, or R and R1 conjoined are alkylene, substituted alkylene aryl or substituted amino, Y is S or O, R2 and R3 are H, alkyl, substituted alkyl (in which the substituents are halogen, alkyl, alkoxy, aryloxy, furyl, tetrahydrofuryl, alkylmercapto, arylmercapto, or alkenyl) aryl, substituted aryl (in which the substituents are as for substituted alkyl), or R2 and R3 conjoined are alkylene, substituted alkylene (in which the substitutents are nitro or as for substituted alkyl), phenylene or substituted phenylene (in which the substituents are nitro or as for substituted alkyl), each R4 is independently selected from H, alkyl, or monohydroxyalkyl, each R5 is C2 to C6 alkylene, and x is O or an integer from 1 to 5.  The vehicle may be linseed oil, oleoresin, polyamide resin, phenolic resin, epoxy resin, alkyd resin, linseed oil derivatives capable of being thinned by water latices of polyvinyl alcohol or acetate, styrenebutadiene copolymers or polyacrylic polymers.  In examples two coats of paint were brushed on to wooden panels.  The paints may be applied by brush or spray to wood, metal or fibre-board or articles such as panels, moulding, trim boards, furniture, shingles and picture frames.