Patent GB-1085930-A (GB)
Title: Acetylene association complexes
IPC: C02F1/50
Filed: 1965-12-30
Abstract: The invention comprises association complexes prepared by contacting (A) an amine RNR2R2, wherein R is a C8-21 alkyl, phenyl, naphthyl, furfuryl, tetrahydrofurfuryl or cyclohexyl group, or a group R1-NH-(CH2)y-, where R1 is C8-18 alkyl or alkenyl and y is 2, 3 or 4, R2 is hydrogen or a methyl group, or  (B) an acid addition salt thereof, or  (C) a quaternary ammonium compound <FORM:1085930/C4-C5/1> in which R3 is C8-18 alkyl or alkenyl group, phenyl, naphthyl, tetrahydrofurfuryl, furfuryl or a group R1-NH-(CH2)y, R4 is C8-18 alkyl, methyl or a benzyl group, and X is halogen; with an acetylenic compound R5-C­C-R6 in which R5 is hydrogen, or a vinyl, methyl, ethyl or phenyl group and R6 is hydrogen or a phenyl group, in the presence of an aqueous or organic solvent for at least one of said compounds. The complexes possess biocidal properties (see Division C1).  Examples relate to complexes obtained from acetylene or ethylacetylene and an amine mixture of mono-tallow-trimethylammonium chloride and dicocodimethylammonium chloride.ALSO:Industrial water is treated with a biocide which is an amino acetylenic association complex obtained by contacting, in the presence of an aqueous or organic solvent,  (A) an amine RNR2R2, where R2 is a C8- 21 aliphatic group, a phenyl, naphthyl, furfuryl, tetrahydrofurfuryl or a cyclohexyl group or R1-NH-(CH2)y-, where R1 is a C8- 18 alkyl or alkenyl group and y is 2, 3 or 4; and R2 is hydrogen or a methyl group; or  (B) an acid addition salt thereof, or (C) a quaternary ammonium compound <FORM:1085930/C1/1> where R3 is a C8- 18 alkyl or alkenyl group, or a phenyl, naphthyl, furfuryl, tetrahydrofurfuryl or cyclohexyl group, or R1-NH-(CH2)y-; R4 is a C8- 18 alkyl, methyl or benzyl group; an X- is halogen; with an acetylenic compound of the formula R5-C­C-R6, where R5 is hydrogen or a vinyl, methyl, ethyl, -COOH, -CH2OH, phenyl or <FORM:1085930/C1/2> or <FORM:1085930/C1/3> group; and R6 is hydrogen or a phenyl, monohalomethyl or <FORM:1085930/C1/4> group.ALSO:The invention comprises complexes prepared by contacting (A) an amine of the formula RNR2R2, where R is C8- 21 alkyl, phenyl, naphthyl, tetrahydrofurfuryl, or a cyclohexyl group or R1-NH-(CH2)y-, where R1 is C8- 18 alkyl or alkenyl and y is 2, 3, or 4; and R2 is hydrogen or a methyl group; or (B) an acid addition salt thereof: or (C) a quaternary ammonium salt of the formula (CH3)2N + R3R4X-in which R3 is a C8- 18 alkyl or alkenyl group, or a phenyl, naphthyl, tetrahydrofurfuryl, furfuryl or cyclohexyl group or R1-NH-(CH2)y; R4 is a C8- 18 alkyl, methyl or benzyl group; an X is halogen, with an acetylenic compound of the formula R5-C­C-R6, wherein R5 is hydrogen or a vinyl, methyl, ethyl, -COOH, -CH2OH, phenyl group or -C(CH3)2OH, -C(CH3)(sec.-butyl)OH, -CH(n-propyl)OH; and R6 is hydrogen or a phenyl, monohalomethyl or -C(CH3)(sec.-butyl)OH group, in the presence of an aqueous or organic solvent for at least one of said compounds.  As some of the acetylenic compounds are acids and halides, the association complexes include acid addition salts and quaternary ammonium compounds. The complexes possess biocidal properties (see Division C1).  Examples relate to complexes obtained from propargyl alcohol and an amine mixture of mono-tallow trimethyl ammonium chloride and dicocodimethyl ammonium chloride; hexadecyldimethylamine and propargyl bromide (hexadecyldimethylpropargyl ammonium bromide) and cocopropylene diamine and propiolic acid (cocopropylene diamine dipropiolate).