GB1447911A - Process for producing polyamines - Google Patents

Abstract

1447911 Polymerization of diallylamine derivatives NITTO BOSEKI CO Ltd 4 April 1974 [5 April 1973 9 July 1973 26 July 1973 4 Oct 1973 13 Aug 1973] 15008/74 Heading C3P Polyamines are prepared by irradiation with light having wavelengths of 150-500 mÁ of a mixture which comprises (a) at least one diallylamine derivative of formula wherein R<SP>1</SP> is hydrogen or methyl; R<SP>2</SP> and R<SP>3</SP> are independently hydrogen, allyl, methallyl, straight-chain or branched chain alkyl having 1-16 carbon atoms, phenylalkyl having 7-19 carbon atoms, or hydroxyalkyl of formula HO-(CH 2 ) m - wherein m is 1-6 or R<SP>2</SP> and R<SP>3</SP> may form, together with the adjacent nitrogen atom, pyrrolidyl, piperidyl or monopholino; and Y is halogen or inorganic acid anion; (b) optionally, with at least one comonomer selected from maleic acid, maleic anhydride, N-vinylpyrrolidone, and a vinyl compound of formula wherein R<SP>4</SP> is hydrogen or methyl; and Z is OR<SP>5</SP> (wherein R<SP>5</SP> is hydrogen, methyl, in which n is 1-5, or where R<SP>6</SP>, R<SP>7</SP>, R<SP>8</SP> are independently hydrogen, alkyl having 1-3 carbon atoms or benzyl; J is halogen; n is defined as above) or wherein R<SP>9</SP> and R<SP>10</SP> are independently hydrogen, alkyl having 1-5 carbon atoms or -(CH 2 ) p OH- wherein p is 1-3; (c) up to 30% by weight based on the total weight of monomers, of a solvent or non-solvent; and (d) optionally, in the presence of a sensitizer. The photopolymerization is conducted on a solution or slurry of the mixture, preferably in the form of a film or plate of thickness 0À1-5 cm. using fluoroescent lamps, low-pressure mercury are lamps or sunlight as the radiation source at a temperature of -10‹ to 100‹ C. Preferred compounds are diallyldimethylammonium chloride, methyldiallylaminehydrochloride, diethyldiallylammonium chloride, diallylpyrrolidium chloride, methylbenzyldiallylammonium chloride, methyldiallylamine phosphate, diallylmorpholinium chloride, whilst (II) may be selected from acrylamide, acrylic acid, dimethylaminoethyl methacrylate hydrochloride and dimethylbenzylammoniumethyl methacrylate chloride. The solvent or non-solvent may be selected from water or methyl alcohol, ethyl alcohol, isopropyl alcohol, dimethylsulphoxide, acetone or aqueous solutions thereof. The sensitizer is a mixture of at least one compound of formula wherein A is phenyl, phenyl substituted by R<SP>11</SP> or straight-chain or branched-chain alkyl having 1-5 carbon atoms; and R<SP>11</SP> is hydrogen halogen, methoxy, nitro or straight-chain or branched-chain alkyl having 1-5 carbon atoms (preferred benzophenone and acetophenone) and at least one compound of formulµ wherein R<SP>11</SP> is defined as above; R<SP>12</SP> is hydrogen or straight-chain or branched-chain alkyl having 1-5 carbon atoms; X is -CH 2 -, -O-, -NR<SP>12</SP> or -N(CH 2 CH 2 OH)-; R<SP>13</SP>, R<SP>14</SP> and R<SP>15</SP> are independently hydrogen (but not at the same time), alkyl having 1-3 carbon atoms, hydroxymethyl, #-hydroxyethyl, γ-hydroxypropyl, benzyl, allyl or methallyl (preferred are hydroquinone, hydroquinone monomethyl ether, hydroquinone monoethyl ether, morpholine, dioxane, N - (# - hydroxyethyl)morpholine and N-methyl morpholine). The sensitizer may also comprise a charge-transfer complex of sulphur dioxide and a compound of Formula I (preferred are diallyldimethylammonium chloride, diallyldiethylammonium chloride and diallylmorpholinium chloride) which may be dissolved in water or methyl alcohol, ethyl alcohol, isopropyl alcohol, dimethylsulphoxide, acetone or aqueous solutions thereof.