Patent GB-788079-A (GB)
Title: A process for preventing the electrostatic charging of synthetic fibres
IPC: D06M15/39
Filed: 1955-06-20
Abstract: Quaternary compounds of the formula CH2=C(R)CONHR1N(tert.)X where R is hydrogen or methyl, R1 is alkylene, in which the carbon chain may be interrupted by hetero atoms such as oxygen, N(tert.) stands for the group of atoms forming an aliphatic or heterocyclic tertiary amine and X stands for the monovalent anion of a salt forming acid, are prepared by quaternizing the amides with, e.g., alkyl or aralkyl halides, alkyl sulphates or halogen-substituted fatty acid salts in suspension or solution in water or organic solvents.  Specified quaternizing agents include dimethyl sulphate, methyl p-toluene sulphonate, allyl bromide, cetyl bromide, butyl bromide and benzyl chloride.  A halogen anion in the compound may be exchanged by metathesis with silver acetate, sodium stearate or sodium dodecyl sulphate or, by using a cation exchange resin, a quaternary hydroxide may be formed which may be neutralized with phosphoric acid.  In an example, (1) N-(b -diethyl-aminoethyl)-methacrylamide is prepared from methacrylyl chloride and N : N-diethylethylene diamine, and quaternized with dimethyl sulphate.  Other monomeric amides prepared and quaternated in the examples include N-(b -piperidinoethyl)-methacrylamide, N - (b  - dimethylaminoethyl)-methacrylamide, N - (g  - dimethylaminopropyl) - methacrylamide, N - (b  - dimethylaminoethyl) - acrylamide, N - (g  - dibutylaminopropyl) - acrylamide, N - (g  - dibutylaminopropyl) - methacrylamide and N - (g -diethylaminopropyl) methacrylamide, and amongst other monomeric amides mentioned are N-(b -morpholinoethyl)-methacrylamide and N - (g  - hexamethyleneaminopropyl) - methacrylamide.  Some hydrochloride salts of the tertiary bases are mentioned.ALSO:Synthetic fibres are treated with a polymeric quaternary ammonium compound, the monomeric form of which is of the formula: CH2 = C(R)CONH.R1-N(tert.)X where R is hydrogen or CH3, R1 is an alkylene radical in which the carbon chain may be interrupted by heteroatoms, e.g. oxygen, N(tert.) stands for the group of atoms forming an aliphatic or heterocyclic tertiary amine and X stands for the monovalent anion of a salt-forming acid. The quaternization may be effected with an alkyl or aralkyl halide, alkyl sulphate or halogen-substituted fatty acid salt, either before or after polymerization.  The anion X may be an acetate, stearate or dodecosulphate anion introduced into the compound by reacting the quaternary halide with silver acetate, sodium stearate or sodium dodecyl sulphate or, by using an anion-exchange resin, a quaternary ammonium hydroxide may be formed which is neutralized with phosphoric acid.  Several starting materials are described including N-(b  - dimethylaminoethyl) - methacrylamide, N-(g  - piperidinopropyl) - methacrylamide and N - (g  - hexamethylene aminopropyl) - methacrylamide.  The polymer may be applied in aqueous or organic solution at normal or elevated temperature, and after impregnation the fibres may be dried at temperatures up to 150 DEG  C. If dried at room temperature the treated fibres may also be baked at 50-150 DEG C.  The fibres may be after-treated with soap or sodium oleyl sulphate.  The fibres may be treated as yarns or fabrics.  In examples, fabrics of polyethylene terephthalate and nylon are treated.ALSO:Polymers of quaternary compounds of the formula CH2 = C(R.)CONHR1-N(tert.)X, where R is hydrogen or methyl, R1 is alkylene in which the carbon chain may be interrupted with hetero-atoms, e.g. oxygen, N(tert.) stands for the group of atoms forming an aliphatic or heterocyclic tertiary amine and X stands for the monovalent anion of a salt-forming acid, are used for treating textiles.  The polymers may be prepared by quaternizing the monomeric amide and polymerizing the resulting salt or by first polymerizing the amide and quaternizing the polymer.  In both cases, quaternization is effected with alkyl halides, aralkyl halides, alkyl sulphates or halogen-substituted fatty acid salts in suspension or solution in water or organic solvents.  Catalysts for polymerization may be potassium or ammonium persulphate, a mixture of ammonium persulphate and sodium hydrosulphite, or benzoyl peroxide.  The anion in polymers of compounds of the above formula may be replaced by an acetate, stearate or dodecyl sulphate anion by interaction with silver acetate, sodium stearate or sodium dodecyl sulphate or, by using an anion exchange resin, a quaternary hydroxide may be formed which may be neutralized with phosphoric acid.  In examples: (1) N-(b -diethylaminoethyl)-methacrylamide is quaternized with dimethyl sulphate in benzene and the product is polymerized in aqueous solution at 100 DEG  C. using ammonium persulphate as catalyst; (2) the hydrochloride of N-(b -diethylaminoethyl)-methacrylamide is polymerized in aqueous solution at 100 DEG  C. using ammonium persulphate as catalyst; and the polymeric tertiary base produced is quaternized with dimethyl sulphate.  Other examples are similar, and amongst the monomeric amides used are N-(b -piperidinoethyl) - methacrylamide, N - (b  - dimethylaminoethyl) - methacrylamide, N - (g  - dimethylaminopropyl) - methacrylamide and N-(g  - diethylaminopropyl) - methacrylamide, and quaternizing agents include methyl p-toluene sulphonate, cetyl bromide, butyl bromide, allyl bromide and benzyl chloride.  Other monomeric amides referred to include N-(b -morpholinoethyl) - methacrylamide and N-(g  - hexamethyleneaminopropyl) - methacrylamide.