Patent GB-985213-A (GB)
Title: Saturated water-laid fibre sheets and products made therefrom
IPC: C08G73/02
Filed: 1961-01-04
Abstract: Alkyleneamides of dicarboxylic acids are made by reacting a 1,2-alkylenimine in aqueous solution containing also an acid-acceptor with a solution of a chloride of a dicarboxylic acid. The imine may be ethylenimine, 1,2-propylenimine, 1,2 - butylenimine or 1,2 - pentylenimine. Acid chlorides referred to are sebacoyl, isosebacoyl, azelaoyl, suberoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, isophthalyl and terephthaloyl dichlorides.  A small excess of imine over the theoretical may be employed.  The acid-acceptor may be an alkali-metal carbonate or bicarbonate.  The solvent for the acid chloride is one that is substantially immiscible with water, inert towards the reactants and the product, and a solvent for the product.  The product is recovered by evaporating the solvent.ALSO:A water-laid sheet of fibre is impregnated with and reinforced by an intimately fibre-contacting, flexible, tack-free, solid, resinous polymer in an amount equal to at least 25% by weight of the sheet, the polymer being the product of reaction in situ between two organic compounds of specific classes.  The first organic compound has at least two 1,2-alkyleneamide rings per molecule, i.e. groups in which the aziridine ring <PICT:0985213/C3/1> is united to an acid radical, e.g. <PICT:0985213/C3/2> The second organic compound has at least two reactive hydrogen-bearing groups per molecule, and a molecular weight equal to at least one hundred times the number of hydrogen-bearing groups per molecule.  Suitable groups are -COOH, -OH, -SH and NH2.  The Specification includes lists of suitable compounds of all the above classes.  The first compound is preferably used in amount sufficient to provide at least two aziridine rings per molecule of the second compound, but not more than two aziridine rings per reactive hydrogen-bearing group of the second compound. The sheet may be impregnated by immersion in a bath containing the two reactants in a solvent.  The solvent may be removed and the reactants cured by heating, or more slowly by allowing to stand at room temperature. The impregnating bath may also contain fillers, e.g. calcium carbonate, iron oxide, titanium dioxide, carbon black or silica, dyes, accelerators, antioxidants and catalysts. In Example 1, the impregnant solution comprises N,N1-bis-1,2-ethylenisosebacamide and a liquid di-mercaptan, formed by reacting dichlorodiethylformal and an alkali polysulphide, in toluol; in Example 3 the same amide and solvent with a trimer of linoleic acid; in Example 4, the same amide and solvent with a carboxyl-terminated polyester prepared from ethylene glycol, 1,4-butandiol and adipic acid; in Example 5, a hydroxyl-terminated polyester made from diethylene glycol and adipic acid is reacted with pyromellitic dianhydride to form a carboxyl-terminated polyester, this is dissolved with 2,2-bis-para-(1,2-propylene-metacarbamato - phenetyl) - propane in toluene; in Example 6, 2,2-bis-(betahydroxybetamethylphenetyl)-propane is reacted with the maleic anhydride adduct of methyl-cyclopentadiene, this product is reacted with a polyester from neopentylene glycol, trimethylolpropane and adipic acid in butyl acetate and methylethylketone, and is cured with a solution in ethanol of tris-1-aziridinylphosphine oxide; in Example 7, the solution comprises ethylene glycol monoethyl ether, N,N1-bis-ethylene sebacamide and an amine-terminated polyamide resin made by reacting fatty acid polymers and aliphatic polyamines; in Example 8, the solution comprises toluol, N,N1-bis-ethylenisosebacamide, N,N1-bis-ethylenisophthalamide and a C36 di-primary amine; in Example 9, the solution comprises toluene, N,N1-bis-1,2-propylenisophthalamide and a branched polyester prepared from isosebacic acid, neopentylene glycol and trimethylolpropane; in Example 10, N,N1-bis-1, 2-propylenisosebacamide is used with the same polyester and solvent as in Example 9; and in Example 11, the solution comprises toluol, a moderately branched, hydroxyl-terminated polyester formed from adipic acid, hexantriol and butylene glycol, N,N1-bis -ethylenisophthalamide and dimethylbenzylamine. U.S.A. Specifications 2,302,288, 2,327,760, 2,373,015, 2,407,566, 2,435,478, 2,450,940, 2,482,761, 2,663,705, 2,672,459, 2,705,223, 2,802,824 and German Specification 740,723 are referred to.ALSO:A backing sheet for sandpaper comprises a water-laid sheet of fibre impregnated with and reinforced by an intimately fibre-contacting, flexible, tack-free, solid, resinous polymer in an amount equal to at least 25% by weight of the sheet, the polymer being the product of reaction in situ between two organic compounds of specific classes.  The first organic compound has at least two 1,2-alkylenamide rings per molecule, i.e. groups in which the aziridine ring <FORM:0985213/C4-C5/1> is united to an acid radical, e.g. <FORM:0985213/C4-C5/2> or <FORM:0985213/C4-C5/3> The second organic compound has at least two reactive hydrogen-bearing groups per molecule, and a molecular weight equal to at least one hundred times the number of hydrogen-bearing groups per molecule.  Suitable groups are -COOH, -OH, -SH and NH2. The Specification includes lists of suitable compounds of all the above classes.  The first compound is preferably used in amount sufficient to provide at least two aziridine rings per molecule of the second compound, but not more than two aziridine rings per reactive hydrogen-bearing group of the second compound. The sheet may be creped.  In Example 2, one major surface of the impregnated paper was made slip-resistant by treatment with a plasticized polyvinyl acetate latex, and the other major surface sized with a latex of a terpolymer of butadiene, styrene and acrylonitrile. After drying, an alkyd resin adhesive was coated on to the second surface and silicon carbide granules applied electrostatically.  The alkyd resin was heat-cured, a phenol-formaldehyde resin applied and in turn heat-cured. U.S.A. Specifications 2,302,288, 2,327,760, 2,373,015, 2,407,566, 2,435,478, 2,450,940, 2,482,761, 2,663,705, 2,672,459, 2,705,223, 2,802,824 and German Specification 740,723 are referred to.ALSO:Transparent labelling tape or pressure-sensitive adhesive tape for masking in paint-spraying has a backing sheet of water-laid fibre impregnated with and reinforced by an intimately fibre-contacting, flexible, tackfree, solid, resinous polymer in an amount equal to at least 25% by weight of the sheet, the polymer being the product of reaction in situ between two organic compounds of specific classes.  The first organic compound has at least two 1,2-alkyleneamide rings per molecule, i.e. groups in which the aziridine ring <FORM:0985213/B1-B2/1> is united to an acid radical, e.g. <FORM:0985213/B1-B2/2> or <FORM:0985213/B1-B2/3> The second organic compound has at least two reactive hydrogen-bearing groups per molecule, and a molecular weight equal to at least one hundred times the number of hydrogen-bearing groups per molecule.  Suitable groups are -COOH, -OH, -SH and NH2.  The Specification includes lists of suitable compounds of all the above classes.  The first compound is preferably used in amount sufficient to provide at least two aziridine rings per molecule of the second compound, but not more than two aziridine rings per reactive hydrogen-bearing group of the second compound.  The sheet may be creped.  U.S.A. Specifications 2,302,288, 2,327,760, 2,373,015, 2,407,566, 2,435,478, 2,450,940, 2,482,761, 2,663,705, 2,672,459, 2,705,223, 2,862,824 and German Specification 740,723 are referred to.ALSO:A water-laid sheet of fibre is impregnated with and reinforced by an intimately fibre-contacting, flexible, tackfree, solid, resinous polymer in an amount equal to at least 25% by weight of the sheet, the polymer being the product of reaction in situ between two organic compounds of specific classes.  The first organic compound has at least two 1, 2-alkyleneamide rings per molecule, i.e. groups in which the aziridine ring <FORM:0985213/D1-D2/1> is united to an acid radical, e.g.  The <FORM:0985213/D1-D2/2> second organic compound has at least two reactive hydrogen-bearing groups per molecule, and a molecular weight equal to at least one hundred times the number of hydrogen-bearing groups per molecule.  Suitable groups are -COOH, -OH, -SH and NH2.  The Specification includes lists of suitable compounds of all the above classes.  The first compound is preferably used in amount sufficient to provide at least two aziridine rings per molecule of the second compound, but not more than two aziridine rings per reactive hydrogen-bearing group of the second compound. The sheet may be creped and may be impregnated by immersion in a bath containing the two reactants in a solvent.  The solvent may be removed and the reactants cured by heating, or more slowly by allowing to stand at room temperature. The impregnant bath may also contain fillers, e.g. calcium carbonate, iron oxide, titanium dioxide, carbon black or silica, dyes, accelerators, antioxidants and catalysts.  The treated sheets may be used as a backing sheet for sandpaper, or may be translucent enough for use as tracing film or transparent labelling tape, or for pressure-sensitive adhesive tape for masking in paint-spraying.  In Example 1 the impregnant solution comprises N, N1-bis-1, 2-ethylenisosebacamide and a liquid di-mercaptan, formed by reacting dichlorodiethylformal and an alkali polysulphide, in toluol; in Example 3 the same amide and solvent with a trimer of linoleic acid; in Example 4, the same amide and solvent with a carboxyl-terminated polyester prepared from ethylene glycol, 1, 4-butandiol and adipic acid; in Example 5, a hydroxyl-terminated polyester made from diethylene glycol and adipic acid is reacted with pyromellitic dianhydride to form a carboxyl-terminated polyester, this is dissolved with 2, 2-bis-para-(1, 2-propylene-meta-carbamato