Patent GB-579340-A (GB)
Title: Use of polyester-amide compositions for coating, impregnating, adhesive or like purposes
IPC: D06M15/564
Filed: 1943-12-06
Abstract: Compositions which comprise a solution of a polyesteramide in an organic solvent in admixture with an organic diisocyanate are used under conditions which avoid the use of heat for coating, impregnating, adhesive or like purposes.  The polyesteramides may already have been slightly modified by treatment with an organic diisocyanate to a point at which they still retain their solubility in organic solvents.  Suitable solvents are acetone, mixtures of benzene and acetone, mixtures of benzene and chloroform, mixtures of benzene and methyl ethyl ketone and mixtures of methyl ethyl ketone with trichlorethylene.  Water should be avoided.  Suitable diisocyanates are ethylene, trimethylene, tetramethylene, hexamethylene, decamethylene, p-phenylene, m-phenylene, diphenyl-4 : 41, diphenylmethane 4 : 41, naphthalene, and adipyl diisocyanates. Usually not more than 10 per cent of diisocyanate on the weight of polyesteramide is employed.  Solution of the polyesteramide in organic solvents may be facilitated by mechanical working or by thermal degradation.  The compositions may include fillers, e.g. carbon black, clay, blanc fixe, whiting, lithopone or mica; natural or synthetic rubber; plasticisers, e.g. tricresyl phosphate, dibutyl phthalate, butylphthalylbutyl glycollate or N - alkyltoluenesulphonamides; stabilisers or antioxidants, e.g. the diphenyl-o-tolylguanidine salt of dicatechol borate, diphenylamine - acetone condensation products and diphenyl-p-phenylene diamine. Pigments may also be included and oil-soluble metallic driers, e.g. lead or cobalt naphthenates. Other materials reactive with the diisocyanate may also be included, e.g. cellulose acetate, cellulose nitrate, cellulose ethers, viscose, casein, zein, soya-protein, polyvinyl alcohol or wood-flour.  If desired two separate compositions may be employed, one containing a solution of polyesteramide and the other a diisocyanate with or without a solvent.  These may be mixed together immediately or shortly before use or may be applied separately to the surfaces which are then adhesively united together or consecutively to the surface of the article to be coated or impregnated.  The compositions may be used for adhesively uniting fabrics, leather, sheets or shaped articles of various material with themselves or with other materials or articles. Granular or fibrous materials, e.g. cork dust, leather dust, wood dust, asbestos, or wool, cotton or other fibres, loose p  or in the form of felts may be fabricated with the compositions as binders into sheets or other shapes.  Or the compositions may be used in usual manner for coating or impregnating.  Suitable reactants for making the polyesteramides are ethylene, diethylene, trimethylene, pentamethylene, hexamethylene, decamethylene or dodecamethyleneglycol, 1 : 12-octadecanediol or pentaglycol; amino alcohols such as ethanolamine and 3-amino-propanol; dibasic carboxylic acids, e.g. malonic, maleic, fumaric, succinic, glutaric, suberic, azelaic, b -methyladipic, adipic, pimelic, sebasic, undecanedioic, brassylic, isophthalic, hexahydroterephthalic, p-phenylenediacetic, dihydrosuccinic, or acetylene dicarboxylic acid; diamines, e.g. ethylenediamine, hexamethylenediamine, 3-methylhexamethylenediamine, decamethylenediamine, or m-phenylenediamine; monohydroxymonocarboxylic acids, e.g. glycollic, 6-hydroxycaproic, 10-hydroxydecanoic, or 12-hydroxystearic acid; and polymerisable monoaminomonocarboxylic acids, e.g. 6-aminocaproic acid, caprolactam, 9-aminononanoic, 11-aminoundecanoic or 12-aminostearic.  In the examples: (1) a polyesteramide from adipic acid, ethylene glycol and monoethanolamine is dissolved in a benzene-chloroform mixture, and modified by boiling with hexamethylene diisocyanate.  To the resulting solution m-phenylene diisocyanate dissolved in benzene is added.  Air-dried films formed from the mixture are no longer soluble in organic solvents.  (2) A similarly modified polyesteramide is lightly milled and dissolved in a benzene-acetone mixture and m-phenylene diisocyanate dissolved in the same solvent is added.  The composition may be used for making a composite fabric for fuel or oil containers, or if allowed to stand for 2 hours after mixing it forms a slurry which may be used as a slushing composition for fuel containers made from fabrics, leather, felt or vulcanised film or for making coated fabrics. (3) A composition similar to that of example (2) with p-phenylene diisocyanate instead of the m-compound.  (6) The composition of example (2) is mixed with its own weight of cork powder and the mixture dried to form tough sheets which may be shaped by hydraulic pressure.  (7) The composition of example (2) is diluted with the mixed solvents and leather dust added to form a thick dough which is formed into sheets.  (8) A composition is made as in example (2) using hexamethylene diisocyanate in place of the m-phenylene compound.  Cobalt or lead naphthenate in white spirit is added and films formed from the thickened solution.  Diphenyl 4.41-diisocyanate may replace the m-phenylene diisocyanate. (9) The polyester amide of example (1) is dissolved in benzeneacetone mixture and carbon black added.  The dough is spread on fabric, dried, treated with a benzene solution of m-phenylene diisocyanate and again dried.  (10) The diisocyanate modified polyesteramide of example (2) is lightly milled and paddled to a smooth solution with a benzene acetone mixture. Diphenylmethane4 41-diisocyanate dissolved in the same mixture is added to form an adhesive.  (11) The diisocyanate modified polyesteramide of example (2) is lightly milled and paddled with acetone to give a smooth solution to which is added a solution of nitrocellulose or cellulose acetate in acetone and di-phenylmethane-4 , 41-diisocyanate.  Specifications 553,733, 561,104, 561,108 and 574,134 are referred to.