Abstract: High molecular weight aromatic polyamines are produced by hydrolyzing a polyisocyanate having an isocyanate content of from 21 to 52.5% and an isocyanate-reactive group-containing compound having a molecular weight of from 400 to 10,000 in the presence of an excess of water. The reactants are used in quantities such that the equivalent ratio of isocyanate to isocyanate-reactive groups is from 0.1 to 5. Further, water is used in an amount such that the equivalent ratio of water to isocyanate groups is greater than 1. Low molecular weight compounds containing isocyanate-reactive groups, solvents, basic catalysts and urethanization catalysts may also be included in the mixture to be hydrolyzed. The hydrolysis is carried out at a temperature of from -20.degree. to 175.degree. C. The product amine is isolated from the reaction mixture by procedures such as phase separation, extraction and distillation. The polyamines thus-produced are particularly useful in the production of polyurethanes.

Abstract: A polyamide-imide resin which can give a varnish having a high resin content, excellent in storage stability and heat resistant final products such as insulated wire can be produced by reacting an aromatic diisocyanate with a tricarboxylic acid anhydride in the presence of a basic solvent while adjusting the resin content at 40% by weight or more, and adding a compound having one active hydrogen atom before, during or after the above-mentioned reaction so as to adjust the reduced viscosity of the resin to 0.27 or lower.

Abstract: The invention relates to a self-crosslinking heatcurable binder, in particular for electropaints, which is based on an organic synthetic resin which contains primary and/or secondary and, if desired, also tertiary amino groups and esterified carboxyl groups and is water-dilutable due to partial or complete neutralization with acids. The esterified carboxyl groups are activated in the alcohol component by a substituent which induces a negative inductive effect.

Abstract: A method of forming a urethane prepolymer comprising the steps of gradually adding an isocyanate compound to a hydrophilic polyether or polyester compound without substantial added mixing whereby a relatively dense isocyanate layer and a polyether or polyester layer overlying the isocyanate layer are formed, and a urethane prepolymer-forming reaction occurs at the interface between the layers. The resulting urethane prepolymer may be reacted with water to form a cellular urethane polymer, or with an aqueous slurry of unconsolidated aggregate material to form a consolidated aggregate product, such as a plant growth supporting rooting medium.

Abstract: The invention relates to reaction injection molded elastomers of improved green strength containing polyurea linkages derived from high molecular weight amine terminated polyethers, a chain extender, a polyisocyanate and an anhydride. The reaction injection molded (RIM) elastomers of this invention are useful, for example, as automobile body parts.

Abstract: A polyester polyurethane compound is formed by reacting trans-1,4-cyclohexanediisocyanate with a mixed polyester. The mixed polyester can be the copolymerization condensation product of an aliphatic dicarboxylic acid or an aromatic dicarboxylic acid, or a separate physical blend thereof reacted with a polyol. The polyurethane can also contain small amounts of non-extractable epoxies and carbodiimides. The urethane has very good hydrolytic stability in comparison with prior art polyurethane systems and also very good fuel resistance and anti-icing resistance. A preferred area of use is an aircraft fuel tanks and anti-icing components.

Abstract: The invention relates to a selfcrosslinking heat-hardenable binder, in particular for electropaints, which is based on an organic synthetic resin which contains hydroxyl groups and esterified carboxyl groups in the form of carbalkoxymethyl ester groups and is water-dilutable by partial or complete acid-neutralization of amino groups present in the resin.

Abstract: Blends of silicone surfactants substantially free of isocyanate reactivity and certain polysiloxane compounds having pendant organic chains which have at least one isocyanate reactive functional group are useful as internal mold release agents. These blends form stable dispersions in liquid polyisocyanates for use in reaction injection molding techniques.

Abstract: The invention relates to reaction injection molded elastomers derived from high molecular weight amine terminated polyethers and/or high molecular weight polyols, a chain extender, a polyisocyanate and an epoxy modified filler material. The reaction injection molded (RIM) elastomers of this invention are useful, for example, as automobile body parts.

Abstract: Disclosed is an improved process for the production of organic polyisocyanate based molded polymers prepared from at least one organic polyisocyanate and at least one polyol in the presence of an internal release agent wherein the improvement comprises employing as said agent a polysiloxane having at least one unit of the formula ##STR1## wherein R is selected from the group consisting of lower-alkyl and aryl, R.sup.1 is a divalent hydrocarbon radical, and R.sup.2 is selected from the group consisting of lower-alkoxy, aryloxy, particular hydroxyalkyleneoxy, alkoxyalkyleneoxy, amino, and hydroxyalkylamino radicals.The molding process can be repeated in many cycles before the molds require cleaning or treatment with release agent. The ease and rapidity with which the present process can be carried out makes it particularly suited to RIM production methods.

Abstract: The object of this invention is a moisture-curing, storage stable, single-component polyurethane system comprising:A. a polyurethane prepolymer with a free isocyanate content of 1 to 5 percent by weight;B. a dialdimine having the formulaR[--N.dbd.CH--C(CH.sub.3).sub.2 --CH.sub.2 --O--CO--CH--(CH.sub.3).sub.2 ].sub.2in whichR is a divalent aliphatic radical with 2 to 10 carbon atoms, aliphatic radical having 4 to 10 carbon atoms and containing ether oxygen and/or lower alkylamino nitrogen atoms, cycloaliphatic radical with 6 to 15 carbon atoms oraromatic radical with 6 to 21 carbon atoms;andC. an acid catalyst selected from the group consisting of aliphatic carboxylic acids, aromatic carboxylic acids, toluenesulfonic acid, and mixtures thereof.The polyurethane systems are used as coating, sealing, casting, spackling and bonding materials.

Abstract: There are provided low temperature, storage stable, liquid mixture of (1) isocyanato-containing prepolymers obtained from the reaction of linear and/or slightly branched polyols and a polyisocyanate characterized by a methylene group --CH.sub.2 -- bonded to two benzenoid nuclei, and (2) a non-hydroxyl-containing flow modifier which is compatible with the said prepolymer. Novel liquid mixtures thus prepared exhibit little tendency to crystallize or phase separate when stored for prolonged periods of time, i.e., well below room temperature for several days.

Abstract: Novel polyamide-imide resin compositions, useful for electrically insulating conductors, are prepared by polycondensing a tribasic acid anhydride compound and a diisocyanate in an inert organic solvent in the presence of a catalytic amount of an oxyanion or amine compound at a high solids content, and controlling the reaction to prevent a great increase in viscosity.

Abstract: A protective colloid for use in an interfacial polymerization process comprising a graft copolymer of polyvinyl alcohol and methyl vinyl ether/maleic acid.

Abstract: A process for the production of a polycarbonate glycol wherein a cyclic carbonate is catalyzed at elevated temperature by a cationic initiator. Compounds of structure (I) ##STR1## where R is alkylene, R' and R" are independently hydrogen, alkyl, alkaryl, aralkyl, or aryl, are heated at an elevated temperature in the presence of cationic initiators such as trimethyl aluminum to form a polymer. Production of a glycol product is assured by subsequent heating at about 200.degree.-220.degree. C. to form a polymer containing carbonate units of ##STR2## and having hydroxy end units bonded to a carbon not part of a carbonate function. The molecular weight of polycarbonate glycol is preferably at least about 1,000. Valuable new prepolymer mixes and polyurethanes may be prepared using the novel polycarbonate glycols of the invention.

Abstract: The coating composition useful as the exterior finish on automobiles and trucks contains about 25-50% by weight of a binder of film-forming constituents and 50-75% by weight of a volatile organic solvent carrier and additionally contains 2-150% by weight, based on the weight of the binder, of pigment; the binder is about 20-70% by weight of an acrylic polymer containing reactive hydroxyl, carboxyl, amide groups or any mixture of such groups, about 0-40% by weight of a hydroxy-terminated polyester urethane resin and about 25-40% by weight of an alkylated melamine formaldehyde crosslinking resin; in addition the composition contains about 4-20% by weight, based on the weight of the binder, of a rheology control agent of an alcohol soluble cellulose acetate butyrate having a buryryl content of about 45-50% by weight, a hydroxyl content of about 4-5% by weight and a viscosity of about 0.2-0.4 second.

Abstract: The present invention is directed to a process for the production of polyurethane elastomer moldings by reacting a reaction mixture in a closed mold, wherein said reaction mixture comprises:(a) an organic polyisocyanate;(b) an organic active hydrogen group-containing compound having a molecular weight of from 1800 to 12,000 and containing at least two active hydrogen groups;(c) 1,3,5-triethyl-2,6-diamino benzene and, optionally(d) a catalyst for the reaction between hydroxyl groups and isocyanate groups,wherein component (c) is present in an amount of from 25 to 35 percent by weight based on the combined weight of components (b) and (c), wherein the amounts of components (a), (b) and (c) are such that the isocyanate index of the reaction mixture is from about 90 to 110, and wherein all of said components are processed via a one-shot process whereby (a) is mixed simultaneously either with (b), (c) and (d) or with a non-reacted premixture of some or all of (b), (c) and (d).

Abstract: A method for improving the pot life of polyurethane reaction mixtures by solubilizing the polyol component in the isocyanate to lower the required mixing temperature is disclosed.

Abstract: Improved rigid urethane and isocyanurate foam compositions having improved fire resistance are described. The urethane foams are based on furan compositions having the formula: ##STR1## and from about 100% to about 500% of a stoichiometric amount of a reactive polyisocyanate to produce a foamable composition, and sufficient blowing agent to create a foam having a density from about 1.5 to about 5 pounds per cubic foot. The product has improved fire resistence. The disclosure also described the method of decreasing the flame hazard potential of a rigid foam by adding two urethane or isocyanurate foaming ingredients the appropriate amount of one or more of the compositions listed above. The polymers described are chiefly made from adding propelyne oxide to bis (hydroxymethyl) furan.

Abstract: Novel high molecular weight resins, useful for electrically insulating conductors, are prepared by polycondensation of a dianhydride, or a mixture of two or more dianhydrides, and a diisocyanate in an inert organic solvent, preferably in the presence of a catalytic amount of 2-methylimidazole.

Abstract: A modified polyamide-imide resin and method for making the same. The composition comprises the reaction product of an aromatic tricarboxylic acid anhydride reactant, an aromatic diisocyanate reactant and an aliphatic dicarboxylic acid reactant in a solution comprising an aprotic solvent at a temperature ranging from about 70.degree. C. to about 155.degree. C. The tricarboxylic acid anhydride reactant is present in an amount which is greater than about 25 mol percent of the total of the tricarboxylic acid anhydride-aliphatic dicarboxylic acid reactants.The method comprises the steps of dissolving the aromatic tricarboxylic acid anhydride and aliphatic dicarboxylic acid reactants and an excess of the aromatic diisocyanate reactants in aprotic solvent thereby forming a reaction solution. The aromatic tricarboxylic acid anhydride is present in an amount which is greater than about 25 mol percent of the total of the tricarboxylic acid anhydride-aliphatic dicarboxylic acid reactants.

Abstract: A process for the manufacture of a polyurethane prepolymer adhesive by a catalyst initiated reaction of polyol and isocyanate copolymers is performed under room temperature conditions, and in convenient quantities for application, storage, and transportation purposes. Compounding includes alternatives of catalyst and co-catalyst combinations, and additives, including a reaction inhibitor, plasticizer, delayed reaction catalyst and surfactant.

Abstract: Stable isocyanurate foams are produced at rapid reaction rates by contacting an organic polyisocyanate with an active hydrogen compound such as a polyether polyol in the presence of an initiator comprising an ortho-sulfonium phenoxide and a carbonylate salt such as sodium acetate.

Abstract: Low temperature flexible polyurethane elastomers are prepared by reacting organic polyisocyanates with polyester polyols which have glass transition temperatures of -10.degree. to -80.degree. C. and incorporating therein alkoxylated esters of fatty acids and/or alkoxylated terpene alcohols.

Abstract: The use of polyisocyanates as binders in the preparation of particle boards is subject to the drawback that the boards exhibit a tendency to adhere to the face of the platens used in their formation. This problem is minimized by incorporating minor amounts of a mixture of certain organic sulfonic acids, hydrogen sulfates, salts and derivatives thereof, into the polyisocyanate to be used as binder. The polyisocyanates and the sulfonic acids, hydrogen sulfates, salts and derivatives are applied to the particles separately, or after preblending one with the other. Whether the components are applied separately or in combination one with the other, they can each be applied either neat of in the form of an emulsion or emulsions.

Abstract: A polymer-modified polyol is formed by polymerizing an olamine, particularly an alkanolamine, with an organic polyisocyanate in the presence of a polyol. The alkanolamine reacts polyfunctionally with the polyisocyanate to produce polyaddition products.The polyaddition products may constitute a stable dispersion in the polyol and the resulting polymer-modified polyol is particularly useful as a polyol starting material for reaction with a polyisocyanate in the manufacture of polyurethane foam.

Abstract: The process comprises mixing chopped glass fibres with plastics-forming ingredients and moulding or forming the mixture to obtain reinforced plastics articles. The invention lies in the use of chopped glass fibres in filamentary form. Conveniently the glass fibres are first made into a slurry or paste, which forms the aspect of the invention, with a liquid compatible with the plastics-forming ingredients or with all or a part of one or more of the ingredients. The invention includes a novel form of chopped glass fibres formed from glass strand bound with a size containing as the main ingredient one component of a plastics-forming mixture or a derivative thereof. It also includes apparatus for mixing the glass fibre paste or slurry with plastics-forming ingredients by impingement mixing.The invention is of special use for reinforcing with glass fibres plastics articles, especially polyurethane plastics articles, formed by a Reaction Injection Moulding (RIM) process.

Abstract: Process for the production of sheet products having a suede-like surface by application of a coating paste to a matrix whose surface has the structure of a negative of suede or suede-like materials, solidification of the coating by heating, stripping of the solidified coating from the matrix and, optionally, laminating it to a textile material, characterized in that:(a) a coating paste of a two-component system which does not harden to a polyurethane urea until heated, which system is based either on a blocked isocyanate prepolymer and a polyamine or on an isocyanate prepolymer and a complex of an alkali metal halide and an aromatic polyamine and, optionally, up to about 40% by weight, preferably less than about 30% by weight, more preferably less than about 25% by weight, and most preferably less than about 15% by weight, of solvent, so that the coating paste has a viscosity of at the most about 100,000 mPa.s at room temperature, is applied;(b) the coating is heated to a temperature of from about 30.degree.

Abstract: Novel high molecular weight resins, useful for electrically insulating conductors, are prepared by polycondensing a mixture of anhydrides, and a diisocyanate and/or a diamine in an inert organic solvent, preferably in the presence of a catalytic amount of 2-methylimidazole.

Abstract: Bis(cyclic ureas) are disclosed which have the formula ##STR1## wherein R is ##STR2## and C.sub.n H.sub.2n is ethylene or 1,3-propylene each of which can be substituted by one or more inert substituents.These compounds are useful as masked diisocyanates which, on heating in the presence of a polyol and, optionally, a polyurethane catalyst, give rise to polyurethane resins. Accordingly, they are useful as a component of storage stable compositions which are convertible to polyurethanes upon heating. Such compositions are particularly useful as solvent-less coating compositions. The properties of the above compounds are distinguished in a number of respects from the known bis(cyclic ureas) in which C.sub.n H.sub.2n has 4 or more carbon atoms in the chain between the valencies. Illustratively, the above compounds are more stable on exposure to heat in the absence of catalysts but, in the presence of polyurethane catalysts, react with polyols at a significantly faster rate than the prior art compounds.

Abstract: A heat-resistant heterocyclic polymer consisting of units of the general formula ##STR1## wherein R, R.sup.1 and X are as defined hereinbelow anda method for producing heat-resistant heterocyclic polymers, consisting in that, at a temperature of 90.degree. to 400.degree. C., there is conducted a reaction of polyfunctional nitrile-containing compounds with polyfunctional isocyanates.The proposed polymers are stable at temperatures from 300.degree. to 350.degree. C. Materials based thereon are capable of retaining their properties at a temperature of up to 400.degree. C. for long periods of time. The method is simple and can be effected without isolation, purification or drying the polymer, which allows combining the process of producing the polymer with that of producing a finished article.

Abstract: A urethane prepolymer repair system is provided by an isocyanate-terminated polytetramethylene ether glycol prepolymer of about 3,500-10,500 molecular weight that cures to an elastomer upon exposure to atmospheric moisture and is packaged in a container capable of repeatedly dispensing the prepolymer with minimal exposure to ambient air, such as a collapsible tube or caulking gun cartridge. The repair system is used to build up worn down soles and heels of footwear, repair separations of soles and heels from shoe tops, and hundreds of other uses.

Abstract: A coating or molding composition including a polyisocyanate and an unsaturated imide, and having a ratio of total isocyanate functions to total polymerizable double bonds in the imide in the range of from 0.3 to 15, is addition polymerized to hard, imide group containing polymers characterized by the recurring unit: ##STR1## Coatings and shaped articles formed from such polymers are hard, tough, thermally stable, solvent resistant and are good insulators.

Abstract: A two component polyurethane coating system is disclosed in which the pot life is extended while retaining rapid cure. The system employs a first component which is a solution of a soluble resin containing active hydrogen atoms capable of reacting with isocyanate functionality, and said first component has dispersed therein an amine catalyst for the reaction absorbed in a molecular sieve having a pore size large enough to absorb the amine catalyst. The molecular sieve minimizes the catalytic effect of the amine catalyst when the two components are mixed until after the absorption of atmospheric moisture forces the sieve to release the catalyst to speed the cure. The second component comprises a solution of an organic polyisocyanate, this solution containing an organotin accelerator which has been deactivated with acetic acid or formic acid which minimizes the accelerating effect of the accelerator when the two components are mixed until after vaporization of the acid frees the accelerator to speed the cure.

Abstract: Polyimide-amide-carboxylic acids produced by reacting an aromatic diamine with an aromatic tetracarboxylic acid dianhydride in amounts of 1.5 to 2.0 moles of the latter per mole of the former in the presence of an inert solvent, and reacting the resulting intermediate reaction product with an aromatic diisocyanate in about equivalent amounts at a temperature of 50.degree. to 100.degree. C. while removing generated carbon dioxide from the reaction system are good in heat resistance, wear resistance, chemical resistance, etc.

Abstract: Polyamideimides prepared by polycondensation of trimellitic anhydride, diphenyl methane diisocyanate and an isocyanate mixture are provided. These preparations exhibit low viscosity in high-solids solutions and are useful as wire enamels and topcoats over polyester and polyesterimide base coats.

Abstract: A method of forming a hydrophilic urethane prepolymer useful in consolidating aggregate material comprises the steps of adding an isocyanate compound to a hydrophilic polyether or polyester compound which has been heated to such a temperature that the temperature of the reactants after addition of isocyanate is at least as high as about 120.degree. C. The resulting urethane prepolymer may be reacted with an aqueous slurry of unconsolidated aggregate material, such as peat, to form a consolidated aggregate product, such as a plant growth-supporting rooting medium.

Abstract: Novel, finely divided, redispersible dispersions of high melting polyesters in low melting polyhydroxyl compounds are disclosed. Disclosed also is a process for their preparation and their use as polyol components containing fillers in the production of cellular or non-cellular polyurethanes.

Abstract: Polyurethane molding compositions are disclosed which contain diisocyanates and polyols and/or polyurethane prepolymers and sorbic acid or cinnamic as a setting catalyst. A process for preparing such compositions is also disclosed. These compositions give a rapid initial hardening and therefore mold release properties, which contribute to increased production speeds. Moreover, the acids used are physiologically safe, so that the process may be used for the production of objects used in medical science. The acids may also be used in a physiologically safe mixture with a heavy-metal containing catalyst.

Abstract: This invention relates to a process for the production of optionally foamed polyurethane plastics, particularly shaped articles, using certain denatured biomasses as reactive fillers. The fillers in question comprise biomasses based on microorganisms and the derivatives and decomposition products of microorganisms, particularly biologically purified sludges, which have been deodorized and irreversibly denatured by reaction with isocyanates and/or carbonyl compounds and compounds capable of aminoplast and/or phenoplast formation.

Abstract: A process for preparing aqueous polyurethane dispersions has been discovered which comprises(a) forming a polyurethane solution by reacting an organic polyisocyanate in the presence of a solvent with(i) an acrylic ester diol having a molecular weight of between 146 and 3,000;(ii) an organic polyhydroxyl compound other than (i) having a molecular weight between 400 and 5,000 selected from the group consisting of polyester polyols, polyether polyols, polycarbonates, polylactones, and mixtures thereof; and(iii) a chain extender having a molecular weight between 62 and 400 selected from the group consisting of diols, triols, diamines, aminoalcohols, and mixtures thereof;(b) forming an anionic polyurethane addition product by reacting said polyurethane solution with a mercaptocarboxylic acid salt in the presence of a solvent;(c) adding water; and(d) removing the solvent.The dispersions can be used in a variety of applications. For instance, they can be used to prepare films, coating, and binders.

Abstract: A process is provided for preparing storage stable, aqueous dispersions of oligourethanes or polyurethanes in admixture with auxiliary agents and additives which are not soluble nor dispersible in water. The oligourethanes or polyurethanes are rendered dispersible in water by incorporating ionic and/or non-ionic hydrophilic groups. In order that the final product remains storage stable, the auxiliary agents or additives are added to the oligourethanes or polyurethanes before they are dispersed in water.

Abstract: This invention relates to a process for the preparation of finely divided, stable and relatively low viscosity dispersions of ionic polyisocyanate polyaddition products in compounds having hydroxyl groups by reacting(1) organic polyisocyanate with(2) compounds having primary and/or secondary amino groups and/or primary hydroxyl groups in(3) compounds having at least one hydroxyl group,with the proviso that compounds (3) have secondary hydroxyl groups if compounds with primary hydroxyl groups are used as compound (2), and further characterized in that at least one of the components (1) or (2) has groups which are ionic and/or capable of salt formation.

Abstract: This invention relates to a process for the in situ preparation of stable dispersions of polyisocyanate-polyaddition products in hydroxyl containing compounds as dispersing agent by a process which comprises reacting(1) organic polyisocyanates with(2) compounds having primary and/or secondary amino groups and/or primary hydroxyl groups and/or ammonia, in(3) compounds having at least one hydroxyl group, whereincompounds (3) have secondary hydroxyl groups in cases when compounds (2) have primary hydroxyl groups and wherein the components are reacted in the presence of more than 4% by weight of water, based on the quantity of reaction mixture including water.

Abstract: This invention relates to a process for the production of non-cellular polyurethane ureas elastomers using a chain-extender mixture produced from asymmetrically alkyl-substituted anilines by condensation with formaldehyde. The chain-extending agents used in the instant invention show medium reactivity to compounds containing isocyanate groups. These chain-extending agents may be processed both in high-pressure and in low-pressure metering and mixing units because they are either liquid at room temperature or can be melted at relatively low temperatures (below 55.degree. C.). The homogeneous, i.e. non-cellular, polyurethane urea elastomers obtained in the instant invention are distinguished by having excellent mechanical properties.

Abstract: Cold-setting, polyurethane-based molding material binder for producing molds and cones comprising phenolic polyol and a polyisocyanate characterized in that the polyol is dissolved in a polar high boiling solvent which has a Hansen hydrogen bonding solubility parameter of at least 3.5.

Abstract: A process for the production of modified polyhydantions by reacting polyglycine acid derivatives with optionally masked polyisocyanates with the addition of cyclic anhydride compounds containing at least one further functional group capable of condensation in lactones as solvents.

Abstract: The instant invention is directed to a novel method for improving the color stability of thermoplastic polyurethanes and the polyurethanes produced thereby. The invention broadly consists of adding relatively small amounts of a specified hydroxyl group containing additive to the thermoplastic polyurethane reaction mixture. The additive may be added before, or during production of the thermoplastic polyurethane. In general the additive is defined as:(a) having a molecular weight of 400 or less, and(b) containing from 2 to 4 aliphatic hydroxyl groups, with at least 2 of the hydroxyl groups being vicinal, and with the vicinal hydroxyl groups being primary and/or secondary.

Abstract: This invention relates to control of particle size of solid, discrete, hydrophilic, crosslinked polyurethane particles formed from a composition which comprises(a) a water reactant;(b) a prepolymer comprising at least one isocyanate-capped polyol having a reaction functionality of at least two, the total of said polyol present having an ethylene oxide content of at least 40 weight percent before capping;(c) a water-soluble solvent for (b) and(d) when the reaction functionality of (b) is two, a crosslinking agent containing at least three functional groups, the volume ratio of (a):(b) being at least 2:1.

Abstract: Poly(thio)hydantoins are prepared by reacting an iso(thio)cyanate having at least two iso(thio)cyanate moieties with a compound of the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each represents hydrogen, halogen, a C.sub.1 -C.sub.20 aliphatic group, a C.sub.7 -C.sub.20 aliphatic-aromatic group, a C.sub.6 -C.sub.20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom;A represents CN, COR, substituted or unsubstituted C.sub.1 -C.sub.20 aliphatic group, C.sub.7 -C.sub.20 aliphatic-aromatic group, C.sub.6 -C.sub.20 aromatic group or a heterocyclic group having from 4 to 16 ring members and at least one N, O or S atom wherein the substituents are NO.sub.2, COOR.sub.4, CN, CO or OH; R and R.sup.4 are selected from the definition of R.sup.1 and R.sup.2 with the exclusion of halogen;M represents OH or ##STR2## and R.sup.6 represents hydrogen, unsubstituted or substituted C.sub.2 -C.sub.20 aliphatic, C.sub.5 -C.sub.12 cycloaliphatic, C.