Dynamit Nobel Aktiengesellschaft

Egon N Petersen

Hermann Richtzenhain

Norbert Vollkommer

Werner Schmidt

Herbert Klinkenberg

Wilhelm Vogt

Gerhard Bier

Georg Blumenfeld

Klaus Schrage

Dagmar Kottek

Klaus-Dieter Steffen

Gerhard Schade

Georg Blumfeld

The invention relates to halogenous polyesters with the recurrent general formula ##STR1## in which at least part of the R's, e.g. 1 to 100 mole-%, preferably 100 mole-%, or 2 to 10 mole-%, are of the general formulas ##STR2## and 0 to 99 mole-%, preferably 0 or 90 to 98 mole-%, of the R's correspond to a phenylene radical and/or a naphthylene radical and/or an alkylene radical of 3 to 10 carbon atoms and/or a cycloalkylene radical, and the R's represent an organic moiety which is contained in bivalent saturated alcohols and corresponds to a branched or unbranched saturated alkylene radical of 2 to 10 carbon atoms and/or to a cycloalkylene radical and/or which is derived from an alkyleneterephthalate containing hydroxyl groups, preferably an oligomeric ethyleneterephthalate and/or an oligomeric propyleneterephthalate and/or an oligomeric butyleneterephthalate, wherein Z represents the groups ##STR3## and X represents hydrogen, bromine or chlorine, wherein at least some of the X's are bromine or chlorine, and in which polyesters, in some cases, a portion of the R's are residues of unsaturated dicarboxylic acid derivatives which, together with ethylenically unsaturated comonomers, preferably styrene, are capable of forming peroxide-curable unsaturated polyester resin (UP resin) solutions, and their preparation as well as their use as fire-retardant molding compositions or articles, and also dicarboxylic acid esters some of which can be used in the preparation of the polyesters as well as the preparation of these dicarboxylic acid esters. Preferably the xylene nucleus in (2) is substituted by Br.sub.4.0 to 2.8 and Cl.sub.0 to 1.2.

Bis-carbalkoxy compounds and their preparation

Halogen-containing bis-acrylates and bis-methacrylates corresponding to the formula ##STR1## in which R represents hydrogen or a methyl group and X represents chlorine and/or bromine, are provided as well as a process for producing such compounds. The compounds are useful for the formation of polymers and copolymers and as cross-linking agents. Also included in the invention are the polymers and copolymers based on the above-described halogen-containing bis-acrylates and bis-methacrylates, methods for the production of said polymers and the use of said polymers as flame proofing agents, etc.

Halogen-containing unsaturated bis-esters and polymers and copolymers

p- and o-chloromethylbenzoic acid phenyl esters and thiophenyl esters of the formula ##STR1## wherein X represents oxygen or sulfur and R the radical of a mononuclear or polynuclear phenol or thiophenol which is unsubstituted or which bears additional substituents which may include the substituent ##STR2## wherein X is as above. The components can be produced by reacting p- or o-chloromethylbenzoyl chloride with univalent or polyvalent, mononuclear or polynuclear phenols or the thiophenols in the presence of inert solvents and tertiary amines in a catalytic or stoichiometric amount, amides in a catalytic amount, or in an aqueous alkaline medium.

Chloromethylbenzoic acid esters of phenols

Process for the side-chain chlorination of aromatic compounds completely halogenated in the nucleus, containing methyl groups, and having the general formulas: ##STR1## wherein y=1 or 2, z=0 to 1, x=6-(y+z), n=0 to 8 and k=(8-n) and the methyl groups are, respectively, in the ortho, meta or para position to one another and in the p-position to the oxygen bridge, by thermal chlorination in the liquid phase. The bis-monochloromethyl compounds of formula (II) are novel compounds. The chlorination products are useful as intermediates.

Process for the side-chain chlorination of perhalogenated methyl

A polymer having as a component thereof a moiety corresponding to a monomer having the following formula ##STR1## wherein n=0 or 1, X is bromine, chlorine or a mixture thereof and R represents hydrogen or methyl, a method of preparing the same and the use of such a polymer, including a copolymer thereof in a plastic composition containing a normally flammable plastic.

Acrylate-based polymers and copolymers and their use as flameproofing

Linear or unsaturated polyesters prepared from bis-carbalkoxy compounds

Halogen-containing bis-acrylates and bis-methacrylates corresponding to the formula ##STR1## in which R represents hydrogen or a methyl group and X represents chlorine and/or bromine, are provided as well as a process for producing such compounds. The compounds are useful for the formation of polymers and copolymers and as a cross-linking agents. Also included in the invention are the polymers and copolymers based on the above-described halogen-containing bis-acrylates and bis-methacrylates, methods for the production of said polymers and the use of said polymers as flame proofing agents, etc.

Halogen-containing unsaturated bis-esters

Tetrahaloxylene diesters of formulas 1 and 2: ##STR1## wherein R= hydrogen or a methyl group, and each X is bromo, with the proviso that some of the X's can be chloro. The compounds are useful as flame retardants for plastics.

Tetrabromoxylylene diacrylates and substituted acrylates

Ar-octahalogendiphenylether-4,4-dimethanols

A polymer having as a component thereof a moiety corresponding to a monomer having the following formula ##STR1## WHEREIN N = 0 OR 1, X is bromine, chlorine or a mixture thereof and R represents hyrogen or methyl, a method of preparing the same and the use of such a polymer, including a copolymer thereof in a plastic composition containing a normally flammable plastic.

Acrylate-based polymers and their use as flameproofing agents

A polymeric formal having the general formula ##STR1## wherein p is 0 or 1, n is a positive integer from 2 to 200 and R represents optionally halogen-substituted straight-chained or branched-chained alkyl radicals having 3 to 8 carbon atoms, an aryl radical or an aralkyl radical which can be substituted on one or both sides with alkyl or hydroxyalkyl ether groups; improved methods for the preparation of such formals, tetrabromoxylylene-bis-(.beta.-hydroxyethylether) compounds employed in the preparation of such formals and the use of such polymeric and oligomeric formals as flame retardant agents in plastic compositions especially thermoplastic and polycondensation plastic compositions.

Polymeric and oligomeric formals

Aryl sulfonic acid esters of the formula ##STR1## wherein R.sup.1 represents hydrogen, alkyl groups of 1 to 8 carbon atoms, bromine or chlorine, R.sup.2 represents R.sup.1 or the group ##STR2## Hal represents bromine or chlorine, x the numbers 2 to 4, n the numbers 3 to 5, y the numbers 4-x; m = 5-n, R.sup.3 represents bromine, chlorine or the group ##STR3## and Z represents --O--, --S--, ##STR4## alkylene with 1 to 4 carbon atoms, or alkylidene; a process for their product and their use as a flame retardant, especially for polyolefins.

Arylsulfonic acid bromophenyl esters, their preparation, and their use

Aryloxymethylbenzoic acid phenyl ester of the formula ##STR1## wherein X represents oxygen or sulfur, and each R represents residue of a mononuclear or polynuclear phenol which can be substituted. The ester can be produced by reacting the corresponding chloromethylbenzoic acid phenyl ester with the alkali salt of the phenol corresponding to the aryl group of said aryloxymethyl group. The products are useful as additives for plastics to impart flame resistance thereto.

Halogen-containing aromatic ether-ester fire-retardants for plastics

A flame stabilized molding composition comprising: 1. A polyester which is the condensation product of an aromatic dicarboxylic acid, acid halide or ester and an aliphatic diol having more than 2 atoms in the chain, and 2. 1,4-bis-(.beta.,.gamma.,.gamma.-trichloroallyl)-2,3,5,6-tetrachlorobenzene of the formula ##STR1## SAID 1,4-BIS-(.beta.,.gamma.,.gamma.-TRICHLOROALLYL)-2,3,5,6-TETRACHLOROBENZENE PRESENT IN SAID MOLDING COMPOSITION IN AN AMOUNT OF 5-30 WEIGHT PERCENT, PREFERABLY 10-25%, BASED UPON THE WEIGHT OF SAID POLYESTER.

Difficultly inflammable polyester molding compositions

An aromatic polynuclear, halogenated, aromatic benzyl ether of the formula ##STR1## WHEREIN W is a chlorine or bromine atom or a methyl radical or the radical --CH.sub.2.Z, said radical W being disposed in the ortho, meta or para position with respect to the CH.sub.2.Z radical, Hal represents a chlorine or bromine atom, n is 0 to 4 and Z represents a phenoxy radical of the general formula ##STR2## wherein X is a chlorine or bromine atom, R is a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms, a is 2 to 5 and b is (5-i a); a process for producing such polynuclear halogenated benzyl ether by contacting a benzyl halide of the general formula ##STR3## wherein Hal and n have the previously assigned significance, X is a chlorine or bromine atom, Y is the same as CH.sub.2 X or is a hydrogen or chlorine atom or a methyl radical and is disposed in the ortho, meta or para position with respect to the radical --CH.sub.2 X, and a phenolate of a halogen phenol which halogen phenol has the formula ##STR4## WHEREIN X, R, a and b have the previously assigned significance, in a glycol monoalkyl ether reaction medium until the ether is formed and thereafter isolating the ether.

Growing community of inventors

Neunkirchen-Seelscheid, Germany

Egon N Petersen