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United States Patent Office 3,321,553 United States Patent Office Patented May 23, 1967 2 3,321,553 POLYESTER COMPOSITIONS CONTAINING polyhydric alcohol containing aliphatic carbon-to-carbon HALOGEN AND PHOSPHORUS unsaturation and (2) a polycarboxylic compound con Nicodemus E. Boyer, Parkersburg, W. Va., and Raymond taining aliphatic carbon-to-carbon unsaturation, disclosed R. Hindersinn, flewiston, and Claude Thomas Sean, Jr., and claimed in U.S. Patent 2,779,700, issued Jan. 29, 1957; Niagara Fais, N.Y., assignors to Hooker Chemical and (c) the reaction of (1) a polyhydric alcohol adduct Corporation, Niagara Fails, N.Y., a corporation of of hexahalocyclopentadiene with (2) another alcohol con New York taining aliphatic carbon-to-carbon unsaturation and (3) a No Drawing. Fied June 10, 1966, Ser. No. 556,546 polycarboxylic acid disclosed and claimed in U.S. Patent 14 Ciainas. (C. 260-862) 2,863,795, issued Dec. 6, 1958. An alternate method for This is a continuation-in-part of copending application O incorporating an adduct of hexahalocyclopentadiene into Ser. No. 158,105, filed Dec. 8, 1961, now Patent No. a polyester resin involves reacting an unsaturated poly 3,278,464. ester resin with a copolymerizable compound containing This invention is directed to a highly, fire retardant an adduct of hexahalocyclopentadiene, such as disclosed polyester resinous composition having a synergistic com and claimed in U.S. Patent 2,783,215, issued Feb. 26, bination of halogen and phosphorus. Fire retardant poly 1957. The polyester resins containing the polycarboxylic ester resins containing halogens are well known, as are and polyhydric alcohol adducts of hexahalocyclopenta fire retardant polyester resins containing phosphorus. diene can be modified by incorporating therein saturated However, it was unexpectedly found that the polyester carboxylic acids and anhydrides, as disclosed and claimed compositions of the instant invention, which contain both in U.S. Patent 2,890,144, issued June 9, 1959, and U.S. halogen and phosphorus, provide a synergistic effect on 20 Patent 2,898,256, issued Aug. 4, 1959. When used in this the fire retardance of the composition that is unpredictable specification, the term polycarboxylic compound refers from the fire retardance provided by either component to the polycarboxylic acids, acid anhydrides, acide halides alone. and acid esters. In accordance with the invention there are provided polyester resin compositions comprised of (A) an unsat 25 A variety of unsaturated acids, acid halides, acid an urated polyester resin having reacted therein an adduct hydrides, and acid esters which contain aliphatic carbon of hexahalocyclopentadiene and a dienophile having a plu to-carbon unsaturation can be used in either the prepara rality of functional groups capable of esterification, where tion of the polycarboxylic adducts of hexahalocyclo in the halogen is selected from at least one member of pentadiene or to provide the unsaturation in the linear the group consisting of fluorine, chlorine and bromine; 30 polyester molecules. The polycarboxylic acids and the and (B) an unsaturated polyester resin having a reactive corresponding acid halides, esters, anhydrides, and acid phosphite reacted therein in an amount that is insufficient esters can include maleic, chloromaleic, ethylmaleic, to react with all of the carbon-to-carbon double bonds of itaconic, citraconic, Zeronic, pyrocinchoninic and acety the unsaturated polyester resin. The polyester resin com lene dicarboxylic, either alone or in mixtures. positions of the invention are generally converted to 35 Illustrative of the unsaturated polyhydric alcohols which thermoset resinous compositions by cross-linking the com contain aliphatic carbon-to-carbon unsaturation and which position with an ethylenically unsaturated monomer con can be used either in preparing the adducts of hexahalo taining the structure cyclopentadiene or in providing the unsaturation in the 40 linear polyester molecules are compounds such as butene in the presence of a free radical catalyst. diol, pentene diol, the unsaturated hydroxy ethers such The halogen-containing polyester resin component of as allyl or vinyl glycerol ethers, allyl or vinyl penta the compositions of the invention comprises a polym erythritol ethers and the like. erizable, linear polyester resin, comprised of the reaction The preferred polycarboxylic adduct is 1,4,5,6,7,7-hexa product of a polycarboxylic acid and a polyhydric alco 45 chlorobicyclo- (2.2.1) - 5 - heptene-2,3-dicarboxylic acid hol, said resin having olefinic copolymerizable unsatura (commonly known as chlorendic acid), but other poly tion, a component of said polyester resin containing an carboxylic adducts of hexahalocyclopentadiene can be adduct of hexahalocyclopentadiene wherein the halogen used. Among these are the following: is selected from the group consisting of fluorine, chlorine, bromine and mixtures thereof. The hexahalocyclopenta 50 1,4,5,6,7,7-hexachlorobicyclo-(2.2.1)-5-heptene-2,3- diene is preferably adducted with a compound selected dicarboxylic anhydride (chlorendic anhydride); from the group consisting of a polycarboxylic compound 1,4,5,6,7,7-hexachloro-2-methyl-bicyclo-(2.2.1)-5-hep containing aliphatic carbon-to-carbon unsaturation and a tene-2,3-dicarboxylic anhydride; polyhydric alcohol containing aliphatic carbon-to-carbon the mono-ethyl ester of 1,4,5,6,7,7-hexachlorobicyclo unsaturation. 55 (2.2.1)-5-heptene-2,3-dicarboxylic acid; The preferred unsaturated polyesters are the reaction 1,4,5,6-tetrachloro-7,7-difluorobicyclo-(2.2.1)-5-heptene products of (1) an adduct of hexahalocyclopentadiene 2,3-dicarboxylic acid; and a polycarboxylic compound containing aliphatic 1,4,5,6-tetrachloro-7,7-dibromobicyclo-(2.2.1)-5-hep carbon-to-carbon unsaturation, (2) a polycarboxylic com tene-2,3-dicarboxylic acid; pound containing aliphatic carbon-to-carbon unsaturation 60 5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8- and (3) a polyhydric alcohol. Such a product is dis methano-2,3-naphthalene dicarboxylic acid closed and claimed in U.S. Patent 2,779,701, issued Jan. 1,4,5,6,7,7-hexachlorobicyclo-(2.2.1)-5-heptene-2,3- 29, 1957. Other methods of incorporating either a poly dicarbonyl chloride. carboxylic or polyhydric alcohol adduct of hexahalocyclo 65 The polycarboxylic compound suitable for adduction with pentadiene include: (a) the reaction of (1) a polycar the hexahalocyclopentadiene are the acids, anhydrides, boxylic adduct of hexahalocyclopentadiene and (2) an acid halides and acid esters. unsaturated polyhydric alcohol containing aliphatic AS aforesaid, a second method of making the polyester carbon-to-carbon unsaturation, disclosed and claimed in resins of this invention comprises incorporating com U.S. Patent 2,863,794, issued Dec. 9, 1958; (b) the reac 70 bined halogen into the polyester in the form of an adduct tion of (1) an adduct of hexahalocyclopentadiene and a of hexahalocyclopentadiene with a polyhydric alcohol con 3,3 21,553 4. 3. less than 30. In the foregoing formulas, each R is inde taining olefinic or carbon-to-carbon unsaturation. Among pedently selected from the group consisting of alkyl, cyclo the adducts which can be so used are: alkyl, alkenyl, aryl, alkylaryl and arylalkyl, halo-sub 2,3-dimethylol-1,4,5,6,7,7-hexachlorobicyclo-(2.2.1)- stituted, alkoxy-substituted, aryloxy-substituted or other 5-heptene; t Substituted organic radicals of the foregoing group con 2,3,-dimethylol-1,4,5,6,7,7-hexabromobicyclo-(2.2.1)-5- ) taining substituents which do not interfere in the reaction heptene; with the ethylenically usaturated polyester. The preferred 3-(1,4,5,6-tetrachloro-7,7-difluorobicyclo-(2.2.1)-5- Substituted groups are haloalkyl, alkoxyalkyl and aryloxy heptene-2-yl)-methoxy-1,2-propane diol; and alkyl. The preferred phosphorus compounds for prepar 3-(1,4,5,6,7,7-hexachloro-(2.2.1)-5-heptene-2-yl)- ing the phosphonated polyesters are the lower alkyl methoxy-1,2-propane diol. 10 phosphites such as trimethyl phosphite and dimethyl phos phite and the lower alkenyl phosphites, such as triallyl The preparation of these compounds is disclosed in U.S. phosphite and dially phosphite. Other specific phosphites Patent 3,007,958. that can be used are those where the R radicals are meth The saturated polycarboxylic compounds useful in the yl, ethyl, isopropyl, butyl, hexyl, n-octyl, 2-ethylhexyl, preparation of the polyesters can be aliphatic, cycloali 5 decyl, hexadecyl, phenyl, benzyl, tolyl, cyclohexyl, allyl, phatic, aromatic or heterocyclic. Illustrative of these poly crotonyl, beta-chloroethyl, beta-bromoethyl, beta-me carboxylic acids, acid halides, acid anhydrides and acid thoxyethyl, beta-ethoxyethyl, beta-butoxyethyl, beta esters include phthalic, isophthalic, terephthalic tetra phenoxyethyl, tetrahydrofurfuryl, tetrahydropyranyl, and chlorophthalic, adipic, succinic, and mixtures thereof. mixtures thereof. Generally, it is preferred that no more Suitable saturated polyhydric alcohols for use in the 20 than two aryl substituents be utilized. In general, the preparation of the polyester resins include ethylene gly length of the carbon chains or number of carbon atoms col, diethylene glycol, propylene glycol, dipropylene gly in the aryl nuclei in the organic radicals of the phophorus col, butane diol, pentane diol, hexane diol, glycerol, man compound is not critical and may vary over wide ranges. nitol, sorbitol, and mixtures thereof. The lower limit is the lowest possible number of carbon The temperature for the reaction between polyhydric 25 atoms such as one carbon atom in the alkyl groups and alcohols and polybasic acids ranges from about 100 to six carbon atoms in aryl groups and the upper limit is 200 degrees centigrade, although higher or lower tem any practical number. However, a higher percent by peratures can be used. Esterification catalysts such as weight of phosphorus can be incorporated into the poly para-toluene sulfonic acid, benzene Sulfonic acid, beta mer in instances where the organic radicals attached to naphthalene sulfonic acid and the like, or amines such as 30 the phosphorus atoms in the organic radicals R preferably pyridine, triethyl amine, quinoline and the like can be contain from 1 to about 6 to 8 carbon atoms.
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