Document 3Nqyr41X4R8R4zjK2a4BJwRBE

Monsanto I m iM <IIAMI n I tM.AIION >ATE SUBJECT REFERENCE TO Patent Department - General Offices December 3, 1969 Patent and Literature Survey AROCLOR and Biphenyl HSB to JEM, 12-9-68 H. S. Bergen HBERG ' CC _Benianus PBENI / W. A. Kuhn - WKUHN R. M. KountZ - RKOUN J. E. Maurer D. A. Olson - DOLSO W. R. Richard - WRICH ANNISTON - W. B. Papageorge ANNISTON - H. L. Williams The Patent Department has completed the survey you requested on recent patents and literature relating to polyphenyls and chlorinated polyphenyls to determine current areas of commercial interest and to develop a picture of "who is doing what" in this area. The scope of the survey included the manufacture and chlorination of polyphenyls and uses of the chlorinated material. Particular emphasis was placed in the pyrolysis of benzene, chlorination of biphenyl, and uses of AROCLOR, as being of particular business interest. The patent art was searched back to 1950. This cut off date was selected on the basis that the search would include all unexpired patents and that any patents issuing prior to 1950 and still of current interest would be well known in the business group. The literature search covered a period from 1965 to 1968, the last three years reported in Chemical Abstracts. Earlier searching did not appear justified considering that important novel work published prior to 1965 would be expected to be disclosed in recent patent literature. A patent survey reported in 1958 dealt at length with the history and development of the AROCLOR business, and discussed the possible areas in which Monsanto might improve its patent position. The information contained in that report is intended to supplement the present search results, and a copy of the report is appended hereto. Patents and literature relating to the manufacture of biphenyls and chlorinated biphenyls are contained within a relatively narrow field of search and can be collected DSW 269194 STLCOPCB4054187 H. S. Bergen 2 December 3, 1969 without great difficulty. Information on the use of these materials, however, is scattered throughout the literature and patent art, and it is impossible to con duct a search with a high level of confidence that all pertinent references have been found. This is particularly true for a versitile material like AROCLOR which is found in many widely divergent applications. Because of the complexity of uncovering use patents, we resorted to computer searching by IFI (Information for Industry). A check of these search results against our collection of known references gave evidence that the machine searching technique is not sufficiently dependable to be used alone, but that it is a valuable contributor to the total search effort. Accordingly, the results contained herein are not represented as being an allinclusive collection of the prior art with no reference omitted, but certainly a good segment of the pertinent art is reported and should provide a basis for examining the activities of others in this field. In the event that a critical study should be required in any particu lar area for legal or business reasons, this collection of art can be used as a basis from which a complete study can be developed. The search was organized according to the Index which is appended hereto together with abstracts of all the pertinent patents and literature references collected in the search. The discussion which follows is organized according to the main headings of this index. Numbers in parenthesis following section headings desig nate the number of references included in that section. DISCUSSION I. Manufacture of Diphenyl A. Pyrolysis of Benzene (13) Recent patents have been issued to Dow Chemical and Progil. Dow 3,262,983 specifies the use of certain nickel chromium steels to inhibit carbon formation in the reactor. This is Dow's equivalent to Monsanto 3,228,994 which specifies reactor alloys such as Hastalloy X. Dow 3,359,340 teaches the pyrolysis of benzene containing small amounts of phenol in the presence of copper. Three older Dow patents are listed for general interest. DSW 269195 STLCOPCB4054188 H. S. Bergen 3 December 3, 1969 Progil 3/112,349 and 3,227,525 disclose conditions and apparatus for the pyrolysis of benzene which have already been given considerable attention by Monsanto. Progil 3,207,799 concerns the deliberate preparation of terphenyls by recycling diphenyl through the pyrolysis zone. None of these patents are considered to threaten Monsanto's position. In addition to the patent mentioned above, Monsanto 2,702,307 describes a basic process for pyrolysis in terms of temperature and vapor flow rate. These two patents are the only ones on pyrolysis issuing to Monsanto since 1950. B. Other Routes (16) Other routes to biphenyl include mainly liquid phase reactions and hydrodealkylation of petroleum fractions. Gulf 3,401,207 and Shell 3,145,237 concern the catalytic coupling of benzene. Universal Oil 3,274,277 describes an interesting process for the reaction of benzene and ethylene under pressure in the liquid phase. Phillips 3,435,084 describes the preparation of biphenyl by hydrodealkylation of certain petroleum fractions. Ashland 3,055,956 and 2,951,886, and Atlantic 3,160,671 disclose processes for preparing benzene by a hydrode alkylation process which presumably could be controlled to produce biphenyl. Monsanto holds four patents on the preparation of terphenyls by arylation of aromatics. One of these, 3,231,629, is reported to be a basic MCL patent. C. Refining and Purification (4) Dow 3,363,020 is a recent issue which refines and decolorizes biphenyl by the addition of sulfuric acid followed by distillation. Also of interest is unassigned Czech, patent 124,741 which treats diphenyl with a mixture of CaO and Perlite to improve the dielectric constant. 05^269196 STLCOPCB4054189 II. S. Bergen 4 December 3, 1969 II. Chlorination (13) d'Ugine 3,029,295 (Fr. 1,387,233) describes a process for the vapor phase chlorination which is reported to provide high purity material in good yield. This patent could have an adverse affect on Monsanto's business interests and is presently the subject of separate validity study. Liquid phase chlorination of polyphenyls is disclosed in two patents to Pennsalt; 2,859,252 describes chlorination by reaction with benzene hexachloride and 2,812,370 con cerns recovery of the AlClj catalyst used in the reaction. Texaco 3,358,040 is directed to the preparation of chlorinated biphenyls and biphenyl ethers from substituted diphenyls and biphenyl ethers from substituted diphenyls. French 1,448,922 to Sandoz describes chlorination of biphenyl in a TiCl4 solvent. The remaining references in this section are of general interest. Monsanto patents in this area issuing since 1950 include two on the preparation of AROCLOR by decomposing an aromatic sulfonyl halide, and one on the chlorination of m-diphenylbenzene. Monsanto's basic patents to the chlorination of biphenyl were issued prior to 1950 and are expired. III. Functional Fluids A. Heat Transfer (23) A number of references to the use of polyphenyls as coolants for nuclear reactors were found in the period of 1959 to 1964. From our own efforts in this area, we know that there is currently little interest in organic coolants in this application except for work being done in Canada. The diminished interest accounts for the fact that more recent references were not found. Seven patent references issued to different companies are abstracted in the appendix, all dealing with stabilizers which increase the resistance of the polyphenyls to radia tion demage. DSW 269197 STLCOPCB4054190 H. S. Bergen 5 December 3, 1969 Five literature references also abstracted are concerned with general evaluation of different mixtures for radiation resistance and heat transfer coefficients. An interesting publication by the U. of British Columbia discusses the use of AROCLOR as a direct-contact heat exchange agent for the condensation of steam in a packed column. The direct contact technique was claimed in Monsanto 3,249,152 where AROCLOR was sprayed into exhaust gas and then contacted with water to transfer the heat collected. There may be a possibility for commercial exploitation of this approach to heat transfer. Also of general interest is a recent patent to General Electric (3,415,896) for preparing substituted biphenyls by a catalytic transfer hydrogenolysis. These compounds are reported to be useful as high temperature heat transfer fluids. Monsanto has four patents to stabilized fluids for nuclear reactor use, and two to the process for reclaiming used fluids by removing or cracking the high boilers formed by exposure to radiation. B. Dielectrics (24) Emphasis in dielectric compositions is on finding new stabilizers and acid scavengers for the AROCLOR, with the favorite scavengers being epoxy compounds. General Electric and Westinghouse each have obtained patents to this type scavenger. Sprague Electric has two older patents (1957-1959) on compositions of AROCLOR plus butadiene polymer in tetra(2-ethylhexyl)orthosilicate. These patents are not seen to be of any immediate concern to Monsanto. Of more recent interest, duPont 3,200,077 claims a mixture of fluoroalkyl benzoate and AROCLOR as a dielectric composition. Progil 3,194,766 is directed to a specific mixture of dichloro-,trichloro- and tetrachloro diphenyls. Monsanto has had eleven patents issue since 1950 on scavengers for AROCLOR dielectrics. We also have one patent to combinations of tri- and tetrachloro biphenyls, and another to the isomerization of dichlorobiphenyl to improved dielectric compositions. DSW 2691'98 STLCOPCB4054191 II. S. Bergen 6 December 3, 1969 It appears that the opportunity, is still open to patent halogenated diphenyl compositions where advantageous properties can be shown for specific mixtures of isomers and/or different chlorine contents. The crowded art makes conclusive evidence of unusual properties essential to the case, but it appears certain that more patents like Progil above will be issued to whoever makes the showing of desirable properties. C. Hydraulics (13) References which are specifically intended for use as hydraulic fluids are included in this section. Three recent patents to McDonnell Douglas claim fluids comprising chlorinated diphenyl ether with phosphate esters and/or chlorinated biphenyl. These fluids are not incorporated in the Commercial Enterprise. Bayer 3,282,847 claims a mixture of tetrachlorodiphenyl and TCP, a composition which is probably limited in its commercial utilization by present pollution considerations. Bayer 3,056,745 is to a combination of chlorinated diphenyl and polyoxyalkylene diol. Monsanto has had three patents issue on this subject matter since 1955. Additional cases including the PYDRAUL 312 composition are on file, but the Patent Office has been unwilling to grant broad claims to mere mixtures of known hydraulic fluid components. New patent issues in this crowded art will likely be restricted to rather narrowly limited compositions having unusual or unexpected properties clearly demonstrated by extensive experimental data. D. Lubricants (8) Biphenyls and halogenated biphenyls specifically intended for use in lubricants are generally restricted to the function of minor additives or to compositions for specialty applications. For example, Shell 3,297,574 employs chlorinated biphenyl as an EP additive in aliphatic ester lubes, and Standard 2,852,468 adds small amounts of AROCLOR to mineral oil. DSW 269199 STLCOPCB4054192 II. S. Bergen 7 December 3, 1969 In specialty applications, chlorinated biphenyl is used in pressure forming fluoroethylene polymers (duPont) and as a molding lubricant for ceramic powders. Monsanto has no patents issued since 1950 on this subject matter, and there does not seem to be much activity in this area of limited application. E. Thermodynamic Fluids (1) Monsanto 3,234,734 is the only patent found that suggests the use of biphenyl and AROCLOR as thermodynamic fluids. However, it has since been shown that these compounds are generally inferior to certain other compositions which are characterized by low entropy change as claimed in a pending application. F. Quenchants (2) Monsanto has two patents to the use of AROCLORS as quenchants in steel treating operations. No other references were found, and there does not seem to be any active interest in this area. IV. Adhesive Compositions A. Hot Melt (9) Chlorinated biphenyls are used in a variety of adhesive compositions where their plasticizing effect causes the composition to become tacky when heated, and to reset in cooling. National Starch 3,220,966 combines the biphenyl with olefin polymers. Other patents disclose polyamides and vinyls as the polymeric component. USP 3,282,811, purchased by Monsanto from National Starch, claims a copolymer of ethylene and vinyl acetate modified with a chlorinated terphenyl. This is Monsanto's only entry in this field. McLaurin-Jones 2,633,432 describes a novel multilayer heat activated adhesive where the biphenyl is separated from the polymeric component until the application of heat causes the two to merge into a single tacky layer. DSW 269200 STLCOPCB4054193 II. S. Bergen 8 December 3, 1969 For a comprehensive report on literature and patents concerning hot melt adhesives in general, see Report No. 3609, Literature Search on Hot Melt Adhesives and Coatings, by Paula Raizman, Nov. 1969. B. Other (9) A variety of glues and adhesives utilizing chlorinated biphenyl are disclosed in the art and include both synthe tic and natural base compositions. French 1,482,172 to Bericol broadly discloses the combination of pentachlorobiphenyl with polyamide, polyester, or natural rubber, but most of the U. S. patents are to specific compositions. The art suggests most of the adhesive development work is being conducted by individual manufacturers to fill their own needs. The opportunity for additional patent coverage in this area appears limited to narrow compositions having certain specific desirable properties well defined by experimental evaluation. V. Coating Compositions (20) Coating compositions are defined for purposes of this survey to include any combination of biphenyl or halogenated bi phenyl with a polymer resin, or other material which is applied to a substrate material for purposes of coating, sealing, or impregnating the substrate. This broad definition necessarily includes combinations where the biphenyl serves as a plasticizer, solvent, or flame retardant, and these sections should be considered as closely related to the present one. Most of the patent references found were prior to 1960 which indicates a recent decrease in activity in this area. The earlier references disclose the use of chlori nated biphenyl in compositions useful for insulating, rust preventing, concrete sealing, antistatic, and waterproofing. Eastman 2,635,970 describes a translucent paper impregnated with an ester-AROCLOR composition. Kodak and 3M each have recent British patents to thermographic papers employing AROCLOR as a heat sensitive material. DSVM 269201 STLCOPCB4054194 H. S. Bergen 9 December 3, 1969 Monsanto has three patents to the use of AROCLOR in a floor polish, a waterproofing coating, and an impregnant for cellulosics. The nature of the business requires to a large extent that products be tailored to solve specific problems. The result is that the majority of patents are issued to the ultimate consumers who solved their own problem, and there is little possibility or potential for anyone to develop a strong patent position. VI. Plasticizers (25) A number of references in the Russian literature were found discussing biphenyls and chlorinated biphenyls as plasticizers for poly(vinyl chloride). Specific objec tives were in dielectric films, radiation resistant paints, and adhesive coatings. One U. S. patent to Calresin disclosed the plasticization of PVC molding resins with AROCLOR. Other references disclose the combination of AROCLOR and polyesters, polyethylene, and various resins and rubbers. Eastman appears to be doing a considerable amount of work on the use of chlorinated biphenyls as antiplasticizers for polyesters and polycarbonates to increase film stiff ness. USP 3,240,735 and 3,254,047 issued to Eastman in 1966 claim this subject matter. Related articles published as late as 1967 indicate a continuing effort in this area by Eastman. Monsanto has one expired patent (2,506,014) describing the use of chlorinated biphenyl high boilers as plasticizers for polyvinylacetal compositions. VII. Solvents (7) Chlorinated biphenyl is widely used as a solvent in a variety of applications ranging from ink and dye carriers to epoxy cement strippers and organic reaction media. The patents have been obtained by the individual manufac turers for specific applications. The potential for obtaining additional patents in this area is limited to new specific applications, probably narrow in scope. DSW 269202 STLCOPCB4054195 H. S. 3ergen 10 December 3, 1969 VIII. Flame Retardants (9) The chlorine content of AR0CL0R makes it a natural additive to impart flame resistance to natural and synthetic polymeric materials. Patent protection for such use will depend on demonstrating benefits beyond those to be expected or calculated on the basis of the chlorine content. A natural approach is to claim combinations of AROCLOR with other materials which enhance the desired effect by a synergistic action. DuPont 3,418,267 is to a flame-resistant polyamide containing chlorinated biphenyl and a metal oxide. Badische 3,321,416 uses AROCLOR to impart flame resistance to polystyrene, and G.E. 3,154,515 incorporates AROCLOR in silicone rubber. Other applications mentioned in the references include textiles, polyurethane, and thermoplastic molding polymers. The trend toward ever greater use of plastics and synthetic fibers in consumer goods has created a large market for a variety of flame retardants, and it is conceivable that Monsanto could develop and patent flame retardants for selected end uses. Any work planned in this area should include brominated compositions as well as the chlorinated ones. The current opposition to chlorinated hydrocarbons due to pollution considerations, and the greater effectiveness and stability of the brominated materials enhances the potential of brominated flame retardants for commercial success. Monsanto presently has two patents issued in 1967 for the use of AROCLOR as a flame retardant for phenolic resins and for asphalt base coating compositions. IX. Miscellaneous (22) A variety of applications for biphenyls and chlorinated biphenyls which are not readily classified in any of the preceding sections are included herein. Uses include for example U.V. light stabilizers, antidusting agents, preservatives for citrus fruit, insecticides, U.V. light polarizers, and as a component in pigment pastes. DSW 269203 STLCOPCB4054196 H. S. Bergen 11 December 3, 1969 One unusual use of some interest described in Great Lakes Carbon 3,035,901 involves the purification of artificial graphite bodies containing metallic impurities by impreg nating the graphite with a chlorinated hydrocarbon at a high temperature to form and volatilize chlorides of the impurities. The process is particularly applicable to the purification of graphite anodes used in electrolytic cells. Monsanto patents included herein relate to binders for rocket propellants, a biphenyl-polyamide polymer, insecti cide, and light stabilizers. COMMENTS It is apparent from the results of this search effort that the subject matter regarding uses and applications of bi phenyls and chlorinated biphenyls is too broad to permit more than a thumbnail sketch of any particular area. There are no doubt pertinent references which have not been found because of limitations in the search effort imposed by the scope of the subject matter. This report will, however, provide an indication of the current state of the art in these several areas which can form a basis for a more concentrated effort if warranted by business or technical demands. Any further searching should be conducted within guidelines of well-defined objectives and limited subject matter. The results on biphenyl manufacture and chlorination which were the primary objectives of this survey are considered to be reasonably complete, as is the listing of pertinent Monsanto patents. The Patent Department will undertake to keep these results current, and to supplement the sections on use as additional references are uncovered during the course of time. / WRE:map Enclosures W. R. Eberhardt DSW 269204 STLCOPCB4054197 APPENDIX INDEX The survey covered both manufacture and use of chlorin ated biphenyls and polyphenyls according to the following: Subject Number of References Others Monsanto I. Manufacture of Biphenyl and Polyphenyls A. Pyrolysis of Benzene B. Other Routes C. Refining and Purification II. Chlorination of Biphenyl & Polyphenyls III. Functional Fluids A. Heat Transfer Reactors Others B. Dielectrics C. Hydraulics D. Lubes E. Thermodynamic Fluids F. Quenchant IV Adhesive Compositions A. Hot Melt B. Others V. Coatings VI. Plasticizers - Antiplasticizers A. PVC B. Resins C. Antiplasticizers VII. Solvents VIII. Flame Retardants IX. Miscellaneous Insecticides Preservatives Stabilizers 11 12 4 10 13 2 8 10 8 0 0 7 9 17 9 8 7 7 7 16 2 4 0 3 7 1 16 3 0 1 2 1 0 3 0 1 0 0 2 5 DSW 269205 STLCOPCB4054198 ABSTRACTS OF REFERENCES I. Manufacture of Biphenyl and Polyphenyls A. Pyrolysis of Benzene 3,359,340 Dow Chem. 3,262,983 Dow Chem. 2,099,350 Dow Chem. 1,978,069 Dow Chem. 1,976,468 Dow Chem. A process for the production of polyphenyls by the pyrolysis of benzene containing 0.1-5% phenol in the presence of Cu. The pyrolysis temperature is about 680C. and method yields 90% biphenyl and 9% terphenyl based on about 11% benzene conversion. A process for the production of diphenyls and terphenyls from the pyrolysis of benzene using certain nickel chromium steels to inhibit carbon formation. The steel specified contains 11-30% Cr, and a max. of 1.5% Ni. Benzene is pyrolyzed in apparatus of iron or carbon steel, the walls of which have been previously sub jected to the action of ammonia at a temperature of between 450 and 550C. for a time sufficient to form a nitrite coating thereon whereby the formation of carbon during the pyrolysis is substantially reduced. A process for producing diphenyl wherein benzene is pyrolyzed by heating at a temperature between 650 and 950C. The improvement which consists in main taining in the benzene a sulfur content in excess of about 0.10% by adding a substance from the class con sisting of sulfur and volatile sulfur compounds to the benzene before it enters the pyrolyzing zone. Polyphenyis are prepared by pyrolyzing a benzen* bi phenyl mixture containing from 5 to 20% biphenyl, separating the polyphenyls and recycling the biphenyl and unreacted benzene. The reaction takes place in the presence of a small amount of sulfur compound to minimize coking. Other operating conditions are, temperature 650 to 950C. with vapor velocity suf ficiently high to minimize coking. Conversion is between 5 and 20% of the benzene biphenyl vapors. A-2 DSW 269206 STLCOPCB4054199 1,322,983 Barrett Co. 3,228,994 Monsanto 2,702,307 Monsanto 3,227,525 Progil 3,207,799 Progil 3,112,349 Progil 1,968,154 Swann Re search 1,957,988 I.G.Farben Diphenyl is produced in a process wherein benzene is vaporized and mixed with-steam then reacted at a temperature of between 600 and 800C. and at a pressure of about 60 pounds per square inch. A process for the pyrolysis of benzene to biphenyl and polyphenyl in a tubular reactor constructed of a particular metallic alloy which retards the forma tion of coke. (Hastalloy X) A method for the pyrolysis of benzene in a tubular reactor wherein the flow rate corresponds to a Reynolds number of 600 to 100,000 and the tempera ture is maintained at 773K. to 1073K. This patent covers an apparatus designed to be used in the process of U. S. Patent 3,122,349 and claims a heat exchange tube having an internal diameter in the range of 55mm to 200mm and a length in the range of from about 30 meters to 100 meters and shaped of U bends joined by straight portions. A process for the production of terphenyls by the pyrolysis of benzene in the gaseous phase comprising the steps of heating a mixture of benzene containing 20 to 30% by weight of diphenyl at a temperature in the range of 680C. to 820C. for a period of from 10 to 500 seconds. The process being characterized in that the proportion of diphenyl in the gaseous mixture admitted to the pyrolysis zone is equal to proportion in the mixture leaving the zone so that there is no net consumption or production of diphenyl in the process. This patent covers a method of producing diphenyl by the pyrolysis of benzene vapor in a tube having the diameter in the range of 55mm to 205mm and causing the vapor to flow with a turbulence having a Reynolds number in the range of 120,000 to 500,000. Carbon formation during the pyrolysis of benzene to diphenyls is retarded by coating the walls of the re actor with a metal sulfide. Diphenyl is produced by passing vapors of benzene at about 750C. through a reaction space having a copper surface and containing a neutral reacting silicate selected from the group consisting of magnesium and aluminum silicates free from alkyl metal compounds. DSVJ*07 STLCOPCB4054200 B. Other Routes 3,435,084 Phillips Petroleum Biphenyls and other aromatic hydrocarbons are prepared from mixtures of Cs_g hydrocarbons by a process involv ing a series of fractionating, concentrating and hydrodealkylating steps. 3,401,207 Biphenyls are prepared from a liquid phase reaction of Gulf Research benzene with a palladium salt and acid catalyst. 3,274,277 A process for the preparation of biphenyl by liquid Universal Oil phase reaction of benzene and ethylene at 125-200C. and 800-1200 psi, in the presence of a strongly alka line catalyst on activated A^O^. 3,160,671 Atlantic A process for the production of high purity benzene by thermal dehydrodealkylation of toluene, wherein the formation of diphenyl in the benzene stream is pre vented by recycling diphenyls to the furnace. The amount of diphenyl recycled is described as that necessary to establish an equilibrium to prevent fur ther formation. A furnace is operated at 12,050 to 13,000 degrees F. and at 600 PSIG. 3,145,237 Shell Oil A process for the production of diphenyls by the catalytic coupling of benzene using a palladium or platinum salt catalyst under substantially anhydrous conditions and at a temperature of from about 40-200C. 3,055,956 Ashland Oil A process for recovering naphthalene from petroleum hydrocarbon fractions which comprises removing the alkylnaphthalenes by fractionation and hydrodealkylat ing the remainder to convert the alkylbenzenes into benzene and lower boiling alkylbenzenes. 2,951,886 Ashland Oil Benzene is obtained by subjecting coke oven or coal tar light oil to catalytic cracking in the presence of hydrogen at temperatures above 1200F. The catalyst is chromium oxide on a high purity, low sodium, gamma type alumina support. 2,918,503 American Oil A process for preparing a -terphenyl which comprises subjecting an alpha-methylstyrene to reaction in the liquid phase at a temperature from between about 150 and 700C. in the presence of an iodine compound catalyst. British 1,164,561 Hercules Biphenyl is obtained in 18% yield by reacting CO with a mixture of PhHgCl, CuCl2, and LiPdCl3 in acetonitrite at atmospheric pressure. DSW 269208 STLCOPCB4054201 British 1,159,653 Unassigned Benzene is converted to diphenyl in the presence of an iridium catalyst. Japan 6464 Yawata Chem. Dimers of methylstyrene are heated in the nitrogen atmosphere at 500C. in the presence of chromia-alumina catalyst to give p-terphenyl. French Chlorinated biphenyls and trichlorobenzenes are pre 1,522,859 pared by treating the *-hexachlorocyclohexane residue VEB Synthese- from the preparation of lindane with AlCl^. werk 3,244,721 Monsanto A process for arylation of aromatics by reacting a compound like biphenyl or naphthalene with benzene sulfonyl chloride in the presence of a catalyst such as a copper or silver salt. 3,231,629 Monsanto A process for arylation by reacting an aromatic like biphenyl or naphthalene with benzene sulfonyl chloride at 275C. This is a basic MCL patent. 3,328,473 Monsanto Aromatic compounds are arylated with an acylanilide and a nitrosating agent. Mixed terphenyls are made by reacting diphenyl with acetanilide and amyl nitrite at 85C. 3,197,520 Monsanto A process for the arylation of aromatic compounds such as the preparation of terphenyl by introducing a phenyl group onto diphenyl. C. Refining and Purification 3,363,020 Dow Chem. Czech. 124,741 Unassigned Czech. 123,386 Unassigned French 1,489,353 Euratom Biphenyl is refined and the yellow color removed by adding I^SO^ and distilling. The dielectric constant of chlorinated diphenyls im proved by heating the diphenyl with a mixture of CaO and perlite. Crude diphenyl is heated to isomerize the o-terphenyl the m- and p- isomers which are then separated from the diphenyl. Terphenyl is contacted with Zr metal at 300-400 to remove chlorinated impurities. A-5 OS****09 STLCOPCB4054202 II. Chlorination of Biphenyl & Polyphenyls 3,358,040 Texaco Chlorinated biphenyls and biphenyl ethers are prepared by treating substituted diphenyls with a cupric halide in the presence of an aluminum halide catalyst and an inert solvent. Products are 4,4'bis(p-chlorophenoxy)biphenyl and 4,4'-bis(p-chlorophenyl)biphenyl. 3,029,295 A process for the vapor phase chlorination of di d'Ugine Wyan phenyl in a fluid bed catalyst at a temperature of dotte 470-530C. (French 1,387,233) 2,859,252 Pennsalt A process for producing chlorinated polyphenyls com prising reacting benzene hexachloride with a nuclear halogenated aromatic hydrocarbon at a temperature of 130-225C. 2,854,491 A method for producing chlorinated aliphatic hydro Columbia- carbons by chlorinolysis of a cyclic compound having Southern Chem.at least 5 ring members with chlorine under pressure 2,812,370 Pennsalt A process for recovering the AICI3 catalyst used in the production of chlorinated polyphenyls by reaction of benzene hexachloride with a reactive aromatic. 2,608,591 Niagara Al kali French 1,448,922 Sandoz Ltd. A process of nuclear substitution chlorination which comprises dissolving an aromatic hydrocarbon in liquid chlorine in the presence of a chloride chlorination catalyst at about 80C. and under pressure. A process for the halogenation of aromatic hydrocarbons (biphenyl) using TiCl4 as a solvent. Polish 51,533 Glowny Inst. Diphenyl is chlorinated over spiral steel shavings to yield a non-flammable oil. E. Germany 62,553 Unassigned Addition to East German 58,739. The chlorination re action is conducted in perchloroethylene which is a solvent for the reactants but not the catalyst. E. Germany 58,739 Unassigned A process for the chlorination of hydrocarbons in the presence of AICI3 to produce chlorinated biphenyls, trichlorobenzene, and chloroarene polymers. A-6 DSW 269210 STLCOPCB4054203 2,551,562 Monsanto 3,256,350 Monsanto 3,256,343 Monsanto A new composition of matter of 50 to 80% of chloiinated meta-diphenylbenzene and 20 to 50% of chlor inated para-diphenylbenzene, the mixture containing 50 to 70% chlorine. The process of producing the composition by chlorinating meta-diphenylbenzene obtained as the high boiling fraction from the dis tillation of crude diphenyl material. Halogenated aromatics are produced by decomposing an aromatic sulfonyl halide in the presence of a high boiling solvent (AROCLOR). Halogenated aromatic compounds (AROCLOR) are produced by the vapor phase thermodecomposition of an aromatic sulfonyl halide. III. Functional Fluids A. Heat Transfer - Reactors 3,064,061 U.S. AEC Polymerized polyphenyl heat transfer fluids are re claimed by catalytic cracking to yield mixtures of biphenyl and terphenyl. 2,925,448 N.A.Aviation A nuclear reactor coolant comprising an aromatic hydrocarbon and 0.1 to 5% of an aluminum or tin ha lide . 2,915,567 U.S. AEC The resistance of polyphenyls to neutron radiation at elevated temperatures is improved by the incorpor ation of certain metal free aromatic inhibitors cap able of forming stable free radicals and selected from the group consisting of naphthacene, phthalocyanine, and triphenyl-methane. 2,909,488 U.S. AEC A nuclear reactor coolant consisting essentially of a liquid aromatic hydrocarbon and having dispersed therein beryllium or magnesium metal. 2,909,487 U.S. AEC A nuclear reactor coolant consisting essentially of a liquid aromatic hydrocarbon having dispersed therein an alkali metal. 2,909,486 U.S. AEC A nuclear reactor coolant consisting essentially of a liquid aromatic hydrocarbon and from 0.1 to 5% of a group IIA or IVA metal hydride. A-7 DSVJ 269211 STLCOPCB4054204 2,883,331 U.S. AEC The resistance of polyphenyls to neutron radiation at elevated temperatures is improved by the incor poration of certain arylselenium and sulfur com pounds at a level from about 1 to 10% by weight. Belgium 649,520 AEC-France A fluid comprised of a mixture of non-substituted terphenyls and short chain alkylaromatics. England(1964) Heat transfer in organic cooled reactors and the conChera.Eng.Progr.vective heat-transfer coefficients for unirradiated 60(51)128-36 and irradiated polyphenyl coolants are described. England(1964) Kieller Rept. KR 83, 12 pp. No.Amer.Avia. The irradiation facility which uses a eutectic mix ture of biphenyl, o-terphenyl, and p-terphenyl as a coolant is described. (1964) Euratom Bull. 7-13 A critical discussion of the advantages and disadvan tages of biphenyls and terphenyls as organic coolants for atomic reactors. (1964) Low melting organic coolants for reactors are terphenyl At.Energy,Can. biphenyl mixtures or partially hydrogenated terphenyl Ltd. AECL-1915 mixtures. At.Energy,Can. Ltd. Germany(1961) Kernenergie 4(9) ,669-84 Inst. Phys., Dresden,Ger. Diphenyls, terphenyls, and mixtures thereof are evalu ated as moderators and coolers in nuclear reactors. 3,280,206 Monsanto A process for reclaiming used polyphenyl nuclear re actor fluids by removing the undesirable high boilers with a two component solvent such as benzene plus ndodecane. 3,209,042 Monsanto A process for reclaiming used polyphenyl nuclear re actor fluids by hydrocracking the high boilers using hydrogen with a platinum or chromium catalyst. 3,184,390 Monsanto Biphenyl and nuclear reactor coolants are stabilized against radiolytic degradation by adding up to 50% of a mixture of bitumens selected from asphalt, coal, tar and petroleum residue. A-8 DSW 269212 STLCOPCB4054205 3,183,165 Monsanto 3,152,961 Monsanto 3,113,090 Monsanto 3,064,061 Monsanto Biphenyl and nuclear reactor coolants are stabilized against radiolytic degradation by adding about 30=6 of a partially hydrogenated terphenyl (HB-40). Rosin acids are added to terphenyls to provide a radiation-resistant reactor moderator or coolant. Biphenyl and nuclear reactor coolants are stabilized against radiolytic degradation by adding 5% anthra cene . A process for cracking polyphenyls, such as terphenyl, to biphenyl and benzene at 500-600C. using hydrogen and a platinum or nickel catalyst. Heat Transfer - Others 3,415,896 General Elec. Biphenyls having an -OR or a -NH2 group is reacted with a benzene or biphenyl having at least one cyclo hexyl substituent at a temperature of 300-500C. and in the presence of a nickel, platinum or palladium catalyst. The reaction permits the preparation of novel substituted biphenyls useful as high tempera ture heat transfer fluids. England(1967) AROCLOR is used as a direct-contact heat exchange Can.J.Chem.Eng.agent with the condensation of steam in a packed 45(3),170-4 column. Univ. of Brit. Columbia 3,249,152 Monsanto Heat is recovered from exhaust gases by spraying a chlorinated diphenyl into the gas, then transferring the heat from the diphenyl to water. B. Dielectrics 3,419,498 Westinghouse A cellulosic insulation material for use in trans formers in the presence of air and a liquid dielectric 3,362,908 A chlorinated diphenyl dielectric plus an epoxide com General Elec. pound as a scavenger material. 3,200,077 DePont A dielectric composition consisting of a mixture of a fluoroalkyl benzoate and a chlorinated aromatic hydrocarbon. A-9 DSW 269213 STLCOPCB4054206 3,194,766 Progil A dielectric comprising at least 20% of 2,4'dichlorodiphenyl and 40-70% of poly chlorodiphenyis having 3-4 chlorines. 3,170,986 AROCLOR plus an epoxide scavenger and a zeolite de General Elec. hydrating compound. 2,902,451 Sprague Elec. AROCLOR plus a low molecular weight liquid polymer of butadiene or an alkyl or aryl derivative thereof as a thermo stabilizer. 2,840,627 Westinghouse A dielectric comprising AROCLOR with an epoxy com pound and a basic nitrogenous compound as scavengers. 2,788,327 Sprague Elec. A dielectric consisting of a liquid chlorinated aromatic admixed with 10% tetra-2-ethy1-hexyl ortho silicate . 3,089,987 Monsanto A dielectric composition consisting of a mixture of chlorinated biphenyls and an alkyl chlorobiphenyl ether. 3,072,728 Monsanto A process for the preparation of bis(2-chlorophenyl) ether dielectrics by chlorinating 2-chloro-21-Nitro diphenyl ether. 3,068,297 Monsanto A process for the isomerization of 2,2'-dichlorobiphenyl to a dielectric mixture rich in the 2,4'- and 2,3*-isomers (Weingarten). 3,038,107 Monsanto A dielectric fluid prepared by halogenating 2,4'dichlorobiphenyl (Weingarten). 2,977,516 Monsanto Dielectric combinations of tri- and tetra-chlorobiphenyl isomers having unusually high dielectric con stants (Weingarten). 2,646,403 Monsanto Dielectric comprising AROCLOR plus diphenyl tridiethylate as a scavenger. 2,627,504 Monsanto Dielectric comprising AROCLOR plus mono-ortho-tolyl biguanide as a scavenger. 2,617,770 Monsanto Dielectric comprising AROCLOR plus a scavenger such as diaminodiphenylamine, o-anisidine, and nitro aniline. A-10 DSW 269214 STLCOPCB4054207 2,582,200 Monsanto 2,578,359 Monsanto 2,573,894 Monsanto 2,572,808 Monsanto 2,566,208 Monsanto 2,566,196 Monsanto 2,566,195 Monsanto 2,532,616 Monsanto Dielectric comprising AROCLOR plus ethyl silicate as a scavenger. Dielectric comprising AROCLOR plus dibutyl diphenyl tin as scavenger. . Dielectric comprising AROCLOR plus certain organotin compounds as scavengers, (triphenyl-thienyl tin and di-thienyl tin mentioned) AROCLOR as a dielectric and heat transfer fluid con taining N,N'-l-3-dimorpholino-isopropanol as a scavenger. Dielectric comprising AROCLOR plus organic antimony compounds as scavengers. Dielectric comprising AROCLOR plus aminated-Nphosphoryl-o-aminobiphenyl as a scavenger. Dielectric comprising AROCLOR plus aluminum isopropylate as a scavenger. A dielectric comprising an AROCLOR with a scavenger such as zinc dithiocarbamate and the alkyl, cyclic and aryl substituted derivatives thereof. C. Hydraulics 3,432,437 McDonnell- Douglas A fire resistant hydraulic fluid comprising a mixture of phosphate ester, chlorinated diphenyl ether, and a chlorinated biphenyl. 3,432,436 McDonnell- Douglas A fire resistant hydraulic fluid comprising a mixture of chlorinated diphenyl ethers and chlorinated bi phenyl. 3,352,784 McDonnell- Douglas A fire resistant hydraulic fluid comprising a mixture of phosphate esters with chlorinated diphenyl ether. 3,136,726 Douglas A fire-resistant hydraulic fluid and lubricant compris ing 20-80% triaryl phosphate, 80-20% chlorinated biphenj of 40-55% Cl, plus V.I. improver. A Commercial Enter prise Fluid. 3,282,847 Farben-Bayer A hydraulic fluid comprised of tricresyl phosphate and tetrachlorodiphenyl. A*U oS'N W92'5 STLCOPCB4054208 3,251,773 Dow Chem. m-dibromo-phenyl ether is added to silicone and mineral oils to impart flame resistance. 3,056,745 Farben-Bayer A hydraulic fluid consisting of a chlorinated di phenyl and a polyoxyalkylene diol in the ratio of from 10:1 to 100:1. 2,502,392 Hooker A hydraulic fluid comprised of hexachlorobutadiene and isopropyl trichlorobenzene containing a small amount of pentachlorodiphenyl and other halogenated materials to lower the freezing point. U.S.S.R.(1966) A hydraulic fiuid comprising a petroleum base, an 178,439 ethylpolysiloxane, and an additive package of chlor Unassigned inated biphenyls, biphenlyamine, and ionol. France (1966) 1,458,437 Progil, S.A. A hydraulic and lubricating fluid comprising a mix ture of diphenoxydiphenyls, diphenoxybenzene and terphenyl. 3,149,077 Monsanto Composition of Pydraul 200 comprising chlorinated biphenyl and a small amount of a metal salt of an organic thiophosphate, EP agent and a polyamine/ oleic acid reaction product as rush inhibitor. 2,741,598 Monsanto A heat transfer, hydraulic and thermoregulator medium consisting of 62% chlorinated biphenyl, 25% o-terphenyl and 13% biphenyl. 2,707,176 Monsanto A functional fluid comprised of 40-55 parts tricresyl phosphate, 45-60 parts chlorinated biphenyl of 40-60 parts chlorinated biphenyl of 40-60% Cl and a V.I. improver. D. Lubes 3,352,780 Labofina,Belg. An E.P. and hydrolysis resistant lubricant comprising a polychlorinated diphenyl containing 0.5-5% of a phosphoric ester. Also useful as hydraulic and heat transfer fluid. (Belg. 668,430) 3,297,574 Shell Oil Chlorinated biphenyl and a triaryl ester of phosphorothionic acid are added as EP agents to an aliphatic acid ester lubricating oil. 3,123,560 Richfield Oil A grease composition comprising chlorinated diphenyl synthetic oil of lubricating viscosity and 2 to 10% of a pyrogenic silica thickener. f A-12 SW 269276 STLCOPCB4054209 2,863,833 Unassigned A lubricant comprising sulfur, soapstone, graphite and about 5% chlorinated diphenyl. 2,852,468 Standard Oil A lubricating composition consisting of sulfurized mineral oil, a fatty acid ester, and AROCLOR 1254 as an EP agent. 2,630,417 DuPont A pressure coalescing composition comprising tetrafluoroethylene colloidal polymer admixed with a chlorinated aromatic of 15-65% chlorine. 2,593,507 Low molecular weight chlorinated diphenyls are used Thompson Prod, as lubricants in molding non-plastic, ceramic like powders. England(1965) Solid biphenyl is used as a lubricant in metal to Wear 8(5)358-73plastic friction. Inst.Petrochem Russia E. Thermodynamic Fluids 3,234,734 Monsanto Biphenyl and AROCLOR are disclosed as thermodynamic fluids for Rankin cycle engines. F. Quenchant 3,271,207 Monsanto AROCLOR is used as a quenchant for heat-treating glass or metal. 3,224,910 Monsanto The duplex steel quenching process using an upper water phase and a lower AROCLOR phase. IV. Adhesive Compositions A. Hot Melt 3,378,509 A thermosetting hot melt composition comprising a Chemical Decor-vinyl polymer binder and biphenyl solvent with sta- ation Co. bilizers and crosslinking agents. 3,220,966 Natl.Starch Chlorinated biphenyl resins are blended with ethylenepropylene copolymers and polyolefins to provide a tacky, hot-melt adhesive. A-13 DSW 269217 STLCOPCB4054210 2,685,572 B.B.Chemical A heat activatable cement for attaching shoe soles comprising 100 parts AN-butadiene copolymer, 10-30 parts zinc carbonate, 70-125 parts VA VC1 polymer and 10-50 parts of a chlorinated biphenyl resin having 65-67% chlorine. 2,643,238 Shawinigan Chlorinated diphenyl is used as plasticizer for a hot melt vinyl ester base adhesive resin. 2,633,432 A heat-sealable label stock having a multilayer McLaurin-Jones adhesive coating including one layer of a thermo- plastic material and an adjoining layer of a plasticizer for the material which are merged by heating into a single tacky layer. 2,622,056 An adhesive consisting of polyethylene resin and Union Carbide a halogenated benzene, diphenyl, or naphthalene. 2,612,463 DuPont A hot melt adhesive comprising a polyamide and a chlorinated diphenyl useful in bookbinding. 3,282,881 Monsanto Copolymers of ethylene/vinyl acetate are modified by the addition of a chlorinated terphenyl resin to produce a hot-melt adhesive composition. B. Others 2,988,461 National Cash Register An adhesive suitable for nicro-encapsulation com pressing a chlorinated rubber, polymerized rosin, hydroabietyl phthalate, chlorinated diphenyl and diethylbenzene. 2,954,353 A remoistenable adhesive mixture comprising poly- St.Regis Paper vinyl alcohol and lignosulfonic acid containing 5% of a migration inhibitor such as chlorinated di phenyl. 2,947,710 Johnson & Johnson Chlorinated biphenyl is incorporated as a tackifying agent in an elastomeric rubber base pressure sensi tive adhesive. 2,678,586 Eastman A thermosetting optical cement comprising a mixture of diallyl phenyl phosphonate and a chlorinated di phenyl . A-14 DSW 269218 STLCOPCB4054211 2,677,672 Swift & Co. An adhesive for wood comprising a mixture of PVA and a vinyl methyl ether-maleic anhydride copolymer. 2,633,593 Detro Mfg. A tackifier for a tack rag consisting of a solu tion of chlorinated triphenyl and polystyrene. French (1967) 1,482,172 Bericol S.A. A glue composition comprising polyamide, poly ester, or natural rubber and pentachlorobiphenyl. E.Germany(1965)Chlorinated biphenyl is added to the adhesive used 40,927 for poly(vinyl chloride) films. Unassigned E.Germany(1965)Chlorinated biphenyl is used as an ingredient in 37,967 an adhesive consisting of chlorinated polybutadiene Unassigned and rosin. V. Coatings 3,279,945 I.B.M. 2,938,937 Ideal Chem. Prod. 2,879,827 Taylor Fiber Company 2,840,486 Unassigned 2,828,213 Union Oil Chlorinated biphenyls are combined with resins to coat the ferrite core in a magnetic memory computer and thereby reduce magnetic vibrations. A flame-resistant, high-heat insulating composition comprising a filler of asbestos fiber and vermiculite, and a vehicle comprising a chlorinated rubber and a chlorinated hydrocarbon. An insulating material comprising a paper coated with cresol, phenol, formaldehyde-resin, tricresyl phosphate, and chlorinated diphenyl. A composition of matter comprising pigment, a wet ting agent, a solvent, and a chlorinated polyphenyl A putty composition which can be used under water. A rust preventing coating for ferrous metals com prising 85-97% chlorinated polyphenyl containing 50-70% chlorine, 0.5-7.5% petroleum sulfonate and 1.5-7.5% partial ester of a polyhydric alcohol. A-15 DSW 269219 STLCOPCB4054212 2,672,793 A sealer for concrete floors comprising a priming Bonafide Mills layer of a slow-drying penetrating solvent and a resinous material such as chlorinated rubber or chlorinated polyphenyl. 2,640,817 Nash-Kelvina- tor An anti-static coating material comprising polychloro biphenyls and an acrylate polymer, 2,635,970 Eastman Kodak A translucent paper impregnated with 25 parts cellulose acetate butyrate, 75 parts chlorinated di phenyl, and overcoated with a mixture of cellulose acetate butyrate, dibutyl sebacate, and butyl stearate. 2,635,085 An electrical insulating and moisture-proofing com- Soc. des Usinesprising 40-50% PVC, 25-35% soft pitch and 15-35% Chimique, plasticizer as chlorinated diphenyl. France 2,556,451 Insl-X A moisture resistant and fungus resistant hot melt coating composition comprising lanolin, a butyl methacrylate polymer, a high melting waxy acylamide, chlorinated diphenyl, a resin and a mercury com pound . 2,549,127 Stopall A waterproofing composition for wood comprising a chlorinated polyphenyl, a hydrogenated methyl abietate, polysiloxane and solvent. 2,536,657 Di-Noc Drawing material comprising a sheet of thermoplastic resinous material with a coating comprised of an acrylic resin, AROCLOR, and a fine abrasive. British(1966) 1,047,512 3M Halogenated polyphenyls are used as heat sensitive coating materials for thermographic papers. British(1966) 1,020,108 Formica Corp. Chlorinated biphenyl is used in a phenolic resin to impregnate and laminate paper into printed circuit boards. British (1965) Thermographic papers are impregnated with AROCLOR 986,053 as a heat volatilizable oil which is readily trans Kodak Ltd. ferred from one sheet to another. A-16 DSW 269220 STLCOPCB4054213 Netherlands A heat resistant coating for ironing boards com 109,025 (1964) prising a mixture of cellulose acetobutyrate, Unassigned chlorinated biphenyl, and aluminum metal particles. French (1964) 1,358,684 Kommandit- bolaget Chlorinated biphenyl is used as one ingredient of a white camouflage coating having U.V. radiation properties similar to snow. 2,926,096 Monsanto A composition consisting of chlorinated phenol and a phosphoric acid ester, for impregnating cellulosics to make them flame retardant and resistant to fungus and insects. 2,606,165 Monsanto A polishing composition comprising an aqueous emulsion of a vinyl copolymer, a wax and chlorin ated biphenyl. 2,500,426 Monsanto Meta-terphenyl with paraffin and yellow ceresin as a moistureproof coating for artificial flowers, fruit and the like. VI. Plasticizers - Antiplasticizers A. PVC 2,525,177 Calresin PVC or PVC-acetate molding resins are plasticized with chlorinated terphenyls. Russia (1967) Lakokrasoch, Mater. Ikh Primen. (1),10-14 A study of the effect of plasticizers such as chlor inated biphenyl on the degradation of coatings based on chlorinated poly(vinyl chloride) in the process of radiation aging and on drop in adhesion in this process. Tricresyl phosphate was found to be a more effective stabilizer. Russia (1967) Vysokomol. Soedin., Ser. A 9 (11) , 2370-5 Poly(vinyl chloride) containing 3% Ca stearate was plasticized with 36% of biphenyl or p-terphenyl. A-17 DSW 269221 STLCOPCB4054214 Russia (1967) Vysokomol. Soedin., Ser. A 9(9) , 1967-72 Biphenyl is used as a plasticizer in poly(vinyl chloride) dielectric film. Russia (1967) The dielectric and mechanical properties of poly- Izv. Vyssh. (vinyl chloride) films containing biphenyl as a Ucheb.Zaved.,stabilizer are discussed. Khim. Khim. Tekhnol. 10(2), 245-8 Russia (1966) Biphenyl and p-terphenyl are evaluated as plastiIzv. Vysshikh cizers for poly(vinyl chloride). Uchebn. Zavedenii, Khim. i Khim. Tekhnol. 9(2), 303-5 Eng. Construct. Institute Russia (1966) Chlorinated poly(vinyl chloride) coating material Lakokrasochnye is plasticized with chlorinated biphenyl to decrease Materialy glass transition temperature and increase adhesion i ikh Pri- properties. menenie (4), 46-9 Russia (1965) Vysokomolekul. Soedin 7(4), 751-5 Chlorinated biphenyl is shown to be an interbundle plasticizer for chlorinated poly(vinyl chloride) polymer. The biphenyl does not enter into the structural elements. Russia (1965) Biphenyl and pentachlorobiphenyl are evaluated as Kolloidn. Zh. plasticizers for poly(vinyl chloride). 27 (1) , 19-23 Inst.Bldg.&Eng. B. Resins 3,269,308 Unassigned Chlorinated biphenyls are used as plasticizers for various resins used in flexographic printing plates. 3,200,056 3M An electrically non-conductive stabilized polyethylene containing as stabilizers an organic chlorinated ma terial, antimony trioxide, an amine-antioxidant, and carbon black. A-18 0S\N 269222 STLCOPCB4054215 3,182,036 AROCLORS are added to poly(b-hydroxybutric acid) W.R'.Grace Co. as a plasticizer. 2,968,639 Eastman AROCLORS are used as plasticizers for high molecular weight, high melting linear polyesters in the mold ing operation. ' 2,580,023 Goodcliff, Ltd. Chlorinated diphenyls are used as softeners in a coating composition for steel comprised of chlorin ated rubber and a heavy metal powder. 2,529,260 Armstrong Several varieties of resins and rubber compositions suitable for use as floor tiles are plasticized with diphenyl or chlorinated diphenyl. England (1965) Vinyl polymer based paints plasticized with chlorin J. Oil Colour ated biphenyls are used in atomic energy installa Chemists' tions and are tolerant to high energy radiation. Assoc. 48(1), 28-37 At. Energy Res. Estab. French (1965) 1,402,991 S. Civile Fiorillo Chlorinated biphenyls or polyphenyls are used as plasticizers in a putty consisting of a vegetable drying oil and a copolymer of ethylene with vinyl acetate or styrene. 2,506,014 Monsanto Still residues from the preparation of chlorinated diphenyls and diphenyl benzenes are incorporated in polyvinyl acetal compositions for recording disks. C. Antiplasticizers 3,254,047 Eastman Kodak Chlorinated biphenyls are added to polycarbonate film to increase the film stiffness. 3,240,735 Eastman Kodak Chlorinated biphenyls are added to polyester thermo plastic films to improve the stiffness of the film. England (1967) J.Appl.Polym. Sci. 11(2),227-44 Tenn.Eastman AROCLOR is used as an antiplasticization additive for polyester polymers. The additives appreciably in crease the modulus and tensile strength and decrease the elongation and heat distortion temperatures of the polymers. A"19 DSW 269223 STLCOPCB4054216 England (1967) J.Appl. Polym. Sci. 11(2), 211-26 Tenn. Eastman AROCLORS are used as antiplasticizers phenol polycarbonates. for bis England (1966) Bisphenol polycarbonate is antiplasticized with Amer.Chem.Soc. 20% AROCLOR 5460 to yield a clear, hard, stiff, Div.Org.Coat- tough, self-extinguishing molding plastic, ings Plastics Chem. Preprints 26(2), 170-9 Eastman Kodak England (1965) Chlorinated biphenyls and terphenyls are used as Advan.Chem.Ser.antiplasticizers for bisphenol polycarbonates, to No. 48, 185-95 increase tensile modulus and tensile strength of Tenn. Eastman films and decrease the elongation. England (1965) J.Polymer Sci. Pt. A 3(6) 2189-203 Eastman Kodak High molecular weight 2,2-bis (4-hydroxyphenyl) propane polycarbonate is plasticized with chlorobiphenyl (AROCLOR 1254) as control for PEG plas ticizer evaluation. VII. Solvents 2,934,575 DuPont A process of polymerizing acetylene to monovinylacetylene by introducing acetylene into an anhydrous mixture composed of two immiscible liquid phases, one of which is an inert liquid hydrocarbon or chlor inated hydrocarbon phase and the other is a solution of cuprous chloride and an aliphatic amine hydrochlor ide in a carboxylic acid amine solvent. 2,593,428 Standard Oil A process for the preparation of an organic ester from an organic carboxylic acid and a branched saturated aliphatic monohydric unsubstituted alcohol wherein the esterification is conducted in the presence of a minor proportion of diphenyl propane. 2,550,473 Natl. Cash Register Chlorinated diphenyl is used as a carrier for dye in a pressure sensitive record material. A-20 DSW 269224 STLCOPCB4054217 2,548,366 Natl. Cash Register Chlorinated diphenyl is used as inert liquid carrier for the color reactant in a sensitized record material sheet. Russia 170,661 Unassigned Polyarylates are prepared by the condensation of dicarboxylic acid chlorides with dihydric phenols in solutions of chlorinated biphenyl. England (1965) Chlorinated biphenyl is used as an epoxy cement Plastics Design stripper for removing cured epoxy adhesives from Process anodized aluminum parts. 18-21 England (1966) J.Soc.Dyers Colour. 82(11),405-9 Monsanto Co. Biphenyl is used as a dye carrier in the dyeing of polyester fiber with disperse dyes. VIII. Flame Retardants 3,418,267 DuPont A flame-resistant polyamide resin comprising 5-20% of a chlorinated biphenyl and 3-15% of a metallic oxide. 3,321,416 Badische Anilin AROCLOR is added to polystryene plastics to provide 2-7% chlorine for flame retardency. 3,154,515 General Elec. Chlorinated polyphenyls are added to organopolysiloxanes to provide a flame-retardant silicone rubber formulation. 3,014,000 Assoc. Lead Mfg. Ltd. A flame-retardant finish for textiles comprising antimony trioxide, a halogenated vinyl polymer, and a plasticizer containing chlorinated diphenyl or chlorinated paraffin. 2,881,097 Harshaw Chem. Chlorinated diphenyl is incorporated as a flameretardant in mildewcide compositions containing copper antimonate. 2,590,211 Chlorinated diphenyls are incorporated with thermo- Diamond Alkali plastic polymers to impart flame resistance. A-21 DSW 269225 STLCOPCB4054218 French Mixtures of chlorinated hydrocarbons and a phos- 1,388,667 phonic acid ester are used as fireproofing agents Stauffer Chem. for polyurethanes. 3,352,744 Monsanto A flame-resistant phenolic resin composition com prising 5-60% of a chlorinated polyphenyl and 3-40% of a phosphate compound. 3,342,614 Monsanto AROCLOR is used as a flame-retardant for asphalt based roofing and wire coating compositions. IX. Miscellaneous 3,467,536 Farben-Bayer Chlorinated terphenyls are added to lacquers as light stabilizers. 3,394,095 M.Arguesco Co. A resin composition comprising a natural wax, a high molecular weight ethylene vinyl acetate copolymer, a hydrogenated glyceride, and a chlorinated diphenyl. The resin is hard and has a high coefficient of friction. 3,378,509 A pigment paste suitable for coloring a vinyl base Chemical Decor-hot melt adhesive comprising epoxidized soybean oil. ator Co. AROCLOR 1254, TiO2r and pigment. 3,282,902 AROCLOR is mixed with liquid polysulfide polymer and Thiokol Chem. other additives to produce a cureable polysulfide. 3,277,046 Johnson & Johnson Chlorinated biphenyls and terphenyls are added to poly-a-olefins containing U.V. stabilizers to fur ther increase the stability. 3,254,562 Polaroid Hydroxypolyphenyls are U.V. polarizers and are used to treat a film of poly(vinyl alcohol) . 3,035,901 Great Lakes Carbon Artificial graphite bodies containing metallic car bide impurities are purified by heating the graphite in a chlorinated hydrocarbon at a temperature suf ficiently high to impregnate the graphite with the hydrocarbon and form and volatilize chlorides of the impurities. 2,966,440 Shell Oil An insecticidal composition comprising an insecticide and a resin such as chlorinated polyphenyl resin A-2 2 DSW 269226 STLCOPCB4054219 2,921,911 Pennsalt Finely divided strong oxidizing agents such as calcium hypochlorite are made substantially dustless by treating with chlorinated biphenyls having a flash point in excess of 180C. 2,809,147 (Public) U.S.Govt. An insecticidal composition comprising a chlor inated hydrocarbon insecticide and a film-forming chlorinated terphenyl. 2,746,872 Crown Zeller- bach Citrus fruits are packaged in a paper treated with diphenyl present in an amount sufficient to control decay, said paper being also treated with a citrus oil of the group consisting of lemon oil and bermagot oil and mixtures thereof. 2,713,006 Hunter Metal- lies A paste pigment composition of finely divided ferrous metal particles wetted and coalesced with a liquid chlorinated polyphenyl. England(1967) Measurements of dynamic shear impedance of chlorin- J.Chein.Phys. ated biphenyls and polystyrene-chlorinated biphenyls 47(11) ,4329-34 solutions were made by an ultrasonic reflectance Bell Telephone technique. The results are analyzed in terms of Labs viscoelastic behavior. England(1967) Plant Dis.Rep. 51(1), 58-61 Volcani Inst. Agr. Res. Paper impregnated with biphenyl is placed between lavers of fruit to control citrus fruit rot. " England(1966) Diphenyl is added to citrus fruits stored in poly Citrus Ina. ethylene bags to prevent citrus rot. 47(10), 9-11 Univ. of Florida England(1966) J.Phys.Chem. 70(7),2271-6 Univ. Kyoto, Japan Normal and shear stresses of solutions of polystyrene and chlorinated biphenyl solvent were measured. 3,209,046 Monsanto A process for the alkylation of an aromatic compound by heating the aromatic (diphenyl) with an aliphatic sulfonyl halide or an aliphatic sulfonyl acid. A-2 3 dSNN 269227 STLCOPCB4054220 3,014,796 Monsanto 2,894,923 Monsanto 2,857,258 Monsanto 2,588,318 Monsanto A solid rocket propellant containing a binder of ethyl cellulose plasticized with a chlorinated polyphenyl. Terphenyl is added as a light stabilizer to halo gen containing epoxy resin compositions. A rocket propellant comprising a particular non plastic gas generating composition and a binder comprising a resinous chlorinated diphenyl or terphenyl. A water emulsifiable soil poison concentrate com prising 25-45% chlorinated biphenyl, 25-45% tri chlorobenzene, 7-13% pentachlorophenol plus an alcohol, oil and wetting agent. WRE:rk A-24 0S\N 269223 STLCOPCB4054221