US2775563A - Resinous condensation products from metal alloys and hydrocarbon dihalides - Google Patents

Resinous condensation products from metal alloys and hydrocarbon dihalides Download PDF

Info

Publication number
US2775563A
US2775563A US294710A US29471052A US2775563A US 2775563 A US2775563 A US 2775563A US 294710 A US294710 A US 294710A US 29471052 A US29471052 A US 29471052A US 2775563 A US2775563 A US 2775563A
Authority
US
United States
Prior art keywords
hydrocarbon
dihalides
metal
alloy
condensation products
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US294710A
Inventor
Sol B Wiczer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to US294710A priority Critical patent/US2775563A/en
Application granted granted Critical
Publication of US2775563A publication Critical patent/US2775563A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule

Definitions

  • the resinous materials hereof are reaction products of where R is monocyclic or 1 to 4 carbon atom aliphatic hydrocarbon, X is halogen, Me is a polyvalent heavy metal forming true alloys with alkali metal and n is the number of valences thereof.
  • the product (a) theoretically illustrates a type of polymer where divalent heavy metal is reacted.
  • Such metals as copper, cadmium, zinc form such resins as shown theoretically in formula (a).
  • the hydrocarbon base is a hydrocarbon base of a character which does not tend to cyclize such as aliphatic of 1 to 4 carbon atoms or monocyclic aromatic or hydroaromatic and combined cyclic and acyclic types. These hydrocarbon bases are substituted with at least two halogen atoms, but any larger number may be used. The use of a larger number of halogen substituents on the hydrocarbon could theoretically form polymers with metal having a corresponding degree of cross-linking. With decrease in the atomic weight of the hydrocarbon base, the ratio of metal to the remainder of the molecule increases with consequent increase in specific gravity.
  • low molecular weight alkylene polyhalide base For purposes of forming polymers of high specific gravity, low molecular weight alkylene polyhalide base is preferred.
  • methylene dichloride, methylene dibromide, chloroform, bromoform, or carbon tetrachlon'de are suitable alkylene polyhalide base molecules.
  • ethylene polyhalides such as 1-2 dichloroethane, 1-3 dichloropropane, 1-4 dichlorobutane textra or hexachloro ethane or unsymmetrical trichloro ethane may be used.
  • polyhalogen monocyclic aromatics and alicyclics including hydrocarbon cyclic bases also having powder.
  • the reaction may also be eflfected upon polymerizable halogenated unsaturated materials such as polyvinyl chlo ride, chlorinatedrubber, dichlorobutadiene, 14, and polyhalogen vinyl acetylene and 1,2 dichloroethylene.
  • polymerizable halogenated unsaturated materials such as polyvinyl chlo ride, chlorinatedrubber, dichlorobutadiene, 14, and polyhalogen vinyl acetylene and 1,2 dichloroethylene.
  • the heavy polyvalent metal to be reacted is first alloyed with analkali metal such as sodium, potassium or lithium' by adding small pieces of the metal to a sodium, lithium, etc. melt.
  • analkali metal such as sodium, potassium or lithium'
  • Such polyvalent metals as mentioned above are alloyed with the melted sodium, lithium, etc. and the alloy is cooled and broken into small chips, granules or displaced from the hydrocarbon, but the sodium or lithium is preferably present in quantity to form an 8 to 50% alkali metal such as sodium content of the alloy with the polyvalent metal, preferably about 10 to 15%.
  • the halogenated hydrocarbon is directly reacted with the polyvalent metal sodium with heat and usually under" pressure for one to fifteen hours in an autoclave of 3 to 10 atmospheres, the temperature ranging from to 150 C. with or Without an inert solvent such as petroleum ether, hexane, or ligro'm. Where the halogenatedhydro carbon is of low volatility, the reaction may be carried out under reflux of the solvent in an inert atmosphere, such as nitrogen or hydrogen.
  • the reaction may be activated by certain catalysts such as organic or inorganic iodine and iodine compounds, organic acid anhydrides, certain metal alloys such as aluminum containing minor quantities of copper, zinc and iron, inorganic acid such as hydrochloric acid and art-- hydrous acid salts such as aluminum chloride and borontrifluoride.
  • catalysts such as organic or inorganic iodine and iodine compounds, organic acid anhydrides, certain metal alloys such as aluminum containing minor quantities of copper, zinc and iron, inorganic acid such as hydrochloric acid and art-- hydrous acid salts such as aluminum chloride and borontrifluoride.
  • the alloy melt is cooled and granulated. 87 grams of methylene dichloride is dissolved in 500 cc. of n-hexane to which is added 2700 grams of the granulated alloy of lead containing 10% of sodium and 2 grams of elemental iodine. The mixture is placed in an autoclave and heated at 73 to 75 C. for ten hours. At the end of the period the cooled liquid is filtered through active charcoal and the solvent removed by vacuum distillation. The product is a dark amber colored resin having a specific gravity of 6.7. The product is soluble in hydrocarbon naphtha and oils.
  • Example 11 A 10% alloy of metallic tin with sodium is prepared as described in Example I. grams of ethylene dichloride 1,2 is dissolved in 700 cc. n-hexane to which is added 1400 grams of the powdered alloy and the mixture is heated under air free reflux for fifteen hours. The solution and suspended salt are then filtered through decolorizing charcoal, and the solvent is removed under vacuum. The heavy brittle residue obtained has a specific gravity of 5.8, has an amber color and melts on the steam bath to a clean amber colored fluid.
  • Example 111 147 grams of paradichlorobenzene dissolved in 300 cc. of benzene and refluxed ten hours in an air free atmosphere with 35 grams of copper sodium alloy containing 10% of sodium prepared according to the method described in Example I. A brittle yellowish amber resin is obtained after purification and removal of solvent which has a specific gravity of 5.7.
  • the resins herein because of their solubility in solvent, particularly hydrocarbon and high specific gravity, are useful additives, weighting agents and filler materials.
  • They may be used as oil Well drilling fluid Weighting agents for oil type drilling fluids, as radio-paques, as rubber fillers, as blending agents for other resins, as molding powders alone and With other resins and filler materials.
  • a resinous material formed by reacting by heating a mixture of an alloy of an alkali metal and a heavy metal selected from the group consisting of copper, cadmium, zinc, lead, tin, thallium, gallium, indium, zirconium, tantalum, tungsten, molybdenum, uranium, iron, bismuth, cobalt, chromium, nickel, with a polyhalogen hydrocarbon compound selected from the group. consisting of monocarbocyclic dihalides and dihalides of aliphatic hydrocarbons having 1 to 4 carbon atoms, said heavy metal and dihalogen hydrocarbon compound being in substantially equal molar proportions.
  • the method of forming a heavy metal containing resin comprising reacting by heating a mixture of an alloy of an alkali metal and a heavy metal selected from the group consisting of copper, cadmium, zinc, lead, tin, thallium, gallium, indium, zirconium, tantalum, tungsten, molybdenum, uranium, iron, bismuth, cobalt, chromium, nickel, with a polyhalogen hydrocarbon compound selected from the group consisting of monocarbocyclic dihalides and dihalides of aliphatic hydrocarbons having 1 to 4 carbon atoms, said heavy metal and dihalogen hydrocarbon compound being in substantially equal molar proportions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Description

RESINOUS c'oNnENsATioN PRohUcrs FROM gTfiAIiESALLOYS AND HYDROCARBON DI- Sol B. Wiczer, Washington, .D. (I.
No Drawing. Application June 20,1952, Serial No. 294,710
7 Claims. (Cl. 260'-2)' The present invention is a continuation-in-part ofmy copending application Serial No. 69,617, filed January 6, 1949, now abandoned, and an improvement upon my Patent No. 2,447,926, and'relates to'heavyresinous' niaterials containing heavy polyvalent'metalbonded' to'hy drocarbon, and tea method of forming the same.
The resinous materials hereof are reaction products of where R is monocyclic or 1 to 4 carbon atom aliphatic hydrocarbon, X is halogen, Me is a polyvalent heavy metal forming true alloys with alkali metal and n is the number of valences thereof. The product (a) theoretically illustrates a type of polymer where divalent heavy metal is reacted. Such metals as copper, cadmium, zinc form such resins as shown theoretically in formula (a). Other higher valent heavy metals such as lead, tin, thallium, gallium, indium, zirconium, tantalum, tungsten, molybdenum, uranium, iron, bismuth, cobalt, chromium and nickel, may form cross linking polymers theoretically illustrated by such as product (b) and metals With more than one valence above such as cobalt, nickel, etc., may form mixed polymeric types.
The hydrocarbon base is a hydrocarbon base of a character which does not tend to cyclize such as aliphatic of 1 to 4 carbon atoms or monocyclic aromatic or hydroaromatic and combined cyclic and acyclic types. These hydrocarbon bases are substituted with at least two halogen atoms, but any larger number may be used. The use of a larger number of halogen substituents on the hydrocarbon could theoretically form polymers with metal having a corresponding degree of cross-linking. With decrease in the atomic weight of the hydrocarbon base, the ratio of metal to the remainder of the molecule increases with consequent increase in specific gravity.
For purposes of forming polymers of high specific gravity, low molecular weight alkylene polyhalide base is preferred. For such use, methylene dichloride, methylene dibromide, chloroform, bromoform, or carbon tetrachlon'de are suitable alkylene polyhalide base molecules. Similarly ethylene polyhalides such as 1-2 dichloroethane, 1-3 dichloropropane, 1-4 dichlorobutane textra or hexachloro ethane or unsymmetrical trichloro ethane may be used. Similarly polyhalogen monocyclic aromatics and alicyclics including hydrocarbon cyclic bases also having powder.
2 lower alkyl 'substituents wherein the halogen is substituted on the ring or in the side chain or both such as dichlorobenzene, hexachlorocyclohexane, polyhalogenated Xylenes, and parachlorobenzyl chloride.
The reaction may also be eflfected upon polymerizable halogenated unsaturated materials such as polyvinyl chlo ride, chlorinatedrubber, dichlorobutadiene, 14, and polyhalogen vinyl acetylene and 1,2 dichloroethylene.
The heavy polyvalent metal to be reacted is first alloyed with analkali metal such as sodium, potassium or lithium' by adding small pieces of the metal to a sodium, lithium, etc. melt. Such polyvalent metals as mentioned above are alloyed with the melted sodium, lithium, etc. and the alloy is cooled and broken into small chips, granules or displaced from the hydrocarbon, but the sodium or lithium is preferably present in quantity to form an 8 to 50% alkali metal such as sodium content of the alloy with the polyvalent metal, preferably about 10 to 15%.
The halogenated hydrocarbon is directly reacted with the polyvalent metal sodium with heat and usually under" pressure for one to fifteen hours in an autoclave of 3 to 10 atmospheres, the temperature ranging from to 150 C. with or Without an inert solvent such as petroleum ether, hexane, or ligro'm. Where the halogenatedhydro carbon is of low volatility, the reaction may be carried out under reflux of the solvent in an inert atmosphere, such as nitrogen or hydrogen.
The reaction may be activated by certain catalysts such as organic or inorganic iodine and iodine compounds, organic acid anhydrides, certain metal alloys such as aluminum containing minor quantities of copper, zinc and iron, inorganic acid such as hydrochloric acid and art-- hydrous acid salts such as aluminum chloride and borontrifluoride.
to molten sodium in proportion to form an alloy containing 10% by weight of sodium. The alloy melt is cooled and granulated. 87 grams of methylene dichloride is dissolved in 500 cc. of n-hexane to which is added 2700 grams of the granulated alloy of lead containing 10% of sodium and 2 grams of elemental iodine. The mixture is placed in an autoclave and heated at 73 to 75 C. for ten hours. At the end of the period the cooled liquid is filtered through active charcoal and the solvent removed by vacuum distillation. The product is a dark amber colored resin having a specific gravity of 6.7. The product is soluble in hydrocarbon naphtha and oils.
Example 11 A 10% alloy of metallic tin with sodium is prepared as described in Example I. grams of ethylene dichloride 1,2 is dissolved in 700 cc. n-hexane to which is added 1400 grams of the powdered alloy and the mixture is heated under air free reflux for fifteen hours. The solution and suspended salt are then filtered through decolorizing charcoal, and the solvent is removed under vacuum. The heavy brittle residue obtained has a specific gravity of 5.8, has an amber color and melts on the steam bath to a clean amber colored fluid.
Example 111 147 grams of paradichlorobenzene dissolved in 300 cc. of benzene and refluxed ten hours in an air free atmosphere with 35 grams of copper sodium alloy containing 10% of sodium prepared according to the method described in Example I. A brittle yellowish amber resin is obtained after purification and removal of solvent which has a specific gravity of 5.7.
Patented Dec. 25, 1956 v In such'alloy the polyvalent metal is present in greater than equivalent quantity to the halogen to be Example IV 80 grams of a sodium alloy with zinc are heated with 164 gr. of ethylene dibrornide 1,2 in 500 cc. of nhexane in an autoclave at 90 C. for 30 hours. A brittle amber colored resin having a specific gravity of 5.2 is obtained after filtering the reaction product and removing the solvent by distillation.
The resins herein, because of their solubility in solvent, particularly hydrocarbon and high specific gravity, are useful additives, weighting agents and filler materials.
They may be used as oil Well drilling fluid Weighting agents for oil type drilling fluids, as radio-paques, as rubber fillers, as blending agents for other resins, as molding powders alone and With other resins and filler materials.
I claim:
1. A resinous material formed by reacting by heating a mixture of an alloy of an alkali metal and a heavy metal selected from the group consisting of copper, cadmium, zinc, lead, tin, thallium, gallium, indium, zirconium, tantalum, tungsten, molybdenum, uranium, iron, bismuth, cobalt, chromium, nickel, with a polyhalogen hydrocarbon compound selected from the group. consisting of monocarbocyclic dihalides and dihalides of aliphatic hydrocarbons having 1 to 4 carbon atoms, said heavy metal and dihalogen hydrocarbon compound being in substantially equal molar proportions.
2. The method of forming a heavy metal containing resin, comprising reacting by heating a mixture of an alloy of an alkali metal and a heavy metal selected from the group consisting of copper, cadmium, zinc, lead, tin, thallium, gallium, indium, zirconium, tantalum, tungsten, molybdenum, uranium, iron, bismuth, cobalt, chromium, nickel, with a polyhalogen hydrocarbon compound selected from the group consisting of monocarbocyclic dihalides and dihalides of aliphatic hydrocarbons having 1 to 4 carbon atoms, said heavy metal and dihalogen hydrocarbon compound being in substantially equal molar proportions.
3. The resin defined in claim 1 wherein the metal is lead.
4. The resin defined in claim 1 wherein the metal is' copper.
5. The resin defined in claim 1 wherein the metal is tin.
6. The resin defined in claim 1 wherein the multivalent hydrocarbon radical is divalentcarbocyclic.
7. The resin defined in claim 1 wherein the hydrocarbon radical is a divalent aliphatic radical having 1 to 4 carbon atoms.
References Cited in the file of this patent UNITED STATES PATENTS 1,974,167 Voorhees Sept. 18, 1934 2,236,910 Lincoln et al. Apr. 1, 1941 2,383,817 Rochow Aug. 28, 1945 FOREIGN PATENTS 1,008,405 France Feb. 20, 1952 OTHER REFERENCES Gilman et al.: Iour. Org. Chem., vol. 10, No. 6, pages 505515, November 1945.
Hilpert et al.: Ber. Dent. Chem. Gesel., vol. 47, pages 177, to 182, 186 to 196 (1914).
Braun: Ber. Dent. Chem. Gesel., vol. 46, page 1792 (1913).
Goddard: Text-book of Inorganic Chem., vol. XI, part 1, pages 208-9 (1928), pub. by Charles Griffin & Co., London. I I
Whitmore: Organic Compounds of Mercury, pp. 349 to; 351 (1921), pub. by Chem. Catalog Co., New York.
Gruttner et al.: Ber. Dent. Chem. Gesel, vol. 49, 1916, pp. 2666, 2670, and 2671.
Vecchiotti et al.: Gazzetta Chemico Italiana, vol. 63, .1933, p. 110, 111.
Krause: V. Grosse Chemie der metall-organischen Verbindungen, Edwards Bros., 1943, pages 364, 365 and 366,

Claims (1)

1. A RESINOUS MATERIAL FORMED BY REACTING BY HEATING A MIXTURE OF AN ALLOY OF AN ALKALI METAL AND A HEAVY METAL SELECTED FROM THE GROUP CONSISTING OF COPPER, CADMINUM, ZINC, LEAD, TIN, THALLIUM, GALLIUM, INDIUM, ZIRCONIUM, TANTALUM, TUNGSTEN, MOLYBDENUM, URANIUM, IRON, BISMUTH, COBALT, CHROMIUM, NICKEL, WITH A POLYHALOGEN HYDROCARBON COMPOUND SELECTED FROM THE GROUP CONSISTING OF MONOCARBOCYCLIC DIHALIDES AND DIHALIDES OF ALIPHATIC HYDROCARBONS HAVING 1 TO 4 CARBON ATOMS, SAID HEAVY METAL AND DIHALOGEN HYDROCARBON COMPOUND BEING IN SUBSTANTIALLY EQUAL MOLAR PROPORTIONS.
US294710A 1952-06-20 1952-06-20 Resinous condensation products from metal alloys and hydrocarbon dihalides Expired - Lifetime US2775563A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US294710A US2775563A (en) 1952-06-20 1952-06-20 Resinous condensation products from metal alloys and hydrocarbon dihalides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US294710A US2775563A (en) 1952-06-20 1952-06-20 Resinous condensation products from metal alloys and hydrocarbon dihalides

Publications (1)

Publication Number Publication Date
US2775563A true US2775563A (en) 1956-12-25

Family

ID=23134593

Family Applications (1)

Application Number Title Priority Date Filing Date
US294710A Expired - Lifetime US2775563A (en) 1952-06-20 1952-06-20 Resinous condensation products from metal alloys and hydrocarbon dihalides

Country Status (1)

Country Link
US (1) US2775563A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2892782A (en) * 1955-08-29 1959-06-30 Texaco Inc Mixtures of metal salts of organic hydroxy compounds
US2998440A (en) * 1956-12-31 1961-08-29 Ethyl Corp Polymeric compositions
US3052658A (en) * 1957-06-03 1962-09-04 Hughes Aircraft Co Unsaturated chloromolybdate esters and polymers
US3062856A (en) * 1958-09-26 1962-11-06 Alclio Gaetano F D Metal-containing polymers and preparation thereof
US3128254A (en) * 1958-06-25 1964-04-07 Dal Mon Research Co Polymeric boron compositions
US3159589A (en) * 1959-10-21 1964-12-01 Artrite Resins Ltd Method for the preparation of polyaromatic resins
US3190901A (en) * 1961-06-08 1965-06-22 Basf Ag Linear polymers of alkylene tin chlorides
US3306878A (en) * 1962-12-15 1967-02-28 Distillers Co Yeast Ltd Trioxane polymerization process
US3350436A (en) * 1963-05-15 1967-10-31 M & T Chemicals Inc Organobismuth ethylenic carboxylates and polymers thereof
WO2004094504A1 (en) * 2003-04-22 2004-11-04 The University Of Reading Polymer networks

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1974167A (en) * 1932-09-01 1934-09-18 Standard Oil Co Antiknock gasoline
US2236910A (en) * 1938-07-11 1941-04-01 Continental Oil Co Synthetic lubricant
US2383817A (en) * 1940-04-30 1945-08-28 Gen Electric Organosilicon compounds
FR1008405A (en) * 1949-02-23 1952-05-19 Dow Corning Organosilane polymers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1974167A (en) * 1932-09-01 1934-09-18 Standard Oil Co Antiknock gasoline
US2236910A (en) * 1938-07-11 1941-04-01 Continental Oil Co Synthetic lubricant
US2383817A (en) * 1940-04-30 1945-08-28 Gen Electric Organosilicon compounds
FR1008405A (en) * 1949-02-23 1952-05-19 Dow Corning Organosilane polymers

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2892782A (en) * 1955-08-29 1959-06-30 Texaco Inc Mixtures of metal salts of organic hydroxy compounds
US2998440A (en) * 1956-12-31 1961-08-29 Ethyl Corp Polymeric compositions
US3052658A (en) * 1957-06-03 1962-09-04 Hughes Aircraft Co Unsaturated chloromolybdate esters and polymers
US3128254A (en) * 1958-06-25 1964-04-07 Dal Mon Research Co Polymeric boron compositions
US3062856A (en) * 1958-09-26 1962-11-06 Alclio Gaetano F D Metal-containing polymers and preparation thereof
US3159589A (en) * 1959-10-21 1964-12-01 Artrite Resins Ltd Method for the preparation of polyaromatic resins
US3190901A (en) * 1961-06-08 1965-06-22 Basf Ag Linear polymers of alkylene tin chlorides
US3306878A (en) * 1962-12-15 1967-02-28 Distillers Co Yeast Ltd Trioxane polymerization process
US3350436A (en) * 1963-05-15 1967-10-31 M & T Chemicals Inc Organobismuth ethylenic carboxylates and polymers thereof
WO2004094504A1 (en) * 2003-04-22 2004-11-04 The University Of Reading Polymer networks
US20060235166A1 (en) * 2003-04-22 2006-10-19 Tsang Shik C E Polymer networks

Similar Documents

Publication Publication Date Title
US2775563A (en) Resinous condensation products from metal alloys and hydrocarbon dihalides
Keller Coördination Compounds of Olefins with Metallic Salts.
Jacobson Polymers from benzyl chloride and related compounds
US3057926A (en) Sulfur-containing phenolic compounds
NO136923B (en) PROCEDURE AND APPLIANCE FOR MANUFACTURE OF A LAMINATED GLASS OBJECT.
US2718511A (en) Solution of polymeric chlorotrifluoroethylene
JPH01501006A (en) Composition for capsules
US3440263A (en) Method of preparing modified silicone polymers
US3812220A (en) Phosphate esters of hindered phenols
US2964548A (en) Process for the preparation of cyclomatic manganese compounds
US3413241A (en) Polyhalogenated polymeric (arylethylene) derivatives
US3749700A (en) Poly(phenylenecarbides)
US2181770A (en) Method of polymerization of 1,2-dihydronaphthalene
JPS5852983B2 (en) Method for producing arylamine
US2777883A (en) Isobutylene allylic monochloride
US2893857A (en) Aminolead compound and herbicidal composition containing same
US2340838A (en) Resinous composition
US3562160A (en) Lubricating oil composition
US3282663A (en) Bicycloheptadiene oligomers
US3311569A (en) Method of making halogen modified poly (alkylene oxide) resins
US2551050A (en) Condensation products of aromatic hydrocarbons and symmetrical dichloroacetone and process for producing same
US3178376A (en) Moldable polymers and process for producing same
US3203898A (en) Lubricating compositions containing condensation polymers of chloromethyl aromatics
US3312588A (en) Method of preserving aqueous organic dispersions from microbial attack
US2238682A (en) Polymeric reaction product of amides with monovinyl acetylenes