Abstract:
Disclosed is a method of preparing terminally functionalized telechelic polymers using a cationic living polymer product or a terminal tert-chloride chain end of a carbocationic quasiliving polymer product, which comprises quenching the polymer product with an N-substituted pyrrole to thereby functionalize the N-substituted pyrrole at the terminal reactive polymer chain end(s). Also disclosed are the terminal functionalized polyisobuyl N-substituted pyrrole compounds where the polyisobutyl group is substituted at the 2 and 3 position of the N-substituted pyrrole.
Abstract:
A composition having increased electrical conductivity, comprising a liquid hydrocarbon and an anti-static amount of a hydrocarbon soluble copolymer of an alkylvinyl monomer and a cationic vinyl monomer. The copolymer has an alkylvinyl monomer unit to cationic vinyl monomer unit ratio of from about 1:1 to about 10:1, and has an average molecular weight of from about 800 to about 1,000,000. Other related compositions and methods for measuring electrical conductivity of liquids are also disclosed.
Abstract:
Fuel compositions having improved low-temperature flow properties comprise wax-containing residual or flashed distillate hydrocarbon fuel having incorporated therein a minor amount of a copolymer of (1) an olefinically unsaturated compound containing an unbranched saturated hydrocarbon chain with at least 14 carbon atoms and (2) a heterocyclic compound which contains an olefinically unsaturated double bond not attached directly to a hetero atom and of which the ring carbon atoms linked to a hetero atom do not carry monovalent hydrocarbon groups, the heterocyclic compound most preferably being 4-vinylpyridine.
Abstract:
A method of transporting waxy crudes through conduits at reduced friction and preventing wax separation or precipitation so as to inhibit plugging and flow restriction and improve the pour point properties of the crude by adding to such waxy crudes a small amount of a polymeric material containing aliphatic hydrocarbon side chains of at least 14 carbon atoms. This invention relates to decreasing friction loss in flowing waxy crudes through conduits, generally over great distances but also over short distances such as in well fracturing processes and also to improving the pour point of waxy crudes. More particularly, the invention is directed to crude oil compositions comprising a waxy crude oil and fractions thereof and polymers having aliphatic hydrocarbon side chains with at least 14 carbon atoms, so as to reduce the pour point, prevent wax separation and reduce its friction loss due to flow through pipelines over great distances and short distances.
Abstract:
As additives to oils there are used copolymers made by a process which involves partially polymerizing an ethylenically unsaturated monomeric material, adding a nitrogen-containing ethylenically unsaturated monomer thereto, and then completing the polymerization, the monomer mixture being such as to provide an oil-soluble copolymer (see Group IV(a)). Oils specified are fuel oils, mineral lubricating oils, kerosenes and synthetic lubricants, e.g. esters of sebacic and phosphoric acid. As monomers for use in preparing the prepolymer there are specified esters of acrylic and substituted acrylic acids, esters of maleic, fumaric and itaconic acids, styrenes, unsaturated nitrites, ethers, thioethers and ketones and vinyl and vinylidene chlorides. Nitrogen-containing monomers specified are vinyl lactams, oxazolidones, unides, ureas and pyridines, aminoalkyl styrenes, acrylates, ethers and thioethers and unsaturated hydrazides.ALSO:Oil-soluble copolymers are obtained by: (A) forming a polymerizing mixture of (1) one or more ethylenically unsaturated monomers and (2) a prepolymer derived from one or more monoethylenically unsaturated monomers and which is present in an amount of from 40 to 85% by weight of the combined weight of monomer and prepolymer, the mixture undergoing polymerization under the influence of a free-radical initiator, (B) adding to the polymerizing mixture at least one monoethylenically unsaturated nitrogenous monomer which contains a trivalent nitrogen atom bonded to at least two atoms at least one of which is carbon, and which is either an imide having non-terminal unsaturation or is a compound containing a terminal methylene group, and (C) continuing polymerization of the resulting mixture, the monomer mixture being such as to provide an oil-soluble copolymer containing nitrogenous monomer in an amount between about 1% and 30% by weight of the final copolymer. As monomers for forming the prepolymer there are listed alkyl acrylates, alkacrylates, phenacrylates and chloroacrylates, esters of acrylic and methacrylic acids in which the alcohol portion contains a hetero atom, e.g. oxygen, nitrogen, sulphur or phosphorus, vinyl esters of fatty acids, alkyl maleates, fumarates and itaconates, styrene, alkyl styrenes, p-chlorostyrene, acrylonitrile, methacrylonitrile, vinyl ethers, vinyl thioethers, vinyl ketones and vinyl and vinylidene chlorides. Nitrogen containing monomers listed are N-vinyl lactams, N-vinyl oxazolidones, cyclic N-vinyl imides, N-vinyl ureas, N-vinyl carboxylic amides, N-acryloxy and N-methacryloxy lactams, N-acrylamido and N-methacrylamido lactams, N-alkyl acrylamides and methacrylamides, N-vinyl amines, vinyl pyridines, aminostyrenes, aminoalkyl vinyl ethers and thioethers, aminoalkyl acrylates and methacrylates, and unsaturated hydrazides. Free-radical initiators listed are azo compounds, peroxides, hydroperoxides, peresters and combinations of hydroperoxides and quaternary ammonium salts. Polymerization may be carried out in bulk or, preferably, in solution in an organic solvent. The examples describe the application of the above process to the following combinations of monomers: (1) cetyl-stearyl methacrylate, lauryl-myristyl methacrylate, butyl methacrylate and N-vinyl pyrrolidinone; (2) stearyl methacrylate, styrene and N-vinyl pyrrolidinone; (3) vinyl stearate, vinyl-2-ethyl hexoate and N-vinyl pyrrolidinone; (4) vinyl stearate, dodecyl methacrylate and N-vinyl-5-methyl pyrrolidinone; (5) dilauryl fumarate, vinyl acetate and N-vinyl pyrrolidinone; (6) distearyl maleate and N-vinyl pyrrolidinone; (7) distearyl itaconate and N-vinyl pyrrolidinone; (8) cetyl-stearyl fumarate vinyl acetate and N-vinyl caprolactam; (9) lauryl-myristyl methacrylate and N-vinyl oxazolidone; (10) as in (9) but including also dimethaminoethyl methacrylate; (11) lauryl methacrylate and N-vinyl succinimide; (12) lauryl methacrylate and N-(8-methacryloxy-3,6-dioxaoctyl) pyrrolidinone; (13) lauryl methacrylate and N-n-butylacrylamide; (14) lauryl, stearyl, butyl and dimethylaminoethyl methacrylates; (15) lauryl and dimethylaminoethyl methacrylates and N-vinyl pyrrolidinone; (16) lauryl methacrylate and N-vinyl-N1-dimethylamino-ethylethyleneurea; (17) lauryl methacrylate and N-vinyl-N-methylacetamide; (18) lauryl methacrylate and 4-vinyl pyridine; (19) lauryl methacrylate and N-(2-methacryloxyethyl)-2-oxazolidone; (20) octyl methacrylate and 1-(2-methacryloxyethyl) - 2,4,4 - trimethylpyrrolidine; (21) lauryl methacrylate and diethylaminoethyl vinyl thioether; (22) dodecyl methacrylate and N-methacrylyl-N,N-dimethyl hydrazide; and (23) lauryl-myristyl methacrylate and N-methyl maleimide.ALSO:Ethylenically unsaturated nitrogen-containing compounds are prepared as follows:- (a) N-acryloxyalkyl or N-methacryloxyalkyl lactams are prepared by reacting N-hydroxyalkyl lactams with lower alkyl methacrylates or acryloyl or methacryloyl halides, e.g. N-(2-hydroxyethyl)pyrrolidinone and methyl methacrylate are heated in the presence of sodium methoxide to produce N-(2-methacryloxyethyl)pyrolidinone; (b) N-acrylamidoalkyl or N-methacrylamidoalkyl lactams are prepared by reacting acryloyl and methacryloyl halides with N-(aminoalkyl) lactams, e.g. methacryloyl chloride and N-2-aminoethyl-3,5.5-trimethylpyrrolidinone are heated together in the presence of sodium carbonate to produce 2-methacrylamidoethyl- 3,5.5-trimethyl pyrrolidinone; (c) N-acryloyl or N-methacryloyl pyrrolidinones are prepared by reacting pyrrolidinone with acryloyl or methacryloyl halides; (d) 1-(2-hydroxyethyl)- 2,4,4-trimethylpyrrolidine is reacted with methyl methacrylate in the presence of sodium methoxide to produce 1-(2-methacryloxyethyl)- 2,4,4-trimethylpyrrolidine.
Abstract:
Disclosed is a method of preparing terminally functionalized telechelic polymers using a cationic living polymer product or a terminal tert-chloride chain end of a carbocationic quasiliving polymer product, which comprises quenching the polymer product with an N-substituted pyrrole to thereby functionalize the N-substituted pyrrole at the terminal reactive polymer chain end(s). Also disclosed are the terminal functionalized polyisobuyl N-substituted pyrrole compounds where the polyisobutyl group is substituted at the 2 and 3 position of the N-substituted pyrrole.
Abstract:
It has been discovered that less expensive, and in some cases synergistically effective anti-static additive blends may be added to hydrocarbon fuels to improve the conductivity thereof. The blend includes an anti-static amount of at least one hydrocarbon soluble copolymer of an alkylvinyl monomer and a cationic vinyl monomer and an anti-static amount of at least one hydrocarbon soluble polysulfone copolymer of at least one olefin and sulfur dioxide. Optional ingredients include polymeric polyamines and aryl sulfonic acids.
Abstract:
Telomeric hydrocarbon phosphorus compounds and hydrocarbon compositions containing said compounds are described. The telomeric hydrocarbon phosphorus compounds are represented by the formula: ##STR1## in which R is a hydrocarbon radical having from 1 to 18 carbon atoms and n has a value from 0 to 100.