Abstract: Polysulfide rubber formulations that become fluid at elevated temperatures but regain the rubbery state upon cooling are disclosed. The products possess a lower permanent set at room temperature and process more easily, particularly in extrusion processes, at elevated temperatures.
Abstract: Polyphosphazene copolymers are prepared which contain randomly distributed units represented by the formulas: ##STR1## wherein X is --CNO.sub.2 R.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 are H, a branched, straight chain or cyclic alkyl group containing from 1 to 12 carbon atoms or mixtures thereof, and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups or mixtures thereof.In the copolymer units represented by the above formulas, all X substituent groups may be the same or they may be mixed and all X' substituent groups may be the same or mixed. In the mixtures, the X substituent groups may be mixtures of different --CNO.sub.2 R.sub.1 R.sub.2 groups and the X' substituent groups may be mixtures of alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups.
Type:
Grant
Filed:
September 8, 1978
Date of Patent:
January 8, 1980
Assignee:
The Firestone Tire & Rubber Company
Inventors:
William L. Hergenrother, Adel F. Halasa
Abstract: Polyphosphazene copolymers are prepared which contain randomly distributed units represented by the formulas: ##STR1## wherein X is --OP(OR).sub.2 in which R is a branched, straight chain or cyclic alkyl group containing from 1 to 12 carbon atoms or mixtures thereof, and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino and mercapto groups. The alkyl groups may vary in carbon chain length or structure within the phosphite or all be the same.In the copolymer units represented by the above formulas, all X substituent groups may be the same or they may be mixed and all X' substituent groups may be the same or mixed. In the mixtures, the X substituent groups may be mixtures of different alkylphosphite groups and the X' substituent groups may be mixtures of different alkoxy, aryloxy, amino and mercaptan groups.
Type:
Grant
Filed:
September 8, 1978
Date of Patent:
January 8, 1980
Assignee:
The Firestone Tire & Rubber Company
Inventors:
William L. Hergenrother, Adel F. Halasa
Abstract: Polyphosphazene copolymers are prepared which certain randomly distributed units represented by the formulas: ##STR1## wherein X is --CR(CN).sub.2 in which R is H, a branched chain, a straight, or cyclic alkyl group containing from 1 to 12 carbon atoms or an aryl group or mixtures thereof, and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups or mixtures thereof.In the copolymer units represented by the above formulas, all X substituent groups may be the same or they may be mixed and all X' substituent groups may be the same or mixed. In the mixtures, the X substituent groups may be mixtures of different --CR(CN).sub.2 groups and the X' substituent groups may be mixtures of alkoxy, alkenyloxy, aryloxy, alkenylaryloxy, amino and mercapto groups or mixtures within each group.
Type:
Grant
Filed:
September 8, 1978
Date of Patent:
December 25, 1979
Assignee:
The Firestone Tire & Rubber Company
Inventors:
William J. Hergenrother, Adel F. Halasa
Abstract: Polyphosphazene copolymers are prepared which contain units represented by the formulas: ##STR1## wherein X is --O--NR.sub.2 in which R is selected from the group consisting of alkyl groups containing from 1 to 8 carbon atoms, and cycloalkyl groups containing from 3 to 12 ring carbon atoms; and wherein X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, amino and mercapto groups.The polymers of the invention can be utilized to form films and may also be utilized in applications such as moldings, coatings and the like.
Type:
Grant
Filed:
November 3, 1978
Date of Patent:
December 18, 1979
Assignee:
The Firestone Tire & Rubber Company
Inventors:
William L. Hergenrother, Adel F. Halasa
Abstract: Urethanes of hydroxybenzotriazoles and hydroxybenzophenones which can be chemically modified upon heating have been found useful in imparting weather resistance to plastic substrates when applied as part of a UV curable resin which can be subsequently heated after cure. UV curable resins containing such urethanes and the use of such resins to treat thermoplastic substrates are also described.
Type:
Grant
Filed:
September 14, 1977
Date of Patent:
December 18, 1979
Assignee:
General Electric Company
Inventors:
Siegfried H. Schroeter, Daniel R. Olson
Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X is represented by ##STR2## wherein R.sub.1 and R.sub.2 are independently selected from a group consisting of substituted or unsubstituted aliphatic, aryl, araryl, alkylaryl and heterocyclic radicals or R.sub.1 and R.sub.2 can be linked to form a cyclic radical and R.sub.3 is an aliphatic hydrocarbon radical or hydrogen, X' is a substituted or unsubstituted alkoxy, aryloxy, amino or mercapto substituent group or mixtures thereof which are compatible with an N-substituted amino substituent and are known in the state of the art of polyphosphazene technology; and 20.ltoreq.(w+y+z).ltoreq.50,000 per polymer and (y+z)>0.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as molding, coatings, foams and the like.
Type:
Grant
Filed:
November 3, 1978
Date of Patent:
December 18, 1979
Assignee:
The Firestone Tire & Rubber Company
Inventors:
William L. Hergenrother, Adel F. Halasa
Abstract: Polyphosphazene copolymers are prepared which are comprised of repeating units represented by the formulas: ##STR1## wherein X is represented by the formula: ##STR2## where R.sub.1 and R.sub.2 are independently selected from the group consisting of substituted and unsubstituted alkyl radicals containing from 1 to 15 carbon atoms, substituted and unsubstituted cycloalkyl, aryl, arylalkyl and heterocyclic ring; X' is selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, mercapto, and amino radicals, and mixtures thereof; and 20.ltoreq.(w+y+z).ltoreq.50,000 per polymer unit.The polyphosphazene polymers of the present invention are prepared by the reaction of a ketoxime and an additional reactant such as alkanol, aryl alcohol, mercaptan, or amine with poly(dichlorophosphazene) in the presence of a tertiary amine. The polymers of this invention may be modified by crosslinking or curing.
Type:
Grant
Filed:
November 3, 1978
Date of Patent:
December 18, 1979
Assignee:
The Firestone Tire & Rubber Company
Inventors:
William L. Hergenrother, Adel F. Halasa
Abstract: More rapid curing of polyepoxide resins is achieved by use of a curing system composed of at least one polymercaptan, at least one catalyst which is a poly[(N,N-dimethylamino)alkyl]ether and/or organic non-quaternized salts thereof derived from organic compounds having at least one acidic group and having a pKa greater than about 3.5 and, optionally, organic sulfide, tertiary phosphine or a tertiary amine having no bridged atoms, having no ether oxygen and having at least one tertiary amine group.
Abstract: Polyphosphazene polymers are prepared which contain repeating units represented by the formulas: ##STR1## wherein X and X' are the same or differnt and are represented by: ##STR2## wherein R.sub.1 is selected from a group consisting of hydrogen and--CN; X' may additionally be selected from the group consisting of substituted and unsubstituted alkoxy, aryloxy, mercapto and amino groups and 20 .ltoreq.(w +y+z) .ltoreq.50,000 per polymer.The polymers of the invention can be utilized to form protective films and can also be utilized in applications such as for molding, coatings, foams and the like.
Type:
Grant
Filed:
September 8, 1978
Date of Patent:
November 20, 1979
Assignee:
The Firestone Tire & Rubber Company
Inventors:
William L. Hergenrother, Adel F. Halasa
Abstract: A novel class of reactive derivatives of polymers containing HS-groups is disclosed in which derivatives a number of the HS-groups are converted to a disulphide group of the formula -S-S-A-Z, where A is a hydrocarbon residue having 1-10 carbon atoms and Z is a group ##STR1## or acid addition salts of the last mentioned group, where n is 2 or 3, R.sup.1 is 2-pyridyl, 5-nitro-2-pyridyl or 4-pyridyl and R.sup.2 is methyl or ethyl. The novel derivatives may be used, for example, as thiolating agents or as carriers for e.g. enzymes or other proteins etc.
Type:
Grant
Filed:
March 2, 1978
Date of Patent:
November 20, 1979
Assignee:
Pharmacia Fine Chemicals AB
Inventors:
Jan P. E. Carlsson, Rolf E. A. V. Axen, Hakan N. Y. Drevin, Goran E. S. Lindgren
Abstract: The use of polysulfide rubbers cured with dilower alkyl tin oxides in hot applied processes and articles formed thereby are disclosed. The compositions are useful as hot applied sealants and in the extrusion of hoses and similar rubber articles.
Abstract: Incorporation of levulinic acid into zinc oxide cured systems based on thiol terminated polysulfide polymers results in cured rubbers capable of extrusion under heat and pressure. The products are useful in sealants and in fabrication of solvent resistant hoses and other extruded articles.
Abstract: Episulfides are reacted with mono, di or trithiols in the presence of tertiary aliphatic amines or tertiary aliphatic phosphines, to form corresponding thioether thiols by a highly selective anionic mechanism. Increasing episulfide-thiol ratios result in polythioether thiols of increasing molecular weights. Using two or more episulfides, block copolymers can be prepared. The reactive terminal thiol functionality and the segmented crystalline and amorphous block structure of the new polymers makes them particularly useful for castable rubber applications.
Abstract: A process of making modified epoxy resins wherein a polyepoxide resin is reacted with a mercaptan compound of the formula HS--R--(COOX).sub.m wherein R is an organic radical having from 1 to 10 carbon atoms, X is hydrogen or a moiety formed by reacting the carboxyl group with a basic compound to form its salt and m is an integer of from 1 to 5. The compounds are reacted in the presence of a tin catalyst to produce resins of the structureB [--S--R--(COOX).sub.m ].sub.nwherein B is the residue from the ring opening reaction of an epoxide group on the polyepoxide resin molecule and the sulfhydryl hydrogen, R, X and m are as defined previously and n is at least 1. The aforementioned resins are produced without the need of a hydrolysis step.The modified epoxy resins are useful in formulating coating compositions having excellent physical and chemical properties. The resins can be dissolved or dispersed in water to form aqueous coating compositions.
Type:
Grant
Filed:
March 13, 1978
Date of Patent:
May 8, 1979
Assignee:
PPG Industries, Inc.
Inventors:
Thomas R. Hockswender, Marvis E. Hartman
Abstract: Ar-cyclic sulfonium arenethiol salts exemplified by the formula: ##STR1## may be converted to their corresponding zwitterion, exemplified by the formula: ##STR2## The latter polymerize very readily upon exposure to mild conditions of heat or radiative energy. The resultant polymers are water-insoluble resins useful as adhesives, coatings, films and the like. The zwitterions containing more than one arenesulfide and cyclic sulfonium group per molecule, crosslink upon exposure to heat to form thermoset resins.
Type:
Grant
Filed:
April 5, 1976
Date of Patent:
December 19, 1978
Assignee:
The Dow Chemical Company
Inventors:
George A. Doorakian, Lawrence G. Duquette
Abstract: This invention relates to a resinous composition curable to an insoluble and infusible resin, which comprises: (i) a compound having at least 2 or more unsaturated cycloacetal groups per molecule, expressed by the formula, ##STR1## (ii) a compound having at least 2 or more mercapto groups (--SH) per molecule, said compound (i) and compound (ii) being mixed in the functional group ratio of 1 : 0.5 - 1.7 and the average total number of the unsaturated cycloacetal groups and mercapto groups being 4 or more.
Abstract: A process for preparing a mixture capable of hardening when exposed to atmospheric moisture, but stable when stored in the absence of moisture, comprises mixing a liquid monomer, oligomer and polymer, liquid oligomer or liquid polymer having at least one terminal mercapto group with a latent hardener comprised of a paste containing anhydrous Na.sub.2 CrO.sub.4 and a water-soluble solvent, such as dimethyl formamide, dimethyl sulfoxide, methanol, ethanol, glycol, glycerine or dioxane. The resulting mixture is useful as a caulking compound.
Type:
Grant
Filed:
May 4, 1976
Date of Patent:
August 29, 1978
Assignee:
Rutgerskwerke Aktiengesellschaft
Inventors:
Gerhard Wilhelm, Lothar Hockenberger, Manfred Soyka, Peter Endruscheit
Abstract: Activated manganese (IV) oxide is used as a curing and vulcanizing agent for polysulfide polymers. By adjusting the following parameters the properties as a curing and vulcanizing agent can be influenced in a predictable way: (a) alkali metal content or foreign metal content; (b) water content; (c) specific surface. A process is described to adjust these parameters.
Abstract: A storage-stable, very quickly hardenable, one-component sealant comprises a mercapto-terminated liquid polymer having uniformly distributed therein a curing agent for the polymer, wherein the curing agent is in a micro-encapsulated state.
Type:
Grant
Filed:
May 4, 1976
Date of Patent:
July 11, 1978
Assignee:
Rutgerswerke Aktiengesellschaft
Inventors:
Lothar Hockenberger, Manfred Soyka, Gerhard Wilhelm
Abstract: cure rate of liquid polysulfide polymer based sealants may be accelerated by incorporation of tetramethylene sulfone therein. This is particularly of importance in one part sealants cured by ZnO.sub.2.