Fluorine Containing Monomer Contains Nitrogen Atom Patents (Class 526/248)
  • Patent number: 5556929
    Abstract: An ocular lens material made of a copolymer obtained by polymerizing copolymerizable components comprising (A) a fluorine-containing di(meth)acrylate having urethane bonds, of the formula (I): ##STR1## wherein each of R.sup.1 and R.sup.2 independently represents a hydrogen atom or a methyl group, each of R.sup.3 and R.sup.4 independently represents a C.sub.5-15 alkylene group, R.sup.5 represents a C.sub.1-20 alkylene group containing from 1 to 20 fluorine atoms, each of m and n independently represents an integer of from 1 to 5, and each of x and y independently represents 0 or 1, (B) a silicone-containing di(meth)acrylate having urethane bonds, of the formula (II): ##STR2## wherein each of R.sup.6 and R.sup.7 independently represents a hydrogen atom or a methyl group, each of R.sup.8 and R.sup.9 independently represents a C.sub.1-10 alkylene group or a C.sub.2-10 ether group, R.sup.
    Type: Grant
    Filed: January 2, 1996
    Date of Patent: September 17, 1996
    Assignees: Menicon Co., Ltd., Shin-Etsu Chemical Co., Ltd.
    Inventors: Yasuhiro Yokoyama, Yuriko Watanabe, Akinori Okumura, Shoji Ichinohe, Toshio Yamazaki
  • Patent number: 5530067
    Abstract: Electrostatic toners comprising polymeric dyes comprising of (1) discrete segments that are dispersible in highly fluorinated solvents and (2) discrete color-imparting segments. These toners can be prepared by a means of a polymerization process, wherein macromers containing highly fluorinated dispersible segments are grafted onto a polymer having chromophores attached thereto.
    Type: Grant
    Filed: May 17, 1994
    Date of Patent: June 25, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: S. Prabhakara Rao, Terrance P. Smith
  • Patent number: 5498639
    Abstract: Polymeric compositions are derived from copolymers of .alpha.,.beta., .beta.-trifluorostyrene with a variety of substituted .alpha.,.beta.,.beta.-trifluorostyrenes. These compositions are suitable for use as membranes, particularly as ion-exchange membranes, and most particularly as solid polymer electrolytes in electrochemical applications, such as, for example, electrochemical fuel cells.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: March 12, 1996
    Assignee: Ballard Power Systems Inc.
    Inventors: Jinzhu Wei, Charles Stone, Alfred E. Steck
  • Patent number: 5468812
    Abstract: Polymerizable, organic-soluble, oligomeric fluorochemical surfactant compositions having at least two pendent fluoroaliphatic groups, at least two organic-solubilizing groups, and a pendent polymerizable olefinic group. Also a method of preparing such surfactant compositions. The compositions reduce the surface energy of acrylate-containing mixtures and acrylate-based pressure-sensitive adhesives. They can be used in preparing acrylate-based pressure-sensitive adhesives that coat well due to the presence of the surfactant and maintain adhesive performance upon aging.
    Type: Grant
    Filed: September 26, 1994
    Date of Patent: November 21, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Imelda A. Muggli, Roger R. Alm
  • Patent number: 5444136
    Abstract: Nonlinearly optically active monomer species comprising at least two carbon-carbon activated double bonds, i.e., the polymerization of which is facilitated by the presence of an electron attracting function, and a non-centrosymmetric system of pi (.pi.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: August 22, 1995
    Assignee: Flamel Technologies
    Inventors: Yves Camberlin, Gerard Mignani, Remi Meyrueix, Gilles Tapolsky
  • Patent number: 5426164
    Abstract: A polymer has at least one photoactive site and more than one perfluorocyclobutane group. New monomers containing photoactive sites or photoactive precursors and at least one perfluorovinyl group are useful for making such polymers. Processes of making such polymers and the monomers from which they are made are disclosed. The polymers are useful in coatings, photoresists, and the like.
    Type: Grant
    Filed: December 24, 1992
    Date of Patent: June 20, 1995
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, W. Frank Richey, Katherine S. Clement, Eric S. Moyer, Marius W. Sorenson
  • Patent number: 5422411
    Abstract: Polymeric compositions are derived from copolymers of .alpha.,.beta.,.beta.-trifluorostyrene with a variety of substituted .alpha.,.beta.,.beta.-trifluorostyrenes. These compositions are suitable for use as membranes, particularly as ion-exchange membranes, and most particularly as solid polymer electrolytes in electrochemical applications, such as, for example, electrochemical fuel cells.
    Type: Grant
    Filed: September 21, 1993
    Date of Patent: June 6, 1995
    Assignee: Ballard Power Systems Inc.
    Inventors: Jinzhu Wei, Charles Stone, Alfred E. Steck
  • Patent number: 5418277
    Abstract: An aqueous dye or pigment ink particularly adapted for ink jet printing containing a fluorinated block copolymer prepared from a fluorinated oxazoline or oxazine. Resulting inks exhibit high print quality over a range of papers.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: May 23, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Sheau-Hwa Ma, Jose M. Rodriguez-Parada
  • Patent number: 5408010
    Abstract: Fluoroalkyl-substituted maleic anhydride polymers, substrates treated therewith, and to novel processes for preparing and using the same. The polymers can be prepared by reacting: (1) terminally unsaturated alkenylamines or alcohols (e.g. allyl amine or alcohol, or diallyl amine) with maleic anhydride polymers, and (2) the resulting polymeric amides or esters with fluoroalkyl iodides in the presence of a free radical initiator. Dehydroiodination of the resulting product with base yields novel polymeric products which provide oil- and water-repellency as well as soil-resistance when applied to substrates, particularly nylon fibers.
    Type: Grant
    Filed: July 28, 1994
    Date of Patent: April 18, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Donald D. May
  • Patent number: 5393803
    Abstract: A maleimide polymer comprises units derived from a maleimide derivative represented by the following general formula (I): ##STR1## where R.sup.1 is a hydrogen atom or a methyl group, and R.sup.2 is an alkyl, alkenyl or aryl group, each of which groups is substituted by at least one organosiloxane group or fluorine atom, or comprises a copolymer of (1) a maleimide derivative represented by the formula (I) but in which R.sup.2 may be hydrogen or any optionally substituted aliphatic hydrocarbon or aryl group with (2) an alkyl or fluoroalkyl methacrylate or an organosiloxy styrene- or organosiloxy-(meth)acrylic acid derivative.The polymer material may be formulated into contact lenses high in oxygen permeability and having good mechanical properties.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: February 28, 1995
    Inventors: Teiji Kawano, Mitsuru Yokota
  • Patent number: 5382639
    Abstract: Novel polymers are disclosed which can be used to prepare water-based compositions are disclosed having the capability of forming a uniform, low surface-energy, thin film on a substrate. Such compositions comprise a polymer having at least one fluoroaliphatic moiety and at least one anionic moiety, and a novel polymer having at least one fluoroaliphatic moiety and at least one oxazoline moiety.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: January 17, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: George G. I. Moore, Dong-Wei Zhu
  • Patent number: 5374701
    Abstract: Diarylacetylenes and diarylenamines are synthesized from a Schiff's base and an N-arylmethylheterocycle; these compounds are useful as intermediates for a variety of polymers; in particular an efficient process is provided for producing diaryl acetylenes useful in the efficient production of acetylene group-containing polymers which can be cross-linked to produce high strength polymers free of structural defects such as conventionally arise as a result of liberation of volatiles during the cross-linking.
    Type: Grant
    Filed: May 4, 1993
    Date of Patent: December 20, 1994
    Inventors: Allan S. Hay, Martino Paventi
  • Patent number: 5364917
    Abstract: A process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having aromatic polyester, aromatic polyamide, or polyimide groups or combination thereof, at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed. Chain extending oligomers of polymers having poor processing characteristics by this process results in polymers which are more easily processed. For instance, perfluorocyclobutane groups formed in an extruder to chain lengthen polyimide oligomers, in effect, render polyimides extrudable. The polymer formed by the method preferably has polyimide groups. New monomers and polymers having imide and perfluorovinyl or perfluorocyclobutane structures, respectively, are prepared.
    Type: Grant
    Filed: December 1, 1993
    Date of Patent: November 15, 1994
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, W. Frank Richey, Katherine S. Clement, Bobby R. Ezzell
  • Patent number: 5326670
    Abstract: A resist composition for forming a upper resist layer and a process for forming a pattern thereby are disclosed. This resist comprises an azide compound and a polyacrylic copolymer of the following formula (1): ##STR1## wherein, R.sub.1 means CH.sub.3, CF.sub.3, CN, CH.sub.2 OH, or CH.sub.2 CO.sub.2 R, wherein R means an alkyl having 1 to 5 carbon atomsR.sub.2 means a hydrocarbon radical having at least one Si,R.sub.3 means OH, O--C(CH.sub.3).sub.3, NH.sub.2 , or NHCH.sub.2 OH, and, a ratio of n to m is more than 0 and is 1 or less than 1.Whereby a finely-resolved resist pattern is obtained by a preset process for forming the resist pattern.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: July 5, 1994
    Assignee: Fujitsu Limited
    Inventors: Akiko Kotachi, Satoshi Takechi
  • Patent number: 5314975
    Abstract: The present invention provides novel fluorinated acrylamide silane monomers which are useful as adhesion promoting agents in optical fiber cladding compositions. Polymerization of the novel monomers, optionally in the presence compatible ethylenically-unsaturated monomers, provides homopolymers and copolymers which are useful as non-wetting agents.
    Type: Grant
    Filed: January 28, 1993
    Date of Patent: May 24, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Stefan A. Babirad, Dean M. Moren, Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
  • Patent number: 5292924
    Abstract: .alpha.-Fluoro-substituted N-acryloylamino acid derivatives of the formula ##STR1## are used to make polymers optionally for chromatographic resolution of racemates into their enantiomers. The fluorine atom improves performance in many instances.
    Type: Grant
    Filed: November 13, 1992
    Date of Patent: March 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Grosser, Walter Lange, Bruno Bomer, Dieter Arlt, Dietmar Bielefeldt
  • Patent number: 5274008
    Abstract: When molding shaped articles such as contact lenses from monomeric mixtures containing silicone monomers and hydrophilic monomers, the wettability of the resulting article is improved by using a mold material produced from a resin comprising a copolymer of an alpha, beta, olefinically unsaturated mononitrile and at least one comonomer to enhance melt processability.
    Type: Grant
    Filed: January 14, 1993
    Date of Patent: December 28, 1993
    Assignee: Bausch & Lomb Incorporated
    Inventor: Yu-Chin Lai
  • Patent number: 5264511
    Abstract: Monomers, B-stage polymers, C-stage polymers, cured polymers and electricy conducting polymers of acetylene-terminated aromatic monomers containing three benzene rings separated by ethylene groups are disclosed. These new polymers can withstand aggressive environments and are particularly adapted for use in high temperature composites in addition to the utilization of their electrical conducting properties. Preparation of these materials is accomplished by melt polymerization and heat treatment at high temperatures.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: November 23, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Theordore R. Walton
  • Patent number: 5256731
    Abstract: Polymers based on ethylenically unsaturated monomers contain at least 0.1% by weight of monomer units comprising specific ethylenically unsaturated, fluorine-containing and polymerization-capable or copolymerization-capable urethane derivatives (see formula I).The process for the preparation of the polymers or copolymers from the monomers from which they are built up by free-radical initiated polymerization or copolymerization, preferably by a method of emulsion polymerization.The use of the polymers as a starting material for the production of films, sheets, fibers, adhesives, paints, compression-molding compositions and moldings, as a thickener in aqueous preparations, as an impregnant, binder or coating agent for various industrial or chemotechnological areas of application.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: October 26, 1993
    Assignee: Hoechst AG
    Inventors: Hans-Ullrich Huth, Karl-Hans Angelmayer
  • Patent number: 5256747
    Abstract: Perfluoroelastomers characterized by low molecular weight and freedom form color-forming impurities can be prepared by pyrolysis techniques, and are useful in pellicle coatings and other optical applications.
    Type: Grant
    Filed: December 23, 1991
    Date of Patent: October 26, 1993
    Inventors: Leo Ojakaar, Anestis L. Logothetis
  • Patent number: 5247035
    Abstract: At least 95% tetrahydrofuran soluble polymers are obtainable by copolymerization of a monomer mixture ofA) from 1 to 99% by weight of at least one at least 98% pure monomer of the general formula ICH.sub.2 .dbd.C(E)CH.sub.2 --O--CH.sub.2 C(E').dbd.CH.sub.2 Iwhere E and E' have been selected from the group consisting of --COOR.sup.1, --COR.sup.1, --CONR.sup.2 R.sup.3 and --CN and R.sup.1, R.sup.2 and R.sup.3 are each defined as follows:R.sup.1 =H, alkyl, cycloalkyl, cycloalkylalkyl, wherein the cycloalkyl rings may be alkyl- or alkoxy-monosubstituted, -disubstituted or -trisubstituted, hydroxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, aryl, arylalkyl, wherein the aryl groups may carry up to three of the following groups: halogen, alkyl, alkoxy, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, nitrilo, nitro, amino, alkylamino, dialkylamino;R.sup.2, R.sup.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: September 21, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Siegmund Besecke, Andreas Deckers, Harald Lauke
  • Patent number: 5247042
    Abstract: This invention provides novel side chain polymers which exhibit nonlinear optical response, and which have utility as a transparent optical component in all-optical and electrooptical light switch and light modulator devices.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: September 21, 1993
    Assignee: Hoechst Celanese Corp.
    Inventors: Diane E. Allen, Ronald N. DeMartino, Hyun-Nam Yoon
  • Patent number: 5225515
    Abstract: Polybenzazole polymers may contain perfluorocyclobutane rings to provide a flexible moiety which is stable at high temperatures.
    Type: Grant
    Filed: April 17, 1991
    Date of Patent: July 6, 1993
    Assignee: The Dow Chemical Company
    Inventors: Zenon Lysenko, William J. Harris
  • Patent number: 5216097
    Abstract: The invention provides polymers or copolymers which are prepared by the polymerization of the reaction product of a diisocyanate with a perfluoro compound or an epichlorhydrinadduct thereof and (meth)acrylic esters of a three hydroxyl groups containing compound. Furthermore, the invention relates to fluoroacrylic monomers, a process for preparing the polymers or copolymers and a treatment agent comprising the polymers or copolymers of the invention and an environmentally acceptable solvent. Polymers and copolymers of the invention can be used for making textiles, papers, non-woven articles, leather, plastic, wood, metal, stone and cement water and oil repellent.
    Type: Grant
    Filed: April 21, 1992
    Date of Patent: June 1, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Kathy Allewaert, Dirk Coppens, Franceska Fieuws
  • Patent number: 5212269
    Abstract: Processible chromophoric polymers having nonlinear optical properties and wherein the chromophore is present in and is a part of the polymer backbone, including substantially all of the monomer or repeat units, with the dipole moments pointing in the same direction (head-to-tail) along the polymer backbone. Such polymers include phenylene, phenylene vinylene, stilbenylene, phenyl piperdine, and coumarin polymers.
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: May 18, 1993
    Inventors: John Fischer, Ronald Henry, James Hoover, Geoffrey Lindsay, John Stenger-Smith, Andrew P. Chafin
  • Patent number: 5198513
    Abstract: A compound having at least one perfluorovinyl group and at least one functional group is suitable for reacting with and/or forming polymers. The compound is preferably of Formula I:(G)n-R-(X--CF.dbd.CF.sub.2).sub.mwherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of (XCF.dbd.CF.sub.2) groups; and G represents any reactive functional group or a group convertible into a reactive functional groups.A process for preparing a compound of Formula I comprises the steps of:(a) preparing a 2-halotetrafluoro compound of the Formula III:(Q--CF.sub.2 --CF.sub.2 -X).sub.m -R-(G").sub.
    Type: Grant
    Filed: March 12, 1991
    Date of Patent: March 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell, W. Frank Richey
  • Patent number: 5187234
    Abstract: This invention provides novel vinyl polymers with pendant side chains which exhibit nonlinear optical response. The polymers have utility as a transparent optical media in optical devices.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: February 16, 1993
    Assignee: Hoechst Celanese Corp.
    Inventors: Thomas M. Leslie, Ching F. Shu, Karsten Blatter, Ronald DeMartino, Frank Battito
  • Patent number: 5187237
    Abstract: The epoxy resins according to the invention demonstrate the following structure: ##STR1## The cross-linked epoxy resins exhibit non-linear optical properties.
    Type: Grant
    Filed: September 17, 1991
    Date of Patent: February 16, 1993
    Assignee: Siemens Aktiengesellschaft
    Inventors: Jens Nordmann, Heinz Hacker
  • Patent number: 5177165
    Abstract: A new class of polymerizable surfactants, useful for modifying the surfaces of polymeric objects, which are described by the formula:DC[A.sub.x B.sub.y ]wherein A is at least one ethylenically unsaturated hydrophilic monomer, B is at least one ethylenically unsaturated hydrophobic monomer, C is a functional chain transfer agent, D is an ethylenically unsaturated end group, y is within the range from about 0.1 to about 0.9, and x+y=1. Also disclosed are random copolymer precursors of such polymerizable surfactants.
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: January 5, 1993
    Assignee: Bausch & Lomb Incorporated
    Inventors: Paul L. Valint, Jr., Joseph A. McGee
  • Patent number: 5171803
    Abstract: In one embodiment this invention provides novel side chain copolymers which exhibit nonlinear optical response, and which have utility as a transparent optical component in all-optical and electrooptical light switch and light modulator devices.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: December 15, 1992
    Assignee: Hoechst Celanese Corp.
    Inventors: Connie R. Walton, Brian B. Marr, Anthony J. East
  • Patent number: 5166283
    Abstract: A polymer having dihydropyridine rings or dihydrotriazine rings as main constitutional units, an ethynyl- or cyanato-terminated Schiff's compound which is a starting material for producing the polymer, and applications of the polymer.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: November 24, 1992
    Assignee: Hitachi Ltd.
    Inventors: Akio Nishikawa, Tohru Koyama, Hideki Asano, Toshikazu Narahara
  • Patent number: 5162468
    Abstract: Compounds have a structure represented by Formula I:CF.sub.2 .dbd.CF--X--R--(X--CF.dbd.CF.sub.2).sub.mwherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF.dbd.CF.sub.2 ; and m is an integer of from 1 to about 3. Polymers formed from such compounds are also prepared. The compounds are preferably prepared by a method by a process comprising the steps of:(a) forming a salt having anion corresponding to a compound of Formula II:HX--R--(XH.sub.m);wherein X, R and m are as defined for Formula I:(b) reacting the salt with a 1,2-dihalo-1,1,2,2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III:Z--CF.sub.2 CF.sub.2 --X--R--(X--CF.sub.2 CF.sub.2 --Z).sub.
    Type: Grant
    Filed: March 12, 1991
    Date of Patent: November 10, 1992
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, Katherine S. Clement, Bobby R. Ezzell
  • Patent number: 5142010
    Abstract: An antimicrobial polymerizable compound and polymers resulting therefrom, the compound being ##STR1## wherein A is any polymerizable group; Q is phenylene; and R is --(CF.sub.2).sub.y CF.sub.3 wherein y=1-20, --(CH.sub.2).sub.x --O--C.sub.x H.sub.2x+1 wherein x=1-25, --(CH.sub.2 CH.sub.2 O).sub.n (CH.sub.2 CHCH.sub.3 O).sub.m (CH.sub.2 CH.sub.2 O).sub.p T wherein T=--H or any branched or unbranched C.sub.1-20 alkyl and n, m, and p=0-99 and m+n+p.gtoreq.1, --CHR'COOH wherein R' is H or any naturally occurring amino acid side chain, --(CH.sub.2).sub.x COOH, --(CH.sub.2).sub.x --(CH.sub.2 CH.sub.2 --O).sub.n --(CH.sub.2 CHCH.sub.3 O).sub.m (CH.sub.2 CH.sub.2 O).sub.p --CO--NH--CH.sub.2 --CH.dbd.CH.sub.2, --(CH.sub.2).sub.x --CO--NH--CH.sub.2 --CH.dbd.CH.sub.2, or --(CH.sub.2).sub.x --O--C--COH.dbd.CH.sub.2. The resulting polymers are useful in any variety of applications requiring an antimicrobial agent or an active sanitizer or disinfectant including caulks, mortars, films and coatings, adhesives and the like.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: August 25, 1992
    Assignee: H. B. Fuller Licensing & Financing Inc.
    Inventor: Alan D. Olstein
  • Patent number: 5100954
    Abstract: A soilresisting agent containing, as an effective component, a copolymer of (I) a fluorine-containing urethane compound containing a (meth)acryloyl group or an allyl group, and a polyfluoroalkyl group, obtained by reacting (a) a polyfunctional isocyanate having at least trifunctionality, (b) a hydroxy compound containing a (meth)acryloyl group or an allyl group, and (c) a hydroxy compound having a polyfluoroalkyl group, and (II) a copolymerizable compound other than said fluorine-containing urethane compound.
    Type: Grant
    Filed: August 15, 1990
    Date of Patent: March 31, 1992
    Assignee: Asahi Glass Company Ltd.
    Inventors: Katsuji Itoh, Gen-ichirou En-na, Sachio Otoshi
  • Patent number: 5098971
    Abstract: A fluorine-containing thermosetting resin having a three-dimensional crosslinking structure is obtained by polymerizing a bismaleimide compound having the formula, ##STR1## wherein Rf is fluorine, CF.sub.3, C.sub.2 F.sub.5 or C.sub.3 F.sub.7. The resin is excellent in moldability, thermal resistance and electric properties, has a low dielectric constant, is hence suitable as a molding material and can be used for molding materials, wiring boards, layer insulation films of LSI, etc.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: March 24, 1992
    Assignees: Hitachi, Ltd., Central Glass, Co.
    Inventors: Akira Nagai, Shin Nishimura, Akio Takahashi, Masamichi Maruta, Akihiro Fukui
  • Patent number: 5085975
    Abstract: Polymerizable compounds comprising perfluoroalkyl groups, reproduction layers containing these compounds, and use of the reproduction layers for waterless offset printing. The novel polymerizable compounds comprise at least two acryloyl or methacryloyl groups and at least one perfluoroalkyl group which is linked to the molecule through a functional group, in particular, an ester or amide function. The compounds can be prepared, for example, from hydroxyl group-containing acrylates or methacrylates and perfluoroalkyl group-containing carboxylic acid chlorides, in the presence of an amine or from perfluoroalkyl group-containing carboxylic acid derivatives and reactive acryloyloxy or methacryloyloxy compounds. Oligomeric compounds can additionally be synthesized from the above-mentioned compounds by linking, for example, with diisocyanates.
    Type: Grant
    Filed: October 23, 1989
    Date of Patent: February 4, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Werner H. Mueller
  • Patent number: 5084498
    Abstract: A copolymer of an unsaturated fluoro compound with a vinyl ether and, optionally, with at least one additional ethylenically unsaturated monomer can be stabilized against gelling by the addition, either to the copolymerization reaction or to the copolymer in solution or in aqueous dispersion, of a 2,2-unsubstituted alicyclic 1,3-diketone in the presence of the enolate ion of said ketone, which enolate may be formed in situ. Solutions and dispersions of such copolymers are very useful in hard, weather-resistant finishes, for example, those used for bridge ironwork and architectural maintenance and in automotive applications.
    Type: Grant
    Filed: October 17, 1990
    Date of Patent: January 28, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Norman M. van Gulick
  • Patent number: 5081198
    Abstract: A tough, high performance polyimide is provided by reacting a triple bond conjugated with an aromatic ring in a bisethynyl compound with the active double bond in a compound containing a double bond activated toward the formation of a Diels-Adler type adduct, especially a bismaleimide, a biscitraconimide, or a benzoquinone, or mixtures thereof. Addition curing of this product produces a highly linear polymeric structure and heat treating the highly linear polymeric structure produces a thermally-stable aromatic addition-type thermoplastic polyimide, which finds utility in the preparation of molding compounds, adhesive compositions, and polymer matrix composites.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: January 14, 1992
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Ruth H. Pater
  • Patent number: 5079319
    Abstract: Vinyl unsaturated copolymers are described which are obtained in a two-step process and which consist of monomeric units A, B, C, D and E, copolymerized in a first step, and in a second step reacted with a reactive vinyl monomer M.sub.v, and in which A is a siloxane or fluorine containing vinyl monomer, 30-70% by weight; B is NN-dimethylacrylamide or N-vinylpyrrolidone, 30-70% by weight; C is an active hydrogen containing vinyl monomer, 0.5-25% by weight; D are other copolymerizable comonomers, 0-30% by weight, and E is a chain transfer agent, 0-10 mol percent. M.sub.v is a vinyl unsaturated isocyanate.These vinyl unsaturated polymers are useful, either by themselves or in combination with other copolymerizable vinyl monomers, as heat or UV-curable coatings or glass, plastic, wood, paper, textiles, metal or ceramics, said coatings possessing low surface energies and low refractive indices.
    Type: Grant
    Filed: February 13, 1991
    Date of Patent: January 7, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl F. Mueller
  • Patent number: 5066746
    Abstract: The present invention is a process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed wherein at least about 0.05 mole percent of the monomer, have at least 3 dimerizable perfluorovinyl groups and polymers prepared thereby.
    Type: Grant
    Filed: June 7, 1990
    Date of Patent: November 19, 1991
    Assignee: The Dow Chemical Company
    Inventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell
  • Patent number: 5037917
    Abstract: A process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed. The invention includes polymers having a backbone comprising hydrocarbyl groups, perfluorocyclobutane rings and non-carbon atoms and polymers of at least 10,000 molecular weight having repeating units [O-(CFR.sub.f).sub.n -O-perfluorocyclobutane].
    Type: Grant
    Filed: June 9, 1989
    Date of Patent: August 6, 1991
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, Katherine S. Clement, W. Frank Richey, Bobby R. Ezzell
  • Patent number: 5037918
    Abstract: A crosslinked polymer having perfluorocyclobutane rings is prepared in a process comprising the steps of: (a) contacting monomers having two dimerizable perfluorovinyl groups; (b) exposing the monomers to sufficient heat and for a sufficient time that a (linear) polymer containing perfluorocyclobutane rings is formed; and (c) exposing the polymer to sufficient crosslinking initiating means and for a sufficient time such that crosslinking occurs. Crosslinked polymers, so prepared are novel and have tensile strength and other physical proeprties enhanced over the properties of the corresponding linear polymer.
    Type: Grant
    Filed: December 15, 1989
    Date of Patent: August 6, 1991
    Assignee: The Dow Chemical Company
    Inventor: David A. Babb
  • Patent number: 5006624
    Abstract: Water-soluble of water-dispersible, crosslinkable polymeric surfactants having fluorocarbon and ionic moieties are disclosed. Such surfactants can be cured into tough, solvent resistant, low critical surface tension coatings useful for protective finishes on metal, plastics and fabrics.
    Type: Grant
    Filed: March 1, 1990
    Date of Patent: April 9, 1991
    Assignee: The Dow Chemical Company
    Inventors: Donald L. Schmidt, Charles E. Coburn, Perry J. McCrackin
  • Patent number: 5001198
    Abstract: A novel fluorine-containing polymeric compound represented by the general formula--CH.sub.2 --CH[(CH.sub.2).sub.a --NH.sub.2 ]}.sub.m-n--CH.sub.2 --CH[(CH.sub.2).sub.a --NH--CO--NH--CH.sub.2).sub.a Rf]}.sub.n,in which Rf is a perfluoroalkyl group having 6 to 15 carbon atoms, m is a positive integer in the range from 10 to 1500, n is a positive integer smaller than 0.7 m and a is 0 or 1, is prepared by the reaction of, when a is 0, a polyvinylamine of the formula --CH.sub.2 --CHNH.sub.2 ].sub.m, with an alkyl perfluoroalkanoate of the formula Rf--CO--OR, in which R is an alkyl group having 1 to 5 carbon atoms, or, when a is 1, a polyallylamine of the formula --CH.sub.2 --CH(CH.sub.2 --NH.sub.2)].sub.m, with a perfluoroalkylmethyl isocyanate of the formula RfCH.sub.2 --NCO. Despite the high fluorine content, the polymer is soluble in at least one kind of organic solvents so that Langmuir-Blodgett's films can be prepared from a solution of the polymer.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: March 19, 1991
    Assignee: Director General of Agency of Industrial Science and Technology
    Inventors: Akira Sekiya, Masanori Tamura, Hiroyasu Ishida
  • Patent number: 4981936
    Abstract: Water soluble terpolymers based on (1) an acrylamide or acrylamide derivative, (2) a cationic vinyl monomer and (3) a hydrophilic vinyl monomer of the formula CH.sub.2 C(R)C(O)O(CH.sub.2 (CH.sub.2).sub.m O).sub.n E where R and E are each hydrogen or alkyl, m is an integer from 1 to 3 and n is an integer from 1 to 25 are useful flocculants.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: January 1, 1991
    Assignee: Polypure, Inc.
    Inventors: Frederick J. Good, Jr., Ronald E. Highsmith
  • Patent number: 4971424
    Abstract: Novel optical fiber cladding compositions containing fluorinated acrylamide monomers are described. The claddings are liquids at room temperature which possess excellent coating viscosities in the pre-polymerized state and are polymerized by actinic radiation.
    Type: Grant
    Filed: October 26, 1989
    Date of Patent: November 20, 1990
    Assignee: Minnesota Mining and Manufacturing Co.
    Inventors: Stefan A. Babirad, Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
  • Patent number: 4900420
    Abstract: A process for preparing an anion exchange membrane, which comprises subjecting a carboxylate membrane made of a copolymer having repeating units of the formula: ##STR1## wherein X is F or CF.sub.3, l is an integer of from 0 to 5, m is 0 or 1, n is an integer of from 1 to 5, and p/q is from 4 to 16, and R is an alkyl group, to an acid or base treatment, and then introducing anion exchange groups thereinto.
    Type: Grant
    Filed: March 28, 1988
    Date of Patent: February 13, 1990
    Assignee: Tosoh Corporation
    Inventors: Yasuhiro Kurauchi, Toru Seita, Kiyohide Matsui, Kikuo Sugimoto
  • Patent number: 4855376
    Abstract: This invention provides novel sidechain liquid crystalline polymers which exhibit nonlinear response, and which have utility as a transparent nonlinear optical component in optical light switch and light modulator devices.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: August 8, 1989
    Assignee: Hoechst Celanese Corp.
    Inventors: Ronald N. De Martino, Hyun-Nam Yoon, James B. Stamatoff
  • Patent number: 4853448
    Abstract: Copolymers comprising perfluoroalkyl groups, reproduction layers containing these copolymers and use thereof for waterless offset printing. The novel perfluoroalkyl group-containing copolymers are prepared from at least two different monomers, monomer (a) comprising acryloyl or methacryloyl groups and phenolic OH groups and monomer (b) comprising acryloyloxy, methacryloyloxy or vinyl groups and a perfluoroalkyl group. Monomer component (a) can, for example, be prepared from a hydroxybenzoic acid by esterification with a hydroxyalkyl-acrylate. The novel copolymers are, in particular, used as binders in radiation-sensitive reproduction layers which additionally contain at least one radiation-sensitive compound. Reproduction layers of this kind are used as radiation-sensitive coatings of support materials for printing plates used in waterless offset printing.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: August 1, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner H. Muller, Arnold Schneller
  • Patent number: 4806608
    Abstract: Bis-maleimide compounds of the formula: ##STR1## where R' is an alkenylene or alkylene group; the R" groups are independently hydrocarbon or halohydrocarbon groups; and n is an integer, are hydrolytically stable compounds which may be thermally cured, or co-cured with other radically cureable monomers, to provide crosslinked polymer with good thermal properties. Compounds of the formula where n is above about 9 can be used as additives for radically cureable silicone formulations.
    Type: Grant
    Filed: March 16, 1987
    Date of Patent: February 21, 1989
    Assignee: Loctite Corporation
    Inventor: Philip Klemarczyk