Two Six-membered Hetero Rings, Which Each Contain Plural Ring Oxygens, Form The Spiro (e.g., Spirobi-(meta-dioxane), Etc.) Patents (Class 549/335)
  • Patent number: 11214714
    Abstract: The present invention relates to an adhesive comprising a thermoplastic polyacrylated glycerol polymer, water, and a cross linker that is reactive with the polyacrylated glycerol polymer. This adhesive is useful in the formation of cellulosic products including oriented strand board (OSB), particle board, oriented structural straw board, chipboard, plywood, laminated veneer lumber (LVL), pressed wood, glued laminated timber (glulam), cross-laminated timber (CLT), and other wood products. Methods of producing the adhesive and cellulosic products are also disclosed.
    Type: Grant
    Filed: May 7, 2019
    Date of Patent: January 4, 2022
    Assignees: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC., MIDWEST ACRYLATED PROCESSES, LLC
    Inventors: Eric W. Cochran, Nacu B. Hernandez, R. Chris Williams, Michael Forrester, David Grewell, Andrew Becker, Joseph J. Marcinko
  • Patent number: 10370384
    Abstract: The present invention provides a method for producing a diol having a cyclic acetal skeleton, in which the method include an acetalization reaction step of obtaining a diol having a cyclic acetal skeleton by subjecting raw material hydroxypivalaldehyde and at least pentaerythritol and/or trimethylolpropane to an acetalization reaction under an acid catalyst and the raw material hydroxypivalaldehyde can contain a prescribed amount of at least one impurity selected from the group consisting of formaldehyde, neopentyl glycol, an ester compound having a neopentyl glycol skeleton represented by formula (III), and isobutyraldehyde.
    Type: Grant
    Filed: March 9, 2017
    Date of Patent: August 6, 2019
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Masahiro Yamane
  • Patent number: 9023921
    Abstract: A method for inhibiting the crystal growth rate of an amide compound present in a molten polyolefin-based resin and a method for producing a polyolefin-based resin molded article are provided. A phenol compound is incorporated into an amide compound-containing polyolefin-based resin such that a weight ratio, amide compound:phenol compound, is 60:40 to 10:90.
    Type: Grant
    Filed: May 13, 2010
    Date of Patent: May 5, 2015
    Assignee: New Japan Chemical Co., Ltd.
    Inventors: Reira Ikoma, Shohei Iwasaki, Yohei Uchiyama
  • Patent number: 8962721
    Abstract: Described herein are novel acetal compounds capable as nucleating agents for polyolefins. The present invention relates to such compounds synthesized by reacting aromatic aldehydes with polyols and further, to the achievement of high crystallization temperatures in polypropylene compositions upon dispersal therein of formulations containing one or more of the said acetal compounds.
    Type: Grant
    Filed: January 14, 2011
    Date of Patent: February 24, 2015
    Assignee: Reliance Industries Limited
    Inventors: Gandham Satya Srinivasa Rao, S. Muthukumaru Pillai, Virendra Kumar Gupta
  • Publication number: 20140135455
    Abstract: The present disclosure relates to the preparation of ketal compounds from polyols and oxocarboxylates, and uses thereof.
    Type: Application
    Filed: January 20, 2014
    Publication date: May 15, 2014
    Applicant: SEGETIS, INC.
    Inventors: Sergey Selifonov, Adam Edward Goetz, Feng Jing
  • Patent number: 8715710
    Abstract: A semi-solid delivery vehicle contains a polyorthoester and an excipient, and a semi-solid pharmaceutical composition contains an active agent and the delivery vehicle. The pharmaceutical composition may be a topical, syringable, or injectable formulation; and is suitable for local delivery of the active agent. Methods of treatment are also disclosed.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: May 6, 2014
    Assignee: Heron Therapeutics, Inc.
    Inventors: Steven Y. Ng, Hui Rong Shen, Jorge Heller
  • Patent number: 8653223
    Abstract: Ketal compounds of the structure I and a method of preparation of the compound from polyols and oxocarboxylates, as well as uses thereof.
    Type: Grant
    Filed: April 16, 2009
    Date of Patent: February 18, 2014
    Assignee: Segetis, Inc.
    Inventors: Sergey Selifonov, Adam Edward Goetz, Feng Jing
  • Publication number: 20130116366
    Abstract: Described herein are novel acetal compounds capable as nucleating agents for polyolefins. The present invention relates to such compounds synthesized by reacting aromatic aldehydes with polyols and further, to the achievement of high crystallization temperatures in polypropylene compositions upon dispersal therein of formulations containing one or more of the said acetal compounds.
    Type: Application
    Filed: January 14, 2011
    Publication date: May 9, 2013
    Applicant: RELIANCE INDUSTRIES LIMITED
    Inventors: Gandham Satya Srinivasa Rao, S. Muthukumaru Pillai, Virendra Kumar Gupta
  • Publication number: 20120308640
    Abstract: The invention concerns compounds of the formula: X—(Y)t wherein: X is Formula (X), each Y is the same or different and is Formula (Y) —O—[CH2—CH(OH)—CH2—O—]m—H; or —C(OR5)3; R1, R2, R3, R6, R7, R8, R9, R10 are each, independently, —(CH2CH2O)m—R4, —[CH2CH(OH)CH2O]nH, OR11, —O(CH2)PR13, or —(CH2)R12; each R4 is independently OR5 or OH; R5, R11 and R12 are each, independently, H or C1-C30 alkyl; R13 is —NH3+Cl? or —NHBoc; t is an integer from 2 to 6; m, n, and p are each, independently, an integer from 1 to 12; and each q, r, and s is 0 or 1 and the sum of q+r+s is at least 2.
    Type: Application
    Filed: August 5, 2010
    Publication date: December 6, 2012
    Applicant: The Trustees of The University of Pennsylvania
    Inventors: Virgil Percec, Andrew D. Hughes, Pawaret Leowanawat, Daniela A. Wilson, Christopher J. Wilson
  • Patent number: 8252304
    Abstract: A semi-solid delivery vehicle contains a polyorthoester and an excipient, and a semi-solid pharmaceutical composition contains an active agent and the delivery vehicle. The pharmaceutical composition may be a topical, syringable, or injectable formulation; and is suitable for local delivery of the active agent. Methods of treatment are also disclosed.
    Type: Grant
    Filed: September 22, 2009
    Date of Patent: August 28, 2012
    Assignee: A. P. Pharma, Inc.
    Inventors: Steven Y. Ng, Hui Rong Shen, Jorge Heller
  • Patent number: 8252306
    Abstract: A semi-solid delivery vehicle contains a polyorthoester and an excipient, and a semi-solid pharmaceutical composition contains an active agent and the delivery vehicle. The pharmaceutical composition may be a topical, syringable, or injectable formulation; and is suitable for local delivery of the active agent. Methods of treatment are also disclosed.
    Type: Grant
    Filed: October 24, 2011
    Date of Patent: August 28, 2012
    Assignee: A.P. Pharma, Inc.
    Inventors: Steven Y. Ng, Hui Rong Shen, Jorge Heller
  • Patent number: 8252305
    Abstract: A semi-solid delivery vehicle contains a polyorthoester and an excipient, and a semi-solid pharmaceutical composition contains an active agent and the delivery vehicle. The pharmaceutical composition may be a topical, syringable, or injectable formulation; and is suitable for local delivery of the active agent. Methods of treatment are also disclosed.
    Type: Grant
    Filed: October 24, 2011
    Date of Patent: August 28, 2012
    Assignee: A.P. Pharma
    Inventors: Steven Y. Ng, Hui Rong Shen, Jorge Heller
  • Patent number: 8232416
    Abstract: A method of manufacturing a compound represented by formula (2) is provided, the method including thermally decomposing a compound represented by formula (1) under a reduced pressure: wherein Rf1 and Rf2 each independently represents a fluorine atom or a perfluorinated monovalent substituent, Rf3 and Rf4 each independently represents a fluorine atom, a perfluorinated monovalent substituent or a perfluorinated divalent substituent, Rf3 and Rf4 may combine with each other to form a ring, each of Rf3 and Rf4 may combine with Rf5 to form a ring, and Rf5 represents a perfluorinated (n+1)-valent to (2n+2)-valent linkage group, provided that n represents an integer of 1 to 5.
    Type: Grant
    Filed: February 25, 2009
    Date of Patent: July 31, 2012
    Assignee: FUJIFILM Corporation
    Inventors: Hiroki Sugiura, Masayuki Harada
  • Publication number: 20120157519
    Abstract: Tellurium-containing compounds identified for use in a method of treating, or prophylaxis against, a viral infection caused by an influenza virus, uses thereof and pharmaceutical kits and pharmaceutical corn positions comprising the same, are disclosed. The tellurium-containing compounds disclosed herein are suitable for co-administration with an antiviral agent.
    Type: Application
    Filed: June 16, 2010
    Publication date: June 21, 2012
    Applicant: Biomas Ltd.
    Inventors: Benjamin Sredni, Michael Albeck
  • Publication number: 20120035304
    Abstract: A method for inhibiting the crystal growth rate of an amide compound present in a molten polyolefin-based resin and a method for producing a polyolefin-based resin molded article are provided. A phenol compound is incorporated into an amide compound-containing polyolefin-based resin such that a weight ratio, amide compound:phenol compound, is 60:40 to 10:90.
    Type: Application
    Filed: May 13, 2010
    Publication date: February 9, 2012
    Applicant: NEW JAPAN CHEMICAL CO., LTD.
    Inventors: Reira Ikoma, Shohei Iwasaki, Yohei Uchiyama
  • Patent number: 8007938
    Abstract: A non-aqueous electrolyte solution is provided that realizes a large capacity, exhibits high storage characteristics and cycle characteristics, and is capable of inhibiting gas generation.
    Type: Grant
    Filed: April 19, 2005
    Date of Patent: August 30, 2011
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Minoru Kotato, Asao Kominato
  • Publication number: 20110184193
    Abstract: In the production of spiroglycol by the reaction of pentaerythritol and hydroxypivalaldehyde in water in the presence of an acid catalyst, (A) a total content of amines and amine salts in hydroxypivalaldehyde is reduced to 1.5% by weight or lower; (B) seed crystals are added to the reaction system before initiating the reaction and/or during the reaction in an amount from 1.5 to 30% by weight on the basis of the total feed amount of pentaerythritol, hydroxypivalaldehyde, water, the acid catalyst and the seed crystals, each being fed into the reaction system; (C) the pH of the reaction system is kept from 0.1 to 4.
    Type: Application
    Filed: April 6, 2011
    Publication date: July 28, 2011
    Inventors: Masafumi WATANABE, Junichi AMEMIYA, Ikutaro KUZUHARA
  • Publication number: 20110082264
    Abstract: The present disclosure relates to the preparation of ketal compounds from polyols and oxocarboxylates, and uses thereof.
    Type: Application
    Filed: April 16, 2009
    Publication date: April 7, 2011
    Applicant: SEGETIS, INC.
    Inventors: Sergey Selifonov, Adam Edward Goetz, Feng Jing
  • Patent number: 7919637
    Abstract: A fluorine-containing spiroacetal compound represented by the following formula (A): wherein X represents >C(CF3)(Y) or >C?CF2, in which Y represents —CF2OCOR1, —COOR2, —COF, or —CH2OR3, R1 represents an alkyl or cycloalkyl group having at least one fluorine atom, R2 represents a hydrogen atom, an alkali metal, an alkaline earth metal, an alkyl group, or a cycloalkyl group and R3 represents a hydrogen atom or an acyl group; wherein the alkyl or cycloalkyl group for R1 may have a substituent other than fluorine atom; the alkyl or cycloalkyl group for R2 may have a substituent; and the acyl group for R3 may have a substituent.
    Type: Grant
    Filed: October 10, 2006
    Date of Patent: April 5, 2011
    Assignee: Fujifilm Corporation
    Inventors: Takayuki Ito, Toshimitsu Sakuma
  • Publication number: 20110021658
    Abstract: The invention relates to polyketal compounds. The compounds are synthesized by the selective ketalization of oxocarboxylic acids, e.g. keto acids and semialdehydes, and esters thereof with tetrols and higher polyols that products two or more cyclic ketal ester moieties per molecule, wherein the cyclic ketal moieties are situated in a bis-, tris-, or polyketal conformation. The invention further relates to applications of these compounds and subsequent reactions thereof.
    Type: Application
    Filed: October 9, 2008
    Publication date: January 27, 2011
    Applicant: SEGETIS, INC.
    Inventors: Sergey Selifonov, Scott David Rothstein, Douglas Alan Wicks, Brian Daniel Mullen, Tara Jane Mullen, Jason Douglass Pratt, Charles Todd Williams, Chunyong (Kevin) Wu, Ning Zhou
  • Patent number: 7605276
    Abstract: A method of producing a spirocyclic acetal compound of formula (II), having subjecting a compound of formula (I) and pentaerythritol to dehydration condensation, in the presence of a solid acid catalyst; and the polymer having a repeating unit represented by formula (III), which is produced using the spirocyclic acetal compound of formula (II): wherein R1 represents an alkyl, cycloalkyl or aryl group, Q represents a hydrogen atom or an acyl group, L represents a divalent linking group having at least one carbon atom, and n is 0 or 1.
    Type: Grant
    Filed: February 1, 2007
    Date of Patent: October 20, 2009
    Assignee: Fujifilm Corporation
    Inventors: Takayuki Ito, Sumiaki Yamasaki, Toshimitsu Sakuma
  • Publication number: 20090233952
    Abstract: [Object] To provide a substituted cycloalkene derivative having an action to suppress intracellular signal transduction or cell activation induced by endotoxin and to suppress cell responses due to the intracellular signal transduction and cell activation such as an excess generation of inflammatory mediators such as TNF-?, pharmacologically acceptable salts therefor, a medicament containing them as an active ingredient, a preparation method therefor, and a medicament containing the aforementioned substituted cycloalkene derivative as an active ingredient which is superior in prophylaxis and/or treatment of diseases such as sepsis (septic shock, disseminated intravascular coagulation, multiple organ failure and the like), that are associated with intracellular signal transduction or cell activation induced by endotoxin and to cell responses to the intracellular signal transduction and cell activation.
    Type: Application
    Filed: September 13, 2006
    Publication date: September 17, 2009
    Inventors: Tomio Kimura, Nobuyuki Ohkawa, Takayoshi Nagasaki, Atsuhiro Sugidachi, Osamu Ando
  • Publication number: 20090216030
    Abstract: A method of manufacturing a compound represented by formula (2) is provided, the method including thermally decomposing a compound represented by formula (1) under a reduced pressure: wherein Rf1 and Rf2 each independently represents a fluorine atom or a perfluorinated monovalent substituent, Rf3 and Rf4 each independently represents a fluorine atom, a perfluorinated monovalent substituent or a perfluorinated divalent substituent, Rf3 and Rf4 may combine with each other to form a ring, each of Rf3 and Rf4 may combine with Rf5 to form a ring, and Rf5 represents a perfluorinated (n+1)-valent to (2n+2)-valent linkage group, provided that n represents an integer of 1 to 5.
    Type: Application
    Filed: February 25, 2009
    Publication date: August 27, 2009
    Applicant: FUJIFILM Corporation
    Inventors: Hiroki SUGIURA, Masayuki Harada
  • Publication number: 20090149664
    Abstract: A fluorine-containing spiroacetal compound represented by the following formula (A): wherein X represents >C(CF3)(Y) or >C?CF2, in which Y represents —CF2OCOR1, —COOR2, —COF, or —CH2OR3, R1 represents an alkyl or cycloalkyl group having at least one fluorine atom, R2represents a hydrogen atom, an alkali metal, an alkaline earth metal, an alkyl group, or a cycloalkyl group and R3 represents a hydrogen atom or an acyl group; wherein the alkyl or cycloalkyl group for R1 may have a substituent other than fluorine atom; the alkyl or cycloalkyl group for R2 may have a substituent; and the acyl group for R3 may have a substituent.
    Type: Application
    Filed: October 10, 2006
    Publication date: June 11, 2009
    Inventors: Takayuki Ito, Toshimitsu Sakuma
  • Publication number: 20090018350
    Abstract: A fluorine-containing ether compound with a fluorine content increased, the fluorine content being enhanced by fluorinating a polymer including a repeating unit represented by the following Formula (I): wherein Rh1 represents a divalent linkage group; Rf2 represents an perfluoroalkylene group; each of Rf3 and Rf4 independently represents a fluorine atom, a perfluoroalkyl group or a perfluoroalkoxy group, and any two of Rf2, Rf3 and Rf4 may be combined with each other to form a ring.
    Type: Application
    Filed: April 9, 2008
    Publication date: January 15, 2009
    Applicant: FUJIFILM Corporation
    Inventors: Takayuki ITO, Toshimitsu Sakuma
  • Patent number: 7232852
    Abstract: A visible light cationically photopolymerizable composition is provided. This composition includes an expanding monomer and a dioxirane. More specifically, the expanding monomer used in this composition is one or more dioxiranyl tetraoxaspiro[5.5]undecanes. The composition of the present invention may be used as a matrix resin for dental restorative materials. Another embodiment of the present invention is various novel dioxiranyl tetraoxaspiro[5.5]undecanes.
    Type: Grant
    Filed: February 20, 2004
    Date of Patent: June 19, 2007
    Assignee: Curators of the University of Missouri
    Inventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, Andrew J. Holder, Shin-Shi Chen, Li Jeang
  • Patent number: 6825364
    Abstract: A visible light cationically photopolymerizable composition is provided. This composition includes an expanding monomer and a dioxirane. More specifically, the expanding monomer used in this composition is one or more dioxiranyl tetraoxaspiro[5.5]undecanes. The composition of the present invention may be used as a matrix resin for dental restorative materials. Another embodiment of the present invention is various novel dioxiranyl tetraoxaspiro[5.5]undecanes.
    Type: Grant
    Filed: March 5, 2002
    Date of Patent: November 30, 2004
    Assignee: Curators of the University of Missouri
    Inventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, Andrew J. Holder, Shin-Shi Chen, Li Jeang
  • Patent number: 6653486
    Abstract: Photopolymerizable compositions are provided which are the reaction products of a vinyl ether, a photoinitiator system comprising an iodonium salt, a visible light sensitizer, and an electron donor compound. These monomeric/oligomeric compositions may also include epoxides, polyols, spiroorthocarbonates. One embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, a spiroorthocarbonate, and a photoinitiator system. Another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, and a photoinitiator system. Still another embodiment of the present invention is a polymerizable composition comprised of a vinyl ether, an epoxide, a polyol, a spiroorthocarbonate, and a photoinitiator system. Still further, another embodiment of the present invention is certain novel spiroorthocarbonate compounds. Each of these novel spiroorthocarbonate compounds include at least one epoxy group as a substituent.
    Type: Grant
    Filed: September 4, 2002
    Date of Patent: November 25, 2003
    Assignee: Curators of the University of Missouri
    Inventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick
  • Patent number: 6545166
    Abstract: In this application is disclosed a process for producing 3,9-bis(2-chloroethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane comprising a step of reacting acrolein, pentaerythritol, and hydrogen chloride at one step, according to which the compound can be obtained conveniently in high yields.
    Type: Grant
    Filed: June 26, 2002
    Date of Patent: April 8, 2003
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masao Honma, Atsushi Mashita, Hiroyasu Koto
  • Patent number: 5939453
    Abstract: PEG-POE, PEG-POE-PEG, and POE-PEG-POE block copolymers have both hydrophilic and hydrophobic blocks. They form micelles in aqueous solution, making them suitable for encapsulation or solubilization of hydrophobic or water-insoluble materials; and they also form bioerodible matrices for the sustained release of active agents, especially when the POE block(s) contain at least one unit containing an .alpha.-hydroxy acid.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: August 17, 1999
    Assignee: Advanced Polymer Systems, Inc.
    Inventors: Jorge Heller, Steven Y. Ng
  • Patent number: 5808108
    Abstract: Polymeric compositions are provided which are the reaction product of spiroorthocarbonates and epoxy resins and undergo reduced bulk polymerization shrinkage. The spiroorthocarbonates are of the general formula: ##STR1## wherein X=O or S;R.sub.1, and R.sub.2 are independently selected from the group consisting of H, alkyl, aryl, substituted alkyl, and substituted aryl;R.sub.3 and R.sub.4 =--(CH.sub.2).sub.n --O--R.sub.5 ;n=1 or 2;R.sub.5 =alkyl, aryl, substituted aryl, substituted alkyl, ##STR2## R.sub.6 =H, alkyl, aryl, substituted alkyl, or substituted aryl; and R.sub.7 =alkyl, aryl, substituted alkyl, or substituted aryl.
    Type: Grant
    Filed: January 15, 1997
    Date of Patent: September 15, 1998
    Inventors: Cecil C. Chappelow, J. David Eick, Charles S. Pinzino
  • Patent number: 5620831
    Abstract: Disclosed are novel cyanoguanidine derivatives which are usable as an epoxy resin curing agent and are represented by the following general formula (1). A thermosetting resin composition and a photocurable and thermosetting resin composition containing the following cyanoguanidine derivatives and other derivatives as the epoxy resin curing agent are also disclosed. ##STR1## wherein R.sup.1 represents a substituent selected from the group consisting of the following substituents (a) through (k).
    Type: Grant
    Filed: March 28, 1995
    Date of Patent: April 15, 1997
    Assignee: Taiyo Ink Manufacturing Co., Ltd.
    Inventor: Osamu Kawana
  • Patent number: 5338869
    Abstract: A hydroxyphenylpropionic ester represented by the formula of ##STR1## which has a crystal structure showing a sharp X-ray diffraction peak at a diffraction angle 2.theta.=7.9.degree. by X-ray diffraction measurement using an X-ray of a Cu-K.sub..alpha. wavelength. This novel crystal exhibits largely advantageous effects in industrial production and usage of the ester because of its high purity, high quality, excellent filterability owing to the large crystal growth, and excellent fluidity owing to the large bulk specific gravity.
    Type: Grant
    Filed: July 9, 1993
    Date of Patent: August 16, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kikumitsu Inoue, Manji Sasaki, Shinichi Yachigo
  • Patent number: 5260439
    Abstract: The present invention relates to a high surface hardness transparent resin having excellent scratch resistance, heat resistance and chemical resistance, a glazing material, a protective cover for display devices, an optical lens and a hard coat material comprising the aforesaid resin, and a novel polymerizable monomer which is useful as a raw material of the above-mentioned resin.The monomer is represented by the formula (I) ##STR1## (wherein R is an aliphatic residue having or not having an halogen atom, an oxygen atom, an alicyclic ring, a heterocyclic ring or an aromatic ring, an alicyclic residue, or a heterocyclic residue, n is an integer of 1 to 4, when n=1, X is oxygen or sulfur, when n.gtoreq.2, X's are all oxygen or all sulfur, one X is oxygen while the other X or X's are sulfur, one X is sulfur while the other X or X's are oxygen, or two X's are oxygen while the other X's are sulfur).
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: November 9, 1993
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Toshiyuki Suzuki, Katsuyoshi Sasagawa, Masao Imai, Yoshinobu Kanemura
  • Patent number: 5157132
    Abstract: A process and apparatus is disclosed for separation of fatty acid alkyl esters, carotenoids and tocotrienols from oil. Fatty acids in a vegetable oil are subjected to alcoholic esterification to form an ester-rich layer including fatty acid alkyl esters, carotenoids and tocotrienols. The ester-rich layer is exposed to solvolytic micellization to form a carotenoid-rich layer. The ester-rich layer is separated from the carotenoid-rich layer. The carotenoids in the carotenoid-rich layer are concentrated and can be adsorptively separated from the carotenoid-rich layer. Fatty acid alkyl esters are separated from the ester-rich layer to form a tocotrienol-rich layer. Individual tocotrienols in the tocotrienol-rich layer are adsorptively separated and concentrated.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: October 20, 1992
    Assignee: Carotech Associates
    Inventors: Barrie Tan, Mohammed H. Saleh
  • Patent number: 4950771
    Abstract: This invention provides 3,9-bis[1,1-dimethyl-2-(4'-hydroxybenzoyloxy)ethyl]-2,4,8,10-tetraoxaspiro [5,5]-undecane represented by the formula: ##STR1## a process for preparing the above compound by a transesterification reaction of 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,10-tetraoxaspiro[5,5]undecane with alkyl 4-hydroxybenzoate.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: August 21, 1990
    Assignees: Mitsubishi Gas Chemical Company, Inc., Arakawa Chemical Industries, Ltd.
    Inventors: Mitsuhito Masumoto, Toshiaki Asoh, Youichirou Ezaki, Hiroshi Aibe
  • Patent number: 4891436
    Abstract: A process for the manufacture of bis-methylene spiro-orthocarbonate (BMSOC) wherein methyallyl chloride is subjected to the action of chlorine gas to form a mixture of 1,1-dichloromethyl ethylene and other chlorinated hydrocarbons which need not be and are not separated. The mixture is merely treated wich an alkali metal acetate such as sodium acetate to yield an easily separable second mixture by fractional distillation. The desired 1,1-diacetoxymethyl ethylene is thus recovered in high yield. It is then converted by transesterification in over 90% yield to the bismethylene spiroorthocarbonate (BMSOC). BMSOC is useful as a component for coatings composites, adhesive formulations and the like, which have the unique ability to (a) cure by free radical initiation and (b) expand during cure. BMSOC may be used as a component for dental composites, i.e. filling materials, because it reduces the possibility of leakage at the margin, i.e. at the composite-enamel interface and as a component in bone cements.
    Type: Grant
    Filed: November 21, 1988
    Date of Patent: January 2, 1990
    Assignee: Epolin, Inc.
    Inventors: Murray S. Cohen, Morris Dunkel
  • Patent number: 4851551
    Abstract: An ultraviolet ray absorbing agent comprising as an active ingredient a spiro compound having a spiro ring structure in the molecule, said spiro compound being represented by the general formula ##STR1## wherein, Y is ##STR2## A is ##STR3## R.sub.1 is hydrogen, halogen, lower alkyl of 1 to 4 carbon atoms, lower alkoxyl of 1 to 4 carbon atoms, carboxyl, or sulfo, R.sub.2 is hydrogen or alkyl of 1 to 12 carbon atoms, R.sub.3 and R.sub.4 are alkyls of 1 to 12 carbon atoms, X is methylene, oxygen, imino, sulfur, sulfinyl, or sulfonyl, and n is an integer of 1 to 12.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: July 25, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuo Kaneoya, Haruki Okamura
  • Patent number: 4851550
    Abstract: The process according to the invention is particularly suitable for the preparation of aliphatic spiroorthocarbonates. For the preparation of aliphatic spiroorthocarbonates of the formula ##STR1## in which dichloromethane derivatives of the formula(R.sup.5 O).sub.2 CCl.sub.2 (II)are reacted with aliphatic diols of the formulaHO--B--OH (V)in the presence of stoichiometric amounts of H-containing bases, which contain the nitrogen as part of an aromatic system.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: July 25, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Mues, Hans-Josef Buysch
  • Patent number: 4845244
    Abstract: 3,9-bis{2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy]-1,1-dimethylethyl}-2,4,8,10-tetraoxaspiro[5.5] undecane having a novel crystalline structure which, when subjected to Cu-K.sub..alpha. X-ray diffraction, shows sharp X-ray diffraction peaks at angles of diffraction, 2.theta.=4.2.degree. and 2.theta.=10.6.degree.. Also provided is a method for producing this compound, using a certain recrystallization solvent.
    Type: Grant
    Filed: April 28, 1988
    Date of Patent: July 4, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Manji Sasaki, Chinehito Ebina, Haruki Okamura, Shinichi Yachigo, Tamaki Ishii
  • Patent number: 4822522
    Abstract: Hindered phenol amides are provided having the following formula: ##STR1## wherein: R.sub.1 and R.sub.2 are hydrogen or lower alkyl having from one to four carbon atoms;m.sub.1 and m.sub.2 are 0 or 1; andn.sub.1 and n.sub.2 are selected from 1, 2 and 3; as well as stabilizer compositions for synthetic polymers and synthetic polymer compositions containing such hindered phenol amides.
    Type: Grant
    Filed: August 26, 1987
    Date of Patent: April 18, 1989
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Kenji Tajima, Takao Nishina, Kazunori Nishikawa
  • Patent number: 4769479
    Abstract: 3,9-bis{2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy]-1,1-dimethylethyl}-2,4,8,10-tetraoxaspiro[5.5] undecane having a novel crystalline structure which, when subjected to Cu-K.sub..alpha. X-ray diffraction, shows sharp X-ray diffraction peaks at angles of diffraction, 2.theta.=4.2.degree. and 2.theta.=10.6.degree.. Also provided is a method for producing this compound.
    Type: Grant
    Filed: May 30, 1986
    Date of Patent: September 6, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Manji Sasaki, Chinehito Ebina, Haruki Okamura, Shinichi Yachigo, Tamaki Ishii
  • Patent number: 4754045
    Abstract: Method for producing 3,9-bis{2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dime thylethyl}-2,4,8,10-tetraoxaspiro[5.5]undecane by ester exchange of a 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)-propionic acid ester with 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane at a temperature of 170.degree.-250.degree. C. using a calcium compound as a catalyst in an amount of 0.05-1.5 moles per mole of the 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]-undecane.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: June 28, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Manji Sasaki, Chinehito Ebina, Haruki Okamura, Shinichi Yachigo, Tamaki Ishii
  • Patent number: 4745195
    Abstract: An ultraviolet ray absorbing agent comprising as an active ingredient a spiro compound having a spiro ring structure in the molecule, said spiro compound being represented by the general formula ##STR1## wherein, Y is ##STR2## A is ##STR3## R.sub.1 is hydrogen, halogen, lower alkyl of 1 to 4 carbon atoms, lower alkoxyl of 1 to 4 carbon atoms, carboxyl, or sulfo, R.sub.2 is hydrogen or alkyl of 1 to 12 carbon atoms, R.sub.3 and R.sub.4 are alkyls of 1 to 12 carbon atoms, X is methylene, oxygen, imino, sulfur, sulfinyl, or sulfonyl, and n is an integer of 1 to 12.
    Type: Grant
    Filed: April 28, 1986
    Date of Patent: May 17, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuo Kaneoya, Haruki Okamura
  • Patent number: 4739080
    Abstract: Method for the purification of 3,9-bis{2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dime thylethyl} -2,4,8,10-tetraoxaspiro[5.5]undecane, to form crystals having a crystalline structure which, when subjected to Cu-K.sub..alpha. X-ray diffraction, show sharp X-ray diffraction peaks at angles of diffraction, to 2.theta.=2.8.degree., 2.theta.=8.7.degree. and 2.theta.=11.7.degree., by recrystallizing the ester at a temperature lower than 40.degree. C. using as a recrystallization solvent, A C.sub.5 -C.sub.10 alicyclic hydrocarbon, which may contain a limited amount of certain other solvents, or using a mixed solvent of a C.sub.5 -C.sub.10 aliphatic hydrocarbon and at least one other certain solvent in a certain weight ratio.
    Type: Grant
    Filed: May 30, 1986
    Date of Patent: April 19, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Manji Sasaki, Chinehito Ebina, Haruki Okamura, Shinichi Yachigo, Tamaki Ishii
  • Patent number: 4656294
    Abstract: A process for producing a polyglycidyl ether which comprises reacting a mixture of 4-oxy-3-methoxybenzaldehyde and 4-oxybenzaldehyde in the molar ratio of 5/95 to 95/5 with pentaerythritol to give a bisphenol having a spiroacetal ring, and further reacting the bisphenol with epihalohydrin or .beta.-methylepihalohydrin is disclosed. The polyglycidyl ether obtained has excellent solubility in solvents, and the cured product obtained therefrom has excellent elongation, modulus of elasticity, impact resistance, and heat resistance.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: April 7, 1987
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventor: Kaoru Kanayama
  • Patent number: 4587352
    Abstract: A novel urethane (meth)acrylate compound represented by a general formula shown below.
    Type: Grant
    Filed: June 19, 1985
    Date of Patent: May 6, 1986
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Yoshiji Masaoka, Motonobu Kubo
  • Patent number: 4532335
    Abstract: Allyl acetals and substituted allyl acetals are rearranged to produce ketene acetals by heating the acetals in a solution of an alkali metal alkoxide in an ethylene amine.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: July 30, 1985
    Assignee: SRI International
    Inventor: Robert F. Helwing
  • Patent number: 4528386
    Abstract: Pentaerythritol can be converted to its diformal, 2,4,8,10-tetroxaspiro[5.5]undecane, by heating it to a temperature within the range of about 110.degree. to 150.degree. C. for a period of up to 10 minutes, in the presence of a slight excess of paraformaldehyde and of a catalytic quantity of an acid catalyst such as sulfuric acid. The reaction may be carried out in two steps, by forming first the monoformal, then the diformal. In any case, total reaction time is about 10 minutes and yield of diformal are greater than 90%.Previous processes require hours or days, and often, tedious operating procedures.
    Type: Grant
    Filed: September 3, 1980
    Date of Patent: July 9, 1985
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Algirdas C. Poshkus
  • Patent number: 4513143
    Abstract: Rearrangement of allyl acetals to ketene acetals is disclosed. The rearrangement is accomplished by mixing the allyl acetal with a solution of an alkali metal lower alkyl in a water-soluble primary amine. After several hours contact with the allyl acetal with the solution ketene acetal formed during the contact is separated from the reaction mixture.
    Type: Grant
    Filed: December 1, 1982
    Date of Patent: April 23, 1985
    Assignee: SRI International
    Inventors: Steven Y. Ng, Donald W. Penhale, Jorge Heller