Two Six-membered Hetero Rings, Which Each Contain Plural Ring Oxygens, Form The Spiro (e.g., Spirobi-(meta-dioxane), Etc.) Patents (Class 549/335)
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Patent number: 11214714Abstract: 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: GrantFiled: May 7, 2019Date of Patent: January 4, 2022Assignees: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC., MIDWEST ACRYLATED PROCESSES, LLCInventors: Eric W. Cochran, Nacu B. Hernandez, R. Chris Williams, Michael Forrester, David Grewell, Andrew Becker, Joseph J. Marcinko
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Patent number: 10370384Abstract: 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: GrantFiled: March 9, 2017Date of Patent: August 6, 2019Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Masahiro Yamane
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Patent number: 9023921Abstract: 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: GrantFiled: May 13, 2010Date of Patent: May 5, 2015Assignee: New Japan Chemical Co., Ltd.Inventors: Reira Ikoma, Shohei Iwasaki, Yohei Uchiyama
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Patent number: 8962721Abstract: 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: GrantFiled: January 14, 2011Date of Patent: February 24, 2015Assignee: Reliance Industries LimitedInventors: Gandham Satya Srinivasa Rao, S. Muthukumaru Pillai, Virendra Kumar Gupta
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Publication number: 20140135455Abstract: The present disclosure relates to the preparation of ketal compounds from polyols and oxocarboxylates, and uses thereof.Type: ApplicationFiled: January 20, 2014Publication date: May 15, 2014Applicant: SEGETIS, INC.Inventors: Sergey Selifonov, Adam Edward Goetz, Feng Jing
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Patent number: 8715710Abstract: 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: GrantFiled: July 18, 2012Date of Patent: May 6, 2014Assignee: Heron Therapeutics, Inc.Inventors: Steven Y. Ng, Hui Rong Shen, Jorge Heller
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Patent number: 8653223Abstract: Ketal compounds of the structure I and a method of preparation of the compound from polyols and oxocarboxylates, as well as uses thereof.Type: GrantFiled: April 16, 2009Date of Patent: February 18, 2014Assignee: Segetis, Inc.Inventors: Sergey Selifonov, Adam Edward Goetz, Feng Jing
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Publication number: 20130116366Abstract: 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: ApplicationFiled: January 14, 2011Publication date: May 9, 2013Applicant: RELIANCE INDUSTRIES LIMITEDInventors: Gandham Satya Srinivasa Rao, S. Muthukumaru Pillai, Virendra Kumar Gupta
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Publication number: 20120308640Abstract: 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: ApplicationFiled: August 5, 2010Publication date: December 6, 2012Applicant: The Trustees of The University of PennsylvaniaInventors: Virgil Percec, Andrew D. Hughes, Pawaret Leowanawat, Daniela A. Wilson, Christopher J. Wilson
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Patent number: 8252304Abstract: 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: GrantFiled: September 22, 2009Date of Patent: August 28, 2012Assignee: A. P. Pharma, Inc.Inventors: Steven Y. Ng, Hui Rong Shen, Jorge Heller
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Patent number: 8252306Abstract: 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: GrantFiled: October 24, 2011Date of Patent: August 28, 2012Assignee: A.P. Pharma, Inc.Inventors: Steven Y. Ng, Hui Rong Shen, Jorge Heller
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Patent number: 8252305Abstract: 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: GrantFiled: October 24, 2011Date of Patent: August 28, 2012Assignee: A.P. PharmaInventors: Steven Y. Ng, Hui Rong Shen, Jorge Heller
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Patent number: 8232416Abstract: 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: GrantFiled: February 25, 2009Date of Patent: July 31, 2012Assignee: FUJIFILM CorporationInventors: Hiroki Sugiura, Masayuki Harada
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Publication number: 20120157519Abstract: 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: ApplicationFiled: June 16, 2010Publication date: June 21, 2012Applicant: Biomas Ltd.Inventors: Benjamin Sredni, Michael Albeck
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Publication number: 20120035304Abstract: 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: ApplicationFiled: May 13, 2010Publication date: February 9, 2012Applicant: NEW JAPAN CHEMICAL CO., LTD.Inventors: Reira Ikoma, Shohei Iwasaki, Yohei Uchiyama
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Patent number: 8007938Abstract: 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: GrantFiled: April 19, 2005Date of Patent: August 30, 2011Assignee: Mitsubishi Chemical CorporationInventors: Minoru Kotato, Asao Kominato
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Publication number: 20110184193Abstract: 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: ApplicationFiled: April 6, 2011Publication date: July 28, 2011Inventors: Masafumi WATANABE, Junichi AMEMIYA, Ikutaro KUZUHARA
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Publication number: 20110082264Abstract: The present disclosure relates to the preparation of ketal compounds from polyols and oxocarboxylates, and uses thereof.Type: ApplicationFiled: April 16, 2009Publication date: April 7, 2011Applicant: SEGETIS, INC.Inventors: Sergey Selifonov, Adam Edward Goetz, Feng Jing
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Patent number: 7919637Abstract: 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: GrantFiled: October 10, 2006Date of Patent: April 5, 2011Assignee: Fujifilm CorporationInventors: Takayuki Ito, Toshimitsu Sakuma
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Publication number: 20110021658Abstract: 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: ApplicationFiled: October 9, 2008Publication date: January 27, 2011Applicant: 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
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Patent number: 7605276Abstract: 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: GrantFiled: February 1, 2007Date of Patent: October 20, 2009Assignee: Fujifilm CorporationInventors: Takayuki Ito, Sumiaki Yamasaki, Toshimitsu Sakuma
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Publication number: 20090233952Abstract: [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: ApplicationFiled: September 13, 2006Publication date: September 17, 2009Inventors: Tomio Kimura, Nobuyuki Ohkawa, Takayoshi Nagasaki, Atsuhiro Sugidachi, Osamu Ando
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Publication number: 20090216030Abstract: 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: ApplicationFiled: February 25, 2009Publication date: August 27, 2009Applicant: FUJIFILM CorporationInventors: Hiroki SUGIURA, Masayuki Harada
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Publication number: 20090149664Abstract: 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: ApplicationFiled: October 10, 2006Publication date: June 11, 2009Inventors: Takayuki Ito, Toshimitsu Sakuma
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Publication number: 20090018350Abstract: 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: ApplicationFiled: April 9, 2008Publication date: January 15, 2009Applicant: FUJIFILM CorporationInventors: Takayuki ITO, Toshimitsu Sakuma
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Patent number: 7232852Abstract: 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: GrantFiled: February 20, 2004Date of Patent: June 19, 2007Assignee: Curators of the University of MissouriInventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, Andrew J. Holder, Shin-Shi Chen, Li Jeang
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Patent number: 6825364Abstract: 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: GrantFiled: March 5, 2002Date of Patent: November 30, 2004Assignee: Curators of the University of MissouriInventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick, Andrew J. Holder, Shin-Shi Chen, Li Jeang
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Patent number: 6653486Abstract: 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: GrantFiled: September 4, 2002Date of Patent: November 25, 2003Assignee: Curators of the University of MissouriInventors: Cecil C. Chappelow, Charles S. Pinzino, J. David Eick
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Patent number: 6545166Abstract: 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: GrantFiled: June 26, 2002Date of Patent: April 8, 2003Assignee: Ajinomoto Co., Inc.Inventors: Masao Honma, Atsushi Mashita, Hiroyasu Koto
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Patent number: 5939453Abstract: 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: GrantFiled: June 4, 1998Date of Patent: August 17, 1999Assignee: Advanced Polymer Systems, Inc.Inventors: Jorge Heller, Steven Y. Ng
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Patent number: 5808108Abstract: 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: GrantFiled: January 15, 1997Date of Patent: September 15, 1998Inventors: Cecil C. Chappelow, J. David Eick, Charles S. Pinzino
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Patent number: 5620831Abstract: 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: GrantFiled: March 28, 1995Date of Patent: April 15, 1997Assignee: Taiyo Ink Manufacturing Co., Ltd.Inventor: Osamu Kawana
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Patent number: 5338869Abstract: 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: GrantFiled: July 9, 1993Date of Patent: August 16, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Kikumitsu Inoue, Manji Sasaki, Shinichi Yachigo
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Patent number: 5260439Abstract: 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: GrantFiled: December 16, 1991Date of Patent: November 9, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Toshiyuki Suzuki, Katsuyoshi Sasagawa, Masao Imai, Yoshinobu Kanemura
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Patent number: 5157132Abstract: 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: GrantFiled: May 18, 1990Date of Patent: October 20, 1992Assignee: Carotech AssociatesInventors: Barrie Tan, Mohammed H. Saleh
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Patent number: 4950771Abstract: 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: GrantFiled: May 19, 1989Date of Patent: August 21, 1990Assignees: Mitsubishi Gas Chemical Company, Inc., Arakawa Chemical Industries, Ltd.Inventors: Mitsuhito Masumoto, Toshiaki Asoh, Youichirou Ezaki, Hiroshi Aibe
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Patent number: 4891436Abstract: 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: GrantFiled: November 21, 1988Date of Patent: January 2, 1990Assignee: Epolin, Inc.Inventors: Murray S. Cohen, Morris Dunkel
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Patent number: 4851551Abstract: 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: GrantFiled: February 16, 1988Date of Patent: July 25, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuo Kaneoya, Haruki Okamura
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Process for the preparation of cyclic aliphatic orthocarbonic esters new cyclic orthocarbonic esters
Patent number: 4851550Abstract: 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: GrantFiled: September 21, 1987Date of Patent: July 25, 1989Assignee: Bayer AktiengesellschaftInventors: Peter Mues, Hans-Josef Buysch -
Patent number: 4845244Abstract: 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: GrantFiled: April 28, 1988Date of Patent: July 4, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Manji Sasaki, Chinehito Ebina, Haruki Okamura, Shinichi Yachigo, Tamaki Ishii
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Patent number: 4822522Abstract: 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: GrantFiled: August 26, 1987Date of Patent: April 18, 1989Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Kenji Tajima, Takao Nishina, Kazunori Nishikawa
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Patent number: 4769479Abstract: 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: GrantFiled: May 30, 1986Date of Patent: September 6, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Manji Sasaki, Chinehito Ebina, Haruki Okamura, Shinichi Yachigo, Tamaki Ishii
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Patent number: 4754045Abstract: 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: GrantFiled: May 29, 1986Date of Patent: June 28, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Manji Sasaki, Chinehito Ebina, Haruki Okamura, Shinichi Yachigo, Tamaki Ishii
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Patent number: 4745195Abstract: 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: GrantFiled: April 28, 1986Date of Patent: May 17, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuo Kaneoya, Haruki Okamura
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Patent number: 4739080Abstract: 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: GrantFiled: May 30, 1986Date of Patent: April 19, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Manji Sasaki, Chinehito Ebina, Haruki Okamura, Shinichi Yachigo, Tamaki Ishii
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Patent number: 4656294Abstract: 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: GrantFiled: July 13, 1984Date of Patent: April 7, 1987Assignee: Mitsubishi Petrochemical Co., Ltd.Inventor: Kaoru Kanayama
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Patent number: 4587352Abstract: A novel urethane (meth)acrylate compound represented by a general formula shown below.Type: GrantFiled: June 19, 1985Date of Patent: May 6, 1986Assignee: Sanyo-Kokusaku Pulp Co., Ltd.Inventors: Yoshiji Masaoka, Motonobu Kubo
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Patent number: 4532335Abstract: 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: GrantFiled: March 7, 1983Date of Patent: July 30, 1985Assignee: SRI InternationalInventor: Robert F. Helwing
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Patent number: 4528386Abstract: 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: GrantFiled: September 3, 1980Date of Patent: July 9, 1985Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Algirdas C. Poshkus
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Patent number: 4513143Abstract: 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: GrantFiled: December 1, 1982Date of Patent: April 23, 1985Assignee: SRI InternationalInventors: Steven Y. Ng, Donald W. Penhale, Jorge Heller