From Phenol, Phenol Ether, Or Inorganic Phenolate Monomer Patents (Class 526/313)
  • Patent number: 6309585
    Abstract: A high refractive index composition comprising a core resin mixture comprising a mixture of ethoxylated bisphenol A di(meth)acrylates and/or their derivatives having variable degrees of ethoxylation to provide enhanced impact resistance and refractive index.
    Type: Grant
    Filed: April 23, 1999
    Date of Patent: October 30, 2001
    Assignee: Rodenstock North America, Inc.
    Inventor: Qiang Zheng
  • Patent number: 6294630
    Abstract: A polymer used in a chemically amplified resist is represented by the following formula: wherein R1, R3 and R5 are each independently selected from the group consisting of —H, and —CH3; R2 is selected from the group consisting of t-butyl, tetrahydropyranyl, and 1-alkoxyethyl; R4 is selected from the group consisting of —H, —CH3, t-butyl, tetrahydropyranyl, and 1-alkoxyethyl; x is an integer ranging from 1 to 4; and wherein l, m, and n are selected such that l/(l+m+n) ranges from 0.1 to 0.5, m/(l+m+n) ranges from 0.01 to 0.5, and (l+m)/(l+m+n) ranges from 0.1 to 0.7.
    Type: Grant
    Filed: August 11, 1999
    Date of Patent: September 25, 2001
    Assignee: Samsung Electronics Co., Ltd.
    Inventor: Sang-jun Choi
  • Patent number: 6291604
    Abstract: A method for producing poly(p-t-butoxystyrene) by a polymerization reaction of p-t-butoxystyrene characterized in that p-t-butoxystyrene or a solution thereof is added little by little to a mixture of the reaction solvent and the polymerization initiator, and water content of the p-t-butoxystyrene or a solution thereof is in a range of 5-70 ppm, and according to the method, poly(p-t-butoxystyrene) having narrow molecular weight distribution can be produced securely, with easy reaction temperature control.
    Type: Grant
    Filed: September 5, 2000
    Date of Patent: September 18, 2001
    Assignee: Sumitomo Chemical Company Limited
    Inventor: Hiroharu Takeshima
  • Patent number: 6281320
    Abstract: This invention comprises a metallocene catalyst system for the production of high molecular weight polyolefins, particularly polyethylene and higher poly-alpha olefins, and copolymers of ethylene and/or alpha olefins with other unsaturated monomers, including diolefins, acetylenically unsaturated monomers and cyclic olefins. The catalyst system is highly active, at low ratios of Al to transition metal, and hence catalyzes the production of a polyolefin product containing low levels of catalyst metal residues. The catalyst system comprises (i) a metallocene precursor (Component A), aluminoxane (Component B), and phenolic modifier (Component C) or (ii) the reaction product of a metallocene precursor with a phenolic compound (Component A′) and aluminoxane (Component B). There is also provide a polymerization process using the catalyst and the product so produced.
    Type: Grant
    Filed: February 4, 1999
    Date of Patent: August 28, 2001
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Sun-Chueh Kao, Frederick John Karol
  • Patent number: 6281318
    Abstract: There are herein disclosed a poly{1-(1-alkoxyalkoxy)-4-(1-methylethenyl)benzene} having a narrow molecular weight distribution, for example, a poly{1-(1-alkoxyethoxy)-4-(1-methylethenyl)benzene} or a poly{1-(2-tetrahydrofuranyloxy)-4-(1-methylethenyl)benzene} which is useful as a chemical amplification type positive resist material; a preparation process of the polymer which comprises reacting industrially easily available 4-(1-methylethenyl)phenol with a vinyl ether to produce an alkoxyalkoxy compound, and then carrying out an anionic polymerization; and a preparation process of poly{4-(1-methylethenyl)phenol} having a narrow molecular weight distribution useful as a tease polymer for a chemical amplification type positive resist material which comprises reacting the above-mentioned polymer with a protonic acid in the presence of an organic solvent.
    Type: Grant
    Filed: February 27, 1998
    Date of Patent: August 28, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Yoshihiro Yamamoto, Toshiro Takao, Ritsuko Fukuda, Isao Hara
  • Patent number: 6271328
    Abstract: A liquid composition, polymerizable by means of a free-radical route to yield optical articles endowed with a high refractive index, contains an allyl-carbonate derivative definable with the general formula: (wherein R1, X1, X2, X3, X4, X5, X6, a and b are as defined in the disclosure) and a copolymerizable monomer containing at least one ethylenic unsaturation in its molecule.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: August 7, 2001
    Inventors: Franco Rivetti, Fiorenzo Renzi, Ugo Romano
  • Patent number: 6258901
    Abstract: There is provided a process for efficiently and economically producing a polymer which is superior in transmittances of visible light and far-ultraviolet light, has a high molecular weight and is light-colored. A process for producing a light-colored vinylphenol-based polymer by subjecting p-vinylphenol to homopolymerization or subjecting p-vinylphenol and a vinyl compound copolymerizable with p-vinylphenol to copolymerization, in the presence of a cationic polymerization catalyst or a radical polymerization initiator, which process comprises subjecting a p-vinylphenol-containing raw material to vacuum flash distillation in the presence of a phenolic compound having no unsaturated side chain and water and subjecting the resulting p-vinylphenol-containing fraction to polymerization.
    Type: Grant
    Filed: August 7, 2000
    Date of Patent: July 10, 2001
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Masao Kaneko, Tadashi Matsumoto, Nobuyuki Oka, Kunishige Ohtsu
  • Patent number: 6252025
    Abstract: Photographically useful materials are disclosed comprising a hyperbranched polymer segment and multiple pendant photographically useful groups. Such materials may be prepared by forming an active hyperbranched polymer segment with multiple functionalized end group sites, and reacting the active hyperbranched polymer segment with an active compound comprising a photographically useful group to form a hyperbranched polymer ended with photographically useful groups. The hyperbranched segment may comprise any kind of polymer segment with hyperbranched architecture, and the active end groups may comprise any kind of reactive site. The active hyperbranched polymer may comprise any kind of other functional groups which are located in either backbone or the ends.
    Type: Grant
    Filed: August 11, 1998
    Date of Patent: June 26, 2001
    Assignee: Eastman Kodak Company
    Inventors: Jin-Shan Wang, Yanong Wang
  • Patent number: 6245482
    Abstract: There is provided a polymer for use in a chemically amplified resist and represented by the following formula: where R′ is one selected from the group consisting of: in which R1 is one selected from the group consisting of —H and —CH3, and m and n are integers, and where R2 is one selected from the group consisting of —H and —CH3, R3 is one selected from the group consisting of —H and —CH3, R4 is one selected from the group consisting of —H, —CH3 and —CH2CH2OH, p, q and r are integers, p/(p+q+r) is 0.1˜0.7, q/(p+q+r) is 0.1˜0.7, and r/(p+q+r) is 0.1˜0.5.
    Type: Grant
    Filed: February 23, 2000
    Date of Patent: June 12, 2001
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang-jun Choi, Joo-tae Moon
  • Patent number: 6231714
    Abstract: Curable compositions include at least one monomer compound having both (meth)acrylic ester functionality and an allylic phenyl ether functional group on the same molecule, the allylic phenyl ether functional group having at least one unsubstituted position on the phenyl ring which is ortho or para to the allylic ether group, and a free radical catalyst system. The composition may also includes a latent thermally activated acid generator. Claisen Rearrangement of radically polymerized polymers produced from the compositions may be induced at temperatures of about 100° C. or more to give crosslinked products of improved thermal resistance.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: May 15, 2001
    Assignee: Loctite Corporation
    Inventors: John G. Woods, Susanne Morrill, Ciaran B. McArdle
  • Patent number: 6221989
    Abstract: A novel polymer is provided in the form of a novolac resin in which some of the hydrogen atoms of hydroxyl groups are replaced by 1,2-naphthoquinonediazidosulfonyl ester groups, triazinyl groups and optionally, substituted carbonyl or sulfonyl groups. A positive resist composition comprising the polymer has improved sensitivity, resolution and developability in microfabrication as well as improved heat resistance and low-temperature curability in forming interlayer insulating film.
    Type: Grant
    Filed: May 13, 1999
    Date of Patent: April 24, 2001
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomoyoshi Furihata, Hideto Kato, Satoshi Okazaki
  • Patent number: 6218485
    Abstract: A process for producing a monodisperse polymer which has a number-average molecular weight from 1,000 to 100,000 and a molecular weight distribution Mw (weight-average molecular weight)/Mn (number-average molecular weight)=1.00 through 1.50 is disclosed. This process comprises: homopolymerizing or random copolymerizing an anionic polymerizable compound by living anionic polymerization using an organic alkali metal and/or an alkali metal as a polymerization initiator, wherein a target molecular weight is obtained by adding the compound divided into multiple steps.
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: April 17, 2001
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Hiroo Muramoto, Yukikazu Nobuhara, Eiichiro Kobayashi
  • Patent number: 6197905
    Abstract: A process for the production of polymers by free radical polymerization, characterized in that there is added to the polymerization system one or more compounds of general formula (A), where R1 is a group capable of activating the vinylic carbon towards free radical addition; Y is OR2, where R2 is an optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted saturated or unsaturated carbocyclic or heterocyclic ring; X is an element other than carbon selected from the Groups, IV, V, VI or VII of the Periodic Table or a group consisting of an element selected from the Groups IV, V, or VI to which is attached one or more oxygen atoms; and n is a number from 0 to 3, such that the valency of the group X is satisfied and, when n is greater than 1, the groups represented by R2 are identical or different.
    Type: Grant
    Filed: March 21, 1997
    Date of Patent: March 6, 2001
    Assignee: Commonwealth Scientific & Industrial Resarch Organization
    Inventors: Ezio Rizzardo, Gordon Francis Meijs, San Hoa Thang
  • Patent number: 6156477
    Abstract: A polymer comprising recurring units of formula (1) is provided wherein some hydrogen atoms of phenolic hydroxyl groups and/or carboxyl groups are replaced by acid labile groups. The polymer is crosslinked with a crosslinking group having a C--O--C linkage resulting from reaction of some of the remaining phenolic hydroxyl groups and/or carboxyl groups with an alkenyl ether compound or halogenated alkyl ether compound. The amount of the acid labile group and the crosslinking group combined is on the average from more than 0 mol % to 80 mol % of the entirety of the phenolic hydroxyl group and carboxyl group. The polymer has Mw of 1,000-500,000. R.sup.1 is H or methyl, R.sup.2 is C.sub.1 -C.sub.8 alkyl, R.sup.3 is H, R.sup.4 is --COOR.sup.5, C.sub.1 -C.sub.5 alkyl or phenyl, or R.sup.3 and R.sup.4, taken together, may form --COOCO--, R.sup.5 is H or C.sub.1 -C.sub.8 alkyl, x and y are integers satisfying x+y.ltoreq.5, p and q are positive numbers satisfying p+q=1 and 0<q/(p+q).ltoreq.0.9.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: December 5, 2000
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Kiyoshi Motomi, Osamu Watanabe, Satoshi Watanabe, Shigehiro Nagura, Toshinobu Ishihara
  • Patent number: 6147177
    Abstract: Polycyclic polymers containing pendant aromatic moieties are disclosed. The polymers exhibit light transparency properties to deep UV wave lengths making them useful for high resolution photolithographic applications. These polymers are particularly useful in chemically amplified positive and negative tone resists.
    Type: Grant
    Filed: February 19, 1999
    Date of Patent: November 14, 2000
    Assignees: The B. F. Goodrich Company, International Business Machines Corporation
    Inventors: Saikumar Jayaraman, Brian Leslie Goodall, Larry Funderburk Rhodes, Robert Adam Shick, Richard Vicari, Robert David Allen, Juliann Opitz, Ratnam Sooriyakumaran, Thomas Wallow
  • Patent number: 6107425
    Abstract: The invention provides inter alia new methods to produce aqueous developable resin binders for negative-acting photoresists. The methods in general comprise free radical polymerization of one or more types of monomers in the presence of a free radical polymerization control agent, particularly a nitroxide polymerization control agent such as a piperidinyloxy (N-oxy) free radical, and wherein at least one of the monomer types contains a moiety that enables aqueous solution development of a photoresist composition containing the formed polymer.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: August 22, 2000
    Assignee: Shipley Company, L.L.C.
    Inventors: Roger F. Sinta, George G. Barclay, Jacque H. Georger, Jr., Mark D. Denison, Sheri L. Ablaza
  • Patent number: 6100316
    Abstract: The invention relates to radiation-curable coating materials which compriseA a synthetic resin containing from 1.5 to 5 mol/kg, preferably from 3.6 to 4.5 mol/kg, of ethylenically unsaturated double bonds of which not more than 10% are vinyl groups, or a mixture of such synthetic resins, andB a compound of the general formula Ar--O--R.sub.1 --O--CO--CR.sub.2 .dbd.CH.sub.2, where Ar is an optionally substituted aryl radical, R.sub.1 is an alkylene radical having 1 to 6 carbon atoms and R.sub.2 is a hydrogen atom or an alkyl radical having 1 to 3 carbon atoms, or a mixture of such compounds,from 10 to 70% by weight of the total quantity of A and B comprising component A and from 30 to 90% by weight of the total quantity of A and B comprising component B.
    Type: Grant
    Filed: January 6, 1997
    Date of Patent: August 8, 2000
    Assignee: BASF Coatings AG
    Inventor: Martin Lobert
  • Patent number: 6051362
    Abstract: A polymer for use in a chemically amplified photoresist and represented by the following formula: ##STR1## where R' is one selected from the group including: ##STR2## in which R.sub.1 is one selected from the group including --H and --CH.sub.3, m and n are integers, and m/(m+n)=0.1-0.
    Type: Grant
    Filed: February 17, 1999
    Date of Patent: April 18, 2000
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang-jun Choi, Joo-tae Moon
  • Patent number: 6051670
    Abstract: A gelling composition and a process for using the gelling composition for oilfield applications are provided. The gelling composition comprises a water-soluble polymer, a crosslinking agent, and a liquid wherein the water-soluble polymer comprises repeat units derived from a nitrogen-containing olefinic monomer and optionally an olefinic comonomer. The gelling composition can be used in drilling fluids, workover fluids, completion fluids, permeability corrections, water or gas coning prevention, fluid loss prevention, matrix acidizing, fracture acidizing, and combinations of any two or more thereof.
    Type: Grant
    Filed: December 20, 1995
    Date of Patent: April 18, 2000
    Assignee: Phillips Petroleum Company
    Inventors: Iqbal Ahmed, Ahmad Moradi-Araghi, Aly-Anis Hamouda, Odd Ivar Eriksen
  • Patent number: 6048661
    Abstract: Provided are polymeric compounds which, when used as base resins in resist materials, can yield chemical resist materials having high sensitivity, high resolution, a high exposure latitude, and good process adaptability, exhibiting excellent resistance to plasma etching, and giving resist patterns having high thermal resistance, as well as chemically amplified positive type resist materials using such polymeric compounds as base resins. These chemically amplified positive type resist materials use a base resin comprising a polymeric compound having a weight-average molecular weight of 1,000 to 500,000 and having one or more hydroxyl and/or carboxyl groups in the molecule, part or all of the hydrogen atoms of the hydroxyl and/or carboxyl groups being replaced by groups of the following general formula ##STR1## and additionally contain an acid generator, a dissolution inhibitor, a basic compound, and an aromatic compound having a group of the formula .tbd.C--COOH.
    Type: Grant
    Filed: March 2, 1998
    Date of Patent: April 11, 2000
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Jun Hatakeyama, Shigehiro Nagura, Toshinobu Ishihara
  • Patent number: 6034193
    Abstract: The invention relates to photochromic transparent organic materials presenting an index of refraction of more than 1.55, which are free of optical distortions and are prepared by radical polymerization of a polymerizable composition comprising:a) 80-95 wt % of at least one monomer represented by the general formula (I): ##STR1## where R=H or CH.sub.3, and m and n are independently 1 or 2; b) 5-20 wt % of at least one aromatic monovinyl monomer represented by the general formula (II): ##STR2## c) an effective quantity of at least one dye that imparts photochromic properties to the material, selected from the groups of spiroxazines, spiropyrans and chromenes;d) an effective quantity of a chain transfer agent; ande) an effective quantity of a radical polymerization initiator, characterized in that the chain transfer agent is a linear alkanethiol and the radical polymerization initiator is a diazo compound.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: March 7, 2000
    Assignee: Corning Incorporated
    Inventors: David Henry, Jacques Vial
  • Patent number: 6033828
    Abstract: A polymer comprising recurring units of formula (1) is provided wherein some of the hydrogen atoms of phenolic hydroxyl groups and/or alcoholic hydroxyl groups are replaced by acid labile groups. The polymer is crosslinked within a molecule and/or between molecules with a crosslinking group having a C--O--C linkage resulting from reaction of some of the remaining phenolic hydroxyl groups and/or alcoholic hydroxyl groups with an alkenyl ether compound or halogenated alkyl ether compound. The amount of the acid labile group and the crosslinking group combined is on the average from more than 0 mol % to 80 mol % of the entirety of the phenolic hydroxyl group and alcoholic hydroxyl group. The polymer has Mw of 1,000-500,000. ##STR1## R.sup.1 is H or methyl, R.sup.2 is C.sub.1 -C.sub.8 alkyl, letter x is 0 or a positive integer, y is a positive integer, x+y.ltoreq.5, letters p and q are positive numbers satisfying p+q=1 and 0<q/(p+1).ltoreq.0.9.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: March 7, 2000
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Junji Shimada, Osamu Watanabe, Satoshi Watanabe, Shigehiro Nagura, Toshinobu Ishihara
  • Patent number: 6027854
    Abstract: A polymer comprising recurring units of formula (1) is provided wherein some hydrogen atoms of phenolic hydroxyl groups and/or alcoholic hydroxyl groups and/or carboxyl groups are replaced by acid labile groups. The polymer is crosslinked with a crosslinking group having a C--O--C linkage resulting from reaction of some of the remaining alcoholic hydroxyl groups and/or carboxyl groups with an alkenyl ether compound or halogenated alkyl ether compound. The amount of the acid labile group and the crosslinking group combined is on the average from more than 0 mol % to 80 mol % of the entirety of the phenolic hydroxyl group, alcoholic hydroxyl group and carboxyl group. The polymer has Mw of 1,000-500,000. ##STR1## R.sup.1 is H or methyl, R.sup.2 is C.sub.1 -C.sub.8 alkyl, R.sup.3 is a divalent C.sub.1 -C.sub.18 hydrocarbon group which may have a hetero atom, R.sup.4 and R.sup.5 are H or monovalent C.sub.1 -C.sub.18 hydrocarbon groups which may have a hetero atom, x and y are integers satisfying x+y.ltoreq.
    Type: Grant
    Filed: February 27, 1998
    Date of Patent: February 22, 2000
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Osamu Watanabe, Satoshi Watanabe, Shigehiro Nagura, Toshinobu Ishihara
  • Patent number: 5998557
    Abstract: In general, the invention provides polymers which may be used in chemically amplified resists. More particularly, the invention relates to esterified polymers containing the group: ##STR1## Resist compositions comprise the esterified polymers and photoacid generators.
    Type: Grant
    Filed: March 9, 1999
    Date of Patent: December 7, 1999
    Assignee: Samsung Electronics Co., Ltd.
    Inventor: Sang-jun Choi
  • Patent number: 5989775
    Abstract: A copolymer having a repeating unit represented by the following general formula I and a chemical amplification positive photoresist composition having the copolymer and a photoacid generator. The photoresist can allow for a good pattern shape even though a post-baking is taken in a somewhat delayed time and for a use of any radiation, such as uv light, deep uv light and charged particle beam. Also, it is superior in storage stability and resolution so that it is useful for the high integration of semiconductor devices. The polymer ranges, in polystyrene-reduced average molecular weight, from 1,000 to 1,000,000. The polymer is represented by the following repeating pattern: ##STR1## wherein, R.sub.1, R.sub.2 and R.sub.3 independently represent a hydrogen atom or a methyl; R.sub.4, R.sub.5 and R.sub.6 independently represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen; 1, m, n each is a repeating number satisfying the condition that 0.3<1/(m+n)<0.9, 0.1<m/(1+n)<0.6 and 0.
    Type: Grant
    Filed: December 26, 1997
    Date of Patent: November 23, 1999
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Joo-Hyeon Park, Ji-Hong Kim, Ki-Dae Kim, Sun-Yi Park, Seong-Ju Kim
  • Patent number: 5981145
    Abstract: The present invention relates to a novel polymer suitable for use as an antireflective coating or as an additive in photoresist for absorption of reflected light. The novel polymer comprises at least one unit containing a dye that absorbs from about 180 nm to about 450 nm and at least one unit that contains no aromatic funtionality. The polymer is soluble in organic solvents, preferrably solvents of low toxicity, or it may be soluble in water, which may additionally contain other water miscible organic solvents.
    Type: Grant
    Filed: April 30, 1997
    Date of Patent: November 9, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Shuji Ding, Dinesh N. Khanna, Ping-Hung Lu, Jianhui Shan, Ralph R. Dammel, Dana L. Durham, M. Dalil Rahman, Iain McCulloch
  • Patent number: 5981141
    Abstract: In general, the invention provides polymers which may be used in chemically amplified resists. More particularly, the invention relates to esterified polymers containing the group: ##STR1## Resist compositions comprise the esterified polymers and photoacid generators.
    Type: Grant
    Filed: October 1, 1997
    Date of Patent: November 9, 1999
    Assignee: Samsung Electrics Co., Ltd.
    Inventors: Sang-jun Choi, Chun-geun Park, Hai-won Lee
  • Patent number: 5965680
    Abstract: Describes polymerizable organic compositions of from about 30 to 95 weight percent of a first monomer component which is a polyol[(meth)acryloyl terminated carbonate], e.g., diethylene glycol bis[(methacryloyloxy)ethylene carbonate)]; and from about 5 to 70 weight percent of at least one monomer component selected from: (i) an alkoxylated diol, e.g., alkoxylated bisphenol, having acrylate or methacrylate groups, e.g., dimethacrylate of bisphenol A having 25 to 35 ethoxy units, (ii) a bis[(meth)acryloyl-terminated]polyethylene glycol, and (iii) a monomer having at least three ethylenically-unsaturated terminal groups. Substantially completely cured polymerizates prepared from such compositions may be used to prepare photochromic articles, e.g., lenses, by incorporating a photochromic substance, e.g., by thermal transfer, into the polymerizate.
    Type: Grant
    Filed: November 27, 1996
    Date of Patent: October 12, 1999
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Robert D. Herold, Charles R. Wiedrich, Ajay D. Parkhe, Christopher D. Selvig, Robert A. Smith
  • Patent number: 5962186
    Abstract: A positive chemical amplified photoresist composition comprising as a matrix resin a polymer having the repeating unit of Formula (I) and a photoacid generator. The polymer ranges, in polystyrene-reduced weight average molecular weight, from about 2,000 to 1,000,000. The photoresist composition is possible to develop in alkali and shows excellent sensitivity, resolution and transmissivity to deep uv light in addition to being superior in storage preservativity. The repeating unit is: ##STR1## wherein, R.sub.1, R.sub.2 and R.sub.3 are independently represented by a hydrogen atom or a methyl group; R.sub.4 is a hydrogen atom, an alkyl group or an alkoxy group; R.sub.5, R.sub.6 and R.sub.7 are independently represented by a hydrogen atom, a methyl group, an ethyl group, a t-butyl group, a tetrahydropyranyl group or an alkoxymethylene group; j is an integer of 1-8; k is an integer of 0-8; and l, m and n each represent a mole ratio, satisfying the condition of 1=0.1.about.0.5/l+m+n, m=0.3.about.0.8/l+m+n, n=0.1.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: October 5, 1999
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Joo Hyeon Park, Seong Ju Kim, Ji Hong Kim, Ki Dae Kim
  • Patent number: 5959051
    Abstract: Vinylphenol polymers are useful materials having many applications, vinylphenol polymers possessing an appropriate molecular weight corresponding to each of the applications are desired. However, it is very difficult to control the molecular weight of vinylphenol polymers, because vinylphenol monomer exhibits a very high reaction rate in the presence of a radical initiator, and it is very difficult to obtain vinylphenol polymers having molecular weight of from eight thousand to one hundred thousand. Further, vinylphenol monomer is very difficult to store, because it is rapidly polymerized even at room temperature. A simple process for preparing vinylphenol polymers having the molecular weight range mentioned above by simply adding methanol to the polymerization system is disclosed. A stabilized composition of vinylphenol suitable for use to prepare vinylphenol polymers, comprising vinylphenol-containing polymerization raw material and methanol as the indispensable constituents is also disclosed.
    Type: Grant
    Filed: January 7, 1999
    Date of Patent: September 28, 1999
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Masao Kaneko, Takeshi Noguchi, Nobuyuki Oka
  • Patent number: 5942555
    Abstract: A photoactivatable reagent useful as a chain transfer reagent for providing a semitelechelic polymer having one or more terminal photoactivatable groups. The reagent provides one or more photoactivatable groups and one or more sulfhydryl (or other chain transfer) groups, the photoactivatable and chain transfer groups optionally being joined together by a spacer group. The reagent can be used to prepare a polymer by serving to initiate the polymerization of ethylenically unsaturated monomers. The reagent itself becomes an integral part of the resultant polymer, thereby providing the polymer with a terminal photoactivatable nature. The method provides a number of benefits, including the ability to provide homogeneous photoactivatable polymer compositions, e.g., in terms of the uniform location of the photogroup(s) on the terminal portion of each polymer molecule and the ability to build a desired nonpolar quality, and in turn improved surfactancy, into otherwise polar polymers.
    Type: Grant
    Filed: March 21, 1996
    Date of Patent: August 24, 1999
    Assignee: SurModics, Inc.
    Inventors: Melvin J. Swanson, Richard A. Amos, Dale G. Swan, Gary W. Opperman
  • Patent number: 5922821
    Abstract: High refractive index copolymers suitable for use in ophthalmic lenses, such as foldable intraocular lenses, are disclosed. The high refractive index copolymers of the present invention consist essentially of (i) one or more monomers having the structure: ##STR1## wherein: X is H or CH.sub.3 ;m is 0-10;Y is nothing, O, S, or NR wherein R is H, CH.sub.3, C.sub.n H.sub.2n+1 (n=1-10) isoOC.sub.3 H.sub.7, C.sub.6 H.sub.5, or CH.sub.2 C.sub.6 H.sub.5 ;Ar is any aromatic ring which can be unsubstituted or substituted with H,CH.sub.3, C.sub.2 H.sub.5, n--C.sub.3 H.sub.7, iso--C.sub.3 H.sub.7, OCH.sub.3, C.sub.6 H.sub.11, Cl, Br, C.sub.6 H.sub.5, or CH.sub.2 C.sub.6 H.sub.5 ;and (ii) one or more monomers having the structure: ##STR2## wherein: X, X' is independently H or CH.sub.3 ;n, n' are independently 2 or 3;m, m' are independently 2-25;Ar, Ar' are independently as defined above;a is 1 or 2; andZ is C(CH.sub.3).sub.2 or S(.dbd.O).sub.2.
    Type: Grant
    Filed: August 8, 1997
    Date of Patent: July 13, 1999
    Assignee: Alcon Laboratories, Inc.
    Inventors: Albert R. LeBoeuf, Mutlu Karakelle
  • Patent number: 5919603
    Abstract: In an additive process for producing printed wiring boards, by using a developer comprising a chlorine-free organic solvent and an alkaline aqueous solution and as a resist material a copolymer of methacrylic acid and methyl methacrylate or the like, the production steps are simplified even if a substrate having a large area is used, and abolishment of chlorine-containing organic solvent as a developer becomes possible.
    Type: Grant
    Filed: October 29, 1997
    Date of Patent: July 6, 1999
    Assignee: Hitachi, Ltd.
    Inventors: Masashi Miyazaki, Haruo Akahoshi, Shozo Nohara, Kenzi Kikuta, Toshiaki Ishimaru
  • Patent number: 5902838
    Abstract: Cationically curable adhesives and sealants with increased viscosities and improved rheological control and good storage stability are prepared using a cationically curable monomer and a thickening polymer which is the alkylation reaction product of poly(4-hydroxystyrene) or poly(2-hydroxystyrene) with a compound RX where R is allyl, methallyl, crotyl or prenyl and X is Cl, Br or I. The cationically curable monomer suitably includes at least one alkenyloxystyrene monomer. Such thickened adhesives are useful as edge sealants for flat panel display devices. A-stage curing of the adhesive with UV irradiation allows for near ambient temperature fixturing of the device assemblies and B-stage thermal curing of the adhesive can be conducted at much lower temperatures than are needed for glass frit sealants. The B-stage cured products have thermal resistance, outgassing and substrate adhesion properties adequate for flat panel display devices.
    Type: Grant
    Filed: October 1, 1996
    Date of Patent: May 11, 1999
    Assignee: Loctite Corporation
    Inventors: John G. Woods, Maria L. Masterson, Matthew P. Burdzy, Bernard M. Malofsky
  • Patent number: 5882835
    Abstract: A chemical amplified positive photoresist composition including a resin having the repeating unit of Formula I and a photoacid generator. The resin ranges, in polystyrene-reduced molecular weight, from about 2,000 to 1,000,000. In Formula I, k and l each represent a mole ratio satisfying the condition of k+l=l. R.sub.1 is a hydrogen atom or a methyl group. R.sub.2 and R.sub.3 are independently either a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. R.sub.4 is an acetate group, a t-butoxycarbonyl group, a benzyl group, a trialkylsilyl group or an alkyl group. The photoacid generator which generates an acid by radiation.
    Type: Grant
    Filed: September 17, 1997
    Date of Patent: March 16, 1999
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Joo-Hyeon Park, Seong-Ju Kim, Ki-Dae Kim, Sun-Yi Park
  • Patent number: 5883210
    Abstract: A gelling composition and a process for using the gellimg composition for oilfield applications are provided. The gelling composition comprises a water-soluble polymer, a crosslinking agent, and a liquid wherein the water-soluble polymer comprises repeat units derived from a nitrogen-containing olefinic monomer and optionally an olefinic comonomer. The gelling composition can be used in drilling fluids, workover fluids, completion fluids, permeability corrections, water or gas coning prevention, fluid loss prevention, matrix acidizing, fracture acidizing, and combinations of any two or more thereof.
    Type: Grant
    Filed: September 19, 1997
    Date of Patent: March 16, 1999
    Assignee: Phillips Petroleum Company
    Inventors: Iqbal Ahmed, Ahmad Moradi-Araghi, Aly-Anis Hamouda, Odd Ivar Eriksen
  • Patent number: 5879852
    Abstract: The invention relates to a positive-working radiation-sensitive mixture containing a) a polymeric binder having acid-labile groups and b) a compound which forms a strong acid on irradiation, in which the binder simultaneously contains units of the formulae I, II and IIIR.sup.1 --OH (I),R.sup.1 --O--CO.sub.2 R.sup.2 (II)R.sup.1 --O--CH.sub.2 --CHR.sup.3 --OH (III).The mixture is used to coat radiation-sensitive recording material which can be used to produce printing plates and photoresists.
    Type: Grant
    Filed: April 30, 1997
    Date of Patent: March 9, 1999
    Assignee: AGFA-Gevaert AG
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5872200
    Abstract: A paper coating formulation and a process for making a paper coating formulation having an improved strength and blister resistance including an aqueous medium having dispersed therein a functionally effective amount of a finely divided mineral filler and a latex binder containing copolymerized acid functional and amine functional monomers in each polymer molecule.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: February 16, 1999
    Assignee: GenCorp Inc.
    Inventors: Satish C. Sharma, Charles M. Kausch, Ronald D. Mohan, Raymond J. Weinert
  • Patent number: 5863989
    Abstract: A curable resin composition comprising:(1) a polymerizable vinyl monomer having a structure of the formula (A):Z--R--(R.sub.2 O).sub.p --R.sub.1 (A)wherein Z is a (meth)acryloyl group, R.sub.1 is a phenyl group or a phenyl group having a C.sub.1-3 alkyl group, R.sub.2 is --C.sub.2 H.sub.4 --, --C.sub.3 H.sub.6 --, --CH.sub.2 CH(CH.sub.3)--, --C.sub.4 H.sub.8 -- or --C.sub.6 H.sub.12 --, and p is an integer of from 1 to 10 and wherein R is a direct bond,(2) a polymerizable vinyl monomer having a structure of the formula (B): ##STR1## wherein Z and R.sub.2 are as defined above, R.sub.3 is hydrogen or a C.sub.1-4 alkyl group, and q is an integer of from 0 to 8,(3) a polymerizable vinyl monomer having a structure of the formula (C):Z--O--(R.sub.2 O).sub.p --H (C)wherein Z, R.sub.2 and p are as defined above,(4) an organic peroxide, and(5) a reducing agent.
    Type: Grant
    Filed: April 17, 1997
    Date of Patent: January 26, 1999
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Koichi Taguchi, Hiroshi Suto
  • Patent number: 5856411
    Abstract: Resins for use in chemically amplified resists are represented by the general formula (I): ##STR1## wherein R.sub.1 is t-butyl or tetrahydropyranyl; R.sub.2 is hydrogen or methyl; n and m are integers; and the ratio n/((m+n) ranges from 0.1 to 0.9. Methods for manufacturing the resins comprise reacting a monomer represented by the formula (II): ##STR2## with a monomer represented by the formula (III): ##STR3## to form a copolymer represented by the formula (IV): ##STR4## wherein R.sub.1 and R.sub.2 are defined as above; and hydrolyzing acetoxy groups contained in the copolymer represented by the formula (IV) to form the resin compositions.
    Type: Grant
    Filed: June 17, 1996
    Date of Patent: January 5, 1999
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang-jun Choi, Chun-geun Park
  • Patent number: 5844057
    Abstract: The invention provides a novel polymer comprising a recurring unit of formula. (1) wherein R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or acid labile group, at least one R.sup.2 being hydrogen and at least one R.sup.2 being an acid labile group, and n=2 or 3. The polymer's Mw is 3,000-300,000. Blending the polymer as a base resin with an organic solvent and a photoacid generator yields a chemically amplified positive resist composition.
    Type: Grant
    Filed: April 11, 1996
    Date of Patent: December 1, 1998
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Osamu Watanabe, Yoshihumi Takeda, Junji Tsuchiya, Toshinobu Ishihara
  • Patent number: 5811503
    Abstract: Describes polymerizable organic compositions of from about 30 to 95 weight percent of a first monomer component which is an alkoxylated diol, e.g., alkoxylated bisphenol, having acrylate or methacrylate groups, i.e., dimethacrylate of bisphenol A having an average of 1 to 4 ethoxy units, and from about 5 to 70 weight percent of a second monomer component which is an alkoxylated diol, e.g., alkoxylated bisphenol, having acrylate or methacrylate groups, i.e., dimethacrylate of bisphenol A having 25 to 70 ethoxy units. Optionally there may also be present from about 0 to 65 weight percent of at least one monomer component which is selected from: (i) a monoethylenically unsaturated monomer that is polymerizable by free radical initiation; (ii) a bis?(meth)acryloyl-terminated!polyethylene glycol monomer; and (iii) a monomer having at least three terminal ethylenically-unsaturated groups. Substantially completely cured polymerizates prepared from such compositions may be used to prepare photochromic articles, e.g.
    Type: Grant
    Filed: November 27, 1996
    Date of Patent: September 22, 1998
    Assignee: PPG Industries, Inc.
    Inventors: Robert D. Herold, Randy E. Daughenbaugh, Charles R. Wiedrich
  • Patent number: 5807947
    Abstract: A polymer of (a) an unsubstituted 4-hydroxystyrene monomer and (b) a substituted 4-hydroxystyrene monomer of the formula ##STR1## wherein A, B, C, and D are independently H or C.sub.1 to C.sub.4 alkyl wherein at least one of B and D is C.sub.1 to C.sub.4 alkyl; and wherein said copolymer has a molecular weight of from about 800 to about 100,000; and wherein the mol ratio of monomer (a) to monomer (b) ranges from about 3:1 to about 1:3.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: September 15, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Richard Vicari, Douglas J. Gordon, William D. Hinsberg, Dennis R. McKean, Carlton G. Willson, Ralph Dammel
  • Patent number: 5741873
    Abstract: The present invention relates to a composition comprising at least one alkoxylated bisphenol-A diacrylate or dimethacrylate, ethylene glycol dimethacrylate, and at least one vinyl monomer. The composition is suitable for use in the fiberglass reinforced plastic art. The composition possesses similar or superior physical properties compared to unsaturated polyester based specialty resins, including emitting lower levels of organic volatiles than typical resins used in the art.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: April 21, 1998
    Assignee: Aristech Chemical Corporation
    Inventors: Ronald A. Andrekanic, Joseph Pugach, Thomas W. Smeal
  • Patent number: 5714559
    Abstract: Polymers based on combination of different repeating units derived from hydroxy styrene and hydroxyvinylcyclohexane derivatives wherein a portion of the hydroxyl groups are replaced with either acid-labile acetal or ketal protecting groups and where a portion of the repeating groups comprise two crosslinked species connected via the protecting groups.
    Type: Grant
    Filed: December 14, 1995
    Date of Patent: February 3, 1998
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Hans-Thomas Schacht, Norbert Muenzel, Carl-Lorenz Mertesdorf, Pasquale Alfred Falcigno, Heinz Holzwarth, Ottmar Rohde, deceased, Hans-Jorg Kirner
  • Patent number: 5708109
    Abstract: A pressure sensitive adhesive that includes the polymerization product of:(a) 25-97 parts by weight of an acrylic acid ester of a monohydric alcohol whose homopolymer has a T.sub.g less than 0.degree. C.;(b) 3-75 parts by weight of a non-polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of no greater than 10.50 and a T.sub.g greater than 15.degree. C.; and(c) 0-5 parts by weight of a polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of greater than 10.50 and a T.sub.g greater than 15.degree. C. The relative amounts of the acrylic acid ester, the non-polar ethylenically unsaturated monomer, and the polar ethylenically unsaturated monomer are chosen such that the 90.degree. peel adhesion of the pressure sensitive adhesive to a surface provided with 1.5.+-.0.25 mg/in.sup.2 oil is greater than zero after a 10 second dwell at room temperature as measured according to Test Procedure B.
    Type: Grant
    Filed: February 6, 1997
    Date of Patent: January 13, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Greggory S. Bennett, Christopher A. Haak
  • Patent number: 5708110
    Abstract: A pressure sensitive adhesive that includes the polymerization product of:(a) 25-97 parts by weight of an acrylic acid ester of a monohydric alcohol whose homopolymer has a T.sub.g less than 0.degree. C.;(b) 3-75 parts by weight of a non-polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of no greater than 10.50 and a T.sub.g greater than 15.degree. C.; and(c) 0-5 parts by weight of a polar ethylenically unsaturated monomer whose homopolymer has a solubility parameter of greater than 10.50 and a T.sub.g greater than 15.degree. C. The relative amounts of the acrylic acid ester, the non-polar ethylenically unsaturated monomer, and the polar ethylenically unsaturated monomer are chosen such that the 90.degree. peel adhesion of the pressure sensitive adhesive to a polypropylene surface is at least 2 lbs/0.5 in. after a 72 hour dwell at room temperature as measured according to Test Procedure B.
    Type: Grant
    Filed: February 6, 1997
    Date of Patent: January 13, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Greggory S. Bennett, Christopher A. Haak
  • Patent number: 5708064
    Abstract: Organic ophthalmic articles are photochromic and have high indices of refraction.
    Type: Grant
    Filed: October 13, 1994
    Date of Patent: January 13, 1998
    Assignee: PPG Industries, Inc.
    Inventors: Charles R. Coleman, Robert D. Herold, Christopher D. Selvig
  • Patent number: 5702825
    Abstract: The present invention relates to a new polymer compositions for use in the manufacture of ophthalmic lenses, to their use in ophthalmology and to apparatus using these lenses, such as eyepieces and film/video camera optics.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: December 30, 1997
    Assignee: Essilor International (Compagnie Generale d'Optique)
    Inventors: Gabriel Keita, Joel Renaudineau, Leanirith Yean
  • Patent number: 5693732
    Abstract: A paper coating formulation and a process for making a paper coating formulation having an improved strength and blister resistance including an aqueous medium having dispersed therein a functionally effective amount of a finely divided mineral filler and a latex binder containing copolymerized acid functional and amine functional monomers in each polymer molecule.
    Type: Grant
    Filed: January 8, 1996
    Date of Patent: December 2, 1997
    Assignee: GenCorp. Inc.
    Inventors: Satish C. Sharma, Charles M. Kausch, Ronald D. Mohan, Raymond J. Weinert