From Phenol, Phenol Ether, Or Inorganic Phenolate Monomer Patents (Class 526/313)
-
Patent number: 6309585Abstract: 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: GrantFiled: April 23, 1999Date of Patent: October 30, 2001Assignee: Rodenstock North America, Inc.Inventor: Qiang Zheng
-
Patent number: 6294630Abstract: 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: GrantFiled: August 11, 1999Date of Patent: September 25, 2001Assignee: Samsung Electronics Co., Ltd.Inventor: Sang-jun Choi
-
Patent number: 6291604Abstract: 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: GrantFiled: September 5, 2000Date of Patent: September 18, 2001Assignee: Sumitomo Chemical Company LimitedInventor: Hiroharu Takeshima
-
Patent number: 6281320Abstract: 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: GrantFiled: February 4, 1999Date of Patent: August 28, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Sun-Chueh Kao, Frederick John Karol
-
Patent number: 6281318Abstract: 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: GrantFiled: February 27, 1998Date of Patent: August 28, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Yoshihiro Yamamoto, Toshiro Takao, Ritsuko Fukuda, Isao Hara
-
Patent number: 6271328Abstract: 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: GrantFiled: February 24, 1989Date of Patent: August 7, 2001Inventors: Franco Rivetti, Fiorenzo Renzi, Ugo Romano
-
Patent number: 6258901Abstract: 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: GrantFiled: August 7, 2000Date of Patent: July 10, 2001Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Masao Kaneko, Tadashi Matsumoto, Nobuyuki Oka, Kunishige Ohtsu
-
Patent number: 6252025Abstract: 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: GrantFiled: August 11, 1998Date of Patent: June 26, 2001Assignee: Eastman Kodak CompanyInventors: Jin-Shan Wang, Yanong Wang
-
Patent number: 6245482Abstract: 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: GrantFiled: February 23, 2000Date of Patent: June 12, 2001Assignee: Samsung Electronics Co., Ltd.Inventors: Sang-jun Choi, Joo-tae Moon
-
Patent number: 6231714Abstract: 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: GrantFiled: November 24, 1998Date of Patent: May 15, 2001Assignee: Loctite CorporationInventors: John G. Woods, Susanne Morrill, Ciaran B. McArdle
-
Patent number: 6221989Abstract: 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: GrantFiled: May 13, 1999Date of Patent: April 24, 2001Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tomoyoshi Furihata, Hideto Kato, Satoshi Okazaki
-
Patent number: 6218485Abstract: 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: GrantFiled: April 24, 2000Date of Patent: April 17, 2001Assignee: Nippon Soda Co., Ltd.Inventors: Hiroo Muramoto, Yukikazu Nobuhara, Eiichiro Kobayashi
-
Patent number: 6197905Abstract: 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: GrantFiled: March 21, 1997Date of Patent: March 6, 2001Assignee: Commonwealth Scientific & Industrial Resarch OrganizationInventors: Ezio Rizzardo, Gordon Francis Meijs, San Hoa Thang
-
Patent number: 6156477Abstract: 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: GrantFiled: January 26, 1998Date of Patent: December 5, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Kiyoshi Motomi, Osamu Watanabe, Satoshi Watanabe, Shigehiro Nagura, Toshinobu Ishihara
-
Patent number: 6147177Abstract: 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: GrantFiled: February 19, 1999Date of Patent: November 14, 2000Assignees: The B. F. Goodrich Company, International Business Machines CorporationInventors: Saikumar Jayaraman, Brian Leslie Goodall, Larry Funderburk Rhodes, Robert Adam Shick, Richard Vicari, Robert David Allen, Juliann Opitz, Ratnam Sooriyakumaran, Thomas Wallow
-
Patent number: 6107425Abstract: 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: GrantFiled: February 6, 1998Date of Patent: August 22, 2000Assignee: Shipley Company, L.L.C.Inventors: Roger F. Sinta, George G. Barclay, Jacque H. Georger, Jr., Mark D. Denison, Sheri L. Ablaza
-
Patent number: 6100316Abstract: 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: GrantFiled: January 6, 1997Date of Patent: August 8, 2000Assignee: BASF Coatings AGInventor: Martin Lobert
-
Patent number: 6051362Abstract: 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: GrantFiled: February 17, 1999Date of Patent: April 18, 2000Assignee: Samsung Electronics Co., Ltd.Inventors: Sang-jun Choi, Joo-tae Moon
-
Patent number: 6051670Abstract: 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: GrantFiled: December 20, 1995Date of Patent: April 18, 2000Assignee: Phillips Petroleum CompanyInventors: Iqbal Ahmed, Ahmad Moradi-Araghi, Aly-Anis Hamouda, Odd Ivar Eriksen
-
Patent number: 6048661Abstract: 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: GrantFiled: March 2, 1998Date of Patent: April 11, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsunehiro Nishi, Jun Hatakeyama, Shigehiro Nagura, Toshinobu Ishihara
-
Patent number: 6034193Abstract: 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: GrantFiled: October 10, 1997Date of Patent: March 7, 2000Assignee: Corning IncorporatedInventors: David Henry, Jacques Vial
-
Patent number: 6033828Abstract: 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: GrantFiled: January 26, 1998Date of Patent: March 7, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Junji Shimada, Osamu Watanabe, Satoshi Watanabe, Shigehiro Nagura, Toshinobu Ishihara
-
Patent number: 6027854Abstract: 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: GrantFiled: February 27, 1998Date of Patent: February 22, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsunehiro Nishi, Osamu Watanabe, Satoshi Watanabe, Shigehiro Nagura, Toshinobu Ishihara
-
Patent number: 5998557Abstract: 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: GrantFiled: March 9, 1999Date of Patent: December 7, 1999Assignee: Samsung Electronics Co., Ltd.Inventor: Sang-jun Choi
-
Patent number: 5989775Abstract: 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: GrantFiled: December 26, 1997Date of Patent: November 23, 1999Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Joo-Hyeon Park, Ji-Hong Kim, Ki-Dae Kim, Sun-Yi Park, Seong-Ju Kim
-
Patent number: 5981145Abstract: 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: GrantFiled: April 30, 1997Date of Patent: November 9, 1999Assignee: Clariant Finance (BVI) LimitedInventors: Shuji Ding, Dinesh N. Khanna, Ping-Hung Lu, Jianhui Shan, Ralph R. Dammel, Dana L. Durham, M. Dalil Rahman, Iain McCulloch
-
Patent number: 5981141Abstract: 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: GrantFiled: October 1, 1997Date of Patent: November 9, 1999Assignee: Samsung Electrics Co., Ltd.Inventors: Sang-jun Choi, Chun-geun Park, Hai-won Lee
-
Patent number: 5965680Abstract: 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: GrantFiled: November 27, 1996Date of Patent: October 12, 1999Assignee: PPG Industries Ohio, Inc.Inventors: Robert D. Herold, Charles R. Wiedrich, Ajay D. Parkhe, Christopher D. Selvig, Robert A. Smith
-
Patent number: 5962186Abstract: 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: GrantFiled: October 10, 1997Date of Patent: October 5, 1999Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Joo Hyeon Park, Seong Ju Kim, Ji Hong Kim, Ki Dae Kim
-
Patent number: 5959051Abstract: 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: GrantFiled: January 7, 1999Date of Patent: September 28, 1999Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Masao Kaneko, Takeshi Noguchi, Nobuyuki Oka
-
Patent number: 5942555Abstract: 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: GrantFiled: March 21, 1996Date of Patent: August 24, 1999Assignee: SurModics, Inc.Inventors: Melvin J. Swanson, Richard A. Amos, Dale G. Swan, Gary W. Opperman
-
Patent number: 5922821Abstract: 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: GrantFiled: August 8, 1997Date of Patent: July 13, 1999Assignee: Alcon Laboratories, Inc.Inventors: Albert R. LeBoeuf, Mutlu Karakelle
-
Patent number: 5919603Abstract: 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: GrantFiled: October 29, 1997Date of Patent: July 6, 1999Assignee: Hitachi, Ltd.Inventors: Masashi Miyazaki, Haruo Akahoshi, Shozo Nohara, Kenzi Kikuta, Toshiaki Ishimaru
-
Patent number: 5902838Abstract: 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: GrantFiled: October 1, 1996Date of Patent: May 11, 1999Assignee: Loctite CorporationInventors: John G. Woods, Maria L. Masterson, Matthew P. Burdzy, Bernard M. Malofsky
-
Patent number: 5882835Abstract: 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: GrantFiled: September 17, 1997Date of Patent: March 16, 1999Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Joo-Hyeon Park, Seong-Ju Kim, Ki-Dae Kim, Sun-Yi Park
-
Patent number: 5883210Abstract: 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: GrantFiled: September 19, 1997Date of Patent: March 16, 1999Assignee: Phillips Petroleum CompanyInventors: Iqbal Ahmed, Ahmad Moradi-Araghi, Aly-Anis Hamouda, Odd Ivar Eriksen
-
Patent number: 5879852Abstract: 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: GrantFiled: April 30, 1997Date of Patent: March 9, 1999Assignee: AGFA-Gevaert AGInventors: Mathias Eichhorn, Gerhard Buhr
-
Patent number: 5872200Abstract: 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: GrantFiled: July 31, 1997Date of Patent: February 16, 1999Assignee: GenCorp Inc.Inventors: Satish C. Sharma, Charles M. Kausch, Ronald D. Mohan, Raymond J. Weinert
-
Patent number: 5863989Abstract: 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: GrantFiled: April 17, 1997Date of Patent: January 26, 1999Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Koichi Taguchi, Hiroshi Suto
-
Patent number: 5856411Abstract: 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: GrantFiled: June 17, 1996Date of Patent: January 5, 1999Assignee: Samsung Electronics Co., Ltd.Inventors: Sang-jun Choi, Chun-geun Park
-
Patent number: 5844057Abstract: 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: GrantFiled: April 11, 1996Date of Patent: December 1, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Osamu Watanabe, Yoshihumi Takeda, Junji Tsuchiya, Toshinobu Ishihara
-
Patent number: 5811503Abstract: 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: GrantFiled: November 27, 1996Date of Patent: September 22, 1998Assignee: PPG Industries, Inc.Inventors: Robert D. Herold, Randy E. Daughenbaugh, Charles R. Wiedrich
-
Patent number: 5807947Abstract: 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: GrantFiled: July 20, 1994Date of Patent: September 15, 1998Assignee: Clariant Finance (BVI) LimitedInventors: Richard Vicari, Douglas J. Gordon, William D. Hinsberg, Dennis R. McKean, Carlton G. Willson, Ralph Dammel
-
Patent number: 5741873Abstract: 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: GrantFiled: June 27, 1997Date of Patent: April 21, 1998Assignee: Aristech Chemical CorporationInventors: Ronald A. Andrekanic, Joseph Pugach, Thomas W. Smeal
-
Patent number: 5714559Abstract: 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: GrantFiled: December 14, 1995Date of Patent: February 3, 1998Assignee: 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: 5708109Abstract: 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: GrantFiled: February 6, 1997Date of Patent: January 13, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Greggory S. Bennett, Christopher A. Haak
-
Patent number: 5708110Abstract: 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: GrantFiled: February 6, 1997Date of Patent: January 13, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Greggory S. Bennett, Christopher A. Haak
-
Patent number: 5708064Abstract: Organic ophthalmic articles are photochromic and have high indices of refraction.Type: GrantFiled: October 13, 1994Date of Patent: January 13, 1998Assignee: PPG Industries, Inc.Inventors: Charles R. Coleman, Robert D. Herold, Christopher D. Selvig
-
Low yellow index polymer compositions, polymerizable compositions and lenses using said compositions
Patent number: 5702825Abstract: 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: GrantFiled: August 12, 1996Date of Patent: December 30, 1997Assignee: Essilor International (Compagnie Generale d'Optique)Inventors: Gabriel Keita, Joel Renaudineau, Leanirith Yean -
Patent number: 5693732Abstract: 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: GrantFiled: January 8, 1996Date of Patent: December 2, 1997Assignee: GenCorp. Inc.Inventors: Satish C. Sharma, Charles M. Kausch, Ronald D. Mohan, Raymond J. Weinert