CA2214920A1 - Process for producing an oil sorbent copolymer and the product thereof - Google Patents

Process for producing an oil sorbent copolymer and the product thereof

Info

Publication number
CA2214920A1
CA2214920A1 CA002214920A CA2214920A CA2214920A1 CA 2214920 A1 CA2214920 A1 CA 2214920A1 CA 002214920 A CA002214920 A CA 002214920A CA 2214920 A CA2214920 A CA 2214920A CA 2214920 A1 CA2214920 A1 CA 2214920A1
Authority
CA
Canada
Prior art keywords
micro
particle
microporous
droplets
monomers
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002214920A
Other languages
French (fr)
Other versions
CA2214920C (en
Inventor
Milan F. Sojka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Amcol International Corp
Original Assignee
Amcol International Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Amcol International Corp filed Critical Amcol International Corp
Publication of CA2214920A1 publication Critical patent/CA2214920A1/en
Application granted granted Critical
Publication of CA2214920C publication Critical patent/CA2214920C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/04—Polymerisation in solution
    • C08F2/06—Organic solvent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
    • C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/40—Esters of unsaturated alcohols, e.g. allyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/32—Materials not provided for elsewhere for absorbing liquids to remove pollution, e.g. oil, gasoline, fat
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2998—Coated including synthetic resin or polymer

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Public Health (AREA)
  • Materials Engineering (AREA)
  • Environmental & Geological Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

The present invention is directed to a porous copolymer micro-particle having a high oil absorbency. The method of the present invention comprises the steps of:
dissolving at least two polyunsaturated monomers in a water-immiscible organic solvent to provide a monomer mixture containing at least about 60%, preferably about 100% by weight polyunsaturated monomers;
adding the monomer mixture to an aqueous solution, preferably having an effective amount of a suspension stabilizer dissolved therein, to form an organic/aqueous biphasic liquid system;
vigorously agitating the biphasic liquid system at a rate sufficient to cause the water immiscible organic phase to be suspended as micro-droplets in the aqueous phase;
continuing vigorous agitating during polymerization of the monomers in the suspended micro-droplets to produce a microporous polymer micro-particle; and separating the microporous polymer micro-particle from the organic solvent to produce a microporous and oil sorbent polymer micro-particle having a mean unit diameter of less than about 25 microns.
CA002214920A 1997-03-03 1997-09-09 Process for producing an oil sorbent copolymer and the product thereof Expired - Fee Related CA2214920C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/811,129 1997-03-03
US08/811,129 US5712358A (en) 1995-06-07 1997-03-03 Process for producing an oil sorbent copolymer and the product thereof

Publications (2)

Publication Number Publication Date
CA2214920A1 true CA2214920A1 (en) 1998-09-03
CA2214920C CA2214920C (en) 2006-01-03

Family

ID=25205655

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002214920A Expired - Fee Related CA2214920C (en) 1997-03-03 1997-09-09 Process for producing an oil sorbent copolymer and the product thereof

Country Status (6)

Country Link
US (2) US5712358A (en)
EP (1) EP0863160B1 (en)
JP (1) JP4107398B2 (en)
KR (1) KR100490449B1 (en)
CA (1) CA2214920C (en)
DE (1) DE69735226T2 (en)

Families Citing this family (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0558800U (en) * 1992-01-23 1993-08-03 文化シヤッター株式会社 Shutter winding drum structure
US6107429A (en) * 1994-10-24 2000-08-22 Amcol International Corporation Process for producing an oil and water adsorbent polymer capable of entrapping solid particles and liquids and the product thereof
US5863440A (en) 1996-05-24 1999-01-26 Abtech Industries, Inc. Methods for ameliorating oil spills in marine and inland waters
US6344519B1 (en) * 1997-01-10 2002-02-05 Abtech Industries, Inc. Systems for ameliorating aqueous hydrocarbon spills
US6541569B1 (en) 1997-01-10 2003-04-01 Abtech Industries, Inc. Polymer alloys, morphology and materials for environmental remediation
US6099723A (en) 1997-06-06 2000-08-08 Abtech Industries, Inc. Catchbasin systems for filtering hydrocarbon spills
JP4470133B2 (en) 1998-02-18 2010-06-02 アブテック インダストリーズ，インコーポレイテッド Curve-Inlet Storm Drain Systems for filtering waste and hydrocarbons
US6482867B1 (en) * 1998-08-28 2002-11-19 Shiseido Co., Ltd. Polymer packing material for liquid chromatography and a producing method thereof
US6080307A (en) 1998-09-29 2000-06-27 Abtech Industries, Inc. Storm drain systems for filtering trash and hydrocarbons
AU2963400A (en) * 1999-01-14 2000-08-01 Amcol International Corporation Improved controlled release compositions and method
US6491953B1 (en) 2000-01-07 2002-12-10 Amcol International Corporation Controlled release compositions and method
US6531059B1 (en) 2000-10-05 2003-03-11 Abtech Industries, Inc. Suspended runoff water filter
US7319114B2 (en) 2001-03-14 2008-01-15 Sekisui Chemical Co., Ltd. Hollow polymer particles, method for preparing hollow polymer particles, porous ceramic filter, and method for preparing porous ceramic filter
US6673847B2 (en) * 2002-04-01 2004-01-06 Rohm And Haas Company Water immiscible porogen removal process
US20040122385A1 (en) * 2002-12-23 2004-06-24 Kimberly-Clark Worldwide, Inc. Absorbent articles including an odor absorbing and/or odor reducing additive
GB0301577D0 (en) * 2003-01-23 2003-02-26 Edko Pazarlama Tanitim Ltd Sti Topical pharmaceutical and/or cosmetic dispense systems
WO2006041782A1 (en) * 2004-10-07 2006-04-20 Amcol International Corporation Conversion of liquid compositions to a powder
KR100600470B1 (en) * 2004-10-26 2006-07-13 주식회사 선진화학 Preparing method of porous polymethylmethacrlate
US7888306B2 (en) 2007-05-14 2011-02-15 Amcol International Corporation Compositions containing benefit agent composites pre-emulsified using colloidal cationic particles
EP1838393A1 (en) * 2005-01-12 2007-10-03 Amcol International Corporation Detersive compositions containing hydrophobic benefit agents pre-emulsified using colloidal cationic particles
US7871972B2 (en) * 2005-01-12 2011-01-18 Amcol International Corporation Compositions containing benefit agents pre-emulsified using colloidal cationic particles
US7977288B2 (en) * 2005-01-12 2011-07-12 Amcol International Corporation Compositions containing cationically surface-modified microparticulate carrier for benefit agents
CA2598746A1 (en) * 2005-02-25 2007-03-01 Amcol International Corporation Oral care compositions
EP2001434A2 (en) * 2006-04-04 2008-12-17 Amcol International Corporation Cosmetic and therapeutic stick products
DK2012745T3 (en) * 2006-05-01 2011-01-17 Colgate Palmolive Co Oral care composition with silicone composite
WO2008060778A2 (en) * 2006-10-05 2008-05-22 Amcol International Corporation Compositions having a performance indicator
US20080152894A1 (en) * 2006-12-20 2008-06-26 Amcol Health & Beauty Solutions Treated substrates having improved delivery of impregnated ingredients
KR100725240B1 (en) * 2007-01-31 2007-06-04 한국스미더스 오아시스 주식회사 The product method and foaming matter to absorb oil
CN101677934A (en) * 2007-03-21 2010-03-24 陶氏环球技术公司 Hair care composition
EP2164446A4 (en) * 2007-07-12 2015-08-05 Amcol International Corp High-foaming cleanser composition with a skin care agent
WO2009100464A1 (en) 2008-02-08 2009-08-13 Amcol International Corporation Compositions containing cationically surface-modified microparticulate carrier for benefit agents
US8188022B2 (en) 2008-04-11 2012-05-29 Amcol International Corporation Multilayer fragrance encapsulation comprising kappa carrageenan
EP2268782A2 (en) 2008-04-11 2011-01-05 Amcol International Corporation Multilayer fragrance encapsulation
EP2334286A1 (en) * 2008-09-12 2011-06-22 Amcol International Corporation Low ph retinoid topical compositions
US20120014888A1 (en) * 2009-01-29 2012-01-19 Amcol International Corporation Matte Skin Finish Compositions
WO2012161878A1 (en) * 2011-05-20 2012-11-29 Exxonmobil Upstream Research Company Oil spill treatment compositions, methods of manufacture, and methods of use
WO2013003686A1 (en) 2011-06-30 2013-01-03 The Procter & Gamble Company Absorbent structure comprising an oil-scavenger component
CN104093754B (en) * 2011-11-21 2017-06-23 3M创新有限公司 For storing and deliver the polymer particle of activating agent
US20150050227A1 (en) 2012-03-02 2015-02-19 Amcol International Corporation Compositions Having Perspiration Reduction Properties
JP2013249437A (en) * 2012-06-04 2013-12-12 Hitachi Chemical Co Ltd Method of manufacturing polymer using mixed solvent of water and water-insoluble organic solvent, and polymer manufactured by the manufacturing method
WO2014156994A1 (en) 2013-03-29 2014-10-02 積水化成品工業株式会社 Porous resin particle, method for producing same, dispersion, and application thereof
US9474720B2 (en) 2013-11-04 2016-10-25 BioPharmX, Inc. Dosage form comprising an active ingredient and a plurality of solid porous microcarriers
DE102015113522A1 (en) * 2015-08-17 2017-02-23 Universität Stuttgart Porous monolithic hybrid reactor, a process for its preparation and its use
US10953352B2 (en) 2017-05-19 2021-03-23 Baleen Process Solutions Fluid treatment system and method of use utilizing a membrane
JP2021031659A (en) * 2019-08-29 2021-03-01 Ｅｎｅｏｓ株式会社 Crosslinking-type methacrylate resin particle and pore-forming agent
CN114733498B (en) * 2022-05-17 2023-08-22 常州大学 Preparation method of polydimethylsiloxane/ethylcellulose sponge body with organic solvent as template

Family Cites Families (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB967051A (en) * 1963-01-14 1964-08-19 Du Pont Microgels and coating compositions containing same
US3658772A (en) * 1966-10-20 1972-04-25 Dow Chemical Co Acrylic acid polymers
US3493500A (en) * 1966-10-20 1970-02-03 Dow Chemical Co Acrylic acid polymers
DE2059484C3 (en) * 1970-12-03 1974-03-07 Basf Ag, 6700 Ludwigshafen Process for the production of insoluble, only slightly swellable poly-N-vinylpyrrolidone ^)
US3966902A (en) * 1972-05-12 1976-06-29 Airwick Industries, Inc. Polymer complex carriers for an active ingredient
GB1443715A (en) * 1973-06-28 1976-07-21 Kansai Paint Co Ltd Vinylurethanes
CH606154A5 (en) * 1974-07-02 1978-11-15 Goodrich Co B F
DE2437640C3 (en) * 1974-08-05 1978-06-15 Basf Ag, 6700 Ludwigshafen Process for the preparation of insoluble polymers of N-vinyllactams which are only slightly swellable in water
DE2437629C3 (en) * 1974-08-05 1978-09-21 Basf Ag, 6700 Ludwigshafen Process for the preparation of insoluble polymers of N-vinyllactams which are only slightly swellable in water
US4136250A (en) * 1977-07-20 1979-01-23 Ciba-Geigy Corporation Polysiloxane hydrogels
US4224427A (en) * 1978-06-01 1980-09-23 Ciba-Geigy Corporation Process for preparing hydrogels as spherical beads of large size
US4250322A (en) * 1979-08-10 1981-02-10 Altshuler Judif M Oligourethanacrylates and methods for their manufacture
US4276402A (en) * 1979-09-13 1981-06-30 Bausch & Lomb Incorporated Polysiloxane/acrylic acid/polcyclic esters of methacrylic acid polymer contact lens
US5348621A (en) * 1979-11-01 1994-09-20 Coalition Technologies, Limited Low bulk and light-weight products
US4423099A (en) * 1980-07-28 1983-12-27 Ciba-Geigy Corporation Membrane modified hydrogels
GB2090264B (en) * 1980-12-30 1984-10-17 Nat Res Dev Polymerisation process
US4374126A (en) * 1981-02-23 1983-02-15 Warner-Lambert Company Film forming antimicrobial material
US4341889A (en) * 1981-02-26 1982-07-27 Bausch & Lomb Incorporated Polysiloxane composition and biomedical devices
US4724240A (en) * 1981-03-23 1988-02-09 Wickhen Products, Inc. Lattice-entrapped emollient-moisturizer composition
US4414278A (en) * 1982-04-22 1983-11-08 E. I. Du Pont De Nemours And Company Crosslinked triacrylate polymer beads
US4543398A (en) * 1983-04-28 1985-09-24 Minnesota Mining And Manufacturing Company Ophthalmic devices fabricated from urethane acrylates of polysiloxane alcohols
US4509949A (en) * 1983-06-13 1985-04-09 The B. F. Goodrich Company Water thickening agents consisting of copolymers of crosslinked acrylic acids and esters
US5206159A (en) * 1984-11-01 1993-04-27 Miles Inc., As Legal Successor By Merger With Technicon Instruments Corp. Polymer particles containing colloidal iron oxide granules for use as a magnetically responsive reagent carrier
DE3688988T3 (en) * 1985-06-17 1998-12-10 Ppg Industries Inc Acrylic polymer and manufacturing process.
CA1281492C (en) * 1985-10-23 1991-03-12 Joseph Albert Antonelli Crosslinked polymer microparticle
US5145675A (en) * 1986-03-31 1992-09-08 Advanced Polymer Systems, Inc. Two step method for preparation of controlled release formulations
US4709767A (en) * 1986-01-06 1987-12-01 American Colloid Company Production process for manufacturing low molecular weight water soluble acrylic polymers as drilling fluid additives
US4794140A (en) * 1986-01-06 1988-12-27 American Colloid Company Production process for manufacturing low molecular weight water soluble acrylic polymers as drilling fluid additives
US4675426A (en) * 1986-06-11 1987-06-23 General Electric Company Free-radical, initiators, curable compositions, and methods
US4920187A (en) * 1987-01-12 1990-04-24 Nippon Paint Co., Ltd. Process for preparing particles having monodisperse particle size
EP0301532A3 (en) * 1987-07-30 1989-10-18 The B.F. Goodrich Company Solvent free acrylic acid type thickening agents and a method of making same
US4873091A (en) * 1988-05-23 1989-10-10 Advanced Polymer Systems, Inc. Controlled release formulating employing resilient microbeads
CA2003808C (en) * 1988-11-28 1999-11-09 Eugene Joseph Sehm Crosslinked polyacrylic acid
US5510117A (en) * 1989-03-09 1996-04-23 Micro-Pak, Inc. Entrapment vehicle and method
US5135989A (en) * 1989-04-07 1992-08-04 Dow Corning Corporation Method of making hydrophobic copolymers hydrophilic
CA2013023A1 (en) * 1989-04-17 1990-10-17 Milan F. Sojka Method of making highly adsorptive copolymers
US5209932A (en) * 1989-05-30 1993-05-11 Moleculon, Inc. Foot care compositions
US5223267A (en) * 1989-05-30 1993-06-29 Purepac, Inc. Analgesic compositions
US5223251A (en) * 1989-05-30 1993-06-29 Purepac, Inc. Skin fragrance compositions
US4962170A (en) * 1989-08-31 1990-10-09 Dow Corning Corporation Method of making highly absorptive polymers
US4962133A (en) * 1989-09-05 1990-10-09 Dow Corning Corporation Method of making highly adsorptive copolymers
US5320835A (en) * 1989-10-25 1994-06-14 Avon Products, Inc. Cosmetic formulation having a palette of color shades renewable by mechanical action
KR920702928A (en) * 1989-11-09 1992-12-17 원본미기재 Oral-delivery composition to which flavor is added, and preparation method thereof
US5208038A (en) * 1989-12-08 1993-05-04 Dow Corning Corporation Coacervated highly absorptive polymers
US5422361A (en) * 1989-12-20 1995-06-06 Schering Corporation Stable cream and lotion bases for lipophilic drug compositions
US5189102A (en) * 1990-01-30 1993-02-23 Ricoh Company, Ltd. Method for producing a vinyl resin using a silicon oil solvent
US5147937A (en) * 1990-03-22 1992-09-15 Rohm And Haas Company Process for making controlled, uniform-sized particles in the 1 to 50 micrometer range
US5300565A (en) * 1990-04-02 1994-04-05 The Procter & Gamble Company Particulate, absorbent, polymeric compositions containing interparticle crosslinked aggregates
US5246972A (en) * 1990-04-06 1993-09-21 Dow Corning Corporation Polish containing highly adsorptive polymer
US5292835A (en) * 1990-05-16 1994-03-08 Basf Aktiengesellschaft Microcapsules
JP3286315B2 (en) * 1990-06-20 2002-05-27 アドバンスト ポリマー システムズ，インコーポレイティド Compositions and methods for controlled release of soluble actives
DE69116989D1 (en) * 1990-06-28 1996-03-21 Edko Trading Representation Multi-phase pharmaceutical compositions
US5130343A (en) * 1991-03-13 1992-07-14 Cornell Research Foundation, Inc. Process for producing uniform macroporous polymer beads
US5145685A (en) * 1991-04-08 1992-09-08 Dow Corning Corporation Skin treatment method and composition
JPH05140236A (en) * 1991-06-24 1993-06-08 Tokyo Keikaku:Kk Fine porous water-absorbent resin particle as additive
US5158772A (en) * 1991-09-23 1992-10-27 Davis Walter B Unique bacterial polysaccharide polymer gel in cosmetics, pharmaceuticals and foods
JPH05105729A (en) * 1991-10-08 1993-04-27 Tokyo Keikaku:Kk Oil-absorbing resin
US5261169A (en) * 1991-10-11 1993-11-16 Advanced Polymer Systems, Inc. System and method for deodorant delivery in footwear
DE69317154T2 (en) * 1992-05-29 1998-11-12 Rohm & Haas Process for the preparation of cross-linked copolymers of methacrylic anhydride
US5288814A (en) * 1992-08-26 1994-02-22 The B. F. Goodrich Company Easy to disperse polycarboxylic acid thickeners
US5238736A (en) * 1992-09-18 1993-08-24 Minnesota Mining And Manufacturing Company Polymeric microspheres for low-friction surfaces
US5498678A (en) * 1992-12-21 1996-03-12 Rohm And Haas Company Suspension polymerization process for water-soluble monomers
US5336740A (en) * 1993-11-12 1994-08-09 Minnesota Mining And Manufacturing Company Method for preparing poly(vinyl trifluoroacetate) and poly(vinyl trifluoroacetate/vinyl ester) in the absence of chlorofluorocarbon solvent
US5460725A (en) * 1994-06-21 1995-10-24 The Dow Chemical Company Polymeric adsorbents with enhanced adsorption capacity and kinetics and a process for their manufacture
US5677407A (en) * 1995-06-07 1997-10-14 Amcol International Corporation Process for producing an oil sorbent polymer and the product thereof
JPH09202213A (en) * 1996-01-24 1997-08-05 Nippon Seiko Kk Retractor with pretensioner for seat belt

Also Published As

Publication number Publication date
JP4107398B2 (en) 2008-06-25
DE69735226D1 (en) 2006-04-20
EP0863160B1 (en) 2006-02-08
US5834577A (en) 1998-11-10
DE69735226T2 (en) 2006-11-02
CA2214920C (en) 2006-01-03
EP0863160A2 (en) 1998-09-09
JPH10244152A (en) 1998-09-14
KR19980079388A (en) 1998-11-25
KR100490449B1 (en) 2005-10-19
US5712358A (en) 1998-01-27
EP0863160A3 (en) 2000-04-19

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