US20040116305A1 - Low friction hydrogel having straight chain polymers and method for preparation thereof - Google Patents

Low friction hydrogel having straight chain polymers and method for preparation thereof Download PDF

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US20040116305A1
US20040116305A1 US10/466,895 US46689503A US2004116305A1 US 20040116305 A1 US20040116305 A1 US 20040116305A1 US 46689503 A US46689503 A US 46689503A US 2004116305 A1 US2004116305 A1 US 2004116305A1
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gel
polymer
linear chain
low friction
chain polymer
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Yoshihito Osada
Jian Gong
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Hokkaido Technology Licensing Office Co Ltd
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Publication of US20040116305A1 publication Critical patent/US20040116305A1/en
Assigned to HOKKAIDO TECHNOLOGY LICENSING OFFICE CO., LTD. reassignment HOKKAIDO TECHNOLOGY LICENSING OFFICE CO., LTD. CORRECTIVE TO CORRECT THE ASSIGNEE'S ADDRESS ON A DOCUMENT PREVIOUSLY RECORDED AT REEL 014989, FRAME 0457. (ASSIGNMENT OF ASSIGNOR'S INTEREST) Assignors: GONG, JIAN PING, OSADA, YOSHITO
Assigned to HOKKAIDO TECHNOLOGY LICENSING OFFICE CO. reassignment HOKKAIDO TECHNOLOGY LICENSING OFFICE CO. CORRECTED COVER SHEET TO CORRECT ASSIGNOR'S NAME, PREVIOUSLY RECORDED AT REEL/FRAME 016638/0470 (ASSIGNMENT OF ASSIGNOR'S INTEREST) Assignors: GONG, JIAN PING, OSADA, YOSHIHITO
Assigned to HOKKAIDO TECHNOLOGY LICENSING OFFICE CO., LTD. reassignment HOKKAIDO TECHNOLOGY LICENSING OFFICE CO., LTD. RECORD TO CORRECT THE RECEIVING PARTY'S NAME, PREVIOUSLY RECORDED AT REEL 017239 FRAME 0412. Assignors: GONG, JIAN PING, OSADA, YOSHIHITO
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    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/10—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of amides or imides
    • 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
    • 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
    • C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
    • 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
    • C08F261/00—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00
    • C08F261/02—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols
    • C08F261/04—Macromolecular compounds obtained by polymerising monomers on to polymers of oxygen-containing monomers as defined in group C08F16/00 on to polymers of unsaturated alcohols on to polymers of vinyl alcohol
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • 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
    • C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00

Definitions

  • the invention relates to a low friction hydrogel having linear chain polymer and a method for preparation thereof.
  • JP, A, 10-500038 is described a hardening material containing a polymer matrix such as silicon polymer and a hydrogel, which is used for healing on an injury site such as the joint and for a surface finish.
  • the hydrogel consists of a hydrophilic and water-insoluble polymer and reduces a surface friction force.
  • JP, A, 8-19599 is described a medical device having in the surface a layer to form a hydrogel when swollen, which consists of a water-soluble and water-swollen polymer having a reactive functional group and of an antithrombotic drug.
  • the hydrogel layer which is fixed on the surface of a medical device such as catheter, becomes a lubrication layer and reduces the friction.
  • JP JP, A, 6-71818 is described a underwater clothing small in a frictional resistance toward water, which uses a composite sheet consisting of a fiber base and a resin membrane containing a water-soluble alginate.
  • the problem of the invention is to provide a further low friction material to satisfy the above requirements.
  • the invention relates to a low friction hydrogel, wherein a linear chain polymer is admixed with or graft-polymerized to a polymer gel.
  • the invention also relates to the above low friction hydrogel wherein the linear chain polymer is graft-polymerized on a surface of the polymer gel.
  • the invention relates to the above low friction hydrogel, wherein monomers constituting the polymer gel and monomers constituting the linear chain polymer are the same kind of monomers.
  • the invention also relates to the above low friction hydrogel, wherein the frictional coefficient is not more than 0.01.
  • the invention relates to the above low friction hydrogel, wherein the content ratio of the linear chain polymer relative to the total weight of the low friction hydrogel is 2-300 wt. %.
  • the invention also relates to the above low friction hydrogel, wherein the polymer gel is an ionic gel.
  • the invention relates to use of the above low friction hydrogel on surfaces of a solid and a biological tissue.
  • the invention also relates to a method for preparing the low friction hydrogel, wherein the linear chain polymer or monomers forming the linear chain polymer is admixed with and/or graft-polymerized to a polymer gel or monomers forming the polymer gel.
  • the invention relates to the above method, wherein the linear chain polymer is admixed with and then graft-polymerized to the polymer gel.
  • the invention also relates to the above method wherein one or more species of monomers to form the linear chain polymer are admixed with and polymerized to the polymer gel, so as to involve the linear chain polymer into the polymer gel.
  • the invention relates to the above method, wherein the linear chain polymer are admixed with and polymerized with one or more species of monomers forming the polymer gel, so as to involve the linear chain polymer into the polymer gel.
  • the invention also relates to the above method wherein one or more species of monomers forming the polymer gel and one or more species of monomers forming the linear chain polymer are admixed and polymerized, so as to graft the linear chain polymer to the polymer gel.
  • the invention relates to the above low friction hydrogel, wherein monomers forming the polymer gel and monomers forming the linear chain polymer are the same type of monomers.
  • the invention also relates to the method for preparing the low friction hydrogel, wherein monomers forming the polymer gel are polymerized on a hydrophobic substrate.
  • FIG. 1 shows the results on the rate of rotation dependency of the friction force of 2-acrylamido-2-methylpropanesulfonic acid (AMPS) gel against a glass plate.
  • AMPS 2-acrylamido-2-methylpropanesulfonic acid
  • FIG. 2 shows the results on the load dependency of the friction force of AMPS gel when the velocity is 0.01 rad/s.
  • FIG. 3 shows the results on the frictional coefficient of dimethyl acrylamide (DAMM) gel, AMPS gel and poly(vinyl alcohol) (PVA) gel against a glass plate.
  • DAMM dimethyl acrylamide
  • AMPS AMPS gel
  • PVA poly(vinyl alcohol)
  • FIG. 4 shows the results on the frictional coefficient of DAMM gel and AMPS gel against a glass plate
  • the monomers constituting the polymer gels used in the invention are not limited if they are monomers forming hydrogels with three-dimensional network atructure, typically illustrative are acrylic acid or methacrylic acid and a derivative thereof, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, acrylamide or methacrylamide and a derivative thereof, stylene sulfonic acid, vinyl sulfonic acid, vinyl phosphoric acid, vinylpyridine, trimethylvinylpyridinium chloride, 3-acryloylaminopropyltrimethylammonium chloride, 3-dimethylmethacryloyloxyethylammonium propanesulfonic acid and the like.
  • Preferable are acrylamide, 2-acrylamide-2-methylpropanesulfonic acid, acrylic acid, stylene sulfonic acid, etc.
  • a crosslinking agent to crosslink these monomers is N,N′-methylenebisacrylamide, ethyleneglycol dimethacrylate, divinylbenzene or the like.
  • any two or three components of the monomers described above can be used, though the same species of monomers as the monomers constituting the above polymer gels can also be used.
  • polysaccharide gels such as gellan gel, kappa-carrageenan gel, agarose gel, carboxymethyl cellulose gel or the like, protein gels such as gelatin, collagen or the like, nucleic acid gels such as DNA, RNA or the like, and polymer gels such as polyvinyl alcohol, polyglutamic acid, polyethylene imine, frozen-thawed gel or the like.
  • the content ratio of the linear chain polymer relative to the total weight of the low friction hydrogel is preferably 2-300 wt. %., especially 5-100 wt. % from a viewpoint of the reduction effect of the friction force.
  • the low friction hydrogels of the invention include (1) the low friction hydrogels in which the linear chain polymer is admixed with the polymer gel, or (2) the low friction hydrogels in which the linear chain polymer is graft-polymerized to the polymer gel.
  • any method may be used if it is a method in which the linear chain polymer can be admixed with the polymer gel, though typically, the following methods are illustrated.
  • the linear chain polymer is physically admixed with the polymer gel.
  • the polymer gel After forming the polymer gel, the polymer gel is fully immersed in a monomer solution forming the linear chain polymer, and the monomers are dispersed in the gel, followed by polymerization of the monomers.
  • the linear chain polymer is admixed with a material such as monomers and the gel is formed by pollymerization.
  • any method may be used if it is a method in which the linear chain polymer can be graft-polymerized to the polymer gel, though typically, the following methods are illustrated.
  • the linear chain polymer is admixed with a formed polymer gel, followed by graft-polymerization.
  • One or more species of monomers forming the polymer gel and one or more species of monomers forming the linear chain polymer are admixed and polymerized, so as to graft the linear chain polymer to the polymer gel.
  • the above f method is a novel gel synthetic method which the inventors have developed originally (refer to J. Phys. Chem. B, 103,6069-6074(1999), Biomacromolecules, 1, 162-167(2000), Proceeding of The Society of Polymer Science, Vol.48, No. 10, 2603-2604(1999), Proceeding of The Society of Polymer Science, Vol.49, No. 12, 3689-3692(2000).
  • a hydrophobic substrate such as Teflon plate, polypropylene, polyethylene, polystylene, or the like produces a concentration gradient of a hydrophilic monomer solution near the hydrophobic substrate, and a crosslinking density becomes low, resulting to form gels having graft chains on the surface.
  • This method is one step, does not need to use other reagents or the like, and is particularly preferable since a desired gel may simply be formed by the hydrophobic substrate only
  • the polymer gel having the linear chain polymer which is obtained by the above each method, contains the hydrophilic polymer chains in the gel or on the surface, a water content of the gel is further increased, and the hydrated gel or the polymer chains hydrated on the surface work as a lubricious layer at the interface of solids, enabling to obtain a low friction polymer hydrogel.
  • a low friction hydrogel which is an ionic gel
  • an electrostatic repulsion force is produced, enabling to obtain the best friction effect due to the formation of a further thick water layer at a friction interface compared with a neutral gel.
  • the hydrogels of the invention preferably contain a plenty of water in order to obtain an enough low friction effect.
  • the water content is preferably not less than 50 wt. %, in particular preferably not less than 100 wt. %.
  • the frictional coefficient of the obtained hydrogels is also preferably not more than 0.01, in particular preferably not more than 0.005.
  • the form of the hydrogels of the invention may be either form if it is a form to contain the linear chain polymer chains in the polymer gels or on the polymer gel surfaces.
  • one having the linear chain polymer on the gel surface is preferable, further, one to which the polymer chains are graft-polymerized on the surface is preferable.
  • Methylenebisacrylamide 8% as a crosslinking agent, alpha-ketoglutaric acid 0.1% as a photosensitizer, and 4 g of poly(AMPS) of molecular weight 250,000 synthesized in advance were added to an aqueous solution (AMPS) 100 ml containing 2-acrylamido-2-methylpropanesulfonic acid 20 g, followed by carrying out 400 W UV irradiation to prepare AMPS gel containing the linear chain polymer on a glass plate.
  • AMPS aqueous solution
  • PAMPS gel containing no linear chain polymer was prepared in the same way as that in the example 1.
  • DMAA gel containing a linear chain polymer was synthesized in the same way as that in the example 1.
  • DMAA gel containing no linear chain polymer was prepared in the same way as that in the example 3.
  • Methylenebisacrylamide 0.5 g as a crosslinking agent, and alpha-ketoglutaric acid 0.1 g as a photosensitizer were added to an aqueous solution 100 ml containing AMPS 10 g, followed by carrying out 400 W UV irradiation to prepare AMPS gel on a glass plate.
  • the obtained gel was immersed in an aqueous solution 100 ml containing AMPS monomer 4 g for 1 week to disperse the monomer into an inner part, followed by 400 W UV irradiation to polymerize the polymer in the inner part, thereby preparing a gel containing linear chain polymer chains.
  • FIG. 2 shows the results in which a load dependency of the friction force measured fixing the velocity at 0.01 rad/s.
  • the gel containing the linear chain polymer and the gel having graft chains on the surface both become small in the friction force by not less than one place.
  • the effect was remarkable in the low loading area, demonstrating reduction of the friction force in not less than two places.
  • Methylenebisacrylamide 1 wt. % as a crosslinking agent, and alpha-ketoglutaric acid 0.5 wt. % as a photosensitizer were added to an aqueous solution 50 ml containing DMAA 7 g, followed by carrying out 200 W UV irradiation to prepare DMAA gel on a glass plate.
  • AMPS gel was prepared in a similar method.
  • an aqueous solution 100 ml containing ethyleneglycol glycidyl ether 2 g and polyvinyl alcohol 10 g was reacted at 80° C. for 24 hours, carrying out crosslinking to prepare polyvinyl alcohol (PVA) gel.
  • PVA polyvinyl alcohol
  • FIG. 3 shows the frictional coefficient for each gel measured.
  • the upper figure are the results of the gels in which poly(DMAA) or poly(AMPS) was allowed to be contained in DMAA gel, and the lower figure are the results of the gels in which poly(AMPS) was allowed to be contained in polyvinyl alcohol (PVA) gel or AMPS gel.
  • PVA polyvinyl alcohol
  • FIG. 4 shows the frictional coefficient for each gel measured.
  • DMAA shows the gel polymerized by sandwiching between glass plates
  • DMAA graft does the gel polymerized by sandwiching between Teflon plates and having graft chains on the surface
  • PAMPS does APMS gel polymerized by sandwiching between glass plates
  • PAMPS graft does APMS gel polymerized by sandwiching between Teflon plates and having graft chains on the surface.
  • a low friction material in a degree which has not been found as yet can be prepared.
US10/466,895 2001-01-22 2001-09-07 Low friction hydrogel having straight chain polymers and method for preparation thereof Abandoned US20040116305A1 (en)

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JP2001-013617 2001-01-22
JP2001013617A JP5048183B2 (ja) 2001-01-22 2001-01-22 直鎖状高分子を有する低摩擦ハイドロゲルおよびその製造方法
PCT/JP2001/007776 WO2002057368A1 (fr) 2001-01-22 2001-09-07 Hydrogel a faible frottement presentant un polymere a chaine droite et son procede de preparation

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US20070272040A1 (en) * 2004-09-09 2007-11-29 Takaharu Okajima Device and Method for Measuring Molecule Using Gel Substrate Material
US20090130755A1 (en) * 2007-11-16 2009-05-21 Michael Detamore Hydrogel networks having living cells encapsulated therein
WO2012054107A1 (en) * 2010-07-09 2012-04-26 Lubrizol Advanced Materials, Inc. Blends of acrylic copolymer thickeners
WO2015002888A1 (en) * 2013-07-01 2015-01-08 Trustees Of Boston University Dissolvable hydrogel compositions for wound management and methods of use
US10982054B2 (en) 2014-12-26 2021-04-20 Samsung Electronics Co., Ltd. Polymer gel and preparation method therefor
CN114787248A (zh) * 2019-09-30 2022-07-22 日清纺控股株式会社 复合材料
EP4361183A1 (en) * 2022-10-18 2024-05-01 SNF Group High molecular weight anionic polyacrylamides

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AU2002309026A1 (en) 2002-05-01 2003-11-17 Hokkaido Technology Licensing Office Co., Ltd. Gel having multiple network structure and method for preparation thereof
AU2002323923A1 (en) * 2002-08-08 2004-02-25 Hokkaido Technology Licensing Office Co., Ltd. Low friction organogel
WO2006013612A1 (ja) 2004-06-18 2006-02-09 Hokkaido Technology Licensing Office Co., Ltd. 人工半月板
JP5059407B2 (ja) * 2004-06-25 2012-10-24 国立大学法人北海道大学 ゲル、その製造方法、吸水性樹脂、潤滑材及び細胞培養用基材
JP5324070B2 (ja) 2007-08-27 2013-10-23 スリーエム イノベイティブ プロパティズ カンパニー 高分子ゲル構造体及びその製造方法
JP5850417B2 (ja) * 2010-08-04 2016-02-03 国立大学法人北海道大学 高分子ゲル及びその製造方法

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US8715983B2 (en) 2007-11-16 2014-05-06 University Of Kansas Hudrogel network comprising thermally gelling polysaccharide or protein gel encapsulating living cells
US20090130755A1 (en) * 2007-11-16 2009-05-21 Michael Detamore Hydrogel networks having living cells encapsulated therein
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WO2012054107A1 (en) * 2010-07-09 2012-04-26 Lubrizol Advanced Materials, Inc. Blends of acrylic copolymer thickeners
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WO2015002888A1 (en) * 2013-07-01 2015-01-08 Trustees Of Boston University Dissolvable hydrogel compositions for wound management and methods of use
US9993577B2 (en) 2013-07-01 2018-06-12 Trustees Of Boston University Dissolvable hydrogel compositions for wound management and methods of use
US10646614B2 (en) 2013-07-01 2020-05-12 Trustees Of Boston University Dissolvable hydrogel compositions for wound management and methods of use
US10982054B2 (en) 2014-12-26 2021-04-20 Samsung Electronics Co., Ltd. Polymer gel and preparation method therefor
CN114787248A (zh) * 2019-09-30 2022-07-22 日清纺控股株式会社 复合材料
EP4361183A1 (en) * 2022-10-18 2024-05-01 SNF Group High molecular weight anionic polyacrylamides

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JP5048183B2 (ja) 2012-10-17
JP2002212452A (ja) 2002-07-31

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