WO2001021721A1 - Materiau de revetement pour objet moule revetu realise par moulage au trempe - Google Patents

Materiau de revetement pour objet moule revetu realise par moulage au trempe Download PDF

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Publication number
WO2001021721A1
WO2001021721A1 PCT/JP2000/006392 JP0006392W WO0121721A1 WO 2001021721 A1 WO2001021721 A1 WO 2001021721A1 JP 0006392 W JP0006392 W JP 0006392W WO 0121721 A1 WO0121721 A1 WO 0121721A1
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WIPO (PCT)
Prior art keywords
parts
coating agent
coating
polyurethane
chain
Prior art date
Application number
PCT/JP2000/006392
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English (en)
Japanese (ja)
Inventor
Tutomu Tawa
Chikako Koda
Hiroyuki Shiraki
Tamio Fukuda
Shouji Tamura
Original Assignee
Takeda Chemical Industries, Ltd.
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 Takeda Chemical Industries, Ltd. filed Critical Takeda Chemical Industries, Ltd.
Priority to AU73164/00A priority Critical patent/AU7316400A/en
Publication of WO2001021721A1 publication Critical patent/WO2001021721A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers

Definitions

  • the present invention relates to a nonionic water-based polyurethane coating agent for coating a so-called dip-formed product such as a rubber glove and a finger cot. More specifically, a coating agent for coating a dip molded product comprising a nonionic polyurethane resin dispersed or dissolved in water and containing a polyoxyethylene chain in an amount of 3 to 60% by weight based on the solid content, and a coating agent for coating the same. It relates to a dip molded product coated with a coating agent.
  • a method of spraying a powdery lubricant such as talc or starch on a dip molded product is generally employed.
  • the splattered lubricants can damage the respiratory system of workers.
  • the lubricant may fall from the glove to the patient's wound, causing granulation to form.
  • this branching technique also suffers from the problem of water resistance of the coated layer and the stability of the aqueous polyurethane dispersion, which is thought to be due to the reaction of metal ions such as Ca derived from the salt coagulation solution used in the production with the ionic polyurethane. There is a problem such as a decrease in performance.
  • the present invention relates to an aqueous polyurethane coating agent for coating a dip molded product for obtaining a dip molded product which is easily removable without using a lubricant such as talc or starch, and a dip molded product coated with the coating agent.
  • a coating liquid for coating a dip molded product that does not solidify due to metal ions in a salt coagulation solution contained in the molded product in a coating process of the dip molded product, and thus can withstand long-term use. It is in. Disclosure of the invention
  • a nonionic polyurethane resin is dispersed or dissolved in water, and a polyxylene chain is obtained. Is stable over a long period of time without being affected by metal ions such as calcium ions contained in the coagulating liquid used in the dip molded product manufacturing process. It was found that the adhesion to the surface was also very good.
  • the nonionic polyurethane resin has a polyoxytetralamethylene chain in the main chain of the molecule
  • the obtained coating has good slipperiness to the hand, is easy to attach and detach, and has a polyoxyethylene chain as a side chain.
  • the coating at the end had excellent water resistance.
  • the present invention (1) a coating agent for coating a dip molded product obtained by dispersing or dissolving a nonionic polyurethane resin in water and containing 3 to 60% by weight of a polyoxyethylene chain based on a solid content;
  • the dip molded product coated with the coating agent of the present invention is obtained by immersing a mold in rubber latex and drying. Therefore, a method for producing a dip molded product will be described.
  • a mold made of ceramic or the like is immersed in a salt coagulation solution for rubber latex such as an aqueous solution of calcium nitrate, pulled up and dried.
  • a salt coagulation solution for rubber latex such as an aqueous solution of calcium nitrate
  • the mold to which the salt coagulation liquid has adhered is immersed in rubber latex.
  • rubber latex natural rubber or synthetic rubber is used.
  • the dip molded product thus obtained is immersed in the coating agent of the present invention before or after demolding, and dried to obtain a dip molded product coated with a polyurethane resin.
  • the dip molded product is vulcanized to improve its physical properties, and the vulcanization may be before or after coating with the polyurethane resin.
  • the coating agent of the present invention is used as an aqueous dispersion or solution containing usually 1 to 20% by weight, preferably 2 to 10% by weight, more preferably 3 to 6% by weight of solids. It is.
  • the thickness of the film formed on the dip-formed product by this coating agent is usually 50 m or less, preferably 0.5 to 20 m, more preferably 1 to 5 tm.
  • the coating agent of the present invention will be described.
  • the coating agent of the present invention can be produced by a known technique.
  • a compound having at least two active hydrogen groups per molecule and a compound having at least two isocyanate groups per molecule are reacted in one or more stages and dissolved or dispersed in water.
  • Examples of the compound having at least two active hydrogen groups per molecule include, for example, compounds having an active hydrogen, such as an amino group, a hydroxyl group, and a mercapto group.
  • the reaction rate with the isocyanate group Considering the later mechanical properties, compounds having a hydroxyl group are preferred.
  • the number of functional groups of the compound having an active hydrogen group is preferably 2 to 6, and particularly preferably 2 to 4, from the viewpoint of maintaining good mechanical properties of the coating film.
  • the molecular weight of the compound having an active hydrogen group is preferably from 200 to 100,000 from the viewpoint of the urethane bond concentration that gives the final coating film performance and the workability during production. 00-5, 000 is particularly preferred.
  • Examples of the compound in which the active hydrogen group is a hydroxyl group include, for example, polyester polyol, polyether polyol, polyether ester polyol, polyester amide polyol, acrylic polyol, polycarbonate polyol, polyhydroxyalkane, castor oil, polyurethane polyol, or a mixture thereof. No.
  • polyester polyols include, for example, dibasic acids such as terephthalic acid, isophthalic acid, adipic acid, azelaic acid, and sebacic acid, and their alkyl esters or mixtures thereof, and, for example, ethylene glycol, propylene glycol, diethylene glycol, Butylene glycol, neopentyl glycol, 1,6-hexane glycol, 3-methyl-1,5-pentanediol, 3,3'-dimethylolheptane, polyxylene glycol, polyoxypropylene glycol Polyesters obtained by reacting glycols or mixtures thereof with glycols such as polyoxytetramethylene glycol or the like, for example, polycaprolactone, polyvalerolactone, poly (/ 3-methyl-a-valerolactone) and the like. And polyester polyols obtained by ring-opening polymerization of lactones.
  • dibasic acids such as terephthalic acid, iso
  • polyether polyols include, for example, water, ethylene glycol, propylene glycol, trimethylolpropane, glycerin and other low molecular weight polyols used as initiators, for example, ethylene oxide, propylene oxide, and butylene oxide.
  • polyether ester polyol examples include, for example, a reaction between a dibasic acid such as terephthalic acid, isophthalic acid, adipic acid, azelaic acid, sebacic acid, or a dialkyl ester thereof, or a mixture thereof, and the above polyether polyol. And a polyetherester polyol obtained by the reaction.
  • a dibasic acid such as terephthalic acid, isophthalic acid, adipic acid, azelaic acid, sebacic acid, or a dialkyl ester thereof, or a mixture thereof
  • a polyetherester polyol obtained by the reaction.
  • polyesteramide polyol in the polyesterification reaction, for example, an aliphatic diamine having an amino group such as ethylenediamine, propylenediamine, hexamethylenediamine or the like is used as a raw material, And the like, which are obtained by reacting additionally.
  • acryl polyol examples include polymerizable monomers having one or more hydroxyl groups in one molecule, such as hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, and the corresponding methacrylic acid derivatives. And, for example, those obtained by copolymerizing acrylic acid, methacrylic acid or esters thereof.
  • polycarbonate polyols include, for example, ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and 9-nonane Or 1,8-nonanediol, neopentyl glycol, diethylene glycol, dipropylene glycol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, bisphenol-A, or one selected from the group consisting of Two or more glycols and dimethyl carbonate, diphenyl carbonate, ethylene Examples thereof include those obtained by reacting with carbonate, phosgene, and the like.
  • polyhydroxyalkane examples include isoprene, butadiene, or a liquid rubber obtained by copolymerizing butadiene with acrylamide.
  • polyurethane borol examples include, for example, a polyol having a urethane bond in one molecule.
  • examples of the polyol include a polyether polyol, a polyester polyol, and a polyether ester having a molecular weight of 200 to 50,000. Those obtained by reacting a polyol or the like with a compound having at least two isocyanate groups per molecule as described below at a mole number of (NCO group or ZOH group) of less than 1, preferably 0.9 or less. Is mentioned.
  • a low molecular weight polyol may be mixed in addition to the polyol described above.
  • specific examples of these low molecular weight polyols include, for example, ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol.
  • Glycols used in the production of polyester polyols such as diols, 2,4-getyl-1,5-pentanediol, diethylene glycol, dipropylene glycol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, etc.
  • glycerin trimethylolpropane, pentaerythritol, etc. Compounds.
  • the compounds having various active hydrogen groups may be used alone or in combination of two or more.
  • polyoxytetramethylene glycol as one of the compounds having an active hydrogen group, a polyoxytetramethylene chain can be introduced into the molecule, and a good sliding property required for the coating agent of the present invention can be obtained. Sex can be achieved.
  • the content of polyoxytetramethylene chains required to achieve good lubricity is from 10 to 70% by weight, preferably from 20 to 60% by weight.
  • a compound having at least two isocyanate groups per molecule will be described.
  • Examples of the compound having at least two isocyanate groups per molecule used in the present invention include, for example, trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, and pentamethylene diisocyanate.
  • Adducts of the above-mentioned polyisocyanate monomers for example, polyester polyols, polyether polyols, polyether ester polyols, polyester amide polyols, polycaprolactones having a molecular weight of 200 to 200,000 described above.
  • Adducts of the above polyisocyanate monomers such as polyols, polyvalerolactone polyols, acrylic polyols, polycarbonate polyols, polyhydroxyalkanes, castor oil, and polyurethane polyols.
  • an alicyclic isocyanate compound is preferable in order to impart the coating film properties and water resistance required for the polyurethane used in the present invention.
  • a polyoxyethylene chain which is a nonionic hydrophilic group, is introduced into the polyurethane prepolymer, or a nonion having a polyoxetylene chain is used.
  • a surfactant is added.
  • the polyoxetylene chain-containing compound may be reacted simultaneously during the synthesis of the polyurethane prepolymer, reacted after the synthesis of the polyurethane prepolymer, or may be reacted with the polyurethane prepolymer. The reaction may be performed after dispersing in water.
  • these polyoxyethylene chain-containing compounds can be used alone or in combination of two or more. Further, as the polyoxyethylene chain-containing compound, a compound modified in advance may be used.
  • a nonionic surfactant containing a polyoxyethylene chain may be used.
  • nonionic surfactant containing a polyoxetylene chain examples include polyoxyethylene nonylphenyl ether and polyoxyethylene one-year xylene propylene block copolymer.
  • a soap-free type containing no surfactant is preferred from the viewpoints of performance such as water resistance and solvent resistance.
  • the polyoxyethylene chain which is a nonionic hydrophilic group, is required to be 3 to 60% by weight, preferably 5 to 40%, more preferably 7 to 30%, based on the solid content of the polyurethane resin. If it is less than 3% by weight, good water dispersibility is hardly obtained, and if it is more than 60% by weight, water resistance cannot be obtained.
  • the poly (xylene) chain is introduced into a side chain or a terminal of the polyurethane molecule.
  • the side chain or the terminal By being introduced into the side chain or the terminal, good water dispersibility can be obtained, and the physical properties of a coating film required as a coating agent for rubber products can be easily achieved.
  • the reaction between the isocyanate compound and the active hydrogen-containing compound is usually performed at room temperature to 100 ° C, and if necessary, a known organic acid, tin, lead, or amine compound is used. Can be used.
  • Examples of the amine-based urethanization catalyst include triethylamine, N, N-dimethylcyclohexylamine, N, N, N ', N'-tetramethylethylenediamine, N, N, N', N ' 1,3-Diamine, N, N, N ', N'-tetramethylhexane-1,6-diamine, N, N, N', N, ', N''pentamethylmethylentriamine, N, N, N', N ", N '' Pentamethyldipropylene triamine, Tetramethyldanidine, Triethylenediamine, N, N 'Monodimethylbiperazine, N-methyl-N' — (2-Dimethylamino) ethylbiperazine, N-methyl Morpholine, N- (N ', N'-dimethylaminoethyl) morpholine, 1,2-dimethylimidazole, 1,8-di
  • tin-based urethanization catalysts include, for example, stannath acetate, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin mercaptide, dibutyltin thiocarboxylate, dibutyltin dimaleate, dioctyltin mercaptide, Dioctyl tincture carboxylates.
  • the lead-based urethanization catalyst include lead 2-ethylhexanoate.
  • urethanization catalysts include, for example, phenylmercury propionate as a mercury-based catalyst.
  • an organic solvent can be used to make the reaction system uniform or to adjust the viscosity to an appropriate level.
  • acetone, methylethyl ketone, acetate nitrile, N-methylpyrrolidone, dioxane, ethyl acetate and the like can be mentioned. Those having relatively high solubility in water are preferred.
  • the amount of the organic solvent based on the reaction raw materials is preferably about 3 to 50% by weight.
  • the polyurethane pre-polymer is obtained by using a homogenizer, a mixer or the like in water. Dissolve or disperse in This temperature is preferably from 5 ° C to 70 ° C, and more preferably from room temperature to 50 ° C, to ensure workability.
  • the concentration of the aqueous polyurethane composition when dispersed in a medium such as water is preferably from 10 to 50% by weight so as not to increase the viscosity so much and to maintain storage stability.
  • chain extender for example, a known polyamine compound or the like is used.
  • the polyamine compound include ethylenediamine, 1,2-propanediamine, 1,6-hexamethylenediamine, piperazine, 2,5-dimethylbiperazine, isophoronediamine, and 4,4′-dicyclohexylmethanediamine.
  • Amine, 3,3'-dimethyl-4,4'Diamines such as dicyclohexylmethanediamine, 1,4-cyclohexanediamine, diethylenetriamine, dipropylenetriamine, triethylenetetraamine, tetraethylene
  • Compounds having an amino group and a hydroxyl group such as polyamines such as pentamine, hydroxyethylhydrazine, hydroxyethylethylentriamine, 2-[(2-aminoethyl) amino] ethanol, and 3-aminopropanediol; Hydrazines, acid hydrazides, aminosilanes and the like can be mentioned.
  • those derived into a polyamine compound by various reactions may be used.
  • the polyamine compounds are used alone or as a mixture of two or more.
  • the polyurethane coating agent used in the present invention may be a leveling agent, a slip agent, a thickening agent, a defoaming agent, a film-forming aid, etc., within a range that does not reduce the physical properties of the resin according to the purpose. May be added.
  • the polyurethane coating agent thus obtained is stable against salt coagulation liquid, and provides a rubber product having good lubricity without using powder by coating a rubber base material. be able to.
  • Hexamethylene diisocyanate Takenate T-700, manufactured by Takeda Pharmaceutical Co., Ltd.
  • nitrogen gas in a reactor equipped with a thermometer, nitrogen gas inlet tube and stirrer.
  • the reaction was performed at 6 CTC for 3 hours. Urea bond formation was confirmed by IR, and a polyoxyethylene chain-containing diol (A2) was obtained.
  • the obtained polyurethane coating agent (B 1) is a stable aqueous dispersion having a solid content of 30%, and has a polyoxyethylene chain content of 20.0% (per solid content) and a polyoxytetramethylene chain content. Was 39.0% (per solid) and the viscosity was 70 mPa ⁇ s. Further, the elongation of the obtained coating film was 400%.
  • the resulting polyurethane coating agent (B2) is a stable aqueous dispersion having a solid content of 30%, and has a polyoxyethylene chain content of 20.5% (per solid content) and a polyoxytetramethylene chain content of 29.2% (per solid), and the viscosity was 5 OmPas.
  • the elongation of the obtained coating film was 350%.
  • Hydrogenated xylylene diisocyanate (Takenate 600, manufactured by Takeda Pharmaceutical Co., Ltd.) while introducing nitrogen gas in a reactor equipped with a thermometer, nitrogen gas inlet tube, and stirrer 1 22. 52 Parts, polycarbonate diol with a molecular weight of 2,000 (Carposol D-2000, manufactured by Toagosei Co., Ltd.) 1 43.53 parts, trimethylol Mouth bread 2.35 parts, neopentyldaricol 29.9 parts, 45.69 parts of the above-mentioned polyoxyethylene chain-containing diol (A2), 56.00 parts of N-methylpyrrolidone, 0.069 parts of stannoct 02 phr) and reacted at 70 ° C. for 6 hours. After confirming that a predetermined isocyanate group content was reached, a polyurethane prepolymer was obtained.
  • the obtained polyurethane coating agent (B3) is a stable aqueous dispersion having a solid content of 35%, a polyoxyethylene chain content of 10.2% (per solid content), and a viscosity of 50 mPa * s. Met.
  • the elongation of the obtained coating film was 330%.
  • This polyurethane coating agent (B4) is a stable aqueous dispersion having a solid content of 30%, a polyoxyethylene chain content of 20.0% (per solid content), and a viscosity of 30 mPa ⁇ s. Was.
  • the elongation of the obtained coating film was 450%.
  • This polyurethane coating agent (B5) is a stable aqueous dispersion having a solid content of 35%, and has a polyoxyethylene chain content of 15.2% (per solid content) and a polyoxytetraethylene chain content of 35.50%. 0%, viscosity was 45 mPa ⁇ s. Comparative Example 1
  • a polyurethane coating agent (C 1) was prepared as a stable aqueous dispersion having a solid content of 30%. The elongation of the obtained coating film was 300%.
  • the obtained prepolymer was cooled to room temperature, and 73 parts of a 1.6% by weight acetone solution of ethylenediamine, 19.4 parts of a 2 M lysine solution in sodium salt, and 1 M parts of a 2 M taurine solution were stirred with high speed. 1.46 parts of an aqueous solution of lithium salt and 800.00 parts were further added, and the polyurethane was completely dispersed in water. Thereafter, THF and acetone were removed at 55 ° C under reduced pressure to obtain a polyurethane coating agent (C2). The elongation of the obtained coating film was 300%.
  • test latex membrane a 100-band X 200 Okiseki plate was preheated to 70 ° C and immersed in the following salt coagulation solution for 1 minute. After the unglazed plate was pulled out of the salt coagulation solution, it was allowed to stand for 3 minutes and immersed in the following latex compounding solution for 2 minutes. After lifting the unglazed plate from the latex formulation, it was washed with water for 3 minutes to remove water-soluble components. Then, it was dried at 70 ° C. for 30 minutes to prepare a test latex film.
  • composition of salt coagulation liquid (combination: weight ratio)
  • NBR latex is Closlen ⁇ ⁇ — 2 15 (manufactured by Takeda Pharmaceutical Co., Ltd.)
  • test latex membranes prepared above were prepared by mixing polyurethane coatings of Examples 1 to 5 and Comparative Example 2 with water so as to have a solid content of 5%. It was immersed in a single solution for 2 minutes. Thereafter, the test latex film was pulled up from the polyurethane coating solution, and dried at 80 ° C. for 1 minute using a drier.
  • the latex film which was not coated with the polyurethane coating liquid was used as a reference example 1, and the latex film of Reference Example 1 in which corn starch powder was sprayed on the surface was used as Reference Example 2 to evaluate the slipperiness.
  • each polyurethane coating solution prepared with water so that the polyurethane coating agent has a solid content of 5% 10 g of the above-mentioned salt coagulation solution for producing a latex film is dropped and stirred, and the presence or absence of precipitation of aggregates is visually observed. Confirmed.
  • the polyurethane coating solution was applied on a glass plate with a bar coater so as to have a thickness of about 2, which was immersed in water for 1 day, and the appearance of the coating film was visually evaluated.
  • the slip property was evaluated by a finger touch and a surface measuring device.
  • the dynamic friction coefficient was measured at a speed of 100 mm mZmin and a load of 100 g using a surface property measuring device (HEIDON-14N).
  • the surface to be rubbed was measured by setting a sample film coated with Teflon tape on the upper side and polyurethane coating on the lower side.
  • the water-based polyurethane coating agent for dip molded articles of the present invention has good stability against salt coagulation liquid during the production of dip molded articles, and has good adhesion to the rubber layer even in a simple coating process.
  • a dip-formed product having good lubricating properties can be produced without using a powdery lubricant.

Abstract

L'invention concerne un objet moulé réalisé par moulage au trempé, revêtu d'un matériau de revêtement qui résulte de la dispersion ou de la dissolution d'une résine de polyuréthanne non ionique dans l'eau et qui contient des chaînes polyoxyéthylène correspondant à une fourchette de 3 à 60 % de matière solide, en poids. On réalise ainsi un objet par moulage au trempé, qu'il est facile d'attacher ou de détacher, sans utiliser de lubrifiant du type talc ou amidon.
PCT/JP2000/006392 1999-09-22 2000-09-19 Materiau de revetement pour objet moule revetu realise par moulage au trempe WO2001021721A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU73164/00A AU7316400A (en) 1999-09-22 2000-09-19 Coating material for coating molded object made by dip forming

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP26931499 1999-09-22
JP11/269314 1999-09-22

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Publication Number Publication Date
WO2001021721A1 true WO2001021721A1 (fr) 2001-03-29

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004505154A (ja) * 2000-08-01 2004-02-19 アンセル・ヘルスケア・プロダクツ・インコーポレーテッド ゴム手袋用新規コーティング
JP2008522019A (ja) * 2004-12-01 2008-06-26 ダウ グローバル テクノロジーズ インコーポレイティド 安定した熱凝固性ポリウレタン分散物
JP2009531472A (ja) * 2006-02-24 2009-09-03 バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト ナノ尿素を含有する分散液
JP2013019072A (ja) * 2011-07-11 2013-01-31 Showa Glove Kk 手袋の製造方法及び手袋

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US4100309A (en) * 1977-08-08 1978-07-11 Biosearch Medical Products, Inc. Coated substrate having a low coefficient of friction hydrophilic coating and a method of making the same
EP0317258A2 (fr) * 1987-11-18 1989-05-24 Zeneca Limited Dispersions aqueuses de polyuréethane
JPH0488025A (ja) * 1990-08-01 1992-03-19 Mitsui Petrochem Ind Ltd 水分散体
JPH04293982A (ja) * 1991-03-25 1992-10-19 Toyoda Gosei Co Ltd 塗料組成物
US5169720A (en) * 1986-11-18 1992-12-08 W. R. Grace & Co.-Conn. Protein non-adsorptive polyurea-urethane polymer coated devices
EP0595149A1 (fr) * 1992-10-29 1994-05-04 Bayer Ag Compositions aqueuses de revêtement et leur utilisation pour la préparation de revêtements perméables à la vapeur d'eau

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4100309A (en) * 1977-08-08 1978-07-11 Biosearch Medical Products, Inc. Coated substrate having a low coefficient of friction hydrophilic coating and a method of making the same
US5169720A (en) * 1986-11-18 1992-12-08 W. R. Grace & Co.-Conn. Protein non-adsorptive polyurea-urethane polymer coated devices
EP0317258A2 (fr) * 1987-11-18 1989-05-24 Zeneca Limited Dispersions aqueuses de polyuréethane
JPH0488025A (ja) * 1990-08-01 1992-03-19 Mitsui Petrochem Ind Ltd 水分散体
JPH04293982A (ja) * 1991-03-25 1992-10-19 Toyoda Gosei Co Ltd 塗料組成物
EP0595149A1 (fr) * 1992-10-29 1994-05-04 Bayer Ag Compositions aqueuses de revêtement et leur utilisation pour la préparation de revêtements perméables à la vapeur d'eau

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004505154A (ja) * 2000-08-01 2004-02-19 アンセル・ヘルスケア・プロダクツ・インコーポレーテッド ゴム手袋用新規コーティング
JP2008522019A (ja) * 2004-12-01 2008-06-26 ダウ グローバル テクノロジーズ インコーポレイティド 安定した熱凝固性ポリウレタン分散物
KR101238569B1 (ko) * 2004-12-01 2013-02-28 다우 글로벌 테크놀로지스 엘엘씨 안정한 열 응집성 폴리우레탄 분산액
JP2009531472A (ja) * 2006-02-24 2009-09-03 バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト ナノ尿素を含有する分散液
JP2013019072A (ja) * 2011-07-11 2013-01-31 Showa Glove Kk 手袋の製造方法及び手袋

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