WO2015147125A1 - Composition de résine polyuréthane pour des applications d'étanchéité - Google Patents

Composition de résine polyuréthane pour des applications d'étanchéité Download PDF

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Publication number
WO2015147125A1
WO2015147125A1 PCT/JP2015/059289 JP2015059289W WO2015147125A1 WO 2015147125 A1 WO2015147125 A1 WO 2015147125A1 JP 2015059289 W JP2015059289 W JP 2015059289W WO 2015147125 A1 WO2015147125 A1 WO 2015147125A1
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WO
WIPO (PCT)
Prior art keywords
sealing
resin composition
polyurethane resin
layer
polyurethane
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PCT/JP2015/059289
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English (en)
Japanese (ja)
Inventor
脇坂　治
繁宏 大坪
田中　一幸
智 中島
Original Assignee
住友理工株式会社
東ソー株式会社
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Application filed by 住友理工株式会社, 東ソー株式会社 filed Critical 住友理工株式会社
Priority to JP2016510465A priority Critical patent/JP6518652B2/ja
Priority to CN201580007847.5A priority patent/CN105980432A/zh
Publication of WO2015147125A1 publication Critical patent/WO2015147125A1/fr

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    • 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
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C09K3/1021—Polyurethanes or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2190/00—Compositions for sealing or packing joints

Definitions

  • the present invention relates to a polyurethane resin composition for sealing. Specifically, the present invention relates to a sealing polyurethane resin composition that prevents water leakage from gaps or cracks in concrete structures and the like.
  • a urethane-based water-stopping material is used (see Patent Document 1).
  • bituminous sealing materials are likely to deteriorate over time due to rainwater soaked in joints. Therefore, sealing with bituminous sealing materials is not sufficient for a long-term water-stopping effect.
  • the bituminous sealant that has deteriorated over time as described above is very brittle and may fall off the joints, causing it to fall to passers-by, damaging automobiles while driving, and causing traffic accidents. There are also concerns.
  • the urethane-based water-stopping material disclosed in Patent Document 1 has poor flexibility and is foamed, so that it is easy to crack due to vibrations such as earthquakes, and has a sufficient water-stopping effect. There is a problem that it is difficult to obtain.
  • the present invention has been made in view of such circumstances, and an object thereof is to provide a sealing polyurethane resin composition that effectively prevents water leakage from gaps and cracks in concrete structures and the like.
  • a polyurethane resin composition for sealing which contains the following components (A) to (E) and does not contain polyoxypropylene glycol.
  • the organic polyisocyanate (E) is a polymethylene polyphenyl polyisocyanate containing 30 to 80% by mass of a dinuclear compound, and the dinuclear compound is composed of 2,2′-diphenylmethane diisocyanate and 2
  • the present inventors used a special polyurethane resin compounding liquid that contains the components (A) to (E) and does not contain polyoxypropylene glycol.
  • a polyurethane layer consisting of a cured resin layer (non-foamed urethane layer) and a foamed layer (foamed urethane layer) is formed, and this laminated structure has a better water-stopping effect than conventional foamed urethane-based waterstop materials.
  • the present invention was reached.
  • the reason why the polyurethane layer is divided into a cured resin layer and a foamed layer is that a plasticizer is blended in the material, a castor oil-based polyol is used as a polyol component, and polyoxypropylene glycol is not included. Therefore, it is considered that the difference in isocyanate concentration occurs between the lower part and the upper part due to the influence of specific gravity. That is, the urethane reaction proceeds from the lower part with a high isocyanate concentration to form a cured resin layer, while the upper part has a low isocyanate concentration, carbon dioxide generated by the reaction, and bubbles entrained by agitation and a resin density.
  • the polyurethane resin composition for sealing according to the present invention is a special one containing the components (A) to (E) and not containing polyoxypropylene glycol, and includes a cured resin layer and a foamed layer. Since the polyurethane layer is formed, a good water stop effect can be obtained. Moreover, since the said polyurethane layer has a foaming layer, it is lightweight compared with the bituminous sealant, and does not fall in a lump.
  • the sealing polyurethane resin composition of the present invention contains the following components (A) to (E) and does not contain polyoxypropylene glycol.
  • the polyoxypropylene glycol is, for example, a reaction with a low molecular polyol having 2 to 8 functional groups such as ethylene glycol, propylene glycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, sucrose, or water. 1 shows a propylene oxide ring-opening polymer such as a linear or branched polyether which has been subjected to ring-opening polymerization.
  • A Castor oil-based polyol.
  • B Plasticizer.
  • D Foam stabilizer.
  • E Organic polyisocyanate.
  • castor oil-based polyol (A) for example, castor oil, castor oil fatty acid and low molecular polyol (ethylene glycol, propylene glycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, sucrose, etc. having 2 or more functional groups) 8 low molecular polyols) and linear or branched polyesters obtained by reaction with water (for example, diglyceride of castor oil fatty acid, monoglyceride, mono, di, or triester of castor oil fatty acid and trimethylol alkane).
  • water for example, diglyceride of castor oil fatty acid, monoglyceride, mono, di, or triester of castor oil fatty acid and trimethylol alkane
  • the main component of “castor oil” is ricinoleic acid
  • “castor oil fatty acid” includes hydrogenated castor oil.
  • examples of the trimethylol alkane include trimethylol methane, trimethylol ethane, trimethylol propane, trimethylol butane, trimethylol pentane, trimethylol hexane, trimethylol heptane, trimethylol octane, trimethylol nonane, and trimethylol decane. Can give. These can be used alone or in combination of two or more.
  • the ratio of the castor oil-based polyol (A) to the total mass of the polyol in the polyurethane resin composition is usually 50 to 100% by mass, preferably 60 to 100% by mass. That is, the main component of the polyurethane resin composition is a castor oil-based polyol, but a polybutadiene other than polyoxypropylene glycol, or a polyolefin system in which a hydroxyl group is introduced at the end of a copolymer of butadiene and styrene or acrylonitrile. If it is a hydrophobic polyol, you may add polyols other than a castor oil-type polyol in the said ratio as needed.
  • plasticizer (B) examples include dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dihexyl phthalate, di-2-ethylhexyl phthalate, di-n-octyl phthalate, diisononyl phthalate, and diisodecyl phthalate.
  • the blending amount of the plasticizer (B) is in the range of 5 to 30 parts with respect to 100 parts by weight of polyol (hereinafter abbreviated as “parts”) from the viewpoint of the formation of both the foamed layer and the cured resin layer. It is preferably in the range of 10 to 25 parts.
  • Examples of the amine catalyst (C) include triethylamine, triethylenediamine, tetramethylhexanediamine, tetramethylethylenediamine, methylhydroxyethylpiperazine, N-methylmorpholine, N-methylimidazole, 1-methylimidazole, 1-ethylimidazole, 1-propylimidazole, 1-cyanoimidazole, 1-cyanomethylimidazole, 1,2-dimethylimidazole, 1,4-dimethylimidazole, 1-ethyl-2-ethylimidazole, 1-methyl-4-ethylimidazole, 1- Ethyl-2-methylimidazole, 1-ethyl-4-methylimidazole, dimethylaminopropylimidazole, hexamethyltripropylenetetramine, pyridine, ⁇ -picoline, N, N, N ′, N′-te Tramethylhexamethylenediamine, N, N,
  • triethylenediamine (TEDA) as the amine catalyst (C) from the viewpoint of the formation of both the cured resin layer and the foamed layer in the polyurethane layer.
  • the compounding amount of the amine catalyst (C) is preferably in the range of 0.5 to 5.0 parts, particularly preferably in the range of 0.7 to 3.0 parts with respect to 100 parts of the polyol. That is, if there are too many amine catalysts, curing proceeds before the foamed cells grow, so the upper fluidity disappears and the cured resin layer and the foamed layer are not separated. Conversely, if there are too few amine catalysts, the reaction This is because the time is prolonged, which hinders the construction.
  • foam stabilizer (D) examples include silicone surfactants containing no active hydrogen groups, such as siloxane-polyalkylene oxide copolymers.
  • silicone surfactants containing no active hydrogen groups such as siloxane-polyalkylene oxide copolymers.
  • NIAX SILICONE Y-16136 made by Momentive Performance Materials Japan
  • TEGOSTAB B-8407 made by Evonik Degussa Japan
  • TEGOSTAB B-8451 made by Evonik Degussa Japan
  • X20-6105 manufactured by Shin-Etsu Chemical Co., Ltd.
  • NIAX SILICONE Y-16136 is preferable because the cell size in the foamed layer is not random, distortion due to shrinkage is improved, and adhesion to mortar is further improved.
  • the blending amount of the foam stabilizer (D) is preferably in the range of 0.2 to 2.0 parts with respect to 100 parts of the polyol from the viewpoint of effectively obtaining the above-described effects by the foam stabilizer. Particularly preferred is a range of 0.5 to 1.5 parts.
  • organic polyisocyanate (E) examples include aromatic, alicyclic, and aliphatic polyisocyanates, and urethane-modified products, allophanate-modified products, uretdione-modified products, isocyanurate-modified products, and carbodiimide-modified products. And modified polyisocyanates such as uretonimine modified, urea modified and biuret modified.
  • aromatic polyisocyanate examples include tolylene diisocyanate (hereinafter abbreviated as “TDI” in some cases), diphenylmethane diisocyanate (hereinafter abbreviated as “MDI” in some cases), naphthalene diisocyanate, and triphenylmethane triisocyanate.
  • TDI tolylene diisocyanate
  • MDI diphenylmethane diisocyanate
  • naphthalene diisocyanate examples include triphenylmethane triisocyanate.
  • XDI Xylylene diisocyanate
  • TMXDI tetramethylxylylene diisocyanate
  • PDI polymethylene polyphenyl polyisocyanate
  • aromatic polyisocyanates each include single products and mixtures of various isomers.
  • examples of the alicyclic polyisocyanate include cyclohexylmethane diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, hydrogenated MDI, hydrogenated TDI, hydrogenated XDI, and hydrogenated TMXDI.
  • examples of the aliphatic polyisocyanate include hexamethylene diisocyanate and lysine diisocyanate.
  • aromatic polyisocyanates are preferable, and P-MDI is more preferable from the viewpoint of low viscosity and influence on the environment.
  • these organic polyisocyanate (E) can be used individually or in combination of 2 or more types.
  • Examples of the P-MDI include polymeric MDI represented by the following general formula (1).
  • the dinuclear contains 5 to 60 in total of 2,2′-diphenylmethane diisocyanate and 2,4′-diphenylmethane diisocyanate.
  • Those containing mass% are preferably used. That is, when the dinuclear content is less than 30% by mass, the viscosity of the liquid may be increased and the filling property may be hindered.
  • the dinuclear content is more than 80% by mass, a crystal may be generated at a low temperature. is there.
  • the blending ratio of the organic polyisocyanate (E) to the polyol is such that the NCO index [equivalent ratio of NCO group in isocyanate to hydroxyl group in polyol (NCO group / OH group) ⁇ 100] is 95 to 130. It is preferable to mix
  • the polyurethane resin composition for sealing of the present invention includes an antioxidant, an ultraviolet absorber, a heat resistance improver, an antifoaming agent, a leveling agent, and a coloring agent as necessary.
  • an antioxidant an ultraviolet absorber, a heat resistance improver, an antifoaming agent, a leveling agent, and a coloring agent.
  • Agents, inorganic and organic fillers, lubricants, antistatic agents, reinforcing materials and the like may be appropriately blended.
  • the polyurethane resin composition for sealing of this invention can be prepared by mixing said each component.
  • the mixing means include manual mixing and stirring, and mixing treatment using various mixers such as a vacuum homomixer, a disper, a propeller mixer, a kneader, and a high-pressure homogenizer.
  • the sealing polyurethane resin composition of the present invention comprises a main agent containing the components (A) to (D) and a curing agent containing the component (E), and these are injected into the construction object. It is preferable to mix and use immediately before (immediately before sealing construction) from the viewpoint of pot life and the like.
  • the viscosity at the time of mixing the main agent and the curing agent is preferably in the range of 100 to 1,500 mPa ⁇ s at 25 ° C., particularly preferably 200 to 1,000 mPa ⁇ s At 25 ° C.
  • the said viscosity can be adjusted with the usage-amount of the plasticizer which is a solvent of a main ingredient.
  • the liquid temperature at the time of pouring (sealing construction) of the polyurethane resin composition for sealing of the present invention is preferably 10 to 40 ° C. That is, if the liquid temperature is too high, it becomes difficult to handle at the time of filling, and conversely if the liquid temperature is too low, the flow time becomes long, and it is easily affected by water, resulting in high foaming property, This is because the viscosity becomes high and the filling property may be hindered.
  • the polyurethane resin composition for sealing of the present invention is useful as a water-stopping material and sealing material for structures such as civil engineering and architecture, particularly as a water-stopping material and sealing material for concrete structures. Moreover, it is also possible to apply to the use of the general water stop material and sealing material in the field
  • the sealing material formed from the polyurethane resin composition for sealing according to the present invention has a polyurethane layer composed of a cured resin layer and a foamed layer. That is, the polyurethane layer formed by sealing the polyurethane resin composition for sealing of the present invention has a difference in the isocyanate concentration between the lower part and the upper part due to the influence of the specific gravity of the isocyanate, and the urethanization reaction proceeds from the lower part where the isocyanate concentration is high.
  • the lower part is a cured resin layer.
  • the upper part has a low isocyanate concentration and the carbon dioxide generated by the reaction and bubbles entrained by stirring decrease, so the resin density decreases and the reaction heat cannot be stored compared to the lower part, so the urethanization reaction is delayed and the reaction is in progress
  • a laminated structure of a cured resin layer and a foamed layer is formed by forming a foamed layer under the influence of water leakage from the joint.
  • the thickness of the entire polyurethane layer should be at least 3 cm, preferably in the range of 3 to 60 cm, more preferably in the range of 3 to 25 cm, still more preferably It is in the range of 5 to 20 cm.
  • the thickness of the cured resin layer (non-foamed urethane layer) in the polyurethane layer needs to be at least 2.5 cm, preferably in the range of 2.5 to 59 cm, more preferably 2 The range is from 5 to 22 cm, and more preferably from 4 to 18 cm.
  • the thickness of the foamed layer (foamed urethane layer) in the polyurethane layer is preferably in the range of 0.2 to 5.0 cm, more preferably in the range of 0.5 to 3.0 cm.
  • a sample X shown in FIG. 1 was produced. That is, a columnar concrete block 1 having a diameter of 75 mm and a height of 50 mm is prepared by providing a through hole 1 a having a diameter of 40 mm at the center of the plane, the concrete block 1 is placed on a flat plate, and the polyurethane prepared above is prepared. The resin composition liquid was poured into the through-hole 1a and foamed and cured in an atmosphere at 20 ° C. to form the polyurethane layer 2 (see FIG. 1).
  • a water permeability test (constant water level method) was performed on the sample X obtained in this manner in accordance with JIS A 1218 (soil permeability test method).
  • the height (water level difference) between the test specimen and water in the water permeability test was 100 cm.
  • the water level difference was set by adjusting the water pressure, and the change in water level (water permeability) was measured when the test was conducted for 12 hours. And based on the measured result, the hydraulic conductivity was calculated.
  • the polyurethane layer in the sample X was taken out after the water permeability test, and the cured resin layer and the foamed layer were measured with a caliper from the cross section.
  • the density of the cured resin layer and the foamed layer was measured on the sample using an automatic hydrometer DSG-1 manufactured by Toyo Seiki Co., Ltd. Furthermore, about the sample in which the cured resin layer was formed, the hardness (Asker A type) of the cured resin layer was measured. Moreover, the adhesive strength to mortar was measured according to the following criteria. These results are also shown in Table 2 below.
  • the comparative example has a water permeability coefficient of 10 ⁇ 6 m / s level. This is the level of fine to coarse-grained clay in the soil, and there remains a problem with regard to waterstop.
  • the example was higher than the comparative example, and mortar destruction was observed in the adhesion state, whereas the comparative example was 100% resin destruction.
  • the polyurethane resin composition for sealing of the present invention is useful as a water-stopping material and sealing material for structures such as civil engineering and architecture, particularly as a water-stopping material and sealing material for concrete structures. In addition, it can be applied to general water-stopping materials and sealing materials in other fields.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Sealing Material Composition (AREA)

Abstract

L'invention concerne une composition de résine de polyuréthane pour des applications d'étanchéité qui comprend les composants suivants (A) à (E), et ne comprend pas de polyoxypropylène glycol. Ainsi, il est possible d'empêcher efficacement les fuites d'eau par des interstices et des fissures dans des structures en béton, etc. (A) Polyol à base d'huile de ricin; (B) plastifiant; (C) catalyseur aminé; (D) stabilisateur de mousse; et (E) polyisocyanate organique.
PCT/JP2015/059289 2014-03-27 2015-03-26 Composition de résine polyuréthane pour des applications d'étanchéité WO2015147125A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2016510465A JP6518652B2 (ja) 2014-03-27 2015-03-26 シーリング材
CN201580007847.5A CN105980432A (zh) 2014-03-27 2015-03-26 密封用聚氨酯树脂组合物

Applications Claiming Priority (2)

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JP2014065818 2014-03-27
JP2014-065818 2014-03-27

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Citations (8)

* Cited by examiner, † Cited by third party
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JPS57102978A (en) * 1980-07-29 1982-06-26 Nhk Spring Co Ltd Preparation of polyurethane foam sealing material
JPH0368677A (ja) * 1989-05-22 1991-03-25 Nhk Spring Co Ltd ポリウレタンフォームシーリング材の製造方法
JP2002030277A (ja) * 2000-07-17 2002-01-31 Asahi Glass Co Ltd ポリウレタン系塗膜防水材組成物
JP2002037829A (ja) * 2000-07-27 2002-02-06 Toyo Quality One Corp 自己粘着性発泡体
JP2004308407A (ja) * 2003-03-27 2004-11-04 Sk Kaken Co Ltd 塗膜防水材
JP2010024311A (ja) * 2008-07-17 2010-02-04 Nippon Polyurethane Ind Co Ltd ウレタンエラストマー充填材
JP2011245453A (ja) * 2010-05-28 2011-12-08 Ohbayashi Corp 遮水シート用止水剤、及び、遮水シートの補修工法
JP2014001381A (ja) * 2012-05-24 2014-01-09 Toho Chem Ind Co Ltd 一液型止水剤

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US5527834A (en) * 1994-11-30 1996-06-18 Inoac Corporation Waterproof plastic foam
JP2001172350A (ja) * 1999-12-17 2001-06-26 Kao Corp ポリウレタンの製造法
JP2003040967A (ja) * 2001-07-31 2003-02-13 Mitsui Takeda Chemicals Inc 二液硬化型ウレタン組成物およびその製造方法
JP2004143314A (ja) * 2002-10-25 2004-05-20 Asahi Glass Co Ltd ポリエステルポリエーテルポリオールおよびそれを用いたウレタンプレポリマー
JP5193725B2 (ja) * 2008-07-31 2013-05-08 日本発條株式会社 防水シーリング材
CN101684171B (zh) * 2008-09-27 2012-11-14 上海联合气雾制品灌装有限公司 用可再生原料制备单组分聚氨酯泡沫
JP2010215829A (ja) * 2009-03-18 2010-09-30 Sanyo Chem Ind Ltd 硬化性ポリウレタン組成物
JP5492714B2 (ja) * 2010-09-09 2014-05-14 株式会社ブリヂストン ポリウレタンフォーム

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57102978A (en) * 1980-07-29 1982-06-26 Nhk Spring Co Ltd Preparation of polyurethane foam sealing material
JPH0368677A (ja) * 1989-05-22 1991-03-25 Nhk Spring Co Ltd ポリウレタンフォームシーリング材の製造方法
JP2002030277A (ja) * 2000-07-17 2002-01-31 Asahi Glass Co Ltd ポリウレタン系塗膜防水材組成物
JP2002037829A (ja) * 2000-07-27 2002-02-06 Toyo Quality One Corp 自己粘着性発泡体
JP2004308407A (ja) * 2003-03-27 2004-11-04 Sk Kaken Co Ltd 塗膜防水材
JP2010024311A (ja) * 2008-07-17 2010-02-04 Nippon Polyurethane Ind Co Ltd ウレタンエラストマー充填材
JP2011245453A (ja) * 2010-05-28 2011-12-08 Ohbayashi Corp 遮水シート用止水剤、及び、遮水シートの補修工法
JP2014001381A (ja) * 2012-05-24 2014-01-09 Toho Chem Ind Co Ltd 一液型止水剤

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JP6518652B2 (ja) 2019-05-22
JPWO2015147125A1 (ja) 2017-04-13
CN105980432A (zh) 2016-09-28

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