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WO2015093174A1 - Matériau de réparation du béton - Google Patents

Matériau de réparation du béton Download PDF

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Publication number
WO2015093174A1
WO2015093174A1 PCT/JP2014/079423 JP2014079423W WO2015093174A1 WO 2015093174 A1 WO2015093174 A1 WO 2015093174A1 JP 2014079423 W JP2014079423 W JP 2014079423W WO 2015093174 A1 WO2015093174 A1 WO 2015093174A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
concrete
mass
parts
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.)
Ceased
Application number
PCT/JP2014/079423
Other languages
English (en)
Japanese (ja)
Inventor
博美 入江
松本　高志
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.)
DIC Corp
Original Assignee
DIC Corp
Dainippon Ink and Chemicals Co 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 DIC Corp, Dainippon Ink and Chemicals Co Ltd filed Critical DIC Corp
Priority to JP2015511831A priority Critical patent/JP5765605B1/ja
Publication of WO2015093174A1 publication Critical patent/WO2015093174A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/60—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only artificial stone
    • C04B41/61—Coating or impregnation
    • C04B41/62—Coating or impregnation with organic materials
    • C04B41/63—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
    • C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
    • C04B41/48—Macromolecular compounds
    • C04B41/483—Polyacrylates
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
    • C04B2111/72—Repairing or restoring existing buildings or building materials

Definitions

  • the present invention relates to a concrete repair material having excellent adhesion to wet concrete.
  • the problem to be solved by the present invention is to provide a concrete repair material having excellent adhesion to wet concrete.
  • the present invention relates to a urethane (meth) acrylate (A) obtained by reacting a polyisoprene polyol (a1), a polyisocyanate (a2), and a (meth) acrylic compound (a3) having a hydroxyl group or an isocyanate group, and radical polymerization.
  • a concrete repair material characterized by containing a monomer (B) is provided.
  • the concrete repair material of the present invention exhibits not only adhesion to dry concrete but also excellent adhesion to wet concrete (hereinafter abbreviated as “wet surface adhesion”). Moreover, the concrete repair material of this invention is excellent also in mechanical strength, such as workability
  • the concrete repair material of the present invention is a urethane (meth) acrylate (A) obtained by reacting a polyisoprene polyol (a1), a polyisocyanate (a2) and a (meth) acrylic compound (a3) having a hydroxyl group or an isocyanate group. And a radically polymerizable monomer (B) as essential components.
  • A urethane (meth) acrylate
  • A obtained by reacting a polyisoprene polyol (a1), a polyisocyanate (a2) and a (meth) acrylic compound (a3) having a hydroxyl group or an isocyanate group.
  • a radically polymerizable monomer (B) as essential components.
  • the polyisoprepon polyol (a1) is an essential component for exhibiting excellent wet surface adhesion, and for example, polyisoprene having two or more hydroxyl groups can be used.
  • the number average molecular weight of the polyisoprene polyol (a1) is preferably in the range of 1,000 to 4,000, and preferably 1,500 to 3,000, from the viewpoint that wet surface adhesion can be further improved. The range of is more preferable.
  • the number average molecular weight of the said polyisoprepone polyol (a1) shows the value measured on condition of the following by gel permeation chromatography (GPC) method.
  • Measuring device High-speed GPC device (“HLC-8220GPC” manufactured by Tosoh Corporation) Column: The following columns manufactured by Tosoh Corporation were connected in series. "TSKgel G5000" (7.8 mm ID x 30 cm) x 1 "TSKgel G4000” (7.8 mm ID x 30 cm) x 1 "TSKgel G3000” (7.8 mm ID x 30 cm) x 1 “TSKgel G2000” (7.8 mm ID ⁇ 30 cm) ⁇ 1 detector: RI (differential refractometer) Column temperature: 40 ° C Eluent: Tetrahydrofuran (THF) Flow rate: 1.0 mL / min Injection amount: 100 ⁇ L (tetrahydrofuran solution with a sample concentration of 0.4 mass%) Standard sample: A calibration curve was prepared using the following standard polystyrene.
  • the bromine number of the polyisoprene polyol (a1) is preferably in the range of 100 to 400 g / 100 g, more preferably in the range of 150 to 300 g / 100 g, from the viewpoint that wet surface adhesion can be further improved.
  • the bromine number of the polyisoprepon polyol (a1) is a value measured according to the potentiometric titration method of JISK0070-1992.
  • polyisoprepon polyol (a1) for example, “Poly ip” manufactured by Idemitsu Kosan Co., Ltd. can be obtained as a commercial product.
  • urethane (meth) acrylate (A) When obtaining the urethane (meth) acrylate (A), if necessary, other polyols may be used in combination with the polyisoprene polyol (a1).
  • polyether polyol for example, polyether polyol, polycarbonate polyol, polyester polyol, acrylic polyol, caprolactone polyol, polybutadiene polyol and the like can be used. These polyols may be used alone or in combination of two or more.
  • polyisocyanate (a2) examples include aromatic diisocyanates such as phenylene diisocyanate, diphenylmethane diisocyanate, tolylene diisocyanate, naphthalene diisocyanate, and xylylene diisocyanate; hexamethylene diisocyanate, lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, 4,4 Aliphatic or alicyclic diisocyanates such as' -dicyclohexylmethane diisocyanate; these formalin condensates; these carbodiimide-modified products and the like can be used. These polyisocyanates may be used alone or in combination of two or more.
  • Examples of the (meth) acrylic compound (a3) having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) ) (Meth) acrylic acid alkyl ester having a hydroxyl group such as acrylate; polyethylene glycol monoacrylate, polypropylene glycol monoacrylate and the like can be used. These compounds may be used alone or in combination of two or more.
  • Examples of the (meth) acrylic compound (a3) having an isocyanate group include 2- (meth) acryloyloxyethyl isocyanate, 2- (2- (meth) acryloyloxyethyloxy) ethyl isocyanate, 1,1-bis ( (Meth) acryloyloxymethyl) ethyl isocyanate and the like can be used. These compounds may be used alone or in combination of two or more.
  • (meth) acrylate refers to one or both of methacrylate and acrylate
  • (meth) acryloyl group refers to one or both of methacryloyl group and acryloyl group
  • “Acrylic acid” refers to one or both of methacrylic acid and acrylic acid
  • “(meth) acrylic compound” refers to one or both of an acrylic compound and a methacrylic compound.
  • the method for producing the urethane (meth) acrylate (A) a conventionally known method can be used.
  • the polyisoprene polyol (a1) and the polyisocyanate (a2) are reacted to have an isocyanate group.
  • the number average molecular weight of the urethane (meth) acrylate (A) is preferably in the range of 500 to 10,000, more preferably in the range of 800 to 7,000, from the viewpoint of further improving the tensile properties and wet surface adhesion. The range is more preferable, and the range of 1,000 to 5,000 is still more preferable.
  • the number average molecular weight of the said urethane (meth) acrylate (A) shows the value measured similarly to the number average molecular weight of the said polyisoprene polyol (a1).
  • the urethane (meth) acrylate (A) may be used in combination with other radical polymerizable resins as necessary.
  • radical polymerizable resin examples include unsaturated polyester, polyester (meth) acrylate, and epoxy (meth) acrylate. These radically polymerizable resins may be used alone or in combination of two or more.
  • radical polymerizable monomer (B) examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, and hexyl.
  • dicyclopentenyloxyethyl (meth) acrylate such as dicyclopentenyloxyethyl (meth) acrylate, dicyclopentenyl (meth) acrylate, phenoxyethyl (meth) acrylate, and the like can be used.
  • These monomers may be used alone or in combination of two or more.
  • the mass ratio [(A) / (B)] of the urethane (meth) acrylate (A) and the radical polymerizable monomer (B) is 10/90 from the viewpoint of tensile properties and wet surface adhesion. It is preferably in the range of ⁇ 90 / 10, more preferably in the range of 20/80 to 60/40.
  • the radical polymerizable resin composition used in the present invention contains the urethane (meth) acrylate (A) and the radical polymerizable monomer (B) as essential components, but contains other additives as necessary. May be.
  • Examples of the other additives include a curing agent (C), a curing accelerator (D), a petroleum wax (E), a polymerization inhibitor, a pigment, a thixotropic agent, an antioxidant, a solvent, a filler, and a reinforcing material. Aggregates, flame retardants, and the like can be used. These additives may be used alone or in combination of two or more. Among these, it is preferable to contain a hardening
  • an organic peroxide from the viewpoint of surface drying at room temperature.
  • a diacyl peroxide compound, a peroxy ester compound, a hydroperoxide compound, a dialkyl peroxide compound, A ketone peroxide compound, a peroxyketal compound, an alkyl perester compound, a carbonate compound, or the like can be used.
  • These curing agents may be used alone or in combination of two or more.
  • the amount used when the curing agent (C) is used is in the range of 0.001 to 10 parts by mass with respect to 100 parts by mass of the radical polymerizable resin composition from the viewpoint of surface dryness. preferable.
  • the curing accelerator (D) is a substance having an action of decomposing the organic peroxide of the curing agent (C) by a redox reaction and facilitating generation of active radicals.
  • cobalt naphthenate, octylic acid Cobalt organic acid salts such as cobalt
  • metal soaps such as zinc octylate, vanadium octylate, copper naphthenate, barium naphthenate
  • metal chelates such as vanadium acetyl acetate, cobalt acetyl acetate, iron acetylacetonate
  • the amount used when the curing accelerator (D) is used is in the range of 0.001 to 10 parts by mass with respect to 100 parts by mass of the radical polymerizable resin composition from the viewpoint of surface dryness. Is preferred.
  • the petroleum wax (E) for example, paraffin wax, microcrystalline wax, petrolactam and the like can be used. Also.
  • the melting point of the petroleum wax (E) is preferably in the range of 43 to 72 ° C.
  • the melting point of the paraffin wax (E) is a value measured according to JIS K2235-1991.
  • the amount used when the petroleum wax (E) is used is in the range of 0.0001 to 5 parts by mass with respect to 100 parts by mass of the radical polymerizable resin composition from the viewpoint of surface dryness. preferable.
  • urethane methacrylate (A-1) having a number average molecular weight of 3142.
  • urethane methacrylate (A′-1) having a number average molecular weight of 2042.
  • urethane methacrylate (A′-2) having a number average molecular weight of 1584.
  • polyester methacrylate (A'-4) 969 parts by mass of adipic acid and methyltetrahydrophthalic anhydride in a four-necked flask equipped with a thermometer, stirrer, inert gas inlet and reflux condenser 551 parts by weight and 690 parts by weight of neopentyl glycol were added, and 11 parts by weight of monobutyltin oxide was added as an esterification catalyst, followed by reaction at 205 ° C. for 11 hours. Thereafter, the mixture was cooled to 140 ° C., and then 941 g of glycidyl methacrylate was added and reacted for 10 hours to obtain polyester methacrylate (A′-4).
  • Example 1 25 parts by mass of urethane methacrylate (A-1) obtained in Synthesis Example 1, 75 parts by mass of dicyclopentenyloxyethyl methacrylate, and 0.2 parts by mass of paraffin wax having a melting point of 54 ° C. were mixed and stirred. A radical polymerizable resin composition was obtained. Next, 20 parts by mass of the radical polymerizable resin composition was weighed and adjusted to 25 ° C., and then 1 part by mass of cumene hydroperoxide was added to obtain a concrete repair material.
  • Examples 2 to 3 and Comparative Examples 1 to 4 A concrete repair material was obtained in the same manner as in Example 1 except that the types or amounts of the radical polymerizable resin and the radical polymerizable monomer used were changed as shown in Table 1.
  • Comparative Examples 1 and 2 are embodiments in which urethane methacrylate using polybutadiene polyol and polypropylene glycol as raw materials was used, but the wet surface adhesion was poor.
  • Comparative Example 3 is an embodiment using epoxy methacrylate and polyester methacrylate instead of urethane (meth) acrylate (A), but the wet surface adhesion was poor.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Ceramic Engineering (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Organic Chemistry (AREA)
  • Working Measures On Existing Buildindgs (AREA)
  • Aftertreatments Of Artificial And Natural Stones (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

La présente invention aborde le problème consistant à pourvoir à un matériau de réparation du béton présentant une excellente adhérence au béton humide. La présente invention concerne un matériau de réparation du béton qui est caractérisé en ce qu'il comprend : un (méth)acrylate d'uréthane (A) produit en faisant réagir entre eux un polyisoprène polyol (a1), un polyisocyanate (a2) et un composé (méth)acrylique contenant un groupe hydroxy ou un groupe isocyanate (a3) ; et un monomère (B) polymérisable par voie radicalaire. La masse moléculaire moyenne en nombre du polyisoprène polyol (a1) est de préférence située dans la plage allant de 1 000 à 4 000. De plus, le nombre de brome du polyisoprène polyol (a1) est de préférence situé dans la plage allant de 100 à 400 g/100 g.
PCT/JP2014/079423 2013-12-16 2014-11-06 Matériau de réparation du béton Ceased WO2015093174A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2015511831A JP5765605B1 (ja) 2013-12-16 2014-11-06 コンクリート補修材

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013259104 2013-12-16
JP2013-259104 2013-12-16

Publications (1)

Publication Number Publication Date
WO2015093174A1 true WO2015093174A1 (fr) 2015-06-25

Family

ID=53402531

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2014/079423 Ceased WO2015093174A1 (fr) 2013-12-16 2014-11-06 Matériau de réparation du béton

Country Status (2)

Country Link
JP (1) JP5765605B1 (fr)
WO (1) WO2015093174A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020111947A (ja) * 2019-01-11 2020-07-27 デンカ株式会社 コンクリート構造物補修用樹脂組成物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6395282A (ja) * 1986-10-09 1988-04-26 Idemitsu Petrochem Co Ltd 接着剤
JP2002234921A (ja) * 2001-02-13 2002-08-23 Mitsubishi Rayon Co Ltd 低臭性アクリル系シラップ組成物
JP2004300388A (ja) * 2003-04-01 2004-10-28 Mitsubishi Chemicals Corp ウレタン系樹脂及びこれを用いた活性エネルギー線硬化性樹脂組成物
JP2006274723A (ja) * 2005-03-30 2006-10-12 Dainippon Ink & Chem Inc コンクリート用光硬化性プライマー組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2991900B2 (ja) * 1993-09-30 1999-12-20 第一工業製薬株式会社 放射線硬化性ポリウレタンポリマーエマルジョン組成物及びその製造方法
JP4320846B2 (ja) * 1999-06-10 2009-08-26 旭硝子株式会社 光硬化性組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6395282A (ja) * 1986-10-09 1988-04-26 Idemitsu Petrochem Co Ltd 接着剤
JP2002234921A (ja) * 2001-02-13 2002-08-23 Mitsubishi Rayon Co Ltd 低臭性アクリル系シラップ組成物
JP2004300388A (ja) * 2003-04-01 2004-10-28 Mitsubishi Chemicals Corp ウレタン系樹脂及びこれを用いた活性エネルギー線硬化性樹脂組成物
JP2006274723A (ja) * 2005-03-30 2006-10-12 Dainippon Ink & Chem Inc コンクリート用光硬化性プライマー組成物

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020111947A (ja) * 2019-01-11 2020-07-27 デンカ株式会社 コンクリート構造物補修用樹脂組成物
JP7245054B2 (ja) 2019-01-11 2023-03-23 デンカ株式会社 コンクリート構造物補修用樹脂組成物
JP2023088928A (ja) * 2019-01-11 2023-06-27 デンカ株式会社 コンクリート構造物補修用樹脂組成物
JP7521036B2 (ja) 2019-01-11 2024-07-23 デンカ株式会社 コンクリート構造物補修用樹脂組成物

Also Published As

Publication number Publication date
JPWO2015093174A1 (ja) 2017-03-16
JP5765605B1 (ja) 2015-08-19

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