WO2001053423A1 - Preparation adhesive a l'urethane, sechant a l'humidite et en un seul emballage - Google Patents
Preparation adhesive a l'urethane, sechant a l'humidite et en un seul emballage Download PDFInfo
- Publication number
- WO2001053423A1 WO2001053423A1 PCT/JP2000/000212 JP0000212W WO0153423A1 WO 2001053423 A1 WO2001053423 A1 WO 2001053423A1 JP 0000212 W JP0000212 W JP 0000212W WO 0153423 A1 WO0153423 A1 WO 0153423A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- adhesive composition
- curable
- moisture
- urethane
- pack
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
Definitions
- the present invention relates to a moisture-curable one-part urethane-based adhesive composition. More specifically, the present invention relates to a moisture-curable one-pack polyurethane adhesive composition which has good adhesion to a hard-to-adhesion coated steel sheet and can be used, for example, for bonding automotive window glass. Background art
- a moisture-curable one-pack type polyurethane composed mainly of a polyurethane prepolymer containing isocyanate groups at the molecular terminals, which is a reaction product of a polyol and an excess of a polyisocyanate compound.
- An adhesive composition is used.
- a method has been adopted in which the adhesive composition is applied to the periphery of a window glass, which is mounted on a vehicle body flange, pressed, and adhesively attached to the window glass.
- a primer containing a polyisocyanate compound as a main component is used as a pretreatment agent, but it is desired to reduce the number of steps in order to reduce the number of steps.
- the present inventors have conducted various studies in order to improve the Brammerless adhesion of the above-mentioned moisture-curable one-part urethane-based adhesive composition.
- a specific adhesive and a curing catalyst it is possible to obtain a moisture-curable one-pack polyurethane adhesive composition having good adhesion to hardly adhered coated steel sheets.
- the present invention provides a moisture-curable one-part urethane-based adhesive composition containing an isocyanate group-terminated urethane prepolymer as a main component, (1) A silane coupling agent as an adhesion agent,
- the moisture-curable one-part urethane-based adhesive composition of the present invention contains an isocyanate group-terminated urethane prepolymer as a main component.
- polystyrene-vinyl benzoate copolymers examples include polyoxyalkylene polyols (referred to as PPG), modified polyether polyols, polyether polyols such as polytetramethylene ether glycol; condensation-based polyester polyols, lactone-based polyester polyols, and polycarbonate diols.
- Polyester polyols acrylic polyols, polybutadiene-based polyols, polyolefin-based polyols, saponified styrene-vinyl benzoate copolymers, and other polyols whose main chain is composed of CC bonds; other flame retardant polyols, phosphorus-containing polyols, including Halogen polyols and the like.
- polyisocyanate compound examples include tolylene diisocyanate (TDI), 4,4'-diphenylmethane diisocyanate (MDI), xylylene diisocyanate (XDI), and hexamethylene diisonate.
- examples include cyanate (HDI), isophorone diisocyanate (IPDI), lysine diisocyanate, isopropylidenebis (4-cyclohexyl isocyanate), and hydrogenated XDI.
- the moisture-curable one-part urethane adhesive composition of the present invention contains the above-mentioned isocyanate-terminated urethane prepolymer in an amount of 20 to 60% by weight based on the whole adhesive composition.
- the moisture-curable one-part urethane adhesive composition of the present invention contains a silane coupling agent as an adhesive in addition to the isocyanate-terminated urethane prepolymer.
- silane coupling agent examples include an epoxyalkylalkoxysilane, a maleolecaptore / lekanolekoxysilane, a bieranolekoxysilane, a phenylalkoxyalkylalkoxysilane, an isocyanatoalkylalkoxysilane, and an aminoalkylalkoxysilane.
- Preferred silane coupling agents are mercaptoprovir trimethoxysilane, mercaptopropylmethyldimethoxysilane, ⁇ - ⁇ -pheny / reaminopropyl trimethoxysilane and / or ⁇ -isocyanatopropyl trimethoxysilane.
- the silane coupling agent may be present in an amount of 0.1 to 5% by weight based on the entire adhesive composition including the isocyanate-terminated urethane prepolymer and the like.
- the moisture-curable one-pack type urethane-based adhesive composition of the present invention further comprises (a) 2,2′-dimorpholinoethylester as a curing catalyst in addition to an isocyanate-terminated urethane prepolymer and an adhesive. And / or di (2,6-dimethylmorpholinoethyl) ether, and (b) dibutyltin diacetylacetonate.
- 2,2′-Dimorpholinoethyl ether and / or di (2,6-dimethylmorpholinoethyl) ether is preferably from 0.05 to 2% based on the entire adhesive composition including the isocyanate group-terminated urethane prepolymer. It may be present in an amount of 0.0% by weight.
- the amount of dibutyltin diacetylacetonate is 0.0001 to 0.5% by weight, based on the entire adhesive composition including the isocyanate group-terminated pentane polymer. /. May be present in amounts.
- a part of the isocyanate group-terminated urethane prepolymer in the moisture-curable one-pack type urethane-based adhesive composition of the present invention is a hexamethylene diisocyanate derivative.
- hexamethylene diisocyanate derivative examples include a modified burette, a modified isocyanurate, and a modified z or trimethylolpropane.
- Hexamethylene diisocyanate derivative is based on the entire adhesive composition,
- the moisture-curable one-part urethane-based adhesive composition of the present invention has an isocyanate group terminal.
- it may further contain a plasticizer, a filler, a solvent and the like.
- plasticizer examples include diisononyl phthalate, octyl phthalate (DOP), dibutyl phthalate, dilauryl phthalate, butyl benzyl phthalate, octyl radiate, disodecyl radiate, trioctyl phosphate, and tris (chloroethyl).
- DOP diisononyl phthalate
- dilauryl phthalate butyl benzyl phthalate
- octyl radiate disodecyl radiate
- trioctyl phosphate examples include phosphate, tris (dichloropropyl) phosphate, propylene glycol adipate polyester, butylene glycol adipate, alkyl epoxystearate, alkylbenzene, and epoxidized soybean oil.
- the plasticizer may be present in an amount of from 10 to 100% by weight, based on the
- the filler examples include calcium carbonate, silica, carbon black, clay, talc, titanium oxide, quicklime, kaolin, zeolite, and diatomaceous earth.
- the filler may be present in an amount of from 10 to 200% by weight, based on the total adhesive composition.
- the solvent examples include xylene and toluene.
- the solvent may optionally be present in an amount of 0 to 20% by weight, based on the entire adhesive composition.
- the moisture-curable one-pack type urethane-based adhesive composition of the present invention may contain an adhesion-imparting agent (such as a titanate-based coupling agent), an antioxidant, and a pigment in appropriate amounts. it can.
- an adhesion-imparting agent such as a titanate-based coupling agent
- the moisture-curable one-part urethane-based adhesive composition of the present invention is obtained by sequentially adding an adhesive, a curing catalyst, a plasticizer, a filler, a solvent, and other additives to an isocyanate group-terminated urethane prepolymer, followed by mixing. By doing so, it can be manufactured.
- a moisture-curable, one-pack polyurethane adhesive composition was prepared in the same manner as in Example 1 except that mercaptopropyltrimethoxysilane was changed to ⁇ - ⁇ -phenylaminopropyltrimethoxysilane.
- a moisture-curable one-component urethane-based adhesive composition was prepared in the same manner as in Example 1 except that the addition of dibutyltin diacetyl acetonate was omitted.
- a moisture-curable one-part urethane-based adhesive composition was prepared in the same manner as in Example 1 except that addition of mercaptopropyltrimethoxysilane and dibutyltin diacetylacetonate was omitted.
- the adhesive compositions of Examples 1 to 3 and Comparative Examples 1 and 2 were evaluated for primerless adhesion.
- Normal adhesiveness The above adhesive composition is applied in a bead form to the following coated steel sheet. After releasing the release paper and pressing it so that the thickness of the adhesive composition becomes 3 mm, it is left for 72 hours at 20 ° C. and 65% RH. Peeling with a knife cut is performed for normal adhesion.
- the numbers indicate the area ratio.
- the moisture-curable one-part urethane-based adhesive composition of the present invention can be used for bonding and sealing in fields such as automobiles, construction, and civil engineering.
- the moisture-curable one-part urethane-based adhesive composition of the present invention is suitable for bonding an automobile window glass to a vehicle body.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2000/000212 WO2001053423A1 (fr) | 2000-01-19 | 2000-01-19 | Preparation adhesive a l'urethane, sechant a l'humidite et en un seul emballage |
US10/169,732 US6657035B1 (en) | 2000-01-19 | 2000-01-19 | Moisture-curable one-pack-type urethane adhesive composition |
JP2001553886A JP4326181B2 (ja) | 2000-01-19 | 2000-01-19 | 湿気硬化性一液型ウレタン系接着剤組成物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2000/000212 WO2001053423A1 (fr) | 2000-01-19 | 2000-01-19 | Preparation adhesive a l'urethane, sechant a l'humidite et en un seul emballage |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/169,732 A-371-Of-International US6657035B1 (en) | 2000-01-19 | 2000-01-19 | Moisture-curable one-pack-type urethane adhesive composition |
US10/674,824 Continuation-In-Part US20040143055A1 (en) | 2002-07-16 | 2003-10-01 | Moisture-curing one-pack urethane adhesive compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001053423A1 true WO2001053423A1 (fr) | 2001-07-26 |
Family
ID=11735585
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2000/000212 WO2001053423A1 (fr) | 2000-01-19 | 2000-01-19 | Preparation adhesive a l'urethane, sechant a l'humidite et en un seul emballage |
Country Status (3)
Country | Link |
---|---|
US (1) | US6657035B1 (ja) |
JP (1) | JP4326181B2 (ja) |
WO (1) | WO2001053423A1 (ja) |
Cited By (22)
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JP2005075877A (ja) * | 2003-08-29 | 2005-03-24 | Nippon Nsc Ltd | 湿気硬化型ホットメルト接着剤組成物 |
JP2005535779A (ja) * | 2002-08-14 | 2005-11-24 | コンゾルテイウム フユール エレクトロケミツシエ インヅストリー ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 制御可能な硬化速度を有するアルコキシシラン末端ポリマーをベースとするポリマー材料 |
JP2006177551A (ja) * | 2004-11-25 | 2006-07-06 | Nhk Spring Co Ltd | ガスケット、その製造方法及びその施工方法 |
JP2007503512A (ja) * | 2003-08-22 | 2007-02-22 | ダウ グローバル テクノロジーズ インコーポレイティド | 車両窓の取付用接着剤として有用な組成物 |
JP2007536422A (ja) * | 2004-05-10 | 2007-12-13 | シーカ・テクノロジー・アーゲー | 高い初期強度を有するポリウレタン組成物 |
JP2011504192A (ja) * | 2007-11-07 | 2011-02-03 | ダウ グローバル テクノロジーズ インコーポレイティド | 充填剤レベルの高いポリウレタン接着剤組成物 |
WO2014136800A1 (ja) * | 2013-03-07 | 2014-09-12 | 横浜ゴム株式会社 | 一液湿気硬化型組成物 |
US9085716B2 (en) | 2011-02-17 | 2015-07-21 | Dow Global Technologies Llc | Alkoxysilane containing polyurethane adhesive compositions containing calcium carbonate |
JP5794356B1 (ja) * | 2014-06-30 | 2015-10-14 | 横浜ゴム株式会社 | ウレタン系接着剤組成物 |
JP2015229738A (ja) * | 2014-06-06 | 2015-12-21 | 信越化学工業株式会社 | ウレタン接着剤組成物 |
WO2016006501A1 (ja) * | 2014-07-11 | 2016-01-14 | 横浜ゴム株式会社 | 1液湿気硬化型ウレタン組成物及びその製造方法 |
WO2017014185A1 (ja) * | 2015-07-17 | 2017-01-26 | 横浜ゴム株式会社 | 接着剤組成物及びその製造方法 |
JP2017533299A (ja) * | 2014-09-22 | 2017-11-09 | シーカ・テクノロジー・アーゲー | ガラス上で急速な接着形成を行う貯蔵安定性、湿気硬化ポリウレタン接着剤 |
WO2018087743A1 (ja) * | 2016-11-14 | 2018-05-17 | 積水化学工業株式会社 | 湿気硬化型樹脂組成物及び組立部品 |
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JP2021513582A (ja) * | 2018-02-12 | 2021-05-27 | ディディピー スペシャリティ エレクトロニック マテリアルズ ユーエス エルエルシー | ポリウレタン接着剤組成物 |
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US20040143055A1 (en) * | 2002-07-16 | 2004-07-22 | Sunstar Giken Kabushiki Kaisha, A Corporation Of Japan | Moisture-curing one-pack urethane adhesive compositions |
US7888425B2 (en) * | 2004-07-16 | 2011-02-15 | Reichhold, Inc. | Low volatile organic compound stable solvent-based polyurethane compositions for coatings |
US7825780B2 (en) | 2005-10-05 | 2010-11-02 | Telecommunication Systems, Inc. | Cellular augmented vehicle alarm notification together with location services for position of an alarming vehicle |
US7601239B1 (en) * | 2006-04-04 | 2009-10-13 | Comptek Structural Composites Of Colorado, Inc. | Liquid adhesive |
JP5426388B2 (ja) * | 2006-10-05 | 2014-02-26 | ダウ グローバル テクノロジーズ エルエルシー | ガラス結合用プライマー組成物 |
KR101605928B1 (ko) * | 2008-12-23 | 2016-03-23 | 다우 글로벌 테크놀로지스 엘엘씨 | 신속한 운행가능 시간을 제공하는 차량 창문 설치에 유용한 접착제 |
JP5532224B2 (ja) * | 2010-02-26 | 2014-06-25 | 大日精化工業株式会社 | ウレタンプレポリマー |
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JP2022539322A (ja) | 2019-06-25 | 2022-09-08 | ディディピー スペシャルティ エレクトロニック マテリアルズ ユーエス,エルエルシー | 硬化ポリウレタン接着剤組成物の迅速化 |
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2000
- 2000-01-19 JP JP2001553886A patent/JP4326181B2/ja not_active Expired - Fee Related
- 2000-01-19 WO PCT/JP2000/000212 patent/WO2001053423A1/ja active Application Filing
- 2000-01-19 US US10/169,732 patent/US6657035B1/en not_active Expired - Lifetime
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Cited By (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005535779A (ja) * | 2002-08-14 | 2005-11-24 | コンゾルテイウム フユール エレクトロケミツシエ インヅストリー ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 制御可能な硬化速度を有するアルコキシシラン末端ポリマーをベースとするポリマー材料 |
JP2007503512A (ja) * | 2003-08-22 | 2007-02-22 | ダウ グローバル テクノロジーズ インコーポレイティド | 車両窓の取付用接着剤として有用な組成物 |
JP4673306B2 (ja) * | 2003-08-22 | 2011-04-20 | ダウ グローバル テクノロジーズ エルエルシー | 車両窓の取付用接着剤として有用な組成物 |
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