JP4559522B2 - 硬化して改良シーラントとなるプレポリマーの製法及びそれからなる生成物 - Google Patents
硬化して改良シーラントとなるプレポリマーの製法及びそれからなる生成物 Download PDFInfo
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- 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
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- 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
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- 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
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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- C08G18/72—Polyisocyanates or polyisothiocyanates
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- 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
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- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/778—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur silicon
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- 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
- C08G18/80—Masked polyisocyanates
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- C08G2190/00—Compositions for sealing or packing joints
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Description
本発明に有用な、末端に活性水素を有するウレタンポリマーは、有機ジ−またはポリイソシアナート反応物成分と、ポリエーテルポリオールであることができるかまたはポリオール類の組合せ物を含む、理論量よりも過剰のポリオール反応物成分との反応によって調製することができる。それぞれの反応物の反応性に依存して触媒を使用できよう。反応温度は典型的に60℃から90℃までの範囲にあり、また反応時間は典型的に約2〜8時間の程度である。実施例調製物は次項に示す。
シーラント
上記シラン末端ウレタンポリマーを含む一液型シーラント配合物を、シリル化ポリウレタン及び通例の官能性添加剤、たとえば1種以上の充填剤、可塑剤、チキソトロープ剤、酸化防止剤、UV安定剤、接着増進剤及び/または硬化触媒を一緒に混合することによって調製することができる。満足すべき混合は二重遊星形ミキサーを用いて得られる。典型的には、シリル化ウレタンポリマー、充填剤、安定剤及び可塑剤を真空中で80℃において60〜90分間混合する。50℃に冷却後、所望のシラン接着増進剤、脱水剤及び硬化触媒を加えて、混合物を窒素雰囲気中でさらに30分間撹拌する。
合成後、シリル化ポリウレタンの一部を、硬化触媒としての1重量%のジブチルスズジラウレート(DBTDL)と十分に混合した。触媒とシリル化ポリマーとの均一混合物を次にTEFLON PTFE成形型に流し込み、23℃及び相対湿度50%において2週間の間硬化用耐候室内に置いた。その後硬化したポリマーフィルムを相当するシーラントに適用する試験法を用いて本明細書に記載するように試験を行った。
実施例1(系A)
規定ヒドロキシル価が27.9、相当する分子量が約4021、不飽和レベルが0.13〜0.18である通常のポリオキシプロピレンポリオール(VORANOL P4000,Dow Chemicals)414g(0.103mole)とNCO/OH比が1.4を示す4,4′−ジフェニルメタンジイソシアナート(4,4′−MDI,ISONATE M125,Dow Chemicals)36.1g(0.144mole)との混合物に反応触媒−遅延剤系としてそれぞれ60ppmのDBTDL及び20ppmのベンゾイルクロリドを加え、約3時間70〜75℃で絶えず撹拌(30rpm)を持続して、NCO含量をほぼ0.8重量%に低下させた。ついでこのイソシアナート末端ポリウレタンプレポリマー(PUR A)を21.4g(0.084mole)という相当量のN−フェニル−ガンマアミノプロピルトリメトキシシラン(Silane I)と反応させて、シリル化ポリウレタンSPUR Aを生成させた。反応はNCO含量がゼロになるまで70〜75℃に保持した。
実施例2(系B)
規定不飽和レベルが0.005meq/g、規定ヒドロキシル価が28.4、相当する分子量が3950である低不飽和ポリオキシプロピレンポリオール(ACCLAMTM4200,ARCO Chemical)322g(0.082mole)とNCO/OH比が1.4を示す4,4′−ジフェニルメタンジイソシアナート(4,4′−MDI,ISONATE M125,Dow Chemicals)28.5g(0.114mole)との混合物に触媒として20ppmのDBTDLを加え、約3時間70〜75℃で絶えず撹拌(30rpm)を持続して、NCO含量を略0.8重量%に低下させた。次いでこのイソシアナート末端ポリウレタンプレポリマー(PUR B)を18.6g(0.073mole)という相当量のN−フェニル−ガンマアミノプロピルトリメトキシシラン(Silane I)と反応させて、シリル化ポリウレタンSPUR Bを生成させた。反応はNCO含量がゼロになるまで70〜75℃に保持した。
実施例3(系C)
低不飽和ポリオキシプロピレンポリオール(ACCLAIMTM4200,ARCO Chemicals)382g(0.094mole)とNCO/OHの比が0.62を示す4,4′−MDI(ISONATE M125,Dow Chemicals)14.5g(0.058mole)との混合物に触媒として20ppmのDBTDLを加え、約3時間70〜75℃で絶えず撹拌(30rpm)を持続して、そのNCO含量をゼロに低下させた。次いでこのヒドロキシル基末端ポリウレタンプレポリマー(PUR C)を14.6g(0.071mole)のガンマイソシアナトプロピルトリメトキシシラン(Silane II)と反応させて、シリル化ポリウレタンSPUR Cを生成させた。反応はNCO含量がゼロになるまで70〜75℃に保持した。
実施例4(系D)
規定不飽和レベルが0.005meq/g、規定ヒドロキシル価が13.8及び相当する分子量が8130である低不飽和ポリオキシプロピレンポリオール(ACCLAIMTM8200,ARCO Chemicals)311.4g(0.038mole)とNCO/OHの比が0.5を示すIPDI(VESTANATE,Huls)4.3g(0.019mole)との混合物に触媒として40ppmのジブチルスズジラウレ−トを加え、約3時間70〜75℃で絶えず撹拌(30rpm)を持続してそのNCO含量をゼロに低下させた。ついでこのヒドロキシル基末端ポリウレタンプレポリマー(PUR D)を9.93g(0.04mole)のガンマイソシアナトプロピルトリエトキシシラン(Silane III)と反応させてシリル化ポリウレタンSPUR Dを生成させた。反応はNCO含量が再びゼロになるまで70〜75℃に保持した。
実施例5(系E)
低不飽和ポリオキシプロピレンポリオール(PPO,ACCLAIMTM8200,ARCO Chemicals)238.1g(0.029mole)とNCO/OHの比が0.67を示すIPDI(VESTANATE,Huls)4.35g(0.019mole)との混合物に触媒として40ppmのジブチルスズジラウレートを加え、70〜75℃で約3時間絶えず撹拌(30ppm)を持続してNCO含量をゼロに低下させた。次いでこのヒドロキシル基末端ポリウレタンプレポリマー(PUR E)を5.06g(0.02mole)のガンマイソシアナトプロピルトリエトキシシラン(Silane III)と反応させて、シリル化ポリウレタンSPUR Eを生成させた。反応はNCO含量がゼロになるまで70〜75℃に保持した。
シーラント系−実施例F〜K−を前記の方法を用いて配合した。下記の成分及び量を使用した:
実施例11−12(ポリマーU、V及びシーラントX、Y)
実施例U:通常のポリオキシプロピレンポリオール(VORANOL P4000,Dow Chemicals)315.3g(0.079mole)とNCO/OHの比が0.75を示す4,4′−ジフェニルメタンジイソシアナート(4,4′−MDI,ISONATE M125,Dow Chemicals)14.8g(0.059mole)との混合物にジブチルスズジラウレート(DBTDL)触媒として5ppmのスズを加え、約3時間70〜75℃で絶えず撹拌(30rpm)を持続してNCO含量をゼロに低下させた。次いでこのヒドロキシル基末端ポリウレタンプレイマー(PUR U)を8.47g(0.041mole)のガンマイソシアナトプロピルトリメトキシシラン(SilaneII)と反応させてシリル化ポリウレタンSPUR Uを生成させた。反応はNCO含量が再びゼロになるまで70〜75℃に保持した。
Claims (12)
- (A)(i)分子量が2,000〜20,000ドルトンでポリオール1グラム当たり0.02ミリ当量未満の末端不飽和を有するポリオール成分と(ii)ジイソシアナート成分とを、前記ジイソシアナート成分に対して前記ポリオール成分を理論量よりも過剰に反応させ、それによってヒドロキシル末端のポリウレタンプレポリマーを生成させ;ついで
(B)前記ポリウレタンプレポリマーを、
式(1):OCN−R−Si−(X)m(−OR1)3-m
(式中mは0、1または2であり、各R1は1〜4個の炭素原子を含有するアルキルであり、各Xは1〜4個の炭素原子を含有するアルキルであり、そしてRは二価の有機基である。)の1種以上のイソシアナートシラン類と反応させて、前記イソシアナートシランで前記プレポリマーのヒドロキシル基を末端封鎖することを含み、
前記ポリオールはポリプロピレングリコールであるシリル化ポリウレタンの調製法。 - Rが2〜6個の炭素原子を含有する二価の直鎖または分枝鎖アルキルである請求項1記載の方法。
- mがゼロである請求項1記載の方法。
- mが1である請求項1記載の方法。
- 前記式(1)のイソシアナートシランがガンマイソシアナトプロピルトリメトキシシランまたはガンマイソシアナトプロピルトリエトキシシランである請求項1記載の方法。
- ポリオール1グラム当たり0.005ミリ当量以下の末端不飽和を有するポリオール成分を用いる請求項1記載の方法。
- (A)(i)分子量が2,000〜20,000ドルトンでポリオール1グラム当たり0.02ミリ当量未満の末端不飽和を有するポリオール成分と(ii)ジイソシアナート成分とを、前記ジイソシアナート成分に対して前記ポリオール成分を理論量よりも過剰に反応させ、それによってヒドロキシル基末端のポリウレタンプレポリマーを生成させ;ついで
(B)前記ポリウレタンプレポリマーを、
式(1):OCN−R−Si−(X)m(−OR1)3-m
(式中mは0、1または2であり、各R1は1〜4個の炭素原子を含有するアルキルであり、各Xは1〜4個の炭素原子を含有するアルキルであり、またRは二価の有機基である。)
の1種以上のイソシアナートシラン類と反応させて、前記イソシアナートシランで前記プレポリマーのヒドロキシル基を末端封鎖することを含み、
前記ポリオールはポリプロピレングリコールである方法によって調製されるシリル化ポリウレタン。 - mがゼロである請求項7記載のシリル化ポリウレタン。
- mが1である請求項7記載のシリル化ポリウレタン。
- 前記式(1)のイソシアナートシランがガンマイソシアナトプロピルトリメトキシシランまたはガンマイソシアナトプロピルトリエトキシシランである請求項7記載のシリル化ポリウレタン。
- 前記ジイソシアナート成分が2,4−トルエンジイソシアナート、2,6−トルエンジイソシアナート、4,4’−ジフェニルメタンジイソシアナート、2,4’−ジフェニルメタンジイソシアナート、イソホロンジイソシアナート、4,4’−ジシクロヘキシルメタンジイソシアナート異性体、及びそれらの混合物からなる群から選ばれる請求項7記載のシリル化ポリウレタン。
- ポリオール1グラム当たり0.005ミリ当量以下の末端不飽和を有するポリオール成分を用いて調製される請求項7記載のシリル化ポリウレタン。
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Application Number | Priority Date | Filing Date | Title |
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US09/009,868 US5990257A (en) | 1998-01-22 | 1998-01-22 | Process for producing prepolymers which cure to improved sealants, and products formed thereby |
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JP11013801A Division JPH11279249A (ja) | 1998-01-22 | 1999-01-22 | 硬化して改良シ―ラントとなるプレポリマ―の製法およびそれからなる生成物 |
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JP2009036018A Expired - Lifetime JP4559522B2 (ja) | 1998-01-22 | 2009-02-19 | 硬化して改良シーラントとなるプレポリマーの製法及びそれからなる生成物 |
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US (1) | US5990257A (ja) |
EP (1) | EP0931800B1 (ja) |
JP (2) | JPH11279249A (ja) |
KR (1) | KR100552020B1 (ja) |
CN (1) | CN1138808C (ja) |
AU (1) | AU762333B2 (ja) |
BR (1) | BR9900123A (ja) |
DE (1) | DE69920986T2 (ja) |
SG (1) | SG70148A1 (ja) |
Families Citing this family (172)
Publication number | Priority date | Publication date | Assignee | Title |
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DE19908562A1 (de) * | 1998-03-25 | 1999-10-07 | Henkel Kgaa | Polyurethan und polyurethanhaltige Zubereitung |
DE10108038C1 (de) * | 2001-02-20 | 2002-01-17 | Consortium Elektrochem Ind | Isocyanatfreie schäumbare Mischungen |
DE50201289D1 (de) * | 2001-02-20 | 2004-11-18 | Consortium Elektrochem Ind | Isocyanatfreie schäumbare mischungen mit hoher härtungsgeschwindigkeit |
EP1256595A1 (de) * | 2001-05-10 | 2002-11-13 | Sika AG, vorm. Kaspar Winkler & Co. | Klebstoff, gefüllt mit oberflächenbehandelter Kreide und Russ |
DE10139132A1 (de) * | 2001-08-09 | 2003-02-27 | Consortium Elektrochem Ind | Alkoxyvernetzende einkomponentige feuchtigkeitshärtende Massen |
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Also Published As
Publication number | Publication date |
---|---|
EP0931800B1 (en) | 2004-10-13 |
CN1138808C (zh) | 2004-02-18 |
DE69920986D1 (de) | 2004-11-18 |
JPH11279249A (ja) | 1999-10-12 |
KR100552020B1 (ko) | 2006-02-14 |
EP0931800A1 (en) | 1999-07-28 |
SG70148A1 (en) | 2000-01-25 |
DE69920986T2 (de) | 2005-03-10 |
KR19990068055A (ko) | 1999-08-25 |
AU762333B2 (en) | 2003-06-26 |
CN1229804A (zh) | 1999-09-29 |
JP2009149902A (ja) | 2009-07-09 |
AU1323199A (en) | 1999-08-12 |
BR9900123A (pt) | 2000-02-01 |
US5990257A (en) | 1999-11-23 |
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