JP2014208787A - 硬化性組成物およびその硬化物 - Google Patents
硬化性組成物およびその硬化物 Download PDFInfo
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- JP2014208787A JP2014208787A JP2014060261A JP2014060261A JP2014208787A JP 2014208787 A JP2014208787 A JP 2014208787A JP 2014060261 A JP2014060261 A JP 2014060261A JP 2014060261 A JP2014060261 A JP 2014060261A JP 2014208787 A JP2014208787 A JP 2014208787A
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- CLYWMXVFAMGARU-UHFFFAOYSA-N n-benzyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCC1=CC=CC=C1 CLYWMXVFAMGARU-UHFFFAOYSA-N 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
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- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
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- 229920002601 oligoester Polymers 0.000 description 1
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- JTQPTNQXCUMDRK-UHFFFAOYSA-N propan-2-olate;titanium(2+) Chemical compound CC(C)O[Ti]OC(C)C JTQPTNQXCUMDRK-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical group CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
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- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
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- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
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- UZIAQVMNAXPCJQ-UHFFFAOYSA-N triethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C(C)=C UZIAQVMNAXPCJQ-UHFFFAOYSA-N 0.000 description 1
- QYBKVVRRGQSGDC-UHFFFAOYSA-N triethyl methyl silicate Chemical compound CCO[Si](OC)(OCC)OCC QYBKVVRRGQSGDC-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
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- C09D7/12—
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- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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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
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- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
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Abstract
【解決手段】(A)シロキサン結合を形成することにより架橋し得る反応性ケイ素含有基を有する有機重合体、(B)N−アルキル−2−アザ−1−シクロアルカノン(ただしアルキル基は炭素数3以上である)を含有する硬化性組成物。(B)成分がN−アルキル−2−ピロリドンである硬化性組成物。
【選択図】なし
Description
(I).(A)シロキサン結合を形成することにより架橋し得るケイ素含有基を有する有機重合体100重量部、(B)N−アルキル−2−アザ−1−シクロアルカノンを20重量部を超えて300重量部未満を含有する硬化性組成物であって、(B)成分のアルキル基の炭素数が3〜22の範囲にある硬化性組成物、
(II).(B)成分がN−アルキル−2−ピロリドンである(I)に記載の硬化性組成物、
(III).(A)成分の有機重合体の主鎖骨格が、ポリオキシアルキレン系重合体、飽和炭化水素系重合体、および(メタ)アクリル酸エステル系重合体からなる群から選択される少なくとも1種の重合体である(I)〜(II)のいずれかに記載の硬化性組成物、
(IV).ポリオキシアルキレン系重合体がポリオキシプロピレン系重合体である(III)に記載の硬化性組成物、
(V).(A)成分のケイ素含有基が、トリメトキシシリル基、トリエトキシシリル基、ジメトキシメチルシリル基からなる群から選択される少なくとも1種である(I)〜(IV)のいずれかに記載の硬化性組成物、
(VI).(C)成分としてアミノシランを含有することを特徴とする(I)〜(V)のいずれかに記載の硬化性組成物、
( VII).(D)成分として硬化触媒を含有することを特徴とする(I)〜(VI)のいずれかに記載の硬化性組成物、
(VIII).(I)〜(VII)のいずれかに記載の硬化性組成物を用いてなるシーリング材、
(IX).(I)〜(VII)のいずれかに記載の硬化性組成物を用いてなる接着剤、
(X).(I)〜(VII)のいずれかに記載の硬化性組成物を用いてなるコーティング材、
(XI).(I)〜(VII)のいずれかに記載の硬化性組成物を用いてなる防水材、
(XII).(I)〜(VII)のいずれかに記載の硬化性組成物を用いた硬化物、
に関する。
また、ポリオキシアルキレン系重合体および(メタ)アクリル酸エステル系重合体は、透湿性が高く1液型組成物にした場合に深部硬化性に優れ、更に接着性にも優れることから特に好ましく、ポリオキシアルキレン系重合体は最も好ましい。ポリオキシアルキレン系重合体の中でも、ポリオキシプロピレン系重合体が特に好ましい。
−SiR1 3−aXa (1)
(R1は、それぞれ独立に炭素原子数1から20のアルキル基、炭素原子数6から20のアリール基、炭素原子数7から20のアラルキル基、または、−OSi(R’)3(R’は、それぞれ独立に炭素原子数1から20の炭化水素基である)で示されるトリオルガノシロキシ基である。また、Xは、それぞれ独立にヒドロキシ基または加水分解性基である。更に、aは1から3の整数である)で表される基があげられる。
H−(SiR2 2O)mSiR2 2−R3−SiX3 (2)
(Xは前記に同じ。2m+2個のR2は、それぞれ独立に炭化水素基であり、入手性およびコストの点から、炭素原子数1から20の炭化水素基が好ましく、炭素原子数1から8の炭化水素基がより好ましく、炭素原子数1から4の炭化水素基が特に好ましい。R3は2価の有機基であり、入手性およびコストの点から、炭素原子数1から12の2価の炭化水素基が好ましく、炭素原子数2から8の2価の炭化水素基がより好ましく、炭素原子数2の2価の炭化水素基が特に好ましい。また、mは0から19の整数であり、入手性およびコストの点から、1が好ましい)で表されるシラン化合物は、不均化反応が進まない。この為、(I)の合成法で、3個の加水分解性基が1つのケイ素原子に結合している基を導入する場合には、一般式(2)で表されるシラン化合物を用いることが好ましい。一般式(2)で示されるシラン化合物の具体例としては、1−[2−(トリメトキシシリル)エチル]−1,1,3,3−テトラメチルジシロキサン、1−[2−(トリメトキシシリル)プロピル]−1,1,3,3−テトラメチルジシロキサン、1−[2−(トリメトキシシリル)ヘキシル]−1,1,3,3−テトラメチルジシロキサンが挙げられる。
反応性ケイ素基を有する有機重合体は直鎖状、または分岐を有してもよく、その数平均分子量はGPCにおけるポリスチレン換算において500から100,000程度、より好ましくは1,000から50,000であり、特に好ましくは3,000から30,000である。数平均分子量が500未満では、硬化物の伸び特性の点で不都合な傾向があり、100,000を越えると、高粘度となる為に作業性の点で不都合な傾向がある。
−R4−O− (3)
(R4は、炭素原子数1から14の直鎖状もしくは分岐アルキレン基である)で示される繰り返し単位を有する重合体であり、一般式(3)におけるR4は、炭素原子数1から14の、更には2から4の、直鎖状もしくは分岐アルキレン基が好ましい。一般式(3)で示される繰り返し単位の具体例としては、
−CH2O−、−CH2CH2O−、−CH2CH(CH3)O−、−CH2CH(C2H5)O−、−CH2C(CH3)2O−、−CH2CH2CH2CH2O−
等が挙げられる。ポリオキシアルキレン系重合体の主鎖骨格は、1種類だけの繰り返し単位からなってもよいし、2種類以上の繰り返し単位からなってもよい。特にシーラント等に使用される場合には、プロピレンオキシド重合体を主成分とする重合体から成るものが非晶質であることや比較的低粘度である点から好ましい。
−CH2−C(R5)(COOR6)− (4)
(R5は水素原子またはメチル基、R6は炭素原子数1から8のアルキル基を示す)で表される炭素原子数1から8のアルキル基を有する(メタ)アクリル酸エステル単量体単位と、下記一般式(5):
−CH2−C(R5)(COOR7)− (5)
(R5は前記に同じ、R7は炭素原子数9以上のアルキル基を示す)で表される炭素原子数9以上のアルキル基を有する(メタ)アクリル酸エステル単量体単位からなる共重合体に、反応性ケイ素基を有するポリオキシアルキレン系重合体をブレンドして製造する方法である。
該共重合体に含有されていてもよい一般式(4)および一般式(5)以外の単量体単位としては、例えば、アクリル酸、メタクリル酸等のアクリル酸;アクリルアミド、メタクリルアミド、N−メチロールアクリルアミド、N−メチロールメタクリルアミド等のアミド基、グリシジルアクリレート、グリシジルメタクリレート等のエポキシ基、ジエチルアミノエチルアクリレート、ジエチルアミノエチルメタクリレート、アミノエチルビニルエーテル等のアミノ基を含む単量体;その他アクリロニトリル、スチレン、α−メチルスチレン、アルキルビニルエーテル、塩化ビニル、酢酸ビニル、プロピオン酸ビニル、エチレン等に起因する単量体単位があげられる。
−NR8−C(=O)− (6)
(R8は有機基または水素原子を表す)で表される基である。
W−R9−SiR1 3−aXa (7)
(R1、X、aは前記と同じ。R9は2価の有機基であり、より好ましくは炭素原子数1から20の炭化水素基である。Wはヒドロキシ基、カルボキシ基、メルカプト基およびアミノ基(1級または2級)から選ばれた活性水素含有基である)で表されるケイ素化合物のW基を反応させる方法により製造されるものを挙げることができる。この製造方法に関連した、有機重合体の公知の製造法を例示すると、特公昭46−12154号(米国特許3632557号)、特開昭58−109529号(米国特許4374237号)、特開昭62−13430号(米国特許4645816号)、特開平8−53528号(EP0676403)、特開平10−204144号(EP0831108)、特表2003−508561(米国特許6197912号)、特開平6−211879号(米国特許5364955号)、特開平10−53637号(米国特許5756751号)、特開平11−100427号、特開2000−169544号、特開2000−169545号、特開2002−212415号、特許第3313360号、米国特許4067844号、米国特許3711445号、特開2001−323040号等が挙げられる。
O=C=N−R9−SiR1 3−aXa (8)
(R9、R1、X、aは前記に同じ)で示される反応性ケイ素基含有イソシアネート化合物とを反応させることにより製造されるものを挙げることができる。この製造方法に関連した、有機重合体の公知の製造法を例示すると、特開平11−279249号(米国特許5990257号)、特開2000−119365号(米国特許6046270号)、特開昭58−29818号(米国特許4345053号)、特開平3−47825号(米国特許5068304号)、特開平11−60724号、特開2002−155145号、特開2002−249538号、WO03/018658、WO03/059981等が挙げられる。
−NR10−C(=O)− (9)
(R10は水素原子または置換あるいは非置換の有機基を表す)で表される基を有する。この構造は極性が比較的高いため、硬化物の強度や基材への接着性が高くなる傾向にあり好ましい。
−CO−NR11− (10)
(R11は炭素原子数3から22のアルキル基である)で示される構造を含む化合物である。このような化合物は、一般的にラクタムと呼ばれ、環構造を形成する原子としては、一つは窒素原子で残りは炭素原子で形成される。環構造を形成する原子の数としては、3〜20の範囲であればよい。ただし、原子数が8〜12の場合はひずみにより安定性に欠けるため、4〜7もしくは13〜16が安定で好ましい。この中でも、原子数が5または7が安定なため好ましく、5が最も好ましい。
(B)成分は分子量が50〜500のものが(A)成分を可塑化する効果が高いため好ましく、分子量が50〜300のものがより可塑化効果が高く好ましい。
アミノシラン以外の接着付与剤の具体例としては、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン、γ−グリシドキシプロピルメチルジメトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン等のエポキシ基含有シラン類;γ−イソシアネートプロピルトリメトキシシラン、γ−イソシアネートプロピルトリエトキシシラン、γ−イソシアネートプロピルメチルジエトキシシラン、γ−イソシアネートプロピルメチルジメトキシシラン、(イソシアネートメチル)トリメトキシシラン、(イソシアネートメチル)ジメトキシメチルシラン等のイソシアネート基含有シラン類;γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルトリエトキシシラン、γ−メルカプトプロピルメチルジメトキシシラン、γ−メルカプトプロピルメチルジエトキシシラン、メルカプトメチルトリエトキシシラン等のメルカプト基含有シラン類;β−カルボキシエチルトリエトキシシラン、β−カルボキシエチルフェニルビス(2−メトキシエトキシ)シラン、N−β−(カルボキシメチル)アミノエチル−γ−アミノプロピルトリメトキシシラン等のカルボキシシラン類;ビニルトリメトキシシラン、ビニルトリエトキシシラン、γ−メタクリロイルオキシプロピルメチルジメトキシシラン、γ−アクリロイルオキシプロピルメチルトリエトキシシラン等のビニル型不飽和基含有シラン類;γ−クロロプロピルトリメトキシシラン等のハロゲン含有シラン類;トリス(トリメトキシシリル)イソシアヌレート等のイソシアヌレートシラン類等を挙げることができる。また、上記シラン類を部分的に縮合した縮合体も使用できる。さらに、これらを変性した誘導体である、アミノ変性シリルポリマー、シリル化アミノポリマー、不飽和アミノシラン錯体、フェニルアミノ長鎖アルキルシラン、アミノシリル化シリコーン、シリル化ポリエステル等もシランカップリング剤として用いることができる。本発明に用いるシランカップリング剤は、通常、反応性ケイ素基を有する有機重合体(A)100重量部に対して、0.1〜20重量部の範囲で使用される。特に、0.5〜10重量部の範囲で使用するのが好ましい。
鱗片状または粒状の物質としては、ケイ砂、マイカ等の天然物、合成ゴム、合成樹脂、アルミナ等の無機物が使用される。目地部に充填した際の意匠性を高めるために、外壁の材質、模様等に合わせて、適当な色に着色される。
本発明の硬化性組成物には、必要に応じて垂れを防止し、作業性を良くするためにチクソ性付与剤(垂れ防止剤)を添加しても良い。垂れ防止剤としては特に限定されないが、例えば、ポリアミドワックス類;水添ヒマシ油誘導体類;ステアリン酸カルシウム、ステアリン酸アルミニウム、ステアリン酸バリウム等の金属石鹸類等が挙げられる。また、特開平11−349916号公報に記載されているような粒子径10から500μmのゴム粉末や、特開2003−155389号公報に記載されているような有機質繊維を用いると、チクソ性が高く作業性の良好な組成物が得られる。これらチクソ性付与剤(垂れ防止剤)は単独で用いてもよく、2種以上併用してもよい。チクソ性付与剤は(A)成分100重量部に対して、0.1から20重量部の範囲で使用される。
ポリケイ皮酸ビニル類としては、シンナモイル基を感光基とする感光性樹脂でありポリビニルアルコールをケイ皮酸でエステル化したものの他、多くのポリケイ皮酸ビニル誘導体が例示される。アジド化樹脂は、アジド基を感光基とする感光性樹脂として知られており、通常はジアジド化合物を感光剤として加えたゴム感光液の他、「感光性樹脂」(昭和47年3月17日出版、印刷学会出版部発行、第93頁から、第106頁から、第117頁から)に詳細な例示があり、これらを単独または混合し、必要に応じて増感剤を加えて使用することができる。なお、ケトン類、ニトロ化合物などの増感剤やアミン類などの促進剤を添加すると、効果が高められる場合がある。光硬化性物質は反応性ケイ素基を有する有機重合体(A)100重量部に対して0.1から20重量部、好ましくは0.5から10重量部の範囲で使用するのがよく、0.1重量部以下では耐候性を高める効果はなく、20重量部以上では硬化物が硬くなりすぎて、ヒビ割れを生じる傾向がある。
分子量約2,000のポリオキシプロピレンジオールと分子量約3,000のポリオキシプロピレントリオールの1/1(重量比)混合物を開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、数平均分子量約19,000(送液システムとして東ソー製HLC−8120GPCを用い、カラムは東ソー製TSK−GEL Hタイプを用い、溶媒はTHFを用いて測定したポリスチレン換算分子量)のポリプロピレンオキシドを得た。続いて、この水酸基末端ポリプロピレンオキシドの水酸基に対して1.2倍当量のNaOMeのメタノール溶液を添加してメタノールを留去し、更に水酸基に対して1.7倍当量の塩化アリルを添加して末端の水酸基をアリル基に変換した。
数平均分子量約3,000のポリオキシプロピレントリオールを開始剤とし亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキシドの重合を行い、数平均分子量約26,000(合成例1と同様の方法で測定したポリスチレン換算値)のポリプロピレンオキシドを得た。続いて、この水酸基末端ポリプロピレンオキシドの水酸基に対して1.2倍当量のNaOMeメタノール溶液を添加してメタノールを留去し、更に塩化アリルを添加して末端の水酸基をアリル基に変換した。未反応の塩化アリルを減圧脱揮により除去した。得られた未精製のアリル末端ポリプロピレントリオール100重量部に対し、n−ヘキサン300重量部と、水300重量部を混合攪拌した後、遠心分離により水を除去し、得られたヘキサン溶液に更に水300重量部を混合攪拌し、再度遠心分離により水を除去した後、ヘキサンを減圧脱揮により除去した。以上により、末端がアリル基である数平均分子量約26,000の3官能ポリプロピレンオキシドを得た。
合成例1で得られた反応性ケイ素基含有ポリオキシプロピレン系重合体(A−1)100重量部、可塑剤として1−ドデシル−2−ピロリドン(ASHLAND社製、商品名:Surfadone LP−300)55重量部、表面処理膠質炭酸カルシウム(白石工業(株)製、商品名:白艶華CCR)120重量部、ルチル型酸化チタン(石原産業(株)製、商品名:タイペークR−820)20重量部、チクソ性付与剤(楠本化成工業(株)製、商品名:ディスパロン6500)2重量部、ヒンダードアミン系光安定剤(BASFジャパン(株)製、商品名:TINUVIN770)1重量部、ベンゾトリアゾール系紫外線吸収剤(BASFジャパン(株)製、商品名:TINUVIN326)1重量部を混合して充分混練りした後、3本ペイントロールに3回通して分散させた。この後、120℃で2時間減圧脱水を行い、50℃以下に冷却後、脱水剤としてビニルトリメトキシシラン(EVONIK社製、商品名:Dynasylan VTMO)2重量部、接着性付与剤のγ−(2−アミノエチル)アミノプロピルトリメトキシシラン(EVONIK社製、商品名:Dynasylan DAMO)3重量部、最後に硬化触媒としてジブチル錫ビスアセチルアセトナート(日東化成(株)製、商品名:ネオスタンU−220H)2重量部を加えて混練し、実質的に水分の存在しない状態で防湿性のあるカートリッジに密閉し、1成分型硬化性組成物を得た。
実施例1における1−ドデシル−2−ピロリドンの使用量を30重量部に変更し、フタル酸エステル系可塑剤であるジイソデシルフタレート(ジェイ・プラス社製、商品名:DIDP)25重量部を使用したこと以外は、実施例1と同様にして硬化性組成物を得た。
実施例1における1−ドデシル−2−ピロリドンの代わりに、ジイソデシルフタレートを55重量部を使用したこと以外は、実施例1と同様にして硬化性組成物を得た。
実施例2におけるジイソデシルフタレートの使用量を45重量部に変更し、N−メチル−2−ピロリドン(キシダ化学(株)製、試薬)10重量部を使用したこと以外は、実施例2と同様にして硬化性組成物を得た。
比較例2におけるジイソデシルフタレートを使用せず、N−メチル−2−ピロリドンの使用量を55重量部に変更したこと以外は、比較例2と同様にして硬化性組成物を得た。
合成例2で得られた反応性ケイ素基含有ポリオキシプロピレン系重合体と反応性ケイ素基含有アクリル系重合体の混合物(A−2)100重量部、可塑剤として1−ドデシル−2−ピロリドン(商品名:Surfadone LP−300)60重量部、表面処理膠質炭酸カルシウム(商品名:白艶華CCR)140重量部、チクソ性付与剤(商品名:ディスパロン6500)1重量部、ヒンダードアミン系光安定剤(商品名:TINUVIN770)1重量部、ベンゾトリアゾール系紫外線吸収剤(商品名:TINUVIN326)1重量部を混合して充分混練りした後、3本ペイントロールに3回通して分散させた。これに対して、脱水剤としてビニルトリメトキシシラン(商品名:Dynasylan VTMO)2重量部、接着性付与剤のγ−(2−アミノエチル)アミノプロピルトリメトキシシラン(EVONIK社製、商品名:Dynasylan DAMO)3重量部、硬化触媒としてジオクチル錫ジラウレート(日東化成(株)製、商品名:ネオスタンU−810)0.2重量部を加えて混練して硬化性組成物を得た。
実施例3のジオクチル錫ジラウレートを使用しない代わりに、フェニルグアニジン(日本カーバイド(株)製、商品名:PG−F)をブチルベンゼンスルホンアミド(富士アミドケミカル(株)製、商品名:トップサイザー7号)で溶解させた溶液(フェニルグアニジンの濃度は47wt%)3重量部使用すること以外は、実施例3と同様にして硬化性組成物を得た。
実施例3における1−ドデシル−2−ピロリドンの代わりに、ジイソデシルフタレートを60重量部を使用したこと以外は、実施例3と同様にして硬化性組成物を得た。
実施例3における1−ドデシル−2−ピロリドンの代わりに、N−メチル−2−ピロリドンを60重量部を使用したこと以外は、実施例3と同様にして硬化性組成物を得た。
23℃、50%RH条件下にて、トキメック社製BS型粘度計とローターNo.7を用いて、2rpmの粘度を測定した。
(深部硬化性)
23℃、50%RH条件下にて上記硬化性組成物を直径12mmのポリエチレン製チューブに泡が入らないようにして充填し、ヘラで表面が水平になるようにかきとって試験体とした。同条件に7日間放置した後、表層の硬化部をめくり取り、未硬化部分をきれいに取り去ってから、硬化した部分の厚みをノギスを用いて測定した。
(硬化物の引張物性)
上記硬化性組成物を厚さ3mmのシート状試験体にして23℃、50%RH条件に3日間、その後50℃乾燥機に4日間入れて硬化養生を行った。3号ダンベル型に打ち抜いた後、島津(株)製オートグラフを用いて引張速度200mm/分で引張試験を行い、50%モジュラス、100%モジュラス、破断時の強度、破断時の伸びを測定した。
(硬化物表面の耐候性)
硬化性組成物を厚さ3mmのシート状試験体にして23℃、50%RH条件に3日間、その後50℃乾燥機に4日間入れて硬化養生を行った。これを約30mm×40mmの長方形に切り取り、促進耐候性試験機(スガ試験機(株)製サンシャインウェザーメーター)に入れた。1500時間後にそれぞれの表面の様子を目視で観察し、初期と変化ないものを「変化なし」、クラック(ひび)が生じたものを「クラックあり」と記載した。
Claims (12)
- (A)シロキサン結合を形成することにより架橋し得るケイ素含有基を有する有機重合体100重量部、(B)N−アルキル−2−アザ−1−シクロアルカノンを20重量部を超えて300重量部未満を含有する硬化性組成物であって、(B)成分のアルキル基の炭素数が3〜22の範囲にある硬化性組成物。
- (B)成分がN−アルキル−2−ピロリドンである請求項1に記載の硬化性組成物。
- (A)成分の有機重合体の主鎖骨格が、ポリオキシアルキレン系重合体、飽和炭化水素系重合体、および(メタ)アクリル酸エステル系重合体からなる群から選択される少なくとも1種の重合体である請求項1〜2のいずれかに記載の硬化性組成物。
- ポリオキシアルキレン系重合体がポリオキシプロピレン系重合体である請求項3に記載の硬化性組成物。
- (A)成分のケイ素含有基が、トリメトキシシリル基、トリエトキシシリル基、ジメトキシメチルシリル基からなる群から選択される少なくとも1種である請求項1〜4のいずれかに記載の硬化性組成物。
- (C)成分としてアミノシランを含有することを特徴とする請求項1〜5のいずれかに記載の硬化性組成物。
- (D)成分として硬化触媒を含有することを特徴とする請求項1〜6のいずれかに記載の硬化性組成物。
- 請求項1〜7のいずれかに記載の硬化性組成物を用いてなるシーリング材。
- 請求項1〜7のいずれかに記載の硬化性組成物を用いてなる接着剤。
- 請求項1〜7のいずれかに記載の硬化性組成物を用いてなるコーティング材。
- 請求項1〜7のいずれかに記載の硬化性組成物を用いてなる防水材。
- 請求項1〜7のいずれかに記載の硬化性組成物を用いた硬化物。
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JP2010090381A (ja) * | 2008-10-06 | 2010-04-22 | Wacker Chemie Ag | 有機ケイ素化合物をベースとする架橋性材料 |
JP2013507485A (ja) * | 2009-10-07 | 2013-03-04 | アイエスピー インヴェストメンツ インコーポレイテッド | 可塑化ポリマー組成物 |
WO2013042702A1 (ja) * | 2011-09-22 | 2013-03-28 | 株式会社カネカ | 硬化性組成物およびその硬化物 |
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JP2010090381A (ja) * | 2008-10-06 | 2010-04-22 | Wacker Chemie Ag | 有機ケイ素化合物をベースとする架橋性材料 |
JP2013507485A (ja) * | 2009-10-07 | 2013-03-04 | アイエスピー インヴェストメンツ インコーポレイテッド | 可塑化ポリマー組成物 |
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US20180346770A1 (en) * | 2016-02-08 | 2018-12-06 | Kaneka Corporation | Curable composition having improved water-resistant adhesiveness |
JPWO2017138463A1 (ja) * | 2016-02-08 | 2018-12-27 | 株式会社カネカ | 耐水接着性が改良された硬化性組成物 |
EP3409730A4 (en) * | 2016-02-08 | 2019-01-16 | Kaneka Corporation | HARDENABLE COMPOSITION WITH IMPROVED WATER RESISTANT ADHESIVITY |
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