JP5469408B2 - 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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- JP5469408B2 JP5469408B2 JP2009187773A JP2009187773A JP5469408B2 JP 5469408 B2 JP5469408 B2 JP 5469408B2 JP 2009187773 A JP2009187773 A JP 2009187773A JP 2009187773 A JP2009187773 A JP 2009187773A JP 5469408 B2 JP5469408 B2 JP 5469408B2
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- 239000005052 trichlorosilane Substances 0.000 description 1
- CUXYLFPMQMFGPL-UYWAGRGNSA-N trichosanic acid Natural products CCCCC=C/C=C/C=CCCCCCCCC(=O)O CUXYLFPMQMFGPL-UYWAGRGNSA-N 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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 description 1
- QJOOZNCPHALTKK-UHFFFAOYSA-N trimethoxysilylmethanethiol Chemical compound CO[Si](CS)(OC)OC QJOOZNCPHALTKK-UHFFFAOYSA-N 0.000 description 1
- 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- QEEPNARXASYKDD-UHFFFAOYSA-J tris(7,7-dimethyloctanoyloxy)stannyl 7,7-dimethyloctanoate Chemical compound [Sn+4].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O QEEPNARXASYKDD-UHFFFAOYSA-J 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Landscapes
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
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、(B)カルボン酸および/またはカルボン酸金属塩、(C)一分子中に2個以上のアミノ基を有し、かつ反応性ケイ素基を有しないアミン化合物、(D)分子中に、一般式(1):
−C(CH3)2−NR1−C(CH3)2− (1)
および/または一般式(2)
−C(CH3)2−N(OR1)−C(CH3)2− (2)
(R1は炭素数1〜12の有機基を表す)で表される構造を有するピペリジン環を有するヒンダードアミン化合物、を含有する硬化性組成物、
(II).組成物中の有機錫化合物の含有量が0.02重量%未満であることを特徴とする(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)または(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)成分の有機重合体の主鎖骨格中に、一般式(3):
−NR2−C(=O)− (3)
(R2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とを特徴とする(I)〜(IV)のいずれかに記載の硬化性組成物、
(VI).(B)成分が、(B−1)カルボニル基に隣接する炭素原子が4級炭素であるカルボン酸および/または(B−2)カルボニル基に隣接する炭素原子が4級炭素であるカルボン酸金属塩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).(B−2)成分のカルボニル基に隣接する炭素原子が4級炭素であるカルボン酸金属塩が、カルボン酸錫塩であることを特徴とする(VI)に記載の硬化性組成物、
(VIII).(C)成分のアミン化合物が、ジアミン化合物であることを特徴とする(I)〜(VII)のいずれかに記載の硬化性組成物、
(IX).(C)成分のアミン化合物が、一分子中に1級アミノ基と3級アミノ基を一つずつもつジアミンであることを特徴とする(I)〜(VIII)のいずれかに記載の硬化性組成物、
(X).(A)成分100重量部に対して、分子中に一般式(4):
−C(CH3)2−NH−C(CH3)2− (4)
で表される構造を有するピペリジン環を有するヒンダードアミン化合物が1重量部未満であることを特徴とする(I)〜(IX)のいずれかに記載の硬化性組成物、
(XI).(D)成分のヒンダードアミン化合物の分子量が600以上4000以下であることを特徴とする(I)〜(X)のいずれかに記載の硬化性組成物、
(XII).(E)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)〜(XI)のいずれかに記載の硬化性組成物、
(XIII).(I)〜(XII)のいずれかに記載の硬化性組成物を用いてなる一液型シーリング材、
(XIV).(I)〜(XII)のいずれかに記載の硬化性組成物を用いてなる一液型接着剤、
(XV).(I)〜(XII)のいずれかに記載の硬化性組成物を用いてなる一液型床仕上げ用接着剤、
(XVI).(I)〜(XII)のいずれかに記載の硬化性組成物を硬化させた硬化物、
に関する。
−SiR3 3-aXa (5)
(R3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−(SiR4 2O)mSiR4 2−R5−SiX3 (6)
(Xは前記に同じ。2m+2個のR4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。R5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(6)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(6)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。
−R6−O− (7)
(R6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(7)におけるR6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(7)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(R7)(COOR8)− (8)
(R7は水素原子またはメチル基、R8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(9):
−CH2−C(R7)(COOR9)− (9)
(R7は前記に同じ、R9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。
−NR10−C(=O)− (10)
(R10は有機基または水素原子を表す)で表される基である。
W−R11−SiR3 3-aXa (11)
(R3、X、aは前記と同じ。R11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−R11−SiR3 3-aXa (12)
(R11、R3、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。
−NR2−C(=O)− (3)
(R2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望ましい。
−C(CH3)2−NR1−C(CH3)2− (1)
および/または一般式(2)
−C(CH3)2−N(OR1)−C(CH3)2− (2)
(R1は炭素数1以上の有機基を表し、炭素数1〜12の有機基が好ましい。)で表される構造を有するピペリジン環を有するヒンダードアミン化合物を用いる。これらのヒンダードアミン化合物を用いることで、硬化物表面への結晶物析出を抑制できる。このヒンダードアミン化合物は、高分子材料用のヒンダードアミン系光安定剤を使用することができる。ヒンダードアミン系光安定剤を使用すると硬化物の光酸化劣化を防止することができ、屋外に使用された場合等に劣化が生じる時間を遅らせることができ、長期間良好な状態を維持できる。
−C(CH3)2−NH−C(CH3)2− (4)
で表される構造を有するピペリジン環を有するヒンダードアミン化合物を添加した場合、硬化性組成物の耐候性は向上するものの、(B)成分と(C)成分を併用する組成物においては、硬化した表面に結晶が析出し易い傾向にある。よって、(A)成分100重量部に対して、分子中に一般式(4)で表される構造を有するピペリジン環を有するヒンダードアミン化合物の使用量は1重量部未満であることが好ましく、0.8重量部未満であることが好ましく、0.5重量部未満であることがより好ましい。
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。
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。
窒素雰囲気下、250L反応機に、CuBr(1.09kg)、アセトニトリル(11.4kg)、アクリル酸n−ブチル(26.0kg)及び2,5−ジブロモアジピン酸ジエチル(2.28kg)を加え、70〜80℃で30分程度撹拌した。これにペンタメチルジエチレントリアミンを加え、反応を開始した。反応開始30分後から2時間かけて、アクリル酸n−ブチル(104kg)を連続的に追加した。反応途中、ペンタメチルジエチレントリアミンを適宜添加し、内温70℃〜90℃となるようにした。ここまでで使用したペンタメチルジエチレントリアミン総量は220gであった。反応開始から4時間後、80℃で減圧下、加熱攪拌することにより揮発分を除去した。これにアセトニトリル(45.7kg)、1,7−オクタジエン(14.0kg)、ペンタメチルジエチレントリアミン(439g)を添加して、8時間撹拌を続けた。混合物を80℃で減圧下、加熱攪拌して揮発分を除去した。
合成例1で得られたシリル素基含有ポリオキシアルキレン系重合体(A−1)100重量部、表面処理膠質炭酸カルシウム(SOLVAY CHEMICALS社製、商品名:WINNOFIL SPM)120重量部、フタル酸エステル系可塑剤(EXXON CHEMICALS社製、商品名:Jayflex DIUP)55重量部、ルチル型酸化チタン(Kerr McGee社製、商品名:RFK−2)20重量部、チクソ性付与剤(Cray Valley社製、商品名:Crayvallac SLX)2重量部、ベンゾトリアゾール系紫外線吸収剤(CIBA社製、商品名:TINUVIN326)1重量部、−C(CH3)2−N(OC8H17)−C(CH3)2−で表される構造を有するピペリジン環を有するヒンダードアミン化合物(CIBA社製、商品名:TINUVIN123)1重量部までを計量し、スパチュラで荒く混合した後、3本ペイントロールに3回かけて、よく分散させたものを主剤とした。この主剤に、脱水剤の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)1.5重量部と、γ−アミノプロピルトリメトキシシラン(EVONIK社製、商品名:Dynasylan AMMO)1.5重量部、シラノール縮合触媒としてバーサチック酸(ジャパンエポキシレジン(株)製、商品名:バーサチック10)5重量部、および3−ジエチルアミノプロピルアミン(和光純薬工業(株)製試薬)0.5重量部を添加し、自転・公転ミキサー((株)シンキー製、商品名:あわとり錬太郎ARE−250)を用いて攪拌・脱泡を行い、硬化性組成物を得た。
実施例1におけるTINUVIN123の代わりに−C(CH3)2−NCH3−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物((株)ADEKA製、商品名:アデカスタブLA−63)を1重量部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TINUVIN123の代わりに−C(CH3)2−N(CH2−R)−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物((株)CIBA製、商品名:TINUVIN622)を1重量部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におけるバーサチック酸の代わりにバーサチック酸錫(日東化成工業(株)製、商品名:ネオスタンU−50)を5重量部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におけるバーサチック酸の代わりにバーサチック酸錫を5重量部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3におけるバーサチック酸の代わりにバーサチック酸錫を5重量部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TINUVIN326とTINUVIN123を使用しないこと以外は、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TINUVIN123を使用しないこと以外は、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TINUVIN326とTINUVIN123を使用せず、代わりに−C(CH3)2−NH−C(CH3)2−で表される構造を有するピペリジン環を有するヒンダードアミン化合物(三共ライフテック(株)製、商品名:サノールLS770)を1重量部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TINUVIN123の代わりにサノールLS770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4におけるTINUVIN123を使用しないこと以外は、実施例4と同様にして硬化性組成物を得た。
実施例4におけるTINUVIN123の代わりにサノールLS770を使用したこと以外は、実施例4と同様にして硬化性組成物を得た。
合成例1で得られたシリル基含有ポリオキシアルキレン系重合体(A−1)60重量部、合成例2で得られたシリル基含有アクリル系重合体(B−1)40重量部、表面処理膠質炭酸カルシウム(米国Specialty Minerals社製、商品名:Ultra Pflex)150重量部、表面処理重質炭酸カルシウム(米国J.M.Huber社製、商品名:Hubercarb Q3T)50重量部、アクリル系可塑剤(東亜合成(株)製、商品名:アルフォンUP−1020)50重量部、カーボンブラック(旭カーボン(株)製、商品名:旭#70)2重量部、チクソ性付与剤(楠本化成(株)製、商品名:ディスパロン6500)2重量部、ベンゾトリアゾール系紫外線吸収剤(チバ・ジャパン(株)社製、商品名:TINUVIN326)1重量部、−C(CH3)2−NCH3−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物((株)ADEKA製、商品名:アデカスタブLA−52)1重量部までを計量し、スパチュラで荒く混合した後、3本ペイントロールに3回かけて、よく分散させたものを主剤とした。この主剤に、脱水剤のビニルトリメトキシシラン(EVONIK社製、商品名:Dynasylan VTMO)3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重量部と、γ−グリシドキシプロピルトリメトキシシラン(EVONIK社製、商品名:Dynasylan GLYMO)3.2重量部、シラノール縮合触媒としてバーサチック酸(ジャパンエポキシレジン(株)製、商品名:バーサチック10)0.5重量部、バーサチック酸錫(日東化成工業(株)製、商品名:ネオスタンU−50)3.4重量部、および3−ジエチルアミノプロピルアミン(和光純薬工業(株)製試薬)0.5重量部を添加し、自転・公転ミキサーを用いて攪拌・脱泡を行い、硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−NCH3−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物((株)ADEKA製、商品名:アデカスタブLA−62)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−NCH3−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物((株)ADEKA製、商品名:アデカスタブLA−63)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−N(OC 11 H 23 )−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物((株)ADEKA製、商品名:アデカスタブLA−81)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−NCH3−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物((株)ADEKA製、商品名:アデカスタブLA−82)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−NCH3−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物(チバ・ジャパン(株)製、商品名:TINUVIN144)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−N(OC8H17)−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物(チバ・ジャパン(株)製、商品名:TINUVIN123)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−NCH3−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物(チバ・ジャパン(株)製、商品名:TINUVIN292)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−NCH3−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物(三共ライフテック(株)製、商品名:サノールLS765)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−NCH3−C(CH3)2−で表される構造を有するピペリジン環含有ヒンダードアミン化合物(チバ・ジャパン(株)製、商品名:Chimassorb 119FL)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52を使用しないこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7におけるアデカスタブLA−52の代わりに−C(CH3)2−NH−C(CH3)2−で表される構造を有するピペリジン環を有するヒンダードアミン化合物(三共ライフテック(株)製、商品名:サノールLS770)を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
実施例7において、さらにサノールLS770を1重量部使用したこと以外は、実施例7と同様にして硬化性組成物を得た。
23℃50%RHの恒温恒湿条件下で、上記の硬化性組成物を厚さ約3mmの型枠に充填し、表面を平面状に整えた。同条件で硬化物を保存し、7日後、56日後に硬化物表面の様子を目視で観察した。初期と同様に平滑な状態を維持していたものを良好、結晶が観察されたものは粒あり、と記した。
上記と同様に作成した厚さ約3mmの硬化物を、23℃50%RH条件下に3日、50℃条件で4日養生させた後、促進耐候性試験機であるサンシャインカーボンアーク灯式促進耐候試験機(スガ試験機株式会社製、型番S80)に設置した。ブラックパネル温度63℃、温度83℃、湿度50%、120分中水噴霧18分の条件で耐候性試験を行い、480時間後、960時間後、1200時間後の表面状態の様子を目視で観察した。初期と同様の状態を維持していたものを良好、表面にクラック(割れやヒビ)が観察されたものをクラックと記した。
Claims (16)
- (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、(B)カルボン酸および/またはカルボン酸金属塩、(C)一分子中に2個以上のアミノ基を有し、かつ反応性ケイ素基を有しないアミン化合物、(D)分子中に、一般式(1):
−C(CH3)2−NR1−C(CH3)2− (1)
および/または一般式(2)
−C(CH3)2−N(OR1)−C(CH3)2− (2)
(R1は炭素数1〜12の有機基を表す。ただし、一般式(1)、(2)中のNは、ピペリジン環のNに該当する。)で表される構造を有するピペリジン環を有するヒンダードアミン化合物、を含有し、前記ヒンダードアミン化合物の分子量が600以上4000以下である硬化性組成物。 - 組成物中の有機錫化合物の含有量が0.02重量%未満であることを特徴とする請求項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)成分の有機重合体の主鎖骨格中に、一般式(3):
−NR2−C(=O)− (3)
(R2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とを特徴とする請求項1〜4のいずれかに記載の硬化性組成物。 - (B)成分が、(B−1)カルボニル基に隣接する炭素原子が4級炭素であるカルボン酸および/または(B−2)カルボニル基に隣接する炭素原子が4級炭素であるカルボン酸金属塩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。
- (B−2)成分のカルボニル基に隣接する炭素原子が4級炭素であるカルボン酸金属塩が、カルボン酸錫塩であることを特徴とする請求項6に記載の硬化性組成物。
- (C)成分のアミン化合物が、ジアミン化合物であることを特徴とする請求項1〜7のいずれかに記載の硬化性組成物。
- (C)成分のアミン化合物が、一分子中に1級アミノ基と3級アミノ基を一つずつもつジアミンであることを特徴とする請求項1〜8のいずれかに記載の硬化性組成物。
- (A)成分100重量部に対して、分子中に一般式(4):
−C(CH3)2−NH−C(CH3)2− (4)
(ただし、一般式(4)中のNは、ピペリジン環のNに該当する。)で表される構造を有するピペリジン環を有するヒンダードアミン化合物が1重量部未満であることを特徴とする請求項1〜9のいずれかに記載の硬化性組成物。 - (D)成分のヒンダードアミン化合物の分子量が600以上4000以下であることを特徴とする請求項1〜10のいずれかに記載の硬化性組成物。
- (E)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1〜11のいずれかに記載の硬化性組成物。
- 請求項1〜12のいずれかに記載の硬化性組成物を用いてなる一液型シーリング材。
- 請求項1〜12のいずれかに記載の硬化性組成物を用いてなる一液型接着剤。
- 請求項1〜12のいずれかに記載の硬化性組成物を用いてなる一液型床仕上げ用接着剤。
- 請求項1〜12のいずれかに記載の硬化性組成物を硬化させた硬化物。
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