JP4819675B2 - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
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- JP4819675B2 JP4819675B2 JP2006512948A JP2006512948A JP4819675B2 JP 4819675 B2 JP4819675 B2 JP 4819675B2 JP 2006512948 A JP2006512948 A JP 2006512948A JP 2006512948 A JP2006512948 A JP 2006512948A JP 4819675 B2 JP4819675 B2 JP 4819675B2
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
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- 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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- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-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
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- 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
- XSIGLRIVXRKQRA-UHFFFAOYSA-N triethoxysilylmethanethiol Chemical compound CCO[Si](CS)(OCC)OCC XSIGLRIVXRKQRA-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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- 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
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-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
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/014—Stabilisers against oxidation, heat, light or ozone
-
- 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
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- 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
- C08K5/544—Silicon-containing compounds containing nitrogen
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Description
(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ポリオキシアルキレン系重合体および/または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(メタ)アクリル酸エステル系重合体、
(B)下記の一般式(1)または(2)で表されるチタニウムキレート、および
(C)アマイドワックス系チクソ性付与剤、
を含有することを特徴とする硬化性組成物に関する。
一般式(1):
一般式(2):
好ましくは、重合体(A)は、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ポリオキシプロピレン系重合体および/または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(メタ)アクリル酸エステル系重合体である。
−(SiR5 2-bXbO)m−SiR6 3-aXa (3)
(式中、R5およびR6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(R’)3SiO−(R’は、それぞれ独立に、炭素原子数1から20の置換あるいは非置換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、水酸基または加水分解性基である。さらに、bは0、1、2のいずれかであり、aは0、1、2、3のいずれかであり、bとaとが同時に0になることはない。また、mは0または1〜19の整数である)で表される基があげられる。
−SiR6 3-cXc (4)
(式中、R6、Xは前記と同じ。cは1〜3の整数)で表される反応性ケイ素基が、入手が容易であるので好ましい。
−R7−O− (5)
(式中、R7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(5)におけるR7は、炭素原子数1から14の、さらには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(5)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(R8)(COOR9)− (6)
(式中、R8は水素原子またはメチル基、R9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(7):
−CH2−C(R8)(COOR10)− (7)
(式中、R8は前記に同じ、R10は炭素原子数10以上のアルキル基を示す)で表される炭素原子数10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。
−NR11−C(=O)− (8)
(R11は水素原子または置換あるいは非置換の有機基を表す)で表される基である。
W−R12−SiR6 3-cXc (9)
(ただし、式中、R6、X、cは前記と同じ。R12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の置換もしくは非置換の2価の炭化水素基である。Wは水酸基、カルボキシル基、メルカプト基およびアミノ基(非置換または一置換)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、などが挙げられる。
O=C=N−R12−SiR6 3-cXc (10)
(ただし、式中R6、R12、X、c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などが挙げられる。
このチタニウムキレートは、(A)成分である有機重合体の硬化触媒として機能する。従来、(A)成分である反応性ケイ素基を有する有機重合体の硬化触媒として、ジブチル錫ジラウレートやジブチル錫ビス(アセチルアセトネート)などの有機錫化合物が用いられているが、本発明のチタニウムキレート(B)を用いることにより、非有機錫触媒でありながら、実用的な硬化特性を有する硬化性組成物が得られる。更に、キレート配位子を有しない他のチタン触媒を用いた場合と比較して、硬化性および貯蔵安定性が良好である。更に、有機錫触媒などの他の硬化触媒を用いた場合と比較して、アクリル樹脂などの難接着有機系被着体に対する接着性を高めることができる。
チタニウムアクリレートトリイソプロポキシド、チタニウムメタクリレートトリイソプロポキシド、チタニウムジメタクリレートジイソプロポキシド、チタニウムイソプロポキシドトリメタクリレート、チタニウムヘキサノエートトリイソプロポキシド、チタニウムステアレートトリイソプロポキシド、などのチタニウムアシレート;
チタニウムクロライドトリイソプロポキシド、チタニウムジクロライドジイソプロポキシド、チタニウムイソプロポキシドトリクロライド、チタニウムブロマイドトリイソプロポキシド、チタニウムフルオライドトリイソプロポキシド、チタニウムクロライドトリエトキシド、チタニウムクロライドトリブトキシド、などのハロゲン化チタネート;
チタニウムジイソプロポキシドビス(トリエタノールアミネート)、チタニウムテトラキス(エチルアセトアセテート)、チタニウムテトラキス(アセチルアセトネート)、チタニウムトリス(ジオクチルフォスフェート)イソプロポキシド、チタニウムトリス(ドデシルベンゼンスルフォネート)イソプロポキシド、ジヒドロキシチタニウムビスラクテート、などのその他のチタネート;などが挙げられる。
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〜、第106頁〜、第117頁〜)に詳細な例示があり、これらを単独又は混合し、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0.1〜20重量部、好ましくは0.5〜10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グリコールを開始剤とし、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25,500(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。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基末端ポリプロピレンオキシド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25,500の2官能ポリプロピレンオキシドを得た。
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を重合させて得られた数平均分子量約19,000の水酸基末端ポリプロピレンオキシドを用い、合成例1と同様の手順でアリル末端ポリプロピレンオキシドを得た。このアリル末端ポリプロピレンオキシドに対し、合成例1と同様の手順で、メチルジメトキシシラン1.35重量部と反応させ、末端に平均1.7個のメチルジメトキシシリル基を有するポリオキシプロピレン系重合体(A−2)を得た。
105℃に加熱した下記単量体混合物の2−ブタノール溶液に、重合開始剤として2,2’−アゾビス(2−メチルブチロニトリル)を溶かした溶液を5時間かけて滴下し、その後1時間「後重合」を行って(メタ)アクリル酸エステル系重合体(A−3)を得た。
合成例2で得られた重合体(A−2)と合成例3で得られた重合体(A−3)を固形分重量比80/20で混合した後、溶剤を留去して無溶剤ポリマー(A−4)を得た。
表1に示す処方にしたがって、合成例1または合成例4で得られた反応性ケイ素基を有する有機重合体(A−1,A−4)100重量部、表面処理膠質炭酸カルシウム(白石工業製、白艶華CCR)120重量部、酸化チタン(石原産業製、タイペークR−820)20重量部、可塑剤ジイソデシルフタレート(新日本理化製、サンソサイザーDIDP)55重量部、アマイドワックス系チクソ性付与剤(楠本化成製、ディスパロン6500)または水添ひまし油系チクソ性付与剤(楠本化成製、ディスパロン305)を表1に示す重量部、光安定剤(三共製、サノールLS765)1重量部、紫外線吸収剤(住友化学製、スミソーブ400)1重量部、酸化防止剤(チバ・スペシャルティ・ケミカルズ製、イルガノックス1010)1重量部、ビニルトリメトキシシラン(東レ・ダウコーニング・シリコーン製、A−171)2重量部、N−(β−アミノエチル)−γ−アミノプロピルトリメトキシシラン(東レ・ダウコーニング・シリコーン製、A−1120)3重量部、および硬化触媒として(B)成分のチタニウムジイソプロポキシドビス(エチルアセトアセテート)(松本交商製、オルガチックスTC−750)7.5重量部、もしくは、(B)成分以外のチタン触媒であるチタニウムテトライソプロポキシド(和光純薬工業製)5重量部または有機錫触媒であるジブチルスズビス(アセチルアセトネート)(日東化成製、ネオスタンU−220)1重量部を添加し、脱水条件化にて実質的に水分の存在しない状態で混練した後、防湿性の容器に密閉し、1液型硬化性組成物を得た。(チタン触媒の添加部数は、組成物中のTi原子のmol数が同一となるように調整した。)
このカートリッジから各1液型硬化性組成物を押し出し、押し出した硬化性組成物を厚さ約5mmの型枠にスパチュラを用いて充填し、表面を平面状に整えた。この時間を硬化開始時間とし、表面をスパチュラで触り、スパチュラに配合物が付着しなくなった時間を皮張り時間として測定を行った。皮張り時間は、23℃50%RHの条件下で測定した。
Claims (6)
- (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ポリオキシアルキレン系重合体および/または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(メタ)アクリル酸エステル系重合体、
(B)下記の一般式(1)または(2)で表されるチタニウムキレート、および
(C)アマイドワックス系チクソ性付与剤、
を含有することを特徴とする硬化性組成物。
一般式(1):
一般式(2):
- 重合体(A)が、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ポリオキシプロピレン系重合体および/または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(メタ)アクリル酸エステル系重合体である請求項1に記載の硬化性組成物。
- 重合体(A)のガラス転移温度が、20℃以下であることを特徴とする請求項1または2に記載の硬化性組成物。
- 重合体(A)100重量部に対して、0.1〜20重量部のチタニウムキレート(B)、0.1〜20重量部のアマイドワックス系チクソ性付与剤(C)を含有する請求項1から3のいずれかに記載の硬化性組成物。
- 請求項1から4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から4のいずれかに記載の硬化性組成物を用いてなる接着剤。
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