JPWO2012081483A1 - 反応性可塑剤、およびこれを含む硬化性組成物 - Google Patents
反応性可塑剤、およびこれを含む硬化性組成物 Download PDFInfo
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- JPWO2012081483A1 JPWO2012081483A1 JP2012548759A JP2012548759A JPWO2012081483A1 JP WO2012081483 A1 JPWO2012081483 A1 JP WO2012081483A1 JP 2012548759 A JP2012548759 A JP 2012548759A JP 2012548759 A JP2012548759 A JP 2012548759A JP WO2012081483 A1 JPWO2012081483 A1 JP WO2012081483A1
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- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- MTBVDKSFTCGOTN-UHFFFAOYSA-N octane pentane-2,4-dione tin(4+) Chemical compound [Sn+4].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O.CCCCCCC[CH2-].CCCCCCC[CH2-] MTBVDKSFTCGOTN-UHFFFAOYSA-N 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
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- 125000005371 silicon functional group Chemical group 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- ACECBHHKGNTVPB-UHFFFAOYSA-N silylformic acid Chemical class OC([SiH3])=O ACECBHHKGNTVPB-UHFFFAOYSA-N 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
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- 238000009864 tensile test Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000002966 varnish 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
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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- 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
- C08G65/26—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 from cyclic ethers and other compounds
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- C08G65/32—Polymers modified by chemical after-treatment
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Abstract
Description
(I).数平均分子量が800〜15,000で、一般式(1):
−Y−R1−CH(CH3)−CH2−Si(R2 3-a)Xa (1)
(式中、R1は水素、炭素、及び窒素からなる群より選択される1種以上を構成原子として含有する炭素数1から20の2価の有機基を示し、R2は炭素数1から20のアルキル基、炭素数6から20のアリール基、炭素数7から20のアラルキル基または−OSi(R’)3で示されるトリオルガノシロキシ基を示す。ここでR’は炭素数1から20の一価の炭化水素基であり3個のR’は同一であってもよく、異なっていてもよい。Xは水酸基または加水分解性基を示し、Xが二個以上存在するとき、それらは同一であってもよく、異なっていてもよい。Yはヘテロ原子であり、酸素原子または窒素原子から選択される。aは1〜3の整数である)で示される反応性ケイ素基を一分子中に平均して0.5〜1.2個未満含有する有機重合体(A)、
(II).有機重合体(A)の主鎖が、直鎖状であることを特徴とする、(I)に記載の有機重合体、
(III).有機重合体(A)の反応性ケイ素基が、実質的に有機重合体の片方の末端にのみ存在することを特徴とする、(I)または(II)に記載の有機重合体、
(IV).一般式(1)中に記載のR1がCH2であることを特徴とする、(I)〜(III)のいずれかに記載の有機重合体、
(V).一般式(1)中に記載のYが酸素原子であることを特徴とする、(I)〜(IV)のいずれかに記載の有機重合体、
(VI).一般式(1)中に記載のaが2であることを特徴とする、(I)〜(V)のいずれかに記載の有機重合体、
(VII).有機重合体(A)の主鎖がポリオキシアルキレン系重合体、ポリアクリル系重合体、炭化水素系重合体のいずれか又は複数であることを特徴とする、(I)〜(VI)のいずれかに記載の有機重合体、
(VIII).有機重合体(A)の主鎖がポリオキシプロピレン系重合体であることを特徴とする、(I)〜(VII)のいずれかに記載の有機重合体、
(IX).有機重合体(A)が、1分子中に水酸基を1個のみ有する開始剤を用いて、複合金属シアン化物錯体触媒存在下でプロピレンオキシドを反応させたポリオキシプロピレン系重合体に、一般式(1)で示される反応性ケイ素基を導入して得られることを特徴とする、(I)〜(VIII)のいずれかに記載の有機重合体、
(X).有機重合体(A)が、1分子中に水酸基を2個以上有する開始剤と、1分子中に水酸基を1個のみ有する開始剤を併用し、複合金属シアン化物錯体触媒存在下でプロピレンオキシドを反応させたポリオキシプロピレン系重合体に、一般式(1)で示される反応性ケイ素基を導入して得られることを特徴とする、(I)〜(IX)のいずれかに記載の有機重合体、
(XI).有機重合体(A)の反応性ケイ素基が、メチルジメトキシシリル基であることを特徴とする、(I)〜(X)のいずれかに記載の有機重合体、
(XII).(I)〜(XI)のいずれかに記載の有機重合体(A)と、数平均分子量が5,000〜50,000で、反応性ケイ素基を1分子中に平均して1.2個〜5個含有する有機重合体(B)、を含む硬化性組成物、
(XIII).有機重合体(B)の主鎖がポリオキシアルキレン系重合体、ポリアクリル系重合体、炭化水素系重合体のいずれか又は複数であることを特徴とする、(XII)に記載の硬化性組成物、
(XIV).有機重合体(B)の反応性ケイ素基が、メチルジメトキシシリル基であることを特徴とする、(XII)〜(XIII)のいずれかに記載の硬化性組成物、
(XV).有機重合体(A)100重量部に対して、有機重合体(B)を20〜2000重量部使用することを特徴とする(XII)〜(XIV)のいずれかに記載の硬化性組成物、
(XVI).フタル酸エステル系可塑剤を、有機重合体(A)100重量部に対して1〜20重量部使用することを特徴とする、(XII)〜(XV)のいずれかに記載の硬化性組成物、
(XVII).(XII)〜(XVI)のいずれかに記載の硬化性組成物を用いた建築用シーリング材、
(XVIII).(XII)〜(XVI)のいずれかに記載の硬化性組成物を用いたサイディングボードに施工されるシーリング材、
(XIX).(XII)〜(XVI)のいずれかに記載の硬化性組成物を用いた石目地用シーリング材、
(XX).(XII)〜(XVI)のいずれかに記載の硬化性組成物を硬化させた硬化物であって、下記方法で評価した珪砂付着量の値が10mg/cm2以下であることを特徴とする硬化物:
(評価方法)硬化性組成物を23℃、50%RH条件下で3日間放置した後、50℃で4日間硬化させる。当該シートの表面に、水性アクリルエマルション塗料(エスケー化研(株)製、商品名「プリーズコート」)を塗布し、さらに23℃、50%RH条件下で7日間放置する。7日間放置の後、珪砂として新東陶料(株)製67ブラックを当該シートの表面に均一に塗布する。3時間経過後に、刷毛で珪砂を軽く拭き取った時の単位面積当たりの付着量(mg/cm2)を測定する、
に関する。
−Y−R1−CH(CH3)−CH2−Si(R2 3-a)Xa (1)
(式中、R1は水素、炭素、及び窒素からなる群より選択される1種以上を構成原子として含有する炭素数1から20の2価の有機基を示し、R2は炭素数1から20のアルキル基、炭素数6から20のアリール基、炭素数7から20のアラルキル基または−OSi(R’)3で示されるトリオルガノシロキシ基を示す。ここでR’は炭素数1から20の一価の炭化水素基であり3個のR’は同一であってもよく、異なっていてもよい。Xは水酸基または加水分解性基を示し、Xが二個以上存在するとき、それらは同一であってもよく、異なっていてもよい。Yはヘテロ原子であり、酸素原子または窒素原子から選択される。aは1〜3の整数である)で示される基である。
−SiR2 3-aXa (2)
(R2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1〜3の整数である)で表される基があげられる。
H−(SiR3 2O)mSiR3 2−R4−SiX3 (3)
(Xは前記に同じ。2m+2個のR3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。R4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(3)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(3)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。
−R5−O− (4)
(R5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(4)におけるR5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(4)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。特にシーリング材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(R6)(COOR7)− (5)
(R6は水素原子またはメチル基、R7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(6):
−CH2−C(R6)(COOR8)− (6)
(R6は前記に同じ、R8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。
−NR9−C(=O)− (7)
(R9は有機基または水素原子を表す)で表される基である。
W−R10−SiR2 3-aXa (8)
(R2、X、aは前記と同じ。R10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−R10−SiR2 3-aXa (9)
(R10、R2、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。
−NR11−C(=O)− (10)
(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。
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)成分と(B)成分の合計100重量部に対して、0.1から10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、(A)成分と(B)成分の合計100重量部に対して0.1から10重量部、好ましくは0.5から5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、10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1,200のポリオキシプロピレングリコールモノブチルエーテル(三洋化成工業(株)製、商品名:ニューポールLB−285)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7,500(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、この水酸基を有する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3−クロロ−2−メチル−1−プロペンを添加して末端の水酸基をメタリル基に変換した。
数平均分子量14,600(上記と同じ方法にて測定)のポリオキシプロピレングリコールとn−ブタノールをそれぞれ重量比で10:1の割合で混合したものを開始剤とし、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8,000(上記と同じ方法にて測定)のポリプロピレンオキシドを得た。続いて、この水酸基を有する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3−クロロ−2−メチル−1−プロペンを添加して末端の水酸基をメタリル基に変換した。
分子量約1,200のポリオキシプロピレングリコールモノブチルエーテル(三洋化成工業(株)製、商品名:ニューポールLB−285)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7,500(上記と同じ方法にて測定)のポリプロピレンオキシドを得た。続いて、この水酸基を有する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。
ポリ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7,500(上記と同じ方法にて測定)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。
数平均分子量14,600(上記と同じ方法にて測定)のポリオキシプロピレングリコールとn−ブタノールをそれぞれ重量比で10:1の割合で混合したものを開始剤とし、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8,000(上記と同じ方法にて測定)のポリプロピレンオキシドを得た。続いて、この水酸基を有する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3−クロロ−2−メチル−1−プロペンを添加して末端の水酸基をメタリル基に変換した。
ポリ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28,500(上記と同じ方法にて測定)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。
ポリ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28,500(上記と同じ方法にて測定)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3−クロロ−2−メチル−1−プロペンを添加して末端の水酸基をメタリル基に変換した。
合成例6で得られたポリマーP−1を100重量部、合成例1で得られたポリマーAを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、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、タレ防止剤(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(BASFジャパン(株)製、商品名:TINUVIN326)1重量部、ヒンダードアミン系光安定剤(三共ライフテック(株)製、商品名:サノールLS770)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、23℃50%RH条件下に一晩置いたものを主剤とした。この主剤の粘度を測定した後、脱水剤としてビニルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ社製、商品名:Silquest A−171)2重量部、接着性付与剤としてγ−(2−アミノエチル)アミノプロピルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ社製、商品名:Silquest A−1120)3重量部、硬化触媒としてジブチル錫ビスアセチルアセトナート(日東化成工業(株)製、商品名:ネオスタンU−220H)2重量部を加えて混練し、硬化性組成物を得た。この硬化性組成物の皮張り時間、1日後と3日後と7日後の残留タック(表面のべたつき)、ダンベル引張物性、塗料汚染性を下記の方法に従って測定した。
実施例1におけるポリマーAの代わりに、表1に示すポリマーもしくは可塑剤を用いること以外は、実施例1と同様の方法で硬化性組成物を得て、同様の評価を行った。
合成例6で得られたポリマーP−1を70重量部、合成例2で得られたポリマーBを30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、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、フタル酸エステル系可塑剤(ジェイ・プラス(株)製、商品名:DIDP)55重量部、タレ防止剤(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(BASFジャパン(株)製、商品名:TINUVIN326)1重量部、ヒンダードアミン系光安定剤(三共ライフテック(株)製、商品名:サノールLS770)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、23℃50%RH条件下に一晩置いたものを主剤とした。この主剤の粘度を測定した後、脱水剤としてビニルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ社製、商品名:Silquest A−171)2重量部、接着性付与剤としてγ−(2−アミノエチル)アミノプロピルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ社製、商品名:Silquest A−1120)3重量部、硬化触媒としてジブチル錫ジラウレート(日東化成工業(株)製、商品名:ネオスタンU−100)1重量部を加えて混練し、硬化性組成物を得た。この硬化性組成物の1日後と3日後と7日後の残留タック(表面のべたつき)、ダンベル引張物性、復元性を下記の方法に従って測定した。
実施例3におけるポリマーP−1とポリマーBの代わりに、表2に示すポリマーを用いること以外は、実施例3と同様の方法で硬化性組成物を得て、同様の評価を行った。
実施例3におけるポリマーP−1を100部使用し、ポリマーBの量または種類を表2に示す通りに変更し、フタル酸エステル系可塑剤を使用しないこと以外は、実施例3と同様の方法で硬化性組成物を得て、同様の評価を行った。
100ml容のカップに泡が入らないように主剤を充填した。BS型粘度計(トキメック社製)とローターNo.7を用いて、23℃50%RH条件下で各組成物の1rpm、2rpm、10rpmでの粘度を測定した。
23℃、50%RH条件下にて上記硬化性組成物を厚みが約3mmになるようヘラを用いて伸ばし、ミクロスパテュラを用いて経時で硬化性組成物の表面に軽く触れ、組成物がミクロスパテュラについてこなくなるまでの時間を測定した。
上記で得られた硬化性組成物を厚み約3mmに伸ばし、23℃、50%RH条件下で放置した。1日後、3日後、7日後にその表面を指先で軽く触れ、べたつき程度を評価した。べたつき感は8段階の数字で表現し、8は全くべたつきが感じられない、5は少しべたつき感があり、3はべたつき感がきつい、1は硬化していない、を目安に判定した。
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、さらに50℃乾燥機に4日間入れることで完全に硬化させた。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(それぞれ、M50、M100、TB、EBと示す)を測定した。
それぞれの硬化性組成物を用いて、厚さ3mmのシート状試験体を作成し、23℃、50%RH条件下で3日間放置した後、50℃で4日間硬化させた。このシートの表面に、水性アクリルエマルション塗料(エスケー化研(株)製、商品名「プリーズコート」)を塗布して、さらに、23℃、50%RH条件下で7日間放置した。その後、珪砂として新東陶料(株)製67ブラックを使用してサンプル表面に均一に塗布した。3時間経過後に、刷毛で珪砂を軽く拭き取った時の状態を観察した。塗料汚染性は5段階の数字で表現し、5:珪砂付着が全くなし(2mg/cm2未満)、3:珪砂が少し付着している(10mg/cm2以上かつ20mg/cm2未満)、1:一面に珪砂が多数付着(30mg/cm2以上)、を目安に判定した。
上記の引張物性と同様の作成方法で得た3号ダンベル型試験体について、60%伸張して23℃50%RH条件で24時間保持した。その後、伸張を開放し、同条件で放置して1時間後と24時間後に復元した程度を測定した。完全に元の状態に戻った場合は復元性100%、全く復元しなかった場合は0%となる。
Claims (20)
- 数平均分子量が800〜15,000で、一般式(1):
−Y−R1−CH(CH3)−CH2−Si(R2 3-a)Xa (1)
(式中、R1は水素、炭素、及び窒素からなる群より選択される1種以上を構成原子として含有する炭素数1から20の2価の有機基を示し、R2は炭素数1から20のアルキル基、炭素数6から20のアリール基、炭素数7から20のアラルキル基または−OSi(R’)3で示されるトリオルガノシロキシ基を示す。ここでR’は炭素数1から20の一価の炭化水素基であり3個のR’は同一であってもよく、異なっていてもよい。Xは水酸基または加水分解性基を示し、Xが二個以上存在するとき、それらは同一であってもよく、異なっていてもよい。Yはヘテロ原子であり、酸素原子または窒素原子から選択される。aは1〜3の整数である。)で示される反応性ケイ素基を一分子中に平均して0.5〜1.2個未満含有する有機重合体(A)。 - 有機重合体(A)の主鎖が、直鎖状であることを特徴とする、請求項1に記載の有機重合体。
- 有機重合体(A)の反応性ケイ素基が、実質的に有機重合体の片方の末端にのみ存在することを特徴とする、請求項1または請求項2に記載の有機重合体。
- 一般式(1)中に記載のR1がCH2であることを特徴とする、請求項1〜3のいずれかに記載の有機重合体。
- 一般式(1)中に記載のYが酸素原子であることを特徴とする、請求項1〜4のいずれかに記載の有機重合体。
- 一般式(1)中に記載のaが2であることを特徴とする、請求項1〜5のいずれかに記載の有機重合体。
- 有機重合体(A)の主鎖がポリオキシアルキレン系重合体、ポリアクリル系重合体、炭化水素系重合体のいずれか又は複数であることを特徴とする、請求項1〜6のいずれかに記載の有機重合体。
- 有機重合体(A)の主鎖がポリオキシプロピレン系重合体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有機重合体。
- 有機重合体(A)が、1分子中に水酸基を1個のみ有する開始剤を用いて、複合金属シアン化物錯体触媒存在下でプロピレンオキシドを反応させたポリオキシプロピレン系重合体に、一般式(1)で示される反応性ケイ素基を導入して得られることを特徴とする、請求項1〜8のいずれかに記載の有機重合体。
- 有機重合体(A)が、1分子中に水酸基を2個以上有する開始剤と、1分子中に水酸基を1個のみ有する開始剤を併用し、複合金属シアン化物錯体触媒存在下でプロピレンオキシドを反応させたポリオキシプロピレン系重合体に、一般式(1)で示される反応性ケイ素基を導入して得られることを特徴とする、請求項1〜9のいずれかに記載の有機重合体。
- 有機重合体(A)の反応性ケイ素基が、メチルジメトキシシリル基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有機重合体。
- 請求項1〜11のいずれかに記載の有機重合体(A)と、数平均分子量が5,000〜50,000で、反応性ケイ素基を1分子中に平均して1.2個〜5個含有する有機重合体(B)、を含む硬化性組成物。
- 有機重合体(B)の主鎖がポリオキシアルキレン系重合体、ポリアクリル系重合体、炭化水素系重合体のいずれか又は複数であることを特徴とする、請求項12に記載の硬化性組成物。
- 有機重合体(B)の反応性ケイ素基が、メチルジメトキシシリル基であることを特徴とする、請求項12〜13のいずれかに記載の硬化性組成物。
- 有機重合体(A)100重量部に対して、有機重合体(B)を20〜2000重量部使用することを特徴とする請求項12〜14のいずれかに記載の硬化性組成物。
- フタル酸エステル系可塑剤を、有機重合体(A)100重量部に対して1〜20重量部使用することを特徴とする、請求項12〜15のいずれかに記載の硬化性組成物。
- 請求項12〜16のいずれかに記載の硬化性組成物を用いた建築用シーリング材。
- 請求項12〜16のいずれかに記載の硬化性組成物を用いたサイディングボードに施工されるシーリング材。
- 請求項12〜16のいずれかに記載の硬化性組成物を用いた石目地用シーリング材。
- 請求項12〜16のいずれかに記載の硬化性組成物を硬化させた硬化物であって、下記方法で評価した珪砂付着量の値が10mg/cm2以下であることを特徴とする硬化物:
(評価方法)硬化性組成物を23℃、50%RH条件下で3日間放置した後、50℃で4日間硬化させる。当該シートの表面に、水性アクリルエマルション塗料(エスケー化研(株)製、商品名「プリーズコート」)を塗布し、さらに23℃、50%RH条件下で7日間放置する。7日間放置の後、珪砂として新東陶料(株)製67ブラックを当該シートの表面に均一に塗布する。3時間経過後に、刷毛で珪砂を軽く拭き取った時の単位面積当たりの付着量(mg/cm2)を測定する。
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