JPWO2012070476A1 - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
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- JPWO2012070476A1 JPWO2012070476A1 JP2012545712A JP2012545712A JPWO2012070476A1 JP WO2012070476 A1 JPWO2012070476 A1 JP WO2012070476A1 JP 2012545712 A JP2012545712 A JP 2012545712A JP 2012545712 A JP2012545712 A JP 2012545712A JP WO2012070476 A1 JPWO2012070476 A1 JP WO2012070476A1
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- reactive silicon
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- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000768 polyamine Chemical class 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
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- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 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 compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229920006298 saran Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 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
- 239000010454 slate Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000600 sorbitol Chemical group 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 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
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000001911 terphenyls 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000004448 titration Methods 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
- 230000002463 transducing effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-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
- 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
- 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
- 150000003755 zirconium compounds Chemical class 0.000 description 1
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C08L101/10—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
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- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/10—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
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- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/16—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
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Abstract
Description
(1).(A)数平均分子量が2,000〜6,000であり、1分子中に反応性ケイ素基を1.3〜5個含有する反応性ケイ素基含有有機重合体100重量部、及び、(C)可塑剤0〜40重量部を含有する硬化性組成物、
(2).(A)成分である反応性ケイ素基含有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であることを特徴とする(1)に記載の硬化性組成物、
(3).(A)成分である反応性ケイ素基含有有機重合体の主鎖構造が、少なくとも1つ以上の分岐鎖を有していることを特徴とする(1)または(2)に記載の硬化性組成物、
(4).(A)成分である反応性ケイ素基含有有機重合体が、1分子中に反応性ケイ素基を2〜5個含有することを特徴とする請求項1〜3のいずれか1項に記載の硬化性組成物、
(5).(C)成分である可塑剤を含有しないことを特徴とする(1)〜(4)のいずれか1項に記載の硬化性組成物、
(6).組成物中に、数平均分子量が8,000〜50,000であり1分子中に反応性ケイ素基を1.3〜5個含有する反応性ケイ素基含有有機重合体(B)が含有されていることを特徴とする(1)〜(5)のいずれか1項に記載の硬化性組成物、
(7).(B)成分である反応性ケイ素基含有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であることを特徴とする(6)に記載の硬化性組成物、
(8).(1)〜(7)のいずれか1項に記載の硬化性組成物を成分として含む接着剤、
(9).(1)〜(7)のいずれか1項に記載の硬化性組成物を成分として含む床用接着剤、
(10).(1)〜(5)のいずれか1項に記載の硬化性組成物を成分として含むタイル張り用接着剤、
(11).(6)〜(7)のいずれか1項に記載の硬化性組成物を成分として含むタイル張り用接着剤、
(12).(1)〜(7)のいずれか1項に記載の硬化性組成物を硬化させて得られるコーティング剤、
(13).(1)〜(7)のいずれか1項に記載の硬化性組成物を硬化させて得られる硬化物、
に関する。
本発明に用いる反応性ケイ素基を有する有機重合体(A)の主鎖骨格は特に制限はなく、各種の主鎖骨格を持つものを使用することができるが、得られる組成物の硬化性や接着性に優れることから、水素原子、炭素原子、窒素原子、酸素原子、硫黄原子から選択される1つ以上からなることが好ましい。
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。
−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。
−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望ましい。
可塑剤の添加により、硬化性組成物の粘度やスランプ性および硬化性組成物を硬化して得られる硬化物の硬度、引張り強度、伸びなどの機械特性が調整できる。可塑剤の具体例としては、ジブチルフタレート、ジイソノニルフタレート(DINP)、ジヘプチルフタレート、ジ(2−エチルヘキシル)フタレート、ジイソデシルフタレート(DIDP)、ブチルベンジルフタレートなどのフタル酸エステル化合物;ビス(2−エチルヘキシル)−1,4−ベンゼンジカルボキシレートなどのテレフタル酸エステル化合物(具体的には、商品名:EASTMAN168(EASTMAN CHEMICAL製));1,2−シクロヘキサンジカルボン酸ジイソノニルエステルなどの非フタル酸エステル化合物(具体的には、商品名:Hexamoll DINCH(BASF製));アジピン酸ジオクチル、セバシン酸ジオクチル、セバシン酸ジブチル、コハク酸ジイソデシル、アセチルクエン酸トリブチルなどの脂肪族多価カルボン酸エステル化合物;オレイン酸ブチル、アセチルリシノール酸メチルなどの不飽和脂肪酸エステル化合物;アルキルスルホン酸フェニルエステル(具体的には、商品名:Mesamoll(LANXESS製));トリクレジルホスフェート、トリブチルホスフェートなどのリン酸エステル化合物;トリメリット酸エステル化合物;塩素化パラフィン;アルキルジフェニル、部分水添ターフェニルなどの炭化水素系油;プロセスオイル;エポキシ化大豆油、エポキシステアリン酸ベンジルなどのエポキシ可塑剤、などをあげることができる。
これらポリエーテルポリオールのヒドロキシ基をエステル基、エーテル基などに変換した誘導体等のポリエーテル類;ポリスチレンやポリ−α−メチルスチレン等のポリスチレン類;ポリブタジエン、ポリブテン、ポリイソブチレン、ブタジエン−アクリロニトリル、ポリクロロプレン等があげられるが、これらに限定されるものではない。
本発明では、硬化性組成物が含有する重合体の数平均分子量を、GPCチャートのピークごとに求めることとする。開始剤を複数種用いることによって、1度の重合操作で複数種の重合体を得ることができるが、その場合は纏めて数平均分子量を計算するのではなく、重合体ごと、つまりピークごとに数平均分子量を求めることとする。
反応性ケイ素基を有する有機重合体(B)の反応性ケイ素基は、反応性ケイ素基含有有機重合体(A)で例示した反応性ケイ素基と同じものを使用することができる。
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)と(B)の合計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。
数平均分子量が約4,800(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)のポリプロピレングリコールの水酸基に対して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、さらに3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。次に得られたアリル基末端ポリオキシプロピレン100重量部に対して白金ジビニルジシロキサン錯体(白金換算で3重量%のイソプロパノール溶液)36ppmを加え撹拌しながら、ジメトキシメチルシラン5.99重量部をゆっくりと滴下した。その混合溶液を90℃で2時間反応させた後、未反応のジメトキシメチルシランを減圧下留去することにより、末端がジメトキシメチルシリル基であり、1分子あたりのケイ素基が平均1.5個、数平均分子量が4,800である、直鎖状の反応性ケイ素基含有ポリオキシプロピレン重合体(A−1)を得た。
数平均分子量が約4,100(合成例1と同様の方法で算出)のポリオキシプロピレントリオール100重量部に対して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、さらに3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。次に得られたアリル基末端ポリオキシプロピレン100重量部に対して白金ジビニルジシロキサン錯体(白金換算で3重量%のイソプロパノール溶液)36ppmを加え撹拌しながら、ジメトキシメチルシラン8.14重量部をゆっくりと滴下した。その混合溶液を90℃で2時間反応させた後、未反応のジメトキシメチルシランを減圧下留去することにより、末端がジメトキシメチルシリル基であり、1分子あたりのケイ素基が平均2.2個、数平均分子量4,100である、分岐状の反応性ケイ素基含有ポリオキシプロピレン重合体(A−2)を得た。
数平均分子量が約4,100(合成例1と同様の方法で算出)のポリオキシプロピレントリオール100重量部に対してジブチル錫ジラウレート30ppmを加え攪拌しながら、3−イソシアネートプロピルトリメトキシシラン19.3重量部をゆっくり滴下した。その混合溶液を90℃で3時間反応させた後2時間脱気を行い、末端がトリメトキシシリル基であり、1分子あたりのケイ素基が平均2.8個、数平均分子量が4,100である、分岐状の反応性ケイ素基含有ポリオキシプロピレン重合体(A−3)を得た。
数平均分子量が約4,100(合成例1と同様の方法で算出)のポリプロピレングリコールの水酸基に対して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、さらに3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。次に得られたアリル基末端ポリオキシプロピレン100重量部に対して白金ジビニルジシロキサン錯体(白金換算で3重量%のイソプロパノール溶液)36ppmを加え撹拌しながら、ジメトキシメチルシラン3.80重量部をゆっくりと滴下した。その混合溶液を90℃で2時間反応させた後、未反応のジメトキシメチルシランを減圧下留去することにより、末端がジメトキシメチルシリル基であり、1分子あたりのケイ素基が平均1.0個、数平均分子量が4,100である、直鎖状の反応性ケイ素基含有ポリオキシプロピレン重合体(B−1)を得た。
数平均分子量が約3,000のポリオキシプロピレンジ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、数平均分子量が14,600(合成例1と同様の方法で算出)のポリオキシプロピレングリコールを得た。続いてこの水酸基末端ポリオキシプロピレンジオールの水酸基に対して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、さらに3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。次に得られたアリル基末端ポリオキシプロピレン100重量部に対して白金ジビニルジシロキサン錯体(白金換算で3重量%のイソプロパノール溶液)36ppmを加え撹拌しながら、ジメトキシメチルシラン1.77重量部をゆっくりと滴下した。その混合溶液を90℃で2時間反応させた後、未反応のジメトキシメチルシランを減圧下留去することにより、末端がジメトキシメチルシリル基であり、1分子あたりのケイ素基が平均1.5個、数平均分子量14,600である、直鎖状の反応性ケイ素基含有ポリオキシプロピレン重合体(B−2)を得た。
数平均分子量が約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サイドの重合を行い、数平均分子量26,200(合成例1と同様の方法で算出)のポリオキシプロピレントリオールを得た。続いてこの水酸基末端ポリオキシプロピレントリオールの水酸基に対して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、さらに3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。次に得られたアリル基末端ポリオキシプロピレン100重量部に対して白金ジビニルジシロキサン錯体(白金換算で3重量%のイソプロパノール溶液)36ppmを加え、撹拌しながら、ジメトキシメチルシラン1.28重量部をゆっくりと滴下した。その混合溶液を90℃で2時間反応させた後、未反応のジメトキシメチルシランを減圧下留去する事により、末端がジメトキシメチルシシリル基であり1分子あたりのケイ素基が平均2.2個、数平均分子量が26,200である反応性ケイ素基含有ポリオキシプロピレン重合体(B−3)を得た。
数平均分子量が約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サイドの重合を行い、数平均分子量16,400(合成例1と同様の方法で算出)のポリオキシプロピレントリオールを得た。続いてこの水酸基末端ポリオキシプロピレントリオールの水酸基に対して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、さらに3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。次に得られたアリル基末端ポリオキシプロピレン100重量部に対して白金ジビニルジシロキサン錯体(白金換算で3重量%のイソプロパノール溶液)36ppmを加え、撹拌しながら、ジメトキシメチルシラン1.78重量部をゆっくりと滴下した。その混合溶液を90℃で2時間反応させた後、未反応のジメトキシメチルシランを減圧下留去する事により、末端がジメトキシメチルシシリル基であり1分子あたりのケイ素基が平均2.2個、数平均分子量が16,400である反応性ケイ素基含有ポリオキシプロピレン重合体(B−4)を得た。
重合体(A−1)100重量部に対して、脂肪酸処理炭酸カルシウム(白石工業(株)製、商品名:白艶華CCR)120重量部、顔料(石原産業(株)製、商品名:タイペークR820)20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重量部を混合して充分混練りした後、3本ペイントロールに1回通して分散させ、配合物を作製した。
作製した配合物の粘比、硬度およびガラス板割れ強度を下記に示す方法にて測定した。
(粘比)
23℃、相対湿度50%の雰囲気下にて、BS型粘度計、ローターNo.7(東機産業社製)を用い、回転数が2rpm、10rpmの時の粘度を測定し、チクソトロピー性の指標として、回転数が2rpmと10rpmの時の粘比を測定した。その結果を表1、及び、表2に示した。
(硬度)
23℃、相対湿度50%の雰囲気下にて、配合物に重合体(A−1)100重量部に対して、ビニルトリメトキシシラン(Momentive(株)製、商品名:A−171)2重量部、N−(2−アミノエチル)−3− アミノプロピルトリメトキシシラン(Momentive(株)製、商品名:A−1122)3重量部、縮合触媒としてジブチルスズビス(アセチルアセトネート)(日東化成(株))2重量部を加え十分混合した。混合物を厚さ約8mm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、3日後に硬化物をJIS K 6253に準拠して、タイプAデュロメーターを用いて、硬度を測定した。その結果を表1、及び、表2に示した。
(ガラス板の割れ強度試験)
23℃、相対湿度50%の雰囲気下にて、配合物に重合体(A−1)100重量部に対して、ビニルトリメトキシシラン(Momentive(株)製、商品名:A−171)2重量部、N−(2−アミノエチル)−3− アミノプロピルトリメトキシシラン(Momentive(株)製、商品名:A−1122)3重量部、縮合触媒としてジブチルスズビス(アセチルアセトネート)(日東化成(株))2重量部を加え十分混合した。
70mm×150mm×4mmのスレート板上に上記で作製した配合物をくし目ごてを用いてくし目状に塗布し、70mm×150mm×1.8mmのガラス板(TP技研(株)製、フロート板ガラス)を張り合わせた(以後、試験体と呼ぶ)。23℃、相対湿度50%で3日間、さらに50℃で4日間養生することにより配合物を硬化させた。試験体をJIS K 7171に記載の曲げ試験機(支点間距離10mm、圧子半径5mm)を用いて、曲げ試験を行い、ガラス板が割れるのに要する力を測定した。その結果を表1、及び、表2に示した。
表1及び表2に示す割合で配合物を用いた以外は、実施例1と同様にして配合物を作製し、評価を行った。
重合体(A−1)50重量部、重合体(B−4)50重量部の合計100重量部に対して、フタル酸イソデシル(ジェイ・プラス(株)製、商品名:DIDP)20重量部、脂肪酸処理沈降炭酸カルシウム(白石工業(株)製、商品名:白艶華CCR)50重量部、重質炭酸カルシウム(白石カルシウム(株)製、商品名:ホワイトンSB赤)200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重量部を混合して充分混練りした後、3本ペイントロールに1回通して分散させ、配合物を作製した。
作製した配合物の粘比、硬度及び引張り物性を下記に示す方法にて作製した。
(粘比)
23℃、相対湿度50%の雰囲気下にて、BS型粘度計、ローターNo.7(東機産業社製)を用い、回転数が2rpm、10rpmの時の粘度を測定し、チクソトロピー性の指標として、回転数が2rpmと10rpmの時の粘比を測定した。その結果を表3に示した。
(硬度)
23℃、相対湿度50%の雰囲気下にて、配合物に重合体(A−1)及び、重合体(B−4)の合計100重量部に対して、ビニルトリメトキシシラン(Momentive(株)製、商品名:A−171)2重量部、N−(2−アミノエチル)−3− アミノプロピルトリメトキシシラン(Momentive(株)製、商品名:A−1122)3重量部、縮合触媒としてジブチルスズビス(アセチルアセトネート)(日東化成(株))2重量部を加え十分混合した。混合物を厚さ約8mm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、3日後に硬化物をJIS K 6253に準拠して、タイプAデュロメーターを用いて、硬度を測定した。その結果を表3に示した。
(引張り物性)
23℃、相対湿度50%の雰囲気下にて、配合物に重合体(A−1)及び、重合体(B−4)の合計100重量部に対して、ビニルトリメトキシシラン(Momentive(株)製、商品名:A−171)2重量部、N−(2−アミノエチル)−3− アミノプロピルトリメトキシシラン(Momentive(株)製、商品名:A−1122)3重量部、縮合触媒としてジブチルスズビス(アセチルアセトネート)(日東化成(株))2重量部を加え十分混合した。混合物を厚み3mmのポリエチレン製の型枠に気泡が入らないよう充填し、23℃、相対湿度50%で3日間、さらに50℃で4日間養生することにより硬化物を得た。得られた硬化物から、JIS K 6251に準拠して3号ダンベルを打ち抜き、引張り試験(引張り速度200mm/分、23℃、相対湿度50%)を行い、破断時伸びを測定した。その結果を表3に示した。
表3に示す割合で配合物を用いた以外は、実施例6と同様にして配合物を作製し、評価を行った。
Claims (13)
- (A)数平均分子量が2,000〜6,000であり、1分子中に反応性ケイ素基を1.3〜5個含有する反応性ケイ素基含有有機重合体100重量部、及び、(C)可塑剤0〜40重量部を含有する硬化性組成物。
- (A)成分である反応性ケイ素基含有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)成分である反応性ケイ素基含有有機重合体の主鎖構造が、少なくとも1つ以上の分岐鎖を有してい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。
- (A)成分である反応性ケイ素基含有有機重合体が、1分子中に反応性ケイ素基を2〜5個含有することを特徴とする請求項1〜3のいずれか1項に記載の硬化性組成物。
- (C)成分である可塑剤を含有しないことを特徴とする請求項1〜4のいずれか1項に記載の硬化性組成物。
- 組成物中に、数平均分子量が8,000〜50,000であり1分子中に反応性ケイ素基を1.3〜5個含有する反応性ケイ素基含有有機重合体(B)が含有されていることを特徴とする請求項1〜5のいずれか1項に記載の硬化性組成物。
- (B)成分である反応性ケイ素基含有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。
- 請求項1〜7のいずれか1項に記載の硬化性組成物を成分として含む接着剤。
- 請求項1〜7のいずれか1項に記載の硬化性組成物を成分として含む床用接着剤。
- 請求項1〜5のいずれか1項に記載の硬化性組成物を成分として含むタイル張り用接着剤。
- 請求項6〜7のいずれか1項に記載の硬化性組成物を成分として含むタイル張り用接着剤。
- 請求項1〜7のいずれか1項に記載の硬化性組成物を硬化させて得られるコーティング剤。
- 請求項1〜7のいずれか1項に記載の硬化性組成物を硬化させて得られる硬化物。
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JP6218661B2 (ja) * | 2013-10-31 | 2017-10-25 | 積水フーラー株式会社 | 硬化性組成物 |
CN106062082B (zh) | 2014-03-05 | 2019-03-12 | 株式会社钟化 | 固化性组合物 |
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