JP2017066349A - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
- Publication number
- JP2017066349A JP2017066349A JP2015196967A JP2015196967A JP2017066349A JP 2017066349 A JP2017066349 A JP 2017066349A JP 2015196967 A JP2015196967 A JP 2015196967A JP 2015196967 A JP2015196967 A JP 2015196967A JP 2017066349 A JP2017066349 A JP 2017066349A
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- reactive silicon
- meth
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- 239000000203 mixture Substances 0.000 title claims abstract description 114
- 229920000642 polymer Polymers 0.000 claims abstract description 196
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 116
- 239000000178 monomer Substances 0.000 claims abstract description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 40
- 230000001070 adhesive effect Effects 0.000 claims abstract description 35
- 239000000853 adhesive Substances 0.000 claims abstract description 34
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000003566 sealing material Substances 0.000 claims abstract description 25
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000000470 constituent Substances 0.000 claims description 3
- -1 acryl Chemical group 0.000 description 171
- 238000000034 method Methods 0.000 description 95
- 150000001875 compounds Chemical class 0.000 description 78
- 239000000047 product Substances 0.000 description 66
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
- 229920000647 polyepoxide Polymers 0.000 description 37
- 239000003822 epoxy resin Substances 0.000 description 36
- 238000006116 polymerization reaction Methods 0.000 description 36
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000004014 plasticizer Substances 0.000 description 31
- 239000000463 material Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 26
- 239000000126 substance Substances 0.000 description 26
- 229920005989 resin Polymers 0.000 description 25
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- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 229920001451 polypropylene glycol Polymers 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 20
- 238000010526 radical polymerization reaction Methods 0.000 description 17
- 150000004756 silanes Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 239000002243 precursor Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 14
- 229910000019 calcium carbonate Inorganic materials 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 230000000704 physical effect Effects 0.000 description 14
- 239000006087 Silane Coupling Agent Substances 0.000 description 13
- 230000018044 dehydration Effects 0.000 description 13
- 238000006297 dehydration reaction Methods 0.000 description 13
- 239000000945 filler Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 description 12
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 125000003700 epoxy group Chemical group 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
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- 239000003999 initiator Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 8
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- 238000004519 manufacturing process Methods 0.000 description 8
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- 229920002554 vinyl polymer Polymers 0.000 description 8
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
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- 239000002245 particle Substances 0.000 description 7
- 239000005011 phenolic resin Substances 0.000 description 7
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- 229920001296 polysiloxane Polymers 0.000 description 7
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- 238000003860 storage Methods 0.000 description 7
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
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- 229920001577 copolymer Polymers 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000011572 manganese Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000000565 sealant Substances 0.000 description 6
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- 125000005372 silanol group Chemical group 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 5
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
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- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 229910020175 SiOH Inorganic materials 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
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- 238000010276 construction Methods 0.000 description 5
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
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- HMQXXOGOXHNAFR-UHFFFAOYSA-N trimethoxy(phenoxymethyl)silane Chemical compound CO[Si](OC)(OC)COC1=CC=CC=C1 HMQXXOGOXHNAFR-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 description 1
- JPPHEZSCZWYTOP-UHFFFAOYSA-N trimethoxysilylmethyl prop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C=C JPPHEZSCZWYTOP-UHFFFAOYSA-N 0.000 description 1
- OJAJJFGMKAZGRZ-UHFFFAOYSA-N trimethyl(phenoxy)silane Chemical compound C[Si](C)(C)OC1=CC=CC=C1 OJAJJFGMKAZGRZ-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- YZYKZHPNRDIPFA-UHFFFAOYSA-N tris(trimethylsilyl) borate Chemical compound C[Si](C)(C)OB(O[Si](C)(C)C)O[Si](C)(C)C YZYKZHPNRDIPFA-UHFFFAOYSA-N 0.000 description 1
- 235000021081 unsaturated fats Nutrition 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
- 239000012855 volatile organic compound Substances 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
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
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- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
反応性ケイ素基含有有機重合体を含む硬化性組成物は、充填剤や可塑剤など種々の成分を配合することで作業性や各種物性を調整できる。耐候性や接着性を付与するには、反応性ケイ素基含有ポリオキシアルキレン重合体と反応性ケイ素基含有(メタ)アクリル酸エステル系重合体とを組合せて用いることが有用である(特許文献2)。これらは高耐候性シーラントや工業用接着剤として利用されている。
特許文献3には、反応性ケイ素基含有ポリオキシアルキレンと反応性ケイ素基を有する(メタ)アクリル酸エステル系重合体の組合せによって、高強度の硬化物が得られることが開示されている。
(1).一般式(1):−SiR1 aX3−a (1)
(式中、R1は、炭素数1〜20の置換あるいは非置換の炭化水素基を表す。Xはそれぞれ独立に水酸基または加水分解性基を表す。aは0または1を示す。)
で表される反応性ケイ素基を有し重合性不飽和基を有する単量体、及び一般式(1)で表される反応性ケイ素基と重合性不飽和基を有する数平均分子量1,000〜30,000のオキシアルキレン系マクロモノマー(a)を構成単量体とする(メタ)アクリル酸エステル系重合体(A)を含有する硬化性組成物、
(2).組成物中に、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(B)を含有する(1)に記載の硬化性組成物、
(3).(1)または(2)に記載の硬化性組成物を含有するシーリング材組成物、
(4).(1)または(2)に記載の硬化性組成物を含有する接着剤組成物、
(5).(1)または(2)に記載の硬化性組成物の硬化物、
に関する。
(メタ)アクリル酸エステル系重合体(A)は、以下の一般式(1)で表される反応性ケイ素基と重合性不飽和基を有する単量体、及び一般式(1)で表される反応性ケイ素基と重合性不飽和基を有する数平均分子量1,000〜30,000のオキシアルキレン系マクロモノマー(a)を構成単量体とする重合体である。
−SiR1 aX3−a (1)
(式中、R1は、炭素数1〜20の置換あるいは非置換の炭化水素基を表す。Xはそれぞれ独立に水酸基または加水分解性基を表す。aは0または1を示す。)
本発明において「(メタ)アクリル」とは「アクリルおよび/またはメタクリル」を表わす。
重合体(A)を構成する全単量体中の反応性ケイ素基と重合性不飽和基を有する単量体の含有量は、0.1〜90重量%が好ましく、0.5〜50重量%がより好ましく、1〜30重量%がさらにより好ましい。
重合体(A)を構成するマクロモノマー(a)は、反応性ケイ素基と重合性不飽和基を有する数平均分子量1,000〜30,000のポリオキシアルキレンである。
(i)原料となるポリオキシアルキレン(以下、「前駆重合体」ともいう)と、水酸基と反応しうる官能基(例えば、イソシアネートなど)と重合性不飽和基とを有する化合物(例えば、メタクリロイルオキシエチルイソシアネートやアクリロイルオキシエチルイソシアネートなど)を反応させる方法。
(ii)前駆重合体の水酸基をアルコキシド化した後にカルボン酸塩化物(例えば、塩化メタクリロイルや塩化アクリロイルなど)を反応させる方法。
反応性ケイ素基を導入する方法は特に限定されず、公知の方法を利用することができる。例えば、不飽和結合にヒドロシラン化合物をヒドロシリル化反応により付加させる方法が挙げられる。
ヒドロシラン化合物としては、例えば、トリクロロシラン、ジクロロメチルシラン、ジクロロフェニルシラン、(メトキシメチル)ジクロロシラン等のハロゲン化シラン類;ジメトキシメチルシラン、ジエトキシメチルシラン、トリメトキシシラン、トリエトキシシラン、(クロロメチル)ジメトキシシラン、(メトキシメチル)ジメトキシシラン等のアルコキシシラン類;トリイソプロペニロキシシラン、(クロロメチル)ジイソプロペニロキシシラン、(メトキシメチル)ジイソプロペニロキシシラン等のイソプロペニロキシシラン類等が挙げられる。
重合体(A)を構成する全単量体中のマクロモノマー(a)の含有量は、1〜90重量%が好ましく、5〜70重量%がより好ましく、10〜50重量%がさらにより好ましい。
上記(メタ)アクリル酸エステル系モノマーの重合体(A)を構成する全単量体中の含有量は、10〜99重量%が好ましく、30〜95重量%がより好ましく、50〜90重量%がさらにより好ましい。
上記単量体と共重合性を示す他の単量体を用いてもよい。他の単量体としては、例えば、スチレン、ビニルトルエン、α−メチルスチレン、クロロスチレン、スチレンスルホン酸等のスチレン系単量体;パーフルオロエチレン、パーフルオロプロピレン、フッ化ビニリデン等のフッ素含有ビニル単量体;マレイン酸、無水マレイン酸、マレイン酸モノアルキルエステル、マレイン酸ジアルキルエステル等のマレイン酸およびその誘導体;フマル酸、フマル酸モノアルキルエステル、フマル酸ジアルキルエステル等のフマル酸およびその誘導体;マレイミド、メチルマレイミド、エチルマレイミド、プロピルマレイミド、ブチルマレイミド、ヘキシルマレイミド、オクチルマレイミド、ドデシルマレイミド、ステアリルマレイミド、フェニルマレイミド、シクロヘキシルマレイミド等のマレイミド系単量体;酢酸ビニル、プロピオン酸ビニル、ピバリン酸ビニル、安息香酸ビニル、桂皮酸ビニル等のビニルエステル系単量体;エチレン、プロピレン等のオレフィン系単量体;ブタジエン、イソプレン等の共役ジエン系単量体;(メタ)アクリルアミド;(メタ)アクリロニトリル;塩化ビニル、塩化ビニリデン、塩化アリル、アリルアルコール、エチルビニルエーテル、ブチルビニルエーテル等のビニル系単量体が挙げられる。他の単量体は1種のみを使用してもよく、2種以上を併用してもよい。
上記の他の単量体の重合体(A)を構成する全単量体中の含有量は、1〜80重量%が好ましく、5〜60重量%がより好ましく、5〜40重量%がさらにより好ましい。
「リビングラジカル重合法」は、例えば、ジャーナル・オブ・アメリカン・ケミカル・ソサエティー(J.Am.Chem.Soc.)、1994年、116巻、7943頁に示されているようなコバルトポルフィリン錯体を用いるもの、特表2003−500378号公報に示されているようなニトロオキサイドラジカルを用いるもの、特開平11−130931号公報に示されているような有機ハロゲン化物やハロゲン化スルホニル化合物等を開始剤とし、遷移金属錯体を触媒とする原子移動ラジカル重合(Atom Transfer Radical Polymerization:ATRP法)等が挙げられる。また、本発明では、マクロモレキュールズ(Macromolecules)、1999年、32巻、2872頁に示されているような、いわゆる、リバース原子移動ラジカル重合、すなわち、通常の原子移動ラジカル重合触媒がラジカルを発生させた時の高酸化状態(例えば、Cu(I)を触媒として用いた時のCu(II)に対し、過酸化物等の一般的なラジカル開始剤を作用させ、その結果として原子移動ラジカル重合と同様の平衡状態)を生み出す重合法も原子移動ラジカル重合法に含まれる。
(I)重合性不飽和結合と反応性ケイ素基を有する化合物を、(メタ)アクリル酸エステルとともに共重合する方法。
(II)連鎖移動剤として、上述の反応性ケイ素基とメルカプト基を有する化合物の存在下、(メタ)アクリル酸エステルを共重合する方法。
(III)重合性不飽和結合と反応性官能基(Z基)を有する化合物(例えば、アクリル酸、アクリル酸2−ヒドロキシエチル)を、Z基を有さない(メタ)アクリル酸エステルとともに共重合した後、反応性ケイ素基とZ基に反応する官能基を有する化合物(例えば、イソシアネートシラン化合物)を反応させる方法。
(IV)リビングラジカル重合法によって(メタ)アクリル酸エステルを重合した後、分子鎖末端に反応性ケイ素基を導入する方法。
分子鎖末端および側鎖の両方に反応性ケイ素基を導入することができる点から、上記(I)と(II)の方法を組合せて用いることが好ましい。また、任意の分子量を有し、分子量分布が狭く、粘度が低い重合体を得ることができる点から、上記(IV)の方法が好ましい。
重合体(A)の分子量は特に限定されない。より強度の高い硬化物を得るためには、重合体(A)の分子量は高いことが好ましい。数平均分子量は、GPCによるポリスチレン換算で、好ましくは2,000以上、より好ましくは3,000以上、さらに好ましくは4,000以上であり、好ましくは100,000以下、より好ましくは50,000以下、さらに好ましくは30,000以下である。
本発明の硬化性組成物には、オキシアルキレン重合体(B)を含有していてもよい。
−SiR1 aX3−a (2)
(式中、R1、Xは一般式(1)と同じ。aは、0または1を示す。)
で表される反応性ケイ素基を有する。
原料となるポリオキシアルキレン(以下、「前駆重合体」ともいう)に不飽和結合を導入し、この不飽和結合にヒドロシラン化合物をヒドロシリル化反応により付加させる方法が挙げられる。不飽和結合の導入方法には特に限定は無く、例えば、水酸基等の官能基を有する前駆重合体に、この官能基と反応して結合を形成する基および不飽和結合を有する化合物を反応させ、不飽和結合を含有する重合体を得る方法;不飽和結合を有する単量体を重合させる方法;等が挙げられる。
水酸基、アミノ基、不飽和結合等の官能基を有する前駆重合体と、その官能基と反応して結合を形成する基(以下、「反応性基」ともいう)および反応性ケイ素基の両方を有する化合物(シランカップリング剤)とを反応させる方法が挙げられる。前駆重合体の官能基とシランカップリング剤の反応性基の組合せとしては、水酸基とイソシアネート基、水酸基とエポキシ基、アミノ基とイソシアネート基、アミノ基とチオイソシアネート基、アミノ基とエポキシ基、アミノ基とα,β−不飽和カルボニル基(マイケル付加による反応)、カルボキシ基とエポキシ基、不飽和結合とメルカプト基等が挙げられるがこれに限らない。
−NR2−C(=O)− (3)
(式中、R2は炭素数1〜10の有機基または水素原子を表す)で表されるアミドセグメントを含んでいてもよい。
Z−R3−SiR1 aX3−a (4)
(式中、R1、Xおよびaは、前記と同じである。R3は、2価の有機基、好ましくは炭素数1〜20の2価の炭化水素基である。Zは、水酸基、カルボキシ基、メルカプト基、1級アミノ基または2級アミノ基である。)
で表されるケイ素化合物のZ基を、合成した重合体のイソシアネート基の全部または一部に反応させる方法を挙げることができる。
O=C=N−R3−SiR1 aX3−a (5)
(式中、R3、R1、Xおよびaは、前記と同じである。)
で示される反応性ケイ素基含有イソシアネート化合物を反応させる方法を挙げることができる。
(a)末端に水酸基を有するポリオキシアルキレン(前駆重合体)と不飽和結合を有するエポキシ化合物とを反応させて、前駆重合体の末端に不飽和結合および水酸基を導入し、
(b)水酸基と反応して結合を形成する基(例えばハロゲン原子)および不飽和結合を有する化合物と得られた重合体とを反応させて、重合体の末端に複数の不飽和結合を導入し、
(c)複数の不飽和結合にヒドロシラン化合物をヒドロシリル化反応により付加させる
方法が挙げられる。
上記反応(b)により得られる重合体の末端は、一般式(6):
で表される。
本発明の効果を阻害しない限り、本発明の硬化性組成物は上述の重合体(A)および重合体(B)以外の成分(その他の成分)を含有していてもよい。以下、その他の成分について説明する。
シランカップリング剤の具体例としては、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、α−イソシアネートメチルトリメトキシシラン、α−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−アミノプロピルトリメトキシシラン、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルメチルジメトキシシラン、γ−アミノプロピルメチルジエトキシシラン、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、N−β−アミノエチル−γ−アミノプロピルメチルジメトキシシラン、N−β−アミノエチル−γ−アミノプロピルトリエトキシシラン、N−β−アミノエチル−γ−アミノプロピルメチルジエトキシシラン、γ−ウレイドプロピルトリメトキシシラン、N−フェニル−γ−アミノプロピルトリメトキシシラン、N−ベンジル−γ−アミノプロピルトリメトキシシラン、N−ビニルベンジル−γ−アミノプロピルトリエトキシシラン、(アミノメチル)ジメトキシメチルシラン、(アミノメチル)トリメトキシシラン、(フェニルアミノメチル)ジメトキシメチルシラン、(フェニルアミノメチル)トリメトキシシラン、ビス(3−トリメトキシシリルプロピル)アミン等のアミノ基含有シラン類;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等のメルカプト基含有シラン類;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;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(β−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;メチル(N−ジメトキシメチルシリルメチル)カルバメート、メチル(N−トリメトキシシリルメチル)カルバメート、メチル(N−ジメトキシメチルシリルプロピル)カルバメート、メチル(N−トリメトキシシリルプロピル)カルバメート等のカルバメートシラン類;(メトキシメチル)ジメトキシメチルシラン、(メトキシメチル)トリメトキシシラン、(エトキシメチル)トリメトキシシラン、(フェノキシメチル)トリメトキシシラン等のアルコキシ基含有シラン類;3−(トリメトキシシリル)プロピル無水コハク酸、3−(トリエトキシシリル)プロピル無水コハク酸等の酸無水物含有シラン類等を挙げることができる。また、これらの部分縮合物や、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。これらのシランカップリング剤は単独で用いても良いし、組合わせて用いても良い。シランカップリング剤の反応物としては、イソシアネートシランと水酸基含有化合物、アミノ基含有化合物との反応物;アミノシランのマイケル付加反応物;アミノシランとエポキシ基含有化合物との反応物、エポキシシランとカルボン酸基含有化合物、アミノ基含有化合物との反応物なども挙げられる。
なお、一般的に炭酸カルシウムは、比表面積の値が大きいほど硬化物の破断強度、破断伸び、接着性の改善効果は大きくなる。重質炭酸カルシウムの平均一次粒子径は3μmより小さいことが好ましく、2μmより小さいことがより好ましく、1μmより小さいことが最も好ましい。平均一次粒子径の下限は0.05μmであることが好ましい。炭酸カルシウムを使用する場合、表面処理炭酸カルシウムと表面処理されていない炭酸カルシウムをそれぞれ単独で使用してもよく、併用しても良い。炭酸カルシウムの分散性を上げたい場合には表面処理していることが好ましく、強度の高い硬化物を得たい場合には表面処理されていない、または、表面処理率が低いことが好ましい。表面処理した炭酸カルシウム粉を製造するための表面処理剤としては、パルミチン酸、カプリル酸、カプリン酸、ラウリン酸、ステアリン酸、アラキジン酸、ベヘン酸、リグノセリン酸、オレイン酸、リノール酸、リノレン酸等に代表される脂肪酸や不飽和脂肪酸、及び、ロジン酸系化合物等のカルボン酸及びそのエステル、ヘキサメチルジシラザン、クロロシラン、アミノシラン等のシラン化合物、パラフィン系化合物などが挙げられるが、これらに限定されるわけではない。なかでも、表面処理剤がカルボン酸であると、硬化性シリコーン系樹脂組成物とした場合に、一層硬化遅延が生じにくくなることから好ましい。さらに、カルボン酸のなかでも飽和脂肪酸又は不飽和脂肪酸が、より一層硬化遅延が生じにくくなることから、特に好ましい。もちろんこれら充填剤は1種類のみで使用してもよいし、2種類以上混合使用してもよい。接着強度の高い硬化物を得たい場合には重質炭酸カルシウムと膠質炭酸カルシウムを併用することが好ましい。
具体例としては、テルペン系樹脂、芳香族変性テルペン樹脂およびこれを水素添加した水素添加テルペン樹脂、テルペン類をフェノール類と共重合させたテルペン−フェノール樹脂、フェノール樹脂、変性フェノール樹脂、キシレン−フェノール樹脂、シクロペンタジエン−フェノール樹脂、クマロンインデン樹脂、ロジン系樹脂、ロジンエステル樹脂、水添ロジンエステル樹脂、キシレン樹脂、低分子量ポリスチレン系樹脂、スチレン共重合体樹脂、石油樹脂(例えば、C5炭化水素樹脂、C9炭化水素樹脂、C5C9炭化水素共重合樹脂等)、水添石油樹脂、DCPD樹脂等が挙げられる。これらは単独で用いても良く、2種以上を併用しても良い。
(合成例1)
エチレングリコールモノアリルエーテルを開始剤とし、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、数平均分子量約7,000(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)のポリオキシプロピレンを得た。続いてこの水酸基末端ポリオキシプロピレンの水酸基に対して1.0モル当量のNaOMeのメタノール溶液を添加してメタノールを留去し、続いて水酸基に対して、1.0モル当量のメタクリル酸クロリドを添加して23℃で2時間反応を行い、粗精製物を得た。
上記粗精製物をヘキサンで希釈し、吸着剤(キョーワード700SEN:協和化学製)、酸化マグネシウムを添加し1時間攪拌した後に固形成分をろ過除去した。ろ液を減圧濃縮し、片末端にアリル基、片末端にメタクリロイル基を有するオキシプロピレン重合体を得た。得られた重合体100重量部に対し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)72ppm、重合禁止剤としてp−メトキシフェノール200ppmを加え、撹拌しながら、ジメトキシメチルシラン2.3重量部、をゆっくりと滴下し、90℃で2時間反応させることにより、片末端がジメトキシメチルシリル基(1分子あたりのケイ素基が平均0.86個)、もう一方の片末端がメタクリロイル基(1分子あたりのメタクリロイル基が平均0.8個)、数平均分子量が7,000である直鎖状のマクロモノマー(a−1)を得た。
攪拌機を備えた四口フラスコにイソブタノール45.9重量部を入れ、窒素雰囲気下、105℃まで昇温した。そこに、メチルメタクリレート35.0重量部、ステアリルメタクリレート25.0重量部、合成例1で合成したマクロモノマー(a−1)30重量部、3−メタクリロキシプロピルトリメトキシシラン10.0重量部、3−メルカプトプロピルトリメトキシシラン4.0重量部、及び2,2’−アゾビス(2−メチルブチロニトリル)2.5重量部をイソブタノール25.2重量部に溶解した混合溶液を5時間かけて滴下した。さらに105℃で2時間重合を行い、1分子あたりのケイ素基が平均2.3個、1分子あたりに導入されているマクロモノマーの数が平均0.2個、数平均分子量が3,600、重量平均分子量が12,800(合成例1と同様の方法で測定した)である反応性ケイ素基含有(メタ)アクリル酸エステル系重合体(A−1)のイソブタノール溶液(固形分60%)を得た。
攪拌機を備えた四口フラスコにイソブタノール59.5重量部を入れ、窒素雰囲気下、90℃まで昇温した。そこに、メチルメタクリレート14.5重量部、ブチルアクリレート45.0重量部、ステアリルメタクリレート14.3重量部、合成例1で合成したマクロモノマー(a−1)25重量部、3−メタクリロキシプロピルジメトキシメチルシラン1.2重量部、及び2,2’−アゾビス(2−メチルブチロニトリル)0.56重量部をイソブタノール7.5重量部に溶解した混合溶液を5時間かけて滴下した。さらに90℃で2時間重合を行い、1分子あたりのケイ素基が平均1.7個、1分子あたりに導入されているマクロモノマーの数が平均0.9個、数平均分子量が18,400、重量平均分子量が51,300(合成例1と同様の方法で測定した)である反応性ケイ素基含有(メタ)アクリル酸エステル系重合体(A−2)のイソブタノール溶液(固形分60%)を得た。
攪拌機を備えた四口フラスコにイソブタノール45.9重量部を入れ、窒素雰囲気下、105℃まで昇温した。そこに、メチルメタクリレート35.0重量部、ブチルアクリレート30重量部、ステアリルメタクリレート25.0重量部、3−メタクリロキシプロピルトリメトキシシラン10.0重量部、3−メルカプトプロピルトリメトキシシラン4.0重量部、及び2,2’−アゾビス(2−メチルブチロニトリル)2.5重量部をイソブタノール25.2重量部に溶解した混合溶液を5時間かけて滴下した。さらに105℃で2時間重合を行い、1分子あたりのケイ素基が平均2.1個、数平均分子量が3,600、重量平均分子量が7,400(合成例1と同様の方法で測定した)である反応性ケイ素基含有(メタ)アクリル酸エステル系重合体(P−1)のイソブタノール溶液(固形分60%)を得た。
攪拌機を備えた四口フラスコにイソブタノール59.5重量部を入れ、窒素雰囲気下、90℃まで昇温した。そこに、メチルメタクリレート14.5重量部、ブチルアクリレート68.2重量部、ステアリルメタクリレート14.9重量部、3−メタクリロキシプロピルジメトキシメチルシラン2.4重量部、及び2,2’−アゾビス(2−メチルブチロニトリル)0.56重量部をイソブタノール7.5重量部に溶解した混合溶液を5時間かけて滴下した。さらに90℃で2時間重合を行い、1分子あたりのケイ素基が平均1.7個、数平均分子量が16,900、重量平均分子量が44,100(合成例1と同様の方法で測定した)である反応性ケイ素基含有(メタ)アクリル酸エステル系重合体(P−2)のイソブタノール溶液(固形分60%)を得た。
数平均分子量が約2,000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サイドの重合を行い、数平均分子量約28,500(合成例1と同様の方法で測定した)のポリオキシプロピレンジオールを得た。続いてこの水酸基末端ポリオキシプロピレンの水酸基に対して1.0モル当量のNaOMeのメタノール溶液を添加してメタノールを留去し、続いて水酸基に対して、1.0モル当量のアリルグリシジルエーテルを添加して130℃で2時間反応を行った。その後、0.28当量のナトリウムメトキシドのメタノール溶液を添加してメタノールを除去し、さらに1.79モル当量の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。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オキシプロピレン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、1つの末端部位に炭素−炭素不飽和結合を平均2.1個有するポリオキシプロピレン重合体を得た。次に得られた重合体100重量部に対し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)72ppmを加え、撹拌しながら、トリエトキシシラン2.9重量部をゆっくりと滴下し、90℃で2時間反応させた。さらにメタノール20重量部、HCl12ppmを添加して末端のエトキシ基をメトキシ基に変換することにより、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3.2個、数平均分子量が28,500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2,000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サイドの重合を行い、数平均分子量28,500(合成例1と同様の方法で算出した)のポリオキシプロピレンジオールを得た。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1.5倍当量の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重合体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%のイソプロピルアルコール溶液)36ppmを加え撹拌しながら、ジメトキシメチルシラン0.96重量部をゆっくりと滴下し、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1.6個、数平均分子量が28,500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。
合成例6で得られた反応性ケイ素基含有ポリオキシプロピレン重合体(B−1)50.0重量部と合成例2で得られた反応性ケイ素基含有(メタ)アクリル系重合体(A−1)のイソブタノール溶液83.3重量部を混合して、イソブタノールを減圧留去し、重合体の重量比(A−1)/(B−1)=50/50である重合体混合物を得た。
作製した重合体混合物の粘度、硬化物の引張物性を下記に示す方法にて測定した。
23℃、相対湿度50%で、配合物の粘度をE型粘度計(東京計器製、測定コーン:3°C×R14)で測定した。その結果を表2に示した。
重合体(A−1)と(B−1)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)1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(信越化学工業(株)製、商品名:KBM−603)2重量部、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重量部を添加した後、十分混合した。得られた配合物を厚み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7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、100%伸張時のモジュラス(M100)、破断時強度(TB)、破断時伸び率(EB)を測定した。その結果を表2に示した。
Claims (5)
- 一般式(1):−SiR1 aX3−a (1)
(式中、R1は、炭素数1〜20の置換あるいは非置換の炭化水素基を表す。Xはそれぞれ独立に水酸基または加水分解性基を表す。aは0または1を示す。)
で表される反応性ケイ素基を有し重合性不飽和基を有する単量体、及び一般式(1)で表される反応性ケイ素基と重合性不飽和基を有する数平均分子量1,000〜30,000のオキシアルキレン系マクロモノマー(a)を構成単量体とする(メタ)アクリル酸エステル系重合体(A)を含有する硬化性組成物。 - 組成物中に、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(B)を含有する請求項1に記載の硬化性組成物。
- 請求項1または2に記載の硬化性組成物を含有するシーリング材組成物。
- 請求項1または2に記載の硬化性組成物を含有する接着剤組成物。
- 請求項1または2に記載の硬化性組成物の硬化物。
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