JP6282061B2 - 硬化性組成物およびその硬化物および薄層硬化性改善方法 - Google Patents
硬化性組成物およびその硬化物および薄層硬化性改善方法 Download PDFInfo
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- JP6282061B2 JP6282061B2 JP2013176966A JP2013176966A JP6282061B2 JP 6282061 B2 JP6282061 B2 JP 6282061B2 JP 2013176966 A JP2013176966 A JP 2013176966A JP 2013176966 A JP2013176966 A JP 2013176966A JP 6282061 B2 JP6282061 B2 JP 6282061B2
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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
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-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
- 239000002383 tung oil Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000004591 urethane sealant Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 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
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- RQIDQEBURXNDKG-MDZDMXLPSA-N ximenic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCCCCCC(O)=O RQIDQEBURXNDKG-MDZDMXLPSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
(I).シロキサン結合を形成することにより架橋し得る反応性ケイ素基を有する有機重合体(A)、マイクロバルーン(B)、カルボン酸金属塩(C)を含有する硬化性組成物であって、さらに、一分子中の炭素数の合計が12以上である第二級アミン化合物(D)とアリール基を有するグアニジン化合物(E)の少なくとも一つを含有する硬化性組成物、
(II).有機重合体(A)の主鎖が、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より選択される少なくとも1つである、(I)に記載の硬化性組成物、
(III).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、(II)に記載の硬化性組成物、
(IV).有機重合体(A)の主鎖骨格中に、ウレタン結合および/またはウレア結合を有することを特徴とする、(I)〜(III)のいずれかに記載の硬化性組成物、
(V).第二級アミン化合物(D)が、環状構造を含まない構造である、(I)〜(IV)のいずれかに記載の硬化性組成物、
(VI).第二級アミン化合物(D)の分子量が200以上である、(I)〜(V)のいずれかに記載の硬化性組成物、
(VII).第二級アミン化合物(D)が、少なくとも炭素数6以上の直鎖構造の炭化水素基を有している、(I)〜(VI)のいずれかに記載の硬化性組成物、
(VIII).有機重合体(A)100重量部に対して、第二級アミン化合物(D)が0.65〜3重量部である、(I)〜(VII)のいずれかに記載の硬化性組成物、
(IX).さらに、第一級アミン化合物(F)を含む、(I)〜(VIII)のいずれかに記載の硬化性組成物、
(X).(C)成分が、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である、(I)〜(IX)のいずれかに記載の硬化性組成物、
(XI).(C)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、(X)に記載の硬化性組成物、
(XII).マイクロバルーン(B)が、熱可塑性樹脂を用いたマイクロバルーンである、(I)〜(XI)のいずれかに記載の硬化性組成物、
(XIII).マイクロバルーン(B)の平均粒径が5〜200μmである、(I)〜(XII)のいずれかに記載の硬化性組成物、
(XIV).さらに、空気硬化性化合物(G)を含む、(I)〜(XIII)のいずれかに記載の硬化性組成物、
(XV).空気硬化性化合物(G)が、不飽和結合を有する植物油である、(XIV)に記載の硬化性組成物、
(XVI).(I)〜(XV)のいずれかに記載の硬化性組成物の硬化物、
(XVII).シロキサン結合を形成することにより架橋し得る反応性ケイ素基を有する有機重合体(A)とマイクロバルーン(B)とカルボン酸金属塩(C)を含有する組成物に、一分子中の炭素数の合計が12以上である第二級アミン化合物(D)とアリール基を有するグアニジン化合物(E)の少なくとも一つを助触媒として添加することにより、得られる硬化性組成物の薄層硬化性を改善する方法、
に関する。
−(SiR2 2−bXbO)m−SiR1 3−aXa (1)
(式中、R1および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(R’)3SiO−で示されるトリオルガノシロキシ基のいずれかを示し、R1またはR2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。ここでR’は炭素原子数1から20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時、それらは同一であってもよく、異なっていてもよい。aは0、1、2または3を、bは0、1、または2をそれぞれ示す。またm個の(SiR2 2−bXbO)基におけるbについて、それらは同一であってもよく、異なっていてもよい。mは0から19の整数を示す。但し、a+Σb≧1を満足するものとする)で表される基があげられる。
−SiR1 3−cXc (2)
(式中、R1、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。
−R3−O− (3)
(式中、R3は2価の有機基であり、炭素数1〜14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R3は、炭素数1〜14の、さらには2〜4の、直鎖状もしくは分岐状アルキレン基が好ましい。
−CH2−C(R4)(COOR5)− (4)
(式中、R4は水素原子またはメチル基、R5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(R4)(COOR6)− (5)
(式中、R4は前記に同じ、R6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。
一般式(6):
R7N=C(NR7 2)2 (6)
(5個のR7はそれぞれ独立に水素原子、ヒドロキシ基、アミノ基、ニトロ基、シアノ基、スルホン酸基、または、有機基からなる群より選択される少なくとも1つである。ただし、5個のR7のうち1個以上はアリール基である。)。
ポリ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シドの重合を行い、数平均分子量約26,000(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)の分岐構造の水酸基末端ポリオキシプロピレン重合体を得た。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1.3倍当量の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。以上により、末端がアリル基である数平均分子量約26,000のポリプロピレンオキシドを得た。
ポリプロピレンジオールとポリ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シドの重合を行い、数平均分子量約30,000(合成例1と同様にGPCで測定したポリスチレン換算分子量)の水酸基末端ポリオキシプロピレン重合体を得た。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1.3倍当量の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。以上により、末端がアリル基である数平均分子量約30,000のポリプロピレンオキシドを得た。
(A)成分として合成例1、2で得られた有機重合体(A−1)もしくは(A−2)と、(B)成分として有機系マイクロバルーン(松本油脂製薬(株)製、平均粒径10〜30μm)を必要に応じて用い、表1に示す処方にしたがって、各種添加剤をそれぞれ計量し、三本ペイントロールでよく混練して主剤とした。
(A)成分として合成例1で得られた有機重合体(A−1)と、(B)成分として有機系マイクロバルーン(松本油脂製薬(株)製、平均粒径10〜30μm)を用い、表2に示す処方にしたがって、各種添加剤をそれぞれ計量し、三本ペイントロールでよく混練して主剤とした。
Claims (16)
- シロキサン結合を形成することにより架橋し得る反応性ケイ素基を有する有機重合体(A)、マイクロバルーン(B)、カルボン酸金属塩(C)を含有する硬化性組成物であって、さらに、一分子中の炭素数の合計が12以上である第二級アミン化合物(D)を含有し、
前記第二級アミン化合物(D)が、環状構造を含まない構造であり、
ただし、Si−F結合を有するケイ素基を含有する重合体を含有しない、硬化性組成物。 - 有機重合体(A)の主鎖が、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より選択される少なくとも1つである、請求項1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2に記載の硬化性組成物。
- 有機重合体(A)の主鎖骨格中に、ウレタン結合および/またはウレア結合を有することを特徴とする、請求項1〜3のいずれかに記載の硬化性組成物。
- 第二級アミン化合物(D)の分子量が200以上である、請求項1〜4のいずれかに記載の硬化性組成物。
- 第二級アミン化合物(D)が、少なくとも炭素数6以上の直鎖構造の炭化水素基を有している、請求項1〜5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、第二級アミン化合物(D)が0.65〜3重量部である、請求項1〜6のいずれかに記載の硬化性組成物。
- さらに、第一級アミン化合物(F)を含む、請求項1〜7のいずれかに記載の硬化性組成物。
- (C)成分が、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である、請求項1〜8のいずれかに記載の硬化性組成物。
- (C)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、請求項9に記載の硬化性組成物。
- マイクロバルーン(B)が、熱可塑性樹脂を用いたマイクロバルーンである、請求項1〜10のいずれかに記載の硬化性組成物。
- マイクロバルーン(B)の平均粒径が5〜200μmである、請求項1〜11のいずれかに記載の硬化性組成物。
- さらに、空気硬化性化合物(G)を含む、請求項1〜12のいずれかに記載の硬化性組成物。
- 空気硬化性化合物(G)が、不飽和結合を有する植物油である、請求項13に記載の硬化性組成物。
- 請求項1〜14のいずれかに記載の硬化性組成物の硬化物。
- シロキサン結合を形成することにより架橋し得る反応性ケイ素基を有する有機重合体(A)とマイクロバルーン(B)とカルボン酸金属塩(C)を含有し、ただし、Si−F結合を有するケイ素基を含有する重合体を含有しない組成物に、一分子中の炭素数の合計が12以上である第二級アミン化合物(D)とアリール基を有するグアニジン化合物(E)の少なくとも一つを助触媒として添加することにより、得られる硬化性組成物の薄層硬化性を改善する方法。
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