JP6531043B2 - 熱伝導性の熱ラジカル硬化型シリコーン組成物を形成する方法 - Google Patents
熱伝導性の熱ラジカル硬化型シリコーン組成物を形成する方法 Download PDFInfo
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- JP6531043B2 JP6531043B2 JP2015557163A JP2015557163A JP6531043B2 JP 6531043 B2 JP6531043 B2 JP 6531043B2 JP 2015557163 A JP2015557163 A JP 2015557163A JP 2015557163 A JP2015557163 A JP 2015557163A JP 6531043 B2 JP6531043 B2 JP 6531043B2
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- 125000001931 aliphatic group Chemical group 0.000 claims description 51
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- 239000004322 Butylated hydroxytoluene Substances 0.000 description 14
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- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052718 tin Inorganic materials 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
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-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
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
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Description
(A)
a)1分子当たり平均して少なくとも2つの脂肪族不飽和有機基を有するポリオルガノシロキサン、
b)1分子当たり平均して4〜15個のケイ素原子、及び成分a)中の脂肪族不飽和有機基当たり少なくとも4個のケイ素結合水素原子を有する、ポリオルガノ水素シロキサン、及び
c)1分子当たり、少なくとも1つの脂肪族不飽和有機基、及びアクリレート基及びメタクリレート基から選択される1つ以上の硬化性基を有する反応性分子種の、
d)ヒドロシリル化触媒及びe)異性体還元剤の存在下での反応による反応生成物を含む、クラスタ化官能性ポリオルガノシロキサンを準備することと、
(B)熱伝導性充填剤を含む充填剤(III)、充填剤処理剤(III’)、及び少なくとも1種のシリコーン用反応性希釈剤(II)及びクラスタ化官能性ポリオルガノシロキサン(I)を混合することにより混合物を形成することと、
(C)混合物を50℃〜110℃の温度に加熱して、少なくとも1種のシリコーン用反応性希釈剤(II)及びクラスタ化官能性ポリオルガノシロキサン(I)の存在下で、熱伝導性充填剤をその場(in situ)で充填剤処理剤(III’)により処理することと、
(D)工程(B)の混合物がシリコーン用反応性希釈剤(II)及びクラスタ化官能性ポリオルガノシロキサン(I)の両方を含有しないとき、混合物がシリコーン用反応性希釈剤(II)とクラスタ化官能性ポリオルガノシロキサン(I)の両方を含有するよう、シリコーン用反応性希釈剤(II)又はクラスタ化官能性ポリオルガノシロキサン(I)のいずれかを混合物に導入することと、次に、
(E)混合物を30℃以下に冷却して、ラジカル開始剤(IV)を混合物に配合することと、を含む。
(A)
a)1分子当たり平均して少なくとも2つの脂肪族不飽和有機基を有するポリオルガノシロキサン、
b)1分子当たり平均して4〜15個のケイ素原子、及び成分a)中の脂肪族不飽和有機基当たり少なくとも4個のケイ素結合水素原子を有する、ポリオルガノ水素シロキサン、及び
c)1分子当たり、少なくとも1つの脂肪族不飽和有機基、及びアクリレート基及びメタクリレート基から選択される1つ以上の硬化性基を有する反応性分子種の、
d)ヒドロシリル化触媒及びe)異性体還元剤の存在下での反応による反応生成物を含む、クラスタ化官能性ポリオルガノシロキサン(I)を準備することと、
(B)熱伝導性充填剤を含む充填剤(III)、充填剤処理剤(III’)、及びクラスタ化官能性ポリオルガノシロキサン(I)を混合することにより混合物を形成することと、
(C)混合物を50℃〜110℃の温度に加熱して、クラスタ化官能性ポリオルガノシロキサン(I)の存在下で、熱伝導性充填剤をその場(in situ)で充填剤処理剤(III’)により処理することと、次に、
(D)混合物を30℃以下に冷却して、ラジカル開始剤(IV)を混合物に配合することと、を含む方法により形成される。
a)1分子当たり平均して少なくとも2つの脂肪族不飽和有機基を有するポリオルガノシロキサン、
b)1分子当たり平均して4〜15個のケイ素原子を有するポリオルガノ水素シロキサン、及び
c)1分子当たり、少なくとも1つの脂肪族不飽和有機基、及び1つ以上のラジカル硬化性基を有する反応性種、を含む成分
を、d)ヒドロシリル化触媒及びe)異性体還元剤の存在下で反応させることによる反応生成物、並びに
所望により追加の成分を含む。
1)
a)1分子当たり平均して少なくとも2つの脂肪族不飽和有機基を有するポリオルガノシロキサン、
b)1分子当たり、平均して4〜15個のSi原子、及び成分a)中の脂肪族不飽和有機基当たり少なくとも4個のケイ素結合水素原子を有する、ポリオルガノ水素シロキサン、及び
c)1分子当たり、少なくとも1つの脂肪族不飽和有機基、及びアクリレート基及びメタクリレート基から選択される1つ以上のラジカル硬化性基を有する反応性種、を含む成分を、
d)ヒドロシリル化触媒及びe)異性体還元剤の存在下での反応による反応生成物を含む。
A)
a)1分子当たり平均して少なくとも2つの脂肪族不飽和有機基を有するポリオルガノシロキサン、
b)1分子当たり、平均して4〜15個のSi原子、及び成分a)中の脂肪族不飽和有機基当たり少なくとも4個のケイ素結合水素原子を有する、ポリオルガノ水素シロキサン、を、
d)ヒドロシリル化触媒の存在下で同時に反応させること、及びその後、
B)工程A)の生成物を、
c)1分子当たり、少なくとも1つの脂肪族不飽和有機基、及びアクリレート基及びメタクリレート基から選択される1つ以上のラジカル硬化性基を有する反応性種と、
e)異性体還元剤の存在下で反応させること、を含ませてよい
[但し、工程A)及び/又は工程B)における成分は、f)充填材、g)非反応性シリコーン樹脂、又はこれらの組み合わせを更に含み、但し、工程A)及び工程B)間に中間体精製工程は実施されず、但し、SiHb/Via比は4/1〜20/1の範囲であり、かつこのプロセスにより調製される生成物は、成分a)のポリオルガノシロキサンの各分子末端に、平均して1つ以上の硬化性基を有する]。
式中、添字qは最大で1,500の値である。その他の充填材処理剤としては、モノ末端封鎖アルコキシ官能性ポリジオルガノシロキサン、すなわち、一端にアルコキシ基を有するポリジオルガノシロキサンが挙げられる。このような充填材処理剤の例は式R25R26 2SiO(R26 2SiO)uSi(OR27)3であり、式中、添字uは値0〜100、あるいは1〜50、あるいは1〜10、及びあるいは3〜6を有する。各R25は、独立して、メチル、エチル、プロピル、ブチル、ヘキシル、及びオクチルなどのアルキル基、並びにビニル、アリル、ブテニル、及びヘキセニルなどのアルケニル基から選択される。各R26は、独立して、メチル、エチル、プロピル、ブチル、ヘキシル及びオクチルといったアルキル基である。各R27は、独立して、メチル、エチル、プロピル及びブチルといったアルキル基である。あるいは、各R25、各R26、及び各R27はメチルである。あるいは、各R25はビニルである。あるいは、各R26及び各R27はメチルである。
a)1分子当たり平均して10〜200個のケイ素原子を有するポリオルガノ水素シロキサン、及び
b)1分子当たり、少なくとも1つの脂肪族不飽和有機基及び1つ以上の硬化性基を有する反応性分子種、を、
c)異性体還元剤及びd)ヒドロシリル化触媒及びe)ヒドロシリル化触媒の阻害剤の存在下で反応させることによる、反応生成物として形成することもできる。
1)
a)1分子当たり平均して10〜200個のケイ素原子を有するポリオルガノ水素シロキサン、及び
b)1分子当たり、少なくとも1つの脂肪族不飽和有機基及び1つ以上の硬化性基を有する反応性分子種、を、
c)異性体還元剤及びd)ヒドロシリル化触媒、及び所望によりf)重合阻害剤及びg)末端保護剤の存在下で同時に反応させること、により形成される。
a)次式のシロキサン化合物
[式中、
Rは1〜6個の炭素原子を有する一価の炭化水素であり、
R’は3〜12個の炭素原子を有する二価の炭化水素であり、
R”はH又はCH3であり、かつ
添字m及びnは、それぞれ1〜10の値を有する]、及び
b)1分子当たり平均して少なくとも2つの脂肪族不飽和有機基を有するポリオルガノシロキサン、を、
c)第1のヒドロシリル化触媒及びd)第1のヒドロシリル化触媒のための阻害剤、並びに他の追加の任意成分の存在下で反応させることによる反応生成物として形成することもできる。
その他の充填材処理剤(III’)としては、アルケニル官能性ポリオルガノシロキサンが挙げられる。好適なアルケニル官能性ポリオルガノシロキサンとしては、限定するものではないが、以下のものが挙げられる:
式中、添字qは最大で1,500の値である。その他の処理剤としては、モノ末端封鎖アルコキシ官能性ポリジオルガノシロキサン、すなわち、一端にアルコキシ基を有するポリジオルガノシロキサンが挙げられる。このような処理剤の例は式R25R26 2SiO(R26 2SiO)uSi(OR27)3であり、式中、添字uは値0〜100、あるいは1〜50、あるいは1〜10、及びあるいは3〜6を有する。各R25は、独立して、Me、Et、Pr、Bu、ヘキシル、及びオクチルなどのアルキル基、及びVi、アリル、ブテニル、及びヘキセニルなどのアルケニル基から選択される。各R26は、独立して、Me、Et、Pr、Bu、ヘキシル、及びオクチルなどのアルキル基である。各R27は、独立して、Me、Et、Pr、及びBuなどのアルキル基である。あるいは、各R25、各R26、及び各R27はMeである。あるいは、各R25はビニル基(Vi)である。あるいは、各R26及び各R27はメチル(Me)である。
これらの実施例は、当業者に本発明を例示することを目的とするものであり、請求項に記載の本発明の範囲を制限するものとして解釈すべきではない。
DOW CORNING(登録商標)SFD−119;0.46重量%ビニル線状ポリジメチルシロキサン;
DOW CORNING(登録商標)SFD−117;0.2重量%ビニル線状ポリジメチルシロキサン;
DOW CORNING(登録商標)SFD−120;0.13重量%ビニル線状ポリジメチルシロキサン;
DOW CORNING(登録商標)SFD−128;0.088重量%ビニル線状ポリジメチルシロキサン;
DOW CORNING(登録商標)Q2−5057S;0.15重量% SiHメチルハイドロジェンシリコーン、線状;
DOW CORNING(登録商標)Q2−556S;0.027重量% SiHメチルハイドロジェンシリコーン、線状;
メチルハイドロジェンシロキサン;1.67重量%環状SiHメチルハイドロジェンシリコーン;
DOW CORNING(登録商標)2−0707;白金触媒0.52重量%白金;
MB2030−(DOW CORNING(登録商標)SFD−128/シリカブレンド);
メチルトリメトキシシラン(MTM);DOW CORNING(登録商標)Z6070;
OFS−1579/ETS900−メチル及びエチルトリアセトキシシランの混合物;
DOW CORNING(登録商標)Z−6030シランメタクリルオキシプロピルトリメトキシシラン;
DOW CORNING(登録商標)Z−2306シランイソブチルトリメトキシシラン(IBTMS);
DOW CORNING(登録商標)Z−6341シランn−オクチルトリエトキシシラン(nOTE);
マレイン酸ジアリル(DAM)[Bimax社(Glen Rock,Pennsylvania)から利用可能];
メタクリル酸アリル(AMA)[BASF社(Florham Park,New Jersey)から利用可能]
ブチル化ヒドロキシトルエン(BHT)[Sigma Aldrich(Milwaukee,Wisconsin)から利用可能];
酸化マグネシウム(MAGOX SUPER PREMIUM);[Premier Magnesia(W.Conshohocken,PA 19428 USAA)から利用可能];
DAW−45;酸化アルミニウム充填剤[Denkaから利用可能];
AL−43−ME;酸化アルミニウム充填剤[昭和電工から利用可能];
CB−A20S;酸化アルミニウム充填剤[昭和電工から利用可能];
Varox(登録商標)DCBP−50 Paste;[R T Vanderbilt社(Norwalk CT 06856 USAから利用可能)];
Perkadox L−50−PS;[Azko Nobel Polymer LLC(Chicago IL USA)の商品];
TAIC;トリアリルイソシアヌラート[Sigma−Aldrich社(St.Louis,MO,USA)];
TYZOR TNBT;[Dorf Ketal Speciality Catalysts(LLC,3727 Greenbriar Dr.,Stafford,TX 77477 USA)から利用可能];
TINOPAL OB,蛍光増白剤[BASF社(100 Campus Drive Florham Park,New Jersey 07932.USA)から利用可能];
DOW CORNING(登録商標)TC 1−4173は、1部白金付加硬化熱伝導性粘着剤である。
A.T(Oz)及びD(Oz)単位の生成に対する異性体還元剤の添加量の変動
乾いた三つ口フラスコに、100gのDOW CORNING(登録商標)SFD−119(ジメチルビニル末端化ジメチルシロキサン)、6.2gの環状メチル水素シロキサン、14gのアリルメタクリレート(AMA)、0.2gのブチル化ヒドロキシトルエン(BHT)及び様々な量の異性体還元剤(Dow Corning社(Midland,Michigan)から利用可能なOFS−1579、又はDBAP(2,6−ジ−tert−ブチル−4−(ジメチルアミノメチル)フェノールのいずれか)を入れ、窒素雰囲気下で混合した。0.12gの白金触媒(DOW CORNING(登録商標)2−0707)を添加し、この混合物を更に5分間混合した。次に、混合物を1時間60℃に加熱した。IR分光法を用い、2173cm−1におけるSiHピークの減少により反応をモニターした。混合物を室温に冷却し、マレイン酸ジアリル(DAM)を添加した。T(Oz)及びD(Oz)ユニットの存在について、29Si NMRにより反応混合物を分析した。以下表1及び表2に結果を要約し、配合物(OFS−1579又はDBAPのいずれか)に少なくとも100ppmの異性体還元剤を導入することで、T(Oz)及びD(Oz)単位のレベルが少なくとも10%低減すること(これは、メチル水素シロキサンのSiH基のアリルメタクリレートへのβ付加の少なくとも10%の低減に相当する)を示す。
10LのTurelloミキサーに、5000gのDOW CORNING(登録商標)SFD117、196.34gの環状メチル水素シロキサン、467.76gのAMA及び1.13gのBHTを入れ、15分間混合した。次に、5.45gの白金触媒を添加し、混合物を室温で更に15分間混合した。混合物を80℃で1時間加熱した。SIHシグナルの消失についてIRでサンプルを評価した。1時間の時点で混合物を45℃未満に冷却し、11.33gのDAMを添加した。減圧を7.3kPa(55mm Hg)に設定し、温度は80℃に上昇させ、混合物を30分間抽出した。得られた組成物(サンプル1)をパッケージング前に30℃未満に冷却した。
50LのTurelloミキサーに、6196.7gの鎖延長剤Q2−5567S、1.3gのBHT、及び318.69gのAMAを充填した。窒素雰囲気(酸素含有率2%)により混合物を不活性化させ、10分間撹拌した時点で6.64gの白金触媒を添加した。混合物を更に10分間撹拌した後、温度を50℃に設定した。DAMを9.96g添加する前に、温度を50℃で30分間維持した。混合物を更に10分間撹拌した。10キロパスカル(75トル)の減圧下で、温度を30分間50℃に維持した。得られた組成物(サンプル1)をパッケージング前に30℃未満に冷却した。
A.マスターバッチは使用せず、異性体還元剤を使用するメタクリレートクラスタ化シリコーンポリマー(MCP−2)の調製
50LのTurelloミキサーに6kgのDOW CORNING(登録商標)SFD120ポリマー、176.92gの環状メチルハイドロジェンシロキサン、及び274.74gの鎖延長剤Q2−5057Sを充填した。窒素雰囲気(2%酸素)を利用して混合物を不活性化し、10分間撹拌した。1.08gのBHT、537.58gのAMA、及び1.08gのOFS−1579異性体還元剤を含有する均質化混合物を混合物に導入した。得られた混合物を室温で更に10分間撹拌し、8.03gの白金触媒を添加した。混合物を更に10分間撹拌した後、温度を80℃に設定した。この温度(80℃)を30分間維持した後、50℃未満に冷却し、12.05gのDAMを加えた。混合物を更に10分間撹拌した後、温度を80℃に設定した。10キロパスカル(75トル)への減圧下で、温度を30分間80℃に維持した。次に混合物を35℃未満に冷却した。得られるポリマーを以下MCP−2と呼ぶ。
50LのTurelloミキサーに6196.7gの鎖延長剤Q2−5567S、1.3gのBHT、318.69gのAMA、及び1.3gのOFS−1579異性体還元剤を充填した。窒素雰囲気(酸素含有率2%)により混合物を不活性化させ、10分間撹拌した時点で6.64gの白金触媒を添加した。混合物を更に10分間撹拌した後、温度を50℃に設定した。DAMを9.96g添加する前に、温度を50℃で30分間維持した。混合物を更に10分間撹拌した。10キロパスカル(75トル)の減圧下で、温度を30分間50℃に維持した。次に混合物を35℃未満に冷却した。得られたポリマーを以下SRD−1と呼ぶ。
0.9Lの(1quart)のGallon Baker Perkinミキサーに、75.27gのMCP−2、128.53gのSRD−1、461.06gのAl−43−ME(Al2O3充填剤)、及び19.52gのDOW CORNING(登録商標)Z−6341(充填剤処理剤)を充填した。混合物を30分間撹拌した後、温度を90℃に設定した。この温度(90℃)を減圧下で30分間維持した後、50℃未満に冷却した。691.58gのDAW−45(Al2O3充填剤)及び3.45gのMgO2を添加した。この混合物(M−1)を、減圧下で室温(<30℃)で30分間混合した。以下表5に記載の通りの促進剤のパッケージ及びラジカル開始剤を更に添加して粘着剤組成物を調製した。2段階でZ−6030を充填して、表4に記載の総量に到達させた。2段階での充填において、各段階の間に、室温で30分間混合を行った。
100max歯科用コップ中で、様々な重量比(60:40、50:50、40:60及び35:65それぞれ)でMCP−2及びSRD−1の混合物14.5gを作製した。49.8gのCB−A20S(Z−6341で前処理)、33.2gのAl−43−ME(Z−6341で前処理)及び0.5gのMgOをこの混合物に添加した。この混合物(M−4)を2000rpmで15秒混合し、10分間の間隔を開けて2回以上混合を繰り返した。以下表5に記載の通りの促進剤のパッケージ及びラジカル開始剤を更に添加して粘着剤組成物を調製した。
TCA製剤に対する粘性率の測定:以下の実施例では、Brooksfielde円錐平板型粘度計(DV−II、スピンドル#52、速度2rpm)及びBrooksfield RVF粘度計(スピンドル#7、速度2rpm(低せん断)及び20rpm(高せん断))を利用して、様々な熱伝導性粘着剤製剤の粘度を求めた。
Claims (15)
- (I)クラスタ化官能性ポリオルガノシロキサン、(II)シリコーン用反応性希釈剤、(III)熱伝導性の充填剤を含む充填剤、(III’)充填剤処理剤、及び(IV)ラジカル開始剤を含む熱伝導性の熱ラジカル硬化型シリコーン組成物を形成するための方法であって、
(A)
a)1分子当たり平均して少なくとも2つの脂肪族不飽和有機基を有するポリオルガノシロキサン、
b)1分子当たり平均して4〜15個のケイ素原子、及び成分a)中の脂肪族不飽和有機基当たり少なくとも4個のケイ素結合水素原子を有する、ポリオルガノ水素シロキサン、及び
c)1分子当たり、少なくとも1つの脂肪族不飽和有機基、及びアクリレート基及びメ
タクリレート基から選択される1つ以上の硬化性基を有する反応性分子種の、
d)ヒドロシリル化触媒及びe)異性体還元剤の存在下での反応による反応生成物を含む、クラスタ化官能性ポリオルガノシロキサンを準備することと、
(B)熱伝導性充填剤を含む充填剤(III)、充填剤処理剤(III’)、及びシリコーン用反応性希釈剤(II)及びクラスタ化官能性ポリオルガノシロキサン(I)のうちの少なくとも1種を混合することにより混合物を形成することと、
(C)混合物を50℃〜110℃の温度に加熱して、少なくとも1種のシリコーン用反応性希釈剤(II)及びクラスタ化官能性ポリオルガノシロキサンの存在下で、熱伝導性充填剤を充填剤処理剤(III’)により処理することと、
(D)工程(B)の混合物がシリコーン用反応性希釈剤(II)及びクラスタ化官能性ポリオルガノシロキサン(I)の両方を含有する場合でないとき、混合物がシリコーン用反応性希釈剤(II)とクラスタ化官能性ポリオルガノシロキサン(I)の両方を含有するよう、シリコーン用反応性希釈剤(II)又はクラスタ化官能性ポリオルガノシロキサン(I)のいずれかを混合物に導入することと、次に、
(E)前記混合物を30℃以下に冷却させた後、ラジカル開始剤(IV)を混合物に配合して、熱伝導性の熱ラジカル硬化型シリコーン組成物を形成することと、を含む、方法。 - (F)工程(E)の前に少なくとも1種の追加成分を前記混合物に配合することであって、前記少なくとも1種の追加成分が(III)追加量の、熱伝導性充填剤を含む充填剤、(III’)追加量の、充填剤処理剤、(V)湿気硬化開始剤、(VI)架橋剤、(VII)湿気硬化型ポリマー、(VIII)溶媒、(IX)粘着促進剤、(X)着色剤、(XI)反応希釈剤、(XII)腐食防止剤、(XIII)重合阻害剤、(XIV)酸受容体、及びこれらの任意の組み合わせからなる群から選択される、配合すること、を更に含む、請求項1に記載の方法。
- 前記シリコーン用反応性希釈剤(II)が、
a)1分子当たり平均して10〜200個のケイ素原子を有するポリオルガノ水素シロキサン、及び
b)1分子当たり、少なくとも1つの脂肪族不飽和有機基及び1つ以上の硬化性基を有する第2の反応性分子種、を、
c)第2の異性体還元剤及びd)第2のヒドロシリル化触媒及びe)前記第2のヒドロシリル化触媒の阻害剤の存在下で反応させることによる反応生成物を含む、請求項1又は2に記載の方法。 - 前記シリコーン用反応性希釈剤(II)が、クラスタ化官能性ポリオルガノシロキサン(I)及びシリコーン用反応性希釈剤(II)を合わせた総重量の20〜90重量%を構成する、請求項1〜4のいずれか一項に記載の方法。
- (I)クラスタ化官能性ポリオルガノシロキサン、熱伝導性充填剤を含む充填剤、(III’)充填剤処理剤、及び(IV)ラジカル開始剤を含む熱伝導性の熱ラジカル硬化型シリコーン組成物を形成するための方法であって、
(A)
a)1分子当たり平均して少なくとも2つの脂肪族不飽和有機基を有するポリオルガノシロキサン、
b)1分子当たり平均して4〜15個のケイ素原子、及び成分a)中の脂肪族不飽和有機基当たり少なくとも4個のケイ素結合水素原子を有する、ポリオルガノ水素シロキサン、及び
c)1分子当たり、少なくとも1つの脂肪族不飽和有機基、及びアクリレート基及びメタクリレート基から選択される1つ以上の硬化性基を有する反応性分子種、を
d)ヒドロシリル化触媒及びe)異性体還元剤の存在下で反応させることによる反応生成物を含む、クラスタ化官能性ポリオルガノシロキサン(I)を準備することと、
(B)熱伝導性充填剤を含む充填剤(III)、充填剤処理剤(III’)、及びクラスタ化官能性ポリオルガノシロキサン(I)を混合することにより混合物を形成することと、
(C)混合物を50℃〜110℃の温度に加熱して、前記クラスタ化官能性ポリオルガノシロキサンの存在下で、熱伝導性充填剤を前記充填剤処理剤(III’)により処理することと、次に、
(D)混合物を30℃以下に冷却して、ラジカル開始剤(IV)を混合物に配合することと、を含む方法。 - 更に、
(E)工程(D)の前に少なくとも1種の追加の任意成分を前記混合物に配合することであって、前記少なくとも1種の追加成分が(III)追加量の、前記熱伝導性充填剤を含む充填剤、(III’)追加量の、充填剤処理剤、(V)湿気硬化開始剤、(VI)架橋剤、(VII)湿気硬化型ポリマー、(VIII)溶媒、(IX)粘着促進剤、(X)着色剤、(XI)反応希釈剤、(XII)腐食防止剤、(XIII)重合阻害剤、(XIV)酸受容体、及びこれらの任意の組み合わせからなる群から選択される、配合すること、を含む、請求項6に記載の方法。 - 前記熱伝導性充填剤が、前記熱伝導性の熱ラジカル硬化型シリコーン組成物の合計量の30〜80体積%を構成する、請求項1〜7のいずれか一項に記載の方法。
- 前記クラスタ化官能性ポリオルガノシロキサン(I)が、前記クラスタ化官能性ポリオルガノシロキサン(I)及び前記シリコーン用反応性希釈剤(II)を合わせた総重量の20〜99.9重量%を構成する、請求項1〜4のいずれか一項に記載の方法。
- 前記異性体還元剤が、前記クラスタ化官能性ポリオルガノシロキサン(I)の総重量に対し、前記ポリオルガノシロキサンのSiH基の、反応性分子種の前記脂肪族不飽和基に対するβ付加を、前記異性体還元剤の非存在下で形成されたクラスタ化官能性ポリオルガノシロキサンと比較して少なくとも10%低減させる量で存在する、請求項1〜9のいずれか一項に記載の方法。
- 前記(VI)架橋剤及び前記湿気硬化型ポリマー(VII)が、両方とも熱伝導性の熱ラジカル硬化型シリコーン組成物中に存在し、前記架橋剤(VI)の量は、湿気硬化型ポリマー(VII)の総重量の0.001〜50重量%を構成し、前記湿気硬化型ポリマー(VII)の量は、前記熱伝導性の熱ラジカル硬化型シリコーン組成物の総重量の0.1〜5重量%を構成する、請求項2〜5及び7〜10のいずれか一項に記載の方法。
- 前記湿気硬化型ポリマー(VII)が、式:(OR7)3−zR6 zSi−Q−(R25 2SiO2/2)y−Q−SiR6 z(OR7)3−zのオルガノポリシロキサンポリマーを含む[式中、各R25は、独立して、1〜6個の炭素原子を有する一価の炭化水素ラジカルであり、各R6は、独立して、1〜6個の炭素原子を有する一価の炭化水素ラジカルであり、各R7は、独立して、アルキル基及びアルコキシアルキル基からなる群から選択され、Qは、二価の連結基であり、添字zは0、1又は2の値を有し、添字yは60〜1000の値を有する]、請求項2〜5及び7〜11のいずれか一項に記載の方法。
- 請求項1〜12のいずれか一項に記載の方法により形成された熱伝導性の熱ラジカル硬化型シリコーン組成物のエレクトロニクス用途での使用。
- 導電性を有する硬化させた支持体を形成する方法であって、
(a)請求項1〜12のいずれか一項に記載の方法に従って、熱伝導性の熱ラジカル硬化型シリコーン組成物を形成することと、
(b)前記熱伝導性の熱ラジカル硬化型シリコーン組成物を支持体に塗布することと、
(c)前記支持体上の前記熱伝導性の熱ラジカル硬化型シリコーン組成物を硬化させて、導電性硬化させた支持体を形成することと、を含む、方法。 - 熱伝導性の熱ラジカル硬化型シリコーン組成物を形成する方法であって、
(a)請求項1〜12のいずれか一項に記載の方法に従って、熱伝導性の熱ラジカル硬化型シリコーン組成物を形成することと、
(b)前記熱伝導性の熱ラジカル硬化型シリコーン組成物を硬化して、硬化熱伝導性の熱ラジカル硬化型シリコーン組成物を形成することと、を含む、方法。
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EP (1) | EP2954025B1 (ja) |
JP (1) | JP6531043B2 (ja) |
KR (1) | KR102170918B1 (ja) |
CN (1) | CN105189685B (ja) |
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US20150376488A1 (en) | 2015-12-31 |
KR102170918B1 (ko) | 2020-10-29 |
CN105189685A (zh) | 2015-12-23 |
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WO2014124367A1 (en) | 2014-08-14 |
EP2954025A1 (en) | 2015-12-16 |
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