JP5701062B2 - ヒドロキシアリール官能化重合体 - Google Patents
ヒドロキシアリール官能化重合体 Download PDFInfo
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- JP5701062B2 JP5701062B2 JP2010540912A JP2010540912A JP5701062B2 JP 5701062 B2 JP5701062 B2 JP 5701062B2 JP 2010540912 A JP2010540912 A JP 2010540912A JP 2010540912 A JP2010540912 A JP 2010540912A JP 5701062 B2 JP5701062 B2 JP 5701062B2
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- ASHNNDSJKNDDTJ-UHFFFAOYSA-N tert-butyl-[2-[tert-butyl(dimethyl)silyl]oxy-4-ethenylphenoxy]-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=C(C=C)C=C1O[Si](C)(C)C(C)(C)C ASHNNDSJKNDDTJ-UHFFFAOYSA-N 0.000 description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 229910052683 pyrite Inorganic materials 0.000 description 1
- NIFIFKQPDTWWGU-UHFFFAOYSA-N pyrite Chemical compound [Fe+2].[S-][S-] NIFIFKQPDTWWGU-UHFFFAOYSA-N 0.000 description 1
- 239000011028 pyrite Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010301 surface-oxidation reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000011191 terminal modification Methods 0.000 description 1
- UKZWNPNPWXPENV-UHFFFAOYSA-N tert-butyl-[4-(1,3-dithian-2-yl)phenoxy]-dimethylsilane Chemical compound C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C1SCCCS1 UKZWNPNPWXPENV-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CMUTXJXHVDKYAN-UHFFFAOYSA-L tetrabutylazanium difluoride Chemical compound [F-].[F-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC CMUTXJXHVDKYAN-UHFFFAOYSA-L 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 125000005323 thioketone group Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
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Description
「重合体」とは,一以上の単量体の重合生成物を意味し,二元共重合体、三元共重合体、四元共重合体等を含み,
「マー」又は「マー単位」とは,単一の反応体分子から誘導された重合体の部分(例えば,エチレン・マーは,一般式-CH2CH2-である)を意味し,
「共重合体」とは,典型的には,単量体である二つの反応体から誘導されたマー単位を含む重合体を意味し,ランダム,ブロック,セグメント化,グラフト等の共重合体を含み,
「共重合体」とは,典型的には単量体である少なくとも二つの反応体から誘導されたマー単位を含む重合体を意味し,二元共重合体,三元共重合体,四元共重合体等を含み,
「ランダム共重合体」とは,実質的に反復しないように及び実質的にブロックができないように組み入れられた各種類の構成単量体から誘導されたマー単位,すなわち,三以上の同一マーのセグメントを有する共重合体を意味し,
「反応性重合体」とは,関連する触媒又は開始剤の存在ゆえに,他の分子と直ちに反応する少なくとも一つの位置を有する重合体を意味し,該用語は,とりわけ,擬リビング及びカルボアニオン重合体を含んでおり,
「触媒組成物」とは,成分の単純な混合物,物理的又は化学的引力によって生じた多種の成分の錯体,一部又は全部の成分の化学反応生成物又は前述の組合せを範囲とする一般的な用語であり,その結果物が適切な種類の一以上の単量体に関する触媒活性を呈する組成物であり,
「ゴムムーニー粘度」とは,単数又は複数の充填剤のいずれをも添加する前の未硬化重合体のムーニー粘度であり,
「配合物ムーニー粘度」とは,とりわけ,未硬化又は部分的に硬化した重合体及び単数又は複数の充填剤を含む組成物のムーニー粘度であり,
「置換した」とは,対象となる基の本来の目的の妨げとならないヘテロ原子又は官能部(例えば,ヒドロカルビル基)を含有することを意味し,
「直接結合した」とは,原子又は基を介在しないで共有結合したことを意味し,
「ポリエン」とは,その最長部分又は鎖中に位置する少なくとも二つの二重結合を有する分子を意味し,特にジエン,トリエン等を含み,
「ポリジエン」とは,一以上のジエンからのマー単位を含む重合体を意味し,
「phr」とは,ゴム100重量部(pbw)当たりのpbwを意味し,
「非配位アニオン」とは,立体障害ゆえに触媒系の活性中心と配位結合を形成しない立体的に嵩高いアニオンを意味し,
「非配位アニオン前駆体」とは,反応条件下,非配位アニオンを形成できる化合物を意味し,
「ラジカル」とは,反応の結果としていずれかの原子を得るか失うかにかかわらず,他の分子との反応後に残存する分子の部分を意味し,
「アリール基」とは,フェニル基又は多環式芳香族ラジカルを意味し,
「末端」とは,重合体鎖の端部を意味し,
「末端部位」とは,末端に位置する基又は官能部を意味する。
ランタニド化合物に対するアルキル化剤(アルキル化剤/Ln)は,約1:1〜約200:1,好適には約2:1〜約100:1,より好適には約5:1〜約50:1であり,
ランタニド化合物に対するハロゲン含有化合物(ハロゲン原子/Ln)は,約1:2〜約20:1,好適には約1:1〜約10:1,より好適には約2:1〜約6:1であり,
ランタニド化合物に対するアルミノキサン,特にランタニド化合物中のランタニド原子当量に対するアルミノキサン中のアルミニウム原子当量(Al/Ln)は,約10:1〜約50,000:1,好適には約75:1〜約30,000:1,より好適には約100:1〜約1,000:1であり,
ランタニド化合物に対する非配位アニオン又は前駆体(An/Ln)は,約1:2〜約20:1,好適には約3:4〜約10:1,より好適には約1:1〜約6:1である。
(1) インサイチュ 触媒成分を,単量体及び溶媒(又は単にバルク単量体)を含有する溶液に添加する。添加は段階的又は一斉に行ってもよい。後者の場合,アルキル化剤を好適には最初に添加し,順次ランタニド化合物,ニッケル含有化合物(使用する場合)および(使用する場合)ハロゲン含有化合物又は非配位アニオン又は非配位アニオン前駆体が続く。
(2) 予備混合 成分を,単数又は複数の共役ジエン単量体を導入する前に,重合系外で,一般に約-20°〜80℃の温度で混合できる。
(3) 単数又は複数の単量体の存在下での予備形成 触媒成分を,少量の単数又は複数の共役ジエン単量体の存在下,約-20°〜80℃の温度で混合できる。共役ジエン単量体の量は,ランタニド化合物のモル当たり約1〜約500モル,好適には約5〜約250モル、より好適には約10〜約100モルの範囲に及ぶことができる。得られた触媒組成物を重合する単数又は複数の共役ジエン単量体の残分に添加する
(4) 二段階法
(a) 共役ジエン単量体の不在又は少量の共役ジエン単量体の存在下,アルキル化剤を,ランタニド化合物と約−20°〜80℃の温度で混合する。
(b) 前述の混合物及び残存する構成成分を段階的又は一斉のいずれの方法で重合する単数又は複数の共役ジエン単量体の残分に注入する(使用する場合,Ni含有化合物はいずれの段階にも含めることができる)。
一以上の触媒成分の溶液を,前述の方法により重合系外で調製する場合,有機溶媒又はキャリヤーを好適には使用する。有用な有機溶媒としては,前述のものが挙げられる。
式(VIIf)及び(VIIg)と上記式(IV)を比較することで,式(IV)で表わされる末端官能部において,R6及びR3の一部分が連結して,単数又は複数の原子と共に結合し(直接又は間接的に),R3アリール基と結合又は融合する環を形成することが分かる。これは下記一般式によって図示的に表わすことができる。
これらの例において,スチレン(ヘキサン中33%),ヘキサン,n−ブチルリチウム(ヘキサン中1.60M),2,2−ビス(2’−テトラヒドロフリル)プロパン(1.6Mヘキサン溶液,CaH2上で保存)及び2,6−ジ−tert−ブチル−4−メチルフェノール(BHT)ヘキサン溶液を使用した。
表1a(酸化チタン,ルチル),
表1b(カーボンブラック及び水酸化アルミニウム),
表1c(カーボンブラック及び酸化チタン)及び
表1d(カーボンブラック)。
これらの処方で採用した酸化チタンは,粒径約0.17μmで比重約4.2を有するトロノックス(Tronox 商標)CR-834,アルミナ安定化TiO2(Tronox Inc.社製,Oklahoma City, Oklahoma)であり,採用した水酸化アルミニウムは,メディアン粒径約1μmで比重2.42g/cm3を有するハイドラル(Hydral 商標)PGA-HD,Al(OH)3粒子 (Almatis, Inc.社製 Leetsdale, Pennsylvania)である。これら(及び同様のその後の表)において,N−フェニル−N’−(1,3−ジメチルブチル)−p−フェニレンジアミン(6PPD)は酸化防止剤として作用し,2,2’−ジチオビス(ベンゾチアゾール)(MBTS),N−tert−ブチルベンゾチアゾール−2−スルフェンアミド(TBBS)及びN,N’−ジフェニルグアニジン(DPG)は促進剤として作用する。ブラックオイルは,比較的少量の多環式芳香族(PCA)化合物を含む伸展油である。
窒素雰囲気下,乾燥フラスコへ,3,4−ジヒドロキシベンゾフェノン約6.0g,トリエチルアミン約6.0g,4-(ジメチルアミノ)ピリジン約0.14g及びDMF30mLを注入した。その後,tert-ブチル(クロロ)ジメチルシラン約9.3gのDMF溶液30mLを滴下して添加した。
窒素雰囲気下,乾燥フラスコへ,3,4−ジヒドロキシベンズアルデヒド約10.0g,トリエチルアミン約16.1g,4−(ジメチルアミノ)ピリジン約0.35g及びDMF60mLを注入した。tert−ブチル(クロロ)ジメチルシラン約24.0gのDMF溶液60mLをその後滴下して添加した。
N2でパージした撹拌機を備えた反応器へ,ヘキサン1.39kg,スチレン溶液0.37kg及びブタジエン溶液2.27kg(ヘキサン中21.6wt%)を添加した。反応器へ,n−ブチルリチウム溶液3.19mL,引き続き,2,2−ビス(2’−テトラヒドロフリル)プロパン溶液1.13mLを注入した。反応器ジャケットを50℃へ加熱し,重合を約75分間続行した。ポリマーセメントを,2,6−ジ−tert−ブチル−4−メチルフェニルを含有するイソプロパノール中で失活する前に,室温へ冷却し,その後ドラム乾燥した。これを以下例3と呼ぶ。
例3〜5からの重合体を上記表1aに示した処方で使用して,組成物を得,それから以下例6〜8と名付けた加硫物を調製した。
N2パージした撹拌機を備えた反応器へ,ヘキサン1.39kg,スチレン溶液0.37kg及びブタジエン溶液2.27kg(ヘキサン中21.6wt.%)を添加した。反応器へ,トルエン中3.0MのHMI1.62mL及びn−ブチルリチウム溶液3.19mL,引き続き,2,2−ビス(2’−テトラヒドロフリル)プロパン溶液1.13mLを注入した。反応器ジャケットを50℃へ加熱し,重合を60分間継続した。ポリマーセメントを,失活前に,室温へ冷却し,前記のようにドラム乾燥した。これを以下例12と呼ぶ。
例12〜14からの重合体を上記表1cに示した処方で使用して,組成物を得,それから各々以下例15〜17と名付けた加硫物を調製した。
乾燥フラスコへ,3,4−ジヒドロキシベンズアルデヒド約4.83g,イミダゾール約4.80g及びTHF50mLを窒素雰囲気下注入した。n−ブチルリチウム約43.8mLの1.6M溶液を滴下して添加する前に,溶液を−78℃へ冷却した。
例25: ヘキサン中1.0M(ポリマーセメント100g当たり0.3mL)のBTBDMSBA(例2から)を添加し,TBAF溶液(THF中1.0M,ポリマーセメント100g当たり0.7mL)を添加する前に,セメントと65℃の水槽中約30分間反応させ,容器を25℃水槽中約4時間回転させた。
例26: ヘキサン中0.33M(ポリマーセメント100g当たり0.91mL)のBTMSBA(例21から)を添加し,セメントと65℃の水槽中約30分間反応させた。
例27 : ヘキサン中0.33M(ポリマーセメント100g当たり0.91mL)のBTMSBA (from 例21から)を添加し,イソプロパノール中1.0M(ポリマーセメント100g当たり1.0mL)のHClを添加する前に,セメントと65℃の水槽中約30分間反応させ,容器を50℃水槽中約30分間回転させた。
例22〜27からの重合体を上記表1dに示した処方で使用して,組成物を得,それから各々以下例28〜33と名付けた加硫物を調製した。
ブタジエン溶液(すべてヘキサン中),スチレン(ヘキサン中33%),ヘキサン,n−ブチルリチウム(n−BuLi,ヘキサン中1.69M),2,2−ビス(2’−テトラヒドロフリル)プロパン(1.6Mヘキサン溶液,CaH2で保管)及びブチル化ヒドロキシトルエン(BHT)ヘキサン溶液をこれらの例では使用した。
Sigma-Aldrich Co.社からは,3,4−ジヒドロキシベンズアルデヒド(97%),1,3−プロパンジチオール(99%),p−トルエンスルホン酸一水和物(98.5%),酢酸エチル(99.5%及び4−ジ(メチルアミノ)ピリジン(DMAP,99%),
ACROS Organics社からは,tert−ブチルジメチルシリルクロリド(98%)及びTBAF(約5%水を含有するTHF中1M)。
マグネティックスターラーバー及び冷却管を備える乾燥した500mLフラスコへ,3,4−ジヒドロキシベンズアルデヒド8.2g,p−トルエンスルホン酸一水和物1.6g及びTHF100mL,引き続き,1,3−プロパンジチオール6mLのTHF30mL溶液を添加した。この混合物を窒素雰囲気下約12時間還流した。室温へ冷却後,混合物をろ過し,無水MgSO4で乾燥する前に,ろ液を,飽和NaHCO3(100mL)で二回洗浄し,飽和NaCl溶液(100mL)で一回洗浄した。溶媒を留去し,残渣を,ヘキサン中50%酢酸エチルを溶出溶媒として使用するシリカゲルカラムクロマトグラフィーを用いて精製した。油状生成物(13.3g,収率99%)が得られ,CDCl3中の1H及び13C NMRにより下記の構造であると確認した。
N2でパージした撹拌機を備えた反応器へ,ヘキサン1.47kg,スチレン溶液0.41kg及びブタジエン溶液2.60kg(ヘキサン中20.9%)を添加した。反応器へ,n−BuLi溶液約3.2mL,引き続き,2,2−ビス(2’−テトラヒドロフリル)プロパン溶液1.1mLを注入した。反応器ジャケットを50℃へ加熱し,約30分後,バッチ温度が約64℃でピークを打った。更に約30分後,ポリマーセメントを,BHTを含有するイソプロパノール中に滴下し,ドラム乾燥した。
例36で採用したのと同様のN2でパージした反応器へ,ヘキサン1.37kg,スチレン溶液0.41kg及びブタジエン溶液2.71kg(ヘキサン中20.1%)を添加した。反応器へ,例34からのジチアン1.0Mヘキサン溶液5.9mL,引き続き,n−BuLi溶液3.9mLを注入した。約5分後,2,2−ビス(2’−テトラヒドロフリル)プロパン溶液1.1mLを添加した。反応器ジャケットを50℃へ加熱し,約35分後,バッチ温度が約67℃でピークを打った。
試料37及び38では,イソプロパノール,
試料39では,BTBDMSBA(例35より),ヘキサン中1.0M(ベンズアルデヒドとLi原子の比率1:1を使用),及び
試料40では,ヘキサン中SnCl4,0.25M(SnとLiの比率1:1を使用)。
各試料を50℃水槽中で更に約30分間撹拌した。試料37〜40からの保護基を,室温で(約2時間)TBAF溶液(保護基の計算量と比べて約20%モル過剰)と反応させることで加水分解した。
上記表9a及び9bからの処方を用いて,補強充填剤を含有する加硫可能なエラストマー配合物を試料36〜40から調製した。表9aの処方からの調製物を各々例41〜45と名付け,一方,表9aの処方からの調製物を各々例46〜50と名付けた。組成物を171℃で約15分間硬化した。
ブタジエン溶液(すべてヘキサン中),スチレン溶液(ヘキサン中33%),ヘキサン,n-ブチルリチウム(n−BuLi,ヘキサン中1.60M),2,2−ビス(2’−テトラヒドロフリル)プロパン(ヘキサン中1.6M溶液,CaH2上で保管)及びBHTヘキサン溶液を,これらの例中で使用した。
Sigma-Aldrich Co.社からは,2,3−ジヒドロキシベンズアルデヒド(97%),3,4−ジヒドロキシベンズアルデヒド(97%),3,5−ジヒドロキシベンズアルデヒド(98%),2,5−ジヒドロキシベンズアルデヒド(98%),3,4,5−トリヒドロキシベンズアルデヒド一水和物(98%),メチルトリフェニルホスフェニウムブロミド(MTP−Br,98%),酢酸エチル(99.5%)及びDMAP(99%),
ACROS Organics社からは,tert−ブチルジメチルシリルクロリド(98%)及びTBAF(約5%水を含有するTHF中1M)。
撹拌し冷却(0℃)したMTP-Br23.2gの無水THF100mL溶液中へ,n−BuLi溶液40.6mLを窒素雰囲気下,滴下して添加した。約15分後,BTBDMSBA約22.3g(例35から)のTHF溶液30mLを,注射器を介して滴下した。得られた黄色懸濁液を,NH4Clで処理する前に約4時間撹拌した。この溶液をろ過し真空下濃縮した。残渣を,ヘキサン中5%酢酸エチルを溶出溶媒として使用するシリカゲルカラムクロマトグラフィーによって精製し,集めた無色油約20.6g(収率94%)を得た。1H及び13C NMRで,化合物が,3,4−ジ(tert−ブチルジメチルシロキシ)スチレン(DTBDMSOS)であることを確認した。
N2でパージした撹拌機を備えた反応器へ,ヘキサン0.81kg,スチレン溶液0.21kg及びブタジエン溶液1.20kg(ヘキサン中22.6%)を添加した。反応器へ,n−BuLi溶液約1.9mL,引き続き,2,2−ビス(2’−テトラヒドロフリル)プロパン溶液0.55mLを注入した。反応器ジャケットを50℃へ加熱し,約30分後,バッチ温度は約59℃でピークを打った。
例53と同様のN2でパージした反応器中での一連の重合を,ヘキサン0.81 kg,スチレン溶液0.21kg及びブタジエン溶液1.20kg(ヘキサン中22.6%)を含む混合物について行った。混合物は,特に採用したDTBDMSOS(ヘキサン中1.0M)及びn−BuLi溶液の量が異なる。
53 DTBDMSOS溶液2.6mL及び開始剤2.01mL,
54 DTBDMSOS溶液9.2mL及び開始剤1.92mL,
55 DTBDMSOS溶液14.3mL及び開始剤1.80mLである。
また,各混合物へ,2,2−ビス(2’−テトラヒドロフリル)プロパン溶液0.55mLを添加した。反応器ジャケットを各々50℃へ加熱し,バッチ温度は,各々約56℃(約32分後),約57℃(約30分後)及び約56℃(約30分後)ピークを打った。十分なTBAF溶液を,TBAFの比率がDTBDMSOSに対して各々約6:5となるように添加し,これら混合物を各々室温で約2時間撹拌した。
例52と同様のN2でパージした反応器へ,ヘキサン1.55kg,スチレン溶液0.41kg及びブタジエン溶液2.52kg(ヘキサン中21.6%)を添加した。反応器にn−BuLi溶液約3.3mL,引き続き,2,2−ビス(2’−テトラヒドロフリル)プロパン溶液1.1mLを注入した。反応器ジャケットを50℃へ加熱し,約30分後,バッチ温度が約63℃でピークを打った。
試験試料を上記のように調製し,試験した。
上記表9a及び9bからの処方を用いて,補強充填剤を含有する加硫可能なエラストマー配合物を試料52〜55から調製した。表9aの処方からの調製物を各々例60〜63と名付け,一方,表9aの処方からの調製物を各々例64〜67と名付けた。かかる組成物を171℃で約15分間硬化することで,加硫物を調製した。
乾燥した250mLのマグネティックスターラーバーを備えたフラスコへ,3,4,5-トリヒドロキシベンズアルデヒド約5.0g,DMAP約0.3g,THF60mL及びトリエチルアミン1.0mLを添加し,引き続き,tert−ブチルジメチルシリルクロリド約15.2gのTHF30mL溶液を注射器で添加した。本混合物を,室温で約1時間(窒素雰囲気下)撹拌した。固体は混合物からろ過され,ろ液を溶出溶媒として10%酢酸エチルのヘキサン溶液を採用するシリカゲルカラムクロマトグラフィーを使用して精製する前に,溶媒を留去した。ワックス状の生成物(15.3g,収率96%)を得た。1H及び13C NMRにより,組成物が,3,4,5−トリ(tert−ブチルジメチルシロキシ)ベンズアルデヒドだと確認した。
窒素雰囲気下,MTP−Br約11.5gの冷却(0℃)無水THF100 mL溶液を撹拌し,n−BuLi溶液約19.5mLを滴下した。約1.0分後,例6〜8からの生成物15.0gのTHF30mL中の溶液を,注射器を介して滴下した。NH4Clで処理する前に,得られた黄色懸濁液を約4時間撹拌した。本溶液をろ過し真空下濃縮した。残渣を,ヘキサン中の5%酢酸エチルを溶出溶媒として使用するシリカゲルカラムクロマトグラフィーによって精製し,約13.4g(収率90%)の無色油の集合体が得られた。1H及び13C NMRにより,組成物が,3,4,5−トリ(tert−ブチルジメチルシロキシ)スチレン(TTBDMSOS)であることを確認した。
N2でパージした撹拌機を備えた反応器へ,ヘキサン約1.55kg,スチレン溶液約0.41kg及びブタジエン溶液(ヘキサン中21.6%)約2.52kgを添加した。
例70と同様のN2でパージした 反応器中での重合を実施した。開始剤溶液(ここでは約2.9mL)の量以外,添加した材料の量は例70からの量と同一である。反応器ジャケットを50℃へ加熱し,約35分後,バッチ温度は約64℃でピークを打った。
試料71−イソプロパノール,
試料72−SnCl4,ヘキサン中0.25M(Sn対Liの比率1:1を使用),
試料73−DMI,トルエン中1.0M,
試料74−APMDEOS,ヘキサン中1.0Mで
各試料を50℃の水槽中で更に約30分間撹拌した。
例70及び73〜74の重合体だけでなく,DMI及びAPMDEOSで停止したSBR(すなわち,ポリマー鎖中に含まれるB単位がない)を,上記で定義した手順を用いて,試験試料を調製するのに使用した。
上記表9a及び9bからの処方を使用して,補強充填剤を含有する加硫可能なエラストマー配合物を試料70〜74から調製した。表9aの処方からの調製物を各々例76〜81と名付け,一方,表9b処方からの調製物を各々例82〜87と名付けた。かかる組成物を171℃で約15分間硬化することで,加硫物を調製した。
Claims (21)
- 一以上の種類のポリエン・マー及び少なくとも一つの官能化単位を含む官能性重合体の製造方法であって,前記官能化単位が,少なくとも一つの直接結合したOR基(式中、Rが加水分解性の保護基である)を有するアリール基を含み,前記方法が,
a)開始化合物、並びに少なくとも一つの種類のポリエン、少なくとも一つの種類のC8〜C20ビニル芳香族化合物、及び式CH2=CHR1(式中、R1は、少なくとも一つのOR2置換基を有し、単一の芳香族環又は二以上の融合した芳香族環を含むアリール基であり、R2は、加水分解性の保護基である)で表されるエチレン系不飽和化合物を含むエチレン系不飽和モノマーを含む溶液を用意する工程と,
b)前記開始化合物に,カルボアニオン重合体を提供するように,前記エチレン系不飽和モノマーのアニオン重合を開始させる工程とを備え,
少なくとも一つの官能化単位が,前記R1の基を含有するモノマーから誘導されており、
前記少なくとも一つの官能化単位の一以上が,直接結合した二つのOR基(式中、各Rが加水分解性の保護基である)を有するアリール基を含む、前記官能性重合体の製造方法。 - 前記カルボアニオン重合体を一以上の活性水素原子含有化合物とを反応させ,それによって,前記カルボアニオン重合体を失活する工程と、前記OR基の各々を加水分解する工程を更に備える請求項1に記載の方法。
- 直接結合した二つのOR基を有するアリール基を含む前記少なくとも一つの官能化単位の一つが,停止化合物から誘導されている請求項1に記載の方法。
- 前記二つのOR基が,前記アリール基の隣接する炭素原子に直接結合している請求項3に記載の方法。
- 前記官能性重合体が,前記開始化合物から誘導された官能化単位を含む請求項1に記載の方法。
- 前記開始化合物が,一般式R1ZQ−M[式中,Mはアルカリ金属原子であり,Zは単結合又は置換もしくは非置換の環状アルキレン,非環状アルキレンもしくはアリーレン基であり,QはC,N又はSn原子を介してMと結合する基であり、R1は請求項1において定義された通りであり、但し、各R2はMに対しても非反応性である]を有する請求項5に記載の方法。
- 前記カルボアニオン重合体が,複数のAマー及び少なくとも三つのBマーを含み,前記Aマーの各々がエチレン系不飽和部を含み,前記Bマーの各々が,少なくとも一つの直接結合したOR基を有するフェニル基を含む請求項1に記載の方法。
- 官能化単位が前記重合体の末端にあり,前記方法が,前記カルボアニオン重合体を,少なくとも一つのヘテロ原子を含む官能部を更に含む停止化合物と反応させる工程を更に備える請求項1に記載の方法。
- 前記官能性重合体を少なくとも一つの種類の粒子状充填剤と混合して、充填組成物を提供する工程を更に備える請求項1に記載の方法。
- 前記充填組成物が、一以上の追加の種類のゴムを更に含む請求項9に記載の方法。
- 加硫物を提供するため、前記充填組成物を加熱する工程を更に含む請求項10に記載の方法。
- 一以上の種類のポリエン・マー及び少なくとも一つの官能化単位を含む官能性重合体の製造プロセスであって、前記官能化単位が、少なくとも二つの直接結合したOR基(式中、各Rは加水分解性の保護基である)を有するアリール基を含み、前記方法が、
a)開始化合物、並びに少なくとも一つの種類のポリエン及び式CH2=CHR1(式中、R1は少なくとも二つのOR2置換基を含むアリール基であり、各R2は加水分解性の保護基である)で表されるエチレン系不飽和化合物を含むエチレン系不飽和モノマーを含む溶液を用意する工程と、
b)前記開始化合物に,カルボアニオン重合体を提供するように,前記エチレン系不飽和モノマーのアニオン重合を開始させる工程とを備え,
少なくとも一つの官能化単位が,前記エチレン系不飽和化合物から誘導されている、前記官能性重合体の製造プロセス。 - 前記カルボアニオン重合体を、カルボアニオン重合体と反応できる官能部を含む停止化合物と反応させる工程を更に備える請求項12に記載のプロセス。
- 前記カルボアニオン重合体が、官能化単位を末端に含む請求項12に記載のプロセス。
- 前記カルボアニオン重合体を一以上の活性水素原子含有化合物とを反応させ,それによって,前記カルボアニオン重合体を失活する工程と、前記OR基の各々を加水分解する工程を更に備える請求項12に記載のプロセス。
- 前記少なくとも一つの官能化単位の一つが,前記停止化合物から誘導されている請求項13に記載のプロセス。
- 前記停止化合物から誘導されている前記官能化単位の二つのOR基が,前記アリール基の隣接する炭素原子に直接結合している請求項16に記載のプロセス。
- 一般式CH2=CHR1を有する前記化合物により提供されるマーの量が、前記カルボアニオン重合体内のマーの総数に対して、1%より少ない請求項12に記載のプロセス。
- 前記官能性重合体を少なくとも一つの種類の粒子状充填剤と混合して、充填組成物を提供する工程を更に備える請求項12に記載のプロセス。
- 前記充填組成物が、一以上の追加の種類のゴムを更に含む請求項19に記載のプロセス。
- 加硫物を提供するため、前記充填組成物を加熱する工程を更に含む請求項20に記載のプロセス。
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