JP5422393B2 - 重合性組成物、該重合性組成物から得られる透明部材およびその用途 - Google Patents
重合性組成物、該重合性組成物から得られる透明部材およびその用途 Download PDFInfo
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- JP5422393B2 JP5422393B2 JP2009546128A JP2009546128A JP5422393B2 JP 5422393 B2 JP5422393 B2 JP 5422393B2 JP 2009546128 A JP2009546128 A JP 2009546128A JP 2009546128 A JP2009546128 A JP 2009546128A JP 5422393 B2 JP5422393 B2 JP 5422393B2
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- 239000010419 fine particle Substances 0.000 claims description 188
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- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 claims description 14
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- 238000006116 polymerization reaction Methods 0.000 claims description 14
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 12
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- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 9
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- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 claims description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 6
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 5
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- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 4
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- OERNJTNJEZOPIA-UHFFFAOYSA-N zirconium nitrate Chemical compound [Zr+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O OERNJTNJEZOPIA-UHFFFAOYSA-N 0.000 claims description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
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- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 3
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 claims description 3
- 229910000348 titanium sulfate Inorganic materials 0.000 claims description 3
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 claims description 2
- 229910001111 Fine metal Inorganic materials 0.000 claims 1
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 238000000465 moulding Methods 0.000 description 13
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
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- 238000010908 decantation Methods 0.000 description 11
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 11
- 229910052718 tin Inorganic materials 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 10
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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- MLGITEWCALEOOJ-UHFFFAOYSA-N 2-(thiiran-2-ylmethylsulfanylmethyl)thiirane Chemical compound C1SC1CSCC1CS1 MLGITEWCALEOOJ-UHFFFAOYSA-N 0.000 description 6
- 229910015900 BF3 Inorganic materials 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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- 108010010296 urea carboxylase (hydrolyzing) Proteins 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Description
前記金属塩は、塩化チタン、塩化スズ、水酸化バリウム、水酸化アルミニウム、硝酸亜鉛、硝酸セリウム、硫酸チタン、塩化酸化ジルコニウムおよび硝酸ジルコニウムから選択される少なくとも一種であり、
前記有機物は、ヘキサン酸、デカン酸、ヘキサンチオール、ヘキサノール、ヘキシルアミンおよびオレイン酸から選択される少なくとも一種であり、
前記重合性組成物から得られる成形体のe線の屈折率が、1.71以上である、ことを特徴とする重合性組成物。
[9] [5]乃至[7]のいずれかに記載の透明部材からなることを特徴とする光学レンズ。
なお、本発明において重合性組成物は成形前の組成物を意味し、液状混合物および固形状混合物のいずれをも含むものである。
本発明に係る樹脂組成物は、重合性化合物または樹脂成分と、高温高圧水を反応場として生成された、金属微粒子表面に有機物が結合している有機修飾微粒子と、を含む。
本発明における有機修飾微粒子は、媒体中に分散させた場合に、その組成物が光学用途として有用な高い透明性を示すことが望まれるため、これを有機溶剤に分散したときに透明コロイドを与えるものであることが望ましい。有機修飾微粒子を媒体中に分散させた組成物および成形体が高い透明性を示すということは、当該有機修飾微粒子が光の波長に比べ十分小さな粒子として媒体中で挙動していること、波長400nm〜800nmの可視領域において吸収すなわち着色がなく、光学用途として適当であることを示している。
なお、有機修飾微粒子は、当該粒子を含む光学材料用添加剤として用いることもできる。
ここで、亜臨界状態の水とは、温度が200℃以上374℃以下、圧力が、5MPa以上22.1MPa以下の条件下の亜臨界水を示し、超臨界状態の水とは、温度が374℃を超え、圧力が、22.1MPaを超える条件下の超臨界水を示す。特に、超臨界水の領域では、水と有機物が均一相を形成すること、水や酸が触媒として作用することで、触媒を添加しなくても有機反応が進行することが判っており、粒子と有機物が結合を形成し易くなる。
金属塩および有機修飾分子等の添加量は、金属塩の金属成分の種類や、有機修飾分子の種類などによって変動するため特に限定されるものではない。
光学材料用添加剤としては、単離された有機修飾微粒子をそのまま用いてもよく、単離された有機修飾微粒子に所定の添加剤を添加して用いてもよく、反応後に得られた混合物をそのまま用いてもよい。
ペンタンジチオール、ヘキサンジチオール、ヘプタンジチオール、オクタンジチオール、ノナンジチオール、デカンジチオール、ウンデカンジチオール、ドデカンジチオール、トリデカンジチオール、テトラデカンジチオール、ペンタデカンジチオール、ヘキサデカンジチオール、ヘプタデカンジチオール、オクタデカンジチオール、ノナデカンジチオール、エイコサンジチオールを挙げることができ、1種または2種以上組み合わせて用いることができる。
金属微粒子および有機修飾分子等の添加量は、金属微粒子の金属成分の種類や、有機修飾分子の種類などによって変動するため特に限定されるものではない。
被覆層を構成する無機物としては、ケイ素酸化物(SiO2)、酸化ジルコニウム、酸化亜鉛、酸化スズ、酸化アンチモン、酸化アルミニウム等を挙げることができる。金属微粒子表面に無機物からなる1層以上の被覆層を有することにより、透明部材の特性を劣化させる原因となる金属微粒子の活性を抑制することができる。
以下に、無機物としてケイ素酸化物(SiO2)を含む被覆層の調製方法について述べる。
(1)核(A)に対する重量比がSiO2換算で0.001〜10となるケイ素酸化物をpH<7の条件下で、核(A)と反応させる工程
(2)核(A)に対する重量比がSiO2換算で0.001〜10となるケイ素酸化物をpH≧7の条件下で、(1)で得られた被覆超微粒子と反応させる工程
まず、核微粒子即ち核(A)と、核(A)に対する重量比がSiO2換算で0.001〜10となるケイ素酸化物を、pH<7の条件下で反応させる。
工程(1)で得られた被覆超微粒子あるいはゾル液を必要に応じて解こうした後、続いて、(1)で得られた被覆超微粒子と、核(A)に対する重量比がSiO2換算で0.001〜10となるケイ素酸化物を、pH≧7の条件下で反応させる。
なお、以下において、金属微粒子として、上述の方法により得られたスズ修飾ルチル型酸化チタン超微粒子、または、二層ケイ素酸化物被覆スズ修飾ルチル型酸化チタン超微粒子を用いた例により説明する。
有機修飾微粒子は、スズ修飾ルチル型酸化チタン超微粒子、または、二層ケイ素酸化物被覆スズ修飾ルチル型酸化チタン超微粒子の表面を有機物で修飾、被覆、改質することにより、本発明に用いられる有機修飾微粒子を合成することができる。
光学材料用添加剤としては、単離された有機修飾微粒子をそのまま用いてもよく、単離された有機修飾微粒子に所定の添加剤を添加して用いてもよく、反応後に得られた混合物をそのまま用いてもよい。
(a)樹脂成分と、有機修飾微粒子ゾル液あるいは有機修飾微粒子粉末とをそれぞれ独立して作成し、その後に両者を混合する、あるいは混練する方法、
(b)予め作成した有機修飾微粒子が存在する条件で重合性化合物を重合し、重合体を生成する方法、
(c)予め作成した樹脂成分が存在する条件で有機修飾微粒子を作成する方法、
などの方法を採用することができる。
上記(a)の方法のうちでも、有機修飾微粒子ゾル液と、樹脂成分が溶解した溶液とを均一に混合し、溶媒を除去することで樹脂組成物を得る方法が好ましく挙げられる。
本発明に用いられる樹脂成分および重合体について述べる。なお、重合体は、樹脂組成物から得られる透明部材に含まれるものであるが、併せて以下に述べる。
特許文献2においては、樹脂成分100重量部に対し無機微粒子を80重量部程度含む樹脂組成物が記載されている。これに対し、本願発明に用いられる有機修飾微粒子は分散性に優れるため、樹脂組成物中に高濃度で含むことができ、樹脂成分(または重合性化合物)100重量部に対し100重量部以上の量であっても含有させることができる。
続いて、本発明の樹脂組成物から得られる、透明部材の製造方法について説明する。
樹脂成分と、有機修飾微粒子と、を含んでなる樹脂組成物を用いて透明部材を製造する方法としては、樹脂成分が溶解した溶液と、有機修飾微粒子とを均一に混合し、溶媒を除去することで薄膜を得る方法や、樹脂成分と有機修飾微粒子を溶融混錬し押し出し成形、または射出成形する方法等を挙げることができる。なお、有機修飾微粒子に代えて、有機修飾微粒子を含む添加剤を用いることもできる。
一方、重合性化合物と、有機修飾微粒子と、を含んでなる樹脂組成物(重合性組成物)は、硬化触媒の存在下、加熱下あるいは常温放置下あるいは冷却下で重合させて、透明部材を製造することができる。この場合、使用する硬化触媒の種類としては、アミン類、ホスフィン類、有機酸およびその塩、エステル、無水物類、無機酸、4級アンモニウム塩類、4級ホスホニウム塩類、3級スルホニウム塩類、2級ヨードニウム塩類、ルイス酸類、ラジカル重合触媒類、カチオン重合触媒類等が挙げられる。
トリメチルホスフィン、トリエチルホスフィン、トリn−プロピルホスフィン、トリイソプロピルホスフィン、トリn−ブチルホスフィン、トリフェニルホスフィン、トリベンジルホスフィン、1,2−ビス(ジフェニルホスフィノ)エタン、1,2−ビス(ジメチルホスフィノ)エタン等のホスフィン類、
トリフルオロ酢酸、トリクロロ酢酸、トリフルオロ酢酸無水物、トリフルオロ酢酸エチル、トリフルオロ酢酸ソーダ、トリハロゲノ酢酸及びそのエステル、無水物、塩、p−トルエンスルホン酸、メタンスルホン酸、トリフルオロメタンスルホン酸、トリフルオロメタンスルホン酸無水物、トリフルオロメタンスルホン酸エチル、トリフルオロメタンスルホン酸ソーダ等のトリハロゲノメタンスルホン酸及びそのエステル、無水物、塩、塩酸、硫酸、硝酸等の無機酸、
テトラメチルアンモニウムクロライド、テトラブチルアンモニウムクロライド、テトラブチルアンモニウムブロマイド等の4級アンモニウム塩、
テトラメチルホスホニウムクロライド、テトラブチルホスホニウムクロライド、テトラブチルホスホニウムブロマイド等の4級ホスホニウム塩、
トリメチルスルホニウムブロマイド、トリブチルスルホニウムブロマイド等の3級スルホニウム塩、ジフェニルヨードニウムブロマイド等の2級ヨードニウム塩、ジメチル錫ジクロライド、ジブチル錫ジクロライド、ジブチル錫ジラウレート、ジブチル錫ジアセテート、テトラクロロ錫、ジブチル錫オキサイド、ジアセトキシテトラブチルジスタノキサン等の有機錫化合物、塩化亜鉛、アセチルアセトン亜鉛、塩化アルミ、フッ化アルミ、トリフェニルアルミ、アセチルアセトンアルミ、イソプロポキシドアルミ、テトラクロロチタン及びその錯体、テトラヨードチタン、ジクロロチタニウムジイソプロポキシド、チタニウムイソプロポキシド等のチタン系アルコキシド、酢酸カルシウム、三フッ化硼素、三フッ化硼素ジエチルエーテル錯体、三フッ化硼素ピペリジン錯体、三フッ化硼素エチルアミン錯体、三フッ化硼素酢酸錯体、三フッ化硼素リン酸錯体、三フッ化硼素t−ブチルメチルエーテル錯体、三フッ化硼素ジブチルエーテル錯体、三フッ化硼素THF錯体、三フッ化硼素メチルスルフィド錯体、三フッ化硼素フェノール錯体等の三フッ化硼素の各種錯体及び三塩化硼素の各種錯体等のトリハロゲン化硼素化合物及びそのコンプレックスなどのルイス酸、
2,2'−アゾビス(2−シクロプロピルプロピオニトリル)、2,2'−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル)、2,2'−アゾビス(2,4−ジメチルバレロニトリル)、t−ブチルパーオキシ−2−エチルヘキサノエート、n−ブチル−4,4'−ビス(t−ブチルパーオキシ)バレレート、t−ブチルパーオキシベンゾエート等のラジカル重合触媒、
ジフェニルヨードニウムヘキサフルオロ燐酸、ジフェニルヨードニウムヘキサフルオロ砒酸、ジフェニルヨードニウムヘキサフルオロアンチモン、トリフェニルスルフォニウムテトラフルオロ硼酸、トリフェニルスルフォニウムヘキサフルオロ燐酸、トリフェニルスルフォニウムヘキサフルオロ砒酸等のカチオン重合触媒が挙げられるが、例示化合物のみに限定されるものではない。
テトラメチルアンモニウムクロライド、テトラブチルアンモニウムクロライド、テトラブチルアンモニウムブロマイド等の4級アンモニウム塩、テトラメチルホスホニウムクロライド、テトラブチルホスホニウムクロライド、テトラブチルホスホニウムブロマイド等の4級ホスホニウム塩ジメチル錫ジクロライド、ジブチル錫ジクロライド、ジブチル錫ジラウレート、ジブチル錫ジアセテート、テトラクロロ錫、ジブチル錫オキサイド、ジアセトキシテトラブチルジスタノキサン等の有機錫化合物の化合物群から選ばれる1種以上の化合物であり、2種以上の化合物を選択すると、得られる樹脂の光学物性、色相、透明性、光学ひずみ(脈離)、歩留まりの観点でより好ましい。
また、透明部材は、重合体または樹脂成分100重量部に対し、金属成分を1重量部以上300重量部以下の量で含む。なお、金属成分は、有機修飾微粒子由来のものである。
本発明の透明部材は、上記の量で有機修飾微粒子を含むので、透明性にも優れ、さらに高屈折率を有するとともに高強度である。
本発明の樹脂組成物は、注型重合時の成型モールドを変えることにより種々の形態の成形体(透明部材)を得ることができ、眼鏡レンズ、カメラレンズ、発光ダイオード(LED)等の高屈折率や透明性の特徴を生かした光学材料としての各種の用途に使用することができる。特に、眼鏡レンズ、カメラレンズ等の用途として好適である。
・ 屈折率(ne): プルフリッヒ屈折計を用いて、20℃でe線(546nm)における屈折率を測定した。
・ 樹脂透明性: 目視で観察した。
(超臨界水を利用した有機修飾微粒子の合成)
20ccの反応管(SUS316,1/2インチ)に、0.01Mol/lのZn(NO3)2を8.5gと、ヘキサン酸0.5gを入れて封管し、400℃のサンドバスに反応管を入れて加熱させた。2分間で400℃まで昇温した。そのまま10分間反応させた後、反応管を冷水に入れて冷却した。反応液を蒸留水にあけ、遠心分離とデカンテーションを数回繰り返し行った。さらにエタノールで遠心分離とデカンテーションを行った後、減圧乾燥することで、表面が有機修飾された酸化亜鉛微粒子を得た。
ビス(2,3-エピチオプロピル)スルフィド0.95gにビス(メルカプトエチル)スルフィド0.05g、触媒としてN,N−ジメチルシクロヘキシルアミン2mg、および上記方法により合成した表面有機修飾微粒子1.5gを加えて良く混合した。これを0.6kPaで0.5時間脱気した後、レンズモールドに注入し、30℃から徐々に昇温して120℃まで加熱し、24時間かけて重合硬化させた。冷却した後にガラスモールドを離型させレンズを取り出した。得られたレンズの性能試験の結果を表1に示す。
「0.01Mol/lのZn(NO3)2 8.5g」に代えて、「0.01Mol/lのZr(NO3)2を8g」を使用し、ヘキサン酸0.5gに代えてデカン酸1gを使用した以外は、実施例1と同様の操作を行った。性能試験の結果を表1に示す。
「0.01Mol/lのZn(NO3)2 8.5g」に代えて「0.01Mol/lのTi(SO4)2 8g」を使用し、「ヘキサン酸0.5g」に代えて「デカン酸1g」を使用した以外は、実施例1と同様の操作を行った。性能試験の結果を表1に示す。
「0.01Mol/lのZn(NO3)2 8.5g」に代えて「0.01Mol/lのTi(SO4)2 8.5g」を使用し、「ヘキサン酸0.5g」に代えて「ヘキサンチオール0.5g」を使用した以外は、実施例1と同様の操作を行った。性能試験の結果を表1に示す。
「0.01Mol/lのZn(NO3)2 8.5g」に代えて「0.01Mol/lのTi(SO4)2 8.5g」を使用し、「ヘキサン酸0.5g」に代えて「ヘキサノール0.5g」を使用した以外は、実施例1と同様の操作を行った。性能試験の結果を表1に示す。
「0.01Mol/lのZn(NO3)2 8.5g」に代えて「0.01Mol/lのTi(SO4)2 8.5g」を使用し、「ヘキサン酸0.5g」に代えて「ヘキシルアミン0.5g」を使用した以外は、実施例1と同様の操作を行った。性能試験の結果を表1に示す。
「0.01Mol/lのZn(NO3)2 8.5g」に代えて、「0.01Mol/lのTi(SO4)2 8g」と「0.01Mol/lのSnCl4 0.5g」とを使用した以外は、実施例1と同様の操作を行った。性能試験の結果を表1に示す。
(超臨界水を利用した酸化チタンの合成)
20ccの反応管(SUS316,1/2インチ)に0.1Mol/lのTiCl4を9g仕込み封管し、400℃のサンドバスに反応管を入れて加熱させた。400℃まで昇温するのに、2分間かかった。そのまま10分間反応させた後、反応管を冷水に入れて冷却した。反応液を蒸留水にあけ、遠心分離とデカンテーションを数回繰り返し行った。さらにエタノールで遠心分離とデカンテーションを行った後、減圧乾燥することで、表面を修飾していない酸化チタン微粒子を得た。
有機修飾微粒子を混合せず、重合性化合物のみで重合させた以外は実施例1と同様の操作を行った。結果を表1に示す。
[比較例2]
有機修飾微粒子に代えて、製造例1で調製した酸化チタン微粒子を用いた以外は、実施例1と同様の操作を行った。結果を表1に示す。
[比較例3]
製造例1において、エタノールの代わりにメタノールで遠心分離とデカンテーションを行った後、20重量%メタノール分散ゾル液とした。このゾル液10gに硫酸を加えてpHを5にした後、3−アミノプロピルトリメトキシシラン0.1gを加えて50℃で加熱した。ロータリーエバポレーターによりメタノールを加えて濃縮する操作を繰り返した後、得られたメタノール分散ゾル液を減圧乾燥し、白色粉末を得た。
得られた表面修飾微粒子を用いて、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
(ルチル型酸化チタンの合成)
イオン交換水50mlに、酸化塩化チタンの塩酸水溶液(Ti 15重量%含有)5mlを加えた。溶液のpHは−0.1であった。マグネチックスターラーで攪拌し、50℃で1時間加熱したところ、白色の沈殿を得た。得られた白色沈殿はイオン交換水に再分散しなかった。この固形分の粉末X線回折測定、電子顕微鏡観察を行った。電子顕微鏡観察は透過型電子顕微鏡を用い、メッシュに希薄ゾル液を滴下したものを倍率20万倍、200万倍で観察した。その結果、凝集粒子径200nm以上のルチル型酸化チタンであった。
(スズ修飾ルチル型酸化チタン超微粒子ゾル液の調製)
四塩化スズ五水和物0.27gを100mlナス型フラスコに仕込み、イオン交換水50mlに溶解し、酸化塩化チタンの塩酸水溶液(Ti 15重量%含有)5mlを加えた。溶液のpHは−0.1であった。(仕込みTi濃度=0.45、Sn/Ti=0.03)マグネチックスターラーで攪拌し、50℃で1時間加熱したところ、白色の沈殿を得た。遠心分離を行い、白色沈殿を回収、イオン交換水に再分散させた。限外ろ過を行い、固形分2重量%のゾル液を得た。この固形分の粉末X線回折測定、電子顕微鏡観察を行った。120℃で2時間熱風乾燥を行った後に粉末X線回折測定を行ったところ、酸化チタンルチル型であった。結晶径は回折ピークの半値幅からDebye−Sherrerの式を用いて計算した。その結果、結晶径が平均それぞれ短軸5nm、長軸8nmであった。電子顕微鏡観察は製造例2と同じ方法で観察した。その結果、平均凝集粒子径が23nmのルチル型酸化チタンであった。誘導結合プラズマ法分析によるSn/Tiの元素モル比は0.02であった。
(二層ケイ素酸化物被覆スズ修飾ルチル型酸化チタン超微粒子ゾル液の調製)
製造例3で得られたスズ修飾ルチル型酸化チタン超微粒子ゾル液2500gをpH=3に調整した後、80℃に加熱した。2重量%のケイ素酸化物水溶液125gを1時間かけて滴下し、さらに30分加熱した。室温にまで冷却した後、1mol/l水酸化ナトリウム水溶液を加えてゾル液にした。80℃に昇温し、pH=9に維持しながら、2重量%ケイ素酸化物水溶液625gを2時間かけて滴下しさらに4時間加熱した。限外ろ過を行い精製し、2重量%ゾル液を得た。誘導結合プラズマ法分析による被覆層/微粒子の重量比は0.13/1であった。ロータリーエバポレーターによりメタノールを加えて濃縮する操作を繰り返した後、20重量%メタノール分散ゾル液とした。
製造例3で四塩化スズ五水和物を0.9g用いた以外は製造例3および4と同様に実施した。(仕込みTi濃度=0.45、Sn/Ti=0.1)得られたゾル液の固形分を製造例3と同様に分析したところSn/Tiの元素モル比は0.06であった。結晶径が平均それぞれ短軸5nm、長軸8nmで、平均凝集粒子径が20nmのルチル型酸化チタンであった。被覆層/微粒子の重量比は0.13/1であった。ロータリーエバポレーターによりメタノールを加えて濃縮する操作を繰り返した後、20重量%メタノール分散ゾル液とした。
20ccの反応管(SUS316,1/2インチ)に、製造例2で合成した酸化チタン微粒子(固形分換算0.1g)と、有機修飾分子(デカン酸1g)を入れ、全重量が9gになるように蒸留水を加えて封管し、400℃のサンドバスに反応管を入れて加熱させた。2分間で400℃まで昇温した。そのまま10分間反応させた後、反応管を冷水に入れて冷却した。反応液を蒸留水にあけ、遠心分離とデカンテーションを数回繰り返し行った。さらにエタノールで遠心分離とデカンテーションを行った後、減圧乾燥することで、表面が有機修飾された酸化チタン微粒子を得た。
得られた表面処理酸化チタン微粒子を用いて、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
製造例2で合成した酸化チタン微粒子(固形分換算0.1g)を製造例3で合成したスズ修飾酸化チタン微粒子(固形分換算0.1g)に代え、デカン酸1gをオレイン酸2gに代えた以外は、実施例8と同様の操作を行い、表面が有機修飾されたスズ含有酸化チタン微粒子を得た。
得られた表面処理スズ含有酸化チタン微粒子を用いて、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
製造例2で合成した酸化チタン微粒子(固形分換算0.1g)を製造例4で合成したスズ修飾酸化チタン微粒子(固形分換算0.1g)に代え、「デカン酸 1g」を「ヘキサン酸 1g」に代えた以外は、実施例8と同様の操作を行い、表面が有機修飾されたスズ修飾酸化チタン微粒子を得た。
得られた表面処理スズ修飾酸化チタン微粒子を用いて、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
製造例2で合成した酸化チタン微粒子(固形分換算0.1g)を製造例5で合成したスズ修飾酸化チタン微粒子(固形分換算0.1g)に代え、「デカン酸 1g」を「ヘキサン酸 1g」に代えた以外は、実施例8と同様の操作を行い、表面が有機修飾されたスズ修飾酸化チタン微粒子を得た。
得られた表面処理スズ修飾酸化チタン微粒子を用いて、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
有機修飾された酸化亜鉛微粒子を、製造例2で得られた未修飾の微粒子に代えた以外は、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
製造例3で得られた固形分2重量%ゾル液を、製造例4と同様の方法で20重量%メタノール分散ゾル液とした後、減圧乾燥することで、白色粉末を得た。有機修飾された酸化亜鉛微粒子を、この未修飾の微粒子に代えた以外は、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
製造例2で得られた未修飾の微粒子2gを、メタノールに分散させ、2重量%メタノール分散ゾル液100gを調製した。このゾル液に硫酸を加えてpHを5にした後、3−アミノプロピルトリメトキシシラン1gを加えて50℃で加熱した。ロータリーエバポレーターによりメタノールを加えて濃縮する操作を繰り返した後、得られたメタノール分散ゾル液を減圧乾燥し、白色粉末を得た。
有機修飾された酸化亜鉛微粒子を、得られた表面修飾微粒子に代えた以外は、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
製造例3で得られた固形分2重量%ゾル液を、製造例4と同様の方法で20重量%メタノール分散ゾル液とした。このゾル液100gに硫酸を加えてpHを5にした後、3−アミノプロピルトリメトキシシラン1gを加えて50℃で加熱した。ロータリーエバポレーターによりメタノールを加えて濃縮する操作を繰り返した後、得られたメタノール分散ゾル液を減圧乾燥し、白色粉末を得た。
有機修飾された酸化亜鉛微粒子を、得られた表面修飾微粒子に代えた以外は、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
ジメチルホルムアミド200mLに酢酸亜鉛二水和物2.5gとヘキサンチオール2.7gを溶解させ、3つ口フラスコに入れて反応系内を窒素置換した。2M水酸化ナトリウム水溶液を加えて溶液のpHを8に調節し、室温で攪拌しながら滴下漏斗から硫化ナトリウム九水和物2.7gを溶かした水溶液50mLを30分かけて滴下した。室温で10時間攪拌後、反応液をアセトンに注いで沈殿を析出させ、遠心分離によりヘキサンチオールで表面修飾された硫化亜鉛微粒子を得た。
有機修飾された酸化亜鉛微粒子を、得られた表面修飾微粒子に代えた以外は、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
20ccの反応管(SUS316,1/2インチ)に、比較例8で得られた表面修飾硫化亜鉛微粒子0.1gと、ヘキサンチオール0.5gを入れ、全重量が9gになるように蒸留水を加えて封管し、400℃のサンドバスに反応管を入れて加熱させた。2分間で400℃まで昇温した。そのまま10分間反応させた後、反応管を冷水に入れて冷却した。反応液を蒸留水にあけ、遠心分離とデカンテーションを数回繰り返し行った。さらにエタノールで遠心分離とデカンテーションを行った後、減圧乾燥することで、高温高圧水条件下で修飾された硫化亜鉛微粒子を得た。
有機修飾された酸化亜鉛微粒子を、得られた表面修飾微粒子に代えた以外は、実施例1と同様の方法でレンズを作製し、性能を評価した。結果を表1に示す。
(表面修飾微粒子含有エピスルフィド樹脂の作製)
「0.01Mol/lのZn(NO3)2 8.5g」を「0.01Mol/lのTi(SO4)2 8.5g」に代えた以外は、実施例1と同様の操作を行った。得られたレンズの性能試験の結果を表2に示す。
(表面修飾微粒子含有チオウレタン樹脂の作製)
実施例13と同様の方法で合成した、表面修飾酸化チタン微粒子を用いた。
キシリレンジイソシアナート0.507gに触媒としてジブチルチンジクロライド0.1mg、内部離型剤として「ZelecUN」(商品名、stepan社製 酸性リン酸アルキルエステル)1mg、紫外線吸収剤として「バイオソーブ583」(商品名、共同薬品社製)0.5mgをあらかじめ溶解して混合液としておいた。次いで、4,8−ジメルカプトメチル−1,11−メルカプト−3,6,9−トリチアウンデカン0.493g、および上記の表面修飾酸化チタン微粒子1.5gを加え、良く混合し、モノマー混合物とした。このモノマー混合物を0.6kPaで1時間脱気した後、レンズモールドに注入し、40℃から徐々に昇温して130℃まで加熱し、20時間かけて硬化させた。冷却した後にガラスモールドを離型させレンズを取り出した。得られたレンズの性能試験の結果を表2にまとめた。
(表面修飾微粒子含有エピスルフィド/チオウレタン共重合樹脂の作製)
実施例13と同様の方法で合成した、表面修飾酸化チタン微粒子を用いた。
20℃の室温下で、ビス(2,3−エピチオプロピル)スルフィド0.75gとビス(2−メルカプトエチル)スルフィド0.12g、ペンタエリスリトールテトラキス(2−メルカプトアセテート)0.03g、テトラn−ブチルホスホニウムブロマイド0.7mgを混合し、透明になるまで撹拌し溶解させた。これとは別にm−キシリレンジイソシアナート0.1gとジブチルチンジクロライド0.1mg、「ZelecUN」(商品名、stepan社製 酸性リン酸アルキルエステル)0.2mgを混合し、透明になるまで攪拌し溶解させた。できあがった2種類の溶液を混合し、さらに上記の表面有機修飾微粒子1.5gを混合した後、減圧下0.5時間脱泡した。得られた混合液をレンズ用モールド型に注入し、30℃から120℃まで徐々に昇温し、24時間で重合を行った。重合終了後、得られたレンズをモールドから離型させ、120℃にて2時間アニールを行った。得られたレンズの性能試験の結果を表2にまとめた。
有機修飾微粒子を、ビス(2,3-エピチオプロピル)スルフィドとビス(メルカプトエチル)スルフィドとの合計量100重量部に対し表3に記載の量比となるように添加した以外は、実施例13と同様の操作を行った。得られたレンズの性能試験の結果を表3に示す。
「0.01Mol/lのZn(NO3)2 8.5g」に代えて「0.01Mol/lのTi(SO4)2 8.5g」を使用し、また「ヘキサン酸0.5g」を「デカン酸1g」に代えた以外は実施例1と同様に有機修飾微粒子の合成を行った。得られた有機修飾微粒子を用いてレンズモノマー混合液を調製するに際し、キシリレンジイソシアナートと4,8−ジメルカプトメチル−1,11−メルカプト−3,6,9−トリチアウンデカンとの合計量100重量部に対し有機修飾微粒子を表3に記載の量比となるように添加した以外は、実施例14と同様の操作で行った。性能試験の結果を表3に示す。
Claims (9)
- エピスルフィド基を有する重合性化合物およびポリチオール化合物とイソ(チオ)シアネート化合物類とからなる重合性化合物から選択される1種または2種以上の重合性化合物(a)と、
金属塩および有機物を含む溶液を、200℃以上500℃以下の温度、5MPa以上50MPa以下の圧力で加熱加圧して、水を超臨界または亜臨界状態とすることにより生成された、金属微粒子の表面に有機物が結合している有機修飾微粒子(b)と、を含んでなる重合性組成物であって、
前記金属塩は、塩化チタン、塩化スズ、水酸化バリウム、水酸化アルミニウム、硝酸亜鉛、硝酸セリウム、硫酸チタン、塩化酸化ジルコニウムおよび硝酸ジルコニウムから選択される少なくとも一種であり、
前記有機物は、ヘキサン酸、デカン酸、ヘキサンチオール、ヘキサノール、ヘキシルアミンおよびオレイン酸から選択される少なくとも一種であり、
前記重合性組成物から得られる成形体のe線の屈折率が、1.71以上である、ことを特徴とする重合性組成物。 - 前記有機修飾微粒子(b)の平均粒子径が1nm以上100nm以下であることを特徴とする請求項1に記載の重合性組成物。
- 前記重合性化合物(a)100重量部に対し、前記有機修飾微粒子(b)を1重量部以上300重量部以下含むことを特徴とする請求項1乃至2のいずれかに記載の重合性組成物。
- 前記金属微粒子は、その表面に無機物からなる1層以上の被覆層を備え、前記有機物は前記被覆層の表面に結合していることを特徴とする請求項1乃至3のいずれかに記載の重合性組成物。
- 前記重合性化合物(a)を重合してなる重合体と、前記有機修飾微粒子(b)とを含む、請求項1乃至4のいずれかに記載の重合性組成物から得られることを特徴とする透明部材。
- 前記重合体は、チオウレタン樹脂およびエピスルフィド樹脂よりなる群から選択される1種または2種以上である請求項5に記載の透明部材。
- 前記重合体100重量部に対し、金属成分を1重量部以上300重量部以下含むことを特徴とする請求項5または6に記載の透明部材。
- 請求項5乃至7のいずれかに記載の透明部材からなることを特徴とする光学部品。
- 請求項5乃至7のいずれかに記載の透明部材からなることを特徴とする光学レンズ。
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PCT/JP2008/003514 WO2009078129A1 (ja) | 2007-12-17 | 2008-11-28 | 樹脂組成物、該樹脂組成物から得られる透明部材およびその用途 |
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JP (1) | JP5422393B2 (ja) |
KR (1) | KR101190958B1 (ja) |
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Also Published As
Publication number | Publication date |
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US8648130B2 (en) | 2014-02-11 |
WO2009078129A1 (ja) | 2009-06-25 |
EP2223969A4 (en) | 2013-03-27 |
KR101190958B1 (ko) | 2012-10-15 |
JPWO2009078129A1 (ja) | 2011-04-28 |
KR20100085152A (ko) | 2010-07-28 |
EP2223969B1 (en) | 2015-02-25 |
US20100256271A1 (en) | 2010-10-07 |
CN101883825A (zh) | 2010-11-10 |
EP2223969A1 (en) | 2010-09-01 |
CN101883825B (zh) | 2013-11-06 |
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