JP2016190850A - ポリオルガノシロキサン化合物、製造方法およびこれを含むコーポリカーボネート樹脂 - Google Patents
ポリオルガノシロキサン化合物、製造方法およびこれを含むコーポリカーボネート樹脂 Download PDFInfo
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- JP2016190850A JP2016190850A JP2016093086A JP2016093086A JP2016190850A JP 2016190850 A JP2016190850 A JP 2016190850A JP 2016093086 A JP2016093086 A JP 2016093086A JP 2016093086 A JP2016093086 A JP 2016093086A JP 2016190850 A JP2016190850 A JP 2016190850A
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- compound
- polyorganosiloxane
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- weight
- chemical formula
- Prior art date
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- -1 polysiloxane Polymers 0.000 claims abstract description 48
- 239000000126 substance Substances 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
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- 125000003342 alkenyl group Chemical group 0.000 claims 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AZSKHRTUXHLAHS-UHFFFAOYSA-N tris(2,4-di-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C AZSKHRTUXHLAHS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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Abstract
Description
技術的課題
前記のような従来の技術の問題点を解決するために、本発明は、多様な用途に適用可能であり、特にコーポリカーボネート樹脂の衝撃補強剤、改質剤または共単量体として使用可能なポリオルガノシロキサン化合物およびこれを含んで透明性を維持しながら低温衝撃性を向上させたコーポリカーボネート樹脂を提供することを目的とする。
前記の目的を達成するために、本発明は、下記の化学式1
前記ヒドロキシ安息香酸に炭素数2乃至8のアルケニルアルコールをエステル化反応させてアルケニルヒドロキシベンゾエートを製造する段階;および前記アルケニルヒドロキシベンゾエートに、ポリオルガノシロキサンであって両側末端基が水素である化合物(以下、H−PDMSという)をヒドロシリル化反応させて下記の化学式1
前記炭素数2乃至8のアルケニルアルコールをH−PDMSに反応させてOH−PDMSを収得する段階;および
前記OH−PDMSに前記ヒドロキシ安息香酸を投入し、酸触媒下にエステル化反応させて、前記化学式1で示されるポリオルガノシロキサン化合物を製造する段階;を含むことを特徴とするポリオルガノシロキサン化合物の製造方法を提供する。
出発物質としてヒドロキシ安息香酸に炭素数2乃至8のアルケニルアルコールをエステル化反応させてアルケニルヒドロキシベンゾエートを製造する段階;および前記アルケニルヒドロキシベンゾエートにポリオルガノシロキサンであって両側末端基が水素である化合物(H−PDMS)をヒドロシリル化反応させて前記化学式1で示されるポリオルガノシロキサン化合物を製造する段階;を含むことを特徴とする。
出発物質としてH−PDMSに炭素数2乃至8のアルケニルアルコールを反応させてOH−PDMSを収得する段階;および
前記OH−PDMSにヒドロキシ安息香酸を投入し酸触媒下にエステル化反応させて、前記化学式1で示されるポリオルガノシロキサン化合物を製造する段階;を含むものであり得る。
前記ヒドロシリル化反応物にヒドロキシ安息香酸を投入しエステル反応させて前記化学式1で示されるポリオルガノシロキサン化合物を収得することができる。
前記コーポリカーボネート樹脂は、一例として、前記芳香族ジオール化合物、カーボネート前駆体、および前記化学式1で示されるポリオルガノシロキサン化合物総100重量%に対して前記芳香族ジオール化合物25乃至85重量%、前記化学式1で示されるポリオルガノシロキサン化合物1乃至60重量%、および前記カーボネート前駆体10乃至70重量%で重合されたもので、この範囲内で低温衝撃強度が維持されながら分子量対比透明性に優れる効果がある。
<実施例1>
<下記反応式2の中の4の化合物製造>
オクタメチルシクロテトラシロキサン47.60g(160mmol)、テトラメチルジシロキサン2.40g(17.8mmol)を混合した後、この混合物をオクタメチルシクロテトラシロキサン100重量部対比酸性白土(DC−A3)1重量部と共に3Lフラスコ(flask)に入れ、60℃で4時間反応させた。反応終了後、これをエチルアセテートで希釈し、セライト(celite)を用いて急速にフィルタリングした。このように得られた未変性ポリオルガノシロキサンの反復単位(p)は1H NMRで確認した結果、55であった。
<下記反応式4の中の4の化合物製造>
前記実施例1の<化学式1のポリオルガノシロキサン化合物製造>で用いた反応式2の中の4の化合物として収得したメタリルヒドロキシベンゾエート(methallyl hydroxybenzoate)6.9g(36mmol)の代わりに、2−アリルフェノール(2−allylphenol)4.81gを使用したことを除いては、実施例1と同一な実験を繰り返し、反応式2の中の3で示される化合物の代わりにアリルフェノールに両側末端が変性された下記の化学式5で示され、PDMS内繰り返し単位(n)が40であるシロキサン化合物(AP−PDMS)を収得した。
前記実施例1の<化学式1のポリオルガノシロキサン化合物製造>で用いた反応式2の中の4の化合物として収得したメタリルヒドロキシベンゾエート(methallyl hydroxybenzoate)6.9g(36mmol)の代わりに、オイゲノール(eugenol)4.87gを使用したことを除いては、実施例1と同一な実験を繰り返し、反応式2の中の3で示される化合物の代わりにオイゲノール(eugenol)に両側末端が変性された下記の化学式6で示され、PDMS内繰り返し単位(n)が43であるシロキサン化合物(EG−PDMS)を収得した。
<コーポリカーボネート樹脂の製造>
前記実施例1乃至2および比較例1乃至2のシロキサン化合物を含むコーポリカーボネート樹脂および射出試片をそれぞれ次の通り製造した。
製造されたコーポリカーボネート樹脂にトリス(2,4−ジ−tert−ブチルフェニル)ホスファート0.050重量部を添加し、HAAKE Mini CTW二軸押出機を用いてペレット化した後、HAAKE Minijet射出成形機を用いてシリンダー温度320℃、金型温度90℃で射出成形して試片を製造した。
製造されたコーポリカーボネート樹脂の射出試片の特性を下記の方法で測定し、その結果を下記の表1に共に示した。
Claims (8)
- 前記R6は、水素であることを特徴とする請求項1に記載の化合物。
- 前記R5およびR’5が水素であり、R7は−OHであることを特徴とする請求項1に記載の化合物。
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CN107266318B (zh) | 2020-07-03 |
CN107266318A (zh) | 2017-10-20 |
EP3018165B1 (en) | 2019-06-12 |
US9452969B2 (en) | 2016-09-27 |
JP2016528327A (ja) | 2016-09-15 |
JP6150945B2 (ja) | 2017-06-21 |
CN104837895B (zh) | 2017-06-06 |
WO2015002427A1 (ko) | 2015-01-08 |
PL3018165T3 (pl) | 2019-11-29 |
US20150315380A1 (en) | 2015-11-05 |
EP3018165A4 (en) | 2016-06-22 |
US9267034B2 (en) | 2016-02-23 |
CN104837895A (zh) | 2015-08-12 |
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US20160145187A1 (en) | 2016-05-26 |
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