JP4266748B2 - 新規なポリイソシアネート化合物、その製造方法及び用途 - Google Patents
新規なポリイソシアネート化合物、その製造方法及び用途 Download PDFInfo
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- JP4266748B2 JP4266748B2 JP2003302244A JP2003302244A JP4266748B2 JP 4266748 B2 JP4266748 B2 JP 4266748B2 JP 2003302244 A JP2003302244 A JP 2003302244A JP 2003302244 A JP2003302244 A JP 2003302244A JP 4266748 B2 JP4266748 B2 JP 4266748B2
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- bicyclo
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/10—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of rings other than six-membered aromatic rings
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- G—PHYSICS
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- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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- G—PHYSICS
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- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
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Description
1. 一般式(1)
2.一般式(1)で表される化合物が、ビシクロ[2.2.1]ヘプタン−2,5−ジイソシアネート又はビシクロ[2.2.1]ヘプタン−2,6−ジイソシアネート若しくはこれらの混合物である前記1記載の化合物。
3.一般式(2)
4.前記(1)記載の脂環族ポリイソシアネート化合物を含有する重合性組成物、
5.前記(4)に記載の重合性組成物を重合して得られる樹脂、
6.前記(5)記載の樹脂からなる光学材料、
7.前記(6)に記載の光学材料からなるレンズ
である。
より高い耐熱性を有する樹脂を提供することができる。
屈折率、アッベ数:プリフリッヒ屈折計を用い、20℃で測定した。
耐候性:サンシャインカーボンアークランプを装備したウェザーオメータにレンズ用樹脂をセットし、20時間経たところでレンズを取り出し試験前のレンズ用樹脂の色相を比較した。
評価基準は、変化なし(○)、わずかに黄変(△)、黄変(×)とした。
外 観:目視により観察した。
耐熱性:サーモメカニカルアナライザー〔リガク社、TAS300〕を用いたペネトレーション法によりピン先0.5mmΦで50g荷重、10℃/minの加熱をして熱変形開始温度を測定した。
攪拌機、温度計等を備えた500mLのガラス製丸底フラスコに、ビシクロ[2.2.1]ヘプタン−2,5(6)−ジカルボニトリル(三井化学株式会社製)を73.0g(0.5mol)、90%硫酸を500g仕込み、40℃で2時間攪拌を行った。
反応終了後、反応液を室温まで冷却した後、2Lの氷水にゆっくりと注いだ。この溶液を十分冷却しながら、30%水酸化ナトリウム水溶液で中和すると白色の固形物が析出した。析出した固形物を、ろ紙を使用した吸引ろ過により分別し、水で洗浄した後、乾燥した(48.3g)。この固形物のマススペクトルによる分析を行った結果、ビシクロ[2.2.1]ヘプタン−2,5(6)−ジカルボアミドであった(EI m/z 182(M+))。ガスクロマトグラフィー法による分析の結果、純度は99%であった(ビシクロ[2.2.1]ヘプタン−2,5(6)−ジカルボニトリルに対する収率53%)。
攪拌機、温度計、冷却器等を備えた2Lガラス製丸底セパラブルフラスコに、ビシクロ[2.2.1]ヘプタン−2,5(6)−ジカルボアミドを91.1g(0.50mol)、10%水酸化ナトリウム水溶液1000g(2.50mol)を仕込み、10〜15℃に冷却した。次いで、攪拌下に、5%次亜塩素酸ナトリウム水溶液780g(1.10mol)をこの懸濁液に、温度が15℃を越えないように30分間に亘って滴下した。滴下終了後、3時間に亘って温度を10〜15℃に保った後、室温へと昇温した。10時間攪拌した後、70〜80℃に昇温して、さらに2時間攪拌した。
ビシクロ[2.2.1]ヘプタン−2、5(6)―ジアミンを原料として冷熱2段ホスゲン化法で行った。電磁誘導攪拌機、自動圧力調整弁、温度計、窒素導入ライン、ホスゲン導入ライン、凝縮器、原料フィードポンプを、備え付けたジャケット付き10L加圧反応器にオルトジクロルベンゼン2500gを仕込む。次いでホスゲン1425g(14.2mol)をホスゲン導入ラインより加え攪拌を開始する。反応器のジャケットには冷水を通し、内温を約5℃に保った。そこへ上記ジアミン302.9g(2.4mol)をオルトジクロルベンゼン2500gに溶解した溶液をフィードポンプにて60分かけてフィードし5〜10℃、常圧下で冷ホスゲン化を行った。フィード終了後、フラスコ内は淡褐白色スラリー状液となった。
実施例1で合成した、ビシクロ[2.2.1]ヘプタン−2,5(6)−ジイソシアネート17.8g(0.1mol)と、1,2−ビス[(2−メルカプトエチル)チオ]―3―メルカプトプロパン17.2g(0.066mol)、を混合し均一液とした後、ガラスモールドとガスケットより成るレンズモールド型に注入し、ついで加熱して重合させた。こうして得られた樹脂は、無色透明で耐衝撃性に優れ、屈折率[ne]=1.636、アッベ数[νe]=36.9、熱変形開始温度は167℃であった。このデータを表1に示す。
実施例1のジイソシアネート化合物を1,3−ビスイソシアナトメチルシクロヘキサン18.8g(0.1mol)とした他は、実施例1と同様に行った。得られた樹脂の光学物性データを表1に示す。
比較例1のジイソシアネート化合物をビスイソシアナトメチルノルボルナン20.7g(0.1mol)とした他は比較例1と同様に行った。得られた樹脂の光学物性データを表1に示す
Claims (8)
- 一般式(1)で表される化合物が、ビシクロ[2.2.1]ヘプタン−2,5−ジイソシアネート又はビシクロ[2.2.1]ヘプタン−2,6−ジイソシアネート若しくはこれらの混合物である請求項1に記載の化合物。
- 請求項1又は2記載の一般式(1)で表される化合物を含有する重合性組成物。
- ポリオール、ポリチオール、ヒドロキシ基を有するメルカプト化合物から選ばれた少なくとも1種の活性水素化合物を含有する請求項4に記載の重合性組成物。
- 請求項4又は5に記載の重合性組成物を重合して得られる樹脂。
- 請求項6に記載の樹脂からなる光学材料。
- 請求項7に記載の光学材料からなるレンズ。
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JP2003302244A JP4266748B2 (ja) | 2003-08-27 | 2003-08-27 | 新規なポリイソシアネート化合物、その製造方法及び用途 |
US10/921,890 US7132495B2 (en) | 2003-08-27 | 2004-08-20 | Polyisocyanate compound, method for producing the same, and uses thereof |
KR1020040066458A KR100683458B1 (ko) | 2003-08-27 | 2004-08-23 | 신규 폴리이소시아네이트 화합물, 그 제조방법 및 용도 |
CNB2004100572346A CN1310879C (zh) | 2003-08-27 | 2004-08-23 | 新的多异氰酸酯化合物、其制造方法及用途 |
FR0409101A FR2859207B1 (fr) | 2003-08-27 | 2004-08-26 | Polyisocyanate, procede et compose de depart de preparation de ce polyisocyanate, et utilisations de ce polyisocyanate |
DE102004041344A DE102004041344A1 (de) | 2003-08-27 | 2004-08-26 | Neuartige Polyisocyanatverbindung, Verfahren zur Herstellung derselben und Verwendungen davon |
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US8829088B1 (en) * | 2013-04-29 | 2014-09-09 | Xerox Corporation | Fuser member compositions |
CN111655750A (zh) * | 2018-01-25 | 2020-09-11 | 汉高股份有限及两合公司 | 基于硫代氨基甲酸酯的气凝胶 |
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GB876013A (en) * | 1959-03-16 | 1961-08-30 | Union Carbide Corp | Improvements in and relating to substituted tricyclodecanes |
US3173950A (en) * | 1962-08-14 | 1965-03-16 | Hercules Powder Co Ltd | Preparation of alicyclic amines |
GB1026506A (en) | 1962-10-17 | 1966-04-20 | Du Pont | Bicyclodiamines and preparation thereof |
US3173590A (en) | 1963-03-29 | 1965-03-16 | Georgia Pacific Corp | Dispenser for rolled material |
US3317387A (en) * | 1964-05-25 | 1967-05-02 | Du Pont | Method of reducing the severity of influenza virus infections |
US3470248A (en) * | 1965-10-19 | 1969-09-30 | Union Carbide Corp | Tricyclic polyamines |
JP2621921B2 (ja) | 1988-05-10 | 1997-06-18 | 旭化成工業株式会社 | フイルムの製造方法 |
JP2764081B2 (ja) | 1990-01-23 | 1998-06-11 | 三井化学株式会社 | 脂環式―脂肪族ジイソシアナートの製造方法 |
JP2840123B2 (ja) * | 1990-08-23 | 1998-12-24 | 三井化学株式会社 | 変性ビニルエステル樹脂組成物 |
JP3930124B2 (ja) | 1997-11-07 | 2007-06-13 | 三井化学株式会社 | ポリイソシアネート及びその製造法 |
US6207364B1 (en) * | 1998-04-21 | 2001-03-27 | Konica Corporation | Thermally developable material |
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KR100683458B1 (ko) | 2007-02-20 |
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JP2005068097A (ja) | 2005-03-17 |
US7132495B2 (en) | 2006-11-07 |
DE102004041344A1 (de) | 2005-03-24 |
CN1611488A (zh) | 2005-05-04 |
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