JPH0788346B2 - Fluorine-containing alkoxyphthalonitrile - Google Patents
Fluorine-containing alkoxyphthalonitrileInfo
- Publication number
- JPH0788346B2 JPH0788346B2 JP62147840A JP14784087A JPH0788346B2 JP H0788346 B2 JPH0788346 B2 JP H0788346B2 JP 62147840 A JP62147840 A JP 62147840A JP 14784087 A JP14784087 A JP 14784087A JP H0788346 B2 JPH0788346 B2 JP H0788346B2
- Authority
- JP
- Japan
- Prior art keywords
- phthalonitrile
- fluorine
- phthalocyanine
- compound
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0675—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/248—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes porphines; azaporphines, e.g. phthalocyanines
Description
【発明の詳細な説明】 Ｉ 発明の背景 （技術分野） 本発明は、新規な含フッ素アルコキシフタロニトリル化
合物に関する。本発明のフタロニトリル化合物は、それ
自体又は加水分解等により容易に得られるジカルボン酸
及びその誘導体（アミド、イミド、酸無水物）としてフ
タロシアニン等の原料として有用である。TECHNICAL FIELD The present invention relates to a novel fluorine-containing alkoxyphthalonitrile compound. INDUSTRIAL APPLICABILITY The phthalonitrile compound of the present invention is useful as a raw material for phthalocyanine and the like as a dicarboxylic acid and its derivative (amide, imide, acid anhydride) which can be easily obtained by itself or by hydrolysis.
（先行技術とその問題点） フタロシアニン化合物は、光、熱、温度等に対して安定
であり、堅牢性に優れている。特に、金属フタロシアニ
ンは、その高い安定性と強い色調から、各種の染料ある
いは顔料として広く用いられているほか、大きなΠ電子
共役系の中に金属イオンが存在するため、電導、光電
導、エネルギー変換、電極、触媒などの材料として、ま
た、高分子とブレンドすることにより、高度の機能を有
するフィルムや薄膜等の高分子材料などとして注目さ
れ、種々研究が行われている。(Prior Art and Problems Thereof) Phthalocyanine compounds are stable to light, heat, temperature and the like, and have excellent robustness. In particular, metal phthalocyanines are widely used as various dyes or pigments due to their high stability and strong color tone.Because metal ions are present in a large Π-electron conjugated system, metal phthalocyanines are used for conducting, photoconducting and energy conversion. As a material for electrodes, catalysts and the like, and as a polymer material such as a film or a thin film having a high function by blending with a polymer, attention has been paid to various studies.
これらフタロシアニン化合物は、フタロニトリル及びフ
タル酸誘導体を原料として製造されるが、一般に溶解性
が悪い為、塗布出来ないという欠点がある。この種の化
合物の溶解性を向上させる目的で、カナディアン・ジャ
ーナル・オブ・ケミストリー（63巻,623〜631項,1985
年）には、嵩高いアルキル基またはアルコキシ基を導入
したフタロニトリルを用いて、上記置換基を持った中心
金属がCu,Co,Znのフタロシアニンを合成した例が報告さ
れているが、当該フタロシアニンはハロゲン化炭化水素
への溶解性の向上はみられるものの、他の溶剤への溶解
性は不十分であった。Although these phthalocyanine compounds are produced from phthalonitrile and phthalic acid derivatives as raw materials, they generally have poor solubility and therefore cannot be applied. For the purpose of improving the solubility of this type of compound, the Canadian Journal of Chemistry (63, 623-631, 1985)
(Year) reported the synthesis of a phthalocyanine whose central metal having the above-mentioned substituents is Cu, Co, Zn using phthalonitrile having a bulky alkyl group or alkoxy group introduced. Although the solubility in halogenated hydrocarbons was improved, the solubility in other solvents was insufficient.
光記録媒体用フタロシアニンとしては、バナジルフタロ
シアニンなどが長波長側に吸収を持つ為有利な事が知ら
れているが、同様な方法で嵩高いアルキル基またはアル
コキシ基を導入した中心金属がVO（バナジル）のフタロ
シアニンを合成したところ、各種溶剤への溶解性は上記
金属フタロシアニンの場合より悪いことがわかった。従
って、上記方法では、入手しやすい基板であるが溶剤耐
性の悪い射出成型ポリカーボネートまたは射出成型ポリ
メチルメタクリレート等のプラスチック基板に直接塗布
可能な色素を得ることは難しい。従って、さらに溶解性
を向上させる置換基を持ったフタロシアニン及び、その
原料であるフタロニトリル化合物が望まれていた。As a phthalocyanine for optical recording media, vanadyl phthalocyanine is known to be advantageous because it has absorption on the long wavelength side. However, the central metal introduced with a bulky alkyl group or alkoxy group by the same method is VO (vanadyl). ), The solubility in various solvents was found to be worse than that of the above metal phthalocyanine. Therefore, according to the above method, it is difficult to obtain a dye which is a substrate which is easily available but which can be directly applied to a plastic substrate such as injection-molded polycarbonate or injection-molded polymethylmethacrylate having poor solvent resistance. Therefore, a phthalocyanine having a substituent that further improves solubility and a phthalonitrile compound as a raw material thereof have been desired.
II 発明の目的 本発明の目的は、溶解性のよいフタロシアニン化合物の
原料となるフタロニトリル化合物を提供することにあ
る。II Object of the Invention An object of the present invention is to provide a phthalonitrile compound as a raw material of a phthalocyanine compound having good solubility.
III 発明の開示 このような目的は、下記の本発明によって達成される。III DISCLOSURE OF THE INVENTION Such an object is achieved by the present invention described below.
即ち、本発明は、含フッ素置換基を持つことを特徴とす
るフタロニトリル化合物である。That is, the present invention is a phthalonitrile compound having a fluorine-containing substituent.
本発明のフタロニトリル化合物は、フタロシアニンに変
換することにより、近赤外領域での吸収が大であり、化
学的に安定であり、しかも各種溶剤、例えばアセトン等
のケトン系溶剤、メチルセロソルブ等のセロソルブ系溶
剤、オクタフルオロペンチルアルコール等のアルコール
系溶剤、ベンゼン等の芳香族系溶剤等に良く溶解するフ
タロシアニン化合物を提供する為、塗布可能な光記録媒
体用フタロシアニン系色素の原料としてとして有用であ
る。The phthalonitrile compound of the present invention has a large absorption in the near infrared region by being converted into phthalocyanine and is chemically stable, and further, various solvents such as a ketone solvent such as acetone, methyl cellosolve, etc. It is useful as a raw material for a phthalocyanine dye that can be applied to an optical recording medium in order to provide a phthalocyanine compound that is well soluble in a cellosolve solvent, an alcohol solvent such as octafluoropentyl alcohol, an aromatic solvent such as benzene, and the like. .
IV 発明の具体的構成 以下、本発明の具体的構成について詳細に説明する。IV Specific Structure of the Invention Hereinafter, the specific structure of the present invention will be described in detail.
本発明は、下記式（Ｉ） Phn-（ORf）n （Ｉ） （式中、Phnはフタロニトリルを表し、ORfはフッ素置換
アルコキシ基を表し、ｎは１〜４の整数を表す）で示さ
れることを特徴とするフタロニトリル化合物である。The present invention has the following formula (I) Phn- (ORf) n (I) in (wherein, Phn represents phthalonitrile, OR f represents a fluorine-substituted alkoxy group, n is an integer of 1 to 4) It is a phthalonitrile compound characterized by being shown.
上記フタロニトリルPhnは下記式（II）で表されるもの
である。The phthalonitrile Phn is represented by the following formula (II).
上記置換基ORfとしては直鎖または分岐のアルコキシ基
にフッ素が一個以上置換されたものから選択されるが、
原料入手の容易さから、OCH2(CF2)mZ（ｍは１〜５の整
数、Ｚは水素原子またはフッ素原子）の一般式で表され
るものが望ましい。置換基ORfの数ｎはフタロニトリル
あたり１〜４の整数であ る。置換基ORfの置換位置は式（II）中の１〜４のいず
れかである。フタロニトリル４個の置換位置のうちORf
が置換されていない残りの置換位置には水素原子が結合
されているが、このうち一部または全部は他の置換基、
例えば、アルキル基又はアルコキシ基あるいは塩素等の
ハロゲン原子等で置換されていてもさしつかえない。The substituent ORf is selected from linear or branched alkoxy groups in which one or more fluorines are substituted,
The one represented by the general formula of OCH 2 (CF 2 ) m Z (m is an integer of 1 to 5 and Z is a hydrogen atom or a fluorine atom) is preferable from the viewpoint of easy availability of raw materials. The number n of the substituents ORf is an integer of 1 to 4 per phthalonitrile. It The substitution position of the substituent ORf is any one of 1 to 4 in the formula (II). ORf among four substitution positions of phthalonitrile
A hydrogen atom is bonded to the remaining substitution position where is not substituted, but some or all of these are other substituents,
For example, it may be substituted with an alkyl group, an alkoxy group or a halogen atom such as chlorine.
以下に本発明の具体的化合物の例を示す。Examples of specific compounds of the present invention are shown below.
（１）テトラ−（2,2,3,3,4,4,5,5−オクタフルオロペ
ンチルオキシ）−フタロニトリル （２）テトラ−（2,2,3,3−テトラフルオロプロポキ
シ）−フタロニトリル （３）テトラ−（2,2,2−トリフルオロエトキシ）−フ
タロニトリル 本発明のフタロシアニン化合物は、例えば、カナディア
ン・ジャーナル・オブ・ケミストリー（63巻,623〜631
頁,1985年）等に記載されている方法により容易に合成
が可能である。即ち、ニトロ置換フタロニトリルとフル
オロアルコール類とを非プロトン性極性溶媒中、炭酸カ
リウムの存在下反応させることによりフルオロアルコキ
シ置換フタロニトリルが得られる。こうして得られる含
フッ素フタロニトリルは、モリブデン酸アンモニウム触
媒の存在下、又は無触媒の条件で各種金属塩化物及び尿
素と180-200℃で反応させることにより、含フッ素アル
コキシ置換された金属フタロシアニンに変換することが
できる。また、含フッ素フタロニトリルを金属塩の存在
下、又は非存在下に、アルコール中DBU等の有機塩基と
反応させることによっても含フッ素アルコキシ金属フタ
ロシアニン又は含フッ素アルコキシ無金属フタロシアニ
ンに変換できる。(1) Tetra- (2,2,3,3,4,4,5,5-octafluoropentyloxy) -phthalonitrile (2) Tetra- (2,2,3,3-tetrafluoropropoxy) -phthalo Nitrile (3) Tetra- (2,2,2-trifluoroethoxy) -phthalonitrile The phthalocyanine compound of the present invention can be obtained, for example, by the Canadian Journal of Chemistry (Volume 63, 623-163).
Page, 1985) and the like. That is, a fluoroalkoxy-substituted phthalonitrile is obtained by reacting a nitro-substituted phthalonitrile with a fluoroalcohol in an aprotic polar solvent in the presence of potassium carbonate. The fluorine-containing phthalonitrile thus obtained is converted to a fluorine-containing alkoxy-substituted metal phthalocyanine by reacting with various metal chlorides and urea at 180-200 ° C in the presence of an ammonium molybdate catalyst or in the absence of a catalyst. can do. Alternatively, the fluorine-containing phthalonitrile can be converted into a fluorine-containing alkoxy metal phthalocyanine or a fluorine-containing alkoxy metal-free phthalocyanine by reacting with an organic base such as DBU in alcohol in the presence or absence of a metal salt.
Ｖ 発明の具体的実施例 以下、本発明の具体的実施例を示し、本発明をさらに詳
細に説明する。 V Specific Examples of the Invention Hereinafter, specific examples of the present invention will be shown to explain the present invention in more detail.
実施例１ ４−ニトロフタロニトリル（III）2.49g（14.4mmol）,
2,2,3,3,4,4,5,5−オクタフルオロペンチルアルコール
8.70g（37.5mmol），炭酸カリウム6.0gを窒素雰囲気
下、乾燥DMF20ml中70℃で９時間反応させた。（炭酸カ
リウムは、2.0gずつ、３回に分けて３時間毎に仕込ん
だ。）反応終了後、反応液を室温（25℃）まで冷却し、
水200mlを注ぎエーテル抽出（200mlx2回）した。エーテ
ル抽出層は、硫酸マグネシウムで一晩乾燥後、エーテル
を留去し、さらに真空ポンプで乾燥した。Example 1 4-nitrophthalonitrile (III) 2.49 g (14.4 mmol),
2,2,3,3,4,4,5,5-octafluoropentyl alcohol
8.70 g (37.5 mmol) and 6.0 g of potassium carbonate were reacted under a nitrogen atmosphere in dry DMF 20 ml at 70 ° C. for 9 hours. (The potassium carbonate was added in 2.0 g portions in 3 batches every 3 hours.) After the reaction was completed, the reaction solution was cooled to room temperature (25 ° C.),
200 ml of water was poured and the mixture was extracted with ether (200 ml × 2 times). The ether extract layer was dried over magnesium sulfate overnight, then the ether was distilled off, and further dried by a vacuum pump.
収量4.51g（12.6mmol）［収率87.6％］ 融点42.5〜44.0℃ IR（KBr） 2250,2240,1610,1575,1495,1310, 1260,1180,1160,1135,1120,980, 895,815,655cm-1 NMR δ（CDCl3） 4.58［2H,t.,J＝12.5Hz］,6.07 ［1H,t.t.,J＝51.5Hz,5.5Hz］， 7.33［1H,d.,J＝8.0Hz］,7.38 ［1H,s.］,7.83［1H,d.,J＝8.0Hz］ 実施例２ ４−ニトロフタロニトリル（III）2.49g（14.4mmol）,
2,2,3,3−テトラフルオロプロピルアルコール4.95g（3
7.5mmol），炭酸カリウム6.0gを用い、実施例１と同様
にして、3.49g（13.5mmol）［収率93.9％］を得た。Yield 4.51 g (12.6 mmol) [Yield 87.6%] Melting point 42.5-44.0 ° C IR (KBr) 2250,2240,1610,1575,1495,1310, 1260,1180,1160,1135,1120,980, 895,815,655 cm -1 NMR δ (CDCl 3 ) 4.58 [2H, t., J = 12.5Hz], 6.07 [1H, tt, J = 51.5Hz, 5.5Hz], 7.33 [1H, d., J = 8.0Hz], 7.38 [1H , s.], 7.83 [1 H, d., J = 8.0 Hz] Example 2 2.49 g (14.4 mmol) of 4-nitrophthalonitrile (III),
2,2,3,3-Tetrafluoropropyl alcohol 4.95 g (3
7.5 mmol) and 6.0 g of potassium carbonate were used in the same manner as in Example 1 to obtain 3.49 g (13.5 mmol) [yield 93.9%].
融点72.0〜73.0℃ IR（KBr） 2240,1605,1570,1495,1305,1260, 1150,1105,980,895cm-1 NMR δ（CDCl3） 4.47［2H,t.t.,J＝12..0Hz, 0.7Hz］,5.97［1H,t.t.,J＝ 52.0Hz,4.0Hz］， 7.22［1H,d.,J＝8.0Hz］， 7.32［1H,s］7.73［1H,d., Ｊ＝8.0Hz］ 実施例３ ４−ニトロフタロニトリル（III）2.49g（14.4mmol）,
2,2,2−トリフルオロエタノール3.75g（37.5mmol），炭
酸カリウム6.0gを用い、実施例１と同様にして、3.08g
（13.6mmol）［収率94,6％］を得た。Melting point 72.0-73.0 ° C IR (KBr) 2240,1605,1570,1495,1305,1260, 1150,1105,980,895cm -1 NMR δ (CDCl 3 ) 4.47 [2H, tt, J = 12.0.0Hz, 0.7Hz ], 5.97 [1H, tt, J = 52.0Hz, 4.0Hz], 7.22 [1H, d., J = 8.0Hz], 7.32 [1H, s] 7.73 [1H, d., J = 8.0Hz] Example 2.49 g (14.4 mmol) of 4-nitrophthalonitrile (III),
3.08 g of 2,2,2-trifluoroethanol (3.75 g, 37.5 mmol) and potassium carbonate (6.0 g) were used in the same manner as in Example 1.
(13.6 mmol) [yield 94.6%] was obtained.
融点76.0〜77.0℃ IR（KBr） 2245,1610,1585,1495,1320, 1255cm-1 NMR δ（CDCl3） 4.46［2H,q.,J＝7.7HzHz, 7.23［1H,d.,J＝8.6Hz］， 7.30［1H,s.］7.73［1H,d., Ｊ＝8.6Hz］ 次に、参考例として含フッ素置換フタロシアニン化合物
への変換例を示す。Melting point 76.0-77.0 ° C IR (KBr) 2245,1610,1585,1495,1320, 1255cm -1 NMR δ (CDCl 3 ) 4.46 [2H, q., J = 7.7HzHz, 7.23 [1H, d., J = 8.6 Hz], 7.30 [1H, s.] 7.73 [1H, d., J = 8.6Hz] Next, an example of conversion to a fluorine-containing substituted phthalocyanine compound is shown as a reference example.
参考例１ 化合物（IV）（ORf＝OCH2（CF2)4Ｈ）2.15g（6.0mmo
l），三塩化バナジウム0.38g（2.4mmol），尿素7.0gを1
90〜220℃に加熱し、溶融状態で１時間反応させた。反
応終了後、室温まで冷却した後、水及びクロロホルムを
加え生成物を溶かし出した。分液したクロロホルム層
は、硫酸マグネシウムを加え一晩乾燥した。溶媒を留去
して得られる固体1.66gをシリカゲルカラムで、トルエ
ンを溶離液として分離精製し、黒緑色固体1.18g（0.79m
mol）を得た。Reference Example 1 Compound (IV) (OR f = OCH 2 (CF 2 ) 4 H) 2.15 g (6.0 mmo
l), vanadium trichloride 0.38g (2.4mmol), urea 7.0g 1
The mixture was heated to 90 to 220 ° C. and reacted in a molten state for 1 hour. After completion of the reaction, the mixture was cooled to room temperature, water and chloroform were added to dissolve the product. The separated chloroform layer was added with magnesium sulfate and dried overnight. 1.66 g of a solid obtained by distilling off the solvent was purified by a silica gel column using toluene as an eluent to obtain 1.18 g of a black-green solid (0.79 m
mol) was obtained.
収率52.7％ λmax（トルエン）＝695nm（logε＝5.20） MASS（FD） 1500（Ｍ＋１） VI 発明の具体的効果 本発明のフタロニトリルから得られるフタロシアニシア
ニン化合物は各種溶剤、例えばアセトン等のケトン系溶
剤、メチルセロソルブ系溶剤、オクタフルオロペンチル
アルコール等のアルコール系溶剤、ベンゼン等の芳香族
系溶剤等に良く溶解する為、本発明のフタロニトリル化
合物は塗布可能な光記録媒体用フタロシアニン色素の原
料として有用である。Yield 52.7% λ max (toluene) = 695 nm (log ε = 5.20) MASS (FD) 1500 (M + 1) VI Specific effects of the invention The phthalocyanicyanine compounds obtained from the phthalonitrile of the present invention are various solvents such as acetone. The phthalonitrile compound of the present invention can be applied to the phthalocyanine dye for optical recording media, since it is well soluble in the ketone solvent, methyl cellosolve solvent, alcohol solvent such as octafluoropentyl alcohol, and aromatic solvent such as benzene. It is useful as a raw material.
Claims (1)
アルコキシ基を表し、ｎは１〜４の整数を表す）で示さ
れることを特徴とするフタロニトリル化合物。1. The following formula (I) Phn- (OR f ) n (I) (wherein Phn represents phthalonitrile, OR f represents a fluorine-substituted alkoxy group, and n represents an integer of 1 to 4). ) The phthalonitrile compound is represented by the formula (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62147840A JPH0788346B2 (en) | 1987-06-16 | 1987-06-16 | Fluorine-containing alkoxyphthalonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62147840A JPH0788346B2 (en) | 1987-06-16 | 1987-06-16 | Fluorine-containing alkoxyphthalonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63313760A JPS63313760A (en) | 1988-12-21 |
| JPH0788346B2 true JPH0788346B2 (en) | 1995-09-27 |
Family
ID=15439439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62147840A Expired - Lifetime JPH0788346B2 (en) | 1987-06-16 | 1987-06-16 | Fluorine-containing alkoxyphthalonitrile |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0788346B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061388A (en) * | 1990-06-01 | 1991-10-29 | The Dow Chemical Company | Novel phthalonitriles and phthalocyanines as lubricity-enhancing additives |
| US5118431A (en) * | 1990-06-01 | 1992-06-02 | The Dow Chemical Company | Phthalonitriles and phthalocyanines as lubricity-enhancing additives |
-
1987
- 1987-06-16 JP JP62147840A patent/JPH0788346B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63313760A (en) | 1988-12-21 |
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