JPH0651845B2 - Diaryl methane compounds - Google Patents
Diaryl methane compoundsInfo
- Publication number
- JPH0651845B2 JPH0651845B2 JP61043565A JP4356586A JPH0651845B2 JP H0651845 B2 JPH0651845 B2 JP H0651845B2 JP 61043565 A JP61043565 A JP 61043565A JP 4356586 A JP4356586 A JP 4356586A JP H0651845 B2 JPH0651845 B2 JP H0651845B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- compound
- present
- diarylmethane
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/1366—Organic colour formers, e.g. leuco dyes characterised solely by tri (aryl or hetaryl)methane derivatives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Color Printing (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、新規なジアリールメタン系化合物に関するも
のであり、詳しくは、繊維用染料、感熱色素、感圧色素
あるいは、ラジカル写真用色素等の前駆体として有用な
アリールメタン系化合物に関するものである。TECHNICAL FIELD The present invention relates to a novel diarylmethane compound, and more specifically, to a dye for fibers, a heat-sensitive dye, a pressure-sensitive dye, a radical photographic dye, or the like. The present invention relates to an arylmethane compound useful as a precursor.
本発明は、一般式〔Ｉ〕 （式中、R1、R2はアルキル基を示し、Ｘは水素原子また
はアルキル基を示す。）で表わされるジアリールメタン
系化合物を要旨とするものである。The present invention has the general formula [I] (In the formula, R 1 and R 2 represent an alkyl group, and X represents a hydrogen atom or an alkyl group.) The gist is a diarylmethane compound.
本発明のジアリールメタン系化合物は、例えば、次のよ
うにして構造することが出来る。The diarylmethane compound of the present invention can be structured, for example, as follows.
すなわち、下記構造式〔II〕 で表わされる３−ホルミルチオクロモン１モル比と、下
記一般式〔III〕 で表わされるN,N−ジアルキルアニリン誘導体（式中
R1、R2およびＸは前記一般式〔Ｉ〕におけると同一の意
義を有する。）２モル比以上とを硫酸等の酸性溶媒中で
反応させることにより製造することが出来る。That is, the following structural formula [II] 1-molar ratio of 3-formylthiochromone represented by the following general formula [III] N, N-dialkylaniline derivative represented by
R 1 , R 2 and X have the same meaning as in the general formula [I]. ) It can be produced by reacting with 2 mol ratio or more in an acidic solvent such as sulfuric acid.
本発明の一般式〔Ｉ〕におけるR1、R2の具体例として
は、メチル基、エチル基または下記の直鎖または分岐鎖
状のアルキル基を挙げることが出来る。これらの直鎖ま
たは分岐鎖状のアルキル基としては、プロピル基、ブチ
ル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル
基、ノニル基、デシル基、ドデシル基等を挙げることが
出来る。Specific examples of R 1 and R 2 in the general formula [I] of the present invention include a methyl group, an ethyl group or the following linear or branched alkyl group. Examples of these linear or branched alkyl groups include propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group and dodecyl group.
Ｘとしては、水素原子あるいはメチル基、エチル基等の
アルキル基を挙げることが出来る。Examples of X include a hydrogen atom and an alkyl group such as a methyl group and an ethyl group.
本発明の一般式〔Ｉ〕におけるジアリールメタン系化合
物の具体例とし例えば、以下のものを挙げることが出来
る。Specific examples of the diarylmethane compound in the general formula [I] of the present invention include the followings.
本発明の一般式〔Ｉ〕で表わされるジアリールメタン系
化合物は、以下に示すように ４酢酸鉛で酸化後、過塩素酸処理によりあるいはラ
ジカル反応、例えば高圧水銀灯照射により、ラジカル分
解更に酸化を経て一般式〔IV〕 （式中R1、R2およびＸは前記一般式〔Ｉ〕におけると同
一の意義を示し、Ｙは過塩素酸イオン等の陰イオンを示
す。）で表わされるアリールメタン系色素に変化するこ
とができる。 The diarylmethane compound represented by the general formula [I] of the present invention has the following structure. After oxidation with lead tetraacetate, a general formula [IV] (wherein R 1 , R 2 and X are represented by the general formula [I] above) is obtained by radical decomposition and oxidation by perchloric acid treatment or radical reaction such as irradiation with a high pressure mercury lamp. And Y represents an anion such as a perchlorate ion, etc.), and can be changed to an arylmethane dye.
次に、本発明を実施例により、更に具体的に説明するが
本発明は、下記実施例に限定されるものではない。Next, the present invention will be described more specifically by way of examples, but the present invention is not limited to the following examples.
実施例１ ３−ホルミルチオクロモン ０．４７７ｇと、N,N−ジエチルアニリン０．７８８ｇ
を４８％硫酸水溶液１０ml中、９０℃で１６時間反応さ
せた。Example 1 3-Formylthiochromone 0.477 g and 0.788 g of N, N-diethylaniline
Was reacted in 10 ml of 48% sulfuric acid aqueous solution at 90 ° C. for 16 hours.
水１５０mlを加え、さらに飽和酢酸ナトリウム水溶液３
５mlを加える。析出した沈澱をろ過、水洗し、エタノー
ルから再結晶することにより下記式で示されるジアリー
ルメタン系化合物０．８６６ｇを得た。150 ml of water was added, and saturated aqueous sodium acetate solution 3 was added.
Add 5 ml. The deposited precipitate was filtered, washed with water, and recrystallized from ethanol to obtain 0.866 g of a diarylmethane compound represented by the following formula.
本化合物は融点１８４〜１８５℃を示し、1H−NMR(δin
CDCCl3)は１．１８（ｍ，１２Ｈ）、３．２８（ｑ，Ｊ
＝7.5Hz，６Ｈ）、３．７０（ｑ，Ｊ＝7.5Hz，２Ｈ）、
５．８０（Ｓ，１Ｈ）、６．８８（ｄ，Ｊ＝5.0Hz，４
Ｈ）、６．９７（ｄ，Ｊ＝5.0Hz，４Ｈ）、７．３６
（Ｓ，１Ｈ）、７．５０（Ｓ，３Ｈ）、８．５２（ｍ，
１Ｈ）を示した。 This compound has a melting point of 184 to 185 ° C., and 1 H-NMR (δin
CDCCl 3 ) is 1.18 (m, 12H), 3.28 (q, J
= 7.5Hz, 6H), 3.70 (q, J = 7.5Hz, 2H),
5.80 (S, 1H), 6.88 (d, J = 5.0Hz, 4
H), 6.97 (d, J = 5.0Hz, 4H), 7.36
(S, 1H), 7.50 (S, 3H), 8.52 (m,
1H).
実施例２ 実施例１のN,N−ジエチルアニリン０．７８８ｇの代わ
りに３−メチル−N,N−ジエチルアニリン０．９０９ｇ
を使用し他は実施例１と同様に処理して、下記式で示さ
れるジアリールメタン系化合物０．３５３ｇを得た。Example 2 0.909 g of 3-methyl-N, N-diethylaniline in place of 0.788 g of N, N-diethylaniline of Example 1
Was used and treated in the same manner as in Example 1 to obtain 0.353 g of a diarylmethane compound represented by the following formula.
本化合物は融点１９８〜１９９℃を示し、1H−NMR(δin
CDCl3)は１．１３(ｔ，Ｊ＝7.5Hz，１２Ｈ)、３．２８
(ｑ，Ｊ＝7.5Hz，８Ｈ)、２．２０(Ｓ，６Ｈ)、５．９
２(Ｓ，１Ｈ)、６．３４(ｄ，Ｊ＝5.0Hz，２Ｈ)、６．
４８(Ｓ，２Ｈ)、６．６３(ｄ，Ｊ＝5.0Hz，２Ｈ)、
７．２２(Ｓ，１Ｈ)、７．５０(Ｓ，３Ｈ)、８．４８
(ｍ，１Ｈ)を示した。 This compound has a melting point of 198 to 199 ° C. and 1 H-NMR (δin
CDCl 3 ) is 1.13 (t, J = 7.5 Hz, 12 H), 3.28
(q, J = 7.5Hz, 8H), 2.20 (S, 6H), 5.9
2 (S, 1H), 6.34 (d, J = 5.0Hz, 2H), 6.
48 (S, 2H), 6.63 (d, J = 5.0Hz, 2H),
7.22 (S, 1H), 7.50 (S, 3H), 8.48
(m, 1H) was shown.
実施例３ 実施例１で得られたジアリールメタン系化合物 ０．６２ｇと４酢酸鉛０．６ｇを氷酢酸１０mlに加え、
室温２時間撹拌する。飽和塩化ナトリウム水溶液１００
mlを加え、析出した結晶をろ過、水洗する。この結晶を
氷酢酸１０mlに溶かし、６０％過塩素酸水溶液数滴を加
える。この溶液を水５０mlに注ぎ、析出した結晶をろ過
し、エタノールから再結晶して下記式で示されるジアリ
ールメタン系色素を得た。Example 3 Diarylmethane compound obtained in Example 1 0.62 g and 0.6 g of lead tetraacetate were added to 10 ml of glacial acetic acid,
Stir at room temperature for 2 hours. Saturated sodium chloride aqueous solution 100
ml is added, and the precipitated crystals are filtered and washed with water. The crystals are dissolved in 10 ml of glacial acetic acid and a few drops of a 60% aqueous solution of perchloric acid are added. This solution was poured into 50 ml of water, the precipitated crystals were filtered and recrystallized from ethanol to obtain a diarylmethane dye represented by the following formula.
本化合物の融点は２１７〜２１８℃を示し、1H−NMR
（δin CHCl3）は１．２５（ｔ，Ｊ＝7.5Hz，１２
Ｈ）、３．５９（ｑ，Ｊ＝7.5Hz，８Ｈ）、６．７７
（ｄ，Ｊ＝5.0Hz，４Ｈ）、７．４０（ｄ，Ｊ＝5.0Hz，
４Ｈ）、７．６１（Ｓ，３Ｈ）、８．００（Ｓ，１Ｈ）
８．３０（ｍ，１Ｈ）を示した。 The melting point of this compound is 217 to 218 ° C., 1 H-NMR
(Δ in CHCl 3 ) is 1.25 (t, J = 7.5 Hz, 12
H), 3.59 (q, J = 7.5Hz, 8H), 6.77
(D, J = 5.0Hz, 4H), 7.40 (d, J = 5.0Hz,
4H), 7.61 (S, 3H), 8.00 (S, 1H)
It was 8.30 (m, 1H).
実施例４ 実施例１で得られたジアリールメタン系化合物（λmax
２６０nm inエタノール）０．００４５０ｇをエタノー
ル１００mlに溶解し、１００Ｗ高圧水銀灯を２５℃で
０．５時間照射したところ、λmax６４２nm（ε＝８．
５×１０4）の色素が生成した。Example 4 Diarylmethane compound obtained in Example 1 (λmax
0.00450 g of ethanol (260 nm in ethanol) was dissolved in 100 ml of ethanol and irradiated with a 100 W high-pressure mercury lamp at 25 ° C. for 0.5 hours. As a result, λmax 642 nm (ε = 8.
5 × 10 4 ) of dye was produced.
Claims (1)
はアルキル基を示す。）で表わされるジアリールメタン
系化合物。1. A general formula [I] (In the formula, R 1 and R 2 each represent an alkyl group, and X represents a hydrogen atom or an alkyl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61043565A JPH0651845B2 (en) | 1986-02-28 | 1986-02-28 | Diaryl methane compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61043565A JPH0651845B2 (en) | 1986-02-28 | 1986-02-28 | Diaryl methane compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62201967A JPS62201967A (en) | 1987-09-05 |
| JPH0651845B2 true JPH0651845B2 (en) | 1994-07-06 |
Family
ID=12667264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61043565A Expired - Lifetime JPH0651845B2 (en) | 1986-02-28 | 1986-02-28 | Diaryl methane compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0651845B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7211118B2 (en) | 2002-12-30 | 2007-05-01 | L'oreal S.A. | Composition for dyeing keratin fibers comprising a defined triheteroylmethane direct dye or leuco precursor of this dye and dyeing method using it |
| US7211117B2 (en) * | 2002-12-30 | 2007-05-01 | L'oreal S.A. | Composition for dyeing keratin fibers comprising at least one dye chosen from monoheteroyldiarylmethane direct dyes and the leuco precursors thereof and dyeing method using it |
| US7217297B2 (en) | 2002-12-30 | 2007-05-15 | L'oreal S.A. | Composition for dyeing keratin fibers comprising a defined diheteroylarylmethane direct dye or a leuco precursor of this dye and dyeing method using it |
-
1986
- 1986-02-28 JP JP61043565A patent/JPH0651845B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62201967A (en) | 1987-09-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |