JPS62201967A - Diarylmethane compound - Google Patents
Diarylmethane compoundInfo
- Publication number
- JPS62201967A JPS62201967A JP61043565A JP4356586A JPS62201967A JP S62201967 A JPS62201967 A JP S62201967A JP 61043565 A JP61043565 A JP 61043565A JP 4356586 A JP4356586 A JP 4356586A JP S62201967 A JPS62201967 A JP S62201967A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- diarylmethane
- dyes
- compound
- general formula
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002243 precursor Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- OHNUCPHKKFRBCD-UHFFFAOYSA-N 4-sulfanylidenechromene-3-carbaldehyde Chemical compound C1=CC=C2C(=S)C(C=O)=COC2=C1 OHNUCPHKKFRBCD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001001 arylmethane dye Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000001002 diarylmethane dye Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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)
Abstract
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
了り−ルメタン系化合物に関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a novel diarylmethane compound, and more specifically, it is used as a dye for textiles, a heat-sensitive dye, a pressure-sensitive dye, a radical photographic dye, etc. The present invention relates to olemethane compounds useful as precursors.
本発明は、一般式ＣＩ’）
（式中、Ｒ１，’ｆ（２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 gist of the present invention is a diarylmethane compound represented by the general formula CI') (wherein R1,'f (2 represents an alkyl group, and X represents a hydrogen atom or an alkyl group). .
本発明のジアリールメタン系化合物は、例えば、次のよ
うにして製造することが出来る。The diarylmethane compound of the present invention can be produced, for example, as follows.
すなわち、下記構造式［ＩＩ］
で表ワされるＪ−ホルミルチオクロモン１モル比と、下
記一般式〔■〕
で表わされるＮ、Ｎ−ジアルキルアニリン誘導体（式中
、Ｈｉ、ＩＨｚ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。）コ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 1 molar ratio of J-formylthiochromone represented by the following structural formula [II] and the N,N-dialkylaniline derivative represented by the following general formula [■] (where Hi, IHz and X are It has the same meaning as in the general formula [I].) It can be produced by reacting a co-molar ratio or higher in an acidic solvent such as sulfuric acid.
本発明の一般式〔ｌ〕におけるＲ１、Ｈｚ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、デンル基、ドデシル基等を挙げること
が出来る。Specific examples of R1 and Hz in the general formula [1] of the present invention include a methyl group, an ethyl group, and the following linear or branched alkyl group. Examples of these linear or branched alkyl groups include propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, denyl, dodecyl, and the like.
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 or an alkyl group such as a methyl group or an ethyl group.
本発明の一般式ＣＩＩ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 CII of the present invention include the following.
本発明の一般式ＣＩ）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
ＣＩ ） ＣＩＶ〕■グ酢酸鉛で
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
緑て一般式咽〕（式中、Ｒ１、Ｒ２およびＸは前記一般
式ＣＩＩ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 CI) of the present invention can be prepared by oxidation with lead guacetate and then treatment with perchloric acid, or by radical reaction, as shown below.
For example, by irradiation with a high-pressure mercury lamp, radical decomposition and further oxidation can be performed using the general formula (where R1, R2 and ) can be converted into the arylmethane dye represented by
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 explained in more detail with reference to examples, but the present invention is not limited to the following examples.
実施例／
○
０、ｌｌ７７ｇと、Ｎ、Ｎ−ジエチルアニリンｏ、７１
ｇＩをａｔ％硫酸水溶液１０ｍ１中、ｑｏ℃で／６時間
反応させた。Example/○ 0,1177g and N,N-diethylaniline o,71
gI was reacted in 10 ml of at% sulfuric acid aqueous solution at qo°C for 6 hours.
水／！０罰を加え、さらに飽和酢酸す） ＩＪウム水溶
液３５ｍ１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、ざ６／−夕を得た。water/! Add 35 ml of IJium aqueous solution. The deposited precipitate was filtered, washed with water, and recrystallized from ethanol to obtain diarylmethane compounds 0 and 6/-2 represented by the following formulas.
Ｈ，Ｃ２３，Ｃ２Ｈ。H, C23, C2H.
Ｎ
本化合物は融点／’１ｌｌ−／ｇ！℃を示し、’Ｈ−Ｎ
ＭＲ（δｉｎ ＣＤ０ＣＩ、）は／、／ざ（ｍ＋’＝Ｈ
）、３．２ ｔ （Ｑ、、 、Ｔ＝７．ｊＨｚ、 ＡＨ
）１．７．７ ｏ （ｑ、 Ｊ＝７．５ｎｚ、 ２
Ｈ） 、 ５． ざ θ （８，ＩＨ）
、 ｌ、、ｔ ざ （ｄ。N This compound has a melting point of /'1ll-/g! 'H-N
MR(δin CD0CI,) is /, /za(m+'=H
), 3.2 t (Q, , T=7.jHz, AH
)1.7.7 o (q, J=7.5nz, 2
H), 5. Za θ (8, IH)
, l,,t za (d.
Ｊ＝ｚ、□Ｔｌｚ、 １ＩＨ）、ｌ、、９７ （ｄ、
Ｊ−４，０Ｈ２，ＩＩＨ）、７、ｙ ｂ （Ｓ、
ＩＨ） 、 り、ｓ Ｏ（Ｅｌ、 ＪＨ）
、 ｔ、！ ２（ｍ、ＩＨ）を示した。J=z, □Tlz, 1IH), l, 97 (d,
J-4, 0H2, IIH), 7, y b (S,
IH), ri, sO (El, JH)
, t,! 2 (m, IH).
実施ｆｌＪコ
実施例／のＮ、Ｎ−ジエチルアニリンＯ０りｊざｙの代
りに３−メチル−Ｎ、Ｎ−ジエチルアニリンｏ、ｑｏｑ
９を使用し他は実施例／と同様に処理して、下記式で示
されるジアリールジメタン系化会物０．３！３ｊｌを得
た。3-Methyl-N,N-diethylaniline o,qoq instead of N,N-diethylaniline O0 of Example/
9 was used, and the other procedures were carried out in the same manner as in Example 1 to obtain 0.3!3jl of a diaryldimethane compound represented by the following formula.
Ｈ２Ｏ２，，０１Ｈ５
本化合物は融点／テサ〜／９？℃を示し、１１１ｌ１１
−１ｆδｉｎ ０ＤＯ１ｓ）は／、 ／ 、？ （ｔ、
Ｊ＝＝７．ｊｌ（Ｚ。H2O2,,01H5 This compound has a melting point of /tesa~/9? ℃, 111l11
-1fδin 0DO1s) is /, /,? (t,
J==7. jl(Z.
／ＪＨ）、３．コｇ （ｑ、 ：ｒ＝７．ｓＨｚ、 ｒ
ａ）、２．２０（ｓ、ｂＨ）、！ｒ、Ｙコ（Ｓ、 ＩＨ
）、６１．７り（ｄ。/JH), 3. g (q, :r=7.sHz, r
a), 2.20 (s, bH),! r, Y co(S, IH
), 61.7ri (d.
Ｊ＝！ｒ、０Ｈ１５，−Ｂ）、Ａ、ダｇ （Ｓ、コＨ）
、６．６３（（Ｌ、Ｊ＝！、ＯＥｚ、ＪＨ）、７．２２
（［３，ＩＨ）、７、！ｒＯ（Ｅｌ、 、７Ｈ）、ｔ
、ｌＩ ｆｆ （Ｄｌｌ、 ＩＨ）を示した。J=! r, 0H15, -B), A, dag (S, koH)
, 6.63 ((L, J=!, OEz, JH), 7.22
([3,IH),7,! rO(El, , 7H), t
, lI ff (Dll, IH).
実施ｆｌ１３
実施例／で得られたジアリールメタン系化合Ｈ，０，７
Ｃ２Ｈ。Implementation fl13 Diarylmethane compound H,0,7 obtained in Example/
C2H.
／ＮＸ Ｈ，Ｏ，Ｃ，Ｈ。/NX H, O, C, H.
ｙを氷酢酸１０ｒｔｔｌに加え、室温コ時間攪拌する。Add y to 10 rttl of glacial acetic acid and stir for 1 hour at room temperature.
飽和塩化ナトリウム水溶液／θ０Ｍを加え、析出した結
晶をろ過、水洗する。この結晶な氷酢酸７０ゴに溶かし
、６０％過塩素酸水溶液数滴を加える。この溶液を水ｓ
ｏｍｔ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ろジアリールメタン系色素を
得た。Saturated aqueous sodium chloride solution/θ0M is added, and the precipitated crystals are filtered and washed with water. Dissolve this in 70 g of glacial acetic acid and add a few drops of 60% perchloric acid aqueous solution. Add this solution to water
The precipitated crystals were filtered and recrystallized from ethanol to obtain a diarylmethane dye represented by the following formula.
ＨＩＩＣ２８，０２Ｈ。HIIC28,02H.
Ｈ，Ｕ、 ｅ２１Ｔ４
本化合物の融点はコ１７〜コｉｔ℃を示し、ＩＨ−ＮＭ
Ｒ（δｉｎ ＯｋＸ Ｕ １ｓ ）は／、コ、ｇ （ｔ
、 Ｊ＝７ＪＨｚ、／ コＨ）、 ３．５ タ
（ｑ、Ｊ＝＝＋７゜３Ｈｚ、 ざ Ｈ） 、６、り？
（ａ、：ｒ＝ｓ、ｏＨｚ、’ＩＨ）、ｑ、ｌＩｏ （
ａ、 Ｊ＝５．４７Ｈｚ、＜＜Ｈ）、’７．Ａ ／ （
Ｓ、 、７Ｈ） 、 ｆｆ、θθ（ｓ。H, U, e21T4 The melting point of this compound is C17 to Cit°C, and IH-NM
R(δin OkX U 1s ) is /, ko, g (t
, J=7JHz, / koH), 3.5 ta
(q, J==+7゜3Hz, zaH), 6, ri?
(a, :r=s, oHz, 'IH), q, lIo (
a, J=5.47Hz, <<H), '7. A/(
S, ,7H), ff, θθ(s.
ＩＨ）、ざ、、ｔ ｏ （ｍ、 ＩＨ）を示した。IH), za, t o (m, IH) were shown.
実施１４Ｊ ４’
実施例／で得られたジアリールメタン系化合吻（λｍａ
ｘ ２ ＆ Ｏｎｍ ｉｎ ｘタノール）ｏ、ｃｏ！Ｉ
ｚ。Execution 14J 4' Diarylmethane compound proboscis (λma) obtained in Example/
x 2 & Onm in x Tanol) o, co! I
z.
９をエタノール７００ｄに溶解し、１０ＯＷ高圧水銀灯
を２３℃でＯ，Ｓ時間照射したところ、λｍａｘ ４１
／−２ｎｙｒｔ （ε＝ｇ、ｓ×ｌｏ＋）の色素が生成
した。9 was dissolved in 700 d of ethanol and irradiated with a 10 OW high pressure mercury lamp at 23°C for O, S hours, λmax 41
A dye of /-2nyrt (ε=g, s×lo+) was produced.
Claims (1)
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。[Claims] General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼……………………[I] (In the formula, R^1 and R^2 represent an alkyl group, and X is 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 true JPS62201967A (en) | 1987-09-05 |
| JPH0651845B2 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) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0651845B2 (en) | 1994-07-06 |
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