JPH031352B2 - - Google Patents
Info
- Publication number
- JPH031352B2 JPH031352B2 JP15724083A JP15724083A JPH031352B2 JP H031352 B2 JPH031352 B2 JP H031352B2 JP 15724083 A JP15724083 A JP 15724083A JP 15724083 A JP15724083 A JP 15724083A JP H031352 B2 JPH031352 B2 JP H031352B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- formula
- compound
- compound represented
- dicyanoanthraquinone
- 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
Links
- -1 anthraquinone compound Chemical class 0.000 claims description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 239000004744 fabric Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical group 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- JCVLRGLQOHKUMK-UHFFFAOYSA-N 3-(3-ethylhexoxy)propan-1-amine Chemical compound CCCC(CC)CCOCCCN JCVLRGLQOHKUMK-UHFFFAOYSA-N 0.000 description 2
- WONPUYDAAHCRKZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-dicarbonitrile Chemical compound C1=CC(C#N)=C(C#N)C2=C1C(=O)C1=CC=CC=C1C2=O WONPUYDAAHCRKZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 description 1
- UGOABQVUDBNSOX-UHFFFAOYSA-N 9,10-dioxoanthracene-2,3-dicarbonitrile Chemical compound N#CC1=C(C#N)C=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 UGOABQVUDBNSOX-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
【発明の詳細な説明】
本発明はアントラキノン化合物に関する。更に
詳しくは式(1)
〔式(1)においてR1は水素又は炭素数１〜４の
アルキルを表わす〕
で表わされるアントラキノン化合物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to anthraquinone compounds. For more details, use formula (1) [In formula (1), R 1 represents hydrogen or alkyl having 1 to 4 carbon atoms.] The present invention relates to an anthraquinone compound represented by the following.
本発明のアントラキノン化合物は次のような工
程をえて製造することができる。 The anthraquinone compound of the present invention can be produced through the following steps.
〔式〔Ａ〕，〔Ｂ〕，〔Ｃ〕，〔Ｄ〕，〔Ｅ〕及び(1
)に
おいてR1は前記と同じ意味を表わし、R2は置換
又は非置換アルキルアミンの残基を表わす〕
即ち、特公昭36−3829号の方法に準じて、〔Ａ〕
をナトリウムメチラートと反応させて〔Ｂ〕及び
〔Ｃ〕の混合物となし、次に置換又は非置換アル
キルアミンと反応させ〔Ｄ〕及び〔Ｅ〕の混合物
を得る。或いは、特公昭36−3829号及び特開昭53
−74629号の方法に準じて〔Ａ〕よりナトリウム
メチラートの存在下、置換又非置換アルキルアミ
ンと反応させて〔Ｄ〕及び〔Ｅ〕の混合物を得
る。次に〔Ｄ〕及び〔Ｅ〕の混合物を例えばジク
ロロベンゼンに溶解し60〜120℃好ましくは80〜
100℃で硫化水素ガスを反応させ(1)を得ることが
できる。 [Formula [A], [B], [C], [D], [E] and (1
), R 1 has the same meaning as above, and R 2 represents a substituted or unsubstituted alkylamine residue] That is, according to the method of Japanese Patent Publication No. 36-3829, [A]
is reacted with sodium methylate to give a mixture of [B] and [C], and then with a substituted or unsubstituted alkylamine to give a mixture of [D] and [E]. Or, JP-A No. 36-3829 and JP-A-53
According to the method of No. 74629, [A] is reacted with a substituted or unsubstituted alkylamine in the presence of sodium methylate to obtain a mixture of [D] and [E]. Next, the mixture of [D] and [E] is dissolved in, for example, dichlorobenzene at 60-120°C, preferably at 80-120°C.
(1) can be obtained by reacting hydrogen sulfide gas at 100℃.
こうして得られる粗製の化合物（色素〕は通常
の染色・着色等には十分な品質であるが、更に高
純度が必要な場合には再結晶法、昇華法等により
精製して所望の品質の化合物（色素）を得る事が
できる。 The crude compound (pigment) obtained in this way is of sufficient quality for normal dyeing and coloring, but if higher purity is required, it can be purified by recrystallization, sublimation, etc. to obtain the desired quality compound. (dye) can be obtained.
本発明によつて得られる式(1)で表わされるアン
トラキノン化合物は、それ自体で常法によりポリ
エステル繊維を淡緑青色に染色することができ
る。そして得られた染色物は太陽光の熱エネルギ
ーを効率よく吸収し、保温効果が優れているとい
う興味ある特性を示す。 The anthraquinone compound represented by formula (1) obtained by the present invention can dye polyester fibers in a light green-blue color by itself by a conventional method. The resulting dyed material exhibits interesting properties in that it efficiently absorbs the thermal energy of sunlight and has excellent heat retention effects.
なお他のポリエステル繊維染色可能な染料類と
配合染色しても同様な特性を示す。又、式(1)の化
合物は合成樹脂の着色剤としても有用である。以
下実施例により本発明を具体的に説明する。 Furthermore, the same characteristics are exhibited even when mixed with other dyes capable of dyeing polyester fibers. The compound of formula (1) is also useful as a coloring agent for synthetic resins. The present invention will be specifically explained below using Examples.
実施例 １
メタノール50部中に、28％ナトリウムメチラー
トのメタノール溶液8.7部、１，４−ジアミノ−
２，３−ジシアノアントラキノン8.6部を仕込み
60℃で２時間反応させ、次いでγ−２−エチルヘ
キシルオキシプロピルアミン11.2部を仕込み60−
65℃で３時間反応させる。メタノール50部を加え
冷却し、過、メタノールで洗浄し水洗後乾燥し
て次式(2)
で表わされる化合物11.4部を得た。次に式(2)の化
合物９部をｏ−ジクロロベンゼン100部に溶解し、
85−95℃で硫化水素ガスを通じ(2)式の化合物が薄
層クロマトグラフで認められなくなるまで反応さ
せる。冷却後メタノール200部で希釈し、過す
る。得られた結晶を更にアセトンで懸濁洗浄、
過し、水洗乾燥して次式(3)
で表わされる化合物5.1部を得た。Example 1 8.7 parts of a 28% methanol solution of sodium methylate in 50 parts of methanol, 1,4-diamino-
Contains 8.6 parts of 2,3-dicyanoanthraquinone
The reaction was carried out at 60°C for 2 hours, and then 11.2 parts of γ-2-ethylhexyloxypropylamine was added to give a 60-
React at 65°C for 3 hours. Add 50 parts of methanol, cool, wash with filtrate and methanol, wash with water, and dry. 11.4 parts of the compound represented by was obtained. Next, 9 parts of the compound of formula (2) were dissolved in 100 parts of o-dichlorobenzene,
The reaction is carried out at 85-95°C by passing hydrogen sulfide gas until the compound of formula (2) is no longer observed in thin layer chromatography. After cooling, dilute with 200 parts of methanol and filter. The obtained crystals were further suspended and washed with acetone.
After filtering, washing with water and drying, use the following formula (3). 5.1 parts of the compound represented by was obtained.
融点300℃以上、λmax＝840nm（テトラヒドロ
フラン）
実施例 ２
実施例１において、γ−２−エチルヘキシルオ
キシプロピルアミンの代りにγ−エトキシプロピ
ルアミンを用いて同様に反応を行い(3)式の化合物
4.9部を得た。 Melting point: 300°C or higher, λmax = 840 nm (tetrahydrofuran) Example 2 A reaction was carried out in the same manner as in Example 1, using γ-ethoxypropylamine instead of γ-2-ethylhexyloxypropylamine, and a compound of formula (3) was obtained.
Got 4.9 copies.
実施例 ３
実施例１において１，４−ジアミノ−２，３−
ジシアノアントラキノンの代りに、１−アミノ−
４−メチルアミノ−２，３−ジシアノアントラキ
ノンを用いて同様に反応を行い次式(4)
で表わされる化合物４部を得た。Example 3 In Example 1, 1,4-diamino-2,3-
Instead of dicyanoanthraquinone, 1-amino-
A similar reaction was carried out using 4-methylamino-2,3-dicyanoanthraquinone and the following formula (4) was obtained. 4 parts of the compound represented by was obtained.
融点300℃以上、λmax＝843nm（テトラヒドロ
フラン）
実施例 ４
実施例１において１，４−ジアミノ−２，３−
ジシアノアントラキノンの代りに１−アミノ−４
−ブチルアミノ−２，３−ジシアノアントラキノ
ンを用いて同様に反応を行い次式(5)
で表わされる化合物を得、次いで式(5)で表わされ
る化合物５部をジナフチルメタンジスルホン酸ナ
トリウム５部、水40部と共にサンドミルで充分に
湿式粉砕し、微細に分散した状態とした後スプレ
ードライヤーで乾燥し、水に微分可能な粉末を得
た。この粉末５部に、酢酸及び酢酸ソーダにてPH
4.5に調整した水3000部を加えて色素の水分散液
を調製し、この分散液にポリエステル布50部を浸
漬し高温高圧染色機にて130℃、
30分間染色して淡青緑色に染色されたポリエステ
ル布を得た。得られた染色ポリエステル布を太陽
光下に10分間置くと布の温度は25℃から38℃に上
昇した。これに対して未染色ポリエステル布は25
℃から30℃の上昇に留まつた。 Melting point: 300°C or higher, λmax = 843 nm (tetrahydrofuran) Example 4 In Example 1, 1,4-diamino-2,3-
1-amino-4 instead of dicyanoanthraquinone
A similar reaction was carried out using -butylamino-2,3-dicyanoanthraquinone and the following formula (5) was obtained. A compound represented by formula (5) was obtained, and then 5 parts of the compound represented by formula (5) was thoroughly wet-pulverized in a sand mill with 5 parts of sodium dinaphthylmethane disulfonate and 40 parts of water to form a finely dispersed state, and then dried in a spray dryer. to obtain a water-differentiable powder. Add 5 parts of this powder to PH with acetic acid and sodium acetate.
An aqueous dispersion of the dye was prepared by adding 3,000 parts of water adjusted to 4.5, and 50 parts of polyester cloth was immersed in this dispersion and dyed in a high-temperature, high-pressure dyeing machine at 130°C for 30 minutes, resulting in a light bluish-green color. A polyester cloth was obtained. When the resulting dyed polyester cloth was placed under sunlight for 10 minutes, the temperature of the cloth rose from 25°C to 38°C. In contrast, undyed polyester fabric has a
The rise remained at 30℃.
Claims (1)
アルキルを表わす〕 で表わされるアントラキノン化合物。[Claims] 1 Formula (1) [In formula (1), R 1 represents hydrogen or alkyl having 1 to 4 carbon atoms.] An anthraquinone compound represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15724083A JPS6049063A (en) | 1983-08-30 | 1983-08-30 | Anthraquinone compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15724083A JPS6049063A (en) | 1983-08-30 | 1983-08-30 | Anthraquinone compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6049063A JPS6049063A (en) | 1985-03-18 |
| JPH031352B2 true JPH031352B2 (en) | 1991-01-10 |
Family
ID=15645306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15724083A Granted JPS6049063A (en) | 1983-08-30 | 1983-08-30 | Anthraquinone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6049063A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01266274A (en) * | 1988-04-13 | 1989-10-24 | Teijin Ltd | endothermic fabric |
| JP2728438B2 (en) * | 1988-07-08 | 1998-03-18 | 帝人株式会社 | Insulating fabric |
-
1983
- 1983-08-30 JP JP15724083A patent/JPS6049063A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6049063A (en) | 1985-03-18 |
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