JPH04173875A - Disperse dye composition and method for dyeing hydrophobic fiber - Google Patents
Disperse dye composition and method for dyeing hydrophobic fiberInfo
- Publication number
- JPH04173875A JPH04173875A JP2299841A JP29984190A JPH04173875A JP H04173875 A JPH04173875 A JP H04173875A JP 2299841 A JP2299841 A JP 2299841A JP 29984190 A JP29984190 A JP 29984190A JP H04173875 A JPH04173875 A JP H04173875A
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- Japan
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- dye
- hydrogen atom
- Prior art date
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Links
- 238000004043 dyeing Methods 0.000 title claims abstract description 21
- 239000000986 disperse dye Substances 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- 239000000835 fiber Substances 0.000 title claims abstract description 14
- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- -1 Acetoxyethyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 4
- 125000004848 alkoxyethyl group Chemical group 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 229920000728 polyester Polymers 0.000 description 10
- 239000004744 fabric Substances 0.000 description 8
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 8
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Natural products CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 7
- 239000003086 colorant Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000005844 Thymol Substances 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 229960000790 thymol Drugs 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 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 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 239000001044 red dye Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- DCBNMBIOGUANTC-UHFFFAOYSA-N [5-[(5-benzoyl-4-hydroxy-2-methoxyphenyl)methyl]-2-hydroxy-4-methoxyphenyl]-phenylmethanone Chemical compound COC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1CC(C(=CC=1O)OC)=CC=1C(=O)C1=CC=CC=C1 DCBNMBIOGUANTC-UHFFFAOYSA-N 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、分散染料組成物及び疎水性繊維の染色法に関
する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to disperse dye compositions and methods for dyeing hydrophobic fibers.
従来の技術
近年、ポリエステル繊維素材はその優れた耐熱性および
耐光性から自動車用内装素材としての用途か増加してき
ている。それにつれて、その着色剤である分散染料に対
しても一段と優れた耐光堅ろう度か求められるようにな
った。耐光堅ろう度は、従来ＪＩＳ−ＬＯ８４２に規定
する温度６３±３°Ｃて行っているか、特に自動車内装
用途では例えば８３±３℃の高温下で、しかも３００〜
６００時間の露光に耐える耐光堅ろう度か要求されてい
る。更に、自動車内装用途の中でも自動車シートとして
の用途では耐熱性を有するウレタンフオーム上にポリエ
ステル繊維材料を張って使用していることから８０°Ｃ
以上の高温になることも少なくなく更に過酷な条件に耐
える染料か求められている。BACKGROUND OF THE INVENTION In recent years, polyester fiber materials have been increasingly used as interior materials for automobiles due to their excellent heat resistance and light resistance. As a result, there has been a demand for even better light fastness for the disperse dyes used as colorants. Light fastness is conventionally measured at a temperature of 63 ± 3°C as specified in JIS-LO842, or particularly at a high temperature of 83 ± 3°C, especially for automotive interior applications, and at temperatures of 300°C to 300°C.
Light fastness is required to withstand 600 hours of exposure. Furthermore, among automotive interior applications, automotive seats use heat-resistant urethane foam covered with polyester fiber material, so it can be heated to 80°C.
There is a need for dyes that can withstand even harsher conditions, which are often exposed to higher temperatures.
一般的に、分散染料の中で、耐光堅ろう度の比較的よい
ものはアントラキノン系やキノフタロン系の染料である
がそれらは概して着色力か劣るのか欠点である。また着
色力の優れる長所を有するアゾ系の分散染料は一般的に
はアントラキノン系やキノフタロン系に比べ耐光堅ろう
度か劣るという傾向がある。殊に前記したような自動車
用内装素材としては、淡色から濃色の染色物が要求され
るので着色力に優れた分散染料で淡色から濃色まて耐光
堅ろう度の優れる染料の開発が強く望まれている。In general, among disperse dyes, anthraquinone and quinophthalone dyes have relatively good light fastness, but they generally have the disadvantage of poor coloring power. Furthermore, azo disperse dyes, which have the advantage of excellent coloring power, generally tend to have inferior light fastness compared to anthraquinone and quinophthalone dyes. In particular, as automotive interior materials mentioned above require dyed products in light to dark colors, there is a strong desire to develop disperse dyes with excellent coloring power that range from light to deep colors and have excellent light fastness. It is rare.
発明が解決しようとする課題
現在、自動車内装素材用で耐光堅ろう度の優れた分散染
料による染色は、一般的にアントラキノン系や、更に一
部キノフタロン系の染料を配合したものを使用している
が、カラーバリユーに劣り、染色濃度を高くしようとす
ると染料の使用量が著しく増え、コストが非常に高くな
る。一方、カラーバリユーがあり、中濃色分野で用いら
れるアゾ系分散染料は耐光堅牢度が十分てない。Problems to be Solved by the Invention Currently, disperse dyes with excellent light fastness for automobile interior materials are generally dyed using dyes containing anthraquinone dyes and some quinophthalone dyes. , the color value is inferior, and if you try to increase the dye density, the amount of dye used will increase significantly, and the cost will be very high. On the other hand, azo disperse dyes used in the field of medium and deep colors, which have different color values, do not have sufficient light fastness.
課題を解決するための手段
本発明者らは自動車内装用途のような過酷な条件下で、
淡色から濃色の範囲まで高耐光堅牢度を有し、且つ、カ
ラーバリユーにすぐれる経済効果の大きい特徴を有する
分散染料について鋭意検討した結果、特定の分散染料を
同時に使用することで、ベージュ色、茶色、エンジ色、
オレンジ色等の淡色から濃色の範囲で優れた耐光堅牢度
が得られるとともに、その経済効果においても極めてす
ぐれた効果をもたらす染色物が得られることを見出し、
本発明に至ったものである。Means for Solving the Problems The present inventors have developed a method under harsh conditions such as automotive interior applications.
As a result of extensive research into disperse dyes, which have high light fastness from light to dark colors and have excellent color value and are highly economical, we found that by using specific disperse dyes at the same time, beige Color: brown, red,
We have discovered that it is possible to obtain dyed products that have excellent light fastness in the range of light to dark colors such as orange, and also have extremely excellent economical effects.
This led to the present invention.
即ち、本発明は
■、下記式（１）で示される少く共１種以上の化合物と
式（２）、式（３）及び式（４）からなる群から選ばれ
る少く共１種以上の化合物よりなる分散染料組成物。That is, the present invention provides (1) at least one compound represented by the following formula (1) and at least one compound selected from the group consisting of formula (2), formula (3), and formula (4); A disperse dye composition consisting of:
式（１）：
（式中、Ｘは塩素原子又はシアノ基を、Ｙは水素原子、
塩素原工、Ａ基え１よアヤア７゜アミノ基を、Ｒ１、Ｒ
２はそれぞれ独立に、水素原子、シアノエチル基、アセ
トキシエチル基、低級アルコキシ（Ｃ＋〜４）エトキシ
エチル基、低級アルコキシカルボニルオキシエチル基又
はヒドロキシアルキル基を、Ｚは水素原子又は塩素原子
をそれぞれ表す。）式（２）：
（式中、Ｒ３は水酸基、フェノキシ基又はフェニル基で
置換されたアルキル（Ｃ，〜６）基を表す）。Formula (1): (wherein, X is a chlorine atom or a cyano group, Y is a hydrogen atom,
Chlorine raw material, A base 1, ayaa 7゜amino group, R1, R
2 each independently represents a hydrogen atom, a cyanoethyl group, an acetoxyethyl group, a lower alkoxy (C+ to 4) ethoxyethyl group, a lower alkoxycarbonyloxyethyl group, or a hydroxyalkyl group, and Z represents a hydrogen atom or a chlorine atom, respectively. ) Formula (2): (wherein, R3 represents an alkyl (C, ~6) group substituted with a hydroxyl group, a phenoxy group, or a phenyl group).
式（３）：
（式中、Ｒ４は水素原子、水酸基、アルキルカルボニル
アルコキシ基、アルコキシカルボニルアルコキシ基、ア
ルコキシカルボニルアルキル基、アルコキシアルキルア
ミノスルホニル基、又はアシルオキシ基を、Ｒ５は水素
原子又はメチル基をそれぞれ表す。）式（４）：
２、前記第１項に記載の分散染料組成物を用いることを
特徴とする疎水性繊維の染色法３、前記第１項に記載の
式（１）で示される少く共１種以上の化合物と式（２）
、式（３）、式（４）からなる群から選ばれる少く共１
種以上の化合物を用いることを特徴とする疎水性繊維の
染色法を提供する。Formula (3): (wherein, R4 is a hydrogen atom, a hydroxyl group, an alkylcarbonylalkoxy group, an alkoxycarbonylalkoxy group, an alkoxycarbonylalkyl group, an alkoxyalkylaminosulfonyl group, or an acyloxy group, and R5 is a hydrogen atom or a methyl group. ) Formula (4): 2. Hydrophobic fiber dyeing method 3 characterized by using the disperse dye composition described in item 1 above. At least one or more compounds and formula (2)
, at least 1 selected from the group consisting of formula (3) and formula (4)
Provided is a method for dyeing hydrophobic fibers characterized by using more than one type of compound.
本発明の染料組成物は、赤色分散染料として用いられる
。これに更に他の染料を配合して用いることも出来る。The dye composition of the present invention is used as a red disperse dye. It is also possible to further mix and use other dyes.
黄色系染料、青色系染料との配合により極めて広範囲な
色調が得られるか、この時、他色系染料と配合される本
発明の赤色染料の割合は（０〜９９） ： （１００
〜１）であり、好ましくは（０〜９５） ： （１
００〜５）である。A very wide range of color tones can be obtained by blending with yellow dyes and blue dyes. At this time, the ratio of the red dye of the present invention blended with other color dyes is (0 to 99): (100)
~1), preferably (0~95): (1
00 to 5).
次に超重光用として通常用いられる処決と本発明処決と
を比較することにより、その経済効果を説明する。Next, the economic effects will be explained by comparing the treatment normally used for ultra-heavy light and the treatment of the present invention.
＊ １ ＊３
＄４黄色染料：
Ｃ！
赤色染料：
ｌ
表１の結果より明らかなように本発明例は比較例に比べ
同色、同濃度を得るのに約３０％も少くてすみ経済的効
果は非常に大きい。*1 *3
$4 Yellow dye: C! Red dye: l As is clear from the results in Table 1, the present invention example requires approximately 30% less dye than the comparative example to obtain the same color and density, and has a very large economical effect.
本発明において、式（１）と式（２）、（３）、（４）
からなる群から選ばれる染料との混合比率は（１〜８０
）：（９９〜２０）好ましくは（５〜７０） ： （９
５〜３０）である。In the present invention, formula (1) and formulas (2), (3), (4)
The mixing ratio with the dye selected from the group consisting of (1 to 80
): (99-20) Preferably (5-70): (9
5 to 30).
本発明の分散染料組成物は個々の化合物を別々に常法に
より微粒子化処理してから所望の混合割合に混合するか
、式（１）〜式（４）で示される化合物（染料原末）を
あらかじめ所望の割合に混合した後、常法により微粒子
化処理することによって得られる。The disperse dye composition of the present invention can be prepared by separately processing each compound into fine particles using a conventional method and then mixing them in a desired mixing ratio, or by combining the compounds represented by formulas (1) to (4) (dye base powder). It can be obtained by pre-mixing in a desired ratio and then micronizing the mixture by a conventional method.
このようにして微粒子代品を用いて染色することにより
、高耐光性を有し、且つカラーバリユーの高く、経済効
果の大きい染色物を得ることができる。By dyeing using the fine particle substitute in this manner, it is possible to obtain a dyed product that has high light fastness, has a high color value, and has a large economic effect.
また、本発明の染色法において紫外線吸収剤を併用する
ことにより更に耐光性の優れた染色物を得ることも出来
る。本発明で用いることが出来る紫外線吸収剤の例とし
て次のものかあげられる。Further, by using an ultraviolet absorber in the dyeing method of the present invention, a dyed product with even better light resistance can be obtained. Examples of ultraviolet absorbers that can be used in the present invention include the following.
・２− （２’−ヒドロキシ−３′−ｔ−ブチル−５′
−メチルフェニル）−５−クロロ−ベンゾトリアゾール
・２，２′−ヒドロキシ−４，４′−ジメトキシベンゾ
フェノン
・ビス（５−ベンゾイル−４−ヒドロキシ−２−メトキ
シフェニル）メタン
これら化合物は１種または２種以上混合して使用するこ
とかできる。添加量は特に制限ないが、好ましくは使用
繊維の重量に対して０．５〜８．０％重量比である。こ
れらの紫外線吸収剤は常法により微粒子化処理を施した
上で必要により染浴に添加される。・2-(2'-hydroxy-3'-t-butyl-5'
-methylphenyl)-5-chloro-benzotriazole, 2,2'-hydroxy-4,4'-dimethoxybenzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane. It is possible to use a mixture of more than one species. The amount added is not particularly limited, but it is preferably 0.5 to 8.0% by weight based on the weight of the fibers used. These ultraviolet absorbers are micronized by a conventional method and then added to the dye bath if necessary.
本発明において、染色方法はそれ自体公知の方法に従っ
て行うことができる。例えばポリエステル繊維を染色す
る場合は、先ず、必要な濃度か得ることのできる量の本
発明の分散染料組成物と必要に応じて紫外線吸収剤を加
えた染色浴に酢酸または酢酸と酢酸ナトリウムからなる
ｐＨ緩衝水溶液てそのｐＨを４〜７に調整する。必要に
応じて若干量の公知の金属イオン封鎖剤、均染剤などを
染浴に加えた後、被染物を投入し、攪拌しなから染浴の
温度を徐々に昇温しくたとえば１分間に１〜３°Ｃ）、
１００°Ｃ以上の所定の温度（たとえば１１０〜１４０
’Ｃ）で通常３０〜９０分間染色する。この染色時間は
染着の状態により短縮することか出来る。浴比は通常１
：３０〜１：５０が採用される。文武（１）〜式（４）
の化合物をそれぞれ微粒子化処理して得た染料を前記し
たような割合で、水に直接加えて染色浴を調製し、以下
前記と同様にして染色を行うことも出来る。染色終了後
、冷却し、水洗し、必要に応じて還元洗浄し、水洗、乾
燥して仕上げる。In the present invention, the dyeing method can be carried out according to a method known per se. For example, when dyeing polyester fibers, first, a dye bath consisting of acetic acid or acetic acid and sodium acetate is added to a dye bath containing the disperse dye composition of the present invention in the required concentration or amount that can be obtained, and an ultraviolet absorber if necessary. Adjust the pH to 4-7 using a pH buffer aqueous solution. After adding a small amount of a known sequestering agent, leveling agent, etc. to the dye bath as necessary, the object to be dyed is put in, and the temperature of the dye bath is gradually increased, for example, for 1 minute, while stirring. 1-3°C),
A predetermined temperature of 100°C or higher (e.g. 110-140°C)
'C) is usually stained for 30 to 90 minutes. This dyeing time can be shortened depending on the state of dyeing. The bath ratio is usually 1
:30 to 1:50 is adopted. Literature (1) to expression (4)
It is also possible to prepare a dyeing bath by directly adding dyes obtained by micronizing each of the above compounds to water in the proportions described above, and then carry out the dyeing in the same manner as above. After dyeing, it is cooled, washed with water, reduced if necessary, washed with water, and dried to finish.
また捺染の場合は、微粒子化された染料の分散液を公知
の糊と共に練り合わせ、これを布に印捺、乾燥した後、
スチーミング又は乾熱処理を行う。In the case of textile printing, a finely divided dye dispersion is kneaded with a known paste, printed on cloth, dried, and then
Perform steaming or dry heat treatment.
この場合、使用する紫外線吸収剤はベンゾフェノン系の
ものが好ましい。本発明において疎水性繊維としてはポ
リエステル繊維、アセテート繊維か挙げられるが好まし
いものはポリエステル繊維である。In this case, the ultraviolet absorber used is preferably a benzophenone type. In the present invention, hydrophobic fibers include polyester fibers and acetate fibers, but polyester fibers are preferred.
実施例
以下、実施例によって本発明を具体的に説明下る。文中
、部、％はそれぞれ重量部、重量％を意味する。EXAMPLES Hereinafter, the present invention will be specifically explained using examples. In the text, parts and % mean parts by weight and % by weight, respectively.
微粒子化例１
前記式（５）、（６）、（７）、（８）、（９）、００
）及びｏｌ）で示される染料原末の各々につきその１５
部、チモールＮ２０部（花王製分散剤）チモールＣ１５
部（花王製分散剤）及び水８０部を別々に混合し、サン
ドグラインダーを用いて最大径５μ以下になる迄微粒子
化し、乾燥することにより、各々の染料の微粒子化物を
得た。Micronization Example 1 Formulas (5), (6), (7), (8), (9), 00
) and ol) for each of the dyestuff powders shown in 15
part, Thymol N20 parts (Kao dispersant) Thymol C15
(a dispersant made by Kao) and 80 parts of water were mixed separately, and the mixture was made into fine particles using a sand grinder until the maximum diameter was 5 μm or less, and dried to obtain fine particles of each dye.
微粒子化例２
下記式０２式Ｇ３および弐〇４）で示す紫外線吸収剤に
つき、各々の原体３０部、チモールＮ２０部（花王製分
散剤）、チモールＣ１０部（花王製分散剤）および水４
０部を別々に混合し、サンドグラインダーを用いて最大
径５μ以下になるよう微粒子化し、各々の液状の微粒子
化紫外線吸収剤を得た。Micronization Example 2 For the ultraviolet absorbers shown by the following formulas 02, G3 and 204), 30 parts of each active ingredient, 20 parts of thymol N (dispersant manufactured by Kao), 10 parts of thymol C (dispersant manufactured by Kao) and 4 parts of water.
0 parts were mixed separately and micronized using a sand grinder to a maximum diameter of 5 μm or less to obtain each liquid micronized ultraviolet absorber.
ＣＨ。CH.
微粒子化例３
前記式（６）で示される染料（原末）を１．５部、同じ
く式（７）を４．５部、式（８）を４．５部、式（９）
を４．５部、モデールＮ（前記と同じ）を２０部、デモ
ールＣ（前記と同じ）を１５部及び水８０部を混合し、
微粒子化例１と同様に処理し、微粒子化物を得た。Microparticulation Example 3 1.5 parts of the dye (base powder) represented by the formula (6), 4.5 parts of the formula (7), 4.5 parts of the formula (8), and the formula (9)
Mix 4.5 parts of Model N (same as above), 20 parts of Model C (same as above), 15 parts of Demol C (same as above) and 80 parts of water,
It was treated in the same manner as in Micronization Example 1 to obtain a micronized product.
実施例１
微粒子化例１て調製した式（５）を１．３４部、式（６
）を０．１５部、式（７）を０．５部、式（８）を０．
５部、式（９）を０．５部、式α０）を０．６部、式０
１）を０．６部及び微粒子化例２で調製した式ａりの紫
外線吸収剤２部を含有する３０００部の染料分散液の染
浴をつくり、酢酸と酢酸ナトリウムによりそのｐＨを５
に調整する。染浴にポリエステル繊維布１００部を投入
し、６０’Ｃから１分間毎に１°Ｃの割合で昇温し、１
３０ ’Ｃて６０分間染色し、通常の方法で還元、洗浄
し、乾燥する。Example 1 1.34 parts of formula (5) prepared in Micronization Example 1, 1.34 parts of formula (6)
), 0.5 parts of formula (7), and 0.5 parts of formula (8).
5 parts, 0.5 parts of formula (9), 0.6 parts of formula α0), formula 0
A dye bath of 3,000 parts of a dye dispersion containing 0.6 parts of 1) and 2 parts of the UV absorber of formula a prepared in Micronization Example 2 was prepared, and the pH was adjusted to 5 with acetic acid and sodium acetate.
Adjust to. 100 parts of polyester fiber cloth was put into a dye bath, and the temperature was raised from 60'C at a rate of 1°C every minute.
Stain for 60 minutes at 30'C, reduce, wash and dry in the usual manner.
得られた染色布はエンジ色であり、その耐光堅牢度は優
秀であった。尚耐光堅牢度は次の方法により行った。The dyed fabric obtained was dark red and had excellent light fastness. The light fastness was measured by the following method.
染色物にウレタンフオームを裏打ちしたものにフニード
メーター（ブラックパネル温度８３°Ｃ±３°Ｃ１３０
０時間）カーボンアーク灯を用いて照射し照射部分の変
褪色をＪＩＳ Ｌ−０８０４の経褪色用グレースケール
にて判定した。A funied meter (black panel temperature 83°C ± 3°C 130
(0 hour) irradiation was performed using a carbon arc lamp, and the discoloration and fading of the irradiated area was determined using the JIS L-0804 gray scale for fading over time.
実施例２
実施例１において、紫外線吸収剤を省いて実施例１と同
等に染色処理しエンジ色の染色物を得た。Example 2 A dyeing process was carried out in the same manner as in Example 1 except that the ultraviolet absorber was omitted to obtain a dark red dyed product.
その耐光堅牢度は優れていた。Its light fastness was excellent.
実施例３
微粒子化例３て調製した微粒子化染料を１．６５部、式
（５）を１．３４部、弐α０）を０．６部、式０υを０
．６部及び前記式Ｏｚの紫外線吸収剤微粒子化物２部を
含有する３０００部の染料分散液の染浴をつくり実施例
１と同様にしてポリエステル布を染色した。染色物はエ
ンジ色を呈し、その耐光堅牢度は優れていた。Example 3 1.65 parts of the micronized dye prepared in Micronization Example 3, 1.34 parts of formula (5), 0.6 parts of 2α0), and 0 of the formula 0υ
．． A dye bath of 3,000 parts of a dye dispersion containing 6 parts and 2 parts of a micronized ultraviolet absorber of the formula Oz was prepared, and a polyester cloth was dyed in the same manner as in Example 1. The dyed product exhibited a dark red color and had excellent light fastness.
実施例４
微粒子化例１で調製した式（５）を１．３４部、式（６
）を０．１５部、式（７）を０．７５部、式（８）を０
．７５部、及び前記式〇３の紫外線吸収剤微粒子化物２
部を含有する３０００部の染料分散液の染浴をつくり、
実施例１と同様にしてポリエステル布を染色した。染色
物はエンジ色を呈し、その耐光堅牢度は優れていた。Example 4 1.34 parts of formula (5) prepared in Micronization Example 1 and formula (6
) 0.15 parts, formula (7) 0.75 parts, formula (8) 0
．． 75 parts, and ultraviolet absorber micronized product 2 of the above formula 03
A dye bath of 3000 parts of dye dispersion containing
A polyester cloth was dyed in the same manner as in Example 1. The dyed product exhibited a dark red color and had excellent light fastness.
実施例５
微粒子化例１で調製した式（６）を０．０６部、同じく
式（７）を０．２部、式（８）を０．２部、式（９）を
０．２部及び微粒子化例２て調製した弐〇４）の紫外線
吸収剤４部を含有する３０００部の染料分散液の染浴を
つくり、酢酸と酢酸ナトリウムによりそのｐＨを５に調
製する。染浴にポリエステル繊維布１００部を投入し、
実施例１と同様にして染色した。得られた染色布は赤色
を呈し、その耐光堅牢度は優れていた。Example 5 0.06 parts of formula (6) prepared in Micronization Example 1, 0.2 parts of formula (7), 0.2 parts of formula (8), and 0.2 parts of formula (9) A dye bath containing 3,000 parts of the dye dispersion containing 4 parts of the ultraviolet absorber 204) prepared in Micronization Example 2 was prepared, and its pH was adjusted to 5 with acetic acid and sodium acetate. Add 100 parts of polyester fiber cloth to the dye bath,
It was dyed in the same manner as in Example 1. The dyed cloth obtained had a red color and excellent light fastness.
実施例６
微粒子化例１で調製した式（５）を１．３４部、式（６
）を０．１５部、式（８）を１．５部、弐αＯ）を０．
６部及び式０１）を０．６部を含有する３０００部の染
料分散液を染浴をつくり実施例１と同様にしてポリエス
テル布を染色した。染色物はエンジ色を呈し、その耐光
堅牢度は優れていた。Example 6 1.34 parts of formula (5) prepared in Micronization Example 1, formula (6
) is 0.15 parts, formula (8) is 1.5 parts, and 2αO) is 0.15 parts.
A dye bath was prepared with 3000 parts of a dye dispersion containing 0.6 parts of formula 01) and 0.6 parts of formula 01), and a polyester fabric was dyed in the same manner as in Example 1. The dyed product exhibited a dark red color and had excellent light fastness.
実施例７〜１６
実施例１中の式（６）の代わりに表２に示す染料を用い
て他は実施例１と同様に染色し、エンジ色の染色物を得
た。この染色物の耐光堅牢度は優れていた。Examples 7 to 16 Dyeing was carried out in the same manner as in Example 1, except that the dye shown in Table 2 was used in place of the formula (6) in Example 1, to obtain an orange dyed product. The light fastness of this dyeing was excellent.
実施例１８〜２９
実施例１中の式（７）の代わりに表３に示す染料を用い
て他の実施例１と同様に染色し、エンジ色の染色物を得
た。このものの耐光堅牢度は優れていた。Examples 18 to 29 Dyeing was carried out in the same manner as in Example 1 except that the dye shown in Table 3 was used in place of the formula (7) in Example 1 to obtain a dark red dyed product. This product had excellent light fastness.
発明の効果
高耐光堅牢度を有しつつカラーバリユーのある、経済的
効果の高い染色法が確立された。Effects of the Invention An economically effective dyeing method that has high light fastness and color value has been established.
特許出願人 日本化薬株式会社Patent applicant: Nippon Kayaku Co., Ltd.
Claims (1)
物と式（２）、式（３）及び式（４）からなる群から選
ばれる少くとも１種以上の化合物よりなる分散染料組成
物。 式（１）： ▲数式、化学式、表等があります▼（１） （式中、Ｘは塩素原子又はシアノ基を、Ｙは水素原子、
塩素原子、メチル基又はアセチルアミノ基を、Ｒ＾１、
Ｒ＾２はそれぞれ独立に、水素原子、シアノエチル基、
アセトキシエチル基、低級アルコキシ（Ｃ＿１〜＿４）
エトキシエチル基、低級アルコキシカルボニルオキシエ
チル基又はヒドロキシアルキル基を、 Ｚは水素原子又は塩素原子をそれぞれ表す。）式（２）
： ▲数式、化学式、表等があります▼（２） （式中、Ｒ＾３は水酸基、フェノキシ基又はフェニル基
で置換されたアルキル（Ｃ＿１〜＿６）基を表す。） 式（３）： ▲数式、化学式、表等があります▼（３） （式中、Ｒ＾４は水素原子、水酸基、アルキルカルボニ
ルアルコキシ基、アルコキシカルボニルアルコキシ基、
アルコキシカルボニルアルキル基、アルコキシアルキル
アミノスルホニル基、又はアシルオキシ基を、Ｒ＾５は
水素原子又はメチル基をそれぞれ表す。） 式（４）： ▲数式、化学式、表等があります▼（４） ２、特許請求の範囲第１項に記載の分散染料組成物を用
いることを特徴とする疎水性繊維の染色法。 ３、特許請求の範囲第１項に記載の式（１）で示される
少く共１種以上の化合物と式（２）、式（３）、式（４
）からなる群から選ばれる少く共１種以上の化合物を用
いることを特徴とする疎水性繊維の染色法。[Claims] 1. At least one compound represented by the following formula (1) and at least one compound selected from the group consisting of formula (2), formula (3), and formula (4). A disperse dye composition consisting of a compound of Formula (1): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the formula, X is a chlorine atom or a cyano group, Y is a hydrogen atom,
A chlorine atom, methyl group or acetylamino group, R^1,
R^2 each independently represents a hydrogen atom, a cyanoethyl group,
Acetoxyethyl group, lower alkoxy (C_1-_4)
Z represents an ethoxyethyl group, a lower alkoxycarbonyloxyethyl group, or a hydroxyalkyl group, and Z represents a hydrogen atom or a chlorine atom, respectively. ) formula (2)
: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) (In the formula, R^3 represents an alkyl (C_1-_6) group substituted with a hydroxyl group, phenoxy group, or phenyl group.) Formula (3): ▲ There are mathematical formulas, chemical formulas, tables, etc.▼(3) (In the formula, R^4 is a hydrogen atom, a hydroxyl group, an alkylcarbonylalkoxy group, an alkoxycarbonylalkoxy group,
R^5 represents an alkoxycarbonylalkyl group, an alkoxyalkylaminosulfonyl group, or an acyloxy group, and R^5 represents a hydrogen atom or a methyl group, respectively. ) Formula (4): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (4) 2. A method for dyeing hydrophobic fibers, characterized by using the disperse dye composition according to claim 1. 3. At least one or more compounds represented by formula (1) according to claim 1 and formula (2), formula (3), or formula (4)
) A method for dyeing hydrophobic fibers, characterized by using at least one compound selected from the group consisting of:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2299841A JPH04173875A (en) | 1990-11-07 | 1990-11-07 | Disperse dye composition and method for dyeing hydrophobic fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2299841A JPH04173875A (en) | 1990-11-07 | 1990-11-07 | Disperse dye composition and method for dyeing hydrophobic fiber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04173875A true JPH04173875A (en) | 1992-06-22 |
Family
ID=17877576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2299841A Pending JPH04173875A (en) | 1990-11-07 | 1990-11-07 | Disperse dye composition and method for dyeing hydrophobic fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04173875A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1477531A1 (en) * | 2003-05-14 | 2004-11-17 | DyStar Textilfarben GmbH & Co. Deutschland KG | Disperse dye mixtures |
| JP2006225497A (en) * | 2005-02-17 | 2006-08-31 | Sumitomo Chemical Co Ltd | Red-based disperse dye composition and application of the same composition to hydrophobic fiber material |
| JP2006257377A (en) * | 2005-02-15 | 2006-09-28 | Sumitomo Chemical Co Ltd | Disperse dye composition and application thereof to hydrophobic fibrous material |
| JP2010126853A (en) * | 2008-11-28 | 2010-06-10 | Teijin Fibers Ltd | Method for producing dyed cloth and dyed cloth |
| CN107286703A (en) * | 2017-05-26 | 2017-10-24 | 杭州吉华江东化工有限公司 | A kind of high Exposure to Sunlight dispersed black dye mixture and its application |
-
1990
- 1990-11-07 JP JP2299841A patent/JPH04173875A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1477531A1 (en) * | 2003-05-14 | 2004-11-17 | DyStar Textilfarben GmbH & Co. Deutschland KG | Disperse dye mixtures |
| US7101408B2 (en) | 2003-05-14 | 2006-09-05 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Disperse dye mixtures |
| JP2006257377A (en) * | 2005-02-15 | 2006-09-28 | Sumitomo Chemical Co Ltd | Disperse dye composition and application thereof to hydrophobic fibrous material |
| JP4617997B2 (en) * | 2005-02-15 | 2011-01-26 | 住友化学株式会社 | Disperse dye composition and application to hydrophobic fiber material |
| JP2006225497A (en) * | 2005-02-17 | 2006-08-31 | Sumitomo Chemical Co Ltd | Red-based disperse dye composition and application of the same composition to hydrophobic fiber material |
| JP4617914B2 (en) * | 2005-02-17 | 2011-01-26 | 住友化学株式会社 | Red disperse dye composition and application to hydrophobic fiber materials |
| JP2010126853A (en) * | 2008-11-28 | 2010-06-10 | Teijin Fibers Ltd | Method for producing dyed cloth and dyed cloth |
| CN107286703A (en) * | 2017-05-26 | 2017-10-24 | 杭州吉华江东化工有限公司 | A kind of high Exposure to Sunlight dispersed black dye mixture and its application |
| CN107286703B (en) * | 2017-05-26 | 2019-08-20 | 杭州吉华江东化工有限公司 | A kind of high solarization dispersed black dye mixture and its application |
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