JPH0674387B2 - Dye dispersion - Google Patents
Dye dispersionInfo
- Publication number
- JPH0674387B2 JPH0674387B2 JP2052700A JP5270090A JPH0674387B2 JP H0674387 B2 JPH0674387 B2 JP H0674387B2 JP 2052700 A JP2052700 A JP 2052700A JP 5270090 A JP5270090 A JP 5270090A JP H0674387 B2 JPH0674387 B2 JP H0674387B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- mol
- dispersant
- dye dispersion
- 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.)
- Expired - Fee Related
Links
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- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Coloring (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は染料分散物に関するものであり、特に高温分散
性に優れ、しかも汚染性，還元退色性に優れた分散剤を
含有する染料分散物に関する。TECHNICAL FIELD The present invention relates to a dye dispersion, and in particular, a dye dispersion containing a dispersant having excellent high temperature dispersibility, stain resistance and reduction fading property. Regarding
従来からポリエステル繊維等の染色に主として分散染料
が使用されている。これは分散染料の染料自身は、水に
不溶、あるいは難溶であるため、分散剤を用いて水に安
定に分散できるよにしたものである。Conventionally, disperse dyes have been mainly used for dyeing polyester fibers and the like. This is because the disperse dye itself is insoluble or hardly soluble in water, so that it can be stably dispersed in water by using a dispersant.
この場合の分散剤として主としてリグニンスルホン酸や
ナフタレンスルホン酸ホルマリン縮合物等が使用されて
きた。In this case, as the dispersant, ligninsulfonic acid or naphthalenesulfonic acid formalin condensate has been mainly used.
リグニンスルホン酸は高温分散性に優れ、ポリエステル
繊維等の染色時のような高温域でも良好な分散性を示
す。しかしながら布を汚染する傾向があり、またリグニ
ンスルホン酸の構成成分中に染料を還元してしまうもの
が存在し色の退色が起きる場合がある。Lignin sulfonic acid has excellent high-temperature dispersibility and exhibits good dispersibility even in a high temperature range such as when dyeing polyester fibers. However, there is a tendency to stain the cloth, and there are cases in which the components of the lignin sulfonic acid that reduce the dye are present and color fading occurs.
また、ナフタレンスルホン酸ホルマリン縮合物は、常温
域での汚染性は少なくまた還元退色も起こさない。しか
し高温分散性については問題があり高温域では分散性が
極度に低下する。In addition, the naphthalene sulfonic acid formalin condensate has little contamination in the normal temperature range and does not cause reductive discoloration. However, there is a problem with high temperature dispersibility, and the dispersibility is extremely reduced in the high temperature range.
このように高温分散性，汚染性，還元退色性のいずれか
において不充分であった。As described above, the dispersibility at high temperature, the staining property, and the reduction fading property were insufficient.
そこで本発明者は高温域においても優れた分散性を示
し、しかも布に対して汚染することが無く、また還元退
色を起こすことの無い染料分散物について鋭意検討の結
果、本発明に到達したものである。Therefore, the present inventor has achieved the present invention as a result of extensive studies on a dye dispersion that exhibits excellent dispersibility even in a high temperature range, does not stain the cloth, and does not cause reduction fading. Is.
すなわち、 一般式（Ｉ） ［式中Ｘは または−Ｏ− のいずれかを示す（但し、ｎは１から５の整数、Ｒ１,R
３は夫々独立して水素、またはアルキル基、Ｒ２はアル
キル基、Ｒ４はアルキレン基を示す）］ で示される化合物の１種、または２種以上と、亜硫酸塩
（次亜硫酸塩、ピロ亜硫酸塩を含む）、及びアルデヒド
類とを、必要に応じてアルカリの存在下、任意の順序で
反応させて得られる縮合成生物を分散剤として含有する
ことを特徴とする染料分散物 を提供するものである。That is, the general formula (I) [Where X is Or one of -O- (where n is an integer of 1 to 5, R 1 , R
3 each independently represent hydrogen or an alkyl group, R 2 represents an alkyl group, and R 4 represents an alkylene group)], and one or more compounds of sulfite (hyposulfite, pyrosulfite). And a aldehyde, if necessary, in the presence of an alkali, in any order, to produce a polydisperse product as a dispersant, a dye dispersion characterized by containing a condensed synthetic product. Is.
本発明に用いる一般式（Ｉ）で表わされる化合物として
は、2,2−ビス（４−ヒドロキシフェニル）プロパン,4,
4′−ジヒドロキシジフェニルスルホン,4,4′−ジヒド
ロキシビフェニル,4,4−ビス（４−ヒドロキシフェニ
ル）吉草酸が好んで用いられ、またこれらを組み合わせ
て用いることもできる。また亜硫酸塩としては、亜硫酸
ナトリウム，亜硫酸水素ナトリウム，ピロ亜硫酸ナトリ
ウム等があげられ，アルデヒド類としてはホルムアルデ
ヒドが一般的である。さらにアルカリとしては水酸化ナ
トリウム，アンモニア及びアンモニウム基の水酸化物等
があげられる。Examples of the compound represented by the general formula (I) used in the present invention include 2,2-bis (4-hydroxyphenyl) propane, 4,
4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxybiphenyl, 4,4-bis (4-hydroxyphenyl) valeric acid are preferably used, and these can also be used in combination. Further, examples of the sulfite include sodium sulfite, sodium hydrogen sulfite, sodium pyrosulfite, etc., and formaldehyde is generally used as the aldehyde. Further, examples of the alkali include sodium hydroxide, ammonia, and ammonium group hydroxide.
その使用割合は一般式（Ｉ）で表される化合物１モルに
対して亜硫酸塩0.2モル〜３モル、アルデヒド類として
ホルムアルデヒドを用いる場合には0.2モルから４モル
が好ましい。また反応液pHは10〜13であることが好まし
く、必要に応じてアルカリを用いて調整すればよい。The use ratio thereof is preferably 0.2 mol to 3 mol of sulfite with respect to 1 mol of the compound represented by the general formula (I), and when formaldehyde is used as the aldehyde, 0.2 mol to 4 mol is preferable. The pH of the reaction solution is preferably 10 to 13, and may be adjusted with an alkali as necessary.
これらの縮合反応の条件は、常圧ないしは加圧下に温度
30〜140℃で通常１〜30時間で行う。The conditions for these condensation reactions are atmospheric pressure or pressure under temperature.
It is usually carried out at 30 to 140 ° C for 1 to 30 hours.
なお本発明の方法によって得られる分散剤は、単独使用
だけでなく、ナフタレンスルホン酸ホルマリン縮合物，
リグニンスルホン酸，その他公知の界面活性剤と併用使
用することができる。The dispersant obtained by the method of the present invention can be used not only alone but also with a naphthalenesulfonic acid formalin condensate,
It can be used in combination with ligninsulfonic acid and other known surfactants.
以下、実施例および比較例によって本発明を詳細に説明
する。なお、実施例および比較例中の部はいずれも重量
部を示している。Hereinafter, the present invention will be described in detail with reference to Examples and Comparative Examples. All parts in Examples and Comparative Examples are parts by weight.
［分散剤の合成実施例］ 合成例(1) 2,2−ビス（４−ヒドロキシフェニル）プロパン228.3部
（１モル）と亜硫酸ナトリウム126.3部（１モル）を水8
26部に加えた。この固液に温度90℃にて37％ホルマリン
243.3部（ホルムアルデヒド ３モル）を１時間で滴下
した。これを温度100℃に昇温し10時間反応させた。こ
の後、冷却して分散剤の水溶液を得た。Synthesis Example of Dispersant Synthesis Example (1) 228.3 parts (1 mol) of 2,2-bis (4-hydroxyphenyl) propane and 126.3 parts (1 mol) of sodium sulfite were added to 8 parts of water.
Added to 26 parts. Add 37% formalin to this solid-liquid at 90 ° C.
243.3 parts (formaldehyde 3 mol) was added dropwise over 1 hour. This was heated to a temperature of 100 ° C. and reacted for 10 hours. Then, it cooled and the aqueous solution of the dispersant was obtained.
合成例(2)〜(6) 合成例(1)の2,2−ビス（４−ヒドロキシフェニル）プロ
パンを第１表記載の化合物に変える他はモル比等同様に
して合成例(2)〜(6)を得た。Synthetic Examples (2) to (6) Synthetic Examples (2) to (6) except that the 2,2-bis (4-hydroxyphenyl) propane of Synthetic Example (1) is replaced by the compound shown in Table 1. I got (6).
合成例(7) 4,4′−ジヒドロキシジフェニルスルホン175.2部（0.7
モル）と、4,4′−ジヒドロキシビフェニル55.9部（0.3
モル）と亜硫酸ナトリウム126.3部（１モル）を水834部
に加えた。この固液に温度80℃にて37％ホルマリン243.
3部（３モル）を１時間で滴下した。これを温度90℃に
昇温し10時間反応させた。この後、冷却して分散剤の水
溶液を得た。 Synthesis example (7) 4,4'-dihydroxydiphenyl sulfone 175.2 parts (0.7
Mol) and 5,4 parts of 4,4'-dihydroxybiphenyl (0.3
Mol) and 126.3 parts (1 mol) of sodium sulfite were added to 834 parts of water. 37% formalin 243.
3 parts (3 mol) was added dropwise over 1 hour. This was heated to a temperature of 90 ° C. and reacted for 10 hours. Then, it cooled and the aqueous solution of the dispersant was obtained.
［分散剤の合成比較例］ 合成例(8) 2,2−ビス（４−ヒドロキシフェニル）プロパン171.3部
（0.75モル）と、ｍ−クレゾール27.0部（0.25モル）と
亜硫酸ナトリウム126.3部（１モル）を水757部に加え
た。この固液に温度80℃にて37％ホルマリン202.7部
（2.5モル）を１時間で滴下した。これを温度90℃に昇
温し15時間反応させた。この後、冷却して分散剤の水溶
液を得た。[Comparative Example of Synthesis of Dispersant] Synthesis Example (8) 171.3 parts (0.75 mol) of 2,2-bis (4-hydroxyphenyl) propane, 27.0 parts (0.25 mol) of m-cresol and 126.3 parts (1 mol of sodium sulfite). ) Was added to 757 parts of water. 202.7 parts (2.5 mol) of 37% formalin was added dropwise to this solid liquid at a temperature of 80 ° C. over 1 hour. This was heated to a temperature of 90 ° C. and reacted for 15 hours. Then, it cooled and the aqueous solution of the dispersant was obtained.
合成例(9) 2,2−ビス（４−ヒドロキシフェニル）プロパン171.3部
（0.75モル）と、シェファー酸56.1部（0.25モル）と亜
硫酸ナトリウム94.7部（0.75モル）を水752部に加え
た。この固液を水酸化ナトリウム水溶液でpH12にに調整
後、温度80℃にて37％ホルマリン202.7部（2.5モル）を
１時間で滴下した。これを温度90℃に昇温し15時間反応
させた。この後、冷却して分散剤の水溶液を得た。Synthesis example (9) 171.3 parts (0.75 mol) of 2,2-bis (4-hydroxyphenyl) propane, 56.1 parts (0.25 mol) of shefferic acid and 94.7 parts (0.75 mol) of sodium sulfite were added to 752 parts of water. This solid-liquid was adjusted to pH 12 with an aqueous sodium hydroxide solution, and 202.7 parts (2.5 mol) of 37% formalin was added dropwise at a temperature of 80 ° C over 1 hour. This was heated to a temperature of 90 ° C. and reacted for 15 hours. Then, it cooled and the aqueous solution of the dispersant was obtained.
合成例(10) 2,2−ビス（４−ヒドロキシフェニル）プロパン171.3部
（0.75モル）と、メチルナフタレンスルホン酸35.6部
（0.25モル）と亜硫酸ナトリウム94.7部（0.75モル）を
水704部に加えた。この固液を水酸化ナトリウム水溶液
でpH12に調整後、温度40℃にて37％ホルマリン202.7部
（2.5モル）を１時間で滴下した。これを温度90℃に昇
温し15時間反応させた。この後、冷却して分散剤の水溶
液を得た。Synthesis example (10) 2,2-bis (4-hydroxyphenyl) propane 171.3 parts (0.75 mol), methylnaphthalenesulfonic acid 35.6 parts (0.25 mol) and sodium sulfite 94.7 parts (0.75 mol) were added to water 704 parts. It was The solid-liquid was adjusted to pH 12 with an aqueous sodium hydroxide solution, and 202.7 parts (2.5 mol) of 37% formalin was added dropwise at a temperature of 40 ° C over 1 hour. This was heated to a temperature of 90 ° C. and reacted for 15 hours. Then, it cooled and the aqueous solution of the dispersant was obtained.
実施例１ 合成例(1)〜(10)の縮合物水溶液をスプレードライヤー
で粉末化し、粉末化した試料の布への汚染性の試験を行
った。また比較サンプルとして、ナフタレンスルホン酸
ホルマリン低縮合物（以下NSFと略）、部分脱スルホン
リグニンスルホン酸（以下LIGと略）の汚染性試験を同
時に行った。Example 1 The aqueous condensate solutions of Synthesis Examples (1) to (10) were powdered with a spray dryer, and the powdered sample was tested for stain resistance on cloth. In addition, as a comparative sample, a naphthalene sulfonic acid formalin low condensate (hereinafter abbreviated as NSF) and a partially desulfurized lignin sulfonic acid (hereinafter abbreviated as LIG) were simultaneously tested for contamination.
汚染性の試験は以下の通りである。The stainability test is as follows.
分散剤660mg（絶乾量）を水に溶解し酢酸を用いてpH5.0
に調整した後、全量を250mlにする。8gの試験布と共
に、染色試験機に仕込み105℃にて１時間染色操作を行
った後、試験布を乾燥し、白色度を測定する。得られた
結果第２表に示した。Dispersing 660 mg (absolute dry weight) of dispersant in water and pH 5.0 using acetic acid
After adjusting to, make the total volume 250 ml. Along with 8 g of the test cloth, it is placed in a dyeing tester and dyed at 105 ° C. for 1 hour, and then the test cloth is dried to measure the whiteness. The obtained results are shown in Table 2.
実施例２ 合成例(1)〜(10)の縮合物水溶液をスプレードライヤー
で粉末化したもの、及び比較サンプルとしてNSF,LIGの
高温分散性の比較を行った。 Example 2 The high temperature dispersibility of the condensate aqueous solutions of Synthesis Examples (1) to (10) powdered with a spray dryer and NSF and LIG as a comparative sample were compared.
試験法は以下の通りである。The test method is as follows.
染料，分散剤、及び水を所定量混合し、微粒化後ろ過
し、スプレードライで乾燥した（入口温度100〜150℃、
出口温度50〜55℃）。Dye, dispersant, and water were mixed in a predetermined amount, atomized, filtered, and dried by spray drying (inlet temperature 100-150 ° C,
Outlet temperature 50-55 ℃).
その後、スペック試験、及び熱処理後（80℃,15hr.）、
スペック試験を行った。After that, after the specification test and heat treatment (80 ℃, 15hr.),
A spec test was conducted.
結果を第３表に示した。The results are shown in Table 3.
実施例３ 合成例(1)〜(10)の縮合物水溶液をスプレードライヤー
で粉末化したもの、及び比較サンプルとしてNSF,LIGの
還元退色性試験を行った。 Example 3 An aqueous solution of the condensate obtained in Synthesis Examples (1) to (10) was pulverized with a spray drier, and NSF and LIG reduction fading tests were conducted as comparative samples.
還元退色性の試験は以下の通りである。The test of reductive fading is as follows.
染料原体と、分散剤（染料原体に対し400％）に水を加
え酢酸を用いてpH5.0に調整した後、全量を250mlにす
る。8gの試験布と共に染色試験機に仕込み130℃にて１
時間染色した後、試験布を乾燥し還元退色の比較を行っ
た。Water is added to the dye base and the dispersant (400% based on the dye base), and the pH is adjusted to 5.0 with acetic acid, and then the total amount is set to 250 ml. Prepared in a dyeing tester together with 8g of test cloth, 1 at 130 ℃
After dyeing for a period of time, the test cloth was dried and the reduction fading was compared.
結果を第４表に示した。The results are shown in Table 4.
第１表，第２表，第３表の結果から本発明の染料分散物
が、高温分散性、汚染性、還元退色性に優れることがわ
かる。 From the results shown in Tables 1, 2 and 3, it can be seen that the dye dispersion of the present invention is excellent in high temperature dispersibility, stain resistance and reduction fading.
本発明の方法によって得られる分散剤を含有する染料分
散物は下記の効果を有する。The dye dispersion containing the dispersant obtained by the method of the present invention has the following effects.
・染色時の高い温度域でも優れた分散性を示し、ターリ
ング，染めむら等の障害が起こらない。・ It shows excellent dispersibility even in high temperature range during dyeing and does not cause problems such as tarring and uneven dyeing.
・ポリエステル繊維や木綿の汚染が少なく、淡色の染色
時においても優れた効果を示す。-There is little contamination of polyester fibers and cotton, and it has an excellent effect even when dyeing light colors.
・染料自体を還元し色をあせさせることが少ない。・ Reduces the color by reducing the dye itself.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 中本 奉文 山口県岩国市飯田町２―８―１ 山陽国策 パルプ株式会社生産技術研究所内 (56)参考文献 特開 昭60−141767（ＪＰ，Ａ) 特開 昭56−50915（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Fumifumi Nakamoto 2-8-1 Iida-cho, Iwakuni-shi, Yamaguchi Inside Sanyo Kokusaku Pulp Co., Ltd. (56) Reference JP-A-60-141767 (JP, A) ) JP-A-56-50915 (JP, A)
Claims (2)
３は夫々独立して水素、またはアルキル基、Ｒ２はアル
キル基、Ｒ４はアルキレン基を示す）］ で示される化合物の１種、または２種以上と、亜硫酸
塩、及びアルデヒド類とを、必要に応じてアルカリの存
在下、任意の順序で反応させて得られる縮合成生物を分
散剤として含有することを特徴とする染料分散物。1. A general formula (I) [Where X is Or one of -O- (where n is an integer of 1 to 5, R 1 , R
3 each independently represents hydrogen or an alkyl group, R 2 represents an alkyl group, and R 4 represents an alkylene group)], and a sulfite salt and an aldehyde, A dye dispersion comprising, as a dispersant, a polycondensation product obtained by reacting in an arbitrary order in the presence of an alkali, if necessary.
（II）で表される 2,2−ビス（４−ヒドロキシフェニル）プロパンである
請求項１記載の染料分散物。2. A compound represented by the general formula (I) is represented by the general formula (II). The dye dispersion according to claim 1, which is 2,2-bis (4-hydroxyphenyl) propane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2052700A JPH0674387B2 (en) | 1990-03-06 | 1990-03-06 | Dye dispersion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2052700A JPH0674387B2 (en) | 1990-03-06 | 1990-03-06 | Dye dispersion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03255119A JPH03255119A (en) | 1991-11-14 |
| JPH0674387B2 true JPH0674387B2 (en) | 1994-09-21 |
Family
ID=12922168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2052700A Expired - Fee Related JPH0674387B2 (en) | 1990-03-06 | 1990-03-06 | Dye dispersion |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0674387B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007524747A (en) * | 2004-02-25 | 2007-08-30 | ビーエーエスエフ アクチェンゲゼルシャフト | Method for producing a polymer powder that is well redispersible in water |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100514199C (en) * | 2003-01-23 | 2009-07-15 | 藤仓化成株式会社 | Negative charge controlling agent and static charge image developing toner using the same, and method for producing the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2937875A1 (en) * | 1979-09-19 | 1981-04-02 | Bayer Ag, 5090 Leverkusen | Condensate from phenol mixt., formaldehyde, bi:sulphite - and opt. nitrogen cpd., used esp. as dispersant in high temp. dyeing |
| JPS60141767A (en) * | 1983-12-29 | 1985-07-26 | Sumitomo Chem Co Ltd | Dye dispersion |
-
1990
- 1990-03-06 JP JP2052700A patent/JPH0674387B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007524747A (en) * | 2004-02-25 | 2007-08-30 | ビーエーエスエフ アクチェンゲゼルシャフト | Method for producing a polymer powder that is well redispersible in water |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03255119A (en) | 1991-11-14 |
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