CN1125240A - 单偶氮型吡啶酮系复合染料 - Google Patents

单偶氮型吡啶酮系复合染料 Download PDF

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CN1125240A
CN1125240A CN 95119354 CN95119354A CN1125240A CN 1125240 A CN1125240 A CN 1125240A CN 95119354 CN95119354 CN 95119354 CN 95119354 A CN95119354 A CN 95119354A CN 1125240 A CN1125240 A CN 1125240A
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dyestuff
dye
disperse
monoazo
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CN1049674C (zh
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高昆玉
李幕洁
周迎娣
马星华
王纯
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Beijing dyestuff factory
CHEMICAL ENGINEERING COLLEGE DALIAN UNIV OF SCIENCE AND ENGINEERING
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Beijing dyestuff factory
CHEMICAL ENGINEERING COLLEGE DALIAN UNIV OF SCIENCE AND ENGINEERING
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
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Abstract

本发明提出下列结构的单偶氮型吡啶酮系复合染料，
式中R1及R2分别为NO2、Cl及COH3，R3为含C1～C4的烷基；由一个或一个以上的上述结构染料，同时添加适量C.I.分散红50(或54或73)或C.I.分散橙25(或30或76)，组成色光接近于C.I.分散黄23的分散染料；可用于普通涤纶纤维、超细纤维的染色，上染率～95％；也可作快速染色用。

Description

单偶氮型吡啶酮系复合染料
本发明提出由一个或一个以上的单偶氮型吡啶酮系复合染料，与适量的C.I.分散红50(或54或73)或C.I.分散橙25(或30或76)复配组成性能接近C.I.分散黄23的染料。偶氮型吡啶酮系染料结构如下：式中R1及R2可分别是H、Cl、NO2及OCH3，R3为含1～4个碳原子的直链烷基。
本发明同时涉及复合染料的制备方法及复配工艺。
据文献记载，由两个在吡啶酮环氮原子上带有不同碳原子个数(如CH3及C2H5)的染料复配使用于染色和印花时，可提高上染率(见Ger.offen4,331,008)。本发明的实验表明，由结构式为I及II的染料分别复配使用时，其性能明显优于单独使用的结果。
复合染料的制备方法可以用两个不同的重氮组分与一种结构的吡啶酮衍生物偶合制得；同样可以用一种重氮组分和两种含不同烷基的吡啶酮衍生物合成得到。此外，还可用单一染料在研磨之前按比例进行复配；或者将单一染料在研磨之后进行湿拼喷干。适量的分散红或分散橙系用后一种方法加入。采用单一染料进行干法混合复配得到的染料，其性能差于前几种方法的结果。
复合染料的复配配方中一般吡啶酮系染料的含量为90～100％、分散红或分散橙的添加量为0～10％。所用的分散剂主要是阴离子型扩散剂，如烷基取代(或未取代)萘磺酸甲醛缩合物、取代或未取代苯酚和甲醛及亚硫酸盐等的缩合物，以及木质素磺酸的碱金属盐等；必要时可添加少量非离于型表面活性剂，如含5～10个乙烯基和C8～C10烷基苯酚的聚合物。扩散剂的磺化度及分子量大小直接影响染料研磨时难易程度及其高温分散稳定性。
染料的研磨可在10～90℃之间进行，以30～60℃最为适宜。染料的颗粒必须研磨到一定的细度，一般在0.2μm～5μm之间，但以～0.3μm较为适宜。
染料在研磨之前要先进行热处理，处理过程可以与研磨结合进行。热处理温度为60～130℃，但以90℃以上较为适宜。热处理介质为水或有机溶剂。在水中添加0.5～3％的扩散剂或非离子型表面活性剂在高温下处理后进行过滤和洗涤。
原染料干品和扩散剂的比例是：染料20～60％、扩散剂40～80％，由于扩散剂的用量不同可制成力份为100份或200份的商品。
本发明提出的复合染料色泽鲜艳，具有优良的染色性能，如匀染性好、提升力好、竭染率高、耐光及耐洗性能好，可用于涤纶、聚酰胺及三醋酸纤维等的染色。除用于常规细度的合成纤维染色之外，在超细纤维上同样可以获得好的效果；上述复合染料还可用于快速染色。
本发明通过以下实例对提出的单偶氮型吡啶酮系复合染料作进一步说明。
实例一：将13.8g对硝基邻甲氧基苯胺及26ml浓盐酸加入到200ml水中，加热到沸腾使之溶解，冷却到0～5℃之后滴加由6.9g亚硝酸钠配成的～30％溶液，并用碘殿粉试纸检查终点。反应结束后，过滤得到澄清溶液，备用。
将1.72g对硝基邻氯苯胺加入到予先由0.7g干燥的亚硝酸钠和15ml浓硫酸制成的亚硝酰硫酸中，在15～20℃进行重氮化。反应结束后用150ml冰水稀释之。
将19.6gN-乙基吡啶酮用300ml水加热溶解，并用氢氧化钠溶液调pH为8～9，待溶液冷却后，于5℃搅拌下将其加入到上述两种重氮盐的混合液中进行偶合4h，过滤，用热水洗涤到滤液呈中性。
将滤并放到1立升水中打浆，加入1g表面活性剂，升温到85～95℃搅拌4～6h，过滤，滤并用热水洗涤数次，干燥。
取上述染料干品25份，扩散剂50份(其中扩散剂NNO及木质素磺酸盐各25份)和水70份水一同进行研磨，然后加入17份C.I.分散红54染料进行喷雾干燥。
取0.25g染料分散在250ml水中，吸取20ml和60ml水混和，用醋酸调染浴pH为5，放入1g涤纶纤维进行染色，于30min内由70℃升温到130℃，保温30min；用残液法测定染料的上染率＞90％。
实例二：将染料I干品(式中R1及R3分别为OCH3及C4H9)2.5g，染料II干品(式中R2及R3分别分Cl及C2H5)7g和C.I.分散橙760.5g，以及扩散剂18g一同进行研磨，干燥后使用。
实例三：将两种不同结构的染料I(式中R1分别为H及OCH3、R3为C3H9)和C.I.分散橙30。先分别加入扩散剂研磨，然后取湿浆复配后干燥使用；三组分的复配比例为75∶20∶5。
实例四：将两种不同结构的染料II(式中R2分别为Cl及OCH3)和C.I.分散红73分别研磨后得到的干品进行复配使用；三组分的比例为42∶50∶8。
下表列有本发明推荐的复配用染料比例，按照上述实例介绍的制备方法可以得到用于染涤纶纤维、性能良好的黄色染料。附表
                          C.I.分散橙    C.I.分散红序号染料    R1   R2   R3                                   重量比
                          25    30    76    50    54    731    I      H          C2H5                                    60
 I     OCH3       C2H5                                    402    I      H          C3H7                                    70
 I     OCH3       C3H7                                    30
                              C.I.分散橙    C.I.分散红序号  染料    R1   R2   R3                                       重量比
                             25    30    76    50    54    73
  I       H          C4H9                                      803    I       OCH3      C4H9                                      20
  I       H          C2H5                                      854    I       OCH3      C2H5                                      10
                             O                                    5
  I       H          C3H7                                      855    I       OCH3      C3H7                                      15
                                         O                        5
  I       H          C4H9                                      756    I       OCH3      C4H9                                       20
                                   O                              5
  I       H          C2H5                                      707    I       OCH3      C2H5                                      20
                                                      O          10
  I       H          C3H7                                      758    I       OCH3      C3H7                                      20
                                               O                  5
  I       H          C4H9                                      809    I       OCH3      C4H9                                      15
                                                           O      5
  I       Cl         C2H5                                      6010   I       OCH3      C2H5                                      40
  I       Cl         C3H7                                      7011   I       OCH3      C3H7                                      30
  I       Cl         C4H9                                      8012   I       OCH3      C4H9                                      20
  I       Cl         C2H5                                      8513   I       OCH3      C2H5                                      10
                            O                                     5
                                C.I.分散橙    C.I.分散红序号  染料    R1   R2   R3                                          重量比
                               25    30    76    50    54    73
  I       Cl          C3H7                                        8514   I       OCH3       C3H7                                        15
                                            O                        5
  I       Cl          C4H9                                        7515   I       OCH3       C4H9                                        20
                                     O                               5
  I       Cl          C2H5                                        7016   I       OCH3       C2H5                                        20
                                                        O            10
  I       Cl          C3H7                                        7517   I       OCH3       C3H7                                        20
                                                  O                  5
  I       Cl          C4H9                                        8018   I       OCH3       C4H9                                        15
                                                              O      5
  II      OCH3       C2H5                                        90
  II                          O                                      10
  II      OCH3       C3H7                                        80
                              O                                      2021   II      OCH3       C4H9                                        70
                              O                                      30
  II      OCH3       C2H5                                        90
                                          O                          1023   II      OCH3       C3H7                                        80
                                          O                          2024   II      OCH3       C4H9                                        70
                                          O                          30
                                       C.I.分散橙    C.I.分散红序号 染料    R1   R2         R3                                         重量比
                                   25    30    76    50    54    73
 II            Cl         C2H5                                         5025                OCH3      C2H5                                         40
                                                            O            10
 II            Cl         C3H7                                         6026  II            OCH3      C3H7                                         30
                                                      O                  10
 II            Cl         C4H9                                         7027  II            OCH3       C4H9                                        20
                                                                 O       5
 I       H                C2H5                                         5028  II            OCH3      C4H9                                         40
                                  O                                      10
 I       H                C4H9                                         4029  II            OCH3      C2H5                                         40
                                        O                                20
 I       H                C4H9                                         6030  II            OCH3      C4H9                                         30
                                               O                         10
 I       Cl               C4H9                                         5031  II            OCH3      C2H5                                         40
                                 O                                       10
 I       Cl               C3H7                                         4032  II            OCH3      C3H7                                         40
                                      O                                  20
 I       Cl               C2H5                                         6033  II            OCH3      C4H9                                         30
                                             O                           10
 I       OCH3            C4H9                                        2034  II            Cl         C2H5                                         70
                                                     O                   10
                           C.I.分散橙    C.I.分散红序号 染料    R1   R2   R3                                   重量比
                            25   30   76   50   54   73
 I      OCH3       C2H5                                  2035  II     Cl          C4H9                                  75
                                           O                 5
 I      OCH3       C3H7                                  1536  II     Cl          C3H7                                  80
                                                      O      5

Claims (6)

1.一种单偶氮染料混合物，其特征是有一个或一个以上下列结构的染料：
Figure A9511935400021
式中R1及R2可分别是H、Cl、NO2及OCH3，R3为含1-4个碳原子的直链烷基；同时添加一种分散红或分散橙染料，如C.I分散红50、54、70或C.I分散橙25、30、76。
2.根据权利要求1所述的单偶氮染料混合物，其特征在于复合染料中含有权利要求1中列出的一个或两个结构式I或结构式II的染料，染料的含量为10-90％。
3.根据权利要求1所述的单偶氮染料混合物，其特征在于复合染料中含有添加的分散红或分散橙色染料含量为0-10％
4.根据权制要求1所述的单偶氮染料混合物，其特征在于复合染料可由权利要求1中列出的结构式I染料(R1为OCH3及Cl、R3为C2H5及C4H9)和C.I分散红54或C.I分散橙30组成。
5.根据权利要求1所述的单偶氮染料混合物，其特征在于复合染料可由权利要求1中列出的结构式II染料(R2为OCH3及Cl、R3为C2H5及C4H9)和C.I分散红73或50组成。
6.根据权利要求1所述的单偶氮染料混合物，其特征在于复合染料可由权利要求1中列出的结构式I染料(R1为OCH3、R3为C4H9)、结构式II染料(R2为Cl、R3为C4H9)及C.I分散橙25组成。
CN95119354A 1995-12-20 1995-12-20 单偶氮型吡啶酮系复合染料 Expired - Fee Related CN1049674C (zh)

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CN101654566A (zh) * 2009-09-10 2010-02-24 董源 单偶氮型组合物染料
CN102093756A (zh) * 2011-01-12 2011-06-15 浙江山峪染料化工有限公司 一种节能型偶氮类分散染料的制备方法
CN103044968A (zh) * 2013-01-11 2013-04-17 浙江山峪染料化工有限公司 一种分散黄染料配方
CN103087543A (zh) * 2012-12-19 2013-05-08 南京大学 苯并异噻唑偶氮吡啶酮类分散染料及其制法和用作为纤维识别试剂
CN103232729A (zh) * 2013-01-10 2013-08-07 浙江山峪染料化工有限公司 多组份拼混型分散黄染料配方
CN103232727A (zh) * 2013-01-10 2013-08-07 浙江山峪染料化工有限公司 一种多组份拼混型分散黄染料配方
CN103232730A (zh) * 2013-01-10 2013-08-07 浙江山峪染料化工有限公司 一种混拼型分散黄染料
CN103232728A (zh) * 2013-01-10 2013-08-07 浙江山峪染料化工有限公司 混拼型分散黄染料
CN103694733A (zh) * 2011-12-20 2014-04-02 上海安诺其纺织化工股份有限公司 染料组合物、染料、其制备方法及该染料的原料组合物
CN103709790A (zh) * 2011-12-20 2014-04-09 上海安诺其纺织化工股份有限公司 染料组合物、染料、其制备方法及该染料的原料组合物
CN108047752A (zh) * 2017-12-29 2018-05-18 东营安诺其纺织材料有限公司 一种分散黄的生产工艺

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CN101654566A (zh) * 2009-09-10 2010-02-24 董源 单偶氮型组合物染料
CN102093756A (zh) * 2011-01-12 2011-06-15 浙江山峪染料化工有限公司 一种节能型偶氮类分散染料的制备方法
CN103694733A (zh) * 2011-12-20 2014-04-02 上海安诺其纺织化工股份有限公司 染料组合物、染料、其制备方法及该染料的原料组合物
CN103709790A (zh) * 2011-12-20 2014-04-09 上海安诺其纺织化工股份有限公司 染料组合物、染料、其制备方法及该染料的原料组合物
CN103087543B (zh) * 2012-12-19 2014-10-01 南京大学 苯并异噻唑偶氮吡啶酮类分散染料及其制法和用作为纤维识别试剂
CN103087543A (zh) * 2012-12-19 2013-05-08 南京大学 苯并异噻唑偶氮吡啶酮类分散染料及其制法和用作为纤维识别试剂
CN103232727A (zh) * 2013-01-10 2013-08-07 浙江山峪染料化工有限公司 一种多组份拼混型分散黄染料配方
CN103232730A (zh) * 2013-01-10 2013-08-07 浙江山峪染料化工有限公司 一种混拼型分散黄染料
CN103232728A (zh) * 2013-01-10 2013-08-07 浙江山峪染料化工有限公司 混拼型分散黄染料
CN103232729A (zh) * 2013-01-10 2013-08-07 浙江山峪染料化工有限公司 多组份拼混型分散黄染料配方
CN103232728B (zh) * 2013-01-10 2014-08-20 浙江山峪染料化工有限公司 混拼型分散黄染料
CN103232727B (zh) * 2013-01-10 2014-09-03 浙江山峪染料化工有限公司 一种多组份拼混型分散黄染料
CN103232730B (zh) * 2013-01-10 2015-01-14 浙江山峪染料化工有限公司 一种混拼型分散黄染料
CN103044968A (zh) * 2013-01-11 2013-04-17 浙江山峪染料化工有限公司 一种分散黄染料配方
CN103044968B (zh) * 2013-01-11 2014-10-22 浙江山峪染料化工有限公司 一种分散黄染料
CN108047752A (zh) * 2017-12-29 2018-05-18 东营安诺其纺织材料有限公司 一种分散黄的生产工艺

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