• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:

    公开号:SU735173A3
    申请号:SU782628098
    申请日:1978-06-23
    公开日:1980-05-15
    发明作者:Линхард Пауль；Игбал Абул；Петер Хайнц
    申请人:Циба-Гейги Аг (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to the field of dyeing and finishing production, in particular to the method of dyeing linear polyamide. The known method of dyeing a linear polyamide by introducing a mass of the salt of the chromium complex -1: 2 monoazo dyes of the general formula x :: -carb: xy or sulfo; , t - 1-3; x hydrogen, alkyl, alkoxy on or alkylsulfonyl per group with 1-6 carbon atoms, alkoxy group with 2-5 atoms. carbon and group R - hydrogen, alkyl with 1-6 carbon atoms, oxyalkl with 2-6 carbon atoms genus, alkoxyalkyl with 3-6 a volumes of carbon or phenyl unsubstituted or substituted by halogen, alkyl with 1-4 carbon atoms; hydrogen, alkyl with 1-6 carbon atoms or oxyalkyl with 2-6 carbon atoms; hydrogen, halogen or alkyl with 1-6 carbon atoms in an amount of 3% by weight of polyamide 1. However, in the process of dyeing it is polydestructed. The purpose of the invention is the elimination of polyamide dyeing. This goal is achieved due to the fact that in a known method, in each salt of the chromium complex 1; 2 color dyes they use a compounding formula. T tH N4.Vi () C), j (... Xf
    carboxy or sulfode X group; . .
    In mono-, di- and triamine with 1-18 carbon atoms; 1-3; -in, t
    t-1 p g
    t t
    XT I x, hydrogen, alkyl, alkoxy. , Nal or alkylsulfonyl group with 1-6 carbon atoms, alkoxy group with 2-5 carbon atoms and group
    de R is hydrogen, alkyl with 1-6 carbon atoms, hydroxyalkyl with 2-6 carbon atoms, y7 alkrxyalkyl with 3-8 carbon atoms or phenyl, unsubstituted or substituted with halogen, alkyl with 1-4 carbon atoms,
    - hydrogen, alkyl with 1-6 at.
    R
    carbon atoms or oxyalkyls with 2-6 carbon atoms; . -
    - hydrogen, halogen or alkyl with 1-6 carbon atoms X and Yj or Xd and UZ vieste form: fused benzene ring; / Z - oxygen or carboxyl group. Or residues

    V -0
    mean group
    f .. - | gt
    -year
    Example 1. To a well-stirred suspension of 84.38 g (0.1 mol) of 1: 2-chromium sodium salt of 2-amino-5-ethylsulfonylphenol-1-phenyl-3-methyl-5-pyrazolone azo dye in 1300 ml water at 90950 ° C for 15 minutes, a drop of a solution of 5.8 g (0.05 mol) of hexamethylenediamine in 100 ml species and 5.5 g of formic acid (0.12 mol) was added dropwise. The mixture is allowed to react with stirring for 1 hour at 90-95 ° C and then filtered under low vacuum. The filter cake was sequentially washed with 600 ml of a 1% solution of formic acid and 600 ml of water. The product, dried in vacuum (IO-115-C), weighs 87.8 g. It contains 97.1% of a colored salt and only 0.25 % NaCI and 1% water.
    By spinning polycaprolactam, a red colored fibrous material is obtained which has very good light resistance, resistance to wet treatments, resistance to abrasion and heat-setting.
    Example 2. To a solution heated to a solution of 16.87 g (0.02 mol) of the 1: 2-chromium sodium salt from the azo dye of 2-amino-5-ethylsulfonylphenol-1-phenyl-3-methyl-5-pyrazolone in 250 ml of ethanol for A solution of 1.16 (0.01 mol) of hexamethylenediamine in 50 ml of ethanol and 1.1 g (0.024 mol) of formic acid is added dropwise for 30 minutes. The reaction mixture was allowed to cool to room temperature. The mixture is stirred for the next 3 hours and you, a falling crystalline precipitate are filtered off, washed with 50 ml of ethanol and then dried in a vacuum oven at 110-115 ° C. 16.7 g of dye salt are obtained.
    Example 3. 16.87 g (O-, 02 mol of the sodium salt of 1: 2-hr6mogr of the 2-amino-5-ethylsulfonylphenol-1-phenyl-3-methyl-5-. Pyrazolar 3 complex is suspended in 250 ml, n -butanol and heated until the dye partially dissolves. Then a solution of 1.16 g (0.01 mol) of hexamistilide diamine in 50 ml of water and 1.1 g (.0.0.24 mol) of formic acid is added dropwise over 30 minutes.
    The reaction mixture is allowed to cool to room temperature and is stirred for another 3 hours at this temperature, and the dye salt precipitates as α-crystals. After filtration, washing the filter cake with noMOtttbio with 50 ml of n-butanol and drying in a vacuum oven at 110IIS C, 14.4 g of the dye salt are obtained.
    Example 4. A suspension of 13.13 g (0.02 mol) of sodium salt
    1s2-xpOMOBoro complex of azokra-. 2-aminophenol-1-phenyl-Zmethyl-5-pyrazolone knockers in 250 ml of water are heated to 90-95 ° C and stirred well at this temperature for 1 hour. Then a solution of 1.16 g (0.01 mol) of hexamethylenediamine in 50 ml of water and 0.9 ml (0.024 mol) of formic acid is added dropwise within 15 minutes and the reaction mixture is left to react for 1 hour with stirring at 90- 95s Then it is filtered and the filter cake is washed successively with 25 ml of 1% formic acid solution and 125 ml of water. After drying in a vacuum oven at 110-115 0, 12.9 g of the dye salt are obtained. It contains 0.039% NaCl and 4.3% NaO;
    By spinning polycaprolactam, fibrous material colored in a bright red color is obtained, which has very good light resistance, resistance to wet treatments, resistance to abrasion and heat-setting.
    Example 5. Heated to 90-95-C with a solution of 1.16 g (0.01 mol) of hexamethylenediamine in 300 ml of water and 1.10 g (0.024 mol) of formic acid. 16.87 g (0 , 02 mol) of powdered sodium salt of 1: 2-chromium complex from azo dye 2-amino5-ethylsulfonylphen-I-phenyl-Zmethyl-5-pyrazolone. The resulting suspension is stirred for another 1 hour at 90-95 s. It is then filtered under a weak vacuum / the filter cake is washed with 150 ml of 1% formic acid solution and 150 ml of water and dried under a vacuum at 110115-C. The dye salt yield is 17.2 g. It contains 0.071% NaCl and 1.85% water.
    Example 6. A solution of 1.16 g (6.01 mol) of hexamethylenediamine in 50 ml and J. heated to 90-95 ° C is added. 1 g (0.024 mol) of formic acid is added dropwise to a suspension heated to 9 ° C for 30 minutes 16.87 g (0.02 mol) of 1: 2-xr sodium salt (the serpentine complex of the azo dye. 2-amino-5-ethylsulfonyl-phenol-1-phenyl-3-methyl-5-pyrazolone in 200 ml of water. Rinse the dropping funnel with about 20 ml of water and the reaction mixture is left to react with stirring for 1 h at 90–9., the dye precipitated is filtered off, and washed successively with 150 ml of a 1% solution of the ant a different acid and 150 ml of water and finally dried at 110-115 ° C. 17.2 g of the dye salt are obtained, it contains only 0.057 NaCl and 1.4%.
    Example 7. To a heated to 90-95 ° C solution of 18.39 g (0.02 mol) of sodium salt of 1: 2-chromium complex of azo dye. 3-hydroxy-4-aminonaphthalenesulfonic-1-phenyl-3-methyl-5-pyrazolone in 250 ml of n-buta-nola is added dropwise over 40 minutes
    a solution of 3.48 g (0.03 mol) of hexamethylenediamine in 200 ml of water and 3.3 g (0.072 mol) of formic acid. The reaction mixture is cooled to room temperature, with the majority of the colored salt precipitating as
    crystals. The separated product is filtered off, washed with 300 ml of water and dried in a vacuum oven at 110115 ° C. The butanol filtrate is then doubled. The shakes are shaken with water in portions of 100 ml each time, and then completely evaporated in a rotating flask. Thus, an additional small amount of product is obtained, which is also dried in vacuum at 110-115-s. The total yield of CO71I dye is 20.9 g. It contains less than 0.1% sodium chloride. By spraying polycaprolactam, one obtains:. red with bluish cast fibrous material that has a very
    good light resistance, resistance to wet processing, heat-setting and abrasion.
    Example. 18.14 g (0.02 mol) sodium salt of a 1: 2 mixed chromium complex from azo dyes 2-aminophenol-4-sulfomethylamide-1-phenyl-3-methyl-5-pyrazolone and 2-amino-4-methylaminosulfonylphenol-1 -acetamido-7-naphthol is suspended in
    250 ml of water and stirred for 60 minutes at 90-95 ° C, the dye being completely dissolved. A solution of 1.16 g (0.01 mol) of hexamethylenediamine in 50 ml of water and 1.1 g (0.024
    mole) formic acid ja: leave the reaction mixture to react at. stirring for 1 h at 9095 ° C. The precipitated crystalline salt of the dye is filtered off under weak vacuum, washed successively with 125 ml of 1% formic acid solution and 125 ml of water, and then dried in vacuum at 110-115 s. Get 12.9 g of dye salt with
    the NaCI content is 0.039% and the water content is 4.3%.
    By spinning polycaprolactus, a brown colored fibrous material has
    very good light fastness, resistance to wet curing, heat-setting and abrasion.
    Example 9. K, heated to 90-95 C solution of 14.56 g (0.02 mol) of 1: 2-chromium sodium salt complex of azo dye 2-amino4-chlorophenol - M-phenyl-3-methyl-5-pyr a solution of 3.62 g (0.02 mol) of dicyclohexylamine in 50 ml of Ugfl — 5 ml of ethanol are rolled in for 250 min of n-butanol in 250 ml of n-butanol;
    , l g (0.024 mol) of formic acid. The reaction mixture is cooled to room temperature, and a small amount of an:: salt: precipitates out as small crystals. After filtering and washing the precipitate on the filter with a small amount of solvent, the butanol solution is shaken three times with water in portions of 100 ml each time, and then completely evaporated in a rotating flask. The residue, as well as the above filter residue, is dried in a vacuum oven at IIO-IIS C. A total of 17.3 g of the dye salt is obtained with an NaCI O content of 1% and water of 1-2.3%. .,. By polycaprolactus spinning, a red fibrous material is obtained, which has very good light resistance, resistance to wet treatments, heat-setting and abrasion.
    Example 10. To a solution heated to 90-950C, 16.87 g (0.02 mol) of the 1: 2-chromium sodium salt of the 2-amino5-ethylsulfonylphenyl-71-phenyl-3-methyl-5-pyrazolone azo dye, 500 ml n -butanol for a period of 20 minutes, a mixture of 2.0 g (0.01 mol) of 1,12-diaminedecane in 100 ml of water and 1.1 g (0.024 mol) of formic acid is added dropwise. Leave the reaction mixture to react for 1 hour at 90-95 ° C and then cooled to room temperature. The organic phase is separated, extracted three times with water, taking 126 ml each time, and finally completely evaporated in a rotating flask (the bath temperature is maximum). The residue is vacuum dried at 110115 ° C and weighs 10.7 g and contains 0.044% NaCI and 0.69%.
    Example 11. 2g of the dye salt and g of acetone prepared according to Example 4 are mixed with 98 g of polyhexamethylene adipamide in the form of a crumb until a uniform coating of the red salt of the dye is formed on the surface of the crumb Crumb is dried and then melted and spun in a conventional apparatus And moreover, they receive bright-red threads, which have superior resistance to water, abrasion, and shimmering and light.
    Examples 12-91. The indicated column of Tables 1-6 of the number of moles of a 1: 2 chromium complex individual or mixed sodium salt is brought into contact with the said UI column of the tables given by the number of moles of amine described in rimers 1-10. Get valuable pigments of high purity. By powdering polyamide (PA 6) and spinning dyes, fibers are obtained, the colors of which are indicated in column IV of the tables.
    Example 92. 99 g of polyamide from. -caprolactam (polyamide-6) in the form of crumbs is paned dry with the help of 1 g of the colored salt prepared according to example 1. Breaded crumbs are spun in an extruder at 290--295 ° C. Thus, the resulting yarns have a uniform red color with high light resistance and resistance to wet treatment and heat-setting.
    Example 93. 60 g of the dye obtained in Example 1 and 60 g of magnesium behenate are treated in a mixer for 1/4 h at 120-130 ° C. After the homogeneous mixture is obtained, the cooled fragile product is milled. A dye preparation containing 50% of the dye salt is obtained.
    If they follow the procedure described above, however, instead of 60 g of magnesium behenate, 60 g of magnesium stearate is used, then a valuable dye is also obtained.
    EXAMPLE 94. 98 g of polyamide from B.-caprolactam (polyamide-6) in the form of crumbs are paned dry with the help of 2 g of the dye preparation prepared according to example 83. Breaded crumbs are spun in an extruder at 290295 ° C. Thus, the obtained thread has uniform red staining with high light resistance, resistance to wet treatment and to heat-setting.
    The use of a dye of the general formula D in this method eliminates the destruction of the polyamide in the process.
    , 2-Amino-5-ethylsulfonylphenol-1-phenyl-3-methyl-5-pyrazoline 1/2
    Propylene diamine Benzylamine Aniline
    i A luT- f.Jl, ytlDt
    Chamid - 1-phenyl-3-methyl-5-pyrazolone
    2-amino-4-chlorophenol-5-sulfamide - 1-phenyl-3-methyl-5-pyraeolone
    2-Aminophenol-4-sul last 1- (3-chlorophenyl) -3-methyl-5-pyrazolone
     I I
    2-Aminophenol-4-sulfon-N, Ethylethylamide - 1-phenyl-3-methyl-5-pyrazolone
    2-aminophenol-4-sulf-S, N-. . -bis (2-hydroxyethyl) -amid1-phenyl-3-methyl-5-pyrazolone
    2-Amino-4-methylsulfonyl-phenol (3-chlorophenyl) -3-methyl-5-pyrazolone
    2-Aminophenol-4-sulf- (2-methoxyethyl) -amide - 1-phenyl-3-methyl-5-pyrazolone
    2-Amino-5-ethylsulfonyl-phenol 1-phenyl-3-methyl-5-pyrazolone
    I Continued table. one
    Hexamethylenediamine Red
    2-Methoxyethylamine Red
    Hexamethylenediamine Orange
    Stearylamine Orange
    Hexamethylenediamine Orange
    Hexamethylenediamine Orange
    Diethylenetriamine Orange
    Hexamethylenediamine Orange
    Triethylamine Orange
    Hexamethylenediamine Orange
    P-Phenylenediamine Red
    1.12-Diaminododecane Red
    35 12-Aminophenol-4-sulf-y- {2-carboxyphenyl) -amide 1-phenyl-3-methyl-5-pyrazonone
    2-amino-4-chlorphenol
    1-Fennl-3-methyl5-piraeolone
    table 2
    1 1/2 Hexamethylenediamine Orange
    1/2 Gekametilen Red diamine
    Continued table. 3
    15
    735173 2-Aminophenol-42-Aminophenol-4-sul last-2-on -sulfoamide-1- (3-chlorophenyl) 3-Methyl-5-pyrazolone 2-Aminophenol-42-Aminophenol-4sulphisopropyl-sulfisopropyl amide-naphthol with phenyl-3-methyl-5-pyrazolone
    72
    2-amino-phenol-42-amino-phenol-4 sulfamide sulfamide 1- (carbomethoxy1- (3-chlorophenyl) -3-methyl-5-pyr-amino) -7-naphthol
    azolone
    73
    2-Aminophenol-44
    2-Aminophenol-4-sulfmethylamide-sulphide-methylmethamide-1- (4-chlorophenyl-yl) 1-acet-Amido-7-3-methyl-5-pyr-naphthol1 azolone
    75
    2-Aminophenol-4-sulfopenol612-: Amino-4 methyl acid- 1-phenyl-3-phenol-1-phenyl-3-methyl-5-pyr-methyl-5-p Irazolone
    azoLon
    2-Amnno 4-methyl 712-AMINO-4-chlorophenol-1-4-sulfrphenol -1-phenyl) phenyl-3-methyl-5-3-methyl-5-pyr-pyrazolone azolone
    2-amino-4-chlorophenol-1
    81 2-Dmino-4,6-di1- (4-sulfophenyl) -3 chlorophenol - 1-fa-methi.n-pyrazolone 1
    nyl-3-methyl-5-pyrazolone
    Table 5
    M-Chloraniline Brown
    Mesitylamine Brown
    0-Anisidine Di- (2-ethylhexyl), -amy.
    Table
    reKcaMeTHJjBH diamine Red
    1 I. Hexamethylenediamine Cyclohexylamine -Ethylaniline Bordeaux Hexamethylenediamine Bordeaux
    2-Amino-4-methylphenol-1-phenyl-3-methyl-5-pyrazolone.
    2-amino-4-chlorophenol-phenyl-3-methyl-5-pyr. Azolone
    2-AMINO-4, b-di81 chloro-phenol
    2-naphthol
    1 2-Amino-4-phenylsulfonyl-phenol-1-phenyl-3-methyl-5-pyrazolone.
    1 2-AMINO-4- (4-chlorophenylsulfonyl) -phenol - 1-phenyl-3-metvd1-5-pyrazolone
    1 2-DIMO-4- {4-methylphenylsulfonyl) -phenol-1-phenyl-3-methyl-B-pyrazole;
    1 2-Ami o-4-chlorophenol-2-naph5OL
    1 2-Amino-4-chloro4) enol 2-naphthol
    1 2-Amino-4-chlorophenol-2-naphthol
    1 2-aminophenol-4-sulfamide-
    1- (3-aminosulfophenyl) -3methyl-5-pyrazolone
    1 2-Aminophenol-4-sulfamide -V
    1- (3-chlorophenyl) -3-methyl-5pyrazolone
    1 2-aminophenol-4-sulfamide-h
    1- (3-chlorophenyl) -3-methyl-5-pyrazolone
    91 1 2-Aminophenol-4-sulfamide-V 1- (3-chlorophenyl) -3-methyl-5-pyrazolone.
    Continued table. 6
    ..y
    2-amino-4-methylphenol1- (4-sulfophenyl) -3-methyl-5-pyrazolone
    Ethylenediamine Red
    2/3 Diethylene Red triamine
    one ,
    Hexamethylo-Violetodiamini 1
    ; T a b l and c a 7
    1/2 Hexamethylenediamine Orange
    1/2 Hex1 methylenediamine Orange
    1/2 Hexamethylenediamine Orange
    1 / 21,12-Diaminododecane Violet
    . Stearylamine
    Violet
    4,13-Diamine 6-2, 1-5-dimethyl
    Purple Hexadecane
    1/2 Hexamethylenediamine Orange
    1/2 1.12-Diaminodecane Orange
    1/2 4, GZ-Diamino-2.15
    Dimethylhexadecane Orange
    Orange
    权利要求:
    Claims (1)
    [1]
    Stearylamine Formula of the Invention The method of linear polyamide dyeing by introducing monoazoxy chromic complex 1: 2 into the salt mass, which is different from the compound of general formula 1 tN -) g (B4, i t carboxy or sulfo group; - MONO-, di- or triamine with 1-18 carbon atoms) - 1-3; - gp-1; n X is hydrogen, alkyl, and 1c6xybna or alkylsulfonyl per group with 1-6 carbon atoms. . genus, alkoxy group with 2-5 carbon atoms and SOjNRR group hydrogen, alkyl with 1-6 carbon atoms, oxyalkyl with 2-6 carbon atoms, alkoxyalkyl with 3-8 carbon atoms or phenyl, unsubstituted or substituted halo gene, alkyl with 1 -4 carbon atoms, hydrogen, alkyl with 1-6 carbon atoms or oxyalkyl with. 2-6 carbon atoms; hydrogen, halogen or alkyl with 1-6 carbon atoms, or X, and YI or Xg together 20 form a fused benzene ring, oxygen or a carboxyl group or methyl residues, a carbomayl group or an alkoxycarbonyl group with 2-6 carbon atoms; hydrogen, halogen, methyl, sulfoyl group; hydrogen halogen; hydrogen, alkanoylamino group of carbon atoms, and, if., Y, Yj and, then the residues. ruppu l; -o N have the above amount of 0.1-10% of Veda data points, attention during examination: nt UK No. 1021737 published 15.01.67 (proto
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2814614A|1953-04-02|1957-11-26|Ciba Ltd|New conversion products of azo dyestuffs containing metal compounds in complex union|
    DE1110786B|1958-06-12|1961-07-13|Geigy Ag J R|Process for the preparation of acetone-soluble conversion products of metallized azo dyes|
    DE1260652B|1960-08-09|1968-02-08|Basf Ag|Process for the preparation of ammonium salts of metal complex dyes|
    GB1021737A|1963-05-08|1966-03-09|Ici Ltd|Process for the coloration of polyamides|
    NL129233C|1965-01-15|
    DE1619357C3|1966-12-29|1974-08-08|Basf Ag, 6700 Ludwigshafen|Use of highly concentrated, stable, water-miscible, sulfonic acid group-free 1: 2 chromium or cobalt complexes of azo dyes containing stock solutions for the preparation of dye baths or printing pastes|
    RO53376A|1968-02-02|1973-03-15|
    DE1814321B2|1968-12-12|1971-04-29|DEVICE FOR COMPENSATION OF A DEPENDENT ANGLE OF DEPENDENT AMPLITUDE CHANGES FROM VOLTAGE PULSES GENERATED IN A DETECTOR FOR ROENTGEN QUANTUMENTS|
    CH524012A|1969-02-25|1972-01-31|Ciba Geigy Ag|Process for the continuous dyeing or printing of textile material made of synthetic polyamide|
    FR2212398B1|1972-12-28|1976-06-04|Ugine Kuhlmann|
    FR2219964B1|1973-03-02|1978-03-03|Ugine Kuhlmann|
    CH616953A5|1975-08-27|1980-04-30|Sandoz Ag|
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    DE3920029C2|1988-06-30|1999-05-20|Clariant Finance Bvi Ltd|Dyes for coloring plastics|
    US5510467A|1989-01-03|1996-04-23|Sandoz Ltd.|Salts of metal-free anionic phenylazopyrazolone dyes having cations containing sterically hindered amine groups|
    US5942438A|1997-11-07|1999-08-24|Johnson & Johnson Medical, Inc.|Chemical indicator for oxidation-type sterilization processes using bleachable dyes|
    US20020156161A1|2000-02-11|2002-10-24|Reiko Koshida|Thermoplastic resin compositions for laser welding and articles formed therefrom|
    EP1606438A2|2003-03-18|2005-12-21|Ciba SC Holding AG|Colored polymeric articles having high melt temperatures|
    US7294730B2|2005-11-30|2007-11-13|Xerox Corporation|Colorant compounds|
    JP2015063631A|2013-09-26|2015-04-09|日本化薬株式会社|Azo compound|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    CH772277|1977-06-23|
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