Патент USA US2115852код для вставки
Patented May 3, 1938 1 ‘2,115,852 UNITED STATES PATENT OFFICE’! AZO DYES Chester w. Hannum and Swanie s. Rossander, ' Wilmington, DeL, assig'nors to E. I. du Pont de Nemours & Company, Wilmington, Del., a. corporation of Delaware - ' _No Drawing. Application July 8, 1937, Serial No. 152,527 . 4 Claims. This invention relates to blue and violet dyes (Cl. 8-5) ‘ with a dyestuil! represented in'the form of- it of the azo class and 'to means of producing and free acid by the formula: , ' applying them. I The prior art discloses blue and violet dyes of a type bearing a super?cial similarity to the dyes of this invention.‘ In German Patent 163,321 (1905), for example, are dyes which have fair utility but are lacking in su?lcient fastness to . - Y Y Y Y (3028): v washing, whereby the utility is greatly diminished. '10 It is an object of this invention to produce new dyes of blue and violet ‘shades which have ex ceptional fastness to washing and which are also in which aryl is one of the group consisting of benzene and alpha-naphthylamine, at least one 10. fast to light, heat, chlorine, and the other in ?uences which a?’ect the permanence of dyes. The objects 01' the invention are attained, generally speaking, by manufacturing and apply ing to the ?ber by development thereon the class group from the class consisting of carboxylic acid I and suli’onic acid, E is one of the group consist of colors represented by the formula: of the said aryls having a water-solubilizing ing of benzene and phenyl pyrazolone, ‘having a free amino group, and Y is at least one of the I ‘ group consisting of hydrogen, alkyl, alkoxy, and halogen, diazotizing and developing with beta naphthol, preferably, or with phenyl-pyrazolone, acetoacet-arylide, and meta-tolylene-diamine, or with a benzene or naphthalene compound capable of coupling. ‘ . ‘ ‘ The following examples illustrate the inven . tion but do not limit it. 25 I Example! - - I ' Five parts of cotton piece goods are dyed in the Y usual‘ manner known to those in the art with four 80 in which aryl is one of the group consisting of ' ' benzene and alpha naphthylamine and in which at least one “aryl" has a water-solubilizing sub stituent, E has a single nucleus from the group consisting . of benzene and phenyl-pyrazolone, 35 Z has a single nucleus from the group consisting of beta-naphtha], phenyl-pyrazolone, meta-' tolylene-diamine, and acetoacet-arylide, and Y is hundredths part of H-acld-mlpha naphthyla mine—>1,6-Cleves acid->cresidine. The dyed fab ric (blue in shade) is rinsed in cold water and put in a casserole with 200 parts of water at 120° G. Add three-tenths part ofsodium nitrite and four tenths part of sulfuric acid. Stir 15 minutes. Rinse with cold water. Dissolve one-tenth part of Z-naphthol in 200 parts ofwater and one 85 twentieth part of caustic soda. Stir the solution - one or more of the group consisting of hydrogen, rapidly while adding the above rinsed piece goods. Stir for 15 minutes. Rinse in cold water and dry. 40 alkyl, alkoxy, halogen, carboxy, and sulfonic acid. The dyeing is a blue shade. The dye is applied to the ?ber by directidyeing formula of the dye on the iiber is:The‘ probable S OrNB . . N= N=N N=1~l OaNa ' . 0 " i ' _ 0mg. ' ' arrests _ Shade Coupling component Diem component ‘ _ on cellu lose -naphthyiamine—>i,6-Olevee acid—-—-) Beta-nsphthoi ................ -- Blue. . Vioiet. Do. ' Biu . Do. 10 Do. Glevu acid-4 - naphthyiamine—>l,6 - Oleves acid-r Do. -naphthyiamine—-)l,6 - Cieves ldd-——) Do. Cloves acid-e Do. - Cleves acid-e Do. v15 Do. Do. Cloves acid->1, G-Cleves 20 1,6 - 25 In the foregoing tablethe arrows mean ‘coupled ' nucleus from the group consisting. of benzene and by the diazo reaction. . 30 ' These colors‘ have excellent shades of blue and violet and outstanding fastness to washing and ‘ outstanding discharge properties. They are also fast to the usual destructive in?uences and ac cordingly are superior colors. , At least one of the center nuclei must contain a water-solubiiizing group, such as suifonic or'car boxylic acid and two such groups are often of assistance. Each of the aryl nuclei may also ' phenyl pyrazolone, Z has a single nucleus from the group consisting of beta-naphthol, l-phenyl- _ 3-_methyl-5-pyrazolone, meta-tolylene diamine, acetoacet-arylide, and Y is one or more of the group consisting of hydrogen, alkyl, alkoxy, halogen, carboxy, and sulfonic acid. 3. The compound representedin the form of a . its free acid by the formula: contain one or more substituents from the group consisting of hydrogen, halogen, alkyl, alkoxy, . carboxy. and sulfonic acid. OH As many apparently widely diiierent embodi ments of. this invention may be made without de parting from the spirit and scope thereof, it is to be understood that we do not limit overselvcs in which aryl is one of the’ group consisting of 45 benzene and alpha'naphthylamine and in which ' to the specific embodiments thereof except as de at least one “aryl” has a water-s'olubilizing sub ?ned in the appended claims. stituent, E has a single nucleus from the group We claim: . 1. The compound represented in the form of consisting. of benzene and phenyl-pyrazolone, Z has a single nucleus from the group consisting of its sodium salt by the formula: 40 I Y . 50 BOaNa 03 55 N: OsNl 8.4%“? 2. The compound'represented in the form of its beta-naphthol, phenyl-pyrazolone, meta-tolyl ene-diamine, and acetoacet-arylide, and Y is one free acid by the formula: (30x3); 2 70 80:3 in which a l is one of a group consisting ‘of * or more of the groupv consisting of hydrogen, benzene and aipha-naphthylamine, E has a single aikyl, alkoxy, halogen, carboxy, and sulfonic acid. 18 2,115,852 4. The process which comprises dyeing cellu lose with a compound representedin the form of itsfree ‘acid by the formula: 5 ' I | on ‘f ‘If N=N--ary1—N=N—aryI-N=N~E — Y (H038); 3 group from the class consisting of carboxylic acid and sulfonic acid, E is one of the group consisting of benzene and phenylpyrazolone, having a free amino group, and Y is at least one of the group _ consisting of hydrogen, alkyl, alkoxy, and halo gen, diazotizing the color on the ?ber, and coupling it to one of a groupof compounds con sisting of 'beta-naphthol, ,1-phenyl-3-methy1-5 pyrazolone, meta-tolylene-diamine and acetoaceté 10 arylide. in which aryl is one of the group consisting of " benzene and alpha-naphthylamine, at‘ least one of the said aryls having a. water-solubilizing | _ ’ - ' 10 _ CHESTER W. HANNUM. SWANIE S. ROSSANDER. '