US1873278A - Dyeing of regenerated cellulose materials - Google Patents

Dyeing of regenerated cellulose materials Download PDF

Info

Publication number
US1873278A
US1873278A US445227A US44522730A US1873278A US 1873278 A US1873278 A US 1873278A US 445227 A US445227 A US 445227A US 44522730 A US44522730 A US 44522730A US 1873278 A US1873278 A US 1873278A
Authority
US
United States
Prior art keywords
regenerated cellulose
dyed
acid
naphthol
amino
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 - Lifetime
Application number
US445227A
Inventor
Brightman Rainald
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Application granted granted Critical
Publication of US1873278A publication Critical patent/US1873278A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/025—Disazo dyes containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • the secondary disazo dyestuffs obtained by coupling a diazotized amine f the benzene series with an amino-naphtholsulphonic acid in alkaline solution, diazotizing the aminoazo dyestuii obtained and coupling with a suitable coupling com onent are used for the production of even yeings on re enerated cellulose rayon.
  • the dyestufl's so 0%)tained give shades varying from orange and red to bluish violet or blue and are characterized by the valuable property of dyeing viscose ra on in even shades.
  • R represents a coupled residue of a diazotized amine of the class consisting of chlor-aniline, amino-benzoic acid and anisidine
  • R represents a naphthalene residue
  • R represents a coupled residue of an azo dye coupling component of the class consisting of beta-naphthol, nitro-m-phenylene diamlne, salicylic acid and amino-naphthol sulphonic acids
  • m is 1 or 2.
  • this generic class of dyes there are several subgeneric classes which are especially advantageous for dyeing regenerated cellulose materials in even level shades. The following structural formula indicate certain of these subgeneric classes which are typical. In the following formulae R R R and m have the same significance as above.
  • the rayon may be entered into the bath nearly at the boil and allowed to cool gradually during the dyeing.
  • b th f ll i tr tu l f be also used in the dyebath, other salts or dye- It; following generic formulae, X ing assistants, as borax.
  • the invention 18 further and the other symbols have the examples in the following the subgeneric classes given generic classes which may be illustrated by the table:
  • R represents the coupled residue of a diazotized amine of the class consisting of chloraniline, amino-benzoic acid and anisidine, R represents a naphthalene residue, and a; is 1 or 2, thereby dyeing said "regenerated NH: ::N
  • N N- III H OaS x cellulose materials in even level shades.
  • l dyebath is made up from 3000 parts of x 20 parts of Glaubers salt, 3 parts of wherein R represents a coupled residue of and 2 parts of the dyestufi' obtained an azo dye coupling component of the class' a hydrogen or a sulphonic group,
  • R represents a Cl, an OCH or a COOH group and w is 1 or 2, thereby dyeing said regenerated cellulose materials in even level shades.
  • R represents a Cl, an OCH or a COOH oup
  • R represents a naphthalene residue
  • R represents a coupled residue of an azo dye coupllng component of the class consisting of beta-naphthol, nitro-m-phenylene diamine, salicylic acid and amino-naphthol sulphonic acids
  • m is 1 or 2
  • R represents a coupled residue of a diazotized amine of the class consisting of chlor-aniline amlno-benzoic acid and anisidine, R and ill, represent a naphthalene residue, and w is 1 or 2, the said dyed regenerated cellulose having even level shades.
  • R represents a coupled residue of an azo dye coupling component of the class consisting of 2-amino-8-naphthol6-sulphonic acid, nitro-phenylene-meta-diamine, betanaphthol, and salicylic acid
  • X represents hydrogen or a SO H group
  • R represents a naphthalene residue
  • R represents a coupled residue of an azo dye coupling component of the class consisting of beta-naphthol, nitro-in-phenylene diamine, salicylic acid and ainino-naphthol sulphonic acids and m is 1 or 2, the said dyed regenerated cellulose materials having even level shades.
  • R represents a coupled residue of an azo dye coupling component of the class consisting of beta-naphthol, nitro-m-phenylene diamine, salicylic acid and amino-naphthol sulphonic acids and w is 1 or 2, the said dyedregenerated cellulose having even level shades.
  • R represents a naphthalene residue
  • w is 1 or 2
  • the said dyed regenerated cellulose having even level shades.
  • N N x no: II
  • R represents a. naphthalene residue
  • R represents chlorine or an alkoxy group
  • a: is 1 or 2, the said dyed regenerated cellulose having even level shades.
  • R represents a coupled residue of an azo dye couplmg com onent of the class consisting of beta-napht ol, nitro-m-phen lene diamine, salicylic acid and amino-nap ithol sulphonic acids
  • R represents chlorine, a carbox lie or alkoxy group
  • X represents H or 0 H group, the said dyed regenerated cellulose having even level shades.
  • R represents chlorine, or a COOH or OCH group
  • R represents the coupled residue of an azo dye coupling component of the class consisting of beta-naphthol, nitro-phenylene-meta-diamine, salicylic acid, 2-amino-8-naphthol-6-sulphonic acid and 1 8 amino-naphthol-4-sulphonic acid, the said dyed regenerated cellulose having even level shades.

Description

Patented .Aug. 23, 1932 BAINALD BRIGHTMAN, OF BLACKLEY, MANCHESTER, ENGLAND, ASSIGNOR TO I]!- PEBIAL CHEMICAL INDUSTRIES LIMIT ED, OF LONDON, ENGLAND DYEING OF BEGENERATED CELLULOSE MATERIALS No Drawing. Application filed April 17, 1930, Serial No. 445,227, and in Great Britai According to. this invention the secondary disazo dyestuffs obtained by coupling a diazotized amine f the benzene series with an amino-naphtholsulphonic acid in alkaline solution, diazotizing the aminoazo dyestuii obtained and coupling with a suitable coupling com onent, are used for the production of even yeings on re enerated cellulose rayon. The dyestufl's so 0%)tained give shades varying from orange and red to bluish violet or blue and are characterized by the valuable property of dyeing viscose ra on in even shades. Certain dyestuffs of t e aforesaid type are already known but they have not 16 been described for the dyeing of viscose rayon and in particular it was not foreseen that they would have the valuable property of dyeing viscose rayon in'even shades.
I have found that regenerated cellulose ma- 20 terials may be dyed in even level shades by means of secondary disazo dyestufi's which may be represented by the following generic formula:
wherein R represents a coupled residue of a diazotized amine of the class consisting of chlor-aniline, amino-benzoic acid and anisidine, R represents a naphthalene residue and R represents a coupled residue of an azo dye coupling component of the class consisting of beta-naphthol, nitro-m-phenylene diamlne, salicylic acid and amino-naphthol sulphonic acids and m is 1 or 2. Within this generic class of dyes there are several subgeneric classes which are especially advantageous for dyeing regenerated cellulose materials in even level shades. The following structural formula indicate certain of these subgeneric classes which are typical. In the following formulae R R R and m have the same significance as above.
HOiS
11 April 19, 1929.
H by diazotizin 1 mol. of p-chloroaniline, coupling in a1 aline solution with 1 mol. of l 12 2-amino-8-naphthol-6-sulphonic acid, diazo- 159mb tizing the resultant aminoazo dyestuif and coupling in alkaline solution with 1 mol. of 2-amino-8 naphthol 6 sulphonic acid. 100 on NB, parts of the regenerated viscose rayon are GE entered into the bath warm and the bath is 13 then raised nearly to the boil and the dyeing carried on for about 4 hour. The fabric is then removed, rinsed and dried. Alternative- 0111 ly, the rayon may be entered into the bath nearly at the boil and allowed to cool gradually during the dyeing. Moreover, there may b th f ll i tr tu l f be also used in the dyebath, other salts or dye- It; following generic formulae, X ing assistants, as borax. The rayon 1s dyed --i-ogen or a sulphonic group, a violet brown shade. s chlorine, an alkoxy or a car- The invention 18 further and the other symbols have the examples in the following the subgeneric classes given generic classes which may be illustrated by the table:
with animo- End component (all couplings alkali l n us so uaapgltholsulphonlc acid are Shade oment 2-amino-5-naphthol-7-sulphonic acid Beta-naphtha] Orange Nltro-m-ghenoylonedlamme Oran e-red .L w lamino-B-naphthol-S-aulphonlc aeld Beta-nap th Redd sh-brown D0 Nltro-m-phenylenedlamine Red Do. ali ylic acid Bordeaux 1-amino-5-naphthol-7-sulphonlc acid 1:8-amIno-naphthol-2:4-dlsulphonlc acid Magenta 2-amino-5-naphthol-7-su1phonie acid l'amino-8-naphthol-2 4-disu1phonl c acid Blue-violet zamino-l-naphthol-d-sulphonlc acid l-amino-S-nuphthol-i-sulphonlc acid Bronze-violet use 1:S-aminonaplfifiplfi:fi-lillisglphoniegcld gaggarlllapgllaol IP/[eep b o n ic id 2-amino-8-na 0-6-5 on one c 1c moon 0 ac Do. p p Z-aln no-8-nephthol-8-sulphonic acid Prune ance as above unless otherwise Having now particularly described and ascertained the nature of my said invention and in what manner the same is to be performed, I declare that what I claim is 1. In the manufacture of dyed regenerated cellulose materials having an even level shade, the process which comprises applying to such regenerated cellulose materials a secondary disazo dyestufl' having in the form of the free acid the probable formula:
01H): 0:3)- wherein R represents the coupled residue of a diazotized amine of the class consisting of chloraniline, amino-benzoic acid and anisidine, R represents a naphthalene residue, and a; is 1 or 2, thereby dyeing said "regenerated NH: ::N
N=N- III H OaS x cellulose materials in even level shades.
H0 2. In the manufacture of dyed regenerated cellulose materials having an even level i W shade, the process which comprises applying to such regenerated cellulose materials a secl od!)- ondary disazo dyestufl having in the form of the free acid the probable formula:
Invention is illustrated, without limiti y the following examples in which the are by weight. N=N
pl I Q N=NR;,
l dyebath is made up from 3000 parts of x 20 parts of Glaubers salt, 3 parts of wherein R represents a coupled residue of and 2 parts of the dyestufi' obtained an azo dye coupling component of the class' a hydrogen or a sulphonic group,
wherein R, represents a Cl, an OCH or a COOH group and w is 1 or 2, thereby dyeing said regenerated cellulose materials in even level shades. I
4. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid the probable formula:
wherein R, represents a Cl, an OCH or a COOH oup, R represents a naphthalene residue, represents a coupled residue of an azo dye coupllng component of the class consisting of beta-naphthol, nitro-m-phenylene diamine, salicylic acid and amino-naphthol sulphonic acids, and m is 1 or 2, the said dyed regenerated cellulose .materials having even level shades.
5. As new products, regenerated cellulose materials dyed with disazo dyes having in the form 0 the free acid the probable formula":
0H NH: a,N=N- 1i.-N=N :QE
wherein R represents a coupled residue of a diazotized amine of the class consisting of chlor-aniline amlno-benzoic acid and anisidine, R and ill, represent a naphthalene residue, and w is 1 or 2, the said dyed regenerated cellulose having even level shades.
6. As new products, regenerated cellulose 'materials (1 ed with disazo dyes having in the form 0 the free acid the probable formula:
wherein R, represents a coupled residue of an azo dye coupling component of the class consisting of 2-amino-8-naphthol6-sulphonic acid, nitro-phenylene-meta-diamine, betanaphthol, and salicylic acid, and X represents hydrogen or a SO H group, the said dyed regenerated cellulose materials having even level shades.
7. As new products, regenerated cellulose materials dyed with disazo dyes having in thelform of the free acid the probable formu a:
N-N-ih-N-N-R:
wherein R represents a naphthalene residue, R represents a coupled residue of an azo dye coupling component of the class consisting of beta-naphthol, nitro-in-phenylene diamine, salicylic acid and ainino-naphthol sulphonic acids and m is 1 or 2, the said dyed regenerated cellulose materials having even level shades.
8. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid the probable formula wherein R represents a naphthalene residue,
R represents a coupled residue of an azo dye coupling component of the class consisting of beta-naphthol, nitro-m-phenylene diamine, salicylic acid and amino-naphthol sulphonic acids and w is 1 or 2, the said dyedregenerated cellulose having even level shades.
-9. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid the probable formula:
N=N i N=N- s-NH H o o a H 0 SOaH):
wherein R represents a naphthalene residue, and w is 1 or 2, the said dyed regenerated cellulose having even level shades.
10. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid theprobable formula:
said d ed regenerated cellulose having even level s ades.
11. As new products, regenerated cellulose with disazo dyes having in the form the free acid the probable formaterials d e mula H0 Q am no N= 3 no.8 01H the said dyed regenerated cellulose having even level shades.
12. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid the probable formula:
Q m no "a.
N=N x no: II
wherein X represents H or a SO,H group, '0 said dyed regenerated cellulose having even level shades.
13. As new roducts, regenerated cellulose (I with disazo dyes having in the materials dye form of the free acid the probable formula:
wherein R, represents a. naphthalene residue, R represents chlorine or an alkoxy group, and a: is 1 or 2, the said dyed regenerated cellulose having even level shades.
14. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid the probable formula:
wherein R, represents a coupled residue of an azo dye couplmg com onent of the class consisting of beta-napht ol, nitro-m-phen lene diamine, salicylic acid and amino-nap ithol sulphonic acids, R, represents chlorine, a carbox lie or alkoxy group, and X represents H or 0 H group, the said dyed regenerated cellulose having even level shades.
15. As new roduots, regenerated cellulose ed with disazo dyes having in materials dy the form of the free acid the probable formula:
Hols SOdEI the said dyed regenerated cellulose having even level shades.
16. As new roducts, regenerated cellulose materials (1 e with di-sazo dyes having in thel form 0 the free acid the probable formu a:
Q no the said dyed regenerated cellulose having even levelshad 17. -As new products, regenerated cellulose materials dyed with disazo dyes having the form of the free acid the probable formula:
Q nois wherein R, represents chlorine, or a COOH or OCH group, and R represents the coupled residue of an azo dye coupling component of the class consisting of beta-naphthol, nitro-phenylene-meta-diamine, salicylic acid, 2-amino-8-naphthol-6-sulphonic acid and 1 8 amino-naphthol-4-sulphonic acid, the said dyed regenerated cellulose having even level shades.
19. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid the probable formula:
' Ho's x KIN H0 00 OH wherein R represents chlorine or a COOH roup, the said dyed regenerated cellulose aving even level shades.
22. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid the probable formula:
IIO HO NH:
Q m to the said dyed regenerated cellulose having even level shades.
24. As new products, regenerated cellulose, materials dyed with disazo dyes having in the form of the free acid the probable formula:
H0 NH:
N: SOaH rims the said dyed regenerated cellulose having even level shades.
25. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid the probable formula:
HO|B NH! wherein R, represents a OCH Cl or COOH group, and a: is 1 or 2, the said dyed regenerated cellulose having even level shades.
26. As new products, regenerated cellulose materials dyed with disazo dyes having in the form of the free acid the probable formula N-N- r-OH wherein R represents a naphthalene residue, R, represents chlorine or an alkoxy grou and a; is 1 or 2, the said dyed regenerated cellulose having even level shades.
27. In the manufacture of dyed regenerated cellulose materials having an even level shade the process which comprises applying to such regenerated cellulose material certain secondary disazo dyestufl's, said disazo dyestufis having the probable formula: R1 N=N R2 N=NTR3 resents the alkaline-coupled residue of an amine of the benzene series of the class consistin of parachlor-aniline, meta-aminobenzolc acid and ortho-anisidine, R represents the alkaline-coupled residue of an amino-naphthol-sulphonic acid of the class consisting of 2-amino-5 naphthol-7-sulphonic acid, 2-amin0-8 naphthol-6-sulphonic acid, l-amino-fi-naphthol- -sul honic acid, 1 8-amino-napht-hol-3 6-disulplionic acid, the nitrogen of the amino group being one of the nltrogens forming part of the azo group between R and R and R represents the coupled residue of an azo dye cou ling component of the class consisting of tawherein R repmphthol, nitro-meta-phenylene-diamino, sallcyhq ac1 d, 1:8- am1no-na hthoI-2:4-disulphpmc acld, l-ampw-S-nap thol-4sulphonic 8.61 3, and 2-aImno-8-naphth01-6-si11phonic acl In testimony whereof I aflix my signature.
RAINALD BRIGHTMAN.
Certificate of Correction Patent No. 1,873,278. v August 23, 1932'.
' RAINALD BRIGHTMAN It is hereby certified that error appears in the printed specificationlof the abovenumbered pabent requiring correction as follows: Page 1, linesTO to 75, strike out the formula and insert and that the said should be mad with this eorrodion mad]; that the same may eonform to the record of the casein the Patent Oifice.
Signed and sealed this 11th day of October, A. D. 1932.
M. J. MOORE,
mphthol, nitro-meta-phenylene-diamino, sallcyhq ac1 d, 1:8- am1no-na hthoI-2:4-disulphpmc acld, l-ampw-S-nap thol-4sulphonic 8.61 3, and 2-aImno-8-naphth01-6-si11phonic acl In testimony whereof I aflix my signature.
RAINALD BRIGHTMAN.
Certificate of Correction PatentN0.1,873,278. r v August 23,1932.
RAINALD BRIGHTMAN It is hereby certified that error appears in the printed specificationlof the abovenumbered pabent requiring correction as follows: Page 1, linesTO to 75, strike out the formula and insert and that the said should be mad with this eorrodion mad]; that the same may eonform to the record of the casein the Patent Oifice.
Signed and sealed this 11th day of October, A. D. 1932.
M. J. MOORE,
US445227A 1929-04-19 1930-04-17 Dyeing of regenerated cellulose materials Expired - Lifetime US1873278A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1873278X 1929-04-19

Publications (1)

Publication Number Publication Date
US1873278A true US1873278A (en) 1932-08-23

Family

ID=10892517

Family Applications (1)

Application Number Title Priority Date Filing Date
US445227A Expired - Lifetime US1873278A (en) 1929-04-19 1930-04-17 Dyeing of regenerated cellulose materials

Country Status (1)

Country Link
US (1) US1873278A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2353605A1 (en) * 1976-05-31 1977-12-30 Sandoz Sa NEW 1: 2 METALLIC COMPLEXES, THEIR PREPARATION AND THEIR APPLICATION AS COLORANTS

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2353605A1 (en) * 1976-05-31 1977-12-30 Sandoz Sa NEW 1: 2 METALLIC COMPLEXES, THEIR PREPARATION AND THEIR APPLICATION AS COLORANTS
US4150942A (en) * 1976-05-31 1979-04-24 Sandoz Ltd. 1:2 Metal complexes of azo compounds having 1-hydroxynaphthalene-3-sulfonic acid coupling component radicals at least one of which is a disazo compound

Similar Documents

Publication Publication Date Title
US1505568A (en) Azo dyes insoluble in water and process of making same
US1867451A (en) Azo-dyestuffs and process of making same
US1873278A (en) Dyeing of regenerated cellulose materials
US2148659A (en) Process for the production of fast tints on cellulosic fibers
US2268919A (en) Polyazo dyestuffs and process of making same
US1594865A (en) Azo dyes derived from monoacylacetyl bodies and process of making same
US2156731A (en) Azo dyestuff insoluble in water and fiber dyed therewith
US3529984A (en) Mixtures of water-insoluble disazo dyestuffs and process for preparing them
US2061126A (en) Water-insoluble azo dyestuffs and fiber dyed therewith
US2468457A (en) Water-insoluble azo dyestuffs
US2092076A (en) Disazo dyestuffs and their production
US1898911A (en) Metalliferous azo-dyestuffs and process of making same
US1838270A (en) Azo dyestuffs from 2.3-hydroxynaphthoic acid arylids and process of making the same
US1766434A (en) Naphtho-carbazole-hydroxy-azo dyestuffs
US2028469A (en) Waterinsoluble azodyestuffs derived from benzocarbazoles
US1505569A (en) Azo dyes derived from acylacetyl compounds of diamins and process of making same
US2095484A (en) Azodyestuffs
US1992917A (en) Water-insoluble azo-dyestuff
US2023176A (en) Disazo dyestuffs
US2395135A (en) Pyrrole azo dyestuffs
US1694568A (en) Azo dyes and process of making same
GB295032A (en) Manufacture of strongly basic azo-dyestuffs
US1846546A (en) Azo-dyestuffs and process of making same
US2041851A (en) Azo dyestuffs and their production
US1871512A (en) Azo-dyes derived from naphthyl-aryl ethers