US3157633A - Polyethyleneoxy fugitive tints - Google Patents

Polyethyleneoxy fugitive tints Download PDF

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Publication number
US3157633A
US3157633A US71926A US7192660A US3157633A US 3157633 A US3157633 A US 3157633A US 71926 A US71926 A US 71926A US 7192660 A US7192660 A US 7192660A US 3157633 A US3157633 A US 3157633A
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fugitive
compounds
compound
produce
tints
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Hans H Kuhn
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Deering Milliken Research Corp
Milliken Research Corp
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Milliken Research Corp
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Priority to US71926A priority Critical patent/US3157633A/en
Priority to GB38387/61A priority patent/GB996068A/en
Priority to CH1331661A priority patent/CH372275A/fr
Priority to BE610527A priority patent/BE610527A/fr
Priority to NL271885D priority patent/NL271885A/nl
Priority to DE19611419801 priority patent/DE1419801A1/de
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/13—Fugitive dyeing or stripping dyes
    • D06P5/138—Fugitive dyeing or stripping dyes fugitive dyeing
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass

Definitions

  • the fugitive tinting of textile materials to assist in fiber, yarn, thread or fabric identification, e.g., during weaving or knitting operations or prior thereto, is a well known and universally practiced art.
  • Commonly employed are dyestuffs having marginal affinity to certain fibers, usually compounded with materials to further reduce their dyeing ability.
  • Also employed are dyestuffs which, although satisfactory dyestuffs for certain fibers, have lesser afiinity for other unrelated fibers.
  • these dyestuffs are accompanied by the risk that if the textilematerial is subjected to certain conditions, e.g., heating, drying or steaming, etc., the dyestufi may dye the fiber or, if a blend is employed, the dyestulf will bleed onto the untinted fiber and permanently dye it. Even under normal conditions, many of the fugitive tints commonly employed are removed only with great difliculty and prolonged scouring. Furthermore, as each new blend of fibers is contemplated, testing is required to determine if the selected tint will permanently dye one or more components of the blend under any or all conditions.
  • novel compounds of this invention are characterized by being water soluble polymeric surfactants having at least 30 repeating ethyleneoxy units in the molecule, a molecular weight of at least 1,000 and having a dyestuif molecule attached to the polymeric chain, said compounds being fugitive tints for at least Dacron polyester, Orlon polyacrylonitrile, cotton and cellulose acetate as well as other textile fibers.
  • fugitive tints of this invention are characterized by the general formula wherein R is a dyestulf radical, n is at least 15, x is from 1 to 6, and the product of n times x is at least 30, prefer- 3,157,633 Patented Nov. 17, 1964 ably between 50 and 200, more preferably between about 75 and 150.
  • the compounds of this invention are universal fugitive tints, i.e., can be used as fugitive tints for substantially all textile fibers under one or more of the following conditions:
  • Textile materials which can be temporarily colored with the fugitive tints of this invention include staple, fibers, tops, roving, sliver, filaments, yarns, threads and woven or knitted yarn goods or garments. These fugitive tints are also useful in the staining or temporary coloring of non 'textile fibrous materials, e.g., paper and paper products, and can be used as washable inks or water colors.
  • R is attached by an amino nitrogen.
  • Compounds contemplated within this general class are those wherein R is a nitroso, nitro, azo, including monoazo, diazo and trisazo, diphenylmethane, triarylmethane, Xanthene, acridene, methine, thiazole, indamine, azine, oxazine, or anthraquinone dyestulf radical.
  • R-N is an organic dyestuif radical
  • x is from one to two
  • a second class of preferred polyethyleneoxy fugitive tints of this invention are the anthraquinoncs, e.g., those which can be represented by the formula wherein x and y are nuclear substituents selected from the group consisting of hydrogen, amino, hydroxy, halo, nitro, COO-alkali-metal and -SO -alkali-metal, and n is at least 30, preferably between 30 and 200, and z and z are a total of from one to four, e.g., z is one and z is 0, z and z are each 1, z is one and z is two, and z and z are both two, and the corresponding N,N-dil1ydroxyethylpolyethylene-oxy compounds.
  • preferred amongst this class are those wherein at least one and preferably two of x and y are a sulfonic acid radical.
  • fugitivity on wool of the abovedescrib'ed class of fugitive tints improves as the number of ethyleneoxy groups in the molecule increases and the best fugitive tints for materials containing wool fibers are those wherein at least 50 ethyleneoxy groups, and preferably at least 75 to 1 ethyleneoxy groups, are in the molecule.
  • the tintorial power of the resulting fugitive tint is necessarily reduced.
  • the number of ethylencoxy groups be less than about 200, and more preferably less than about 150.
  • the compounds of this invention tend to be most highly fugitive towards cotton fibers when the number of ethyleneoxy groups in the molecule is relatively low, e.g., from 30 to 75. Also as the size and complexity of the dyestulf radical increases, the number of ethyleneoxy groups which must be present to pass Test C, abovedescribed, tends to increase. This tendency is offset by the presence of sulfonyloxy groups in the dyestuft' radical, as stated above.
  • the compounds of this invention are preferably prepared by converting an intermediate in the production of dyestuffs containing a free amino group to the corresponding polyethyleneoxy compound and employing the resulting compound to produce a compound having a chromophoric group in the molecule.
  • azo dyestuffs this can be accomplished by reacting a primary or secondary aromatic amine, preferably the former, with ethyleneoxide according to procedures well known in the art, and then coupling the resulting compound with a diazonium salt of an aromatic amine.
  • dyestuffs e.g., the anthraquinones, having chlorine, bromine or iodine attached to the aromatic nucleus can be reacted with excess polyethylene glycol monoamine of the formula H (OCH CH -NH;
  • n is at least 30, according to procedures known in the art to produce the corresponding secondary amine.
  • the polyethyleneoxy group can be introduced in other ways to produce fugitive tints of this invention.
  • anthroquinone-Z-carboxylic acid can be reacted with a molar excess of a polyethylene glycol having a molecular weight above about 1350, e.g., in the presence of p-toluene-sulfonic acid in a suitable solvent, e.g., dioxane or nitro-benzene, to product the corresponding polyethylene glycol monoester of anthraquinone-Z-carboxylic acid.
  • the reaction can also be conducted on other anthraquinone carboxylic acids containing one or more additional chromophoric or other non-interfering groups in the molecule.
  • An aromatic amine e.g., aniline or nuclear substituted aniline
  • a polyethylene glycol as described above under pressure at a temperature of about 220 C. to 230 C., preferably in the presence of iodine or a copper or sodium halide as a catalyst.
  • the resulting amine e.g., the polyethylene glycol substituted aniline
  • An aromatic bromo compound e.g., Z-bromo-anthraquinone
  • Z-bromo-anthraquinone can be reacted with polyethylene glycol in the presence of sodium at 159 C. to produce the corresponding anthraquinonc polyethylene glycol ether.
  • a nitrophenol e.g., p-nitrophenol, can be reacted with polyethylene glycol in the same manner to produce the p-nitrophenol polyethylene glycol ether.
  • This compound can then be reduced by any of the methods Well known in the art for reducing aromatic nitro groups, e.g., zinc and acetic acid, hydrogen and catalyst, to produce the corresponding p-amino compound which can then be diazotized and coupled with a suitable aromatic compound, e.g., H acid, to produce a fugitive tint of this invention.
  • aromatic nitro groups e.g., zinc and acetic acid, hydrogen and catalyst
  • the polyethyleneoxy fugitive tints of this invention possess the unique property of being rendered temporarily substantially water-insoluble or much less soluble by reaction with Water-soluble polyacrylic acid or similar watersoluble polyacid, whereas the corresponding compounds containing, e.g., 2 to 10 ethyleneoXy groups, are not insolubilized.
  • This unique property means that fibers tinted with a fugitive tint of this invention can be contacted with an aqueous solution of one of the above-described polyacid and insolubilized in situ.
  • wool, nylon or other fibers commonly sized with polyacrylic acid can be tinted with the fugitive tints of this invention, mixed with other fibers, yarns or threads, etc., and then passed into an aqueous solution of one of the above-described polyacids, e.g., in a slashing operation, and no bleeding of the tint or tints onto the untinted fibers will occur.
  • This insolubllization can then be reversed with acetones or other ketonic solvent or with a mild detergent scour. It will be apparent to one skilled in the art that this unique property of the fugitive tints of this invention will solve many of the problems presently experienced when using fugitive tints prior to a slashing operation.
  • each of the N,N-dihydroxyethyl amines employed herein can be prepared from the corresponding primary amine and ethylene oxide.
  • N,N-dihydroxyethylaniline and N,N-dihydroxyethyl-m-toluidine are solids.
  • N,N-dihydroxyethyl-2,S-dimethoxyaniline is a liquid.
  • the reaction can be conducted in an inert solvent, preferably boiling in the range of 100 C. to 150 C., e.g., nitrobenzene, xylene, or dioxane, the dimethyl ether of ethylene glycol, or a portion of the desired reaction product, or in ethylene oxide in an autoclave under pressure.
  • an inert solvent preferably boiling in the range of 100 C. to 150 C., e.g., nitrobenzene, xylene, or dioxane, the dimethyl ether of ethylene glycol, or a portion of the desired reaction product, or in ethylene oxide in an autoclave under pressure.
  • PREPARATION III The procedure of Preparation II was followed, employing N,N-dihydroxyethyl-aniline and'enough molar equivalents of ethylene oxide to produce compounds having the formula wherein n and a each are about 6, 10, 15, 22, 35 and 50. The latter three compounds melt at 34 C., 47 C., and 50 C., respectively. The reaction was also continued until a compound was produced melting at 56.5 C. in which n and n were about 115.
  • aromatic primary amines e.g., those having one or more of a chloro, nitro, lower-alkyl and lower-alkoxy substituents on the aromatic ring, but at least one unsubstituted position to permit coupling, can be converted to the corresponding N,N-dihydroxyethylpolyethyleneoxy-tertiary amines which can then be converted to fugitive tints having the azo chromophoric group according to the procedures described in the examples hereinafter.
  • Example I Dissolve 1,127 g. (0.3 mol) of a compound prepared according to Preparation 11 wherein n and a each are about 40 in an equal amount, of water and add at 0 C. to a solution of 42.3 g. (0.3 mol) of a diazonium salt of aniline. Maintain the reaction mixture at that temperature for 15 minutes and then allow it to rise at room temperature.
  • azonium salt has reacted (about 2- hours) make the solu- A solution of a yellow fugitive tint is obtained which can be isolated by evaporation of the water. Similar fugitive tints are obtained by substituting the corresponding com pound wherein n and n are about 40.
  • Example II Following the procedure of Example I, employing the diazonium salt of sulfanilic acid and the compounds of Preparation II wherein n and it each are about 5, 15 and 50. Yellow compounds are obtained, the latter two being fugitive tints.
  • Example Ill follow the procedure of Example I, using the diazonium salt of aniline-2,5-disulfonic acid and the compounds of Preparation II wherein n and a each are about 50.
  • Example IV Following the procedure of Example I, employing diazonium salt of naphthylamine-3,6,8-trisulfonic acid and the compound prepared according to Preparation II wherein n and n each are about 5, 15 and 50. Salmon colored compounds are obtained, the latter two being fugitive tints.
  • Example V follows the procedure of Example I, employing the diazonium salt of 1,8-naphtholamine-3,6-disulfonic acid and the compounds of Preparation II wherein n and a each are about 5, 15 and 50. Red products are obtained, the latter two being fugitive tints.
  • Example VI follows the procedure of Example I, employing the diazonium salt of aniline and the compounds prepared according to Preparation III wherein n and n are about 2, 22, 36, 50 and 115. Yellow compounds are obtained, all except the first being fugitive tints.
  • Example VII Following the procedure of Example I, employing the diazonium salt of p-nitroaniline and the compounds prepared according to Preparation III wherein n and n each are about 45. A red fugitive tint is obtained.
  • Example VIII follows the procedure of Example I, employing the diazonium salt of sulfanilic acid and compounds prepared according to Preparation IV wherein n and 21 each are about 2, and 50. Salmon colored compounds are obtained, all except the first being fugitive tints.
  • Example IX follows the procedure of Example I, employing the diazonium salt of 1,8-naphtholamiue-3,S-disulfonic acid and compounds prepared according to Preparation 1V wherein n and it each are 5, l5 and 50. Reddish-purple compounds are obtained, all except the first being fugitive tints.
  • Example X follows the procedure of Example I, employing the diazonium salt of 1,8-naphtholamine-3,6-disulfonic acid and the compound prepared according to Preparation V. A purple fugitive tint is obtained.
  • Example XI follows the procedure of Example XI but employ N,N-
  • Example XII Hydrogenate the N,N-di-hydroxyethylpolyethyleneoxyp-nitroanilines prepared according to the procedure of EX- ample XI with hydrogen and Raney nickel catalyst in water. Alternatively, this reduction can be conducted according to any of the common methods for reducing aromatic nitro compounds. See Wagner and Zook, Synthetic Organic Chemistry, Wiley Publishers, page 654 (1953). There is thus produced N,N-di-hydroxyethylpolyethyleneoxy-p-phenylenediamines containing about and about 90 ethyleneoxy groups, respectively.
  • These compounds can be diazotized with sodium nitrate in the usual fashion to produce the corresponding diazonium salts and then reacted with, e.g., aniline, naphtholaminedisulfonic acid, naphthylaminedisultonic acid, to produce fugitive tints.
  • Example XIII React the sodium salt of 1-arnino-4-bromo-anthraquinone2-sulfonic acid in aqueous solution with a large molar excess of polyethylene glycol 2,000 monoamine at -90 C., in the presence of sodium carbonate and copper sulfate, until the reaction is substantially complete. There is thus obtained a bright blue fugitive tint having the formula (M) NH,
  • n is about 45.
  • Purification can be accomplished by chromatography with activated aluminum oxide or other suitable means.
  • Example XIV follows the procedure for the preparation of Cl. Disperse Yellow 9 (Colour Index No. 10375) but substitute on equal molar amount of the compound prepared according to Example XIV wherein n and n are about 46 for the phenylene diamine to produce a compound having the formula (CH CH OMII (CIIZCLHOLJI wherein n and n are about 46.
  • Example XV Couple the diazonium salt of 1,8-naphtholamine-3,6- disulfonic acid with naphthylamine.
  • a dyestutf is obtained which is diazotized with sodium nitrite and coupled to the toluidine-ethylene oxide addition product containing about 100 molar equivalents of ethylene oxide, prepared as described in Preparation II.
  • Example XVI Couple K acid (naphtholamine-disultonic acid) on the acid side with the diazotized N,N-di-hydroxyethylpolycthyleneoxy-p-phenylenediamine containing about ethyleneoxy groups. Couple this compound with benzidine and then couple the reaction product with phenol, according to the procedure for the preparation of the CI. Direct Green (CI. 30225), to produce a triazo fugitive tint having the formula wherein n and n are about 46.
  • Example XVII React p,p'-methylene-bis-aniline with ethylene oxide in the manner described in Preparations I and II so as to add about 80 molar equivalents of ethylene oxide thereto.
  • Example XIX React m-chloroaniline with ethylene oxide according to the procedures of Preparations I and II so as to produce N,N di-hydroxyethypolyethyleneoxy-m-chloroaniline containing about 50 ethyleneoxy groups. React the thus produced compound with sodium hydroxide to produce N,N-di-hydroxyethylpolyethyleneoxy-m-hydroxyaniline, according to the procedures well known in the art.
  • Example XX follows the procedure for the preparation of Acridine Orange R (Cl. 46,055) but substitute N,N-di-hydroxyethylpolyethyleneoxy-m-aminoaniline, prepared as described in Example XIV, and containing about 70 ethyleneoxy groups, for the N,N-dimethyl-m-phenylenediamine.
  • Example XXI Prepare the ethylene acetal of p-nitrobenzaldehyde with p-nitro-benzaldehyde and a large molar excess of ethylene glycol in refluxing benzene with water take off, in the presence of p-toluenesulfonic acid catalyst. Reduce the resulting acetal with lithium aluminum hydride in ether or by catalytic hydrogenation to produce the ethylene acetal of p-aminobenzaldehyde. React this compound with ethylene oxide according to the procedures of Preparations I and II to produce the ethylene acetal of N,N di hydroxyethylpolyethyleneoxy-p-aminobenzaldehyde containing about 70 ethyleneoxy groups. I-lydrolyze this compound in water containing a trace of hydrochloric acid at room temperature to produce the free aldehydic compound.
  • Example XXII React Primuline base with ethylene oxide according to the procedures of Preparations I and II until about 150 moles of ethylene oxide have been absorbed. A fugitive yellow tint is thus produced.
  • Example XXIII Condense lLN-dimethyl-p-nitrosoaniline with the N,N- di-hydroxyethylpolyethyleneoxy-aniline prepared according to the procedure of Preparation III wherein n and n are about 35, according to the procedure for the preparation of Bindschedlers Green (Cl. No. 49,405), to produce a compound having the formula wherein n and n are about 36.
  • Example XXIV Oxidize a mixture of the N,N-di-hydroxyethylpolyethyleneoxy-p-phenylenediamine described in Example XIV, and containing about ethyleneoxy groups, and l-naphthol in aqueous alkaline solution by atmospheric oxygen according to the procedure for the preparation of Cl. Solvent Blue 22 (Cl. 49,705). A blue fugitive tint is thus prepared having the formula wherein n and n are about 36.
  • Example XXV Following the procedure for the preparation of Cl. Basic Red '5 (GI. No. 50040) and oxidize a mixture of N,N-dihydroxyethylpolyethyleneoxy p phenylenediamine contaming about 90 ethyleneoxy groups, prepared according to the procedure of Example XIII, and toluene-2,4-diamine vto produce.a .red fugitive tint having the formula N V -OH;
  • n and It are about 46.
  • Example X X VII Convert N,N-di-l1ydroxyethylpolyethyleneoxy-p-phenylenediamine, containing about 90 ethyleneoxy groups, to the corresponding nitroso hydrochloride in the usual manher and react an excess of this compound with m-dimethylaminophenol in the same manner as the preparation of Capri Blue GN (CI. 51000) to produce a blue fugitive tint having the formula wherein n and n are about 46.
  • Example XXI Ill Condense Meldolas Blue (CI. 51175) with the N,N- di-hydroxyethylpolyethyleneoxy-p-phenylenediamine containing about 90 ethyleneoxy groups, in the same manner as for the preparation of Cl. Basic Blue (CI. 51190), to produce a blue fugitive tint having the formula wherein n and n are about 46.
  • N-mono-substituted aromatic amines and other tertiary hydroxyethyl substituted amines can be reacted with ethylene oxide to produce corresponding polyethyleneoxy compounds and then coupled with diazonium compounds to produce fugitive tints of the formula e.g., lower alkyl, aryl or aralkyl containing from six to twelve or more carbon atoms, e.g., pehnyl, tolyl, benzyl, or
  • Compounds of this invention can also be prepared by reacting a compound of the formula wherein n has the value given before, R is lower-alkyl, aryl or aralkyl containing from six to twelve or more carbon atoms, or (CH CH O) H as refined above, and R" is an aromatic group, usually carbocylic, e.g., phenyl or napthyl, e.g., chloro, nitro, methoxy, and other substituents in, e.g., the meta position, but having at least one unsubstituted and reactive position, with sodium nitrite and an acid, e.g., hydrochloric acid, to add the -NO.
  • R is lower-alkyl, aryl or aralkyl containing from six to twelve or more carbon atoms, or (CH CH O) H as refined above
  • R" is an aromatic group, usually carbocylic, e.g., phenyl or napthyl, e.g
  • N,N di hydroxyethylpolyethyleneoxyaniline containing about ethyleneoxy groups is reacted in dilute hydrochloric acid with cooling with a molar equivalent of sodium nitrite to produce N,N-di-hydroxyethylpolyethyleneoxy-p-nitrosoaniline, a yellow fugitive tint.
  • the nitroso group can also be reduced in the usual fashion to a primary amine group which can then be coupled with diaotized amines to produce azo fugitive tints.
  • a water soluble fugitive tint compound of the formula I R1 RN wherein R is an organic dyestuff radical, R is a member selected from the group consisting of hydrogen, lower alkyl, aryl and aralkyl containing from six to 12 carbon atoms, and (CH CH O) H, n is at least 15, x is from 1 to 6, and the product of n times x is at least 30.
  • R is -(CH CH O) H, x is 1 and n is an integer between 25 and 100.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US71926A 1960-11-28 1960-11-28 Polyethyleneoxy fugitive tints Expired - Lifetime US3157633A (en)

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Application Number Priority Date Filing Date Title
US71926A US3157633A (en) 1960-11-28 1960-11-28 Polyethyleneoxy fugitive tints
GB38387/61A GB996068A (en) 1960-11-28 1961-10-26 Fugitive dyestuffs
CH1331661A CH372275A (fr) 1960-11-28 1961-11-16 Procédé pour la teinture fugace de fibres textiles
BE610527A BE610527A (fr) 1960-11-28 1961-11-20 Nouveaux colorants fugaces pour matières textiles.
NL271885D NL271885A (nl) 1960-11-28 1961-11-28 Werkwijze voor het bereiden van kleurstoffen met een tijdelijk kleurenkarakter, alsmede voor het tijdelijk kleuren van textielmaterialen
DE19611419801 DE1419801A1 (de) 1960-11-28 1961-11-28 Verfahren zur Herstellung von wasserloeslichen,unechten Faerbemitteln fuer Textilfasern mit oberflaechenaktiven Eigenschaften

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US4113721A (en) * 1975-09-02 1978-09-12 Milliken Research Corporation Water-soluble, non-polar solvent-soluble ethyleneoxy-propyleneoxy containing fugitial tints
US4137243A (en) * 1976-08-24 1979-01-30 Milliken Research Corporation Polymeric anthraquinone derived colorants
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US4167510A (en) * 1976-09-07 1979-09-11 Milliken Research Corporation Ester capped alkyleneoxy fugitive tints and method for producing same
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US5250708A (en) * 1991-08-13 1993-10-05 Milliken Research Corporation Poly(oxyalkylene) substituted aminophenol intermediate and xanthene colorant
US5290921A (en) * 1990-01-08 1994-03-01 Milliken Research Corporation Intermediates and colorants having primary hydroxyl enriched poly (oxyalkylene) moieties and their preparation
US5331097A (en) * 1991-08-13 1994-07-19 Milliken Research Corporation Poly(oxyalkylene) substituted xanthene colorant and method for making the same
US5387745A (en) * 1983-02-07 1995-02-07 Milliken Research Corporation Process for identifying a location to which an agrochemical has been applied
US5456725A (en) * 1994-03-04 1995-10-10 Milliken Research Corporation Method for temporarily coloring textile fibers
US5591833A (en) * 1990-06-28 1997-01-07 Milliken Research Corporation Colorants and intermediates therefor having branched poly(oxyalkylene)moieties, and their manufacture
EP0755687A1 (en) 1995-07-17 1997-01-29 Milliken Research Corporation Opacified aqueous composition for toilets
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GB996068A (en) 1965-06-23
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CH372275A (fr) 1963-11-30
NL271885A (nl) 1964-07-27

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