Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
  • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
  • D06L4/60—Optical bleaching or brightening
  • D06L4/657—Optical bleaching or brightening combined with other treatments, e.g. finishing, bleaching, softening, dyeing or pigment printing
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
  • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
  • D06L4/60—Optical bleaching or brightening
  • D06L4/664—Preparations of optical brighteners; Optical brighteners in aerosol form; Physical treatment of optical brighteners

Definitions

• the present invention relates to brightening agents; more particularly it concerns brightening agents of the 1,3- diarylor 1,3,5-triaryl-pyrazoline series.
• the 1,3-diarylor 1,3,5-triaryl-pyrazolines to be enployed as brightening agents according to the invention containing at least one sulfonamide group may be produced by various methods, for example by the action of ammonia or'amines on the corresponding aryl-pyrazolinesulfonyl chlorides.
• the production of the proposed brightening agents may also be carried out in a manner analogous to the known production of aryl-pyrazolines from aryl-hydrazines and a,B-unsaturated aryl ketone's or from their addition products with ammonia, amines, hydrogen halides or alcohols, from the corresponding starting components containing'sulfonarnide groups.
• the proposed brightening agents may beused in conventional manner at room temperature or at elevated temperatures. If the brightening agents are water-soluble, it is advisable to use them in the form ofan aqueous solution, if they are water-insoluble, they may be employed in the form of aqueous dispersions, possibly with the aid of dispersing agents. They may also be used in the form of solutions in organic solvents.
• the proposed brightening agents, particularly the compounds which are barely soluble in water, may also be incorporated in casting or spinning melts or solutions used for the production of synthetic articles such as foils, fibres of filaments. The quantities required for brightening may vary within wide limits; they can readily be established by preliminary experiments.
• the brightening agents to be employed according to the invention are suitable for brightening a great variety of materials such as textile fabrics, paper, leather or soaps. They are especially suitable for brightening wool and synthetic fibres, particularly in combination with washing f'T-E EFEREliCE agents. Thebrightening effects obtained possess good fastness to light.
• the aryl pyrazolines of the present invention which contain sulfonamide groups exhibit improved brightening elfects, especially on synthetic fibres, particularly when applied in a neutral bath;
• a very advantageous embodimentof the present invention consists in adding the proposed brightening agents to casting or spinning masses which contain acrylonitrile polymers or copolymers.
• the filaments, fibres, foils or other articles which can be produced in known manner from these casting or spinning masses mixed with the brightening agents of the invention exhibit a brightening effect which has heretofore never been obtained in articles containing acrylonitrile polymers or copolymers and which is excellently stable to light and washing.
• Example 1 Laundry goods consistiiig of polyamide fibres, acetate rayon and wool, and exhibiting a yellowish appearance, are washedin the usual manner with a suitable washing powder combination which contains 0.1 percent of 1-psulfonamidophenyl 3 p-chlorophenyl-pyrazoline. Even after washing-only once, the articles treated show a purewhite appearance. i
• the l p-sulfonamidophenyl-S-p-chlorophenyl-pyrazoline having a melting point of 218 C. was prepared from p-chlorophenyi-fl-chloroethyl ketone and p-liydrazinebenzene-sulfonamide' in methanolic solution in the pres ence of pyridine.
• Example 2 Laundry goods of cellulose fibres, polyamide fibres, acetate rayon and wool are washed at a temperature of about 40 C. with a conventional household washing agent which contains (possibly in addition to oxygenyielding compounds) 0.05 percent of l-p-sulfonamidophenyl 3 p-bromophenyl-pyrazoline.
• the brightening agent in contrast to other brightening agents, for example those based on amino-stilbene-disulfonic acids, does not go on cellulose-containing fibres in the first instance, but mainly on the laundry goods made of polyamide fibres, acetate rayon and wool, so that these show an excellent brightening effect.
• the lesserafiinity for cellulose fibres may be of advantage, when cotton articles having delicate pastel shades are washed at the same time with other goods; thus no undesirable change of colour will occur.
• the brightening agent used having a melting point of 220 C. was prepared from p-brornophenyl-fl-chloroethy] ketone and p-hydraZine-benzene-sulfonamide.
• Example 3 10,000 parts ofcurd soap, soapneedles and soap flakes are intimately mixed with one part of 'rl-p-sulfonamidophenyl-3-p tolyl'-pyrazoline at any time during their manufacture.
• the soap products having intially a yellowish appearance obtain in this manner a pure white appearance.
• the brightening agent usedhaving a melting point of 257 C. was prepared from p -tolyl-B-chloro-ethyl-ketone and p-hydrazino-benzene-sulfonamide.
• Example 4 7 10,000 parts of soap based on fatty acids or synthetics ShiiiiCi'i iillilh'i or mixture of both types are intimately mixed with about parts of 1-p-sulfanilidophenyl-3-p-chlorophenyl-pyrazoline.
• the soaps thus obtained show an excellent brightening effect.
• Laundry goods of polyamide fibres, acetate rayon or wool washed with these soaps also show an excellent brightening effect. It should be noted that none of the effects known as colour accumulation occurs, even if the soap is constantly used.
• the 1 p sulfanilidophenyl 3 p chlorophenylpyrazoline was prepared from l-p-sulfanilidophenylhydrazine and p-chlorophenyl-B-chloroethyl ketone; the melting point is 202 C.
• Example 5 10,000 parts of a soap base siutable for the manufacture of toilet soaps are treated in a mixing apparatus, prior to working up in a soap mill, with 3 parts of the brightening agent described below. During this process, other customary ingredients such as perfumes, anti-oxidants, deodorants or white pigments, may also be added to the soap. A pure-white appearance is thus imparted to the intiially pale cream coloured soap. When colours are also employed, the shades become clearer and more brilliant.
• the brightening agent empoyed was prepared in the following manner:
• 1,3-diphenyl-pyraz0line 30 part of 1,3-diphenyl-pyraz0line were added with cooling to 70 parts of chlorosulfonic acid, after the mixture was allowed to stand at room temperature for one hour, it was poured onto ice.
• the 1,3-diphenyl-pyrazoline-sulfochloride thus separated was filtered off with suction. 7 parts of the 1,3-diphenyl-pyrazo1ine-sulfochloride thus obtained were then boiled under reflux with 6 parts of N-methylaminoethane-sulfonic acid in 70 parts of acetone. Thereupon, 1,3-diphenyl-pyrazoline-sulfomethylaminoethane-sulfonic acid separated out as a light yellow powder.
• Example 6 When rinsing laundry goods of olyamide fibres, acetate rayon and wool, 0.02 gram per litre of the brightening agent 1-p-sulfonamidophenyl 3 p methoxy-phenylpyrazoline of M.P. 228 C. obtainable from p-methoxyphenyl-B-chlorethyl ketone and p-hydrazine-benzene-sulfonamide is added to one of the rinsing baths.
• the brightening agent may be used directly or in compounded form, i.e. as a tablet or powder, in admixture with complex phosphates, Glaubers salt, bicarbonates or the like.
• the non-coloured laundry goods of the above-mentioned types of fibre become pure white through the action of the brightening agent, whilst the colours of the laundred articles become more brilliant.
• Example 7 Polyamide fibres, acetate rayon, wool or silk bleached in conventional manner are impregnated with a liquor containing 0.05-0.2 gram per litre of l-p-sulfonamidophenyl-3,S-diphenyl-pyrazoline as brightening agent; the liquor may also contain cation-active softening and finishing agents. The fabrics are then dried. The white shade of the goods thus obtained is distinctly brighter and more brilliant than that obtained without the use of the brightening agent.
• the brightening agent employed having a melting point of 209 C. may be prepared from benzal-acetophenone and p-hydrazino benzene-sulfonamide in alcoholic acetic solution.
• Example 8 The brightening agent described below is dissolved by pouring boiling water over it; sufl'icient of this solution is then introduced into an aqueous bath for brightening wool or polyamide fibres that the bath, using a liquor-t0- goods ratio of 40:1, contains 0.03-3 percent of the brightening agent referred to the weight of the goods.
• Prep-hydrazinobenzene-sulfonic viously, 3-percent of formic acid (85%) was added to the bath.
• the pre-wetted textile material is then placed in the bath at about C.; the bath temperature is now slowly increased to 50-60 C. and the textile material is moderately agitated in the liquor at this temperature for about 20 minutes. The textile material thus treated is very well brightened.
• the brightening agent employed is l-p-(sulphonyl-fimorpholino ethylamido) phenyl 3 p chlorophenylpyrazoline prepared from p-chlorophenyl-[3-chlorethyl ketone and p-hydrazino-benzene-sulfonic acid-,H-morpholinoethyl-amide.
• Example 9 Greyish white or undyed textiles of polyamide fibres, acetate rayon or wool, which have turned somewhat yellow in storage or possibly in use, are treated at 4050 C.
• the aforesaid pyrazoline compound serving as brightening agent and having a melting point of 233236 C. was obtained from m,p-dichlorophenyl-B-chlorethyl ketone and p-hydrazino-benzene-sulfonamide.
• Example 10 In 750 parts of dimethyl formamide are first dissolved 0.25 part of 1-p-sulfonamidophenyl-3-p-chlorophenyl-pyrazoline, prepared from p-chlorophenyl-fi-chlorethyl ketone and p-hydrazino-benzene-sulfonamide in methanolic solution in the presence of pyridine, and then 250 parts of polyacrylonitrile of K-value with heating and stirring. The solution thus obtained is then spun in usual manner according to the dry-spinning process so that the filaments after stretching in soiling water by 300 percent have a titre of about 3 denier. The filaments thus obtained are pure white in diffuse daylight, whilst filaments prepared in a comparable manner without the addition of the brightening agent exhibit a yellowish white shade.
• halogen-phenyl lower alkyl-phenyl, and alkoxy-phenyl; 2.
• Y is a member of the group consisting of hydrogen and 3.
• Z is a member of the group consisting of phenyl-3-p-chlorophenyl-pyrazoline.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Coloring (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Cited By (6)

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• 0
  • BE BE555431D patent/BE555431A/xx unknown
  • NL NL97340D patent/NL97340C/xx active
• 1956
  • 1956-03-03 DE DEF19683A patent/DE1080963B/de active Pending
• 1957
  • 1957-02-16 CH CH355763D patent/CH355763A/de unknown
  • 1957-03-01 FR FR1172759D patent/FR1172759A/fr not_active Expired
  • 1957-03-01 GB GB6873/57A patent/GB808113A/en not_active Expired
• 1962
  • 1962-05-15 US US194999A patent/US3135742A/en not_active Expired - Lifetime

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