The method of producing a liquid composition containing the compounds of the stilbene

 

(57) Abstract:

Describes a method of producing a liquid composition containing the compound of stilbene General formula (I)

where R1means phenylamine, -N(C2-4-hydroxyalkyl)2or the balance of amino acids, which split the hydrogen atom on the amino group; R3-phenylamino possibly substituted-COR, where R is a C1-3-alkyl or NH(C1-4-alkyl; M Is Na by reacting the acid chloride cyanuric acid disodium salt, 4,4'-diaminostilbene-2,2'-disulfonate and consistent substitution of chlorine atoms for residues R1and R3and the whole process is carried out in a medium of water and polyglycol when the mass ratio of the last from 10:90 to 90:10 in the presence of sodium carbonate at stage I of the process. The described method allows to simplify the process to reduce the formation of by-products and to obtain a stable composition of the fluorescent whitening tools for various applications in the field of paper, textiles, detergents and cosmetics. 7 C.p. f-crystals.

The present invention relates to a method of producing a liquid composition containing stilbene compounds, in particular, 4,4'-bis-(creatininemia)-stilbene-2,2 and 4,4'-bis-(creatininemia)-stilbene-2,2' -disulfonate, which, in turn, is produced by the initial interaction 4,4'-diaminostilbene-2,2'-disulfonate with acid chloride cyanuric acid and subsequent replacement of the remaining chlorine atoms nucleophiles (see, e.g., “Fluorescent Whitening Agents”, R. Aniiker and G. , G. Thieme Publishers, 1975. p.31 ff.). Derivatives of stilbene used as fluorescent whitening tools. However, as described in the above link, there are cases of undesirable by-products, especially during the final stages of the reaction (that is, during the replacement of the third chlorine atom of the cyanuric acid chloride acid), when required higher temperatures, longer periods of interaction, high blood pressure and possibly an excess of amines.

Surprisingly it was discovered recently that this stage of the reaction can be performed more efficiently if the interaction of the components is carried out in a medium containing a mixture of water and polyglycol. An additional advantage of this method is that the resulting reaction mixture is a stable composition of fluorescent whitening means that, if required, can be the about of the invention is a method of producing a liquid composition, containing 4,4'-bis-(creatininemia)-stilbene-2,2'-disulfonato formulas (1)

where R1means phenylamine, -N(C2-C4-hydroxyalkyl)2or the balance of amino acids, which split the hydrogen atom on the amino group;

R3- phenylamino, possibly substituted-COR, where R is a C1-C3-alkyl or NH(C1-C4-alkyl);

M-Na, which consists in the interaction of the acid chloride cyanuric acid with 4,4'-diaminostilbene-2,2'-dissolvability in the presence of sodium carbonate to obtain the intermediate compounds of formula (2)

which is then subjected to interaction with the compound of the formula R1H, where R1has the above values, equimolecular quantities relative to the acid chloride cyanuric acid to obtain the compounds of formula (3)

with the subsequent interaction of the compound (3) with the compound of the formula R3N, where R3has the above values, and the process is carried out in a medium containing a mixture of water and polyglycol when the mass ratio of water and polyglycol from 10:90 to 90:10.

The final product of formula (1) may contain from 1 to 20%, preferred is Dorota group-HE is.

The reagents are typically used essentially in the stoichiometric proportions required for the formation of compounds of formula (1).

Polyglycol preferably has a molecular weight of about 200-5000 and more preferably is a polyethylene glycol having a molecular weight of about 200-1500.

Other polyglycols, which can be used in the proposed method, are block copolymers of ethylene oxide and propylene oxide, which can be represented by the formula

N-(OCH2CH2)and-(O-CH(CH3)-CH2)b-(OCH2CH2)andHE

where a denotes a number from 0.5 to 230 and b denotes a number from 15 to 80.

These block copolymers are also suitable for various applications in the field of paper, textiles, detergents and cosmetics.

Relationship polyglycol to water, which can be used in the above method for the first and/or third stages of the reaction may range from 90:10 to 10:90, but preferably are in the range of from 30:70 to 70:30.

The temperature at which a phase (s) may be in the range from 50°C to the boiling point of the mixture of polyglycol and Wei the pH value between 7,5 and 12.5, however, it is preferable to carry out at pH ranging from 8.5 to 9.0.

The method is especially suitable for the production of liquid compositions containing the compounds of formula (4)

where M Is Na, R1have the meanings given under formula 1, and R3- phenylamino.

Particularly preferred compounds are those compounds of formula (4), in which R1means phenylamine, -N (C2-C4-hydroxyalkyl)2or amino acid residue, from which derived the hydrogen atom on the amino group. Specific examples of the amino acids, which occur such preferred amino acid residues r1are glycine, alanine, sarcosine, serine, cysteine, phenylalanine, tyrosine (4-hydroxyphenylethyl), diiodotyrosine, tryptophan (-indolylmethane), histidine (-imidazolylalkyl), -aminobutyric acid, methionine, valine (-aminosalicilova acid), Norvaline, leucine (-aminoisoquinoline acid), isoleucine (-amino--methylvaleramide acid), norleucine (-amino-n-hexanoic acid), arginine, ornithine (,-diaminopurine acid), lysine (,-diaminopropane acid), aspartic acid (amino amber acid), glutamic acid (-aminoglutaric acid), threonine, guide oistat such preferred amino acid residues R1especially preferred sarcosine, taurine, Glotova acid and aspartic acid.

At the final stage of the reaction receive the reaction mixture of the compounds of formula (1), and the mixture polyglycol/water. An additional advantage of the present invention is that the mixture containing polyglycol, which has multifunctional properties mentioned above can be used directly, without further processing, for various applications in the field of paper, textiles, detergents and cosmetics.

Preferably the liquid composition contains from 5 to 40% of compounds of formula (1) and from 95 to 60% mixture of polyglycol and water, due to which the ratio of polyglycol to water is between 90:10 and 10:90 parts by mass.

In the dissolved or finely ground state bleach, obtained in the aforementioned manner, show more or less pronounced fluorescence. Therefore, they are used in accordance with the present invention, for optical bleaching of synthetic or natural organic substances.

Examples of such substances, mention of which should not be construed as limiting the scope of the present invention are televital:

(a) polyamides, which are the products of polymerization by ring opening, for example, those that have the type of polycaprolactam,

(b) polyamides, which are the products of polymerization based on bifunctional or polyfunctional compounds able to undergo the condensation reaction, such as hexamethylenediamine were adipat, and

(C) natural organic textile substances of animal or vegetable origin, for example based on cellulose or proteins, such as cotton or wool, linen or silk.

Organic matter, optical bleach, may be at different stages of processing and to provide a preferably finished textile products. They can be, for example, in the form of skeins of textile fibers, yarns, twisted yarns, non-woven products, felt, textile fabrics, textile composites or knitted fabrics.

Bleach defined above, are of particular importance for the treatment of textile fabrics. The treatment of textile materials mainly carried out in aqueous medium, in which a particular optical brighteners are present in finely dispersed form (suspensions, so-called the global agents can choose to enter into the process.

The treatment is usually carried out at temperatures from about 20 to 140°With, for example, at the boiling temperature of the bath, or in this range (about 90°C). For final processing, in accordance with the present invention, of textile substrates is also possible to use solutions or emulsions in organic solvents, as they are used in the practice of dyeing with the so-called solvent dyeing (a method of heat-setting with cushioning pillow and the process of dyeing by exhaustion in the dyeing machine).

Optical brighteners, which can be used in accordance with the present invention, it is also possible to use, for example, in the following forms:

(a) in mixtures with so-called carriers, wetting agents, softeners, swelling agents, antioxidants, light stabilizers, thermal stabilizers and chemical bleaching agents (chlorine bleach and additives in whitening bath);

(b) in mixtures with cross-linking agents and finishing agents (for example starch or synthetic finishing agents), as well as in combination with various processes of textile finishing, especially finishes based on synthetic smo and does not require Ironing”), as well as fire-resistant finishes, finishes that are resistant to the formation of mud or antistatic finishes, as well as protivomikrobnye finishes;

(c) as additives to a variety of Soaps and detergents;

(d) in combination with other substances with optical bleaching effect.

If the bleaching process is combined with textile treatment or finishing methods, the combined treatment can in many cases it is preferable to carry out using the corresponding stable compositions which contain compounds with optical bleaching effect, a concentration at which achieved the desired bleaching action. In some cases, the full effect of the bleach is achieved by subsequent processing. It may be, for example, chemical treatment (e.g., acid treatment), heat treatment (e.g., heat) or combined chemical and thermal processing.

The number of optical brighteners used in accordance with the present invention, relative to the optical bleach material may vary within wide limits. Visible and lasting effect can already be achieved is it possible to use amounts up to 0.5% by weight. For the greatest number of practical applications, the preferred amounts are from 0.05 to 0.5% by weight relative to the bleach material.

Optical brighteners are also particularly suitable as additives to proryvnym baths or to industrial and household detergents, and they can be added in various ways. They are easy to add into the washing bath in the form of their solutions in water or organic solvents or also in fine condition as aqueous dispersions or suspensions. They or their components are conveniently added to household or industrial cleaners on any phase of the process of preparing a detergent, for example, in the so-called “slurry before spray drying of detergent or during cooking combinations of liquid detergents. You can add connections in the form of a solution or dispersion in water or other solvent, or without auxiliary means in the form of a dry bleaching powder. However, they can be sprayed, in dissolved or pre-dispersed form the finished detergent.

Detergents that can be used are the known mixtures of detergent substances, Ltd sulfonic acids of higher fatty alcohols, arylsulfonate, which substituted higher alkyl and/or polyamidine-alkyl, esters of carboxylic acids with alcohols having a molecular weight of from medium to high, acylaminoalkyl or aminoaryl-glycerol-sulfonates of fatty acids, esters of phosphoric acid, fatty alcohols, and so forth. The so-called “components” that can be used are, for example, alkali metal polyphosphates and polymeta-phosphates, alkali metal pyrophosphates of alkali metals, alkali metal salts of karboksimetilcelljulozy and other inhibitors of re-deposition of soil, and also alkali metal silicates, carbonates, alkali metal borates of alkali metals, perborate alkali metals, nitrilotriacetic acid, ethylenediaminetetraacetic acid and foam stabilizers, such as alkanolamine higher fatty acid series. In addition, detergents may contain, for example, antistatic agents, perejivayuschie means to protect the skin, such as lanolin, enzymes, antimicrobial agents, perfumes and dyes.

Bleaches are of particular advantage in that they are also effective in the presence of donors with active chlorine, such as, for example, hypochlorite, and the emer, polyglycolide esters of alkylphenol. And in the presence of perborate or perkiset and activators, such as, for example, tetraaceticacid or ethylenediaminetetraacetic acid, new bleach is very stable in powder detergent and rinsing baths.

Bleach in accordance with the present invention is added in amounts of 0.005 to 2% or more and preferably from 0.03 to 0.5% relative to the weight of liquid or powder ready-to-use detergent. When they are used for washing textiles made from cellulose fibres, polyamide fibres, cellulose fibres with a high degree of finishing, wool and the like, the washing liquid containing the specified number of optical brighteners in accordance with the present invention, give a striking appearance on the daily light.

Processing of the products are performed, for example, as follows.

These textiles are treated for 1-30 minutes at a temperature of from 5 to 100°C and preferably at a temperature of from 25 to 100°C in the wash bath containing from 1 to 10 g/kg of the compound of detergent, which contains the components and from 0.05 to 1% sromisky textiles are rinsed and dried in the traditional way. Rinsing bath may contain as bleaching additives 0.2 g/l of active chlorine (such as hypochlorite), or from 0.1 to 2 g/l of sodium perborate.

Bleach in accordance with the present invention can also be applied from rinsing baths with “media”. For this purpose bleach injected into the tool for gentle rinsing or other rinsing agent, which contains as a “carrier”, for example, polyvinyl alcohol, starch, copolymers of acrylic base or derivatives of formaldehyde/urea or ethylene urea or propylene-urea, in quantities of 0.005 to 5% or more and preferably from 0.2 to 2% relative to the weight obbessive funds. When used in quantities from 1 to 100 ml and preferably from 2 to 25 ml per liter of rinsing bath rinsing means of this type that contain bleach in accordance with the present invention, give the effects a high degree of whiteness is very diverse types of processed textiles.

Another use of the compounds of the present invention consists in bleaching of paper or paper pulp during paper production or in the sizing press, which raskryvaya bleach in accordance with the present invention in such formulations paper, bleached with their help, has a very high degree of whiteness.

In some cases, compounds obtained by the method of the present invention may be useful as an ultraviolet absorbent means and, as such, are suitable for increasing the sun protection factor (SPF) of textile fibrous materials, as described, for example, in the application for the European patent 728749.

The following examples illustrate the invention; parts and percentages are given by weight, unless otherwise indicated.

Example 1

38 g of compound of the formula

suspended in 38 g poliatilenglikola-600 and 30 g of water. Then add a solution 17,16 g disodium salt of aspartic acid in 23 g of water. The reaction mixture was then heated under reflux at a temperature of 95°C, stirring for 6 hours and maintaining the pH at 8.5, and 9.0 by the addition of 11.5 g of 32% sodium hydroxide solution.

The resulting solution contains a compound of the formula

with the release of 96%.

The resulting solution was stable for at least 1 month at a temperature of - 5°C and contains

The compound of the formula (102) 28%

Water 45%

Politicheskogo bleaching of textiles, detergents and paper or to improve sun protection factor of textile fibrous material.

If desired, the product can be obtained in the form of yellowish crystals that do not contain polyethylene glycol, by deposition of warm ethanol.

Similar results can also be obtained by using polyethylene glycol 300 or 1500.

Example 2

1 kg (0.9 mol) wet compounds of the formula (101), containing 280 g of water, suspended in a solution of 159 g (1,71 mol) of aniline and 2.5 kg of polyethylene glycol-300 and stirred under conditions of reflux distilled at a temperature of 130°C for 30 minutes. First, a light solution, after which the precipitated free acid TAS. After cooling, the free acid is filtered off with suction and washed with water.

In another embodiment, the reaction mixture was added 225 g of hot 32% NaOH solution and 275 g of water. After cooling, get 4 kg light of 23.4% solution of the compounds of formula

Example 3

120 g (of 0.65 mol) of acid chloride cyanuric acid are suspended in a mixture of 250 g of polyethylene glycol-300 and 300 g of ice water. Add 1057 (0,314 mol) 12% solution of 4,4'-diaminostilbene-2,2'-dissolvability in the water. pH d is adjusted to 7 with 20% aqueous sodium carbonate solution and add to 61.3 g (0,659 mol) of aniline. The reaction mixture is heated to a temperature of 80°C and pH regulate using 50% NaOH solution. Stirring is continued for 30 minutes at a temperature of 80°C and pH 7. The mixture is heated to a temperature of 96°C and add to 81.6 g (0.82 mol) of diethanolamine at pH of 8.2 to 8.5. Receive a two-phase reaction mixture.

After 30 minutes, add 150 ml of concentrated solution of NaCl. The organic phase is separated and diluted with 200 g of polyethylene glycol-300 and 15 g of water. The pH was adjusted to 10 by addition of 4 g of NaOH (50%) and the mixture filtered.

The reaction mixture contains 24.6% of the compounds of formula

which remains transparent even after months of storage.

Connection, free of solvents, can be isolated by precipitation in ethanol. Yield: 89% 4,4'-diaminostilbene-2,2'-disulfonate.

Example 4

10.4 g of the compound of the formula

suspended in 41 g of polyethylene glycol-200 and 14 g of butyldiglycol. To this mixture was added a solution of 3.1 g (23 mmol) of aspartic acid in 12 ml of water and 2.66 g of 30% NaOH. The reaction mixture is heated to a temperature of 90°C and the pH was adjusted to 8.5-9 using 30% NaOH solution. After 5 hours getting slightly dark is Obedinenie formula

Yield: 95%

Content: 14%

The connection can be distinguished by precipitation in a mixture of acetone and Hcl with subsequent transformation into hexanetriol salt.

Example 5

38 g (66%=30.4 mmol) wet compounds of the formula (101) is added to 40 g of water and 12 g of polyethylene glycol-300. Then add 5,42 g (70 mmol) of methylamine (40% solution in water) and the mixture is heated to a temperature of 90°C. At this temperature, the mixture is stirred for 5 hours and the pH was adjusted to 8.5 by adding NaOH (30%). By the end of the reaction the pH remains constant. The mixture is cooled to room temperature. Get light reactive composition containing 16% of compounds of formula

after you add 38 g of polyethylene glycol-300 in a two-phase reaction mixture.

Identification and content checked by liquid chromatography high resolution (IHVR) and a commercial product (Blankophor HRS).

1. The method of producing a liquid composition containing 4,4'-bis-(creatininemia)-stilbene-2,2'-disulfonato formulas (1)

where R1means phenylamine, -N(C2-C4-hydroxyalkyl)2or the rest of the amino acids from which it is derived at the(C1-C4-alkyl);

M - Na, namely, that the acid chloride cyanuric acid is subjected to interaction with 4,4'-diaminostilbene-2,2'-disulfonate in a mixture of water and polyglycol when the mass ratio of water and polyglycol from 10:90 to 90:10, in the presence of sodium carbonate to obtain the intermediate compounds of formula (2)

which is then subjected to interaction with the compound of the formula R1H, where R1has the above values, equimolecular quantities relative to the acid chloride cyanuric acid to obtain the compounds of formula (3)

with the subsequent interaction of the compound (3) with the compound of the formula R3N, where R3has the above values, and the process is carried out in a medium containing a mixture of water and polyglycol in the specified value.

2. The method according to p. 1, characterized in that the reagents used, essentially, in the stoichiometric proportions required for the formation of compounds of formula (1).

3. The method according to p. 1 or 2, characterized in that polyglycol has a molecular weight in the range of 200-5000.

4. The method according to any of paragraphs.1-3, characterized in that last stage carried the PP.1-4, characterized in that the last stage is carried out at a pH in the range of 7.5 to 12.5.

6. The method according to PP.1-5, characterized in that the liquid composition contains a compound of formula (1), where R3indicates phenylamino, and M and R1have the values listed in paragraph 1.

7. The method according to p. 6, wherein R1indicates the balance of amino acids, which split the hydrogen atom on the amino group.

8. The method according to p. 7, characterized in that the amino acid is aspartic acid.



 

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< / BR>
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25 cl, 2 dwg, 2 tbl, 3 ex

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10 cl, 8 ex, 2 tbl

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25 cl, 1 dwg, 1 tbl, 4 ex

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2 tbl, 12 ex

FIELD: chemistry.

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EFFECT: high substantivity and light resistance of the claimed fluorescent bleaches and their mixes, and better water solubility of the claimed mixes in comparison to the solubility of each individual bleach.

15 cl, 2 tbl, 12 ex

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