Method for preparing polymeric product used for leather treatment

FIELD: chemistry of polymers, leather industry, chemical technology.

SUBSTANCE: invention relates to a method for preparing polymeric products that are used in processes for dressing leather or fur, in treatment and disinfection of natural and sewage waters. Method for preparing polymeric products involves the hydroxymethylation reaction of polyhexamethylene guanidine chloride with formaldehyde and arylation reaction of prepared product with aromatic compound comprising o-amino- or o-hydroxy-groups. The hydroxymethylation reaction is carried out in the presence of acetic acid or formic acid up to formation of trimethylol derivative of polyhexamethylene guanidine chloride. In some cases the arylation product is subjected for complex formation with transient metal salt or azo-coupling reaction with diazonium salt taken among group including sulfanilic acid, naphthionic acid, j-naphthyls, p-nitroaniline, 2,6-dichloro-4-nitroaniline. Invention provides simplifying, accelerating and enhancing the effectiveness of process in dressing leathers with derivatives of polyhexamethylene guanidine showing tanning effect, staining properties, flocculating capacity and high antibacterial activity.

EFFECT: improved preparing method.

3 cl, 1 tbl, 9 ex

 

The invention relates to the field of biologically active polymer compounds synthesized by chemical means, in particular copolymers of salts alkilammoniya, and can be used in the processes of leather and fur, as well as for cleaning and disinfection of natural waters and sewage.

Known application of chloride, guanidine (phmg) formula

as a flocculant for cleaning chrome-containing waste water (Patent RU 2033394, 20.04.95). Lack of flocculant flocculation is low capacity and antimicrobial activity, lack tanning and coloring properties. Known copolymer salts alkilammoniya formula

where x is Cl-or HE-as biocidal flocculant (inventor's certificate SU 1728256 A1, 23.04.92). However, the known copolymer does not show tanning and coloring properties.

A method of obtaining polymer products for leather processing, including processing of chloride, guanidine formaldehyde in 0.01 N. the borax solution and then added to the reaction mixture of aromatic amines (Patent RU 2151192, 20.06.2000 year). The disadvantages of the polymer products obtained in a known manner, are low tanning ability and antimicrobial activity.

The closest in technical eskay essence and the achieved result is (prototype) a method of obtaining a polymer product for processing hides hydroxymethylpropane derivative of guanidine formaldehyde in 0.01 N. the borax solution, followed by AllYouNeed derived hydroxymethylpropane aromatic compounds with donor substituents and the azo coupling derived arilirovaniya and diazonium salts selected from the group comprising sulfanilic acid, α-naphtylamine, n-nitroaniline or nationowl acid, which then received uzasadnienie subjected to complexation with the participation of cations of transition metals, where the ligands are athropy and ortho-hydroxy-a-amino group derived result (Patent RU 2191787, 27.10.2002,).

A disadvantage of the known method of producing polymer products is the long duration (6 hours) hydroxymethylpropane chloride, guanidine formaldehyde and complex reaction result, components of the dye that requires careful observance of the mode of synthesis. The polymer products obtained in a known manner are insufficient tanning ability and low antimicrobial activity.

The technical result achieved by the invention, is to simplify, accelerate and improve the efficiency of the process of tanning leather derivatives of guanidine, manifesting tanning action, coloring properties, flocculation capacity and high antimicrobial activity.

The essence of izobreteny what is the method of deriving pgmg by chemicals to skin treatment, meet the structural formula

where X=HE, or Ar, or ArN=HAr' or the ArMy, My - Sol transition metal, n is the number of links, chloride pgmg, m is the number of links trimethylamine derivative, k is the number of links of eritreaethiopia of blockcopolymer. A distinctive feature of the method of deriving pgmg, including such well-known methods of synthesis, as hydroxymethylpropane chloride, guanidine formaldehyde, atilirovanie product hydroxymethylpropane aromatic compound containing o-amino - or o-hydroxy-group, is that hydroxymethylpropane formaldehyde is carried out in the presence of acetic or formic acid to education trimethylamino derived chloride, guanidine, (trimethylsily block copolymers) proposed as a bactericidal tanning agent and flocculant, structural formula (X=OH)

product arilirovaniya subjected to complexation with transition metal salt or the azo coupling with salt, page, selected from the group comprising sulfanilic acid, nationowl acid, j - naphtylamine, n - nitroaniline, 2,6-dichloro-4-nitroaniline.

The interaction of chloride, guanidine with formaldehyde has the character of nucleophilic attachment. It is proishodit both acidic (the proposed method), and alkaline environment (patent RU 2151192 C1, published 20.06.2000, and patent RU 2191787 C2, published 20.05.2002,). Since guanidine nucleus in the molecule of the chloride pgmg contains three secondary amino group, it can react up to three molecules of CH2O forming units derived chloride pgmg with different content of methyl groups from mono - to trimethylamine depending on the number entered in the reaction of the NH groups. Known methods for producing polymer products based on the processing of chloride, guanidine formaldehyde in an alkaline medium 0.01 n solution of borax. Under these conditions, the reaction accession carbonyl carbon of formaldehyde occurs after getprotobyname secondary amino groups occurring as a result of their direct interaction with the molecule of formaldehyde. Seamless integration between molecules of formaldehyde and secondary amine groups on the basis of patterns of chloride pgmg, is only possible with two secondary amino groups bound to carbon single bond. Reactivity of the secondary amino groups bound to carbon double bond, shielded by the proton adduct of guanidine (odnogolosnogo base and HCl, which is in a slightly alkaline environment, created 0.01 N. a solution of borax, localized at the nitrogen of the above amino group. Therefore, in the known method recip is of polymeric products, the formation of dimethylamino derived chloride pgmg, which mass may contain up to 26% of the methylol groups. As for trimethylamino derived chloride pgmg, its formation in these conditions.

Synthesis in acidic environment enhances ELECTROPILOT carbon atom of formaldehyde due to the protonation of the oxygen atom and the alignment of the electronic configuration of the adduct of guanidine HCl and that leads to the formation of carbocation-From+H2HE on the one hand and the hydrogen bonds between the acid and the base, on the other, which is limited without the transfer of a proton to a base, protolytic reaction in an acidic environment. Under the influence of the induction effect inherent in electrophilic reactions, formaldehyde carbocation in the acidic environment actively joins nitrogen all three secondary amino guanidine nucleus of a molecule of chloride pgmg with education level trimethylamino derived chloride pgmg structural formula

The number of methylol groups contained in the link trimethylamino derived chloride phmg is 34.8% of its mass. For varying the ratio of links chloride pgmg with his trimethylamine derivative and accordingly the content of methylol groups in trimethylamino blockcopolymer need to change the ratio from the reaction source is x substances and the synthesis.

A greater number of methyl groups attached during hydroxymethylpropane chloride, guanidine in an acidic medium gives trimethylurea blockcopolymer reinforced tanning properties compared with the known analogue synthesized in alkaline environment. Electrophilic carbon atom in the methyl groups of blockcopolymer-CH2HE, along with tanning activity, enhances flocculation effect of blakesophiey when cleaning gelatin, black and oily wastewater. Through the synergistic guanidino and methyl groups, the obtained block copolymers characterized by the increased bactericidal activity against common pathogenic microorganisms Staph. Aureus, Proteus vulgaris, Pseudomonas aeruginosa, E.Coli and fungicide against fungi and yeast-like fungi of the genera Aspergillus, Penicillum and Candida.

Arthritically block copolymers, offered as bactericidal tanning agent, dye and flocculant responsible structural formula

get AllYouNeed trimethylamino of alexopoulou. Atilirovanie are aromatic compounds with donor substituents (phenol, αand β- Naftali, resorcinol, aniline, α-naphtylamine and others).

Metal complex aryltrimethylammonium block copolymers, proposed to the operation of bactericidal tanning agent and dye, responsible, for example, structural formula

get added to the solution alltimelow of blockcopolymer salt of the transition metal My. Aryltrimethylammonium block copolymers takes complexation c chloride of a transition metal cation of which has the empty electronic levels. In contrast to the known metal complex derivative (patent RU 2191787 C2, published 20.05.2002 g) in metal-complex alltimeitem blockcopolymer as ligands are ortho-amino - or ortho-oxypropyl aromatic nuclei and the nitrogen atom of the secondary amino guanidine nucleus chloride, guanidine.

Isoprostane alltimelow of blockcopolymer offered as bactericidal tanning agent and a dye corresponding to the formula

produced by azo coupling alltimelow of blockcopolymer with diazonium compounds. Diazonium salts creep beforehand on the basis of sulfanilic acid, nationway acid, α-naphtylamine, n-nitroaniline, 2,6-dichloro-4-nitroaniline.

The gradual modification of chloride pgmg accompanied by a change in the physical properties of the polymer. The accession of three methyl groups in the process of getting trimethylamino derived causes an increase in molecular weight is definitely using viscometry) chloride pgmg on 28÷ 33%. The solubility of the polymer after hydroxymethylpropane does not change. The main technical result achieved trimethylamine blockcopolymers increase the temperature of the welding of the hide in the tanning offered by the product.

Aryltrimethylammonium the copolymers are resins of different degrees of viscosity, odorless, in most cases, slightly coloured. Introduction to macromolecules trimethylamino of blockcopolymer aromatic nuclei reduces the solubility of the derivative in water, but when heated they all, except for the effect - free remedy and nationalpost, soluble in water. Saved solubility in alcohols, appears affinity for benzene, toluene (they swell here).

The main technical result achieved aryltrimethylammonium blockcopolymers simultaneous increase in the thickness and temperature of the welding prefabricated, processed, we offer the product in the process of dublirovaniya - filling protein structures. The simultaneous improvement in the functions of the filler and the tanning agent associated with the presence in the composition of the polymer product anytimetraining (r) and trimethylamine links(m).

Azo dyes based on alltimelow of blockcopolymer - powdery substance poorly soluble in water, sparingly soluble in alcohols, well - sulfoxide.

R is stoimosti and colors of azo dyes change the combination of different combinations of derivatives alltimelow of blockcopolymer and salts of the page. The main technical result achieved isoprostane alltimelow of blockcopolymer - increase thickness and temperature welding in the process of staining prefabricated "fiber", for which the semi-finished product is dipped in the solution alltimelow of blockcopolymer, then produce salt processing the page. The offered product has a high molecular weight compared with the received product in a known manner.

Aryltrimethylammonium block copolymers in the complexation with transition metal salt acquires magnetic properties that acknowledges receipt of the metal complex dye. The presence of the magnetic properties of product sets the classical definition, the average magnetic susceptibility method Faraday resonance EPR methods. The main technical result achieved metal complex aryltrimethylammonium blockcopolymers - increase thickness and temperature welding in the coloring process of the semi-finished product "on the fiber while maintaining a high resistance to light, dry and wet friction painted designs, simplifying the process of obtaining a metal complex dye. The effect of filling the accompanying dyeing semi-finished products, suggests the combination of these processes.

Example 1. Take all the needs of icesto granules chloride, guanidine and 38%formalin solution. Granules chloride, guanidine (phmg) are ground into powder. Synthesis of methyl blockcopolymer carried out in round-bottom reaction flask, located on the heater with thermostat. The flask is equipped with a stirrer and reflux condenser. In the reaction flask contribute 17.8 g of powder chloride pgmg. Then in the flask add 29.2 ml of formalin solution, and then 2.6 ml of glacial acetic acid. The synthesis is carried out at constant stirring. The temperature of the reaction mixture is maintained at 80°C. the Process is conducted until reaching the equilibrium state, while the number of methylol groups in the reaction product ceases to change within 30 minutes of the Equilibrium state reached after 2 hours the Number of methylol groups in the reaction product is 33% of the sample mass. It suits the content in trimethylamino blockcopolymer: 5 mol.% links chloride pgmg (units n) and 95 mol. % links trimethylamino derived chloride pgmg (units m). It is used for the tanning of fur semi-finished product and waste water from the protein. The temperature of the welding leather and fabric skins after tanning specified blockcopolymers 85°C, the porosity of 56%. The degree of purification of waste water from the protein (the concentration of 480 mg/l) when used as a flocculant with a dose of 2 mg/l in the presence of a coagulant (200 mg/l su is that aluminum) reaches 81%, Minimum bacteriostatic concentration (Mbsc) trimethylamino of blockcopolymer, inhibiting the growth of fungi Aspergillus niger and Candida geotrichim is 11.0 and 5.7 g/ml, respectively. For comparison, Mbsc chloride pgmg, inhibiting the growth of fungi Aspergillus niger and Candida geotrichim is 14.7 and 9.8 g/ml, respectively.

Example 2. Trimethylamine block copolymers receive according to example 1. In a reaction flask set the temperature to 60°and make it a 18 g α-naphtylamine. The reaction is carried out for 2 hours. Get aryltrimethylammonium block copolymers in the form of α-naphthylamine derived trimethylamino of blockcopolymer. In the above structural formula alltimelow of blockcopolymer Ar represents an aromatic hydrocarbon residue α-naphtylamine. Obtained a resinous product is a pale pink color is washed with ethyl acetate and used for filling and retanning of collagen. The growth temperature of the joining material after processing received α-naphthylamine derived trimethylamino of blockcopolymer is 11°C, the porosity of 46.1%. Porosity reduction compared with its value in example 1 indicates that the received α-naphthylamine derived trimethylamino of blockcopolymer in addition to the properties of tanning agent has a filling effect. Growth is olseni semi amounts to 26.7%. The degree of purification of waste water from the protein (the concentration of 480 mg/l) when used as a flocculant with a dose of 2 mg/l in the presence of a coagulant (200 mg/l of aluminum sulfate) is 93%.

Example 3. Trimethylamine block copolymers receive according to example 1. In a reaction flask set the temperature to 60°and make it a 18 g β-naphthol. The reaction is carried out for 2 hours. Get aryltrimethylammonium block copolymers with the above structural formula where Ar represents an aromatic hydrocarbon residue β-naphthol. Obtained a resinous product is milky white washed with ethyl acetate and used for filling and retanning of collagen. The growth temperature welding leather fabric sheepskin, after processing the received β-naftolin derived trimethylamino of blockcopolymer is 9°C, the porosity of 48.6%. Porosity reduction compared with its value in example 1 indicates that the received β-naphtalene derived trimethylamino of blockcopolymer in addition to the properties of tanning agent has a filling effect. Increase the thickness of the semi-finished product amounts to 25.0%.

Example 4. Get α-naphthylamine derived trimethylamino of blockcopolymer according to example 2. To the resulting resinous product is a pale pink color add 6.7 the CoCl 2×6N2Oh and at a temperature of 60°stirred for 1 hour. Cooled, filtered off, washed with alcohol and dried. Get metal complex aryltrimethylammonium of blockcopolymer with the above structural formula where Ar represents an aromatic hydrocarbon residue α-naphtylamine, a My=CuCl2. The synthesized metal complex painted in green colour. Samples of semi-finished painted obtained dye in green colour. The light fastness of the fiber, painted "fiber" - 7 points.

Example 5. Get β-naphtalene derived trimethylamino of blockcopolymer according to example 3. To the resulting resinous product milky color add 4.8 g of CuCl4×2H2O and at a temperature of 60°stirred for 1 hour. Cooled, filtered off, washed with alcohol and dried. Thus obtained metal complex aryltrimethylammonium block copolymers with the above structural formula where Ar represents an aromatic hydrocarbon residue β-naphthol, a My=CuCl2. The synthesized metal complex painted in dark brown color. Samples of semi-finished painted obtained dye in dark brown color. The light fastness of the fiber, painted "fiber" - 7 points.

Example 6. Get β-naphtalene derived trimethylamine is luxapalila according to example 3. To the resulting resinous product milky color added 6.9 g CuCO4×5H2Oh and at a temperature of 60°stirred for 1 hour. Cooled, filtered off, washed with alcohol and dried. Thus obtained metal complex aryltrimethylammonium block copolymers with the above structural formula where Ar represents an aromatic hydrocarbon residue β-naphthol, a My=CuSO4. The synthesized metal complex painted in dark brown color. Samples of semi-finished painted obtained by the dye in the mustard color. The light fastness of the fiber, painted "fiber" - 7 points.

Example 7. Get β-naphtalene derived trimethylamino of blockcopolymer according to example 3. To the resulting resinous product milky color added 5.1 g of Cu (CH3COO)2and at a temperature of 60°stirred for 1 hour. Cooled, filtered off, washed with alcohol and dried. Thus obtained metal complex aryltrimethylammonium block copolymers with the above structural formula where Ar represents an aromatic hydrocarbon residue β-naphthol, and Mu=Cu (CH3Soo)2. The synthesized metal complex painted in dark brown color. Samples of semi-finished painted obtained by the dye in the color of swamp green (khaki). The lightfastness is Alekna, painted "fiber" - 7 points.

Example 8. Get α-naphthylamine derived trimethylamino of blockcopolymer according to example 2. Then 4.67 g α-naphthylamine derived trimethylamino of blockcopolymer dissolved in 17 ml of 1 N. hydrochloric acid. Separately prepare salt diatope. To do this, dissolve 1.7 g selfapproval acid in 4.2 ml of 2 n sodium hydroxide. In the last solution is added a solution of 0.7 g of sodium nitrite in 8.5 ml of water. The reaction mixture is cooled to 0-5°and with stirring, bring prepared in hydrochloric acid solution α-naphthylamine derived trimethylamino of blockcopolymer. The newly obtained mixture is added 2 n sodium hydroxide solution until alkaline reaction. The mixture is kept for 2 hours, after which the precipitate is filtered off. So get isoprostane alltimelow of blockcopolymer with the above structural formula where Ar represents an aromatic hydrocarbon residue α-naphtylamine, and Ar' is an acid residue of resolveconflict. The obtained coloring isoprostane dyes leather in orange color.

Example 9. Get β-naphtalene derived trimethylamino of blockcopolymer according to example 3. Prepare a solution of 4.16 g β-naftalina derived trimethylamino of blockcopolymer in 22.5 ml of 2 n sodium hydroxide solution. The CTD is Ino preparing a salt of the page. To do this, dissolve 2.5 g of sulfanilic acid in 6.5 ml of 2 n sodium hydroxide. To the mixture was added a solution of 1 g of sodium nitrite in 12 ml of water. The reaction mixture is cooled to 10°and while mixing, gradually introduce it to the glass with 13 ml of 2 n hydrochloric acid. Loose white powdery residue diazonium salts in the form of mist poured with stirring to the alkaline solution β-naftalina derived trimethylamino of blockcopolymer. The mixture is stirred for 30 minutes, add 12.5 g of sodium chloride and stand in the cold for 1 hour. The precipitation is filtered off and dried. So get isoprostane alltimelow of blockcopolymer with the above structural formula where Ar represents an aromatic hydrocarbon residue β-patola, and Ar' is an acid residue of resolveconflict. The obtained coloring isoprostane stains the skin yellow.

Data characterizing derivatives chloride pgmg received proposed and known (prototype) the methods given in the table.

Table.

Characteristics derived chloride pgmg and methods for their preparation.
The polymer product and method thereofOfferKnown
Product hydroxymethylpropane chloride pgmg:Trimethylamine derivedDimethylamino derived
- the content of methylol groups in the product, % by weight3323
time hydroxymethylpropane, hours26
- temperature welding of the hide after tanning product, °C8577
Product arilirovaniya methylol derivative chloride pgmg:Alltimechisinau derivedAlltimechisinau derived
the growth temperature welding of semi-finished processed product, °7-84-6
- increase the thickness of the semi-finished processed product, %.25.0-26.721.0-23.0
Pigment product of associate derived chloride pgmgSaaristomeren derivedSoaringeaglecasino derived
Coloring product complexation derived chloride pgmgMetal-complex alltimecase derivedMetal complex soaringeaglecasino derived
The sequence of operations of obtaining the production of the s chloride pgmg Chloride pgmg + formaldehyde → trimethylamine derived + aromatic compound → alltimechisinau derived + complexation or azo coupling → metal complex alltimechisinau or saaristomeren coloring derivedChloride pgmg + formaldehyde → dimethylamine derived + aromatic compound → alltimechisinau derived + azocoupling → soaringeaglecasino derived + complexation → metal complex soaringeaglecasino prohodna

These tables show that trimethylamine derived chloride pgmg contains 10% more methylol groups compared with the polymer product obtained in a known manner, which ensures the increase of temperature welding of the hide after tanning offered by the product.

Moreover, to obtain polymer tanning product manufacturing leather on the proposed method takes 3 times less time than known. In addition, from the data presented in the table shows that the processing of semi-finished product, we offer a polymeric product in the process of filling the retanning provides compared to the prototype simultaneous increase of temperature joining and thickness.

As for dyeing processes, then the effect is one the belt increase the temperature of the weld and the thickness of the semi-finished product is reproduced in the coloring process of the semi-finished product "fiber", since its beginning, before processing the salt of the page or transition metal impregnated aryltrimethylammonium blockcopolymers causing this effect.

With regard to the distinctive features of the proposed method in comparison with the known, from the table clearly shows that in addition to time there is a significant difference between the sequence of operations of synthesis and participating derivatives chloride pgmg.

1. The method of obtaining polymer products for skin treatment, including hydroxymethylpropane derivative of guanidine formaldehyde and atilirovanie product hydroxymethylpropane aromatic compound containing o-amino-or o-hydroxy-group, characterized in that as a derivative of guanidine use chloride, guanidine, and hydroxymethylpropane are in the presence of acetic or formic acid to education trimethylamino derived chloride, guanidine.

2. The method according to claim 1, characterized in that the product of arilirovaniya subjected to complexation with transition metal salt.

3. The method according to claim 1, characterized in that the product of arilirovaniya are azo coupling with salt, page, selected from the group comprising sulfanilic acid, nationowl acid, j-naphtylamine, n-nitrone is in, 2,6-dichloro-4-nitroaniline.



 

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22 cl, 1 tbl, 2 sch, 78 ex

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