CN113666979B - Cyanuric chloride derivative and preparation method and application thereof - Google Patents
Cyanuric chloride derivative and preparation method and application thereof Download PDFInfo
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- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C3/00—Tanning; Compositions for tanning
- C14C3/02—Chemical tanning
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- C14C3/26—Chemical tanning by organic agents using other organic substances, containing halogen
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Abstract
The invention relates to the technical field of leather auxiliaries, and provides a cyanuric chloride derivative. The cyanuric chloride derivative provided by the invention is white in color, so that the cyanuric chloride derivative can be used as a tanning agent for tanning light-colored or even white leather. Meanwhile, two active chlorines contained in the chemical structure of the tanning agent provided by the invention can generate double-point cross-linking reaction with amino on the skin collagen, and the cyanuric chloride derivative is used as a bridge to cross-link the amino on the skin collagen together to obtain a cross-linked product, so that the heat resistance of the leather is improved, and the shrinkage temperature of the leather is further improved. Experimental results show that the shrinkage temperature of the tanned wet white leather can reach 73-80 ℃ by using the cyanuric chloride derivative provided by the invention as a leather tanning agent, and the leather surface is white, flat and fine.
Description
Technical Field
The invention belongs to the technical field of leather additives, and particularly relates to a cyanuric chloride derivative, and a preparation method and application thereof.
Background
The leather tanning agent is a key tanning auxiliary agent developed for changing raw leather into leather, and plays an important role in leather chemical auxiliaries. The chrome-based tanning has excellent performance, the chrome tanning method always occupies the dominant position in light leather production in the tanning process, but the chrome-based tanning method is gradually replaced by a chrome-free tanning agent due to the problem of serious chromium pollution, and the currently commonly used chrome-free tanning agent mainly comprises a vegetable tanning agent and an organic phosphine tanning agent.
The vegetable tanning leather obtained by using the vegetable tanning agent has the advantages of compact tissue, firmness, fullness, good extensibility and formability and unique tannin extract skin, however, the vegetable tanning agent has certain color and is not suitable for tanning light-color leather. Although, organophosphine tanning agents can tan light colored leather, even pure white leather. However, the shrinkage temperature of the leather tanned by the organic phosphine tanning agent is usually lower than 60 ℃, and the requirement of the leather on higher shrinkage temperature cannot be met.
Therefore, there is a need to develop a chrome-free leather tanning agent capable of tanning light-colored leather, and leather tanned by the tanning agent has higher shrinkage temperature.
Disclosure of Invention
In view of this, the object of the present invention is to provide a tanning agent which is capable of tanning light-colored leather and which has a higher shrinkage temperature. The leather tanning agent provided by the invention does not contain chromium, and the shrinkage temperature of leather tanned by the tanning agent reaches 74-80 ℃.
In order to achieve the above purpose, the invention provides the following technical scheme:
the invention provides a cyanuric chloride derivative, which has a chemical structure shown as a formula I:
the invention provides a preparation method of cyanuric chloride derivatives in the scheme, which comprises the following steps:
cyanuric chloride, water, an emulsifier, a glucosamine compound and alkali are mixed for substitution reaction to obtain cyanuric chloride derivatives; the temperature of the substitution reaction is 0-5 ℃.
Preferably, the glucosamine-based compound comprises glucosamine hydrochloride and/or glucosamine sulfate.
Preferably, the pH of the reaction system of the substitution reaction is 6.0-7.0.
Preferably, the emulsifier comprises fatty alcohol-polyoxyethylene ether AEO-7 and/or fatty alcohol-polyoxyethylene ether AEO-9.
Preferably, the base comprises sodium hydroxide and/or sodium carbonate.
Preferably, the ratio of the amounts of the cyanuric chloride to the glucosamine compounds is (2-3): 1.
preferably, the weight ratio of the emulsifier to the cyanuric chloride is (0.4-1.2): (16-23).
Preferably, the weight ratio of the water to the cyanuric chloride is (50-80): (16-23).
The invention also provides application of the cyanuric chloride derivative in the scheme in leather tanning, and the cyanuric chloride derivative is used as a leather tanning agent.
The invention provides a cyanuric chloride derivative which has a chemical structure shown in a formula I, wherein the chemical structure comprises two cyanuric chloride and one glucosamine structural unit. The cyanuric chloride derivative provided by the invention is white in color, and can be used as a tanning agent, so that the color of light-colored leather is not polluted due to the color of the tanning agent, and the cyanuric chloride derivative can be used as a tanning agent for tanning light-colored or white leather. Meanwhile, each cyanuric chloride structural unit in two cyanuric chloride structural units contained in the chemical structure of the tanning agent provided by the invention contains one active chlorine, so that two active chlorines contained in one cyanuric chloride derivative molecule can generate double-point cross-linking reaction with amino groups on skin collagen, and the cyanuric chloride derivative is used as a bridge to cross-link the amino groups on the skin collagen together to obtain a cross-linked product, thereby improving the heat resistance of leather, further improving the shrinkage temperature of the leather, and ensuring that the tanned leather has good tanning property. Experimental results show that the shrinkage temperature of the tanned wet white leather can reach 73-80 ℃ by using the cyanuric chloride derivative provided by the invention as a leather tanning agent, and the leather surface is white, flat and fine.
Drawings
FIG. 1 is a hydrogen spectrum of a cyanuric chloride derivative prepared in example 1 of the present invention;
FIG. 2 is a graph showing a hydrogen spectrum comparison between a cyanuric chloride derivative prepared in example 1 of the present invention and glucosamine hydrochloride.
FIG. 3 is a comparison graph of the infrared spectra of cyanuric chloride derivative prepared in example 1 of the present invention and cyanuric chloride.
Detailed Description
The invention provides a cyanuric chloride derivative, which has a chemical structure shown as a formula I:
the cyanuric chloride derivative provided by the invention is white in color, so that the cyanuric chloride derivative can be used as a tanning agent for tanning light-colored or even white leather. Meanwhile, two active chlorines contained in the chemical structure of the tanning agent provided by the invention can generate double-point cross-linking reaction with amino on the skin collagen, and the cyanuric chloride derivative is used as a bridge to cross-link the amino on the skin collagen together to obtain a cross-linked product, so that the heat resistance of the leather is improved, and the shrinkage temperature of the leather is further improved.
The invention provides a preparation method of cyanuric chloride derivatives in the technical scheme, which comprises the following steps: cyanuric chloride, water, an emulsifier, a glucosamine compound and alkali are mixed for substitution reaction to obtain cyanuric chloride derivatives; the temperature of the substitution reaction is 0-5 ℃.
The source of the cyanuric chloride is not specially specified in the invention, and the conventional commercial product is adopted.
In the present invention, the water is preferably deionized water. The invention selects deionized water as the solvent for reaction, which can avoid the adverse effect of impurities in water on the reaction and further improve the yield of the product.
In the present invention, the glucosamine-based compound preferably includes glucosamine hydrochloride and/or glucosamine sulfate. In the invention, the glucosamine hydrochloride and the glucosamine sulfate are compounds processed from biomass raw materials, the glucosamine hydrochloride and/or the glucosamine sulfate prepared by hydrolyzing natural resource chitin are/is used as reaction raw materials, and the raw materials are biodegradable and have wide sources.
In the present invention, the emulsifier preferably comprises fatty alcohol-polyoxyethylene ether AEO-7 and/or fatty alcohol-polyoxyethylene ether AEO-9. In the invention, the fatty alcohol-polyoxyethylene ether AEO-7 and/or the fatty alcohol-polyoxyethylene ether AEO-9 can form stable emulsion by using a mixed solution of components which are not mutually soluble, and the emulsifier is common in practice and is relatively cheap.
In the present invention, the alkali preferably includes sodium hydroxide and/or sodium carbonate. The invention selects the sodium hydroxide and/or sodium carbonate with relatively low price as the alkali needed by the substitution reaction, the alkali added in the reaction system is used as an acid-binding agent, and the acid generated in the reaction process is neutralized.
In the present invention, the ratio of the amounts of the cyanuric chloride to the glucosamine-based compound is preferably (2 to 3): 1, more preferably (2.1 to 2.8): 1.. According to the invention, the dosage of the cyanuric chloride and the glucosamine compound is controlled within the range, so that on one hand, the reaction can be fully carried out, and on the other hand, the waste of raw materials can be avoided.
In the invention, the weight ratio of the water to the cyanuric chloride is preferably (50-80): (16-23), more preferably (60-70): (16-23). In the present invention, the amount of water is controlled within the above range, and the concentration of the raw material can be controlled within a suitable range to promote the sufficient progress of the substitution reaction.
In the invention, the weight ratio of the emulsifier to the cyanuric chloride is preferably (0.4-1.2): (16-23), more preferably (0.5-1.0): (16-23). The invention controls the dosage of the emulsifier in the range, and can form stable emulsion among materials, thereby promoting the full progress of reaction.
According to the invention, water, cyanuric chloride and an emulsifier are preferably mixed, and then a glucosamine compound and alkali are sequentially added to carry out substitution reaction, so as to obtain the cyanuric chloride derivative. According to the invention, the glucosamine compound is added into cyanuric chloride, which is beneficial to the reaction of active chlorine in the cyanuric chloride, and the yield of a target product is improved; the alkali added in the reaction system is used as an acid-binding agent to neutralize acid generated in the reaction process, so that the forward progress of the reaction is promoted, and the yield of the product is improved.
In the present invention, the base is preferably added in the form of an alkali solution. The concentration of the alkali solution is not particularly specified in the present invention, and the concentration of the alkali solution required for adjusting the pH of the reaction system, which is well known to those skilled in the art, may be used. The invention utilizes the alkali solution to maintain the reaction system in a proper range, thereby promoting the forward reaction and improving the product yield.
In the present invention, the mixing is preferably performed at a temperature of 0 to 5 ℃. According to the invention, water, cyanuric chloride and an emulsifier are mixed at 0-5 ℃, so that the temperature in a mixing system is kept at 0-5 ℃ when the glucosamine compound is added, and thus, one active chlorine in the cyanuric chloride can react with the glucosamine compound, and the increase of byproducts caused by the reaction of other chlorine atoms in the cyanuric chloride is avoided.
The temperature of the substitution reaction is controlled to be 0-5 ℃, so that the reaction of active chlorine in cyanuric chloride and glucosamine compounds is facilitated, and the yield of a target product is improved. The cyanuric chloride derivative is obtained by reacting with amino and primary hydroxyl in a glucosamine molecular structure at 0-5 ℃ based on a mechanism that the reaction activity of three chlorine groups in the cyanuric chloride molecular structure is controlled by temperature (see the reaction research of cyanuric chloride and aliphatic polyamine and the preparation of dendritic multi-arm initiation core, precious in Yangtze university, Master thesis, 2009).
In the invention, the pH of the reaction system of the substitution reaction is preferably 6.0-7.0. The invention controls the pH value of the reaction system of the substitution reaction in the range, which is beneficial to fully neutralizing acid generated in the substitution reaction process, thereby promoting the forward reaction and improving the product yield.
In the invention, the time of the substitution reaction is preferably 3-7 h, and more preferably 4-6 h. The invention controls the time of the substitution reaction within the range, is beneficial to the full progress of the substitution reaction and improves the yield of the target product.
After the substitution reaction is completed, the present invention preferably purifies the product of the substitution reaction to obtain the cyanuric chloride derivative.
The purification mode of the purification is not specially specified in the invention, and the high-purity product can be obtained by adopting a purification mode which is well known to a person skilled in the art.
The invention also provides the application of the cyanuric chloride derivative in the technical scheme in leather tanning, and the cyanuric chloride derivative is used as a leather tanning agent.
The application of the cyanuric chloride derivative as the leather tanning agent is not specially specified, and the cyanuric chloride derivative is used for performing conventional tanning on delimed and softened grey leather under the condition of no pickling. When the tanning agent provided by the invention is used for tanning delimed and softened grey leather, the pH value at the initial stage of tanning is 7.5-8.0, and the pH value can be kept at 5.5-6.5 after the tanning is finished, so that the tanning process does not need pickling process operation, and the salt pollution caused by a pickling process is eliminated.
The source of the grey skin is not specified in the invention, and the products which are obtained by unhairing and liming the animal skin and are in an expansion state are adopted, which are well known to the technical personnel in the field.
The method for deliming and softening is not specially specified in the invention, and the ash skin is treated by adopting a deliming and softening method well known in the art.
In the present invention, the weight ratio of the cyanuric chloride derivative to the ashen skin which has not been delimed and softened is preferably 2% to 3%. The invention controls the dosage of the cyanuric chloride derivative in the range, and the tanning effect of the leather is better.
In the present invention, the product of the substitution reaction can be used as a tanning agent without purification. In the present invention, the products of the substitution reaction are mainly water and cyanuric chloride derivatives, a small amount of by-products of the substitution reaction, a small amount of emulsifiers and a small amount of remaining unreacted raw materials; in the application example of the present invention, the product after the substitution reaction is not purified, and the reaction system after the substitution reaction is directly used as a tanning agent.
By using the cyanuric chloride derivative provided by the invention as a leather tanning agent, the shrinkage temperature of tanned wet-white leather can reach 73-80 ℃, and the leather surface is white and flat.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Example 1
A cyanuric chloride derivative has a chemical structural formula:
the cyanuric chloride derivative tanning agent comprises the following synthesis steps:
(1) adding 72g of deionized water and 16.7g of cyanuric chloride into a four-neck flask, adding 90.6g of emulsifier AEO, keeping the temperature at 2 ℃, and uniformly stirring;
(2) keeping the temperature unchanged, adding 9.5g of glucosamine hydrochloride into the system, slowly dropwise adding 18.5g of sodium hydroxide solution with the mass concentration of 20%, adjusting the pH value of the system to stabilize the pH value at 6.0, continuously reacting for 4.5h to obtain the milky white tanning agent dispersion containing the cyanuric chloride derivative (the mass content of the cyanuric chloride derivative in the dispersion is about 15.4%), and purifying the dispersion to obtain the cyanuric chloride derivative.
The nuclear magnetic characterization hydrogen spectrum of the cyanuric chloride derivative with the structure in example 1 is shown in the attached figure 1, and the specific analysis result is as follows:
1H NMR(500MHz,CDCl3)：δ(ppm)7.25(s,1H)，3.90(m,2H)，3.40(t,1H)，3.46(m,1H)，3.60(m,1H)，3,75(m,1H)，3.90(d,1H)，4.08(d,1H)，4.20(d,1H)，4.70(s,1H)。
comparison of hydrogen spectra for nuclear magnetic characterization of cyanuric chloride derivatives of example 1 and glucosamine hydrochloride, see figure 2, the results of the analysis are as follows:
delta 2.87 is-NH in glucosamine hydrochloride2(ii) a Delta 7.25 is-NH-generated by the target product.
The infrared spectra of cyanuric chloride derivatives of example 1 and cyanuric chloride are compared, see figure 3, and the results are as follows:
3200cm-1is an N-H stretching vibration absorption peak; 1292. 1049 and 852cm-1The characteristic absorption peak of the triazine ring skeleton (comparing that of cyanuric chloride, the triazine ring is 1496, 1268 and 883cm-1The peak value of the target product is red-shifted); 1245cm-1Stretching vibration of the ether bond.
The results of the elemental analysis of the cyanuric chloride derivative of the structure of example 1 are as follows:
| element name | Theoretical value/%) | Test value/%) |
| C | 30.31 | 30.46 |
| H | 2.32 | 2.97 |
| O | 16.84 | 17.36 |
| Cl | 29.90 | 28.37 |
| N | 20.63 | 20.84 |
In conclusion, it can be seen from the characterization results of the nuclear magnetic, infrared and elemental analyses that the cyanuric chloride derivative having the structure shown in example 1 was successfully prepared.
Example 2
The chemical structural formula of the cyanuric chloride derivative is the same as that of example 1, and the preparation process mainly differs from that of the cyanuric chloride derivative in that: the glucosamine hydrochloride is changed into glucosamine sulfate.
The cyanuric chloride derivative tanning agent comprises the following synthesis steps:
(I) adding 68.5g of deionized water and 22g of cyanuric chloride into a four-neck flask, adding 71.0g of emulsifier AEO, keeping the temperature at 4 ℃, and uniformly stirring;
(II) keeping the temperature unchanged, adding 13g of glucosamine sulfate into the system, slowly dropwise adding 60g of sodium carbonate solution with the mass concentration of 12% to adjust the pH value of the system, stabilizing the pH value at 6.8, continuously reacting for 5.5h to obtain milky white tanning agent dispersion containing the cyanuric chloride derivative, (the mass content of the cyanuric chloride derivative in the dispersion is about 15.2%), and purifying the dispersion to obtain the cyanuric chloride derivative.
Example 3
The chemical structural formula of the cyanuric chloride derivative is the same as that of example 1, and the preparation process mainly differs from that of the cyanuric chloride derivative in that: the material amount, the reaction temperature and the reaction time are changed.
The cyanuric chloride derivative tanning agent comprises the following synthesis steps:
(I-1) adding 65g of deionized water and 20g of cyanuric chloride into a four-neck flask, adding 90.8g of emulsifier AEO, keeping the temperature at 5 ℃, and uniformly stirring;
(I-2) keeping the temperature unchanged, adding 11g of glucosamine hydrochloride into the system, dropwise adding 28g of sodium hydroxide solution with the mass concentration of 15% to adjust the pH value of the system to stabilize the pH value at 6.8, continuously reacting for 6h to obtain the milky white tanning agent dispersion containing the cyanuric chloride derivative (the mass content of the cyanuric chloride derivative in the dispersion is about 17.7%), and purifying the dispersion to obtain the cyanuric chloride derivative.
Example 4
The chemical structural formula of the cyanuric chloride derivative is the same as that of example 1, and the preparation process mainly differs from that of the cyanuric chloride derivative in that: the amounts of material and reaction temperature and reaction time were varied compared to example 2.
The cyanuric chloride derivative tanning agent comprises the following synthesis steps:
(01) adding 62g of deionized water and 18g of cyanuric chloride into a four-neck flask, adding 70.8g of emulsifying dispersant AEO, keeping the temperature at 5 ℃, and uniformly stirring;
(02) keeping the temperature unchanged, adding glucosamine sulfate 10 into the system, slowly dropwise adding 65g of sodium carbonate solution with the mass concentration of 10% to adjust the pH value of the system, stabilizing the pH value at 7.0, continuously reacting for 5h to obtain the cyanuric chloride derivative tanning agent dispersoid with milky appearance (the mass content of the cyanuric chloride derivative in the dispersoid is about 12.8%), and purifying the dispersoid to obtain the cyanuric chloride derivative.
Application example 1
The cyanuric chloride derivative tanning agent dispersoid mainly comprises water and cyanuric chloride derivatives, and water, a small amount of byproducts generated by substitution reaction and a small amount of residual unreacted raw materials have no influence on later-stage use, so in actual use, the cyanuric chloride derivative tanning agent dispersoid obtained in the examples 1-4 is directly used as a tanning agent.
Respectively weighing 4 pieces of liming sheep skin, carrying out conventional deliming, softening, degreasing, washing and other treatments according to a clothing leather process, respectively loading the leather into 4 comparative experimental drums, and carrying out tanning treatment according to the following processes: respectively adding 100% of water, respectively adding 15% of cyanuric chloride derivative tanning agent dispersion prepared in examples 1-4 into 4 comparative experiment rotary drums (100% and 15% are weight percentage relative to the soaked sheep skin), and rotating for 120 minutes at 25-30 ℃; adjusting the pH value of the bath lotion to 6.0-6.5 by using a sodium bicarbonate solution, then heating to 40 ℃, rotating the drum for 120 minutes, continuing to perform drum treatment for 100 minutes at 50 ℃, adjusting the pH value of the bath lotion to 6.0-6.5 by using the sodium bicarbonate solution, rotating the bath lotion for 20 minutes, and stopping the drum for overnight; continuing to rotate for 30 minutes the next day, taking out the skin, standing, sampling and checking the shrinkage temperature (Ts) of the skin blank. The test standard is as per QB/2713-2005, and the experimental results are as follows:
as can be seen from application example 1: the shrinkage temperature of the leather blank of the sheep tanned by the product obtained in the examples 1-4 reaches 74-80 ℃, the white wet leather surface is white and flat, and the waste liquid after tanning is clear and well absorbed; the tanning agent provided by the invention is used for tanning leather, and a pickling process is not needed before tanning, so that acid pollution caused by the pickling process is eliminated.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A cyanuric chloride derivative having a chemical structure according to formula I:
2. a process for the preparation of cyanuric chloride derivatives as claimed in claim 1, which comprises:
cyanuric chloride, water, an emulsifier, a glucosamine compound and alkali are mixed for substitution reaction to obtain cyanuric chloride derivatives; the temperature of the substitution reaction is 0-5 ℃.
3. The method according to claim 2, wherein the glucosamine-based compound comprises glucosamine hydrochloride and/or glucosamine sulfate.
4. The method according to claim 2, wherein the pH of the reaction system of the substitution reaction is 6.0 to 7.0.
5. The method of claim 2, wherein the emulsifier comprises fatty alcohol-polyoxyethylene ether AEO-7 and/or fatty alcohol-polyoxyethylene ether AEO-9.
6. The method of claim 2, wherein the base comprises sodium hydroxide and/or sodium carbonate.
7. The method according to claim 2, wherein the ratio of the amounts of the cyanuric chloride to the glucosamine-based compound is (2 to 3): 1.
8. the preparation method according to claim 2, wherein the weight ratio of the emulsifier to the cyanuric chloride is (0.4-1.2): (16-23).
9. The preparation method according to claim 2, wherein the weight ratio of the water to the cyanuric chloride is (50-80): (16-23).
10. Use of cyanuric chloride derivatives as claimed in claim 1 as leather tanning agents, characterized in that the cyanuric chloride derivatives are used as leather tanning agents.
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Address after: 512400 Pearl Industrial Park, Nanxiong, Shaoguan, Guangdong Patentee after: Guang Dong Dongdun New Material Technology Co., Ltd. Address before: 512499 Zhuji Industrial Park, Nanxiong City, Shaoguan City, Guangdong Province Patentee before: NANXIONG SEATON CHEMICALS LTD. |