CN114213647A - Zwitterionic surfactant, preparation method and application thereof - Google Patents

Zwitterionic surfactant, preparation method and application thereof Download PDF

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Publication number
CN114213647A
CN114213647A CN202111448415.1A CN202111448415A CN114213647A CN 114213647 A CN114213647 A CN 114213647A CN 202111448415 A CN202111448415 A CN 202111448415A CN 114213647 A CN114213647 A CN 114213647A
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dyeing
acid
leveling agent
zwitterionic surfactant
dye
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杨海涛
李成达
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Xiamen Dabang Ruida Printing And Dyeing Material Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C08G65/3348—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing nitrogen in addition to sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/326—Polymers modified by chemical after-treatment with inorganic compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/39—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes
    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
    • C08G2650/04—End-capping

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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Inorganic Chemistry (AREA)
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Abstract

The invention discloses a zwitterionic surfactant, a preparation method and application thereof. Taking fatty amine polyoxyethylene ether as a raw material, and carrying out sulfonation reaction and alkylation reaction to obtain a zwitterionic surfactant; adding a proper amount of water for dilution to obtain the zwitterionic leveling agent for the acid dye. The zwitterionic surfactant provided by the invention can simultaneously have excellent affinity for acid dyes and nitrogen-containing fibers such as chinlon, wool and the like, has better dye retarding and dye transfer performances in the dyeing process, overcomes the defect that a single cationic or anionic leveling agent is easy to have dyeing defects such as dyeing defects of dyeing defects such as dyeing defects, color spots and the like in acid dye dyeing, and is an acid dye leveling agent with excellent performance.

Description

Zwitterionic surfactant, preparation method and application thereof
Technical Field
The invention relates to a zwitterionic surfactant, a preparation method thereof and a zwitterionic leveling agent applied to acid dye dyeing, and belongs to the technical field of textile printing and dyeing auxiliaries.
Background
In the dyeing process of wool and nylon fabrics, most of the dyeing is carried out by using acid dyes, the acid dyes contain anionic groups such as sulfonic groups and carboxyl groups, the wool and nylon fabrics are in cationic charge in an acid bath, and the anionic groups on the acid dyes and the cationic groups on the fabrics have strong affinity, so that the acid dyes are quickly dyed to cause competitive dyeing and instantaneous dyeing, and the phenomenon of uneven dyeing is easy to occur, such as: dyeing defects such as color stripes, color spots and the like occur, so that the quality of the fabric is greatly influenced. In order to promote uniform dyeing, avoid defects such as color spots, color spots and the like and effectively improve the dyeing uniformity, a leveling agent is required to be used in the dyeing.
Leveling agents for acid dyes currently used in the market are mainly anionic and cationic leveling agents. Cationic leveling agents are dye-philic leveling agents which form compounds of varying degrees of stability primarily with anionic groups on the dye, however, blocking of water-soluble groups on the dye due to anionic-cationic bond bonding can cause precipitation of mono-sulfonic acid group dyes, even multi-sulfonic acid group dyes, if added in excess, can cause aggregation and precipitation of the dye. Therefore, accurate metering is important when using a cationic leveling agent, however, accurate metering is difficult to achieve in an actual production process due to factors such as production personnel and metering instruments. As such, purely cationic levelling agents have been less useful in dyeing. The anionic leveling agent is a hydrophilic leveling agent, wool and nylon fibers have certain positive charge in an acid bath, and the molecules of the anionic leveling agent are smaller than the molecular structure of an acid dye, so that the anionic leveling agent is firstly adsorbed on the fibers and occupies a cationic dye base of the fibers. The acid dye adsorbs fibers slowly, but the dye has higher affinity to the fibers, and the dye gradually replaces a levelling agent to dye the fibers along with the increase of the temperature of a dye bath. Therefore, the anionic leveling agent is helpful for dye leveling property. However, if the molecular weight of the anionic leveling agent is too large and the molecular structure has a plurality of sulfonic acid groups, the binding force of the anionic leveling agent to the fiber is too large, the dye base on the fiber is closed to prevent the dye from being dyed, and more seriously, the color point and the color spot phenomenon of the dyeing are increased by the leveling agent, so that not every anionic compound is suitable as the acidic leveling agent, and the molecular weight is particularly required to be selected. The molecular structure of the zwitterionic leveling agent has cationic and anionic groups simultaneously, and the cationic and anionic groups have affinity to fibers and dyes, so that the zwitterionic leveling agent has the performance advantages of both anionic and cationic leveling agents, and has better slow dyeing and leveling performances in dyeing.
At present, there are a large number of documents reporting the development of acidic levelling agents, and most of the documents relate to cationic or anionic levelling agents, while few reports on zwitterionic levelling agents have been made and no practical application has been found. Therefore, it is necessary to develop a zwitterionic leveling agent.
Disclosure of Invention
The invention aims to overcome the defects of the existing acid leveling agent technology, and provides a zwitterionic surfactant which has good adsorption capacity with dye and fiber and thus has good dyeing retarding and leveling effects on acid dye in the dyeing process, a preparation method and a zwitterionic leveling agent applied to acid dye dyeing.
The technical scheme for realizing the aim of the invention is to provide a preparation method of a zwitterionic surfactant, which comprises the following steps:
(1) adding an aliphatic amine polyoxyethylene ether raw material into a reactor, stirring and heating to 50-150 ℃, adding a proper amount of a sulfonation reagent and a catalyst, wherein the sulfonation reagent is one of sulfur trioxide, fuming sulfuric acid, sulfamic acid and chlorosulfonic acid, and carrying out heat preservation sulfonation reaction for 1-10 hours;
(2) adding a proper amount of water and sodium haloacetate at the temperature of 50-100 ℃, and carrying out heat preservation alkylation reaction for 1-10 hours, wherein the alkylation reagent is one of sodium chloroacetate and sodium bromoacetate, so as to obtain the yellow and viscous zwitterionic surfactant.
The technical scheme of the invention comprises the zwitterionic surfactant obtained by the preparation method, and the structural formula of the zwitterionic surfactant is as follows:
Figure 309979DEST_PATH_IMAGE002
，
in the formula, a is an integer of 12-18; b. c is an integer, and b + c is more than or equal to 5 and less than or equal to 60; x-Is Cl-Ions or Br-Ions; m is sodium ion Na+Or ammonium ion NH4 +。
The technical scheme of the invention also comprises the application of the zwitterionic surfactant, and the zwitterionic surfactant is applied to a zwitterionic leveling agent of the acid dye.
Compared with the prior art, the invention has the beneficial effects that:
1. the molecular structure of the zwitterionic surfactant provided by the invention has cationic and anionic groups simultaneously, and the zwitterionic surfactant has excellent affinity to nitrogen-containing fibers such as wool and chinlon and acid dyes.
2. The zwitterionic surfactant provided by the invention is applied to a leveling agent of an acid dye, and the obtained zwitterionic leveling agent has the performance advantages of both an anionic leveling agent and a cationic leveling agent, has better dye retarding and dye transfer performances in a dyeing process, and overcomes the defect that dyeing defects such as dyeing defects, color spots and the like are easy to appear in a single cationic or anionic leveling agent in dyeing.
Detailed Description
The technical solution of the present invention is further described with reference to the following specific examples.
Example 1:
adding 310g of a metered fatty amine polyoxyethylene ether (octadecylamine is added into 15mol of ethylene oxide) raw material into a reaction bottle, stirring and heating to 50-150 ℃, adding 32g of sulfamic acid and a proper amount of a catalyst, carrying out heat preservation reaction for 1-10 hours, sampling and measuring the sulfonation degree, and determining the reaction end point when the sulfonation degree reaches 14-16. Cooling to below 100 ℃, adding 396g of water and 54g of sodium bromoacetate, carrying out heat preservation reaction at 50-100 ℃ for 1-10 hours, sampling and measuring isoelectric points, and obtaining the yellow and viscous zwitter-ion surfactant with the content of 50% and the appearance after the product is qualified, wherein the structural formula is as follows:
Figure 858772DEST_PATH_IMAGE004
，
wherein: a is 18; b. c is an integer, b + c = 15; x-Is Br-Ions; m is ammonium ion NH4 +。
The obtained amphoteric surfactant can be directly used as a leveling agent for acid dyes after being diluted by a proper amount of water.
Example 2:
adding 310g of metered fatty amine polyoxyethylene ether (octadecylamine is added into 15mol of ethylene oxide) into a reaction bottle, stirring and heating to 50-150 ℃, adding 37g of 98% concentrated sulfuric acid in batches, reacting for 1-10 hours under heat preservation, vacuumizing and dehydrating in the heat preservation reaction process, finally sampling and measuring the sulfonation degree, and determining the reaction end point when the sulfonation degree reaches 14-16. Cooling to below 60 ℃, adding 75g of 40% liquid alkali to neutralize the reaction system, wherein the pH is = 7-9, adding 366g of water and 42g of sodium chloroacetate, reacting at 50-100 ℃ for 1-10 hours, sampling and measuring the isoelectric point, and obtaining the yellow and viscous zwitterionic surfactant with the content of 50% and the appearance after the product is qualified, wherein the structural formula is as follows:
Figure DEST_PATH_IMAGE006
，
wherein: a is 18; b. c is an integer, b + c = 15; x-Is Cl-Ions; m is sodium ion Na+。
The amphoteric surfactant provided by the embodiment can be directly used as an acidic leveling agent. The zwitterionic leveling agent synthesized in the embodiment for dyeing acid dyes has the following technical indexes:
1. appearance: a light brown viscous liquid;
pH (1% aqueous solution): 7.5-9.5;
3. solubility: is easily soluble in water;
4. ionic type: amphiprotic;
5. stability: the product does not delaminate and deteriorate in 6 months;
6. solid content: 50 percent.
Example 3
In this example, different leveling agents were used to test the simultaneous dyeing properties of acid dyes for comparison in dyeing applications.
Dyeing materials: nylon knitted fabric, acid dye (Shanghai vitamin), glacial acetic acid
The dyeing process comprises the following steps: bath ratio of 1: 2098 ℃ for 45min
Acetic acid 1g/l
Acid leveling agent 1g/l
The dye formula comprises: bright green acid bright yellow N-3GL 1%
Acid turquoise blue N-3G 1%
The test method comprises the following steps: refer to the national standards HG/T4262-2011, HG/T4263-2011 and HG/T4436-2012.
The application of the zwitterionic leveling agent synthesized in examples 1 and 2 of the present invention was compared with a commercially available cationic leveling agent (octadecylamine polyether 1815) and an anionic leveling agent (sodium dodecyl diphenyl ether disulfonate 2A 1), and the results are shown in Table 1.
TABLE 1
Figure DEST_PATH_IMAGE008
。
From the test results it can be seen that: the anionic leveling agent 2A1 has a dye-blocking effect on acid dye bright yellow N-3GL, and the dyed cloth surface is blue; the cationic leveling agent 1815 and the leveling agents provided in examples 1 and 2 of the present invention have excellent leveling effects on both the acid brilliant yellow N-3GL and the acid emerald blue N-3G dyes. At the dyeing end point, the anionic leveling agent 2A1 has a dye-blocking effect on acid dye light yellow N-3GL all the time, and the dyed cloth surface is blue light.
The cationic leveling agent 1815 and the leveling agent synthesized in the embodiment 1 of the invention have little influence on the final color light of two dyes of acid bright yellow N-3GL and acid emerald blue N-3G, and have good leveling effect, but the cationic leveling agent 1815 has cationic characteristic in an acid dyeing solution, and must be accurately metered in the charging process
In conclusion, the zwitterionic leveling agent provided by the invention has better dyeing synchronism to acid dyes during initial dyeing and final dyeing, can ensure that dyeing diseases such as color spots and flowers are not easy to occur in the dyeing process, and is a leveling agent for acid dyes with excellent performance.

Claims (3)

1. A preparation method of a zwitterionic surfactant is characterized by comprising the following steps:
(1) adding an aliphatic amine polyoxyethylene ether raw material into a reactor, stirring and heating to 50-150 ℃, adding a proper amount of a sulfonation reagent and a catalyst, wherein the sulfonation reagent is one of sulfur trioxide, fuming sulfuric acid, sulfamic acid and chlorosulfonic acid, and carrying out heat preservation sulfonation reaction for 1-10 hours;
(2) adding a proper amount of water and sodium haloacetate at the temperature of 50-100 ℃, and carrying out heat preservation alkylation reaction for 1-10 hours, wherein the alkylation reagent is one of sodium chloroacetate and sodium bromoacetate, so as to obtain the yellow and viscous zwitterionic surfactant.
2. A zwitterionic surfactant obtainable by the process of claim 1 and having the formula:
Figure 992153DEST_PATH_IMAGE002
，
in the formula, a is an integer of 12-18; b. c is an integer, and b + c is more than or equal to 5 and less than or equal to 60; x-Is Cl-Ions or Br-Ions; m is sodium ion Na+Or ammonium ion NH4 +。
3. The use of a zwitterionic surfactant according to claim 2 in a zwitterionic levelling agent for acid dyes.
CN202111448415.1A 2021-11-30 2021-11-30 Zwitterionic surfactant, preparation method and application thereof Withdrawn CN114213647A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101225060A (en) * 2007-12-21 2008-07-23 王伟松 Method for synthesizing fatty amine polyoxyethylene ether ammonium sulfate
CN112941938A (en) * 2020-07-20 2021-06-11 广东创新精细化工实业有限公司 Chinlon dyeing anti-color-spot-fixing agent and application method thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101225060A (en) * 2007-12-21 2008-07-23 王伟松 Method for synthesizing fatty amine polyoxyethylene ether ammonium sulfate
CN112941938A (en) * 2020-07-20 2021-06-11 广东创新精细化工实业有限公司 Chinlon dyeing anti-color-spot-fixing agent and application method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
王克亮: ""毛用匀染剂的合成与应用"", 《工程科技I辑》, vol. 1, no. 07, pages 024 - 114 *

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