CN112535996A - Gemini quaternary ammonium salt-containing surfactant composition - Google Patents

Gemini quaternary ammonium salt-containing surfactant composition Download PDF

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CN112535996A
CN112535996A CN202011554584.9A CN202011554584A CN112535996A CN 112535996 A CN112535996 A CN 112535996A CN 202011554584 A CN202011554584 A CN 202011554584A CN 112535996 A CN112535996 A CN 112535996A
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quaternary ammonium
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ammonium salt
gemini quaternary
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CN112535996B (en
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雷秋芬
吴海龙
高玲玲
李泽勇
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Guangzhou Tinci Materials Technology Co Ltd
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Abstract

The invention belongs to the field of daily chemical materials, and particularly relates to a gemini quaternary ammonium salt-containing surfactant composition, which comprises 0.2-25% of gemini quaternary ammonium salt compound, 2-45% of surfactant and the balance of solvent; wherein the surfactant contains at least one of anionic surfactant and amphoteric surfactant. The composition contains anionic or amphoteric surfactant and gemini quaternary ammonium salt surfactant, and the two surfactants do not generate flocculation precipitation, and have excellent antibacterial property, functional antibacterial property, conditioning property and other comprehensive surface activity properties.

Description

Gemini quaternary ammonium salt-containing surfactant composition
Technical Field
The invention relates to the field of daily chemical materials, in particular to a surfactant composition containing gemini quaternary ammonium salt.
Background
The cation quaternary ammonium salt generally has bactericidal activity and is widely applied to broad-spectrum bactericides.
In the field of daily chemicals, cationic quaternary ammonium salt surfactants cannot be compounded with anionic surfactants, and are easy to flocculate and precipitate once meeting anionic or amphoteric surfactants, but a single cationic quaternary ammonium salt surfactant cannot meet one or more characteristics of higher requirements on conditioning, foaming and decontamination.
In order to solve the problem, a person skilled in the art generally modifies other functional additives by cations so as to unify the antibacterial property of the cations and the surface activity of anions or zwitterions, thereby obtaining a daily chemical product meeting the target requirement.
In the present case, it is desirable to provide a daily use chemical product containing an anionic surfactant, an amphoteric surfactant, and a cationic surfactant.
Disclosure of Invention
The invention aims to provide a surfactant composition containing gemini quaternary ammonium salt, which contains anionic or amphoteric surfactant and gemini quaternary ammonium salt surfactant, does not generate flocculation precipitation, and has excellent antibacterial property, functional antibacterial property, conditioning property and other comprehensive surface activity performances.
Unless otherwise specified, the percentages and parts in the present invention are in weight percent.
In order to achieve the purpose, the invention provides the following technical scheme:
a surfactant composition containing gemini quaternary ammonium salt comprises 0.2-25% of gemini quaternary ammonium salt compound, 2-45% of surfactant, and the balance solvent;
wherein the surfactant at least contains one of anionic surfactant and amphoteric surfactant;
the gemini quaternary ammonium salt has the following structure of formula 1:
Figure BDA0002858235410000021
wherein R is1Is optionally selected from C6-C20Alkyl amidopropyl, C6-C20Alkyl amide ethyl of (1), C6-C20Alkyl acyloxy ethyl radical of (C)6-C20Alkyl acyloxy propyl radical, C6-C20Alkyl acyloxy isopropyl group or H (OCH)2CH2)n-,2≤n≤20;R2、R3Independently selected from hydroxyethyl and C1-C20Alkyl of (C)6-C20Alkyl amidopropyl, C6-C20Alkyl amide ethyl of (1), C6-C20Alkyl acyloxy ethyl radical of (C)6-C20Alkyl acyloxy propyl radical, C6-C20Alkyl acyloxy isopropyl group or H (OCH)2CH2)m-m is more than or equal to 2 and less than or equal to 20, and X is Cl or Br.
In the surfactant composition containing the gemini quaternary ammonium salt, the surfactant further contains one or more of a nonionic surfactant or a cationic surfactant.
The surfactant composition containing the gemini quaternary ammonium salt also comprises a functional auxiliary agent, and the dosage of the functional auxiliary agent is 0.1-10%.
In the surfactant composition containing the gemini quaternary ammonium salt, the functional auxiliary agent is one or more selected from vitamins, chelating agents, perfumes, whitening agents, enzymes, conditioners, thickeners, attractants, dyes, pigments, bleaching agents and pearling agents.
In the surfactant composition containing gemini quaternary ammonium salt, the solvent is one or more selected from water, ethanol, glycerol, propylene glycol, polyethylene glycol and isopropanol.
In the above surfactant composition containing a gemini quaternary ammonium salt, the thickener is selected from the group consisting of: modified hydroxyethyl cellulose, hydrophobically modified polyacrylate, hydrophobically modified polyacrylic acid, hydrophobically modified polyacrylamide, PEG-120 methyl glucose dioleate, PEG-40 sorbitan tetraoleate, PEG-60 sorbitan tetraoleate, PEG-150 pentaerythritol tetrastearate, PEG-55 propylene glycol oleate or PEG-150 distearate.
Compared with the prior art, the invention has the beneficial effects that:
the gemini quaternary ammonium salt adopted by the surfactant composition has an antiseptic effect, no additional existing antiseptic is needed, and the detergent composition has low irritation and high mildness; the gemini quaternary ammonium salt adopted by the surfactant composition can effectively kill malassezia and propionibacterium acnes, and the surfactant composition has the effects of removing dandruff and acne; the gemini quaternary ammonium salt is adopted in the surfactant composition, and the surfactant composition has the functions of conditioning and moisturizing.
The most outstanding advantages of the invention are: the antibacterial and antimicrobial agent can be well compounded with anions or zwitterions, and shows comprehensive antibacterial, conditioning, functional antibacterial and other performances.
Drawings
FIG. 1 is a radar chart of a hair washing test of volunteers.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. 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
In this example, a surfactant composition containing a gemini quaternary ammonium salt was prepared:
(1) formulation components
Figure BDA0002858235410000031
Figure BDA0002858235410000041
(2) Formula process
a. Heating phase A, stirring and dissolving uniformly.
b. After the phase A is dissolved uniformly, the phase B is added and the heating, stirring and dissolving are continuously carried out continuously and uniformly.
c. After the B phase is dissolved uniformly, cooling to normal temperature, adding the C phase, and stirring uniformly.
Example 2
In this example, a surfactant composition containing a gemini quaternary ammonium salt was prepared:
(1) formulation components
Figure BDA0002858235410000042
(2) Formula process
a. Heating phase A, stirring and dissolving uniformly.
b. After the phase A is dissolved uniformly, the phase B is added and the heating, stirring and dissolving are continuously carried out continuously and uniformly.
c. After the B phase is dissolved uniformly, cooling to normal temperature, adding the C phase, and stirring uniformly.
Example 3
In this example, a surfactant composition containing a gemini quaternary ammonium salt was prepared:
(1) formulation components
Figure BDA0002858235410000051
(2) Formula process
a. Heating phase A, stirring and dissolving uniformly.
b. After the phase A is dissolved uniformly, the phase B is added and the heating, stirring and dissolving are continuously carried out continuously and uniformly.
c. After the B phase is dissolved uniformly, cooling to normal temperature, adding the C phase, and stirring uniformly.
Example 4
In this example, a surfactant composition containing a gemini quaternary ammonium salt was prepared:
(1) formulation components
Figure BDA0002858235410000061
(2) Formula process
a. Heating phase A, stirring and dissolving uniformly.
b. After the phase A is dissolved uniformly, the phase B is added and the heating, stirring and dissolving are continuously carried out continuously and uniformly.
c. After the B phase is dissolved uniformly, cooling to normal temperature, adding the C phase, and stirring uniformly.
Example 5
In this example, a surfactant composition containing a gemini quaternary ammonium salt was prepared:
(1) formulation components
Figure BDA0002858235410000062
Figure BDA0002858235410000071
(2) Formula process
a. Heating phase A, stirring and dissolving uniformly.
b. After the phase A is dissolved uniformly, the phase B is added and the heating, stirring and dissolving are continuously carried out continuously and uniformly.
c. After the B phase is dissolved uniformly, cooling to normal temperature, adding the C phase, and stirring uniformly.
Example 6
In this example, a surfactant composition containing a gemini quaternary ammonium salt was prepared:
(1) formulation components
Figure BDA0002858235410000072
Figure BDA0002858235410000081
(2) Formula process
a. Heating phase A, stirring and dissolving uniformly.
b. After the phase A is dissolved uniformly, cooling to normal temperature, adding the phase B, and stirring uniformly.
Example 7
In this example, a surfactant composition containing a gemini quaternary ammonium salt was prepared:
(1) formulation components
Figure BDA0002858235410000082
(2) Formula process
a. Heating phase A, stirring and dissolving uniformly.
b. After the phase A is dissolved uniformly, cooling to normal temperature, adding the phase B, and stirring uniformly.
Example 8
In this example, a surfactant composition containing a gemini quaternary ammonium salt was prepared:
(1) formulation components
Figure BDA0002858235410000091
(2) Formula process
a. Heating phase A, stirring and dissolving uniformly.
b. After the phase A is dissolved uniformly, cooling to normal temperature, adding the phase B, and stirring uniformly.
Example 9
In this example, a surfactant composition containing a gemini quaternary ammonium salt was prepared:
(1) formulation components
Figure BDA0002858235410000101
(2) Formula process
a. Heating phase A, stirring and dissolving uniformly.
b. And after the phase A is dissolved uniformly, adding the phase B, cooling to normal temperature, and stirring uniformly.
Comparative example 1
Comparative example 1 the surfactant composition formulation differs from example 1 in that no gemini quaternary ammonium salt is present.
The results of the comparative example 1 and example 1 volunteer shampooing tests are shown in fig. 1;
the volunteer shampooing test method was as follows:
1, trial description: the half-head test is to wash two shampoos simultaneously in the left and right half-heads during hair washing, and to simultaneously feel different feelings during hair washing and after hair washing by two hands.
2: description of trial experience points: please evaluate the corresponding index in the corresponding labeled time period.
Figure BDA0002858235410000102
3. In combination with the actual use case, you give an objective score evaluation (draw √ at the corresponding position) for the following use effect evaluation index;
Figure BDA0002858235410000111
through the evaluation result of the hair washing test of the volunteers, the radar chart in figure 1 can show that the moisturizing and softening feeling of the example 1 is better than that of the comparative example 1, and the gemini quaternary ammonium salt plays a role in conditioning and moisturizing in the washing composition.
Comparative example 2
Comparative example 2 the surfactant composition formulation differs from example 1 in that karson (15ppm add-on) is used instead of gemini quaternary ammonium salt.
Comparative example 3
Comparative example 3 the surfactant composition formulation differs from that of example 1 in that the same amount of dioctyldimethylhydroxyisopropylammonium chloride is used in place of the gemini quaternary ammonium salt.
Comparative example 4
Comparative example 4 the surfactant composition formulation differs from that of example 1 in that the equivalent amount of quaternary ammonium trimethyl dipropyl ether is used instead of the gemini quaternary ammonium salt.
Comparative example 5
Comparative example 5 the surfactant composition formulation differs from example 1 in that the equivalent amount of lauryl dimethyl hydroxypropyl glyceryl ether ammonium chloride is used instead of the gemini quaternary ammonium salt.
Preservative efficacy test data by USP32 method are as follows:
table 1 comparative surfactant composition corrosion efficacy testing
Figure BDA0002858235410000121
Table 2 comparative surfactant composition corrosion efficacy testing
Figure BDA0002858235410000131
Detergent compositions containing the gemini quaternary ammonium salts can pass the preservative efficacy test, such as the preservative efficacy test of examples 1 and 2; the anticorrosion effect is basically equal to that of the cason, see the anticorrosion efficacy test of comparative example 2; the cleaning composition without the gemini quaternary ammonium salt failed the preservative efficacy test, see comparative example 1. Detergent compositions containing equal amounts of dioctyldimethylhydroxyisopropyl ammonium chloride, quaternary ammonium trimethyldipropyl ether, lauryl dimethylhydroxypropyl glyceryl ether ammonium chloride failed the preservative efficacy test, see comparative examples 3, 4 and 5 for preservative efficacy test. The gemini quaternary ammonium salts act as preservatives in detergent compositions.
Comparative example 6
Comparative example 6 the surfactant composition formulation differs from example 1 in that piroctone olamine salt (0.9% addition) is used instead of gemini quaternary ammonium salt.
The sterilization and bacteriostasis performance test data of malassezia furfur by the QB/T2738-2012(7.3) method are as follows:
TABLE 3 Malassezia furfur Sterilization, bacteriostasis test comparison
Figure BDA0002858235410000132
The washing composition containing the gemini quaternary ammonium salt can pass the sterilization performance test of malassezia furfur, such as the sterilization and bacteriostasis performance test of malassezia furfur in examples 1 and 5; the sterilization effect is more than 99 percent and is basically equal to the piroctone olamine, and the sterilization and bacteriostasis performance test of malassezia furfur is shown in a comparative example 6; the washing composition without the gemini quaternary ammonium salt can not pass the sterilization and bacteriostasis performance tests of malassezia furfur, see the sterilization and bacteriostasis performance tests of malassezia furfur in the comparative example 1. The detergent composition containing the same amount of dioctyldimethylhydroxyisopropyl ammonium chloride, quaternary ammonium trimethyldipropyl ether, lauryl dimethylhydroxypropyl glyceryl ether ammonium chloride can not pass the sterilization and bacteriostasis tests of malassezia furfur, as shown in the test examples 3, 4 and 5. The gemini quaternary ammonium salt has the function of sterilizing malassezia furfur in the washing composition.
The data of the sterilizing and bacteriostatic performance test of the propionibacterium acnes by the QB/T2738-2012(7.3) method are as follows:
TABLE 4 comparison of the bactericidal and bacteriostatic properties of Propionibacterium acnes
Figure BDA0002858235410000141
The washing composition containing the gemini quaternary ammonium salt can pass the test of the sterilizing performance of the propionibacterium acnes, and the sterilizing effect is more than 99, such as the test of the sterilizing and bacteriostasis performance of the propionibacterium acnes in example 1 and example 3. The washing composition without the gemini quaternary ammonium salt can not pass the propionibacterium acnes sterilization and bacteriostasis tests, see comparative example 1 propionibacterium acnes sterilization and bacteriostasis tests. Detergent compositions containing equal amounts of dioctyldimethylhydroxyisopropyl ammonium chloride, quaternary ammonium trimethyldipropyl ether, lauryl dimethylhydroxypropyl glyceryl ether ammonium chloride failed the propionibacterium acnes bactericidal, bacteriostatic performance tests, see comparative examples 3, 4 and 5, propionibacterium acnes bactericidal, bacteriostatic performance tests. The gemini quaternary ammonium salt has the function of sterilizing propionibacterium acnes in a washing composition.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.

Claims (6)

1. A surfactant composition containing gemini quaternary ammonium salt is characterized by comprising 0.2-25% of gemini quaternary ammonium salt compound, 2-45% of surfactant and the balance of solvent;
wherein the surfactant at least contains one of anionic surfactant and amphoteric surfactant;
the gemini quaternary ammonium salt has the following structure of formula 1:
Figure FDA0002858235400000011
wherein R is1Is optionally selected from C6-C20Alkyl amidopropyl, C6-C20Alkyl amide ethyl of (1), C6-C20Alkyl acyloxy ethyl radical of (C)6-C20Alkyl acyloxy propyl radical, C6-C20Alkyl acyloxy isopropyl group or H (OCH)2CH2)n-,2≤n≤20;R2、R3Independently selected from hydroxyethyl and C1-C20Alkyl of (C)6-C20Alkyl amidopropyl, C6-C20Alkyl amide ethyl of (1), C6-C20Alkyl acyloxy ethyl radical of (C)6-C20Alkyl acyloxy propyl radical, C6-C20Alkyl acyloxy isopropyl group or H (OCH)2CH2)m-m is more than or equal to 2 and less than or equal to 20, and X is Cl or Br.
2. The surfactant composition containing gemini quaternary ammonium salts according to claim 1, wherein the surfactant further comprises one or more of a nonionic surfactant or a cationic surfactant.
3. The surfactant composition containing gemini quaternary ammonium salt according to claim 1, further comprising a functional auxiliary agent, wherein the amount of the functional auxiliary agent is 0.1-10%.
4. The gemini quaternary ammonium salt-containing surfactant composition as claimed in claim 3, wherein the functional adjuvant is one or more selected from vitamins, chelating agents, perfumes, brighteners, enzymes, conditioners, thickeners, attractants, dyes, pigments, bleaches and pearling agents.
5. The surfactant composition containing gemini quaternary ammonium salts according to claim 1, wherein the solvent is one or more selected from water, ethanol, glycerol, propylene glycol, polyethylene glycol and isopropanol.
6. The gemini quaternary ammonium salt-containing surfactant composition according to claim 4, wherein the thickener is selected from the group consisting of: modified hydroxyethyl cellulose, hydrophobically modified polyacrylate, hydrophobically modified polyacrylic acid, hydrophobically modified polyacrylamide, PEG-120 methyl glucose dioleate, PEG-40 sorbitan tetraoleate, PEG-60 sorbitan tetraoleate, PEG-150 pentaerythritol tetrastearate, PEG-55 propylene glycol oleate or PEG-150 distearate.
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CN115785937A (en) * 2022-10-28 2023-03-14 四川科宏达集团有限责任公司 Acid-resistant waterproof locking agent for low-permeability gas well and preparation method thereof
WO2024087584A1 (en) * 2022-10-24 2024-05-02 中国日用化学研究院有限公司 Diester-based gemini quaternary ammonium salt as well as preparation method therefor and use thereof

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WO2024087584A1 (en) * 2022-10-24 2024-05-02 中国日用化学研究院有限公司 Diester-based gemini quaternary ammonium salt as well as preparation method therefor and use thereof
CN115785937A (en) * 2022-10-28 2023-03-14 四川科宏达集团有限责任公司 Acid-resistant waterproof locking agent for low-permeability gas well and preparation method thereof

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