High-foam glycosyl amide organosilicone cationic surfactant as well as preparation method and application thereof

Abstract

The invention belongs to the technical field of organic compounds, and particularly relates to a high-foam glycosyl amide organosilicon cationic surfactant as well as a preparation method and application thereof. The preparation method of the surfactant comprises the following steps: taking a renewable resource D-gluconic acid delta-lactone as a raw material, carrying out amidation reaction on the raw material and N, N-dimethyl dipropylene triamine to obtain a glucosamide precursor, reacting the precursor with bromododecane, introducing a hydrophobic chain to obtain an intermediate; and finally, carrying out quaternization reaction on the obtained intermediate and 3-chloropropyl methyl dimethoxy silane / 3-chloropropyl trimethoxy silane, so as to synthesize two kinds of glucosamide organosilicon quaternary ammonium salts. No three wastes are discharged in the synthesis process, and the method is suitable for industrial production; the synthesized surfactant has good foamability, foam stability, biocompatibility, no toxicity, no irritation and bactericidal performance, and can play an important role in the fields of medical treatment, self-cleaning, electronics, energy, agriculture, daily chemical industry and the like in the future.

Description

Technical Field

[0001] This invention belongs to the field of organic compound technology, specifically relating to a high-foaming glycosylamide organosilicon cationic surfactant, its preparation method, and its application. Background Technology

[0002] In recent years, with consumers' increasing demands for personal care products, the market demand for surfactants with multiple functional properties has been growing. Especially in the personal care sector, consumers expect products to have excellent foaming and antibacterial properties, be gentle and non-irritating, and meet environmental protection requirements. This complex demand presents new challenges for surfactant research and development. However, currently available cationic surfactants are mostly low-foaming. Therefore, developing green, high-foaming cationic surfactants has become an important research direction in this field. This trend is driven by multiple factors, including profound changes in market demand, the inherent requirements of technological innovation, and the inevitable trend of the entire industry towards green and sustainable development.

[0003] Glycosyl cationic surfactants, as a novel type of surfactant, utilize sustainably renewable glycosyl groups to modify organosilicon bis-quaternary ammonium salts. This not only retains the broad-spectrum bactericidal properties of organosilicon bis-quaternary ammonium salts but also significantly reduces irritation, improves biocompatibility and renewability through the introduction of glycosyl groups, making them safer and more environmentally friendly. The introduction of the glycosyl structure also significantly enhances the product's resistance to hard water, thanks to the abundant hydroxyl functional groups and Ca2+. 2+ Mg 2+ It forms stable complexes with metal ions. Currently, there are no mature products with similar structures on the market. This product fills the technological gap of "bactericidal + high foaming + green" cationic surfactants and can be widely used in antibacterial detergents, medical disinfectants, high-end cosmetics and other fields. Summary of the Invention

[0004] In response to the current market demand for green, high-foaming glycosyl amide organosilicon cationic surfactants, this invention provides a novel surfactant that combines the non-toxic, non-irritating, and hard water-resistant properties of glycosyl amides with the broad-spectrum bactericidal properties of organosilicon gemini quaternary ammonium salts, along with its preparation method and applications.

[0005] To achieve the above objectives, the technical solution of the present invention is as follows: In a first aspect, the present invention provides a high-foaming glycosylamide organosilicon cationic surfactant having the following structural formula: or .

[0006] In a second aspect, the present invention provides a method for preparing the high-foaming glycosylamide organosilicon cationic surfactant described in the first aspect, comprising the following steps: Step 1: Dissolve D-gluconate-δ-lactone and N,N-dimethyldipropyltriamine in anhydrous ethanol and react them with an amine ester to obtain the precursor N,N-dimethyldipropene-N(3-glycosylamide). Step 2: Dissolve the precursor N,N-dimethyldipropene-N(3-glycosylamide) and bromododecane in anhydrous ethanol, and obtain a double-long-chain glycosyl quaternary ammonium salt containing amide bonds through a substitution reaction, which is the intermediate; Step 3: Dissolve the intermediate with 3-chloropropylmethyldimethoxysilane or 3-chloropropyltrimethoxysilane in anhydrous ethanol, and then perform a quaternization reaction to obtain a double long carbon chain organosilicon quaternary ammonium salt containing glycosyl amide bonds, which is the surfactant.

[0007] In some embodiments of the present invention, the molar ratio of D-glucono-δ-lactone to N,N-dimethyldipropylenetriamine in step 1 is 1.01:1.0.

[0008] In some embodiments of the present invention, the temperature of the amine ester reaction in step 1 is 85°C and the time is 1-2 h.

[0009] In some embodiments of the present invention, the molar ratio of the precursor N,N-dimethyldipropene-N(3-glycosylamide) to bromododecane in step 2 is 1.0:2.01.

[0010] In some embodiments of the present invention, the temperature of the substitution reaction in step 2 is 85°C and the time is 5-6 h.

[0011] In some embodiments of the present invention, the molar ratio of the intermediate to 3-chloropropylmethyldimethoxysilane or 3-chloropropyltrimethoxysilane in step 3 is 1.0:1.01.

[0012] In some embodiments of the present invention, the temperature of the quaternization reaction in step 3 is 85°C and the time is 32~36h.

[0013] Thirdly, the present invention provides the application of the high-foaming glycosylamide organosilicon cationic surfactant described in the first aspect in antibacterial detergents, medical disinfectants, and high-end cosmetics.

[0014] Compared with the prior art, the beneficial effects of the present invention are as follows: (1) The glycosyl surfactants used in this invention have significant advantages in terms of sustainable development: they are made from renewable biomass resources, are biodegradable, and do not produce toxic residues. Compared with traditional petroleum-based surfactants, the production process of glycosyl surfactants has lower carbon emissions.

[0015] (2) The surfactant of the present invention belongs to the high foaming type of glycosyl amide organosilicon cationic surfactant, which improves the foaming performance of traditional cationic surfactants. The introduction of glycosyl groups significantly improves the foaming performance of organosilicon bis-quaternary ammonium salt, especially showing an outstanding enhancement effect in terms of foam stability.

[0016] (3) The surfactant of the present invention improves the problem of poor hard water resistance of traditional cationic surfactants. Even in solutions prepared from standard hard water, it has good foam stability and can still guarantee foam performance when applied to tap water.

[0017] (4) The surfactant of the present invention has good bactericidal properties (see the minimum inhibitory concentration analysis and test report of surfactant provided by Guangdong Provincial Microbiology Analysis and Testing Center). This efficient and broad-spectrum bactericidal property has broad application prospects in medical device disinfection.

[0018] (5) The surfactant of the present invention has good biocompatibility and is non-toxic and non-irritating under the premise of excellent performance (see the surfactant toxicity / irritation analysis and test report provided by Guangdong Provincial Microbiology Analysis and Testing Center), making it safer to use. Attached Figure Description

[0019] Figure 1 This is a reaction route diagram for the synthesis of 2SiDDGMAPB according to the present invention.

[0020] Figure 2 This is a reaction route diagram for the synthesis of 3SiDDGMAPB according to the present invention.

[0021] Figure 3 Infrared spectra of different substances: a: Infrared spectrum of N,N-dimethyldipropylenetriamine, b: Infrared spectrum of D-glucono-δ-lactone, c: Infrared spectrum of the precursor, d: 3-chloropropylmethyldimethoxysilane, e: 2SiDDGMAPB.

[0022] Figure 4 Infrared spectra of different substances: a: Infrared spectrum of N,N-dimethyldipropylenetriamine, b: Infrared spectrum of D-glucono-δ-lactone, c: Infrared spectrum of the precursor, d: 3-chloropropyltrimethoxysilane, e: 3SiDDGMAPB.

[0023] Figure 5 For 2SiDDGMAPB 1 H-NMR spectrum.

[0024] Figure 6 For 2SiDDGMAPB 13 C-NMR spectrum.

[0025] Figure 7 For 3SiDDGMAPB 1 H-NMR spectrum.

[0026] Figure 8 For 3SiDDGMAPB 13 C-NMR spectrum.

[0027] Figure 9 The foaming properties of aqueous solutions of 2SiDDGMAPB product prepared with pure water at different concentrations.

[0028] Figure 10 The foaming properties of aqueous solutions of 3SiDDGMAPB product prepared with pure water at different concentrations.

[0029] Figure 11 The graph shows the change in foam height over time at different concentrations of the 2SiDDGMAPB product aqueous solution prepared with pure water.

[0030] Figure 12 The graph shows the change in foam height over time for aqueous solutions of 3SiDDGMAPB prepared from pure water at different concentrations.

[0031] Figure 13 The graph shows the change in foam height over time for aqueous solutions of 2SiDDGPBH and 3SiDDGPBH prepared from pure water and common surfactants.

[0032] Figure 14 The graph shows the foam height of aqueous solutions of 2SiDDGPBH and 3SiDDGPBH prepared with standard hard water and common surfactants over time.

[0033] Figure 15 The graph shows the change in foam height over time for aqueous solutions of 2SiDDGPBH and 3SiDDGPBH prepared from tap water and common surfactants. Detailed Implementation

[0034] To facilitate understanding of the present invention, a more comprehensive description will be provided below. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a thorough and complete understanding of the disclosure of the present invention. Example 1

[0035] (1) Synthesis of the precursor DDGPD D-glucono-δ-lactone and N,N-dimethyldipropyltriamine were added to a four-necked round-bottom flask equipped with a thermometer and a condenser. Anhydrous ethanol was used as the solvent, and the mixture was heated in an oil bath at 85°C for 2 hours. After the reaction was complete, heating was stopped, and the mixture was allowed to cool. The solvent was removed using a rotary evaporator. The residue was washed three times with diethyl ether to remove unreacted starting materials. The product was then placed in a vacuum drying oven until constant weight, yielding the precursor DDGPD.

[0036] (2) Synthesis of intermediate DDGPDH The precursor DDGPD was dissolved in anhydrous ethanol and placed in a four-necked round-bottom flask. After reflux at 85°C for 6 hours, the reaction was stopped and allowed to cool. The solvent was removed using a rotary evaporator, and the residue was washed three times with diethyl ether to remove unreacted starting materials. The product was then placed in a vacuum drying oven to constant weight to obtain the intermediate DDGPDH.

[0037] (3) Synthesis of 2SiDDGMAPB An anhydrous ethanol solution of intermediate DDGPDH and 3-chloropropylmethyldimethoxysilane was added to a four-necked round-bottom flask. After reflux at 85°C for 36 hours, the reaction was stopped and allowed to cool. The solvent was removed using a rotary evaporator, and the residue was washed three times with diethyl ether to remove unreacted starting materials. The product was then placed in an electrically heated drying oven to constant weight to obtain the final product 2SiDDGMAPB.

[0038] IR: 3463 cm -1 (v(OH)), 2939.1 cm -1 and 2812.2 cm -1 (v(CH)in-CH2--or CH3),1649.8 cm -1 (ν(C=O) in amide) , 1556.7 cm -1 (v(NH)in amide), 1459 cm -1 (ν(CH)in-CH2-), 1079.9 cm -1 (ν(CN⁺)) 1 H-NMR(CDCl3, ppm): δ: 0.12 (s, 3H, SiC H3 ), 0.87 (t, 6H, N + CH2CH2(CH2)8CH2C H3 N + (CH3)2CH2CH2(CH2)8CH2C H3 ), 1.20 (m, 32H, N) +CH2CH2(C H2 )8CH2CH3, N + CH2CH2(C H2 )8CH2CH3),1.24 (t, 4H, N + CH2CH2(CH2)8C H2 CH3,N + (CH3)2CH2CH2(CH2)8C H2 CH3),1.29 (t,2H, N + CH2CH2C H2 SiCH3),1.30 (t, 4H, N + CH2C H2 (CH2)8CH2CH3, N + CH2C H2 (CH2)8CH2CH3),1.34 (t, 2H, N + CH2C H2 CH2SiCH3),1.73 (m, 2H, NHCH2C H2 CH2N + ), 1.81 (m, 2H, N + CH2C H2 CH2N + ),2.42 (m, 1H, COCH(O H )CH(OH)CH(OH)CH(OH)CH2OH), 3.23 (t, 2H,NHC H2 CH2CH2N + ), 3.25 (t, 12H, N + (C H2 )3C H2 CH2C H2 N + (CH3)2C H2 CH2(CH2)8C H2 CH3), 3.31(s, 6H, Si(OC H3 )2CH3), 3.35 (m, 1H, COCH(OH)CH(OH)CH(OH)C H (OH)CH2OH), 3.37 (m,1H, COCH(OH)CH(OH)C H (OH)CH(OH)CH2OH), 3.45 (s, 6H, N + (C H32CH2CH2(CH2)8CH2CH3), 3.51 (m, 2H, COCH(OH)CH(OH)CH(OH)CH(OH)C H2 (OH), 3.67 (m, 1H, COCH(OH)C H (OH)CH(OH)CH(OH)CH2OH), 3.72 (m, 1H, COCH(OH)CH(OH)CH(OH)CH(OH)CH2O H ), 3.74 (m, 3H,COCH(OH)CH(O H CH(O) H CH(O) H (CH2OH), 3.78 (m, 1H, COC) H (OH)CH(OH)CH(OH)CH(OH)CH2OH), 8.08 (t, 1H, CON H )。

[0039] 13 C-NMR(CDCl3, ppm): -2.56 (Si C H3), 13.22 (N + CH2 C H2CH2Si(OCH3)2CH3), 14.06 (N + (CH3)2CH2CH2CH2CH2(CH2)4CH2CH2CH2 C H3, N + CH2CH2CH2CH2(CH2)4CH2CH2CH2 C H3),14.09 (N + CH2 C H2CH2N + ), 22.64 (N + (CH3)2CH2CH2CH2CH2(CH2)4CH2CH2 C H2CH3), 23.95(NHCH2 C H2CH2N + ), 26.41 (N + (CH3)2CH2 C H2CH2CH2(CH2)4CH2CH2CH2CH3), 26.87 (N + (CH3)2CH2CH2 C H2CH2(CH2)4CH2CH2CH2CH3), 26.88 (N + CH2 CH2CH2CH2(CH2)4CH2CH2CH2CH3), 29.37 (N + (CH3)2CH2CH2CH2 C H2(CH2)4 C H2CH2CH2CH3, N + CH2CH2CH2 C H2(CH2)4 C H2CH2CH2CH3), 29.67 (N + (CH3)2CH2CH2CH2CH2( C H2)4CH2CH2CH2CH3, N + CH2CH2CH2CH2( C H2)4CH2CH2CH2CH3), 31.91 (N + (CH3)2CH2CH2CH2CH2(CH2)4CH2 C H2CH2CH3, N + CH2CH2CH2CH2(CH2)4CH2 C H2CH2CH3), 45.15 (Si(O C H3)2CH3), 50.95 (N + ( C H3)2CH2CH2CH2CH2(CH2)4CH2CH2CH2CH3), 51.54 (N + C H2CH2CH2CH2(CH2)4CH2CH2CH2CH3), 58.24 (N + C H2CH2CH2N + ), 61.68 (NH C H2CH2 C H2N + ), 65.98 (N + (CH3)2 C H2CH2CH2CH2(CH2)4CH2 C H2CH2CH3), 70.86 (N + CH2CH2 C H2N + ), 76.70 (N + C H2CH2CH2Si(OCH3)2CH3), 76.73 (NH C H2CH2CH2N + ), 76.80 (NHCH2C H2CH2N + ), 77.02 (COCH(OH)CH(OH)CH(OH)CH(OH) C H2OH), 77.33 (CO C H(OH)CH(OH)CH(OH)CH(OH)CH2OH), 77.37 (COCH(OH) C H(OH)CH(OH)CH(OH)CH2OH), 81.82 (COCH(OH)CH(OH) C H(OH)CH(OH)CH2OH), 81.55 (COCH(OH)CH(OH)CH(OH) C H(OH)CH2OH), 186.83 ( C ONH). Example 2

[0040] (1) Synthesis of the precursor DDGPD D-glucono-δ-lactone and N,N-dimethyldipropyltriamine were added to a four-necked round-bottom flask equipped with a thermometer and a condenser. Anhydrous ethanol was used as the solvent, and the mixture was heated in an oil bath at 85°C for 2 hours. After the reaction was complete, heating was stopped, and the reaction was allowed to cool. The solvent was removed using a rotary evaporator. The residue was washed three times repeatedly with diethyl ether to remove unreacted starting materials. The product was then placed in a vacuum drying oven until constant weight, yielding the precursor DDGPD.

[0041] (2) Synthesis of intermediate DDGPDH The precursor DDGPD was dissolved in anhydrous ethanol and placed in a four-necked round-bottom flask. After reflux at 85°C for 6 hours, the reaction was stopped and allowed to cool. The solvent was removed using a rotary evaporator, and the residue was washed three times with diethyl ether to remove unreacted starting materials. The product was then placed in a vacuum drying oven to constant weight to obtain the intermediate DDGPDH.

[0042] (3) Synthesis of 3SiDDGMAPB An anhydrous ethanol solution of intermediate DDGPDH and 3-chloropropyltrimethoxysilane was added to a four-necked round-bottom flask. After reflux at 85°C for 36 hours, the reaction was stopped and allowed to cool. The solvent was removed using a rotary evaporator, and the residue was washed three times with diethyl ether to remove unreacted starting materials. The product was then placed in an electrically heated drying oven to constant weight to obtain the final product 3SiDDGMAPB.

[0043] IR: 3463 cm -1 (v(OH)), 2939.1 cm -1 and 2812.2 cm-1 (v(C-H)in-CH2--or CH3),1649.8 cm -1 (ν(C=O) in amide) , 1556.7 cm -1 (v(N-H)in amide), 1459 cm -1 (ν(C-H)in-CH2-), 1085.5 cm -1 (ν(C-N⁺)) 1 H-NMR(CDCl3, ppm): δ: 0.7 (t, 2H, N + CH2CH2C H2 Si(OCH3)3), 0.81 (t, 6H, N + CH2CH2(CH2)8CH2C H3 , N + (CH3)2CH2CH2(CH2)8CH2C H3 ),1.19 (m, 42H, N + CH2 CH2(CH2)8CH2 CH3,N + (CH3)2CH2 CH2(CH2)8 CH2CH3, N + CH2C H2 CH2Si(OCH3)3),1.69 (t, 4H, NHCH2C H2 CH2N + ),1.78(t, 2H, N + CH2C H2 CH2N + ),2.36 (m, 1H, COCH(O H )CH(OH)CH(OH)CH(OH)CH2OH),3.23 (t,2H, NHC H2 CH2CH2N + ),3.29 (m, 12H, N + (C H2 )3C H2 CH2C H2 N + (CH3)2C H2 CH2(CH2)8CH2CH3), 3.47(m, 6H, N + (C H3 )2CH2CH2(CH2)8CH2CH3),3.50 (m, 1H, COCH(OH)CH(OH)C H(OH)CH(OH)CH2OH), 3.51 (t, 1H, COCH(OH)CH(OH)CH(OH)C H (OH)CH2OH), 3.62 (t, 2H, COCH(OH)CH(OH)CH(OH)CH(OH)C H2 OH), 3.64 (s, 9H, N + CH2CH2CH2Si(OC H3 )3), 3.75 (m, 1H, COCH(OH)C H (OH)CH(OH)CH(OH)CH2OH), 4.38 (m, 4H, COCH(OH)CH(O H )CH(O H )CH(O H )CH2O H ),4.59 (s, 1H, COC H (OH)CH(OH)CH(OH)CH(OH)CH2OH), 8.07 (t, 1H, CON H )。

[0044] 13 C-NMR(CDCl3, ppm): 7.16 (N + CH2 C H2CH2Si(OCH3)3), 7.60 (N + CH2CH2 C H2Si(OCH3)3), 14.09 (N + (CH3)2CH2CH2CH2CH2(CH2)4CH2CH2CH2 C H3), N + CH2CH2CH2CH2(CH2)4CH2CH2CH2 C H3), 18.26 (N + CH2 C H2CH2N + ), 22.67 (N + (CH3)2CH2CH2CH2CH2(CH2)4CH2CH2 C H2CH3), 22.93 (NHCH2 C H2CH2N + ), 26.88 (N + (CH3)2CH2 C H2CH2CH2(CH2)4CH2CH2CH2CH3), 28.88 (N +(CH3)2CH2CH2 C H2CH2(CH2)4CH2CH2CH2CH3), 29.31 (N + CH2 C H2CH2CH2(CH2)4CH2CH2CH2CH3), 29.37 (N + (CH3)2CH2CH2CH2 C H2(CH2)4 C H2CH2CH2CH3, N + CH2CH2CH2 C H2(CH2)4 C H2CH2CH2CH3), 29.44 (N + (CH3)2CH2CH2CH2CH2( C H2)4CH2CH2CH2CH3, N + CH2CH2CH2CH2( C H2)4CH2CH2CH2CH3), 31.89 (N + (CH3)2CH2CH2CH2CH2(CH2)4CH2 C H2CH2CH3, N + CH2CH2CH2CH2(CH2)4CH2 C H2CH2CH3), 32.65 (NHCH2 C H2CH2N + ), 45.16 (N + CH2CH2CH2Si(O C H3)3), 47.53 (N + ( C H3)2CH2CH2CH2CH2(CH2)4CH2CH2CH2CH3), 50.49 (NHCH2CH2 C H2N + ), 50.78 (N + C H2CH2CH2N + ),58.26 (N + C H2CH2CH2CH2(CH2)4CH2CH2CH2CH3), 58.51 (N + (CH3)2 C H2CH2CH2CH2(CH2)4CH2CH2CH2CH3), 58.58 (N + CH2CH2 C H2N +), 64.48 (N + C H2CH2CH2Si(OCH3)3), 70.79 (COCH(OH)CH(OH)CH(OH)CH(OH) C H2OH), 76.73 (CO C H(OH)CH(OH)CH(OH)CH(OH)CH2OH), 76.84(COCH(OH) C H(OH)CH(OH)CH(OH)CH2OH), 77.25 (COCH(OH)CH(OH) C H(OH)CH(OH)CH2OH),77.37 (COCH(OH)CH(OH)CH(OH) C H(OH)CH2OH), 171.21 ( C ONH). Example 3

[0045] Foam performance testing (1) The foaming properties of aqueous solutions of 2SiDDGMAPB and 3SiDDGMAPB prepared with pure water at different concentrations.

[0046] 2SiDDGMAPB and 3SiDDGMAPB products were prepared into aqueous solutions of 100 mg / L, 300 mg / L, 500 mg / L, 1 g / L, 2 g / L, and 5 g / L using pure water. The solutions were allowed to stand for 12 hours until they were homogeneous and stable. Their foaming properties were determined using a foam scanner and the blowing method. During the experiment, the gas flow rate was controlled at 150 mL / min, and the foaming time was controlled at 30 s, both of which were kept constant. The experimental results are shown below. Figure 9 and Figure 10 .

[0047] (2) The change of foam height of 2SiDDGMAPB and 3SiDDGMAPB with different concentrations over time.

[0048] 2SiDDGMAPB and 3SiDDGMAPB products were dissolved in pure water to prepare aqueous solutions of 100 mg / L, 300 mg / L, 500 mg / L, 1 g / L, 2 g / L, and 5 g / L, respectively. The solutions were allowed to stand for 12 hours until homogeneous and stable. The foaming properties at different concentrations were determined using a foam scanner and the bubbling method. During the experiment, the gas flow rate was controlled at 150 mL / min, and the foam height was controlled at 180 mL, both of which were kept constant. After each concentration experiment, the instrument was rinsed with pure water promptly to prevent cross-contamination. The experimental results are shown below. Figure 11 and Figure 12 .

[0049] (3) The foam height of 2SiDDGMAPB and 3SiDDGMAPB aqueous solutions prepared with pure water and common surfactants changes over time.

[0050] 2SiDDGMAPB and 3SiDDGMAPB products were prepared into 1 g / L aqueous solutions with pure water and allowed to stand for 12 h until the solution was homogeneous and stable. Their foaming properties were determined using a foam scanner and the bubbling method. During the experiment, the gas flow rate was controlled at 150 mL / min, and the foaming height was controlled at 180 mL, and both were kept constant. Dodecyl dimethyl benzyl ammonium chloride (1227), 3-(trimethoxysilyl)propyl dimethyl octadecyl ammonium chloride (DC-5700), sodium dodecyl sulfate (K12), and sodium fatty alcohol polyoxyethylene ether carboxylate (AEC9-Na) were treated in the same way as control samples. The experimental results are shown in […]. Figure 13 .

[0051] (4) Changes in foam height over time of standard hard water prepared aqueous solutions of 2SiDDGMAPB and 3SiDDGMAPB with common surfactants.

[0052] 2SiDDGMAPB and 3SiDDGMAPB products were prepared into 1 g / L aqueous solutions using standard hard water and allowed to stand for 12 h until the solution was homogeneous and stable. Their foaming properties were determined using a foam scanner and the bubbling method. During the experiment, the gas flow rate was controlled at 150 mL / min, and the foaming height was controlled at 180 mL, and both were kept constant. Dodecyl dimethyl benzyl ammonium chloride (1227), 3-(trimethoxysilyl)propyl dimethyl octadecyl ammonium chloride (DC-5700), sodium dodecyl sulfate (K12), and sodium fatty alcohol polyoxyethylene ether carboxylate (AEC9-Na) were treated in the same way as control samples. The experimental results are shown in […]. Figure 14 . (5) Changes in bubble height over time of 2SiDDGMAPB and 3SiDDGMAPB aqueous solutions prepared with tap water and common surfactants.

[0053] 2SiDDGMAPB and 3SiDDGMAPB products were prepared into 1 g / L aqueous solutions using tap water and allowed to stand for 12 hours until the solution was homogeneous and stable. Their foaming properties were determined using a foam scanner and the aeration method. During the experiment, the gas flow rate was controlled at 150 mL / min, and the foaming height was controlled at 180 mL, and both were kept constant. Dodecyl dimethyl benzyl ammonium chloride (1227), 3-(trimethoxysilyl)propyl dimethyl octadecyl ammonium chloride (DC-5700), sodium dodecyl sulfate (K12), and sodium fatty alcohol polyoxyethylene ether carboxylate (AEC9-Na) were treated in the same way as control samples. The experimental results are shown in [Figure number missing]. Figure 15 .

[0054] Depend on Figure 9 and Figure 10 It can be seen that both solutions exhibit excellent foaming properties, but the response characteristics of foam height to concentration differ significantly. Experimental results show that the foam height of the 2SiDDGMAPB solution increases significantly with increasing concentration, exhibiting a strong concentration dependence; while the foam height of the 3SiDDGMAPB solution remains relatively stable under different concentration conditions, showing less influence from concentration changes.

[0055] Depend on Figure 11 and Figure 12 It can be seen that 2 / 3SiDDGMAPB exhibits good foam stabilization performance across the tested concentration range, with an anomaly occurring only at 100 mg / L, where reduced foam film strength leads to insufficient liquid film stability. The foam height decreases with increasing concentration; this unique phenomenon may be related to changes in the critical micelle concentration or intermolecular interactions of the surfactant, and the specific mechanism requires further investigation and verification.

[0056] Depend on Figure 13 It can be seen that 2 / 3 SiDDGMAPB prepared with pure water and anionic surfactants exhibit comparable foam stabilization performance, with their foam stability essentially at the same level. This is similar to common surfactants (DC-5700, K...). 12 Compared to other products, these two new products exhibit superior foam stability, with longer foam retention time and a more stable foam structure.

[0057] Depend on Figure 14 As can be seen, under standard hard water conditions, 2 / 3SiDDGMAPB exhibits similar foam-stabilizing properties to anionic surfactants, and both are significantly superior to conventional surfactant products. It is noteworthy that the foam-stabilizing effect of 2 / 3SiDDGMAPB in hard water is essentially consistent with its performance in pure water, which may be due to the significant improvement in hard water resistance caused by the introduction of sugar groups.

[0058] Depend on Figure 15 It can be seen that the foam stabilization performance of 2SiDDGMAPB decreased rapidly in the tap water system. In contrast, the foam stabilization performance of 3SiDDGMAPB was basically equivalent to that of anionic surfactants, only decreasing after 900s, but it was significantly better than common surfactant products. However, it performed slightly worse than pure water and standard hard water systems, which may be due to the complex synergistic effect of ions in tap water. Example 4

[0059] Minimum inhibitory concentration: According to Section 2.8.1.4 of the "Disinfection Technical Specifications" (2002 edition).

[0060] Table 1.2 Experimental results of the minimum inhibitory concentration of SiDDGMAPB

[0061] As shown in Table 1, the minimum inhibitory concentration (MIC) of 2SiDDGMAPB against Escherichia coli 8099 is 0.002%. The MIC of 2SiDDGMAPB against Staphylococcus aureus ATCC6538 is 0.001%.

[0062] Table 2.3 Experimental results of minimum inhibitory concentration of SiDDGMAPB

[0063] As shown in Table 2, the minimum inhibitory concentration (MIC) of 3SiDDGMAPB against Escherichia coli 8099 is 0.002%. The MIC of 3SiDDGMAPB against Staphylococcus aureus ATCC6538 is 0.001%.

[0064] Example 5 Acute oral toxicity test: According to Section 2.3.1 of the "Disinfection Technical Specifications" (2002 edition). Table 3.3 Results of acute oral toxicity tests of SiDDGMAPB

[0065] Table 3 shows the median lethal dose (LD50) of 3SiDDGMAPB in mice. 50 The acute toxicity dose classification of the product is 5025.8 mg / kg·BW (greater than 5000 mg / kg·BW), and it is practically non-toxic.

[0066] Example 6 Skin irritation test: according to Section 2.3.3 of the "Disinfection Technical Specifications" (2002 edition).

[0067] Table 4.3 Results of skin irritation test of SiDDGMAPB

[0068] As shown in Table 4, the skin irritation index of the 3SiDDGMAPB product on New Zealand rabbits was 0.33, indicating that the skin irritation intensity was non-irritating.

[0069] The above description is only for better explaining the embodiments of the present invention and is not intended to limit them. Any modifications or equivalent substitutions that do not depart from the spirit and scope of the present invention shall fall within the scope of the present invention.

Claims

1. A high-foaming glycosylamide organosilicon cationic surfactant, characterized in that, It has the following structural formula: or 。 2. The method for preparing the high-foaming glycosylamide organosilicon cationic surfactant according to claim 1, characterized in that, Includes the following steps: Step 1: Dissolve D-gluconate-δ-lactone and N,N-dimethyldipropyltriamine in anhydrous ethanol and react them with an amine ester to obtain the precursor N,N-dimethyldipropene-N(3-glycosylamide). Step 2: Dissolve the precursor N,N-dimethyldipropene-N(3-glycosylamide) and bromododecane in anhydrous ethanol, and obtain a double-long-chain glycosyl quaternary ammonium salt containing amide bonds through a substitution reaction, which is the intermediate; Step 3: Dissolve the intermediate with 3-chloropropylmethyldimethoxysilane or 3-chloropropyltrimethoxysilane in anhydrous ethanol, and then perform a quaternization reaction to obtain a double long carbon chain organosilicon quaternary ammonium salt containing glycosyl amide bonds, which is the surfactant.

3. The method for preparing the high-foaming glycosylamide organosilicon cationic surfactant according to claim 2, characterized in that, In step 1, the molar ratio of D-glucono-δ-lactone to N,N-dimethyldipropylenetriamine is 1.01:1.

0.

4. The method for preparing the high-foaming glycosylamide organosilicon cationic surfactant according to claim 2, characterized in that, In step 1, the temperature of the amine ester reaction is 85°C, and the time is 1-2 h.

5. The method for preparing the high-foaming glycosylamide organosilicon cationic surfactant according to claim 2, characterized in that, In step 2, the molar ratio of the precursor N,N-dimethyldipropene-N(3-glycosylamide) to bromododecane is 1.0:2.

01.

6. The method for preparing the high-foaming glycosylamide organosilicon cationic surfactant according to claim 2, characterized in that, The substitution reaction in step 2 is carried out at a temperature of 85°C for 5-6 hours.

7. The method for preparing the high-foaming glycosylamide organosilicon cationic surfactant according to claim 2, characterized in that, In step 3, the molar ratio of the intermediate to 3-chloropropylmethyldimethoxysilane or 3-chloropropyltrimethoxysilane is 1.0:1.

01.

8. The method for preparing the high-foaming glycosylamide organosilicon cationic surfactant according to claim 2, characterized in that, The quaternization reaction in step 3 is carried out at a temperature of 85°C for 32-36 hours.

9. The application of the high-foaming glycosylamide organosilicon cationic surfactant according to claim 1 in antibacterial detergents, medical disinfectants, and high-end cosmetics.

Images