Multifunctional organic silicon glycosyl amide 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 multifunctional organic silicon glycosyl amide cationic surfactant as well as a preparation method and application thereof. The preparation method of the surfactant comprises the following steps: carrying out amine ester reaction on glucolactone and N, N-dimethyl dipropylene triamine to obtain a precursor; carrying out substitution reaction on the precursor and bromododecane to obtain an intermediate; the intermediate and 3-chloropropyl methyl dimethoxy silane or 3-chloropropyl methyl trimethoxy silane are subjected to a quaternization reaction, and the surfactant is obtained. The surfactant has good environmental protection property and biocompatibility, is non-toxic and non-irritant, can sterilize and improve the rewettability of the material surface, and has wide application prospects in the aspects of pesticide, textile, daily chemical industry and material transportation and storage.

Description

Technical Field

[0001] The invention belongs to the technical field of organic compounds, and specifically relates to a multifunctional organosilicon glycosyl amide cationic surfactant and a preparation method and application thereof. Background Art

[0002] In recent years, with the increasing awareness of environmental protection and the rise of green chemistry, the development of environmentally friendly surfactants with excellent performance has become a research hotspot in the chemical industry. Surfactants, as a raw material for organic chemicals, are widely used in daily chemicals, leather, oil production, metallurgy, pharmaceuticals, food and other fields. Traditional surfactants are mostly made from petrochemical products, which are not only non-renewable, but also easily pollute the environment during use and degradation. Therefore, it is of great practical significance to synthesize a surfactant that can last for a long time, has excellent performance, is renewable and environmentally friendly.

[0003] Sugar-based cationic surfactants are a new type of surfactant. Sugar is used as a raw material and introduced into the cationic structure through chemical modification. This type of surfactant not only has the characteristics of sugar-based degradation, regeneration, improved re-wettability, and low toxicity, but also has the function of cationic sterilization. However, because it has no chemical bonds directly connected to the surface of fabrics and fibers, the effective substances are very easy to fall off after washing or friction, and there is no lasting bactericidal, antibacterial, re-wettability and other properties. The introduction of siloxane groups into the quaternary ammonium salt structure allows the product to be firmly combined with the surface of the object and exert its lasting and stable effect. At present, there is no product on the market that combines the advantages of silicone and glycosylamide quaternary ammonium salts, so it is very important to develop a new multifunctional surfactant that is green, environmentally friendly, non-toxic, harmless, long-lasting, and can repeatedly exert its various properties. Summary of the invention

[0004] In view of the current market demand for low-toxic, green, long-acting and multifunctional surfactants and the fact that there are few reports on organosilicon glycosylamide quaternary ammonium salts, the present invention provides a new surfactant that combines the advantages of glycosylamide quaternary ammonium salts and organosilicon quaternary ammonium salts, as well as a preparation method and application thereof.

[0005] To achieve the above object, the technical solution of the present invention is as follows:

[0006] In a first aspect, the present invention provides a multifunctional organosilicon glycoside amide cationic surfactant having the following structural formula:

[0007]

[0008] Wherein, R is a C12 long-chain hydrocarbon group.

[0009] In a second aspect, the present invention provides a method for preparing the multifunctional organosilicon glycoside amide cationic surfactant according to the first aspect, comprising the following steps:

[0010] Step 1: reacting gluconolactone with N,N-dimethyldipropylenetriamine to obtain a precursor N,N-dimethyldipropylene-N(3-glycosylamide);

[0011] Step 2: The precursor N,N-dimethyldipropylene-N(3-glycosylamide) is subjected to substitution reaction with bromoalkane to obtain a single-chain glycosyl salt containing an amide bond, which is an intermediate;

[0012] Step 3: The intermediate is subjected to a quaternization reaction with 3-chloropropylmethyldimethoxysilane or 3-chloropropylmethyltrimethoxysilane to obtain a double-chain organosilicon quaternary ammonium salt containing a glycosylamide bond, which is the organosilicon glycosylamide cationic surfactant.

[0013] In some embodiments of the present invention, the molar ratio of gluconolactone to N,N-dimethyldipropylenetriamine in step 1 is 1.0-1.01:1.0.

[0014] In some embodiments of the present invention, the conditions for the amine ester reaction in step 1 are: the solvent is ethanol, the reaction is carried out under reflux conditions, and the reaction time is 1 hour.

[0015] In some embodiments of the present invention, in step 2, the molar ratio of the precursor N,N-dimethyldipropylene-N(3-glycosylamide) to the bromoalkane is 1.0:1.0-1.01.

[0016] In some embodiments of the present invention, the conditions for the substitution reaction in step 2 are: the solvent is ethanol, the reaction is carried out under reflux conditions, and the reaction time is 4 to 5 hours.

[0017] In some embodiments of the present invention, the bromoalkane in step 2 is a long-chain C12 straight-chain alkyl bromoalkane.

[0018] In some embodiments of the present invention, the molar ratio of the intermediate to 3-chloropropylmethyldimethoxysilane or 3-chloropropylmethyltrimethoxysilane in step 3 is 1.0:1.01.

[0019] In some embodiments of the present invention, the conditions for the quaternization reaction in step 3 are: the solvent is ethanol, the reaction is carried out under reflux, and the reaction time is 24 to 30 hours.

[0020] In a third aspect, the present invention provides the use of the multifunctional organosilicon glycosylamide cationic surfactant described in the first aspect for preparing antibacterial materials or wettable materials.

[0021] Compared with the prior art, the present invention has the following beneficial effects:

[0022] 1. The surfactant of the present invention has good environmental protection. The sugar base is derived from natural sugars, which is a renewable resource. It can replace non-renewable resources such as petroleum and coal, thereby increasing the sustainable development of amine products.

[0023] 2. The surfactant of the present invention belongs to a glycosylamide cationic surfactant, and combines the characteristics of an organosilicon group. After the methoxyl group on the organosilicon structure is hydrolyzed, it is connected to the surface of the material through chemical bonds, giving the material a long-lasting effect of wear resistance and water washing resistance.

[0024] 3. The surfactant of the present invention improves the problem of poor rewetting of traditional organosilicon quaternary ammonium salts, and greatly improves the rewetting performance on the surfaces of leather, acrylic plates, leaves, and wooden materials, especially the surfaces of leaves and wooden materials, and has a long-lasting wetting effect. It has broad application prospects in pesticides, daily chemicals, and material transportation and storage.

[0025] 4. The surfactant of the present invention has good biocompatibility and belongs to bio-based chemicals. It is non-toxic and non-irritating while having excellent performance (see the surfactant toxicity / irritation analysis and test report provided by Guangdong Microbiological Analysis and Testing Center), and is safer to use.

[0026] 5. The surfactant of the present invention has a long-lasting antibacterial property and has potential application value in antibacterial materials. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 The following is a reaction scheme for synthesizing 2SiDDGPBH according to the present invention.

[0028] Figure 2 The following is a reaction scheme for synthesizing 3SiDDGPBH according to the present invention.

[0029] Figure 3 Infrared spectra of different substances; a: infrared spectrum of N,N-dimethyldipropylenetriamine, b: infrared spectrum of gluconolactone, c: infrared spectrum of precursor, d: 3-chloropropylmethyldimethoxysilane, e: 2SiDDGPBH.

[0030] Figure 4 For 2SiDDGPBH 1 H-NMR spectrum.

[0031] Figure 5 For 2SiDDGPBH 13 C-NMR spectrum.

[0032] Figure 6 For 3SiDDGPBH 1 H-NMR spectrum.

[0033] Figure 7 For 3SiDDGPBH 13 C-NMR spectrum.

[0034] Figure 8 Schematic diagram of the contact angle of the aqueous solution prepared with 2SiDDGPBH and 3SiDDGPBH products on the surface of leaves.

[0035] Fig. 9 Schematic diagram of the contact angle of the aqueous solution prepared with 2SiDDGPBH and 3SiDDGPBH products on the leather surface.

[0036] Fig.10 Schematic diagram of the contact angle of the aqueous solution prepared with 2SiDDGPBH and 3SiDDGPBH products on the surface of acrylic plate.

[0037] Fig.11 Schematic diagram of the contact angle of the aqueous solution prepared with 2SiDDGPBH and 3SiDDGPBH products on the oil paper surface. DETAILED DESCRIPTION

[0038] In order to facilitate understanding of the present invention, the present invention will be described more fully below. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0039] Example 1

[0040] (1) Synthesis of the precursor N,N-dimethyldipropylene-N(3-glycosylamide) (DDGPD)

[0041] In a 250mL three-necked round-bottom flask equipped with a thermometer and a spherical condenser, add 25.94g (163mmol) of N,N-dimethyldipropylenetriamine, 29.3g (165mmol) of gluconolactone, and 70mL of anhydrous ethanol. React under reflux conditions, and let stand to cool after 1h of reaction. Use a rotary evaporator to evaporate the solvent, and wash the resulting product with ether 3 times to obtain 52.68g of a light yellow powder solid (DDGPD), with a yield of 95.37%.

[0042] (2) Synthesis of intermediates

[0043] In a 250mL three-necked round-bottom flask equipped with a thermometer and a spherical condenser, add 52g (154mmol) of the precursor, 38.76g (155mmol) of dodecane bromide, and 70mL of anhydrous ethanol. React under reflux conditions, and let stand to cool after 5h of reaction. Use a rotary evaporator to evaporate the solvent, and wash the resulting product with ether 3 times to obtain 86.83g of the intermediate, with a yield of 95.67%.

[0044] (3) Synthesis of 2SiDDGPBH

[0045] In a 250mL three-necked round-bottom flask equipped with a thermometer and a spherical condenser, add 80g (149mmol) of the intermediate, 27.50g (150mmol) of 3-chloropropylmethyldimethoxysilane, and 70mL of anhydrous ethanol. React under reflux conditions, let stand and cool after 24h of reaction, and then wash the obtained product with ether 3 times to remove the unreacted raw materials. Finally, use a rotary evaporator to evaporate the solvent to obtain 101.45g of a light yellow viscous liquid (2SiDDGPBH), with a yield of 94.37%.

[0046] IR:3463cm -1 (v(O–H)),2931cm -1 and 2856cm -1 (v(C–H)in–CH2–or-CH3),1648cm -1 (ν(C=O)in amide),1536cm -1 (v(N–H)in amide),1459cm -1 (ν(C–H)in–CH2–).

[0047] 1 H-NMR(DMSO,ppm):δ:0.04(m,3H,SiC H3 ),0.50(d,2H,SiC H2 ),0.83(t,3H,NCH2(CH2) 10 C H3 ),1.22(s,20H,NCH2 (CH 2)5CH3),1.66(t,6H,NCH2C H 2CH2N + ,NCH2C H 2CH2N,SiCH2C H 2),2.09(s,4H,NC H 2CH2,NC H 2CH2),2.95(m,2H,NC H 2),3.05(s,6H,N + CH 3C H 3),3.31(s,1H,COCH(OH)CH(OH)CH(O H ),3.41(m,9H,Si(OC H 3)2,COCH(OH)3C H OHC H 2OH),3.55(t,2H,N + C H 2),3.68(m,4H,N(CH2CH2C H 2)2,3.92(s,1H,COCH(OH)3CHOHCH2O H ),4.03(d,1H,COCH(OH)C H (OH)),4.39(t,4H,COCH(O H )4CH2O H ),5.51(d,1H,COCH(O H ),7.97(s,1H,CON H )。

[0048] 13 C-NMR(DMSO,ppm):-4.91(Si C H3),11.04(N + CH2 C H2),13.94(N(CH2) 11 C H3),18.53(Si C H2),22.14(N(CH2) 10 C H2,NCH2 C H2CH2N + ),25.88(N(CH2)2 C H2),28.78(NCH2 C H2),29.09(N(CH2)3( C H2)7,31.35(NCH2 C H2CH2NH),39.52(N C H2CH2 C H2NH),50.07(SiO( C H3)2),56.04(N + ( C H3)2),57.51(N C H2CH2 C H2N + ),63.25(NCH2(CH2) 10CH3),63.70(COCHOHCHOHCHOHCHOH C H2OH),70.12(N + C H2),71.43(COCHOHCHOH C HOH C HOHCH2OH),72.25(COCHOH C HOHCHOHCHOHCH2OH),73.78(CO C HOH CHOH C HOH C HOHCH2OH).

[0049] Example 2

[0050] (1) Synthesis of the precursor N,N-dimethyldipropylene-N(3-glycosylamide) (DDGPD)

[0051] In a 250mL three-necked round-bottom flask equipped with a thermometer and a spherical condenser, add 25.93g (163mmol) of N,N-dimethyldipropylenetriamine, 28.93g (163mmol) of gluconolactone, and 70mL of anhydrous ethanol. React under reflux conditions, and let stand to cool after 1h of reaction. Use a rotary evaporator to evaporate the solvent, and wash the resulting product with ether 3 times to obtain 51.98g of a light yellow powder solid (DDGPD), with a yield of 94.13%.

[0052] (2) Synthesis of intermediates

[0053] In a 250mL three-necked round-bottom flask equipped with a thermometer and a spherical condenser, add 51g (151mmol) of the precursor, 37.75g (151mmol) of dodecane bromide, and 70mL of anhydrous ethanol. React under reflux conditions, and let stand to cool after 4h of reaction. Use a rotary evaporator to evaporate the solvent, and wash the resulting product with ether 3 times to obtain 84.59g of the intermediate, with a yield of 94.77%.

[0054] (3) Synthesis of 3SiDDGPBH

[0055] In a 250mL three-necked round-bottom flask equipped with a thermometer and a spherical condenser, add 80g (149mmol) of the intermediate, 29.80g (150mmol) of 3-chloropropylmethyltrimethoxysilane, and 70mL of anhydrous ethanol. React under reflux conditions, let stand and cool after 30h of reaction, and then wash the obtained product with ether 3 times to remove the unreacted raw materials. Finally, use a rotary evaporator to evaporate the solvent to obtain 104.49g of a light yellow solid (3SiDDGPBH), with a yield of 95.17%.

[0056] IR: 3463 cm -1 (v(O–H)), 2931 cm -1 and 2856 cm -1 (v(C–H) in –CH2– or -CH3), 1648 cm -1 (ν(C=O) in amide), 1536 cm -1 (v(N–H) in amide), 1459 cm -1 (ν(C–H) in –CH2–).

[0057] 1 H-NMR (DMSO, ppm): δ: 0.83 (t, 3H, N(CH2) 11 C H 3), 1.04 (t, 2H, SiC H 2), 1.22 (s, 20H, NCH2(C H 2) 10 CH3), 1.78 (t, 6H, NCH2(C H 2)2, N + CH2C H 2), 2.41 (s, 2H, NC H 2), 2.55 (s, 2H, NC H 2), 2.92 (t, 2H, NC H 2), 3.04 (t, 6H, NCH2CH2C H 2NH, NCH2CH2C H 2N + , N + C H 2), 3.15 (s, 6H, N + (C H 3)2, 3.28 (s, 1H, COCHOHCHOHC H OHCHOHCH2OH), 3.41 (m, 9H, SiO(C H 3)3), 3.43 (m, 3H, COCHOHCHOHCHOHC H OHC H 2OH), 3.74 (s, 2H, COCHOHC H OHCHOHCHOHCH2O H ), 3.91 (s, 2H, COC H OHCHOHCHO H CHOHCH2OH), 4.02 (t, 2H, COCHOHCHO H CHOHCHO H<h2 style=";text-align:left;direction:ltr">CH2OH), 5.30(s, 1H, COCHO<h2 style=";text-align:left;direction:ltr"> H <h2 style=";text-align:left;direction:ltr"> CHOHCHOHCHOHCH2OH),7.95(t,1H,CON<h2 style=";text-align:left;direction:ltr"> H <h2 style=";text-align:left;direction:ltr"> )。<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0058] <h2 style=";text-align:left;direction:ltr"> 13 <h2 style=";text-align:left;direction:ltr"> C-NMR(DMSO,ppm):5.85(N<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> CH2<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2), 13.98(N(CH2)<h2 style=";text-align:left;direction:ltr"> 11 <h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H3,18.56(Si<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2), 22.15(NCH2<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2CH2N<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> ,N(CH2)<h2 style=";text-align:left;direction:ltr"> 10 <h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2)25.88(NCH2CH2<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2), 28.62(NCH2<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2),28.78(N(CH2)3<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2),29.10(N(CH2)3CH2CH2(<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2)5),31.36(NCH2<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2CH2NH),39.52(N<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2CH2CH2NH),39.94(NCH2CH2<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2NH), 48.61(SiO(<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H3)3,50.12(N<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> (<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H3)2),55.06(N<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2CH2CH2N<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> ),56.07(N<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2(CH2)<h2 style=";text-align:left;direction:ltr"> 11 <h2 style=";text-align:left;direction:ltr"> CH3),63.27(NCH2CH2<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2N<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> ),63.68(COCHOHCHOHCHOHCHOH<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2OH), 70.16(N<h2 style=";text-align:left;direction:ltr"> + <h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> H2), 71.45(COCHOHCHOH<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> HOH<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> HOHCH2OH), 72.25(COCHOH<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> HOHCHOHCHOHCH2OH),73.70(CO<h2 style=";text-align:left;direction:ltr"> C <h2 style=";text-align:left;direction:ltr"> HOHCHOHCHOHCHOHCH2OH),173.37(<h2 style=";text-align:left;direction:ltr"> CONH).

[0059] Example 3

[0060] (1) Synthesis of the precursor N,N-dimethyldipropylene-N(3-glycosylamide) (DDGPD)

[0061] In a 250mL three-necked round-bottom flask equipped with a thermometer and a spherical condenser, add 25.94g (163mmol) N,N-dimethyldipropylenetriamine, 29.1g (164mmol) gluconolactone, and 70mL anhydrous ethanol. React under reflux conditions, and let stand to cool after 1h of reaction. Use a rotary evaporator to evaporate the solvent, and wash the resulting product with ether 3 times to obtain 51.73g of light yellow powder solid (DDGPD), with a yield of 93.35%.

[0062] (2) Synthesis of intermediates

[0063] In a 250mL three-necked round-bottom flask equipped with a thermometer and a spherical condenser, add 51g (151mmol) of the precursor, 37.75g (151mmol) of dodecane bromide, and 70mL of anhydrous ethanol. React under reflux conditions, and let stand to cool after reacting for 4.5h. Use a rotary evaporator to evaporate the solvent, and wash the resulting product with ether three times to obtain 83.36g of the intermediate, with a yield of 93.94%.

[0064] (3) Synthesis of 2SiDDGPBH

[0065] In a 250mL three-necked round-bottom flask equipped with a thermometer and a spherical condenser, add 80g (149mmol) of the intermediate, 27.50g (150mmol) of 3-chloropropylmethyldimethoxysilane, and 70mL of anhydrous ethanol. React under reflux conditions, let stand and cool after 27h of reaction, and then wash the obtained product with ether 3 times to remove the unreacted raw materials. Finally, use a rotary evaporator to evaporate the solvent to obtain 101.62g of a light yellow viscous liquid (2SiDDGPBH), with a yield of 94.53%.

[0066] Example 4

[0067] Wetting performance test:

[0068] (1) Rewetting on fabric

[0069] The rewetting properties of the products prepared in Examples 1 and 2 were evaluated according to the National Standard of the People's Republic of China QB / T 4309 "Determination of Rewetting Properties of Fabric Softeners". They were also compared with dimethyloctadecyl[3-(trimethoxysilyl)propyl]quaternary ammonium chloride (DC-5700), a common organosilicon quaternary ammonium salt product on the market.

[0070] Table 1 Measurement of capillary effect of solutions with a concentration of 1 g / L

[0071]

[0072] Table 2 Measurement of capillary effect of solutions with a concentration of 2 g / L

[0073]

[0074]

[0075] It can be seen from Tables 1 and 2 that the rewetting properties of 2SiDDGPBH and 3SiDDGPBH products on standard fabrics are greatly improved compared to DC-5700, with the rewetting properties increased by 3-4 times.

[0076] (2) Contact angle on leaves

[0077] 2SiDDGPBH and 3SiDDGPBH products were prepared into 2g / L aqueous solutions, fresh leaves were picked and soaked in the sample aqueous solution for 12 hours to make the organosilicon quaternary ammonium salt adhere evenly. The treated leaves were naturally dried in the shade and flattened, and the contact angle of pure water on the material surface was measured on a fully automatic contact angle meter. Distilled water and DC-5700 were used to treat the material in the same way as a control sample. The experimental results are shown in Figure 8 .

[0078] (3) Contact angle on leather

[0079] Prepare 2SiDDGPBH and 3SiDDGPBH products into a 2g / L aqueous solution, soak the clean leather in the sample aqueous solution for 12 hours to make the organosilicon quaternary ammonium salt adhere evenly. After the leather is treated, dry it naturally in the shade and flatten it. Measure the contact angle of pure water on the surface of the material on an automatic contact angle meter. Take pure water and DC-5700 to treat the material in the same way as a control sample. The experimental results are shown in Fig. 9 .

[0080] (4) Contact angle on acrylic plate

[0081] 2SiDDGPBH and 3SiDDGPBH products were prepared into a 2g / L aqueous solution. The clean acrylic plate was soaked in the sample aqueous solution for 12 hours to make the silicone quaternary ammonium salt adhere evenly. The contact angle of pure water on the material surface was measured on a fully automatic contact angle meter. Pure water and DC-5700 were used to treat the material in the same way as a control sample. The experimental results are shown in Fig.10 .

[0082] (5) Contact angle on oil paper

[0083] 2SiDDGPBH and 3SiDDGPBH products were prepared into a 2g / L aqueous solution. The prepared oil paper was soaked in the sample aqueous solution for 12 hours to make the silicone quaternary ammonium salt adhere evenly. The contact angle of pure water on the material surface was measured on a fully automatic contact angle meter. Pure water and DC-5700 were used to treat the material in the same way as a control sample. The experimental results are shown in Fig.11 .

[0084] according to Figure 10-11 It can be seen that after treating different materials with aqueous solutions prepared from 2SiDDGPBH and 3SiDDGPBH products, the contact angle between the solution and the material is greatly reduced, the wetting performance is greatly improved, and the wetting effect of 2SiDDGPBH is better than that of 3SiDDGPBH. The wetting performance after treatment with DC-5700 is even worse than that of pure water. The contact angle of the product 2SiDDGPBH of the present invention on the surface of the above four materials can be reduced to about 20°. Therefore, when the developed product is used as a pesticide insecticide, it has good wetting and spreading effects, which greatly improves the efficacy. The same effect can also be achieved in the scenario of preventing mildew in the transportation of leather and paper.

[0085] Example 5

[0086] Determination of antibacterial properties:

[0087] The synthesized 2SiDDGPBH and 3SiDDGPBH were prepared into a 10 g / L solution and sprayed on the surface of the glass plate with plastic wrap at a spraying volume of 0.8 ml / cm 2 , with a cycle of 30 days, use the Hygiena-ATP fluorescence tester to test in a 10cm*10cm square area, and wipe the surface of the plastic wrap once a day with a disposable dry cloth.

[0088] Table 3 Test results of antibacterial properties of cling film

[0089] Days / day 2SiDDGPBH 3SiDDGPBH Pure water comparison sample 1 2 8 169 3 3 15 206 7 5 28 226 14 25 30 264 21 29 54 287 30 31 60 326

[0090] It can be seen from Table 3 that both organosilicon quaternary ammonium salts have obvious antibacterial effects, and 2SiDDGPBH has stronger antibacterial performance. It still has an antibacterial effect of more than 99% 7 days after spraying, and the antibacterial effect is 90% after 30 days.

[0091] Example 6

[0092] Long-term antibacterial test: According to GB / T 20944 Evaluation of antibacterial properties of textiles (oscillation method design experiment)

[0093] 1. Select JB-00 white cotton cloth as the cloth for the experiment, select a small sample of about 20g and use a hand-cranked washing bucket for pre-treatment washing. The test conditions are 40℃±3℃, bath ratio 1:30, and AATCC1993WOB phosphorus-free standard detergent concentration 0.2%. To prevent residual detergent from interfering with the antibacterial performance test, the sample should be fully cleaned at the end of the last procedure, and then dried or dried.

[0094] 2. Cut the cloth into 5mm×5mm pieces, take 0.5g±0.05g of each piece and soak it in 10g / L 2Si / 3SiDDLPBH solution for 12h, then dry it and wrap it with paper for later use.

[0095] 3. Place the small paper bag containing the sample and the conical flasks, test tubes, buffer solution, etc. used in the experiment into a high pressure sterilizer and sterilize at 121°C and 103 kPa for 15 minutes.

[0096] 4. Prepare 3 blank control conical flasks and add 50 ml of buffer solution to each. Prepare another 3 conical flasks and add 0.5 g of treated cloth and 50 ml of buffer solution.

[0097] 5. Add 5 ml of bacterial solution (concentration 3×10 5 ~4×10 5 ).

[0098] 6. After the blank control is shaken at a speed of 250r / min for 1 minute, a sample is taken to obtain a 0-contact sample, which is then diluted to an appropriate multiple and coated on the plate.

[0099] 7. All conical flasks are shaken regularly for 18 hours, and the dilution is applied to the plates after appropriate dilution.

[0100] 8. Take out the cloth pieces after the experiment and dry them, put them into a hand-cranked washing bucket and wash them multiple times according to the above washing conditions, dry them and set them aside. After 7 days, conduct the second oscillation antibacterial experiment, and the experimental process is the same as the first one.

[0101] From Table 4, it can be seen that the antibacterial rates of white cotton cloth treated with 2SiDDGPBH and 3SiDDGPBH at a concentration of 10 g / L against Staphylococcus aureus reached 97.27% and 98.12% respectively, and the antibacterial rates after washing 5 times can still reach 96% and 99%, indicating that this product can be firmly bonded to cotton cloth through chemical bonds and has a good long-term antibacterial effect.

[0102] Table 4 Test results of the bactericidal and antibacterial properties of the products on cotton fabrics

[0103]

[0104] Example 7

[0105] Toxicity and irritation: Tested according to methods 2.3.1 and 2.3.3 of Part 2 of Technical Specifications for Disinfection (2002 edition).

[0106] Table 5 Results of acute oral toxicity test of 2SiDDGPBH

[0107]

[0108] It can be seen from Table 5 that the LD50 of 2SiDDGPBH to mice is greater than 5000 mg / kg·BW, and the acute toxicity dose classification of the product is practically non-toxic.

[0109] Table 6 2SiDDGPBH skin irritation test results record

[0110]

[0111]

[0112] It can be seen from Table 6 that the skin irritation index of 2SiDDGPBH product to New Zealand rabbits is 0, and the skin irritation intensity is non-irritating.

[0113] The above description is only for better explaining the embodiments of the present invention, and is not intended to limit the present invention. Any modification or equivalent substitution that does not depart from the spirit and scope of the present invention shall fall within the scope of the present invention.

Claims

1. A multifunctional organosilicon glycoside amide cationic surfactant, characterized in that: It has the following structural formula: Wherein, R is a C12 long-chain hydrocarbon group.

2. The method for preparing the multifunctional organosilicon glycoside amide cationic surfactant according to claim 1, characterized in that: The following steps are involved: Step 1: react gluconolactone with N,N-dimethyldipropylenetriamine to obtain a precursor N,N-dimethyldipropylene-N(3-glycosylamide); Step 2: The precursor N,N-dimethyldipropylene-N(3-glycosylamide) is subjected to substitution reaction with bromoalkane to obtain a single-chain glycosyl salt containing an amide bond, which is an intermediate; Step 3: The intermediate is subjected to a quaternization reaction with 3-chloropropylmethyldimethoxysilane or 3-chloropropylmethyltrimethoxysilane to obtain a double-chain organosilicon quaternary ammonium salt containing a glycosylamide bond, which is the organosilicon glycosylamide cationic surfactant.

3. The method for preparing the multifunctional organosilicon glycoside amide cationic surfactant according to claim 2, characterized in that: In the step 1, the molar ratio of gluconolactone to N,N-dimethyldipropylenetriamine is 1.0-1.01:1.

0.

4. The method for preparing the multifunctional organosilicon glycoside amide cationic surfactant according to claim 2, characterized in that: The conditions for the amine ester reaction in step 1 are: the solvent is ethanol, the reaction is carried out under reflux, and the reaction time is 1 hour.

5. The method for preparing the multifunctional organosilicon glycoside amide cationic surfactant according to claim 2, characterized in that: In the step 2, the molar ratio of the precursor N,N-dimethyldipropylene-N(3-glycosylamide) to the bromoalkane is 1.0:1.0-1.

01.

6. The method for preparing the multifunctional organosilicon glycoside amide cationic surfactant according to claim 2, characterized in that: The conditions for the substitution reaction in step 2 are: the solvent is ethanol, the reaction is carried out under reflux, and the reaction time is 4 to 5 hours.

7. The method for preparing the multifunctional organosilicon glycoside amide cationic surfactant according to claim 2, 5 or 6, characterized in that: In the step 2, the alkyl bromide is a long-chain C12 straight-chain alkyl bromide.

8. The method for preparing the multifunctional organosilicon glycoside amide cationic surfactant according to claim 2, characterized in that: In the step 3, the molar ratio of the intermediate to 3-chloropropylmethyldimethoxysilane or 3-chloropropylmethyltrimethoxysilane is 1.0:1.

01.

9. The method for preparing the multifunctional organosilicon glycoside amide cationic surfactant according to claim 2, characterized in that: The conditions for the quaternization reaction in step 3 are: the solvent is ethanol, the reaction is carried out under reflux, and the reaction time is 24 to 30 hours.

10. The use of the multifunctional organosilicon glycoside amide cationic surfactant according to claim 1, characterized in that: Used to prepare antibacterial materials or wettable materials.

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