CN106823984B - A kind of abietyl tertiary amine class surfactant and its preparation method and application - Google Patents

A kind of abietyl tertiary amine class surfactant and its preparation method and application Download PDF

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Publication number
CN106823984B
CN106823984B CN201611199659.XA CN201611199659A CN106823984B CN 106823984 B CN106823984 B CN 106823984B CN 201611199659 A CN201611199659 A CN 201611199659A CN 106823984 B CN106823984 B CN 106823984B
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rosin
preparation
abietyl
tertiary amine
formula
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CN106823984A (en
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韩春蕊
林海霞
刘泽学
杨俊�
杨明生
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Beijing Forestry University
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Beijing Forestry University
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/28—Unsaturated compounds polycyclic
    • C07C61/29—Unsaturated compounds polycyclic having a carboxyl group bound to a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/40—Unsaturated compounds containing halogen

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

The present invention relates to technical field of surfactant more particularly to abietyl tertiary amine class surfactant and its preparation method and application.It is 15, R CH that the abietyl tertiary amine class surfactant, which has structure shown in Formulas I and formula II, wherein n,3Or C2H5.The surfactant that the present invention is prepared has good surface-active and bacteriostatic activity, while having excellent water solubility and emulsifying capacity, can be used in antibacterial field of daily chemicals.

Description

A kind of abietyl tertiary amine class surfactant and its preparation method and application
Technical field
The present invention relates to field of fine chemical more particularly to a kind of abietyl tertiary amine class surfactant and preparation method thereof And application.
Background technology
The requirement of Surfactant is higher and higher at present, and not requiring nothing more than surfactant has unique property, also wants There is the feature of environmental protection outstanding.Relatively easy due to synthesizing and purifying, quaternary cationic surfactant is more one of research Kind.
Rosin is a kind of abundant renewable natural resources, cheap, synthesis surfactant generally have compared with Good ecological performance, meets " environmentally protective " this theme.Its main component is resin acid, and rosin acid is by with excellent Lipophilic ternary phenanthrene skeleton structure and with slightly water-wet carboxyl composition parents' molecule, rosin ternary phenanthrene ring structure tool There is good oleophylic performance, good surface-active can be used as after being connect with hydrophilic radical, and due to the hydrophobic performance of rosin Relatively strong, being coupled the compound obtained after hydrophilic group has good some surface active property.Using rosin as Material synthesis high added value Surfactant be studied extensively.
Abietyl esters tertiary amine surfactant merged the flexibility of tertiary amine surfactant, antistatic property, emulsibility, Disinfection and the good surface property of esters surface active agent, highly-water-soluble have excellent emulsifying dispersivity, solubilising Property, thermal stability etc. and good compatibility, easily biological-degradable, lower irritation, electrolyte-resistant and antistatic Property, it is widely used in the industrial circles such as weaving, printing and dyeing, plastics, papermaking, leather and household chemicals.But pine on the market at present Perfume base tertiary amine class kinds of surfactants is still limited, it is therefore necessary to make to abietyl tertiary amine surfactant further Research.
Invention content
The first purpose of the invention is to provide a kind of abietyl tertiary amine surfactants, selected from Formulas I, II structure of formula One kind in compound：
Wherein, R is-CH3Or-C2H5, n is the integer of 1-5；Preferably, n is 1 or 2, most preferably, n 2.
Second purpose of the invention is to provide a kind of preparation method of abietyl tertiary amine surfactant：Under room temperature, CH2OH(CH2)nNR2With modified rosin acyl chlorides occur in a solvent esterification to get.
The solvent can be this field Conventional solvents, such as benzene organic solvent.
Wherein, the modified rosin acyl chlorides is using chloroform as solvent, by modified rosin and PCl3What reaction was prepared.Institute Modified rosin is stated to be obtained by modified dose of modification of rosin；The modifying agent is maleic acid or acrylic acid.The following reaction mechanism mechanism of reaction Indicate that rosin generates corresponding modified rosin acyl chlorides under the effect of different modifying agent：
In by maleic acid modified rosin preparation process, those skilled in the art can be according to this field routine method of modifying system It is standby, it is preferably made with the following method in the present invention：
Rosin is crushed, maleic acid is added when material temperature reaches 150-165 DEG C in heating melting, and controlling reaction temperature exists 180-190 DEG C, reaction terminates to be cooled to room temperature, separation water outlet, dry, washing, up to relatively pure Malaysia pine after re-dry It is fragrant.
In by acrylic acid modified rosin preparation process, those skilled in the art can be according to this field routine method of modifying system It is standby, it is preferably made with the following method in the present invention：
It takes rosin heating to 150-170 DEG C, acrylic acid is added to react, wash after reaction, obtain light yellow powder third Olefin(e) acid modified rosin.
Correspondingly, above two modified rosin acyl chlorides and CH2OH(CH2)nNR2The rosin of Formulas I or Formula II structure is obtained by the reaction Base tertiary amine：
(1)CH2OH(CH2)nNR2With modified rosin acyl chloridesOccur esterification to get Compound of formula I
(2)CH2OH(CH2)nNR2With modified rosin acyl chloridesEsterification occurs to get formula II compounds
Third purpose of the present invention is to provide any one of the above abietyl tertiary amine surfactant in antibacterial daily necessities Application.
The surfactant that the present invention is prepared has good surface-active and bacteriostatic activity, while having excellent Water-soluble and emulsifying capacity, can be used in antibacterial daily necessities field.
Description of the drawings
Fig. 1 is the IR spectrograms of I -1 compound of formula.
Fig. 2 is I -1 compound of formula13C NMR spectras.
Fig. 3 is I -1 compound of formula1H NMR spectras.
Fig. 4 is the IR spectrograms of I -2 compound of formula.
Fig. 5 is I -2 compound of formula13C NMR spectras.
Fig. 6 is I -2 compound of formula1H NMR spectras.
Fig. 7 is the IR spectrograms of II -1 compound of formula.
Fig. 8 is the IR spectrograms of II -2 compound of formula.
Specific implementation mode
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..The original arrived involved in embodiment Material or reagent are known product, and the operation being related to is this field customary technical operation unless otherwise specified.
Wherein, the amberol arrived involved in embodiment prepares as follows：100g rosin is crushed, heating melting, when When material temperature reaches 150-165 DEG C, 46g maleic acids are added, controlling reaction temperature maintains 8h, is cooled to room temperature at 180-190 DEG C, Separation water outlet, it is dry, it washs, up to relatively pure maleic rosin after re-dry.
The acrylic acid modified rosin arrived involved in embodiment prepares as follows：100g rosin is taken, 160 DEG C or so is heated to, adds 25mL acrylic acid reacts 4h, and washing obtains light yellow powder acrylic acid modified rosin.
The modified rosin acyl chlorides arrived involved in embodiment prepares as follows：100g modified rosins are taken, are dissolved in 150ml chloroforms, By PCl3It is added in four-hole bottle, modified rosin and PCl3Molar ratio be 1:The chloroform that modified rosin is slowly added dropwise in (2-3) is molten Liquid, reaction temperature are controlled at 55 DEG C, the reaction was continued 3h after being added dropwise, and reaction mixture is transferred to round-bottomed flask, after revolving The thick product modified rosin acyl chlorides of crocus.
The preparation of 1 formula of embodiment, I -1 compound
The amberol acyl chlorides of 0.01mol is dissolved in 15ml benzole solns, then is slowly dropped to 0.04mol N, N- In dimethylethanolamine benzole soln, the molar ratio of modified rosin acyl chlorides and N, N- dimethylethanolamines are 1：4, after five minutes to it Middle dropwise addition triethylamine 4mL acid binding agents obtain sticky compound I-1 after reaction 3h with revolving at room temperature.
Using method same as Example 1, by N, it is 1-5 (being not 1) that N- dimethylethanolamines, which replace with carbon atom number, Other alcohol, you can obtain the compound that n in compound of formula I is 1-5 (being not 1).
The preparation of 2 formula of embodiment, I -2 compound
The amberol acyl chlorides of 0.01mol is dissolved in 15ml benzole solns and is slowly dropped to 0.04mol N, N- diethyls In ethylethanolamine benzole soln, molar ratio is 1：4, triethylamine 4mL acid binding agents are added dropwise after five minutes, revolving is used after reacting 3h at room temperature Obtain sticky compound I-2.
Using method same as Example 2, by N, it is 1-5 (being not 1) that N- diethyl ethylene diamines, which replace with carbon atom number, Other alcohol, you can obtain the compound that n in compound of formula I is 1-5 (being not 1).
The preparation of 3 formula of embodiment, II -1 compound
The acrylic acid modified rosin acyl chlorides of 0.05mol is dissolved in 75ml benzole solns and is slowly dropped to 0.15mol N, N- bis- In methylethanolamine benzole soln, molar ratio is 1：3, triethylamine 5mL acid binding agents are added dropwise after five minutes, rotation is used after reacting 3h at room temperature Steaming obtains sticky compound ii -1.
Using method same as Example 3, by N, it is 1-5 (being not 1) that N- dimethylethanolamines, which replace with carbon atom number, Other alcohol, you can obtain the compound that n in II compound of formula is 1-5 (being not 1).
The preparation of 4 formula of embodiment, II -2 compound
The acrylic acid modified rosin acyl chlorides of 0.05mol is dissolved in 75ml benzole solns and is slowly dropped to 0.15mol N, N- bis- In ehtylethanolamine benzole soln, molar ratio is 1：3, triethylamine 5mL acid binding agents are added dropwise after five minutes, rotation is used after reacting 3h at room temperature Steaming obtains sticky compound ii -2.
Using method same as Example 4, by N, it is 1-5 (being not 1) that N- diethyl ethylene diamines, which replace with carbon atom number, Other alcohol, you can obtain the compound that n in II compound of formula is 1-5 (being not 1).
Structural characterization
I -1 compound of formula
IR spectrograms are as shown in Figure 1, compared with rosin, 1722cm-1And 1772cm-1For the C=O stretching vibration peaks of ester, 1078cm-1For C-O stretching vibration peaks, the C=C stretching vibration peaks in rosin acid skeleton are in 1466cm-1、1384cm-1With 1155cm-1Place occurs, 1028cm-1It is C-N stretching vibration peaks, 782cm-1、806cm-1And 834cm-1Place is C-N bending vibrations Peak illustrates the successful synthesis of chemical compounds I-a,13C spectrograms as shown in Fig. 2, parsing is as shown in table 1,1H spectrograms are as shown in Figure 3.
Table 1：- 1 compound of Formulas I13C spectrogram results
I -2 compound of formula
IR spectrograms are as shown in figure 3, compared with I -2 compound of formula, by 782cm-1、806cm-1And 834cm-1It is changed to 716cm-1、 757cm-1And 813cm-1, it is C-N flexural vibrations peaks, illustrates the successful synthesis of chemical compounds I-b,13C spectrograms are as shown in figure 4, parsing As shown in table 1,1H spectrograms are as shown in Figure 5.
Table 2：- 2 compound of Formulas I13C spectrogram results
II -1 compound of formula
IR spectrograms are as shown in fig. 7, compared with rosin, 1722cm-1For the C=O stretching vibration peaks of ester, 1078cm-1For C-O Stretching vibration peak, the C=C stretching vibration peaks in rosin acid skeleton are in 1461cm-1、1380cm-1And 1175cm-1Place occurs, 1043cm-1It is C-N stretching vibration peaks, 767cm-1、828cm-1And 885cm-1Place is C-N flexural vibrations peaks, illustrates compound ii -1 Successful synthesis.
II -2 compound of formula
IR spectrograms are as shown in fig. 7, compared with II-a of formula, by 767cm-1、828cm-1And 885cm-1It is changed to 762cm-1、 798cm-1And 818cm-1, it is C-N flexural vibrations peaks, illustrates the successful synthesis of compound ii -2.
Emulsifiability (EP) is tested
Formulas I -1, I-2 that the embodiment 1-4 of 40ml mass fractions 0.1% is prepared is added in 100ml has plug graduated cylinder, The aqueous solution and 40ml benzene of II-1, II-2 compound, up and down oscillation 5 times, stand 1min, then vibrate 5 times, are so repeated 5 times, so Record separates the time of 10mL water afterwards, and retest 3 times calculates its average value.
As a result it is respectively I-1, I-2, II-1, II-2 (63s, 79s, 340s, 352s).
With commercially available surfactant sodium dodecyl base benzene sulfonic acid sodium salt (SDBS) and cetyl trimethylammonium bromide (CTAB) It is compared, the emulsifiability of SDBS and CTAB are respectively 12s and 73s, I-1, I-2, the tetra- kinds of tertiary amines surfaces II-1, II-2 The emulsifiability of activating agent is superior to SDBS, and I-2, II-1, the emulsifiability of II-2 is also superior to CTAB.
Bacteriostasis property is tested
Bacteriostatic activity test method is filter paper enzyme
The bacterium solution of activation is equivalent to 0.5 Maxwell opacity tube i.e. 107Cfu/m L with sterile broth dilution to concentration.Straight Add bacterium solution 1m L in the sterilized petri dishes of diameter 9cm, be subsequently poured into and melted the M-H agar mediums for being cooled to 55 DEG C, rotates mixing. The sterilizing copper pipe that 6mm is used after to be solidified takes out culture medium in copper pipe, in hole in making a call to 4 holes on M-H agar with aseptic nipper It is separately added into 1 chemical compounds I -1 of embodiment, 4 compound ii -2 of embodiment, gentamicin, each 0.05m L of rosin, 37 DEG C of cultures 12h.It takes out plate and measures antibacterial circle diameter.
Observation：Without inhibition zone, indicated with 〝-〞；
Antibacterial circle diameter<10mm indicates slight antibacterial with 〝+〞；
Antibacterial circle diameter is between 10~15mm, with 〝 ++ and 〞 indicates that moderate is antibacterial；
Antibacterial circle diameter>15mm, with 〝 +++ 〞 indicates that height is antibacterial.
1 bacteriostatic activity of table
As seen from the results in Table 1,1 chemical compounds I -1 of embodiment, 4 compound ii -2 of embodiment bacteriostatic level to be equivalent to celebrating big Mycin has significant fungistatic effect.
According to the method described above detection embodiment 2 chemical compounds I -1 and embodiment 3 compound ii -2, fungistatic effect with The effect of embodiment 1,4 is suitable.
Although above the present invention is described in detail with a general description of the specific embodiments, On the basis of the present invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Cause This, these modifications or improvements, belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.

Claims (8)

1. a kind of abietyl tertiary amine surfactant, which is characterized in that with one kind in Formulas I, II structural compounds of formula：
Wherein, R is-CH3Or-C2H5, n is the integer of 1-5.
2. abietyl tertiary amine surfactant according to claim 1, which is characterized in that the R is-CH3Or-C2H5, n It is 1 or 2.
3. a kind of preparation method of abietyl tertiary amine surfactant, which is characterized in that under room temperature, CH2OH(CH2)nNR2 With modified rosin acyl chlorides occur in a solvent esterification to get；Wherein, R is-CH3Or-C2H5, n is the integer of 1-5；
The modified rosin acyl chlorides is using chloroform as solvent, by modified rosin and PCl3What reaction was prepared；
The modified rosin through maleic acid or acrylic acid modified is obtained by rosin.
4. preparation method according to claim 3, which is characterized in that the modified rosin is obtained by rosin through maleic acid modified It arrives, specially：
Rosin is crushed, when material temperature reaches 150-165 DEG C maleic acid is added, controlling reaction temperature is in 180- in heating melting 190 DEG C, reaction terminates to be cooled to room temperature, separation water outlet, dry, washing, after re-dry to obtain the final product.
5. preparation method according to claim 3, which is characterized in that the modified rosin is obtained by rosin through acrylic acid modified It arrives, specially：
Take rosin heating to 150-170 DEG C, acrylic acid added to react, wash after reaction to get.
6. preparation method according to claim 4, which is characterized in that
CH2OH(CH2)nNR2With maleic acid modified rosin acyl chloridesOccur esterification to getCompound of formula I.
7. preparation method according to claim 5, which is characterized in that
CH2OH(CH2)nNR2With acrylic acid modified rosin acyl chloridesEsterification occurs to get formula II compounds
8. application of the abietyl tertiary amine surfactant in antibacterial daily necessities described in claims 1 or 2.
CN201611199659.XA 2016-12-22 2016-12-22 A kind of abietyl tertiary amine class surfactant and its preparation method and application Expired - Fee Related CN106823984B (en)

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CN107629212B (en) * 2017-08-18 2020-06-26 北京林业大学 Rosinyl phosphate surfactant with pH response and application thereof
CN108782606B (en) * 2018-04-28 2020-11-06 北京林业大学 Rosin-based terpene-titanium dioxide hybrid nano material, preparation method and antibacterial application thereof
CN110607686B (en) * 2019-10-28 2022-07-15 迦南(福建)新材料科技有限公司 Antistatic treatment method for superfine fiber towel

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