CN107551952A - Carboxylic acid type plant oil base gemini surfactant and preparation method thereof - Google Patents
Carboxylic acid type plant oil base gemini surfactant and preparation method thereof Download PDFInfo
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- CN107551952A CN107551952A CN201710838141.4A CN201710838141A CN107551952A CN 107551952 A CN107551952 A CN 107551952A CN 201710838141 A CN201710838141 A CN 201710838141A CN 107551952 A CN107551952 A CN 107551952A
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Abstract
The present invention relates to a kind of carboxylic acid type plant oil base gemini surfactant and preparation method thereof, prepared by following steps：A. polyunsaturated vegetable oil acid is subjected to sulfydryl alkene click-reaction with double sulfhydryl compounds and obtains sulfhydryl modified vegetable oil acid, sulfhydryl modified vegetable oil acid and salt-forming reagent are carried out reaction and obtain described carboxylic acid type plant oil base gemini surfactant by b..Ground surfactant activity of the present invention is good, and critical micelle concentration is low, is used for emulsion polymerised products as emulsifying agent, hence it is evident that improve the Calcium ion stability of product, reduce emulsion particle diameter.Body material used in product of the present invention, it is environment friendly and pollution-free, preparation process mild condition, use method green, post processing is simple, and product is easy to purify.
Description
[technical field]
The present invention relates to a kind of carboxylic acid type plant oil base gemini surfactant and preparation method thereof.
[background technology]
Contain two or more hydrophilic radicals and hydrophobic grouping in gemini surfactant, with traditional surface
Activating agent is compared, and has at a fairly low CMC value, and its ionic group carries double charge, is caused in emulsion polymerization process in aqueous phase
Emulsion particle it is more stable, be more suitable for being used as emulsifying agent, simultaneously as his special chemical structure, makes it easier in liquid
Arranged closely on liquid/solid interface, reach excellent wetting effect.
At the same time, with the increasingly depleted of petroleum resources, international oil price is constantly soaring, seeks renewable raw materials to prepare
New coating is into inexorable trend.Vegetable oil source is extensive, low processing cost, and raw material is environmentally friendly and product is degradable, and belonging to can
Regenerated resources, and receive the favor of numerous researchers containing largely may modify functional group in structure.
[content of the invention]
Ground of the invention purpose is to provide a kind of carboxylic acid type plant oil base double type table prepared by vegetable oil
Face activating agent.
To achieve these goals, there is provided a kind of carboxylic acid type plant oil base gemini surfactant, by following steps
Prepare：
A. polyunsaturated vegetable oil acid is subjected to sulfydryl-alkene click-reaction with double sulfhydryl compounds and obtains sulfhydryl modified plant
Oleic acid,
B. sulfhydryl modified vegetable oil acid and salt-forming reagent are subjected to reaction and obtain described carboxylic acid type plant oil base pair
Subtype surfactant.
Above-mentioned preparation method also has following optimize technique：
Described sulfydryl-alkene click-reaction is by polyunsaturated vegetable oil acid, dimercaptan, light trigger and dichloromethane
Alkane is added in reaction bulb, is stirred at room temperature under state, and after 1.8mw/cm2 ultra violet lamps 2~16 hours, revolving removes two
Chloromethanes obtains sulfhydryl modified vegetable oil acid, and the mol ratio content of wherein dimercaptan and polyunsaturated vegetable oil acid is 1:
2。
Described sulfhydryl modified vegetable oil acid mixes the progress neutralization reaction of 0.5-1 hours, regulation with salt-forming reagent
PH to 8-9 is to obtain described carboxylic acid type plant oil base gemini surfactant.
Described polyunsaturated vegetable oil acid includes undecenoic acid, oleic acid, linoleic acid, leukotrienes, petroselic acid, sinapic acid, and ten
Eight carbon trienic acids, one or more kinds of mixtures in castor oil acid.
Described double sulfhydryl compounds include dithioglycol, dimercaptopropane, succinimide mercaptans, ethanthiol, in pungent two mercaptan
One or more kinds of mixtures.
Described salt-forming reagent includes potassium hydroxide, sodium hydroxide, one or more kinds of mixtures in ammoniacal liquor.
Ground surfactant activity of the present invention is good, and critical micelle concentration is low, is used for emulsion polymerised products as emulsifying agent, bright
The aobvious Calcium ion stability for improving product, reduces emulsion particle diameter.Body material used in product of the present invention, environmental protection is without dirt
Dye, preparation process mild condition, uses method green, and post processing is simple, and product is easy to purify.
[brief description of the drawings]
Fig. 1 is the syntheti c route figure of undecenoic acid based surfactants；
Fig. 2 is the syntheti c route figure of castor oil acid based surfactants；
The syntheti c route figure of Fig. 3 oleic acid based surfactants.
[embodiment]
Hereinafter, it is described further in conjunction with the embodiments with accompanying drawing for the present invention, it will be appreciated that embodiment and accompanying drawing are only used
In explanation rather than limit protection scope of the present invention.
By the use of reproducible polyunsaturated vegetable oil acid as initiation material, double type table is synthesized by sulfydryl-alkene clicking chemistry
Face activating agent, and it is steady in particle diameter and calcium ion with the emulsion prepared by conventional emulsifier by emulsion polymerization way to compared for it
Qualitatively difference, the results showed that, emulsion prepared by double type emulsifying agent, particle diameter is smaller, and Calcium ion stability is more excellent.
The surfactant has following structural formula：
Wherein X is Na+, K+, NH4 +In one kind, n is the carbon chain lengths in double sulfhydryl compounds, and m is polyunsaturated vegetable oil
The carbon chain lengths of acid.It is described further by the following examples for the present invention.
Embodiment 1
Respectively by undecenoic acid 0.1mol, dithioglycol 0.05mol, light trigger (UV1173) 0.01g and dichloromethane
Alkane 20ml is added in reaction bulb, is stirred at room temperature under state, is used 1.8mw/cm2Ultra violet lamp 2 hours, it is ensured that unsaturation is planted
Unsaturated double-bond on thing oleic acid reacts with dimercaptan, and revolving removes dichloromethane and obtains sulfhydryl modified endecatylene
Acid.
Obtained sulfhydryl modified vegetable oil acid and 50% sodium hydrate aqueous solution are mixed into the progress of 0.5-1 hours
Neutralization reaction, regulation pH to 8-9 obtain a kind of carboxylic acid type plant oil base gemini surfactant.
Synthesis step is as shown in Figure 1.
Embodiment 2
Respectively by castor oil acid 0.1mol, succinimide mercaptans 0.05mol, light trigger (UV1173) 0.01g and dichloromethane
20ml is added in reaction bulb, is stirred at room temperature under state, is used 1.8mw/cm2Ultra violet lamp 4 hours, it is ensured that unsaturated plant
Unsaturated double-bond on oleic acid reacts with dimercaptan, and revolving removes dichloromethane and obtains sulfhydryl modified castor oil acid.
Obtained sulfhydryl modified vegetable oil acid and potassium hydroxide aqueous solution mixing 0.5-1 hours neutralize instead
Should, regulation pH to 8-9 obtains a kind of carboxylic acid type plant oil base gemini surfactant.
Synthesis step is as shown in Figure 2.
Embodiment 3
Respectively by oleic acid 0.1mol, ethanthiol 0.05mol, light trigger (UV1173) 0.01g and dichloromethane 20ml
Add in reaction bulb, be stirred at room temperature under state, use 1.8mw/cm2Ultra violet lamp 12 hours, it is ensured that polyunsaturated vegetable oil
Unsaturated double-bond on acid reacts with dimercaptan, and revolving removes dichloromethane and obtains sulfhydryl modified castor oil acid.
Obtained sulfhydryl modified vegetable oil acid and industrial ammonia are mixed into the progress neutralization reaction of 0.5-1 hours, adjusted
Section pH to 8-9 obtains a kind of carboxylic acid type plant oil base gemini surfactant.
Synthesis step is as shown in Figure 3.
Embodiment 4
It is 50% that surfactant prepared by embodiment 1-3 is diluted with water into solid part, carries out emulsion polymerization, institute
It is as follows with being formulated：
Emulsion is prepared by following steps：
The preparation of pre-emulsion：Monomer, surfactant, pure water (70g, emulsified monomer), initiator are sequentially added into 4 mouthfuls of burnings
In bottle, high-speed stirred 30 minutes, pre-emulsion is prepared.
Remaining 83g pure water is added in 4 mouthfuls of flasks, opens stirring, is warming up to 80 DEG C, adds 5% pre-emulsion, insulation 20
Minute.
After insulation terminates, remaining pre-emulsion is at the uniform velocity added dropwise in 4 mouthfuls of flasks, 3h is added dropwise, after being added dropwise, 80 DEG C
Insulation 1 hour, is cooled to 45 DEG C, adds ammoniacal liquor and is neutralized, and regulation pH is between 7-8, filtering and discharging.
4 synthesized emulsions have been carried out with particle diameter and Calcium ion stability contrast：
Thus carboxylic acid type plant oil base gemini surfactant produced by the present invention, there is relatively low CMC value, made
The features such as standby emulsion particle diameter is small, and Calcium ion stability is excellent.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and
Within principle, any modification, equivalent substitution and improvements made etc., it should be included in the scope of the protection.
Claims (7)
1. a kind of preparation method of carboxylic acid type plant oil base gemini surfactant, it is characterised in that prepared by following steps
Obtain：
A. polyunsaturated vegetable oil acid is subjected to sulfydryl-alkene click-reaction with double sulfhydryl compounds and obtains sulfhydryl modified vegetable oil
Acid,
B. sulfhydryl modified vegetable oil acid and salt-forming reagent are subjected to reaction and obtain described carboxylic acid type plant oil base double type
Surfactant.
2. the preparation method of carboxylic acid type plant oil base gemini surfactant as claimed in claim 1, it is characterised in that
Described sulfydryl-alkene click-reaction is to add polyunsaturated vegetable oil acid, dimercaptan, light trigger and dichloromethane instead
Answer in bottle, be stirred at room temperature under state, use 1.8mw/cm2After ultra violet lamp 2~16 hours, revolving removes dichloromethane and obtained
To sulfhydryl modified vegetable oil acid, the mol ratio content of wherein dimercaptan and polyunsaturated vegetable oil acid is 1:2.
3. the preparation method of carboxylic acid type plant oil base gemini surfactant as claimed in claim 1, it is characterised in that
Described sulfhydryl modified vegetable oil acid mixes the progress neutralization reaction of 0.5-1 hours with salt-forming reagent, and regulation pH to 8-9 is
Obtain described carboxylic acid type plant oil base gemini surfactant.
4. the preparation method of carboxylic acid type plant oil base gemini surfactant as claimed in claim 1, it is characterised in that
Described polyunsaturated vegetable oil acid includes undecenoic acid, oleic acid, linoleic acid, leukotrienes, petroselic acid, sinapic acid, 18 carbon triolefins
Acid, one or more kinds of mixtures in castor oil acid.
5. the preparation method of carboxylic acid type plant oil base gemini surfactant as claimed in claim 1, it is characterised in that
Described double sulfhydryl compounds include dithioglycol, dimercaptopropane, succinimide mercaptans, ethanthiol, one kind in pungent two mercaptan or
More than one mixtures.
6. the preparation method of carboxylic acid type plant oil base gemini surfactant as claimed in claim 1, it is characterised in that
Described salt-forming reagent includes potassium hydroxide, sodium hydroxide, one or more kinds of mixtures in ammoniacal liquor.
A kind of 7. hydrochlorate type plant oil base double type prepared using any claim preparation method of claim 1~6
Surfactant.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112724338A (en) * | 2020-12-24 | 2021-04-30 | 浩力森涂料（上海）有限公司 | Castor oil modified emulsion for improving directionality of silver powder of water-based silver powder coating and preparation method of castor oil modified emulsion |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103865511A (en) * | 2012-12-11 | 2014-06-18 | 中国石油天然气股份有限公司 | Viscoelastic surfactant fracturing fluid and preparation method and application thereof |
| CN104877123A (en) * | 2015-06-08 | 2015-09-02 | 江西科技师范大学 | Method for preparing plant oil-based cyclic carbonate prepolymer through thiol-ene click reaction |
| US9394386B1 (en) * | 2015-01-30 | 2016-07-19 | Wisconsin Alumni Research Foundation | Polymerizable mixtures containing ionic gemini surfactants; and lyotropic liquid crystals, polymers, and membranes made therefrom |
| CN106540630A (en) * | 2016-10-18 | 2017-03-29 | 江南大学 | A kind of carboxylic acid type anionic Gemini surfactant and preparation method thereof |
-
2017
- 2017-09-15 CN CN201710838141.4A patent/CN107551952B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103865511A (en) * | 2012-12-11 | 2014-06-18 | 中国石油天然气股份有限公司 | Viscoelastic surfactant fracturing fluid and preparation method and application thereof |
| US9394386B1 (en) * | 2015-01-30 | 2016-07-19 | Wisconsin Alumni Research Foundation | Polymerizable mixtures containing ionic gemini surfactants; and lyotropic liquid crystals, polymers, and membranes made therefrom |
| CN104877123A (en) * | 2015-06-08 | 2015-09-02 | 江西科技师范大学 | Method for preparing plant oil-based cyclic carbonate prepolymer through thiol-ene click reaction |
| CN106540630A (en) * | 2016-10-18 | 2017-03-29 | 江南大学 | A kind of carboxylic acid type anionic Gemini surfactant and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 刘清等: "巯基-烯/炔点击化学研究进展", 《有机化学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112724338A (en) * | 2020-12-24 | 2021-04-30 | 浩力森涂料（上海）有限公司 | Castor oil modified emulsion for improving directionality of silver powder of water-based silver powder coating and preparation method of castor oil modified emulsion |
| CN112724338B (en) * | 2020-12-24 | 2022-08-12 | 浩力森涂料（上海）有限公司 | Castor oil modified emulsion for improving directionality of silver powder of water-based silver powder coating and preparation method of castor oil modified emulsion |
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Application publication date: 20180109 Assignee: Cangyao Technology (Jiangsu) Co.,Ltd. Assignor: HLS COATING (SHANGHAI) Co.,Ltd. Contract record no.: X2021310000052 Denomination of invention: Carboxylate vegetable oil based Gemini surfactant and its preparation method Granted publication date: 20191122 License type: Common License Record date: 20211227 |
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