CN106732165A - A kind of false Gemini surface active agent and its construction method in water situ acid-base neutralization - Google Patents
A kind of false Gemini surface active agent and its construction method in water situ acid-base neutralization Download PDFInfo
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Abstract
The invention provides a kind of "false" Gemini surface active agent and its construction method.Chain alkyl dimethyl tertiary amine, long-chain alkylamide propyl-dimethyl tertiary amine, long chain alkyl primary amine, one or more in chain alkyl ester group tertiary amine are included by the weak base of chain alkyl；Binary acid is included with Bola types weak diacid, one or more in aromatic dibasic acid, two parts raw material are constructed in acid-base neutralization mode in situ under agitation in water at 50~60 DEG C.Constructing for "false" Gemini surface active agent of the invention does not need complicated synthesis and purification process, and mild condition, temperature is low, and process is simple, it is not necessary to high-temperature high-pressure apparatus can online be constructed in use occasion, there is very much industrial prospect.
Description
Technical field
The present invention relates to colloid chemistry, particularly Surfactant Chemistry field, a kind of particularly "false" Shuangzi table
Face activating agent, and its in the construction method of water situ acid-base neutralization.
Background technology
Surfactant is while having hydrophilic, lipophilic group amphipathic compound, it is various in molecule
Industrial circle and daily life in have a wide range of applications.In its developing history, by chemical bond by two or two with
On same or almost same traditional single-stranded surfactant monomer, in its hydrophilic head base or near hydrophilic head base, use
Be linked together for this two parts to form a kind of new surfactant by spacer group, and it is referred to as the work of Shuangzi (Gemini) surface
Property agent, wherein with non-covalent bond couple Gemini surface active agent be also referred to as "false" Shuangzi (Psedogemini) surfactant.
But the mode of constructing of "false" Gemini surface active agent so far uses common single-stranded surfactant mostly
With the allotment of Bola types binary salt, such as Journal of Surfactants and Detergents, 2016,19 (2):237-
247；Langmuir,2013,29(13):4187-4192；The Journal of Physical Chemistry B,2012,
116(22):6425-6430；Soft Matter,2015,11(11):2080-2084；Journal ofSurfactants and
Detergents,2015,18(1):25-31 etc..Such maximum deficiency of mode of constructing is while having brought equimolar nothing into
Machine salt (NaCl, NaBr etc.), it is well known that these inorganic salts can to the surface-active of "false" Gemini surface active agent constructed and
Aggregate structure has opposite impacts on, and limits the application of constructed "false" Gemini surface active agent.
Therefore, Chinese patent 105435707A discloses one kind and counter ion coupled modes is utilized in the case of additive-free
The method for constructing the cationic Gemini surfactant with similar cloud point phenomenon.The present invention is in Chinese patent 105435707A
On the basis of further expand its practical range, use two parts raw material：The weak base of chain alkyl, such as alkyl dimethyl tertiary amide,
One or more in alkylamide propyl dimethyl tertiary amine, kiber alkyl amine, alkyl ester group tertiary amine；With Bola type weak diacids,
One or more such as binary acid, in aromatic dibasic acid；It is in molar ratio 2:1 ratio, under being stirred at 50~60 DEG C
"false" Gemini surface active agent is constructed in the way of acid-base neutralization in situ in water, due to neutralization reaction generation is water, will not
Bring inorganic salts into.Construction method of the invention does not need complicated synthesis and purification process, mild condition, process is simple, is not required to
High-temperature high-pressure apparatus is wanted, energy consumption is low, there is very much industrial prospect.
The content of the invention
It is an object of the invention to provide a kind of "false" Gemini surface active agent, another object is to provide one kind in water
The construction method of acid-base neutralization in situ.
A kind of "false" Gemini surface active agent of the invention be by the weak base containing chain alkyl and Bola types weak diacid by
Mol ratio is 2:1 ratio, under 50~60 DEG C of stirrings, is constructed in the way of water situ acid-base neutralization.
The weak base of described chain alkyl includes chain alkyl dimethyl tertiary amine, long-chain alkylamide propyl-dimethyl uncle
Amine, long chain alkyl primary amine, one or more in chain alkyl ester group tertiary amine；Wherein chain alkyl dimethyl tertiary amine mainly includes
Ten alkyl dimethyl tertiary amides, Dodecyl Dimethyl Amine, dodecyldimethylamine base tertiary amine, hexadecyldimethyl benzyl ammonium tertiary amine, ten
Eight alkyl dimethyl tertiary amides, eicosyl dimethyl tertiary amine, docosyl dimethyl tertiary amine, tetracosyl dimethyl uncle
Amine；Long-chain alkylamide propyl-dimethyl tertiary amine mainly includes ten alkylamide propyl dimethyl tertiary amines, laurylamide third
Base dimethyl tertiary amine, myristyl amide propyl-dimethyl tertiary amine, hexadecyl amide propyl-dimethyl tertiary amine, octadecyl acyl
Amine propyl-dimethyl tertiary amine, eicosyl amido propyl dimethyl tertiary amine, docosyl amido propyl dimethyl tertiary amine, 20
Tetraalkyl amido propyl dimethyl tertiary amine；Long chain alkyl primary amine mainly includes ten kiber alkyl amines, dodecyl primary amine, myristyl
Primary amine, cetyl primary amine, octadecyl primary amine, eicosyl primary amine, docosyl primary amine, tetracosyl primary amine；It is long
Alkyl group ester group tertiary amine mainly includes ten alkyl ester group ethyl dimethyl tertiary amines, dodecyl ester group ethyl dimethyl tertiary amine, ten
Tetraalkyl ester group ethyl dimethyl tertiary amine, cetyl ester group ethyl dimethyl tertiary amine, octadecyl ester group ethyl dimethyl uncle
Amine, eicosyl ester group ethyl dimethyl tertiary amine, docosyl ester group ethyl dimethyl tertiary amine, tetracosyl ester group ethyl
Dimethyl tertiary amine.
Described Bola types weak diacid includes binary acid, one or more in aromatic dibasic acid；It is wherein fatty
Binary acid refers mainly to C2~C15Alkyl or alkenyl binary acid, such as ethanedioic acid, malonic acid, succinic acid, glutaric acid, adipic acid, heptan two
Acid, suberic acid, azelaic acid, decanedioic acid, undecyl binary acid, dodecyl binary acid, tridecyl binary acid, myristyl
Binary acid, pentadecyl binary acid, maleic acid, fumaric acid, malic acid, tartaric acid, aspartic acid, glutamic acid etc.；It is wherein fragrant
Binary acid refers mainly to M-phthalic acid, terephthalic acid (TPA), phthalic acid, 2,6- naphthalenedicarboxylic acids, 1,4- naphthalenedicarboxylic acids, 4,4'-
Biphenyl dicarboxylic acid, 2,2'- biphenyl dicarboxylic acids, 2,6- pyridinedicarboxylic acids, 2,3- pyridinedicarboxylic acids (quinolinic acid) etc..
Specifically construction method is：
By the weak base of the Bola types weak diacid of certain mass, chain alkyl, (mol ratio with Bola type dicarboxylic acids is
2:1) it is separately added into a certain amount of ultra-pure water, is heated to 50~60 DEG C, maintain constant temperature more than 1 hour, completes to be similar in soda acid
And reaction, until insoluble matter is wholly absent, and untill obtaining the uniform, aqueous solution of clear, construct out certain in this way
The cationic "false" Gemini surface active agent transparent in appearance of concentration.
Uniform, clear the "false" Gemini surface active agent aqueous solution that will be obtained as stated above is at 80 DEG C of decompression
Rotary evaporation aqueous solvent therein, more than 12h is vacuum dried after obtaining solid sample under the conditions of 80 DEG C, that is, obtain "false" Shuangzi
The solid product of surfactant.
The cationic Gemini surfactant being connected with traditional single-stranded cationic surfactant, with covalent bond is not
Together, constructing for cationic "false" Gemini surface active agent of the invention does not need complicated synthesis and purification process, condition temperature
With temperature is low, process is simple, it is not necessary to high-temperature high-pressure apparatus, can online be constructed according to the demand of application scenario, there is very much work
Industry prospect.
Specific embodiment
The present invention is illustrated by the following examples, but the present invention do not limited by these.
Embodiment 1
0.005 mole of malonic acid is added in the 250mL reactors equipped with 100mL deionized waters, is added under agitation
Hot to 50 DEG C make it is added dropwise over 0.01 mole again Dodecyl Dimethyl Amine after dissolving, and stirring is lower to maintain constant temperature 1 hour,
Solutions display is fully transparent in appearance, illustrates that similar acid-base neutralization reaction is gradually completed, thus with soda acid in situ
The mode of sum constructs out the "false" Gemini surface active agent that concentration is 0.05mol/L.Decompression 80 DEG C at rotary evaporation it is therein
Aqueous solvent (notes a large amount of foams for producing, prevent slug), then remaining solid content is vacuum dried under the conditions of 80 DEG C 12h with
On, that is, obtain the solid product (referred to as 12-3-12) of "false" Gemini surface active agent.
Embodiment 2
With reference to construction method and step in embodiment 1, the difference is that 0.001 mole of terephthalic acid (TPA) is added to and is equipped with
In the 250mL reactors of 100mL deionized waters, it is heated to after 55 DEG C being added dropwise over 0.002 mole of the tetradecane again under agitation
Base amido propyl dimethyl tertiary amine, 55 DEG C of maintenance constant temperature 1 hour, solutions display is fully transparent in appearance, illustrates class acidoid
Alkali neutralization reaction is gradually completed, thus constructs out "false" Shuangzi of the concentration as 0.01mol/L in acid-base neutralization mode in situ
Surfactant.Decompression 80 DEG C at rotary evaporation aqueous solvent therein (note produce a large amount of foams, prevent slug), then will
Remaining solid content is vacuum dried more than 12h under the conditions of 80 DEG C, that is, obtain the solid product (letter of "false" Gemini surface active agent
Referred to as 14A-PTA-14A).
Embodiment 3
"false" the Gemini surface active agent 12-3-12 and 14A- that will be obtained according to the method in embodiment 1 and embodiment 2
It is 1 × 10 that PTA-14A is configured to concentration respectively-4mol/L、2×10-4mol/L、3×10-4mol/L、4×10-4mol/L、5×
10-4mol/L、6×10-4mol/L、7×10-4mol/L、8×10-4mol/L、9×10-4mol/L、1×10-3mol/L、4×10- 3mol/L、6×10-3mol/L、8×10-3The solution of mol/L, determines embodiment 1 and embodiment 2 respectively at 30 DEG C with sessile drop method
In the method surface tension and critical micelle concentration of "false" Gemini surface active agent 12-3-12 and 14A-PTA-14A that obtain.
The critical micelle concentration of 12-3-12 is 3.6 × 10-3Mol/L, lowest surface tension 30.3mN/m；The critical glue of 14A-PTA-14A
Beam concentration is 5.7 × 10-4Mol/L, lowest surface tension 29.6mN/m, are below the traditional single-stranded surfactant similar to its
DTAB (cmc=1.6 × 10-2Mol/L, 25 DEG C).
It can be seen that, by the non-surface active weak base containing chain alkyl and Bola types weak diacid in water situ acid-base neutralization
The mode 12-3-12 that constructs and 14A-PTA-14A show the surface-active of surfactant, and with Gemini effect.
Claims (4)
1. a kind of "false" Gemini surface active agent and its construction method, it is characterised in that by the weak base containing chain alkyl and Bola types
Weak diacid two parts raw material are constructed.
2. the weak base of chain alkyl as claimed in claim 1 includes chain alkyl dimethyl tertiary amine, long-chain alkylamide propyl group
Dimethyl tertiary amine, long chain alkyl primary amine, one or more in chain alkyl ester group tertiary amine.Mainly include C10~C24Alkyl two
Methyl tertiary amine；C10~C24Long-chain alkylamide propyl-dimethyl tertiary amine；C10~C24Kiber alkyl amine；C10~C24Alkyl ester group ethyl
Dimethyl tertiary amine.
3. Bola types weak diacid as claimed in claim 1 includes one or more in binary acid, refers mainly to C2~
C15Alkyl or alkenyl binary acid, such as ethanedioic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid,
Decanedioic acid, undecyl binary acid, dodecyl binary acid, tridecyl binary acid, myristyl binary acid, pentadecyl two
First acid, maleic acid, fumaric acid, malic acid, tartaric acid, aspartic acid, glutamic acid etc.；With one kind in aromatic dibasic acid or several
Kind, refer mainly to M-phthalic acid, terephthalic acid (TPA), phthalic acid, NDA, Isosorbide-5-Nitrae-naphthalenedicarboxylic acid, 4,4'- biphenyl
Dioctyl phthalate, 2,2'- biphenyl dicarboxylic acids, 2,6- pyridinedicarboxylic acids, 2,3- pyridinedicarboxylic acids (quinolinic acid) etc..
4. the weak base containing chain alkyl used by "false" Gemini surface active agent as claimed in claim 1 is weak with Bola type binary
The mol ratio of acid is 2:1, under being stirred at 50~60 DEG C, constructed in the way of water situ acid-base neutralization.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109985565A (en) * | 2017-12-29 | 2019-07-09 | 中国石油化工股份有限公司 | The mixed system and preparation method thereof of fatty acid type surfactant |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102851019A (en) * | 2012-10-15 | 2013-01-02 | 成都理工大学 | Preparation method of cationic viscoelastic surfactant fracturing fluid |
| CN105435707A (en) * | 2015-12-16 | 2016-03-30 | 江南大学 | Cationic gemini surfactant with analogue cloud temperature phenomenon, and construction method thereof |
| CN105964185A (en) * | 2016-05-24 | 2016-09-28 | 江南大学 | Asymmetric cationic Gemini surfactant containing hydroxyl group in coupling link |
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2016
- 2016-11-30 CN CN201611078479.6A patent/CN106732165A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102851019A (en) * | 2012-10-15 | 2013-01-02 | 成都理工大学 | Preparation method of cationic viscoelastic surfactant fracturing fluid |
| CN105435707A (en) * | 2015-12-16 | 2016-03-30 | 江南大学 | Cationic gemini surfactant with analogue cloud temperature phenomenon, and construction method thereof |
| CN105964185A (en) * | 2016-05-24 | 2016-09-28 | 江南大学 | Asymmetric cationic Gemini surfactant containing hydroxyl group in coupling link |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109985565A (en) * | 2017-12-29 | 2019-07-09 | 中国石油化工股份有限公司 | The mixed system and preparation method thereof of fatty acid type surfactant |
| CN109985565B (en) * | 2017-12-29 | 2021-07-02 | 中国石油化工股份有限公司 | Mixed system containing fatty acid type surfactant and preparation method thereof |
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Application publication date: 20170531 |