CN106188573A - PH response emulsion that a kind of star-type polymer is stable and preparation method and application - Google Patents
PH response emulsion that a kind of star-type polymer is stable and preparation method and application Download PDFInfo
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- CN106188573A CN106188573A CN201610640908.8A CN201610640908A CN106188573A CN 106188573 A CN106188573 A CN 106188573A CN 201610640908 A CN201610640908 A CN 201610640908A CN 106188573 A CN106188573 A CN 106188573A
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Abstract
The invention belongs to Polymer Synthesizing and emulsion technology field, disclose the stable pH response emulsion of a kind of star-type polymer and preparation method and application.This preparation method as emulsifying agent, is stablized aqueous phase and oil phase by star-type polymer, forms O/w emulsion;Described star polymer be prestox acryloxypropyl cage-type silsesquioxane be kernel polymethylacrylic acid dimethylaminoethyl be the star-type polymer of arm, its structural formula is as follows:
Description
Technical field
The invention belongs to Polymer Synthesizing and emulsion technology field, particularly to the pH response that a kind of star-type polymer is stable
Property emulsion and preparation method and application.
Background technology
In recent years, the polymer of various non-linearity structures is (as common in star-type polymer, star amphiphilic copolymer, star type block
Polymers, tree-shaped or dissaving polymer etc.) due to its special structure and character, draw in theoretical research and actual application aspect
Play the broad interest of people.Wherein star-type polymer designs simple, textures, unique properties, has potential application prospect, is subject to
Pay close attention to scientific circles and industrial quarters.Its important feature is the linear polymerization than same molecular amount of its body and solution viscosity
Thing is much lower, so being widely used as rheology control agent in coating, contact adhesive and thermoplastic elastomer (TPE) etc..Additionally,
It can be also used for solubilizing agent, impact resistance dressing agent, sealant and molding component etc. are blended.Therefore, star-type polymer is studied
Synthesis has important theoretical and practical significance.
Stimulating responsive polymer refers to when environment or external condition change, and self can occur physically or chemically to become
The base polymer changed.This base polymer, because the performance of its uniqueness, causes the very big concern of researcher.Poly-methyl-prop
Existing hydrophobic alkyl backbones in the chemical constitution of olefin(e) acid dimethylaminoethyl, possibly together with the amino side chain of hydrophilic group, and
On space structure, amino is fine with alkyl group matching, is the amphipathic nature polyalcohol with pH sensitivity.Amphipathic imparting
Polymethylacrylic acid dimethylaminoethyl makes the possibility of emulsion-stabilizing as emulsifying agent, and pH sensitivity can be then that emulsion is brought newly
Characteristic.Line style polymethylacrylic acid dimethylaminoethyl uses as emulsifying agent, in fact it could happen that easily reunite, and emulsifying power is low
Shortcoming, the use of the most novel star-type polymer based on polymethylacrylic acid dimethylaminoethyl then becomes inevitable.
Summary of the invention
In order to overcome the shortcoming of above-mentioned prior art with not enough, the primary and foremost purpose of the present invention is to provide a kind of star polymerization
The preparation method of the pH response emulsion that thing is stable.
Preparation method of the present invention, to have the star-type polymer of pH response as emulsifying agent, instead of traditional organic emulsifying
The use of agent, it is thus achieved that stable emulsion, the emulsion simultaneously prepared has pH response.
The pH response emulsion that star-type polymer that another object of the present invention is to provide a kind of said method to prepare is stable.
Still a further object of the present invention is the application of the pH response emulsion providing above-mentioned star-type polymer stable.
The purpose of the present invention is realized by following proposal:
The preparation method of the pH response emulsion that a kind of star-type polymer is stable, by star-type polymer as emulsifying agent, surely
Determine aqueous phase and oil phase, form O/w emulsion.
Described star polymer be prestox acryloxypropyl cage-type silsesquioxane be kernel polymethylacrylic acid
Dimethylaminoethyl is the star-type polymer (CMSQ-PDMAEMA) of arm, and its structural formula is as follows:
Wherein in an embodiment, described oil phase fingernail benzene, dimethylbenzene or liquid paraffin.
Wherein in an embodiment, the amount of CMSQ-PDMAEMA used is the 1~2% of emulsion system gross mass.
Wherein in an embodiment, the amount of CMSQ-PDMAEMA used is the 1.5% of emulsion system gross mass.
In preparation method of the present invention, CMSQ-PDMAEMA, as emulsifying agent, plays the effect substituting conventional emulsifier, when it
Consumption is too high, then be easily generated gel in emulsion process;Consumption is too low, then emulsifying effectiveness is inconspicuous.
Wherein in an embodiment, the pH of described reaction system is between 7~9.
Wherein in an embodiment, the consumption of described aqueous phase is the 50~70% of reaction system gross mass.
Wherein in an embodiment, the consumption of described aqueous phase is the 60% of reaction system gross mass.
Wherein in an embodiment, the condition of described reaction is at room temperature to carry out.
Above-mentioned preparation method specifically includes following steps: as emulsifying agent, star-type polymer is put into the mixed of aqueous phase and oil phase
In fit system, emulsifying, form O/w emulsion.
Wherein in an embodiment, described emulsifying refer to use high speed dispersor stirring carry out, rotating speed be 3000~
5000r/min。
Wherein in an embodiment, described emulsifying refers to use high speed dispersor stirring to carry out, and rotating speed is 4000r/min.
Wherein in an embodiment, described mixing time is 2~4min.
Wherein in an embodiment, described mixing time is 3min.
The pH response emulsion that a kind of star-type polymer is stable, is obtained by above-mentioned preparation method.Wherein, the breast of the present invention
Star-type polymer described in liquid is with prestox acryloxypropyl cage-type silsesquioxane as kernel, and this star-type polymer has
PH stimulating responsive, when extraneous pH value is alkalescence, then polymethylacrylic acid dimethylaminoethyl segment is contraction state, emulsifying
Effect reduction even results in breakdown of emulsion.Preparation method process is simple, easy.Additionally, this star-type polymer also has Thermo-sensitive, can be in temperature
Degree realizes the change that polymer chain stretches and shrinks when changing.These characteristics make the emulsion utilizing this polymer to prepare can
For multiple fields such as drug release based on stimulating responsive polymer, hydrogels.
The mechanism of the present invention is:
The present invention utilizes CMSQ-PDMAEMA to substitute oil phase and the aqueous phase such as conventional emulsifier and toluene, dimethylbenzene or paraffin oil
Common emulsifying obtains the emulsion with pH response, when emulsion pH > 13 time, emulsion breaking, when pH is adjusted to 7~9, i.e. recover to
Homogeneous, stable emulsion.CMSQ-PDMAEMA has star-like molecular structure, and wherein CMSQ is organic-inorganic nano hydridization knot
Structure, the good hot property being had, mechanical performance etc. are incorporated in emulsion, can be effectively improved thermostability and the stretching of emulsion
Etc. performance, it is greatly expanded the range of application of Pickering emulsion.
The present invention, relative to prior art, has such advantages as and beneficial effect:
(1) reported first of the present invention is by the CMSQ-with prestox acryloxypropyl cage-type silsesquioxane as kernel
PDMAEMA star-type polymer is applied in emulsion preparation, has filled up the deficiency in existing research range.
(2) emulsion prepared by the present invention has pH response, i.e. when system pH changes, can make emulsion breaking, adjusts
Joint pH can make emulsion recover.
(3) operating procedure of the present invention is relatively simple, and experiment condition is gentle, and selected raw material, reagent is the most all easier
Obtaining, the productivity of reaction is high.
Accompanying drawing explanation
Fig. 1 is the emulsion for preparing of embodiment 1 and breakdown of emulsion and the picture of recovery, and wherein a, b, c are respectively emulsion, breakdown of emulsion
And recovery.
Fig. 2 is particle diameter and the Zeta potential figure of the emulsion that embodiment 1 prepares.
Detailed description of the invention
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention do not limit
In this.
Described CMSQ-PDMAEMA refers to prestox acryloxypropyl cage-type silsesquioxane for the poly-methyl-prop of kernel
Olefin(e) acid dimethylaminoethyl is the star-type polymer of arm, and preparation method sees CN104861098A, the most superfluous in following example
State.
Embodiment 1
Weigh 1g CMSQ-PDMAEMA, be dissolved in 20g toluene, add 80g water, with appropriate concentrated hydrochloric acid regulation pH be
7, mix homogeneously is placed in dispersion machine and carries out emulsifying, rotating speed 4000r/min.Stop after 3 minutes, obtain homogeneous, stable white
Color emulsion.Emulsion obtained above being placed in centrifuge tube, turning speed is 3000rpm, observes, be still homogeneous after centrifugal 30min
Stable emulsion, without sedimentation and lamination.
Emulsion appearance obtained above is as it is shown in figure 1, picture display emulsion is uniform.Fig. 2 is that this emulsion is through DLS and Zeta electricity
Gained particle diameter and Zeta potential size after bit test.As shown in Figure 2, emulsion particle diameter is 5.57 μm, and emulsion particle diameter is homogeneous, many points
Dissipating property good, Zeta potential is-30.2mV, and display emulsion has good stability.
Embodiment 2
Weigh 1g CMSQ-PDMAEMA, be dissolved in 20g toluene, add 80g water, with appropriate concentrated hydrochloric acid regulation pH be
8, mix homogeneously is placed in dispersion machine and carries out emulsifying, rotating speed 3000r/min.Stop after 4 minutes, obtain homogeneous, stable white
Color emulsion.Emulsion obtained above being placed in centrifuge tube, turning speed is 3000rpm, observes, be still homogeneous after centrifugal 30min
Stable emulsion, without sedimentation and lamination.
The emulsion appearance that this step obtains is similar with gained emulsion in embodiment 1, particle diameter and Zeta potential result display breast
Liquid uniform particle diameter, and good stability.
Embodiment 3
Weigh 1g CMSQ-PDMAEMA, be dissolved in 20g dimethylbenzene, add 80g water, with appropriate sodium hydroxide solution
Regulation pH is 9, and mix homogeneously is placed in dispersion machine and carries out emulsifying, rotating speed 5000r/min.After 2 minutes stop, obtaining homogeneous,
Stable white emulsion.Emulsion obtained above being placed in centrifuge tube, turning speed is 3000rpm, observes after centrifugal 30min,
It is still the emulsion of stable homogeneous, without sedimentation and lamination.
The emulsion appearance that this step obtains is similar with gained emulsion in embodiment 1, particle diameter and Zeta potential result display breast
Liquid uniform particle diameter, and good stability.
Embodiment 4
Weigh 1.5g CMSQ-PDMAEMA, be dissolved in 20g dimethylbenzene, add 80g water, with appropriate concentrated hydrochloric acid regulation
PH is 7, and mix homogeneously is placed in dispersion machine and carries out emulsifying, rotating speed 3000r/min.Stop after 3 minutes, obtain homogeneous, stable
White emulsion.Emulsion obtained above being placed in centrifuge tube, turning speed is 3000rpm, observes, be still after centrifugal 30min
The emulsion of stable homogeneous, without sedimentation and lamination.
The emulsion appearance that this step obtains is similar with gained emulsion in embodiment 1, particle diameter and Zeta potential result display breast
Liquid uniform particle diameter, and good stability.
Embodiment 5
Weigh 1.5g CMSQ-PDMAEMA, be dissolved in 20g dimethylbenzene, add 80g water, with appropriate concentrated hydrochloric acid regulation
PH is 8, and mix homogeneously is placed in dispersion machine and carries out emulsifying, rotating speed 4000r/min.Stop after 3 minutes, obtain homogeneous, stable
White emulsion.Emulsion obtained above being placed in centrifuge tube, turning speed is 3000rpm, observes, be still after centrifugal 30min
The emulsion of stable homogeneous, without sedimentation and lamination.
The emulsion appearance that this step obtains is similar with gained emulsion in embodiment 1, particle diameter and Zeta potential result display breast
Liquid uniform particle diameter, and good stability.
Embodiment 6
Weigh 1.5g CMSQ-PDMAEMA, be dissolved in 20g liquid paraffin, add 80g water, with appropriate sodium hydroxide
Solution regulation pH is 9, and mix homogeneously is placed in dispersion machine and carries out emulsifying, rotating speed 5000r/min.Stop after 2 minutes, obtain all
One, stable white emulsion.Emulsion obtained above being placed in centrifuge tube, turning speed is 3000rpm, sees after centrifugal 30min
Examine, be still the emulsion of stable homogeneous, without sedimentation and lamination.
The emulsion appearance that this step obtains is similar with gained emulsion in embodiment 1, particle diameter and Zeta potential result display breast
Liquid uniform particle diameter, and good stability.
Embodiment 7
Weigh 2g CMSQ-PDMAEMA, be dissolved in 20g liquid paraffin, add 80g water, molten with appropriate sodium hydroxide
Liquid regulation pH is 9, and mix homogeneously is placed in dispersion machine and carries out emulsifying, rotating speed 5000r/min.Stop after 3 minutes, obtain all
One, stable white emulsion.Emulsion obtained above being placed in centrifuge tube, turning speed is 3000rpm, sees after centrifugal 30min
Examine, be still the emulsion of stable homogeneous, without sedimentation and lamination.
The emulsion appearance that this step obtains is similar with gained emulsion in embodiment 1, particle diameter and Zeta potential result display breast
Liquid uniform particle diameter, and good stability.
Embodiment 8
Weigh 2g CMSQ-PDMAEMA, be dissolved in 20g liquid paraffin, add 80g water, with appropriate concentrated hydrochloric acid regulation
PH is 7, and mix homogeneously is placed in dispersion machine and carries out emulsifying, rotating speed 3000r/min.Stop after 4 minutes, obtain homogeneous, stable
White emulsion.Emulsion obtained above being placed in centrifuge tube, turning speed is 3000rpm, observes, be still after centrifugal 30min
The emulsion of stable homogeneous, without sedimentation and lamination.
The emulsion appearance that this step obtains is similar with gained emulsion in embodiment 1, particle diameter and Zeta potential result display breast
Liquid uniform particle diameter, and good stability.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention are not by above-described embodiment
Limit, the change made under other any spirit without departing from the present invention and principle, modify, substitute, combine, simplify,
All should be the substitute mode of equivalence, within being included in protection scope of the present invention.
Claims (10)
1. the preparation method of the pH response emulsion that a star-type polymer is stable, it is characterised in that by star-type polymer as breast
Agent, stablizes aqueous phase and oil phase, forms O/w emulsion;
Described star polymer be prestox acryloxypropyl cage-type silsesquioxane be kernel polymethylacrylic acid diformazan
Amino ethyl ester is the star-type polymer of arm, and its structural formula is as follows:
The preparation method of the pH response emulsion that star-type polymer the most according to claim 1 is stable, it is characterised in that: institute
Oil phase fingernail benzene, dimethylbenzene or the liquid paraffin stated.
The preparation method of the pH response emulsion that star-type polymer the most according to claim 1 is stable, it is characterised in that: institute
With 1~2% that the amount of star-type polymer is emulsion system gross mass;The consumption of described aqueous phase be reaction system gross mass 50~
70%.
The preparation method of the pH response emulsion that star-type polymer the most according to claim 1 is stable, it is characterised in that: institute
With 1.5% that the amount of star-type polymer is emulsion system gross mass;The consumption of described aqueous phase is the 60% of reaction system gross mass.
The preparation method of the pH response emulsion that star-type polymer the most according to claim 1 is stable, it is characterised in that: institute
State the pH of reaction system between 7~9.
The preparation method of the pH response emulsion that star-type polymer the most according to claim 1 is stable, it is characterised in that tool
Body comprises the following steps: put into by star-type polymer in the mixed system of aqueous phase and oil phase as emulsifying agent, and emulsifying forms water bag
Fat liquor.
The preparation method of the pH response emulsion that star-type polymer the most according to claim 6 is stable, it is characterised in that: institute
Stating emulsifying to refer to use high speed dispersor stirring to carry out, rotating speed is 3000~5000r/min;Described mixing time is 2~4min.
The preparation method of the pH response emulsion that star-type polymer the most according to claim 6 is stable, it is characterised in that: institute
Stating emulsifying to refer to use high speed dispersor stirring to carry out, rotating speed is 4000r/min;Described mixing time is 3min.
9. the pH response emulsion that a star-type polymer is stable, it is characterised in that according to any one of claim 1~8
Preparation method obtains.
10. the pH response emulsion that star-type polymer described in claim 9 is stable in drug release, hydrogel field should
With.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107805295A (en) * | 2017-11-09 | 2018-03-16 | 陈晨特 | A kind of pH sensitive hydrogels with dissaving structure and preparation method and application |
WO2019023178A1 (en) * | 2017-07-28 | 2019-01-31 | Avery Dennison Corporation | Pressure sensitive adhesives and articles with hyperbranched silsesquioxane core and methods of making the same |
CN112022744A (en) * | 2020-09-14 | 2020-12-04 | 四川大学 | A hair dye containing functional surfactant, and its preparation method and application method |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104226275A (en) * | 2014-08-21 | 2014-12-24 | 中科院广州化学有限公司 | Hollow microsphere based on methacrylic acyloxy cage-like silsesquioxane and preparation method and application thereof |
CN104861098A (en) * | 2015-04-28 | 2015-08-26 | 中科院广州化学有限公司 | Star polymer with pH stimulating responsiveness, preparation method thereof and application |
CN105001733A (en) * | 2015-08-14 | 2015-10-28 | 兰州科天环保节能科技有限公司 | Super-hydrophobic outdoor water-borne wood coating and preparation method thereof |
-
2016
- 2016-08-05 CN CN201610640908.8A patent/CN106188573B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104226275A (en) * | 2014-08-21 | 2014-12-24 | 中科院广州化学有限公司 | Hollow microsphere based on methacrylic acyloxy cage-like silsesquioxane and preparation method and application thereof |
CN104861098A (en) * | 2015-04-28 | 2015-08-26 | 中科院广州化学有限公司 | Star polymer with pH stimulating responsiveness, preparation method thereof and application |
CN105001733A (en) * | 2015-08-14 | 2015-10-28 | 兰州科天环保节能科技有限公司 | Super-hydrophobic outdoor water-borne wood coating and preparation method thereof |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019023178A1 (en) * | 2017-07-28 | 2019-01-31 | Avery Dennison Corporation | Pressure sensitive adhesives and articles with hyperbranched silsesquioxane core and methods of making the same |
US11661533B2 (en) | 2017-07-28 | 2023-05-30 | Avery Dennison Corporation | Pressure sensitive adhesives and articles with hyperbranched silsesquioxane core and methods of making the same |
EP4306608A3 (en) * | 2017-07-28 | 2024-02-21 | Avery Dennison Corporation | Pressure sensitive adhesives and articles with hyperbranched silsesquioxane core and methods of making the same |
EP4303283A3 (en) * | 2017-07-28 | 2024-02-28 | Avery Dennison Corporation | Pressure sensitive adhesives and articles with hyperbranched silsesquioxane core and methods of making the same |
CN107805295A (en) * | 2017-11-09 | 2018-03-16 | 陈晨特 | A kind of pH sensitive hydrogels with dissaving structure and preparation method and application |
CN107805295B (en) * | 2017-11-09 | 2020-02-04 | 佛山市怡创生化科技有限公司 | pH-sensitive hydrogel with hyperbranched structure and preparation method and application thereof |
CN112022744A (en) * | 2020-09-14 | 2020-12-04 | 四川大学 | A hair dye containing functional surfactant, and its preparation method and application method |
CN112022744B (en) * | 2020-09-14 | 2021-06-15 | 四川大学 | A hair dye containing functional surfactant, and its preparation method and application method |
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