CN108285533A - A kind of polyamine organic polymer type dispersant - Google Patents
A kind of polyamine organic polymer type dispersant Download PDFInfo
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- CN108285533A CN108285533A CN201710013838.8A CN201710013838A CN108285533A CN 108285533 A CN108285533 A CN 108285533A CN 201710013838 A CN201710013838 A CN 201710013838A CN 108285533 A CN108285533 A CN 108285533A
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- polyamine
- polyetheramine
- dispersant
- organic polymer
- primary amine
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
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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
- C09K23/16—Amines or polyamines
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
A kind of polyamine high-molecular copolymer has following chemical structural formula：
Description
Technical field
The present invention relates to a kind of polyamine high-molecular copolymers, have in particular to a kind of polyamine of Biodegradable
Machine high-molecular type dispersing agent.
Background technology
Dispersant (dispersant) is a kind of addition dispersion liquid or on-surface-active polymer, tool in colloid system
Surface-active polymer or surfactant, main purpose be to promote in dispersion liquid or colloid system the separation of particle with how
Meter Hua avoids particle from generating the situation of sedimentation or agglutination (aggregation or flocculation), such as Chinese patent application
It announces No. 104650771A and proposes a kind of non-woven fabrics binder of tool nonylphenol polyoxyethylene ether (NPEO) dispersant, China specially
Sharp Shen Qing Publication the 104277617Ath propose a kind of sterilization water-repellent paint with nonyl phenol (nonyl phenol, NP) or
It is announced such as Chinese patent and proposes that a kind of nanometer oxide of tool nonylphenol polyoxyethylene ether dispersant divides in No. 101565568B
Dispersion composition.
However, the nonyl phenol in foregoing dispersant is Environmental Hormone, after the said goods are in use, there are discarded
Nonyl phenol and bisphenol-A in product are difficult to decompose in the environment, cause the harm of environmental pollution and biology, and because it is difficult to
Decompose that (organic compound is by the relative speed of biological decomposition in environment：Straight chain alkane ＞ branched alkane ＞ ring-type alkane ＞ aromatic series
Close object, Tran et al., 1997), bioaccumulation (bioaccumulation) can be penetrated and be deposited in the top in food chain
In consumer's body, such as the mammal etc. of the mankind or large size.Common people also readily penetrate through contact nonyl phenol and bisphenol-A is made
The product made, and by sucking or skin contact intake nonyl phenol and bisphenol-A.
According to the report at China National Institutes of Health (NHRI) National Environmental Toxicological Research center, nonyl phenol has female
Hormonal activity, and nerve may be influenced and develop and cause obesity with immune system；And bisphenol-A is through researches show that may influence
Brain develops, or influences hemopoietic system and improve the incidence of filial generation liver cancer and breast cancer.
Do not have environmental toxicity therefore how to prepare one, be easy to be provided simultaneously with the active dispersion of identical function for biological decomposition
Agent, for the technical task of the invention to be solved.
Invention content
According to above-mentioned, prepare one kind in order to reach and not having environmental toxicity, and be easy as biological decomposition and be provided simultaneously with identical
The purpose of the dispersant of functional activity, present invention firstly provides a kind of polyamine high-molecular copolymers, have following chemistry knot
Structure formula：
Wherein, DE is to be derived from a glycidol ether, and R is to be derived from a polyetheramine, m=1~10.
In above-mentioned purpose, in the better embodiment of the present invention, wherein glycidol ether is to be selected from：Isosorbide-5-Nitrae-fourth two
The group that alcohol diglycidyl ether, 1,6- hexanediol diglycidyl ethers and hydrogenated bisphenol A diglycidyl ether are formed.
In above-mentioned purpose, in the better embodiment of the present invention, wherein the polyetheramine is to be selected from：Difunctional primary
The group that the polyetheramine of amine, the polyetheramine of trifunctional primary amine are formed.
In addition, in another preferable practice of the present invention, it is to provide a kind of dispersant, including above-mentioned polyamine polymer copolymerization
Object.
Specific implementation mode
The present invention provides a kind of polyamine high-molecular copolymer, has following chemical structural formula：
Wherein, DE is to be derived from a glycidol ether, and R is to be derived from a polyetheramine, m=1~10.
First, the raw material that the embodiment of the present invention uses includes：
(1) 1,4-butanediol diglycidyl ether (Isosorbide-5-Nitrae-butanediol diglycidyl ether, Isosorbide-5-Nitrae-BDGE)：
Molecular weight is 202, and chemical structural formula is as follows：
(2) 1,6- hexanediol diglycidyl ether (1,6-Hexanediol diglycidyl ether, 1,6-HDGE)：
Molecular weight is 230, and chemical constitution is as follows：
(3) hydrogenated bisphenol A diglycidyl ether (hydrogenated bisphenol A diglycidyl ether)：
Molecular weight is 352, and chemical constitution is as follows：
(4) polyetheramine (Polyetheramine)：Polyetheramine can be difunctional primary amine or trifunctional primary amine, wherein double
Functional group's primary amine includes：Jeffamine D-230 (n=2.5, average molecular weight 240), Jeffamine D-400 (n=
6.1, average molecular weight 400) or Jeffamine D-2000 (n=33.1, average molecular weight 2000), chemical structural formula
It is as follows：
Trifunctional primary amine includes：Jeffamine T-403 (x+y+z=5~6, average molecular weight 440), chemistry
Structural formula is as follows：
Or Jeffamine T-3000 (x+y+z=50, average molecular weight 3000), Jeffamine T-5000 (x+y+z
=85, average molecular weight 5000), chemical structural formula is as follows：
By taking 1,4-butanediol diglycidyl ether as an example, tool bioerodible is synthesized with the polyetheramine of difunctional primary amine
The embodiment of the copolymer of the polyamine high-molecular type dispersing agent of property is as follows：
Embodiment 1
Isosorbide-5-Nitrae-BDGE (65.85g, 326mmol) and D-230 (104.32g, 434.67mmol) is added to three necks of 250mL
In bottle (Isosorbide-5-Nitrae-BDGE and D-230 moles ratio=3: 4), 4~8 hours of mechanic whirl-nett reaction are utilized less than 90 degree Celsius, with
FTIR (Fourier transform infrared spectroscopy) is monitored, as epoxy group characteristic absorption peak (910cm-1)
It disappears and indicates that reaction is completed, a kind of liquid of sticky state can be obtained, this is the organic high score of polyamine proposed by the invention
The copolymer of subtype dispersant.
Embodiment 2
Isosorbide-5-Nitrae-BDGE (49.29g, 244mmol) and D-400 (146.4g, 366mmol) is added in the three-necked bottle of 250mL
(Isosorbide-5-Nitrae-BDGE and D-400 moles ratio=2: 3), 4~8 hours of mechanic whirl-nett reaction are utilized less than 90 degree Celsius, are supervised with FTIR
Control, as epoxy group characteristic absorption peak (910cm-1) disappearing indicates that reaction is completed, and can obtain the liquid of sticky state, this is this
Invent the copolymer of proposed polyamine organic polymer type dispersant.
Embodiment 3
Isosorbide-5-Nitrae-BDGE (16.44g, 81.4mmol) and D-2000 (326g, 163mmol) is added in the three-necked bottle of 500mL
(Isosorbide-5-Nitrae-BDGE and D-2000 moles ratio=1: 2), 4~8 hours of mechanic whirl-nett reaction are utilized less than 90 degree Celsius, are supervised with FTIR
Control, as epoxy group characteristic absorption peak (910cm-1) disappearing indicates that reaction is completed, the liquid of sticky state, as this hair can be obtained
Bright proposed polyamine organic polymer type dispersant/copolymer.
Yu ShangThe embodiment 1 stated
In~3, the copolymer of synthesized polyamine organic polymer type dispersant, chemical constitution is as follows：
Wherein, when the polyetheramine of difunctional primary amine is D-230 in raw material, n=2.5, m=1~10；For D-400 when, n
=6.1, m=1~10；For D-2000 when, n=33.1, m=1~10.
In Examples 1 to 3,1,6- hexanediol diglycidyl ethers or hydrogenated bisphenol A diglycidyl ether also can be used
Replace 1,4-butanediol diglycidyl ether, the copolymerization of polyamine high-molecular type dispersing agent is carried out with the polyetheramine of difunctional primary amine
The synthesis of object.
The poly- of tool Biodegradable is synthesized with the polyetheramine of 1,4-butanediol diglycidyl ether and trifunctional primary amine
Amine high-molecular type dispersing agent.
Embodiment 4
Isosorbide-5-Nitrae-BDGE (55.75g, 276mmol) and T-403 (161.92g, 368mmol) is added in the three-necked bottle of 250mL
(Isosorbide-5-Nitrae-BDGE and T-403 moles ratio=3: 4), 4~8 hours of mechanic whirl-nett reaction are utilized less than 90 degree Celsius, with FTIR
(Fourier transform infrared spectroscopy) is monitored, as epoxy group characteristic absorption peak (910cm-1) disappear
Indicate that reaction is completed, and the liquid of sticky state can be obtained, this is that polyamine organic polymer type proposed by the invention disperses
Agent.
Embodiment 5
Isosorbide-5-Nitrae-BDGE (33.13g, 164mmol) and T-3000 (738g, 246mmol) is added in the three-necked bottle of 1000mL
(Isosorbide-5-Nitrae-BDGE and T-3000 moles ratio=2: 3), 4~8 hours of mechanic whirl-nett reaction are utilized less than 90 degree Celsius, with FTIR
(Fourier transform infrared spectroscopy) is monitored, as epoxy group characteristic absorption peak (910cm-1) disappear
It indicates that reaction is completed, can equally obtain the liquid of sticky state, polyamine organic polymer type as proposed by the invention point
Powder.
Embodiment 6
Isosorbide-5-Nitrae-BDGE (16.44g, 81.4mmol) and T-5000 (814g, 162.8mmol) is added to the three-necked bottle of 1000mL
In (Isosorbide-5-Nitrae-BDGE with T-5000 moles ratio=1: 2), less than 90 degree Celsius using 4~8 hours of mechanic whirl-nett reaction, with FTIR
(Fourier transform infrared spectroscopy) is monitored, as epoxy group characteristic absorption peak (910cm-1) disappear
It indicates that reaction is completed, the liquid of sticky state, polyamine organic polymer type as proposed by the invention dispersion can also be obtained
Agent.
In previous embodiment 4, synthesized polyamine organic polymer type dispersant, chemical constitution is as follows：
Wherein, when the polyetheramine of trifunctional primary amine is T-403 in raw material, x+y+z=5~6, m=1~10.
In previous embodiment 5~6, synthesized polyamine organic polymer type dispersant, chemical constitution is as follows：
Wherein, when the polyetheramine of trifunctional primary amine is T-3000 in raw material, x+y+z=50, m=1~10；For T-
When 5000, x+y+z=85, m=1~10.
In addition, in the above embodiments 4~6,1,6- hexanediol diglycidyl ethers or hydrogenated bisphenol A two also can be used
Glycidol ether replaces 1,4-butanediol diglycidyl ether, and polyamine polymer electrolyte point is carried out with the polyetheramine of trifunctional primary amine
Powder.
Then, the dispersion effect of dispersant made of polyamine polymer electrolyte copolymer provided by the present invention is surveyed
Examination.
The dispersion effect of dispersant is analyzed
Test is the polyamine macromolecule synthesized with the polyetheramine of 1,4-butanediol diglycidyl ether and difunctional primary amine
The dispersion effect of type dispersant, including：Polyamine high-molecular type dispersing agent provided by the invention, diluent (n-butyl
Glycidyl ether, BGE), 100% epoxy resin (Changchun BE188), filler (CaCO3), white toner (Huntsman
TR-81), black toner (Mitsubishi MA-100) is formulated as shown in table 1.1：
Table 1.1
By table 1.1 it is found that in the composition of comparative example 1 and comparative example 2, and it is not added with polyamine macromolecule proposed by the invention
Type dispersant, and mended total grams to 100g with diluent；In addition, according to the configuration embodiment 1 in table 1.1, embodiment 2, ratio
After example 1 and comparative example 1, then it is separately added into the bead (2mm) of equivalent, after oscillator concussion grinding one hour, carried out
The test of viscosity (cP) and particle size.
Test result is as follows shown in table 1.2：
Table 1.2
| Comparative example 1 | Embodiment 1 | Comparative example 2 | Embodiment 2 | |
| Viscosity (cP) | 797 | 679 | 31321 | 2217 |
| Average grain diameter (nm) | 127 | 112 | 783 | 88 |
Shown by the test result of table 1.2, add polyamine high-molecular type dispersing agent embodiment 1 and embodiment 2 compared to
Comparative example 1 and comparative example 2, viscosity is decreased obviously；Such as：Embodiment 1 declines nearly 15% compared to comparative example 1, viscosity；And
And embodiment 2, compared to comparative example 2, viscosity decrease beyond 90%, and thinning effect is more significant.
In addition, the test about particle size, is shown by 1.2 test result of table, addition polyamine high-molecular type dispersing agent
Compared to comparative example 1 and comparative example 2, average grain diameter is decreased obviously for embodiment 1 and embodiment 2；Such as：Embodiment 1 compares ratio
Compared with example 1, Average Particle Diameters decline nearly 11%；And embodiment 2, compared to comparative example 2, Average Particle Diameters decline close
89%, more highlight the dispersion effect of polyamine high-molecular type dispersing agent of the present invention.Show that the present invention carries by the test result of table 1.2
The polyamine high-molecular type dispersing agent gone out can effectively disperse toner in epoxy systems.The only polyamine macromolecule of offer of the invention
Type dispersant also may be used in addition to the dispersant that can be used as the pigment (pigment) such as the toner in ink (ink), coating (coating)
Dispersant as the products such as filler (filler) and plastics (plastic material), without being limited with pigment dispersing agent.
In conclusion polyamine high-molecular copolymer provided by the present invention, can be used as dispersant has good dispersion, separately
On the one hand, the polyamine high-molecular copolymer is without chemical compositions such as nonyl phenol or bisphenol-As, and straight chain alkyl structure is in natural environment
In the pollution that is easier to decompose without causing environment, so that the product of addition polyamine high-molecular copolymer of the present invention is more in line with now
The standard of environmental protection；Therefore the work of a present invention actually great industrial value.
The present invention as the personage Ren Shi craftsman for being familiar with this skill thinks and be it is all as modify, it is so neither de- such as attached to apply for a patent model
It encloses and is intended to protect.
Claims (5)
1. a kind of polyamine high-molecular copolymer has following chemical structural formula：
It is characterized in that, DE is to be derived from a glycidol ether, R is to be derived from a polyetheramine, m=1~10.
2. the polyamine high-molecular copolymer as described in claim the 1st, which is characterized in that the glycidol ether is to be selected from
In：1,4-butanediol diglycidyl ether, 1,6- hexanediol diglycidyl ethers and hydrogenated bisphenol A diglycidyl ether institute group
At group.
3. the polyamine high-molecular copolymer as described in claim the 1st, which is characterized in that the polyetheramine is to be selected from：
The group that the polyetheramine of difunctional primary amine, the polyetheramine of trifunctional primary amine are formed.
4. a kind of dispersant, which is characterized in that include the polyamine high-molecular copolymer of claims 1.
5. a kind of inorganic clay delamination agent, which is characterized in that include the polyamine high-molecular copolymer of claims 1.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108976414A (en) * | 2018-06-25 | 2018-12-11 | 烟台大学 | A kind of organic contracting amine polymer and preparation method thereof |
| CN109517160A (en) * | 2018-11-28 | 2019-03-26 | 宁波润禾高新材料科技股份有限公司 | A kind of preparation method of secondary amine type polyetheramine |
| CN111378108A (en) * | 2018-12-28 | 2020-07-07 | 江苏天奈科技股份有限公司 | Dispersing agent and synthetic method thereof, lubricant and preparation method thereof |
| CN111889025A (en) * | 2020-09-01 | 2020-11-06 | 山东大学 | Acid-alkali-resistant salt-resistant super-amphiphilic molecule emulsifier, preparation method thereof and emulsion |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108976414A (en) * | 2018-06-25 | 2018-12-11 | 烟台大学 | A kind of organic contracting amine polymer and preparation method thereof |
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| CN111889025A (en) * | 2020-09-01 | 2020-11-06 | 山东大学 | Acid-alkali-resistant salt-resistant super-amphiphilic molecule emulsifier, preparation method thereof and emulsion |
| CN111889025B (en) * | 2020-09-01 | 2022-01-11 | 山东大学 | Acid-alkali-resistant salt-resistant super-amphiphilic molecule emulsifier, preparation method thereof and emulsion |
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