CN106519249B - A kind of novel high molecular polymer, preparation method and its application - Google Patents

A kind of novel high molecular polymer, preparation method and its application Download PDF

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CN106519249B
CN106519249B CN201610926337.4A CN201610926337A CN106519249B CN 106519249 B CN106519249 B CN 106519249B CN 201610926337 A CN201610926337 A CN 201610926337A CN 106519249 B CN106519249 B CN 106519249B
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high molecular
molecular polymer
polymer
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dispersion
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CN106519249A (en
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张舜
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TIANJIN SURFYCHEM T&D CO Ltd
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TIANJIN SURFYCHEM T&D CO Ltd
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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
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
    • C08G81/025—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyether sequences
    • 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
    • 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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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
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  • Polymers & Plastics (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

The present invention provides a kind of novel high molecular polymer, preparation method and its application, which is the comb high molecular polymer carried out from graft modification by the side chain of a kind of styrene and double bond containing polymers of carboxylic acid；The polymer can by polystyrene maleic anhydride resin (SMA) with contain primary amino group and R2Combined molecule and the polyether monoamine polymer with primaquine group carry out acylation reaction and obtain；Also by polystyrene acrylic acid resins and primary amino group and R can be contained2Combined molecule and the polyether monoamine polymer with primaquine group carry out acylation reaction and obtain；Its application is usually to be combined into mixture with other Conventional solvents groups, and the mixture is as wetting agent or dispersing agent purposes.The high molecular polymer is used as dispersing agent, it is easier to go on smoothly sand milling dispersion process, the viscosity in process of lapping is low, and gained dispersion liquid has lasting stability.

Description

A kind of novel high molecular polymer, preparation method and its application
Technical field
The invention belongs to technical field of high-molecular polymer, and in particular to a kind of novel high molecular polymer, its preparation side Method and its application.
Background technique
Comb-shaped copolymer, which refers to multiple line style branches while being grafted on a main chain, to be formed by as comb form Polymer is a kind of special graft polymers.Comb polymer has good wetting action and peptizaiton, patent In CN101600740, the comb-shaped copolymer based on the phenylethylene/maleic anhydride copolymerization optionally replaced is disclosed, includes a variety of knots Structure, wetting and dispersion effect are preferable, but are no longer satisfied requirement of the sectional interest to dispersing agent performance, and therefore, it is necessary to performances More excellent dispersing agent.
Summary of the invention
The present invention provides a kind of novel high molecular polymer, preparation method and its application, which is by a kind of benzene The side chain of ethylene and double bond containing polymers of carboxylic acid carries out graft modification and next comb high molecular polymer, the polymer conduct Dispersing agent is widely used, for water-based system but is not limited to disperse inorganic or organic solid particles material in water-based system.
Present invention solves the technical problem that being achieved through the following technical solutions：A kind of novel high molecular polymer, has Such as flowering structure：
R is：Main chain is the saturated chain of C1-20, and side groups are styrene or carboxyl；
R1For：EOp-POq-R3Polyether structure；P, q is 0-100；
R2For：R3-X；
Containing R1Polymerized unit with contain R2Polymerized unit between be irregularities, arbitrarily arrange；
R3For：C1-20 alkane structure；
X is：OH,SO3, it is COOH, phosphate-based；
W+m+n=100%,
Wherein, w=1-15%, n ≠ 0.
A kind of preparation method of novel high molecular polymer, obtains by the following method：
Method one：By polystyrene maleic anhydride resin (SMA) and contain primary amino group and R2Combined molecule and have primary The polyether monoamine polymer of amine groups carries out acylation reaction and obtains；
Polystyrene maleic anhydride resin has following molecular structure：
Polystyrene maleic anhydride resin is preferably SMA resin；
Method two：By polystyrene acrylic acid resins and contain primary amino group and R2Combined molecule and with primaquine group Polyether monoamine polymer carries out acylation reaction and obtains；
Polystyrene acrylic acid resins have following molecular structure：
Polystyrene acrylic acid resins are preferably Joncryl resin (BASF AG's offer)；
The polyether monoamine polymer of primaquine group has following molecule：
R=H for (EO), or CH3 for(PO)
The polyether monoamine polymer of primaquine group is preferably JEFFAMINE；
For method one and method two：
Preferably, the carboxyl reserved in molecule is the 20-80% of resin before reacting；It is preferred that 40-60%.
Preferably, reaction process should carry out in water or organic solvent；
Preferably, reaction need to carry out at 20-250 DEG C, when being reacted in water, temperature is more preferably 30-100 DEG C, when being reacted in organic solvent, temperature is more preferably 100-200 DEG C.
A kind of application of novel high molecular polymer has such as under type：
A kind of novel high molecular polymer is combined into mixture with other Conventional solvents groups, the mixture as wetting agent or Dispersing agent purposes；
A kind of novel high molecular polymer is used for dispersing solid powder, preferred battery material, inorganic pigment, organic pigment Or filler；
A kind of novel high molecular polymer, for the dispersion of cell size, the dispersion of printing ink paint, mill base concentrate point It dissipates or solid particles surface is modified.
Beneficial effects of the present invention are：The present invention provides a kind of novel high molecular polymer and preparation method and applications, This high molecular polymer is used as dispersing agent, it is easier to go on smoothly sand milling dispersion process, the viscosity in process of lapping is low, institute Obtaining dispersion liquid has lasting stability.
Specific embodiment
The present invention is described further with reference to embodiments：
It is to walk as application method of the dispersing agent to solid particle about Novel polymer disclosed in this invention It is rapid as follows：
(1) configuration 30% without aqueous resin dispersion liquid：Weigh the quality (calculating with solid content) of dispersing agent first as dispersion The 40% of solid particle gross mass, is added to the water, and stirs evenly addition wetting agent T-87 (the luxuriant and rich with fragrance chemistry of Tianjin match The production of development in science and technology Co., Ltd), adding the easily happy DF-220 defoaming agent of painting, (Tianjin Surfychem T&D Co., Ltd. is raw It produces)；
(2) dispersed：Solid powder is added to the configured dispersion liquid kind of step (1), excess water is added again, makes Solid content is 30%, 30 DEG C is kept the temperature in horizontal sand mill DX-100 grinding distribution 2 hours.
The formula of dispersion experiment is as shown in table 1：
Table 1
Component Dosage (%, by mass)
Solid particle 30
Dispersing agent (butt) 12
T-87 0.3
DF-220 0.2
Water Surplus
It is total 100
It is fixed as the stably dispersing effect evaluation method of dispersing agent about Novel polymer disclosed in this invention Justice is：
(1) viscosity evaluation assessment：It will be scattered in container and be saved as in 40 DEG C of insulating boxs, and observe viscosity and mobility Variation does not continue to evaluate if discovery dispersion liquid loses flowing；The standard of viscosity evaluation assessment is as shown in table 2.
Table 2
● Dispersion process of lapping is smooth, and dispersion viscosity is low, stores 10 days without obvious thickening
○ Dispersion process of lapping is smooth, and dispersion liquid is slightly higher, and 2 viscosity of storage increase and lose flowability
△ Dispersion process is difficult, and thixotropy is obvious, loses flowability in 1 day
× It is unable to complete dispersion process
(2) flocculation evaluation assessment：It will be scattered in container and be saved as in 40 DEG C of insulating boxs, observation dispersion liquid flocculation feelings Flocculated sediment is taken out and is weighed, then calculates rate of deposition P% by condition,
Wherein：WsFor sediment quality, WlFor dispersion liquid gross mass, C is dispersion liquid solids concentration；Specific flocculation is commented The standard of valence method is as shown in table 3.
Table 3
★ 10 days flocculation contents are stored less than 5%
☆ It stores 3 days flocculation contents and is greater than 5% and less than 30%
◇ It stores 3 days flocculation contents and is greater than 30% and less than 60%
× It is layered in 1 day
Embodiment 1
Take Sma-1000P (Total Cray Valley production) resin 100g (0.427mol acid anhydrides), it is put into In glass four-hole bottle of the 2000ml with stirring and condenser, it is addedM-2005 amine terminated polyether Then it is solid that 5g is added in the mixture of (production of huntsman company) 440g (0.22mol) and 36g (0.21mol) aminobenzenesulfonic acid Body acid catalyst (Tianjin Surfychem T&D Co., Ltd.'s production) and deionized water 864g；It is 80 DEG C of reactions 4 in temperature Hour, obtain light yellow transparent liquid product 1411g, yield 98%.
Embodiment 2
Take Sma-2000P resin (Total Cray Valley production) 100g (0.316mol acid anhydrides), it is put into In glass four-hole bottle of the 1000ml with stirring and condenser, it is added(huntsman company is raw by M-2070 Produce) mixture of 329g (0.164mol) and 12.6 (0.17mol) amion acetic acids, 4g solid acidifier is then added and (matches Tianjin The production of luxuriant and rich with fragrance chemistry development in science and technology Co., Ltd) and deionized water 442g；It is 80 DEG C in temperature to react 4 hours, obtains faint yellow Prescribed liquid product 866g, yield 98%.
Embodiment 3
It takes678 resins (BASF AG's offer) 100g (0.38mol carboxyl), be put into 500ml band stirring and In the glass four-hole bottle of condenser, it is addedM-1000 polyethers (production of huntsman company) 100g Then 3g solid acidifier (the luxuriant and rich with fragrance chemistry science and technology hair of Tianjin match is added in the mixture of (0.1mol) and 6.1g ethanol amine (0.1mol) Open up Co., Ltd's production) and dimethylbenzene 200g；It is 140 DEG C in temperature to react 4 hours, obtains light yellow transparent liquid product 179.2g, yield 87%.
Embodiment 4
It takes678 resins (BASF AG's offer) 100g (0.38mol carboxyl), be put into 500ml band stirring and In the glass four-hole bottle of condenser, it is addedM-1000 polyethers (production of huntsman company) 100g Then 3g solid acidifier (the luxuriant and rich with fragrance chemistry science and technology of Tianjin match is added in the mixture of (0.1mol) and 7.5g amion acetic acid (0.1mol) Development Co., Ltd's production) and dimethylbenzene 200g；It is 140 DEG C in temperature to react 4 hours, obtains light yellow transparent liquid product 184.6g, yield 89%.
Embodiment 5
It takes671 resins (BASF AG's offer) 100g (0.38mol carboxyl), be put into 500ml band stirring and In the glass four-hole bottle of condenser, it is addedM-2000 (production of huntsman company) 200g (0.1mol) With the mixture of 10g ethanol amine (0.16mol), 3g solid acidifier (the limited public affairs of the luxuriant and rich with fragrance chemical development in science and technology of Tianjin match are then added Department's production) and dimethylbenzene 150g；It is 145 DEG C in temperature to react 6 hours, obtains light yellow transparent liquid product 266.7g, yield It is 86%.
Comparative example 6
According to the mentioned polymer 1 of the implementation method preparation in patent CN101600740, code name is named herein：bk-1.
Comparative example 7
According to the mentioned polymer 2 of the implementation method preparation in patent CN101600740, code name is named herein：bk-2.
Comparative example 8
According to the mentioned polymer 3 of the implementation method preparation in patent CN101600740, code name is named herein：bk-3.
Comparative example 9
According to the mentioned polymer 5 of the implementation method preparation in patent CN101600740, code name is named herein：bk-4.
Respectively with viscosity evaluation assessment defined in the present invention and flocculation evaluation assessment to the embodiment of the present invention 1-5 and comparison The dispersion stabilization of embodiment 6-9 is evaluated, and evaluation result is as shown in table 4 and table 5.
Table 4
Experiment numbers Dispersing agent sample Carbon black pigment Organic pigment Inorganic pigment Titanium dioxide Iron oxide Cell size
1 Embodiment 1 ● ● ● ● ● ●
2 Embodiment 2 ● ● ● ● ● ●
3 Embodiment 3 ● ● ● ● ● ●
4 Embodiment 4 ● ● ● ● ● ●
5 Embodiment 5 ● ● ● ● ● ●
6 bk-1 × ○ △ ○ △ ○
7 bk-2 △ ○ △ × ● ○
8 bk-3 ● ○ × △ ○ △
9 bk-4 × △ △ ● ○ △
Table 4 is evaluation result table of the viscosimetry to embodiment, compare viscosity evaluation assessment standard (as shown in table 2), to divide Scattered effect is evaluated., it can be seen that using high molecular polymer (embodiment 1-5) of the invention as dispersing agent, to carbon black Pigment, organic pigment, inorganic pigment, titanium dioxide, iron oxide have good dispersion effect, that is, store 10 days flocculation contents and be less than 5%；And the dispersion effect of comparative example 6-9 is poor, in addition to bk-2 to iron oxide, bk-3 to charcoal blacks and bk-4 to titanium The dispersion effect of white powder can match in excellence or beauty with the present invention, and rest part presentation dispersion stabilization is poor, and (dispersion process of lapping is smooth, dispersion Liquid is slightly higher, and 2 viscosity of storage increase and lose flowability) the phenomenon that, difficulties in dispersion is presented in part, and (dispersion process is difficult, thixotropy Obviously, lose flowability in 1 day) the phenomenon that, some is even unable to complete dispersion.
Table 5
Experiment numbers Dispersing agent sample Carbon black pigment Organic pigment Inorganic pigment Titanium dioxide Iron oxide Cell size
1 Embodiment 1 ★ ★ ★ ★ ★ ★
2 Embodiment 2 ★ ★ ★ ★ ★ ★
3 Embodiment 3 ★ ★ ★ ★ ★ ★
4 Embodiment 4 ★ ★ ★ ★ ★ ★
5 Embodiment 5 ★ ★ ★ ★ ★ ★
6 bk-1 × ☆ ◇ ☆ ◇ ☆
7 bk-2 ◇ ☆ ◇ × ● ☆
8 bk-3 ● ☆ × ◇ ☆ ◇
9 bk-4 × ◇ ◇ ● ☆ ◇
Table 5 is evaluation result table of the flocculence to embodiment, to the standard (as shown in table 3) of flocculence evaluation assessment, to point The stability of dispersion liquid is evaluated.As can be seen that using high molecular polymer (embodiment 1-5) of the invention as dispersing agent, There is good dispersion effect to carbon black pigment, organic pigment, inorganic pigment, titanium dioxide, iron oxide, i.e. dispersion process of lapping is suitable Benefit, dispersion viscosity is low, stores 10 days without obvious thickening, dispersion liquid has excellent stability；And comparative example 6-9's is steady Qualitative best performance is only to store 3 days flocculation contents greater than 5% and less than 30%, and the poor (storage 3 days of stablizing effect is presented in part Content of flocculating less than 60%) the phenomenon that, some is even with regard to being layered in 1 day, it is seen then that the stability of comparative example 6-9 is complete The stability of the embodiment of the present application cannot be reached entirely,.
Evaluation by viscosity evaluation assessment and flocculation evaluation assessment to 1-5 of the embodiment of the present invention and comparative example 6-9, shows So, high molecular polymer provided by the invention as application of dispersant have excellent dispersion performance and stability, this for The development of relevant industries is of great significance.
The above embodiments merely illustrate the technical concept and features of the present invention, is not intended to limit the invention, all in this hair Within bright spirit and principle, made any modification, equivalent replacement etc. be should all be included in the protection scope of the present invention.

Claims (8)

1. a kind of preparation method of high molecular polymer, which is characterized in that be prepared via a method which：
By polystyrene acrylic acid resins and contain primary amino group and R2Combined molecule and the polyether monoamine polymerization with primaquine group Object carries out acylation reaction and obtains；
Polystyrene acrylic acid resins are Joncryl resin；Polyether monoamine polymer with primaquine group is JEFFAMINE；
R2For-R3-X；
R3For the alkyl of C1-20；
X is-OH ,-COOH or phosphate-based.
2. a kind of preparation method of high molecular polymer as described in claim 1, which is characterized in that the carboxyl in molecule retains Amount is the 20-80% of resin before reacting.
3. a kind of preparation method of high molecular polymer as described in claim 1, which is characterized in that reaction process is in water or has It is carried out in solvent.
4. a kind of preparation method of high molecular polymer as described in claim 1, which is characterized in that reaction is at 20-250 DEG C It carries out.
5. a kind of high molecular polymer, which is characterized in that be made by preparation method of any of claims 1-4.
6. a kind of application of high molecular polymer as claimed in claim 5, which is characterized in that used as wetting agent or dispersing agent On the way.
7. the application of high molecular polymer as claimed in claim 6, which is characterized in that be used for dispersing solid powder.
8. the application of high molecular polymer as claimed in claim 6, which is characterized in that dispersion, ink for cell size The dispersion of coating, the dispersion of mill base concentrate or solid particles surface are modified.
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CN108479632B (en) * 2018-04-10 2020-08-11 佛山市贝特尔化工有限公司 Preparation method of water-based dispersant with pigment universality
CN109666148A (en) * 2018-12-29 2019-04-23 东来涂料技术（上海）股份有限公司 A kind of preparation method of aqueous dispersion
CN109970982B (en) * 2019-01-23 2021-12-10 天津赫普菲乐新材料有限公司 Comb-modified styrene-carboxylic acid copolymer
CN113474918A (en) * 2019-02-26 2021-10-01 毕克化学有限公司 Composition comprising comb copolymer
CN110078930A (en) * 2019-05-29 2019-08-02 天津赫普菲乐新材料有限公司 A kind of comb shape modified phenylethylene-polymers of carboxylic acid and its application
CN110585992B (en) * 2019-09-25 2021-09-14 苏州大学 Synthesis of novel surfactant and preparation of stable liquid metal nano liquid drop by using same
CN115197381B (en) * 2022-09-16 2022-11-25 广州鹿山新材料股份有限公司 Unsaturated SMA resin modified polypropylene and preparation method thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0985691A1 (en) * 1998-09-10 2000-03-15 Dow Deutschland Inc., Zweigniederlassung Stade Process for preparing hydrophobically modified low foaming copolymers, hydrophobically modified low foaming copolymers and their use as cement additives
US6423785B1 (en) * 1999-02-05 2002-07-23 Goldschmidt Ag Maleic anhydride copolymers containing amine oxide groups and their use as dispersants for pigments of fillers
CN1420135A (en) * 2001-11-15 2003-05-28 中日合成化学股份有限公司 Antistatic material and mfg. method thereof
CN101600740A (en) * 2006-12-27 2009-12-09 比克化学股份有限公司 Modified comb copolymers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0985691A1 (en) * 1998-09-10 2000-03-15 Dow Deutschland Inc., Zweigniederlassung Stade Process for preparing hydrophobically modified low foaming copolymers, hydrophobically modified low foaming copolymers and their use as cement additives
US6423785B1 (en) * 1999-02-05 2002-07-23 Goldschmidt Ag Maleic anhydride copolymers containing amine oxide groups and their use as dispersants for pigments of fillers
CN1420135A (en) * 2001-11-15 2003-05-28 中日合成化学股份有限公司 Antistatic material and mfg. method thereof
CN101600740A (en) * 2006-12-27 2009-12-09 比克化学股份有限公司 Modified comb copolymers

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