CN109776710A - Structure containing phenylethylene-maleic anhydride and the waterborne pigment dispersant and preparation method thereof of graft modification - Google Patents
Structure containing phenylethylene-maleic anhydride and the waterborne pigment dispersant and preparation method thereof of graft modification Download PDFInfo
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Abstract
The invention discloses a kind of structure containing phenylethylene-maleic anhydride and the waterborne pigment dispersants and preparation method thereof of graft modification, it is with styrene, styrene derivative, after four kinds of monomers of maleic anhydride and acrylic acid derivative carry out free-radical polymerized formation block copolymer, graft modification is carried out with graft modification agent on the block copolymer, the waterborne pigment dispersant of structure containing phenylethylene-maleic anhydride and graft modification is prepared, the dispersing agent steric hindrance is big, anchoring ability is strong, pigment stabilizer can be made to disperse in aqueous color paste application, relative color strength is stronger, storage stability is preferable.
Description
Technical field
The present invention relates to a kind of waterborne pigment dispersants and preparation method thereof, more particularly to one kind to contain styrene-maleic acid
Acid anhydride structure and the waterborne pigment dispersant and preparation method thereof of graft modification, belong to technical field of fine.
Background technique
Granules of pigments is stably dispersed in the aqueous color paste formed in water-based system, is to avoid pigment dust pollution and raising
One effective scheme of the using effects such as tinting strength, tinting power, vividness and brightness.Dispersing agent is to guarantee that granules of pigments being capable of stable dispersion
Key assistant in water-based system has important shadow to aqueous color paste tinting strength, tinting power, with application performances such as colored matrix materials compatibilities
It rings.Dispersing agent is not only required to be anchored on pigment particle surface well, it is also necessary to the scattered face in aqueous color paste
There is provided stronger steric hindrance and electrostatic repulsion between material particle, to prevent the reunion of granules of pigments, therefore for dispersant structure,
Molecular weight, the distribution of hydrophilic and anchor fixed group etc. have higher requirements.Block copolymer includes two or more property
The good characteristic of multiple polymers can be combined together by different polymer segments, and segmented copolymer can provide
Functional and micro structure more abundant, is paid more and more attention, has a wide range of applications in mill base dispersing agent.
Styrene-maleic anhydride copolymer is due to function admirable, cheap and be widely used in auto parts and components, household electrical appliances
The every field such as shell, construction material, office appliance and medical device.However, existing styrene-maleic anhydride copolymer by
It is smaller in steric hindrance, and potential point is less, influences styrene-maleic anhydride copolymer as pigment dispersing agent, thinner etc.
The application performance of product, in order to obtain the more excellent styrene-maleic anhydride copolymer of performance, prior art discloses benzene second
The polymer of alkene, maleic anhydride and various of monomer: application No. is the Chinese patents of CN201410327081.6 to disclose one kind four
Membered copolymer dispersing agent, the quadripolymer dispersing agent are by unsaturated polyether, hydroxyethyl methacrylate, styrene, benzene second
Alkene sodium sulfonate is copolymerized；Application No. is the Chinese patents of CN201510982711.8 to disclose a kind of polymer blocks dispersion
Agent, be by methacrylic acid, sodium styrene sulfonate, n-isopropyl acrylamide polymerization, then again with hydroxyethyl methacrylate,
Allyl alcohol polyethenoxy ether polymerization, obtains polymer blocks application of dispersant in nano-titanium dioxide, calcium carbonate, ink pigment
The dispersion of grain.The prior art, which also discloses, is modified styrene-maleic anhydride copolymer, to increase styrene-maleic acid
The compatibility of anhydride copolymer and solvent is to enhance dispersion effect: application No. is the Chinese patents of CN201710524237.3 to disclose
A kind of styrene-maleic anhydride copolymer modified with alkyl phenol polyoxyethylene ether, the copolymer are used for high gum asphalt
Heavy crude thinner.A kind of dispersing agent for ink-jet ink is disclosed in a kind of ink jet printing method of United States Patent (USP) US6406143,
The dispersing agent is modified to phenylethylene-maleic anhydride with the compound containing amine.
However, most of styrene-maleic anhydride copolymer is poor due to anchoring ability deficiency and steric hindrance, it is difficult to maintain
Steric hindrance between high concentration pigment and be easy to happen secondary flocculation, cause mill base stabilization poor, preparation high-performance styrene-horse
The pigment dispersing agent for carrying out acid anhydride structure is an important process of field of fine chemical.
Summary of the invention
In order to overcome current phenylethylene-maleic anhydride dispersing agent anchoring ability insufficient and the disadvantage of steric hindrance difference, this hair
It is bright to provide the waterborne pigment dispersant and preparation method thereof of a kind of structure containing phenylethylene-maleic anhydride and graft modification, by this
The block copolymer that dispersing agent is graft modification is prepared in preparation method.
The technical scheme is that
The invention discloses a kind of systems of waterborne pigment dispersant containing phenylethylene-maleic anhydride structure and graft modification
Preparation Method, the preparation method include the following steps:
S1: the preparation of block copolymer solution: by styrene, styrene derivative, maleic anhydride, acrylic acid derivative four
Kind monomer and solvent are made into mixed solution and are placed in reactor, and in inert gas shielding and temperature control is at 70~100 DEG C
Under the conditions of, the mixture that initiator, chain-transferring agent and solvent form is slowly added dropwise into reactor, preferred time for adding is
2~4 hours, the reaction was continued after completion of dropwise addition 1~3h, obtain block copolymer solution；
S2: the preparation of graft modification block copolymer: grafting is added in the block copolymer solution that step S1 is obtained and changes
Property agent and catalyst carry out graft reaction, reaction temperature be 70~100 DEG C, the reaction time be 2~6h, remove after reaction molten
Agent is simultaneously cooled to room temperature, and obtains graft modification block copolymer.
Its further technical solution is:
In S1 step:
The styrene derivative is the compound with logical formula (I) structure:
Wherein, R1For H or methyl；R2For the alkyl containing carbon number between 1~10, contain 1 and 10.And the styrene derivative
Esterification is occurred and is made by vinyl benzene methanol and the alkyl acid containing carbon number between 1~11 (containing 1 and 11), the esterification
For conventional esterification, specific preparation method is repeated no more in the application.
The acrylic acid derivative is the compound with logical formula (II) structure:
Wherein, R3For H or methyl, R4For containing alkyl of the carbon number between 1~10 or the alkyl containing carbon number between 1~10
Alcohol contains 1 and 10.
The solvent is one of 1,4- dioxane, thiacyclohexane, tetrahydrofuran and isopropanol.
The initiator is azodiisobutyronitrile, azobisisoheptonitrile, benzoyl peroxide, cumyl peroxide, mistake
Oxidation two special at least one of butyl ester and perbenzoic acid spy's butyl ester.
The chain-transferring agent is lauryl mercaptan or α-methylstyrene linear dimerization body.
The inside reactor in the method for inert gas shielding, preferably nitrogen as protective gas, can pass through to
Inside reactor continuously leads to the method for nitrogen 15-30min, empties the oxygen in reactor, avoids oxygen to the shadow of chemical reaction
It rings.
In above-mentioned steps S1, with styrene, styrene derivative, four kinds of monomers of maleic anhydride and acrylic acid derivative it is total
Quality meter, styrene account for the 14%~27% of four kinds of monomer gross mass, and styrene derivative accounts for the 28% of four kinds of monomer gross mass
~55%, maleic anhydride accounts for the 13%~25% of four kinds of monomer gross mass, and acrylic acid derivative accounts for four kinds of monomer gross mass
17%~38%；Initiator accounts for the 5%~10% of four kinds of monomer gross mass, chain-transferring agent account for four kinds of monomer gross mass 3%~
5%.
In S2 step:
The graft modification agent is the compound with logical formula (III) structure:
Wherein, R5、R6And R7For one of methyl, ethyl, methoxy or ethoxy, and R5、R6And R7Independently of each other；n
It is the integer between 1-10, contains 1 and 10.Preferably, which is 3- aminopropyl front three oxosilane, 3- aminopropyl
One of triethoxysilane, 3- dimethyl methoxy silane and 3- aminopropyl diethoxymethylsilane.And
The quality of the graft modification agent accounts for the 40%~80% of maleic anhydride quality.
The catalyst is one of p-methyl benzenesulfonic acid, alchlor, triethylamine, 4-dimethylaminopyridine and pyridine,
Its dosage is the conventional amount used of catalyst used in amino and anhydride reaction, which is well-known to those skilled in the art
Technical solution repeats no more in the application.
The present invention, which also describes more than one and states preparation method, to be prepared resulting structure containing phenylethylene-maleic anhydride and is grafted
Modified waterborne pigment dispersant, the dispersing agent are with styrene, styrene derivative, maleic anhydride and acrylic acid derivative four
After kind monomer carries out free-radical polymerized formation block copolymer, graft modification is carried out with graft modification agent on the block copolymer
It is prepared, wherein used styrene derivative, acrylic acid derivative and graft modification agent are as previously described.
The present invention also describes a kind of application of above-mentioned waterborne pigment dispersant in water-based pigment colour paste.
The method have the benefit that: the present invention is spread out with styrene, styrene derivative, maleic anhydride and acrylic acid
After four kinds of monomers of biology carry out free-radical polymerized formation block copolymer, connect on the block copolymer with graft modification agent
Branch is modified, and the waterborne pigment dispersant of structure containing phenylethylene-maleic anhydride and graft modification, the dispersing agent space bit is prepared
Resistance is big, anchoring ability is strong, pigment stabilizer can be made to disperse in aqueous color paste application, relative color strength is stronger, storage stability
Preferably.
Specific embodiment
In order to better understand the technical means of the present invention, it and can be implemented in accordance with the contents of the specification, below
In conjunction with specific embodiments, specific embodiments of the present invention will be described in further detail, and following embodiment is for illustrating this hair
It is bright, but be not intended to limit the scope of the invention.
The chemical structure of styrene derivative used by following specific embodiments and comparative example and acrylic acid derivative is such as
It is lower described:
Styrene derivative is the compound with logical formula (I) structure:
In styrene derivative A1, R1For methyl, R2For C5H11；
In styrene derivative A2, R1For H, R2For C10H21；
In styrene derivative A3, R1For methyl, R2For CH3。
The acrylic acid derivative is the compound with logical formula (II) structure:
In acrylic acid derivative B1, R3For methyl, R4For C5H10OH；
In acrylic acid derivative B2, R3For H, R4For CH3；
In acrylic acid derivative B3, R3For H, R4For C10H21。
Specific embodiment 1
By 27 parts of styrene, 32 parts of styrene derivative A1,18 parts of maleic anhydrides, 23 parts of acrylic acid derivative B1, tetra- kinds of lists
Body and 300 parts of Isosorbide-5-Nitrae-dioxane are made into mixed solution and are placed in reactor, are passed through nitrogen 25min and control temperature 85
DEG C, 8 parts of azodiisobutyronitriles, 4 parts of lauryl mercaptans and 50 parts of Isosorbide-5-Nitraes-dioxane composition mixed liquor are slowly added dropwise to reaction
In device, time for adding is 3 hours, and the reaction was continued after completion of dropwise addition 2 hours；Continuously add 10.8 parts of 3- aminopropyl trimethoxy silicon
Alkane and 4 parts of p-methyl benzenesulfonic acid, reaction temperature are 85 DEG C, and the reaction time is 4 hours, after reaction, remove Isosorbide-5-Nitrae-dioxane,
It is cooled to room temperature, obtains the waterborne pigment dispersant containing phenylethylene-maleic anhydride and graft modification.
Specific embodiment 2
By 15 parts of styrene, 40 parts of styrene derivative A2,25 parts of maleic anhydrides, 20 parts of acrylic acid derivative B2, tetra- kinds of lists
Body and 300 parts of thiacyclohexanes are made into mixed solution and are placed in reactor, are passed through nitrogen 15min, and temperature is controlled at 100 DEG C, by 8 parts
The mixed liquor of benzoyl peroxide, 4 parts of α-methylstyrene linear dimerization bodies and 50 parts of thiacyclohexanes composition, is slowly added dropwise to reaction
In device, time for adding is 2 hours, and the reaction was continued after completion of dropwise addition 3 hours；Continuously add 10.8 parts of 3- aminopropyl triethoxies
Silane and 4 parts of alchlors, reaction temperature are 100 DEG C, and the reaction time is 2 hours, after reaction, remove thiacyclohexane, cooling
To room temperature, the waterborne pigment dispersant containing phenylethylene-maleic anhydride and graft modification is obtained.
Specific embodiment 3
By 21 parts of styrene, 28 parts of styrene derivative A3,13 parts of maleic anhydrides, 38 parts of acrylic acid derivative B3, tetra- kinds of lists
Body and 300 parts of tetrahydrofurans are made into mixed solution and are placed in reactor, are passed through nitrogen 30min, and temperature is controlled at 70 DEG C, by 8
The mixed liquor of part cumyl peroxide, 4 parts of lauryl mercaptans and 50 parts of tetrahydrofurans composition, is slowly added dropwise into reactor, drips
It is 4 hours between added-time, the reaction was continued after completion of dropwise addition 1 hour；Continuously add 10.8 parts of 3- dimethyl methoxy silanes
With 4 parts of triethylamines, reaction temperature is 70 DEG C, and the reaction time is 6 hours, after reaction, removes tetrahydrofuran, is cooled to room
Temperature obtains the waterborne pigment dispersant containing phenylethylene-maleic anhydride and graft modification.
Specific embodiment 4
By 14 parts of styrene, 55 parts of styrene derivative A1,14 parts of maleic anhydrides, 17 parts of acrylic acid derivative B3, tetra- kinds of lists
Body and 300 parts of isopropanols are made into mixed solution, are placed in reactor, are passed through nitrogen 20min, and temperature is controlled at 90 DEG C, by 8 parts
The mixed liquor of the special butyl ester of peroxidating two, 4 parts of α-methylstyrene linear dimerization bodies and 50 parts of isopropanols composition, is slowly added dropwise to anti-
It answers in device, time for adding is 3 hours, and the reaction was continued after completion of dropwise addition 3 hours；Continuously add 10.8 parts of 3- aminopropyl diethoxies
Butyldimethylsilyl and 4 parts of 4-dimethylaminopyridine, reaction temperature are 90 DEG C, and the reaction time is 3 hours, after reaction, are removed
Isopropanol is cooled to room temperature, and obtains the waterborne pigment dispersant containing phenylethylene-maleic anhydride and graft modification.
Comparative example 5
59 parts of styrene, 41 parts of maleic anhydrides and 300 parts of 1,4- dioxane are made into mixed solution and are placed in reactor
In, it is passed through nitrogen 25min, temperature is controlled at 85 DEG C, by 8 parts of azodiisobutyronitriles, 4 parts of lauryl mercaptans and 50 parts of Isosorbide-5-Nitrae-dioxies six
The mixed liquor of ring composition, is slowly added dropwise into reactor, and time for adding is 3 hours, and the reaction was continued after completion of dropwise addition 2 hours；After
Continuous that 24.6 parts of 3- aminopropyl front three oxosilanes and 4 parts of p-methyl benzenesulfonic acid are added, reaction temperature is 85 DEG C, and the reaction time is 4 small
When, after reaction, Isosorbide-5-Nitrae-dioxane is removed, is cooled to room temperature, obtains waterborne pigment dispersant.
Comparative example 6
By 27 parts of styrene, 32 parts of sodium styrene sulfonate, 18 parts of maleic anhydrides, 23 parts of acrylic acid derivative B1, tetra- kinds of monomers
It is made into mixed solution with 300 parts of Isosorbide-5-Nitrae-dioxane, is placed in reactor, nitrogen 25min is passed through, temperature is controlled at 85 DEG C,
8 parts of azodiisobutyronitriles, 4 parts of lauryl mercaptans and 50 parts of Isosorbide-5-Nitraes-dioxane composition mixed liquor are slowly added dropwise to reactor
In, time for adding is 3 hours, and the reaction was continued after completion of dropwise addition 2 hours；Continuously add 10.8 parts of 3- aminopropyl front three oxosilanes
With 4 parts of p-methyl benzenesulfonic acid, reaction temperature is 85 DEG C, and the reaction time is 4 hours, after reaction, removes Isosorbide-5-Nitrae-dioxane, cold
But to room temperature, waterborne pigment dispersant is obtained.
Comparative example 7
By 27 parts of styrene, 32 parts of styrene derivative A1,18 parts of maleic anhydrides, 23 parts of acrylic acid derivative B1, tetra- kinds of lists
Body and 300 parts of Isosorbide-5-Nitrae-dioxane are made into mixed solution, are placed in reactor, are passed through nitrogen 25min, and temperature is controlled 85
DEG C, 8 parts of azodiisobutyronitriles, 4 parts of lauryl mercaptans and 50 parts of Isosorbide-5-Nitraes-dioxane composition mixed liquor are slowly added dropwise to reaction
In device, time for adding is 3 hours, and the reaction was continued after completion of dropwise addition 2 hours；Continuously add 10.8 parts of γ-methacryloxies
Propyl trimethoxy silicane and 4 parts of p-methyl benzenesulfonic acid, reaction temperature are 85 DEG C, and the reaction time is 4 hours, after reaction, are removed
Isosorbide-5-Nitrae-dioxane is removed, is cooled to room temperature, waterborne pigment dispersant is obtained.
Comparative example 8
By 27 parts of styrene, 32 parts of styrene derivative A1,18 parts of maleic anhydrides, 23 parts of acrylic acid derivative B1, tetra- kinds of lists
Body and 300 parts of Isosorbide-5-Nitrae-dioxane are made into mixed solution, are placed in reactor, are passed through nitrogen 25min, and temperature is controlled 85
DEG C, 8 parts of azodiisobutyronitriles, 4 parts of lauryl mercaptans and 50 parts of Isosorbide-5-Nitraes-dioxane composition mixed liquor are slowly added dropwise to reaction
In device, time for adding is 3 hours, and the reaction was continued after completion of dropwise addition 2 hours；10.8 parts of ethanol amines and 4 parts are continuously added to toluene
Sulfonic acid, reaction temperature are 85 DEG C, and the reaction time is 4 hours, after reaction, remove Isosorbide-5-Nitrae-dioxane, are cooled to room temperature, obtain
To waterborne pigment dispersant.
Concrete application embodiment 9~12 and preparing for comparison 13~16 aqueous color paste of Application Example are as follows:
By 35 parts of pigment yellows, 74,5 parts of dispersing agents, 2 parts of propylene glycol and 58 parts of deionized waters through mixing dispersion, grinding, filtering
Obtain aqueous color paste.Wherein dispersing agent and Application Example corresponding relationship such as table 1.
The corresponding relationship of table 1 dispersing agent and aqueous color paste
The above-mentioned aqueous color paste being prepared is tested for the property, test method and testing standard are as follows:
Tinting strength, tinting power test: it is surveyed according to chemical industry standard " HG/T 3951-2007 building coating aqueous color paste " Appendix B
It tries concrete application embodiment 9~12 and compares the relative color strength of 13~16 aqueous color paste of Application Example, with concrete application reality
It is standard mill base that the dispersing agent for applying the preparation of example 9, which is used for aqueous color paste,.
Stability test: by concrete application embodiment 9~12 and comparison 13~16 aqueous color paste of Application Example at 25 DEG C
After lower the closed placement of difference 30 days and 90 days, passing through visual observations, whether there is or not the serious shadows such as obvious granules of pigments precipitating, flocculation occur
The case where ringing stability is to judge storage stability of the dispersing agent for aqueous color paste.
Table 2 is that concrete application embodiment 9~12 and comparison 13~16 aqueous color paste of Application Example are surveyed according to the above method
The result of examination.Wherein in storage stability test, " √ " indicates that range estimation is without exception, and "×" indicates that obvious granules of pigments occurs in range estimation
Situations such as precipitating, flocculation.
The performance test results of 2 aqueous color paste of table
The above is only a preferred embodiment of the present invention, it is not intended to restrict the invention, it is noted that for this skill
For the those of ordinary skill in art field, without departing from the technical principles of the invention, can also make it is several improvement and
Modification, these improvements and modifications also should be regarded as protection scope of the present invention.
Claims (10)
1. a kind of preparation method of the waterborne pigment dispersant containing phenylethylene-maleic anhydride structure and graft modification, feature
It is, includes the following steps:
S1: the preparation of block copolymer solution: by four kinds of styrene, styrene derivative, maleic anhydride, acrylic acid derivative lists
Body and solvent are made into mixed solution and are placed in reactor, in the condition of inert gas shielding and temperature control at 70~100 DEG C
Under, the mixture that initiator, chain-transferring agent and solvent form is slowly added dropwise into reactor, the reaction was continued after completion of dropwise addition 1
~3h, obtains block copolymer solution；
S2: graft modification agent the preparation of graft modification block copolymer: is added in the block copolymer solution that step S1 is obtained
Graft reaction is carried out with catalyst, reaction temperature is 70~100 DEG C, and the reaction time is 2~6h, removes solvent simultaneously after reaction
It is cooled to room temperature, obtains graft modification block copolymer；
The styrene derivative is the compound with logical formula (I) structure:
Wherein, R1For H or methyl；R2For the alkyl containing carbon number between 1~10, contain 1 and 10；
The acrylic acid derivative is the compound with logical formula (II) structure:
Wherein, R3For H or methyl, R4To contain containing alkyl of the carbon number between 1~10 or the alkylol containing carbon number between 1~10
1 and 10；
The graft modification agent is the compound with logical formula (III) structure:
Wherein, R5、R6And R7For one of methyl, ethyl, methoxy or ethoxy, and R5、R6And R7Independently of each other；N is 1-
Integer between 10 contains 1 and 10.
2. preparation method according to claim 1, it is characterised in that: in step S1, with styrene, styrene derivative,
The gross mass meter of four kinds of monomers of maleic anhydride and acrylic acid derivative, styrene account for the 14%~27% of four kinds of monomer gross mass,
Styrene derivative accounts for the 28%~55% of four kinds of monomer gross mass, maleic anhydride account for four kinds of monomer gross mass 13%~
25%, acrylic acid derivative accounts for the 17%~38% of four kinds of monomer gross mass；Initiator account for four kinds of monomer gross mass 5%~
10%, chain-transferring agent accounts for the 3%~5% of four kinds of monomer gross mass.
3. preparation method according to claim 2, it is characterised in that: the initiator is azodiisobutyronitrile, azo two
In different heptonitrile, benzoyl peroxide, cumyl peroxide, the special butyl ester of peroxidating two and perbenzoic acid spy's butyl ester at least
It is a kind of.
4. preparation method according to claim 2, it is characterised in that: the chain-transferring agent is lauryl mercaptan or Alpha-Methyl benzene
Ethylene linear dimerization body.
5. preparation method according to claim 1, it is characterised in that: solvent described in step S1 be Isosorbide-5-Nitrae-dioxane,
One of thiacyclohexane, tetrahydrofuran and isopropanol.
6. preparation method according to claim 1, it is characterised in that: in step S2, the graft modification agent is 3- amino
Propyl front three oxosilane, 3-aminopropyltriethoxysilane, 3- dimethyl methoxy silane and 3- aminopropyl two
One of (ethoxymethyl) base silane.
7. preparation method according to claim 1, it is characterised in that: the quality of graft modification agent described in step S2 accounts for horse
Carry out the 40%~80% of acid anhydrides quality.
8. preparation method according to claim 1, it is characterised in that: catalyst described in step S2 be p-methyl benzenesulfonic acid,
One of alchlor, triethylamine, 4-dimethylaminopyridine and pyridine.
9. one kind prepares resulting structure containing phenylethylene-maleic anhydride with any claim preparation method in claim 1 to 8
And the waterborne pigment dispersant of graft modification.
10. a kind of application of the waterborne pigment dispersant described in claim 9 in water-based pigment colour paste.
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| CN111117375A (en) * | 2020-01-02 | 2020-05-08 | 传美讯电子科技（珠海）有限公司 | Color paste for water-based ink and preparation method thereof |
| CN111393569A (en) * | 2020-04-07 | 2020-07-10 | 嘉兴华雯化工有限公司 | Styrene maleic amide acid copolymer and preparation method thereof |
| CN111393569B (en) * | 2020-04-07 | 2021-11-05 | 嘉兴华雯化工股份有限公司 | Styrene maleic amide acid copolymer and preparation method thereof |
| CN112694554A (en) * | 2021-01-11 | 2021-04-23 | 浙江阿尔法化工科技有限公司 | Synthesis method and production equipment of SMA resin |
| CN113248722A (en) * | 2021-02-07 | 2021-08-13 | 中海油常州涂料化工研究院有限公司 | Novel styrene-maleic anhydride modified copolymer dispersant and preparation method thereof |
| CN113248722B (en) * | 2021-02-07 | 2022-06-21 | 中海油常州涂料化工研究院有限公司 | Styrene-maleic anhydride modified copolymer dispersant and preparation method thereof |
| CN114015245A (en) * | 2021-10-20 | 2022-02-08 | 鄂尔多斯市路泰公路工程有限责任公司 | Stable rubber powder polymer composite modified asphalt and mixture |
| CN114181340A (en) * | 2021-12-24 | 2022-03-15 | 苏州世名科技股份有限公司 | Modified styrene-maleic anhydride resin and preparation method and application thereof |
| CN114181340B (en) * | 2021-12-24 | 2024-01-05 | 苏州世名科技股份有限公司 | Modified styrene-maleic anhydride resin and preparation method and application thereof |
| CN114933669A (en) * | 2022-07-04 | 2022-08-23 | 宜兴市湖景化工有限公司 | Preparation method of dispersing force adjustable sodium polycarboxylate dispersant for rubber |
| CN117361951A (en) * | 2023-10-10 | 2024-01-09 | 浙江威克赛新材料科技有限公司 | Color asphalt concrete with good color stability and preparation method thereof |
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