CN106008963A - Polyoxamide powder and preparation method thereof - Google Patents
Polyoxamide powder and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a polyoxamide powder and a preparation method thereof. The preparation method comprises the following steps: carrying out atomization polymerization on diamine and oxalic acid diester, pulverizing, carrying out solid polymerization, and pulverizing. The preparation method comprises the following steps: (1) preparing a polyoxamide prepolymer; (2) pulverizing the prepolymer; (3) carrying out solid polymerization; and (4) pulverizing the polyoxamide. The polyoxamide powder has the advantages of regular shape and uniform particle size distribution, and can be used in the fields of 3D printing, paints, cosmetic packaging materials and the like. The preparation method has the advantages of no need of solvent consumption in the preparation process and low cost, and has favorable application prospects.
Description
Technical field
The invention belongs to polymeric material field, particularly to a kind of polyoxamide powder and preparation method thereof.
Background technology
Nylon powder i.e. polyamide powder, it is of a great variety, such as nylon 6, nylon66 fiber, nylon 1010, nylon 11, nylon
12 and modification of nylon powder etc..They all maintain the excellent properties of original nylon, have good mechanical performance and wearability,
Softening point is high, self-lubricating, and oil resistant and general chemicals, nontoxic, electrical insulating property is good, easily processes, is therefore widely used in powder
The fields such as end coating, filler, binding agent, medicine, cosmetics, 3D printing, become the most promising a kind of macromolecule material
Material.
In recent years, along with the development of 3D printing technique, nylon powder is more and more applied in 3D printing technique.
201410399560.9 disclose one by surfactant, light absorber, bulking agent, thinner, antioxidant and conductive powder etc.
Join nylon powder base material, obtain modification of nylon base material, modification of nylon base material, solvent naphtha and emulsifying agent are added in reactor,
Agitating heating rapidly cools to form nylon suspension after obtaining nylon high temperature emulsion, separating, washing, drying, sieve 30～100
The preparation method of the spherical nylon powder of μm.201410331489.0 disclose one nylon material, nucleator, ethanol to be put into
In autoclave, heated and stirred obtains nylon lysate, and cryoprecipitation separates out, and filters, centrifugation, vacuum drying, screening
Obtain the preparation method of 35～50 μm nylon powders.
, there is following common deficiency in 3D printing nylon powder and preparation method thereof disclosed in above-mentioned patent, have impact on it and promote
And application.
(1) needing to consume a large amount of solvent in preparation process, need Slow cooling in powder precipitation process, the production cycle is long, and last handling process is multiple
Miscellaneous, high cost.
(2) powder shape is irregular, and particle diameter skewness can not meet commercial Application to goods precision and the requirement of intensity.
Summary of the invention
The technical problem to be solved is to provide a kind of polyoxamide powder and preparation method thereof, this polyoxamide powder shape
State rule, even particle size distribution, may be used for the fields such as 3D printing, coating, toiletry bag package material；Nothing in preparation process
Solvent, low cost need to be consumed, have a good application prospect.
A kind of polyoxamide powder of the present invention, described polyoxamide powder be atomized by diamine and oxalate diester be polymerized, pulverize,
Solid phase, again pulverize and obtain.
Described polyoxamide contain the one in 2 methyl pentamethylenediamine unit M5, decamethylene diamine unit, dodecyl diamine unit or
Several.
Described polyoxamide is poly-oxalyl making methylpentamethylenediamine diamine NM52, poly-oxalyl decamethylene diamine N102 or poly-oxalyl dodecyl diamidogen
N122。
The mean diameter of described polyoxamide powder is 1～200 μm.Preferably, mean diameter is 10～60 μm.
The relative viscosity of described polyoxamide powder is between 2.0-4.0；The condition determination of relative viscosity is: with 96% sulphuric acid be
Solvent compound concentration is that the polyoxamide solution of 0.01g/mL measures at 25 DEG C.
Described polyoxamide powder is also added with white carbon or calcium carbonate, and addition is the 0.1～10% of polyoxamide quality.In preparation
Polyoxamide powder is mixed by Shi Liyong high-speed mixer with white carbon or calcium carbonate.
A kind of preparation method of the polyoxamide powder of the present invention, including:
(1) diamine and oxalate diester in mass ratio 0.1～1:0.1～1 are pumped in nozzle by the pump that feeds intake, respectively in inert gas
Carry out atomization polymerization, vacuum drying obtains polyoxamide prepolymer；
(2) prepolymer is carried out pulverizing and obtain prepolymer powder；
(3) at Tm-20 DEG C to Tm-5 DEG C, prepolymer powder under vacuo or is carried out solid phase under inert gas, is gathered
Oxamides high polymer powder；Wherein, Tm is the fusing point of polyoxamide；
(4) carry out further pulverizing i.e. obtaining polyoxamide powder by polyoxamide high polymer powder.
Diamine in described step (1) is one or more in 2 methyl pentamethylenediamine, decamethylene diamine, dodecyl diamidogen.Examine
Consider reactivity, it is preferred that described diamine is 2-methyl isophthalic acid, one or both in 5-1,5-DAP, decamethylene diamine.Consider
Water absorption rate, it is furthermore preferred that described diamine is decamethylene diamine.
Oxalate diester in described step (1) be dimethyl oxalate., ethyl oxalate, DPO, oxalic acid diisopropyl ester,
One or more in di-isobutyl oxalate, oxalic acid di tert butyl carbonate.Consider reactivity, it is preferred that described oxalate diester is grass
One or more in dimethyl phthalate, ethyl oxalate, DPO.Consider water absorption rate, it is furthermore preferred that described oxalic acid
Diester is dibutyl oxalate.
The noble gas that inert gas in described step (1) and (3) is used is helium, neon, argon, Krypton, xenon
Gas, nitrogen or carbon dioxide；It is preferably nitrogen.The flow velocity of inert gas is 1-15m3/h；It is preferably 2-10m3/ h, more preferably
For 3-5m3/h。
Solid phase polymerization temperature in described step (3) is 150-250 DEG C, and solid state polymerization time is 3-24h, solid phase vacuum
Degree is 200-500Mpa.
Beneficial effect
The polyoxamide powder morphology rule of the present invention, even particle size distribution, may be used for 3D printing, coating, toiletry bag
The fields such as package material；Without consuming solvent in preparation process, low cost, have a good application prospect.
Accompanying drawing explanation
Fig. 1 is the atomization polyplant schematic diagram that the present invention prepares polyoxamide powder；
Fig. 2 is the electron scanning imaging figure that the present invention prepares polyoxamide powder.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is expanded on further.Should be understood that these embodiments be merely to illustrate the present invention and not
For limiting the scope of the present invention.In addition, it is to be understood that after having read the content that the present invention lectures, those skilled in the art can
To make various changes or modifications the present invention, these equivalent form of values fall within the application appended claims limited range equally.
Raw material:
Dibutyl oxalate (> 99.0%, TCI, CAS 2050-60-4)；
2-methyl isophthalic acid, 5-1,5-DAP (> 98.0%, TCI, CAS 15520-10-2)；
Dodecyl diamidogen (> 97.0%, Sigma-Aldrich, CAS 112-18-5)；
Decamethylene diamine (> 97.0%, TCI, CAS 646-25-3)；
Equipment and instrument:
Use Baoding LanGe constant flow pump Co., Ltd's LSP01-1A syringe pump.
Embodiment 1
Dibutyl oxalate monomer (202.25g) and decamethylene diamine monomer (177.49g) are pumped in nozzle at 3m by the pump that feeds intake respectively3/h
Stream of nitrogen gas in carry out atomization polymerization, atomization polymerization time is 22.15min, is vacuum dried to obtain N102 prepolymer, utilizes powder
N102 prepolymer is carried out pulverizing and obtains prepolymer powder by broken machine, by aforesaid prepolymer powder at 3m3The stream of nitrogen gas of/h is entered
Row solid phase, solid phase polymerization temperature is 150 DEG C, and solid state polymerization time is 3h, and solid phase vacuum is 200Mpa,
N102 high polymer powder, utilizes pulverizer to be pulverized further by N102 high polymer powder and obtains N102 powder, and mean diameter is
180.5 μm, it is 250 DEG C that DSC measures fusing point.
Embodiment 2
Dibutyl oxalate monomer (202.25g) and decamethylene diamine monomer (177.49g) are pumped in nozzle at 4m by the pump that feeds intake respectively3/h
Stream of nitrogen gas in carry out atomization polymerization, atomization polymerization time is 22.15min, is vacuum dried to obtain N102 prepolymer, utilizes powder
N102 prepolymer is carried out pulverizing and obtains prepolymer powder by broken machine, by aforesaid prepolymer powder at 4m3The stream of nitrogen gas of/h is entered
Row solid phase, solid phase polymerization temperature is 170 DEG C, and solid state polymerization time is 5h, and solid phase vacuum is 220Mpa,
N102 high polymer powder, utilizes pulverizer to be pulverized further by N102 high polymer powder and obtains N102 powder, before 100g
High-speed mixer mixing put into by the N102 powder stated and 0.5g white carbon, and stirring, to mix homogeneously, obtains the mixing of N102/ white carbon
Thing powder, mean diameter is 140.2 μm, and it is 250.1 DEG C that DSC measures fusing point.
Embodiment 3
Dibutyl oxalate monomer (202.25g) and decamethylene diamine monomer (177.49g) are pumped in nozzle at 5m by the pump that feeds intake respectively3/h
Stream of nitrogen gas in carry out atomization polymerization, atomization polymerization time is 22.15min, is vacuum dried to obtain N102 prepolymer, utilizes powder
N102 prepolymer is carried out pulverizing and obtains prepolymer powder by broken machine, by aforesaid prepolymer powder at 5m3The stream of nitrogen gas of/h is entered
Row solid phase, solid phase polymerization temperature is 180 DEG C, and solid state polymerization time is 8h, and solid phase vacuum is 250Mpa,
N102 high polymer powder, utilizes pulverizer to be pulverized further by N102 high polymer powder and obtains N102 powder, before 100g
High-speed mixer mixing put into by the N102 powder stated and 1g white carbon, and stirring, to mix homogeneously, obtains N102/ white carbon mixture
Powder, mean diameter is 100.1 μm, and it is 250.4 DEG C that DSC measures fusing point.
Embodiment 4
Dibutyl oxalate monomer (202.25g) and decamethylene diamine monomer (177.49g) are pumped in nozzle at 3m by the pump that feeds intake respectively3/h
Stream of nitrogen gas in carry out atomization polymerization, atomization polymerization time is 22.15min, utilizes pulverizer that N102 prepolymer is carried out powder
Broken obtain prepolymer powder, by aforesaid prepolymer powder at 3m3The stream of nitrogen gas of/h carries out solid phase, solid phase temperature
Degree is 200 DEG C, and solid state polymerization time is 10h, and solid phase vacuum is 200Mpa, obtains N102 high polymer powder, utilizes
N102 high polymer powder is pulverized and is obtained N102 powder by pulverizer further, by white to aforesaid for 100g N102 powder and 2.5g
White carbon black puts into high-speed mixer mixing, and stirring, to mix homogeneously, obtains N102/ white carbon mix powder, and mean diameter is 50.2 μm,
It is 251 DEG C that DSC measures fusing point.
Embodiment 5
Dibutyl oxalate monomer (202.25g) and decamethylene diamine monomer (177.49g) are pumped in nozzle at 3m by the pump that feeds intake respectively3/h
Stream of nitrogen gas in carry out atomization polymerization, atomization polymerization time is 22.15min, is vacuum dried to obtain N102 prepolymer, utilizes powder
N102 prepolymer is carried out pulverizing and obtains prepolymer powder by broken machine, by aforesaid prepolymer powder at 3m3The stream of nitrogen gas of/h is entered
Row solid phase, solid phase polymerization temperature is 230 DEG C, and solid state polymerization time is 16h, and solid phase vacuum is 400Mpa,
N102 high polymer powder, utilizes pulverizer to be pulverized further by N102 high polymer powder and obtains N102 powder, before 100g
High-speed mixer mixing put into by the N102 powder stated and 5g white carbon, and stirring, to mix homogeneously, obtains N102/ white carbon mixture
Powder, mean diameter is 11.2 μm, and it is 251.2 DEG C that DSC measures fusing point.
Embodiment 6
Dibutyl oxalate monomer (202.25g) and decamethylene diamine monomer (177.49g) are pumped in nozzle by the pump that feeds intake respectively and carries out
3m3Atomization polymerization in the stream of nitrogen gas of/h, atomization polymerization time is 22.15min, is vacuum dried to obtain N102 prepolymer, utilizes powder
N102 prepolymer is carried out pulverizing and obtains prepolymer powder by broken machine, carries out aforesaid prepolymer powder at 3m3The stream of nitrogen gas of/h
Middle solid phase, solid phase polymerization temperature is 250 DEG C, and solid state polymerization time is 24h, and solid phase vacuum is 500Mpa,
N102 high polymer powder, utilizes pulverizer to be pulverized further by N102 high polymer powder and obtains N102 powder, before 100g
High-speed mixer mixing put into by the N102 powder stated and 10g white carbon, and stirring, to mix homogeneously, obtains the mixing of N102/ white carbon
Thing powder, mean diameter is 5.2 μm, and it is 251.6 DEG C that DSC measures fusing point.
Embodiment 7
Dibutyl oxalate monomer (202.25g) and decamethylene diamine monomer (177.49g) are pumped in nozzle by the pump that feeds intake respectively and carries out
3m3Atomization polymerization in the stream of nitrogen gas of/h, atomization polymerization time is 22.15min, is vacuum dried to obtain N102 prepolymer, utilizes powder
N102 prepolymer is carried out pulverizing and obtains prepolymer powder by broken machine, by aforesaid prepolymer powder at 3m3The stream of nitrogen gas of/h is entered
Row solid phase, solid phase polymerization temperature is 190 DEG C, and solid state polymerization time is 6h, and solid phase vacuum is 240Mpa,
N102 high polymer powder, utilizes pulverizer to be pulverized further by N102 high polymer powder and obtains N102 powder, before 100g
The N102 powder stated and 10g calcium carbonate put into high-speed mixer mixing, and stirring, to mix homogeneously, obtains the mixing of N102/ calcium carbonate
Thing powder, mean diameter is 5.1 μm, and it is 251.5 DEG C that DSC measures fusing point.
Embodiment 8
By dibutyl oxalate monomer (202.25g) and dodecyl diamine monomer (249.69g) respectively by the pump that feeds intake pump in nozzle
3m3Carrying out atomization polymerization in the stream of nitrogen gas of/h, atomization polymerization time is 22.15min, is vacuum dried to obtain N122 prepolymer, profit
With pulverizer, N122 prepolymer is carried out pulverizing and obtain prepolymer powder, by aforesaid prepolymer powder at 3m3The stream of nitrogen gas of/h
In carry out solid phase, solid phase polymerization temperature is 220 DEG C, and solid state polymerization time is 20h, and solid phase vacuum is 350Mpa,
Obtain N122 high polymer powder, utilize pulverizer to be pulverized further by N122 high polymer powder and obtain N122 powder, by 100g
High-speed mixer mixing put into by aforesaid N122 powder and 10g white carbon, and stirring, to mix homogeneously, obtains N122/ white carbon and mixes
Compound powder, mean diameter is 6.1 μm, and it is 235 DEG C that DSC measures fusing point.
Embodiment 9
By dibutyl oxalate monomer (202.25g) and 2-methyl isophthalic acid, 5-1,5-DAP monomer (119.70g) is pumped into by the pump that feeds intake respectively
At 3m in nozzle3Carrying out atomization polymerization in the stream of nitrogen gas of/h, atomization polymerization time is 22.15min, is vacuum dried to obtain NM52
Prepolymer, utilizes pulverizer that NM52 prepolymer is carried out pulverizing and obtains prepolymer powder, by aforesaid prepolymer powder at 3m3/h
Stream of nitrogen gas in carry out solid phase, solid phase polymerization temperature is 150 DEG C, and solid state polymerization time is 8h, solid phase vacuum
For 300Mpa, obtain NM52 high polymer powder, utilize pulverizer to be pulverized further by NM52 high polymer powder and obtain NM52
Powder, puts into high-speed mixer mixing by aforesaid for 100g N122 powder and 10g white carbon, and stirring, to mix homogeneously, obtains
NM52/ white carbon mix powder, mean diameter is 4.9 μm, and it is 200 DEG C that DSC measures fusing point.
Embodiment 10
By dibutyl oxalate monomer (202.25g) and dodecyl diamidogen: decamethylene diamine (0.3:0.7) (233.27g) is respectively by the pump pump that feeds intake
Enter in nozzle at 3m3Carrying out atomization polymerization in the stream of nitrogen gas of/h, atomization polymerization time is 22.15min, is vacuum dried
N122/N102 prepolymer, utilizes pulverizer that N122/N102 prepolymer is carried out pulverizing and obtains prepolymer powder, by aforesaid pre-
Copolymer powder is at 3m3Carrying out solid phase in the stream of nitrogen gas of/h, solid phase polymerization temperature is 160 DEG C, and solid state polymerization time is 4h,
Solid phase vacuum is 210Mpa, obtains N122/N102 high polymer powder, utilizes pulverizer by N122/N102 high polymer powder
End is pulverized further and is obtained N122/N102 powder, aforesaid for 100g N122/N102 powder and 10g white carbon is put at a high speed
Mixer mixes, and stirring, to mix homogeneously, obtains N122/N102/ white carbon mix powder, and mean diameter is 5.8 μm, DSC
Mensuration fusing point is 240C.
Embodiment 11
By dibutyl oxalate monomer (202.25g) and 2-methyl isophthalic acid, 5-1,5-DAP: dodecyl diamidogen (0.3:0.7) (215.94g) point
Do not pumped in nozzle at 3m by the pump that feeds intake3Carrying out atomization polymerization in the stream of nitrogen gas of/h, atomization polymerization time is 22.15min,
It is vacuum dried to obtain NM52/N122 prepolymer, utilizes pulverizer that NM52/N122 prepolymer is carried out pulverizing and obtain prepolymer powder,
By aforesaid prepolymer powder at 3m3Carrying out solid phase in the stream of nitrogen gas of/h, solid phase polymerization temperature is 210 DEG C, solid phase
Time is 8h, and solid phase vacuum is 290Mpa, obtains NM52/N122 high polymer powder, utilizes pulverizer by NM52/N122
High polymer powder is pulverized further and is obtained NM52/N122 powder, by aforesaid for 100g NM52/N122 powder and 10g Linesless charcoal
Black high-speed mixer of putting into mixes, and stirring, to mix homogeneously, obtains NM52/N122/ white carbon mix powder, and mean diameter is
5.5 μm, it is 220 DEG C that DSC measures fusing point.
Embodiment 12
By dibutyl oxalate monomer (202.25g) and 2-methyl isophthalic acid, 5-1,5-DAP: decamethylene diamine (0.3:0.7) (160.15g) passes through respectively
The pump that feeds intake pumps in nozzle at 3m3Carrying out atomization polymerization in the stream of nitrogen gas of/h, atomization polymerization time is 22.15min, and vacuum is done
Dry NM52/N102 prepolymer, utilizes pulverizer that NM52/N102 prepolymer is carried out pulverizing and obtains prepolymer powder, by front
The prepolymer powder stated is at 3m3Carrying out solid phase in the stream of nitrogen gas of/h, solid phase polymerization temperature is 230 DEG C, solid state polymerization time
For 15h, solid phase vacuum is 450Mpa, obtains NM52/N102 high polymer powder, utilizes pulverizer by NM52/N102
High polymer powder is pulverized further and is obtained NM52/N102 powder, by aforesaid for 100g NM52/N102 powder and 10g Linesless charcoal
Black high-speed mixer of putting into mixes, and stirring, to mix homogeneously, obtains NM52/N102/ white carbon mix powder, and mean diameter is
5.3 μm, it is 222 DEG C that DSC measures fusing point.
The product powder diameter of the polyoxamide of embodiment 1-12 and shape are as shown in table 1.
Table 1
From Fig. 1, Fig. 2 and Biao 1, using the polyoxamide powder that this method polymerization prepares, powder diameter is controlled, particle diameter
It is evenly distributed, meets the commercial Application requirement to goods precision.
Claims (10)
1. a polyoxamide powder, it is characterised in that: described polyoxamide powder is polymerized with oxalate diester atomization by diamine, powder
Broken, solid phase, pulverize again and obtain.
A kind of polyoxamide powder the most according to claim 1, it is characterised in that: described polyoxamide contains 2 methyl pentamethylenediamine
One or more in unit M5, decamethylene diamine unit, dodecyl diamine unit.
A kind of polyoxamide powder the most according to claim 1 and 2, it is characterised in that: described polyoxamide is poly-oxalyl methyl
Pentanediamine NM52, poly-oxalyl decamethylene diamine N102 or poly-oxalyl dodecyl diamidogen N122.
A kind of polyoxamide powder the most according to claim 1, it is characterised in that: the mean diameter of described polyoxamide powder is
1～200 μm.
A kind of polyoxamide powder the most according to claim 1, it is characterised in that: described polyoxamide powder is also added with white carbon
Or calcium carbonate, addition is the 0.1～10% of polyoxamide quality.
6. a preparation method for polyoxamide powder, including:
(1) diamine and oxalate diester in mass ratio 0.1～1:0.1～1 are pumped in nozzle by the pump that feeds intake, respectively in inert gas
Carry out atomization polymerization, vacuum drying obtains polyoxamide prepolymer；
(2) prepolymer is carried out pulverizing and obtain prepolymer powder；
(3) at Tm-20 DEG C to Tm-5 DEG C, prepolymer powder under vacuo or is carried out solid phase under inert gas, is gathered
Oxamides high polymer powder；Wherein, Tm is the fusing point of polyoxamide；
(4) carry out further pulverizing i.e. obtaining polyoxamide powder by polyoxamide high polymer powder.
The preparation method of a kind of polyoxamide powder the most according to claim 6, it is characterised in that: in described step (1)
Diamine is one or more in 2 methyl pentamethylenediamine, decamethylene diamine, dodecyl diamidogen.
The preparation method of a kind of polyoxamide powder the most according to claim 6, it is characterised in that: in described step (1)
Oxalate diester is dimethyl oxalate., ethyl oxalate, DPO, oxalic acid diisopropyl ester, di-isobutyl oxalate, oxalic acid
One or more in di tert butyl carbonate.
The preparation method of a kind of polyoxamide powder the most according to claim 6, it is characterised in that: described step (1) and (3)
In the noble gas that used of inert gas be helium, neon, argon, Krypton, xenon, nitrogen or carbon dioxide；Inertia
The flow velocity of air-flow is 1-15m3/h。
The preparation method of a kind of polyoxamide powder the most according to claim 6, it is characterised in that: in described step (3)
Solid phase polymerization temperature is 150-250 DEG C, and solid state polymerization time is 3-24h, and solid phase vacuum is 200-500Mpa.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111495312A (en) * | 2020-05-22 | 2020-08-07 | 河南心连心化学工业集团股份有限公司 | Synthetic device and synthetic method for oxamide |
| WO2021213833A1 (en) * | 2020-04-22 | 2021-10-28 | Agfa Nv | Aqueous resin particle dispersion |
| CN115427522B (en) * | 2020-04-22 | 2024-05-28 | 爱克发有限公司 | Aqueous resin particle dispersion |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103421185A (en) * | 2012-05-22 | 2013-12-04 | 东丽先端材料研究开发（中国）有限公司 | Aliphatic polyamide resin and use thereof |
| CN105461919A (en) * | 2016-01-06 | 2016-04-06 | 东华大学 | Atomization and polymerization method and device of polyoxamide |
-
2016
- 2016-06-29 CN CN201610494313.6A patent/CN106008963A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103421185A (en) * | 2012-05-22 | 2013-12-04 | 东丽先端材料研究开发（中国）有限公司 | Aliphatic polyamide resin and use thereof |
| CN105461919A (en) * | 2016-01-06 | 2016-04-06 | 东华大学 | Atomization and polymerization method and device of polyoxamide |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021213833A1 (en) * | 2020-04-22 | 2021-10-28 | Agfa Nv | Aqueous resin particle dispersion |
| CN115427522A (en) * | 2020-04-22 | 2022-12-02 | 爱克发有限公司 | Aqueous resin particle dispersion |
| CN115427522B (en) * | 2020-04-22 | 2024-05-28 | 爱克发有限公司 | Aqueous resin particle dispersion |
| CN111495312A (en) * | 2020-05-22 | 2020-08-07 | 河南心连心化学工业集团股份有限公司 | Synthetic device and synthetic method for oxamide |
| CN111495312B (en) * | 2020-05-22 | 2023-07-28 | 河南心连心化学工业集团股份有限公司 | Oxamide synthesis device and synthesis method |
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