CN105601861A - Synthetic method for organosilicone modified waterborne polyurethane resin - Google Patents
Synthetic method for organosilicone modified waterborne polyurethane resin Download PDFInfo
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- CN105601861A CN105601861A CN201610099024.6A CN201610099024A CN105601861A CN 105601861 A CN105601861 A CN 105601861A CN 201610099024 A CN201610099024 A CN 201610099024A CN 105601861 A CN105601861 A CN 105601861A
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6644—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6648—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6651—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6662—Compounds of group C08G18/42 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a synthetic method for organosilicone modified waterborne polyurethane resin. The synthetic method comprises the specific steps that firstly, polyester polyol Novomer is subjected to vacuum dehydration, diisocyanate is added dropwise, and a polyurethane prepolymer I is obtained after a reaction; secondly, polyhydroxy carboxylic acid is added to the polyurethane prepolymer I, a dihydric alcohol monomer is added dropwise, and a polyurethane prepolymer II is obtained after a reaction; thirdly, trimethylolpropane is added to the polyurethane prepolymer II, and a polyurethane prepolymer is obtained after a reaction; fourthly, organic amine is added to the polyurethane prepolymer for a salt forming reaction, a silane coupling agent, deionized water and diamine are sequentially added for chain extension and stirring, and the organosilicone modified waterborne polyurethane resin with high hardness is obtained after emulsification. The synthetic method has the advantages that the hardness of the organosilicone modified waterborne polyurethane resin reaches 3H, the adhesive force is good, and stability is good.
Description
Technical field
The present invention relates to a kind of resin synthetic method, be specifically related to the synthetic of a kind of organosilicon modified aqueous polyurethane resinMethod.
Background technology
In the application of coating, because polyurethane resin has excellent chemical property and more comprehensive mechanical-physicalPerformance, after solidifying, its film has good wearability and chemical moral character, be usually used in anti-corrosion of metal, painting dressing automobiles, aircraft skin,Floor paint, traffic paint etc. But, the free isocyanic acid that most of polyurethane coatings contain more organic solvent and someEster has therefore affected environment and people's health in construction and application process. Aqueous polyurethane is taking water as decentralized medium, withSolvent borne polyurethane is compared, have do not fire, smell is little, the advantage such as nontoxic, pollution-free, energy-conservation, easy to operate, is extensively used as skinLeather finishing agent, textile auxiliary, paper industry auxiliary agent, coating and adhesive etc., and application is also in continuous expansion.
The lower hardness of film forming after the synthetic ubiquity of current single-component water-based polyurethane resin is dry, lower than 1H or exert oneselfReach by force 1H, reach on the market of 2H and almost do not have, and high rigidity can affect the adhesive force of resin on base material. Some plastic cementThe waterborne polyurethane resin of the use such as paint, woodcare paint, metallic paint require hardness of paint film 2H or more than, double-component waterborne polyurethane resinHardness can meet the demands, but need now with the current, life cycle is short, toos many or too much for use and has just wasted, very inconvenient, so haveA one-component high rigidity waterborne polyurethane resin of necessary exploitation is taken into account the adhesive force to base material simultaneously.
Summary of the invention
The present invention seeks to: one is provided, and not only preparation method is simple, and hardness is high, strong adhesion, good stabilityThe synthetic method of organosilicon modified aqueous polyurethane resin.
Technical scheme of the present invention is: a kind of synthetic method of organosilicon modified aqueous polyurethane resin, comprises following toolBody step:
Step 1) PEPA Novomer is added to reaction vessel, after vacuum dehydration, by temperature control in reaction vesselAt 80～90 DEG C, then in stirring downhill reaction container, drip vulcabond, wherein vulcabond and polyester are manyThe mol ratio of the alcohol Novomer of unit is 2～4:1, after dropwising, 80～90 DEG C of reactions 2～3 hours, obtains base polyurethane prepolymer for use asI；
Step 2) by step 1) the base polyurethane prepolymer for use as I that obtains cools to below 60 DEG C, by straight dry multi-hydroxy carboxy acidConnect to add or be dissolved in 1-METHYLPYRROLIDONE and join reaction vessel, then in reaction vessel, drip dihydroxylic alcohols monomer,Time for adding 0.5～1 hour, after dropwising, then is warmed up to 70～80 DEG C, reacts 2.5～3.5 hours, in course of reaction, addsEnter diluent, after reaction finishes, obtain the base polyurethane prepolymer for use as II containing hydrophilic radical;
Step 3) by step 2) the base polyurethane prepolymer for use as II that obtains cools to below 65 DEG C, adds trimethylolpropane, temperatureDegree is controlled at 65～70 DEG C, reacts 1～1.5 hour, obtains polyurethane prepolymer;
Step 4) by step 3) polyurethane prepolymer that obtains cools to below 50 DEG C, under stirring, adds organic amineIn and salify, organic amine and multi-hydroxy carboxy acid's mol ratio are 1:1, then add silane coupler, stirring reaction 30～60mins, thenAdd deionized water, add afterwards diamine again, stir 30～60mins, it is that 30～45% organosilicon changes that emulsification obtains solid contentWaterborne polyurethane resin.
As preferred technical scheme, described vulcabond is selected from toluene di-isocyanate(TDI), 4,4-diphenyl methane twoIsocyanates, IPDI, hexamethylene diisocyanate, ring penta vulcabond or hydrogenation of benzene methylmethane twoIsocyanates.
As preferred technical scheme, the mol ratio 1.1～1.8:1 of described vulcabond and hydroxyl total amount, wherein hydroxylBase is from PEPA Novomer, dihydroxylic alcohols, multi-hydroxy carboxy acid, trimethylolpropane.
As preferred technical scheme, the molecular weight of described PEPA Novomer is 1000～2000.
As preferred technical scheme, described multi-hydroxy carboxy acid is selected from dihydromethyl propionic acid or dimethylolpropionic acid, whereinCarboxyl in multi-hydroxy carboxy acid accounts for vulcabond, PEPA Novomer, dihydroxylic alcohols monomer, trimethylolpropane, binaryThe mass percent of amine, silane coupler gross weight is 2～7%.
As preferred technical scheme, described dihydroxylic alcohols monomer is selected from BDO, 1,3-BDO, a contracting diethyl twoAlcohol, propane diols, methyl propanediol, 1,6-hexylene glycol or neopentyl glycol.
As preferred technical scheme, described organic amine is selected from triethylamine or N, N-dimethylethanolamine.
As preferred technical scheme, described silane coupler is selected from KH550, KH602 or KH792.
As preferred technical scheme, described diamine is selected from ethylenediamine, hexamethylene diamine or IPD.
Advantage of the present invention is:
1. the present invention, by the selection of proportioning, reaction time, charging sequence and the reaction monomers of control reaction mass, has madeMachine silicone modified waterborne polyurethane resin has high hardness and good adhesive force, and storage stability is good, 1 year storage life withUpper, concrete advantage is as follows:
(1) by controlling charging sequence and the charging process of main material, the first step adopts vulcabond to drip polyesterThe method of polyalcohol Novomer, ensures that in course of reaction, PEPA Novomer is excessive, and controls dividing of product with thisMinor structure, second step is introduced hydrophilic radical carboxyl and chain extender dihydroxylic alcohols, and wherein the time for adding of dihydroxylic alcohols is controlled at 0.5～1Hour, to prevent that dihydroxylic alcohols from reacting with vulcabond group the temperature acutely causing and rising sharply, the 3rd step is introduced internal crosslinker threeHydroxymethyl-propane can add appropriate diluent (acetone) as required in reactant liquor, stirs to prevent that reactant liquor viscosity from raisingInequality, even pole-climbing gel; Obtain molecular structure control better, the product of excellent combination property, and mature production technology is stable;
(2) by selecting PEPA Novomer to be used as polyurethane molecular main chain, obtain the hardness ratio of productHigh;
(3), by controlling carboxyl-content and the distribution of carboxyl on molecular backbone, make the synthetic resin can be uniformBe scattered in water, and can store for a long time;
(4) add the amount of dihydroxylic alcohols monomer by control, in the situation that other main material proportionings are constant, regulate organosiliconContent to specified scope, thereby improve the adhesive force of product;
(5) by controlling the proportioning of PEPA Novomer and vulcabond, soft chain segment and hard in Molecular regulator chainThe proportioning of segment, when making synthetic resin meet high rigidity, again can some pliability;
(6) by controlling reaction temperature and the time in each stage, synthesis technique is stable, and resin property is stable;
(7), by adding organic amine to be neutralized into reactant salt, product is had splendid water-soluble;
(8) use diamine chain extension adding after deionized water, to prevent that amine from reacting and acutely causing viscosity to rise sharply with isocyano,Pole-climbing gel;
Final resin outward appearance is translucent light blue emulsion; Solid content is 30～45%; Water-soluble fine, available water is rareRelease; Final one-tenth film hardness reaches 3H, and adhesive force is good, is 0 grade; Storage stability is good, and 5～30 DEG C of storage times are greater than 1 year.
Detailed description of the invention
Embodiment 1:
Prepare according to the following steps one-component hard organosilicon modified aqueous polyurethane resin:
Be equipped with raw material:
| Raw material | Consumption (% weight) |
| 2,4-toluene di-isocyanate(TDI) | 32.8 |
| PEPA Novomer (molecular weight 1000) | 43.5 |
| Dihydromethyl propionic acid | 5.9 |
| Methyl propanediol | 3.4 |
| Trimethylolpropane | 4.9 |
| Triethylamine | 4.5 |
| KH550 | 5 |
Appropriate water, acetone, the 1-METHYLPYRROLIDONE of another outfit;
PEPA Novomer molecular weight is about 1000, and carboxyl-content is about 3%, and silicone content is about 1%, rubsYour proportioning is as follows: 2,4-toluene di-isocyanate(TDI): PEPA Novomer: dihydromethyl propionic acid: methyl propanediol: three hydroxylsMethylpropane: triethylamine: KH550 is about 3.8:1.0:1.0:0.8:1.2:1.0:1.3.
The resin outward appearance making is translucent micro-yellow emulsion, and solid content is in 36% left and right, and stability of emulsion is good, hardness3H, 0 grade of adhesive force.
Embodiment 2
Prepare according to the following steps one-component hard organosilicon modified aqueous polyurethane resin:
Be equipped with raw material:
| Raw material | Consumption (% weight) |
| IPDI | 33.6 |
| PEPA Novomer (molecular weight 1000) | 43.5 |
| Dihydromethyl propionic acid | 5.9 |
| Neopentyl glycol | 5.5 |
| Trimethylolpropane | 2.6 |
| Triethylamine | 4.5 |
| KH550 | 3 |
| Ethylenediamine | 1.4 |
Appropriate water, acetone, the 1-METHYLPYRROLIDONE of another outfit;
PEPA Novomer molecular weight is about 1000, and carboxyl-content is about 4.2%, and silicone content is about1.2%, mole proportioning is as follows: IPDI: PEPA Novomer: dihydromethyl propionic acid: new penta 2Alcohol: trimethylolpropane: triethylamine: KH550: ethylenediamine is about 3.6:1.0:1.0:0.8:1.2:1.0:1.3:0.3.
The resin outward appearance making is translucent light blue emulsion, and solid content is in 39% left and right, and stability of emulsion is good, hardness3H, 0 grade of adhesive force.
Embodiment 3
Prepare according to the following steps one-component hard organosilicon modified aqueous polyurethane resin:
Be equipped with raw material:
| Raw material | Consumption (% weight) |
| IPDI | 35.2 |
| PEPA Novomer (molecular weight 2000) | 40.3 |
| Dihydromethyl propionic acid | 6.5 |
| BDO | 4.6 |
| Trimethylolpropane | 2.6 |
| Triethylamine | 5 |
| KH602 | 3 |
| IPD | 2.8 |
Appropriate water, acetone, the 1-METHYLPYRROLIDONE of another outfit;
PEPA Novomer molecular weight is about 2000, and carboxyl-content is about 5.1%, and silicone content is about1.7%, mole proportioning is as follows: IPDI: PEPA Novomer: dihydromethyl propionic acid: Isosorbide-5-Nitrae-Ding bis-Alcohol: trimethylolpropane: triethylamine: KH602: IPD is about 3.8:1.0:1.0:1.5:1.2:1.0:1.3:0.7.
The resin outward appearance making is translucent light blue emulsion, and solid content is in 40% left and right, and stability of emulsion is good, hardness3H, 0 grade of adhesive force.
Above-described embodiment is illustrative principle of the present invention and effect thereof only, but not for limiting the present invention. Any ripeThe personage who knows this technology all can, under spirit of the present invention and category, modify or change above-described embodiment. CauseThis, have in technical field under such as conventionally know the knowledgeable do not depart under disclosed spirit and technological thought completeAll equivalences that become are modified or change, and must be contained by claim of the present invention.
Claims (9)
1. a synthetic method for organosilicon modified aqueous polyurethane resin, is characterized in that, comprises following concrete steps:
PEPA Novomer is added reaction vessel by step 1), after vacuum dehydration, temperature in reaction vessel is controlled to 80~ 90 DEG C, then in stirring downhill reaction container, drip vulcabond, wherein vulcabond and PEPAThe mol ratio of Novomer is 2 ~ 4:1, after dropwising, 80 ~ 90 DEG C of reactions 2 ~ 3 hours, obtains base polyurethane prepolymer for use as I;
Step 2) base polyurethane prepolymer for use as I that step 1) is obtained cools to below 60 DEG C, dry multi-hydroxy carboxy acid directly addedEnter or be dissolved in 1-METHYLPYRROLIDONE to join reaction vessel, then in reaction vessel, drip dihydroxylic alcohols monomer, drip0.5 ~ 1 hour time, after dropwising, then is warmed up to 70 ~ 80 DEG C, reacts 2.5 ~ 3.5 hours, adds dilution in course of reactionAgent, obtains the base polyurethane prepolymer for use as containing hydrophilic radical after reaction finishes；
Step 3) is by step 2) base polyurethane prepolymer for use as that obtainsCool to below 65 DEG C, add trimethylolpropane, temperature controlAt 65 ~ 70 DEG C, react 1 ~ 1.5 hour, obtain polyurethane prepolymer;
The polyurethane prepolymer that step 4) obtains step 3) cools to below 50 DEG C, adds organic amine neutralization under stirringSalify, organic amine and multi-hydroxy carboxy acid's mol ratio are 1:1, then add silane coupler, stirring reaction 30 ~ 60mins, then addDeionized water, adds diamine afterwards again, stir 30 ~ 60mins, emulsification obtain solid content be 30 ~ 45% organic silicon modified aqueousPolyurethane resin.
2. the synthetic method of organosilicon modified aqueous polyurethane resin according to claim 1, is characterized in that, described twoIsocyanates is selected from toluene di-isocyanate(TDI), 4,4-methyl diphenylene diisocyanate, IPDI, six methylenesGroup diisocyanate, ring penta vulcabond or hydrogenation methylenebis phenyl isocyanate.
3. the synthetic method of organosilicon modified aqueous polyurethane resin according to claim 1, is characterized in that, described twoMol ratio 1.1 ~ the 1.8:1 of isocyanates and hydroxyl total amount, wherein hydroxyl is from PEPA Novomer, dihydroxylic alcohols, many hydroxylsYl carboxylic acid, trimethylolpropane.
4. the synthetic method of organosilicon modified aqueous polyurethane resin according to claim 1, is characterized in that, described poly-The molecular weight of ester polyol Novomer is 1000 ~ 2000.
5. the synthetic method of organosilicon modified aqueous polyurethane resin according to claim 1, is characterized in that, described manyHydroxycarboxylic acid is selected from dihydromethyl propionic acid or dimethylolpropionic acid, and wherein the carboxyl in multi-hydroxy carboxy acid accounts for vulcabond, poly-The mass percent of ester polyol Novomer, dihydroxylic alcohols monomer, trimethylolpropane, diamine, silane coupler gross weight is 2 ~7%。
6. the synthetic method of organosilicon modified aqueous polyurethane resin according to claim 1, is characterized in that, described twoUnit alcohol monomer be selected from BDO, 1,3-BDO, diglycol, propane diols, methyl propanediol, 1,6-hexylene glycol orNeopentyl glycol.
7. the synthetic method of organosilicon modified aqueous polyurethane resin according to claim 1, is characterized in that, described in haveMachine amine is selected from triethylamine or N, N-dimethylethanolamine.
8. the synthetic method of organosilicon modified aqueous polyurethane resin according to claim 1, is characterized in that, described siliconAlkane coupling agent is selected from KH550, KH602 or KH792.
9. the synthetic method of organosilicon modified aqueous polyurethane resin according to claim 1, is characterized in that, described twoUnit's amine is selected from ethylenediamine, hexamethylene diamine or IPD.
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| CN106008895A (en) * | 2016-06-22 | 2016-10-12 | 合肥科天水性科技有限责任公司 | Anionic waterborne polyurethane resin for wood lacquer and preparation method of anionic waterborne polyurethane resin |
| CN106117451A (en) * | 2016-07-29 | 2016-11-16 | 同光（江苏）新材料科技有限公司 | A kind of preparation method of acrylic ester grafted modified aqueous polyurethane resin |
| CN107868202A (en) * | 2017-12-15 | 2018-04-03 | 黔南民族师范学院 | A kind of preparation method of organic-silicon-modified antibacterial aqueous polyurethane |
| CN109252387A (en) * | 2018-08-01 | 2019-01-22 | 四川大学 | A kind of leather/synthetic leather and preparation method thereof based on selfreparing aqueous polyurethane |
| CN109252387B (en) * | 2018-08-01 | 2021-03-30 | 四川大学 | Leather/synthetic leather based on self-repairing waterborne polyurethane and preparation method thereof |
| CN110343457A (en) * | 2019-07-26 | 2019-10-18 | 株洲飞鹿高新材料技术股份有限公司 | A kind of steel construction automatically cleaning, fire prevention multifunctional coating and preparation method |
| CN110746878A (en) * | 2019-11-19 | 2020-02-04 | 合众（佛山）化工有限公司 | High-hardness anti-sagging polyurethane water-based functional coating |
| CN110746878B (en) * | 2019-11-19 | 2021-10-01 | 合众（佛山）化工有限公司 | High-hardness anti-sagging polyurethane water-based functional coating |
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