CN114853742A - Preparation method and application of modified HDI uretdione curing agent - Google Patents
Preparation method and application of modified HDI uretdione curing agent Download PDFInfo
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- CN114853742A CN114853742A CN202210524133.3A CN202210524133A CN114853742A CN 114853742 A CN114853742 A CN 114853742A CN 202210524133 A CN202210524133 A CN 202210524133A CN 114853742 A CN114853742 A CN 114853742A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
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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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2237—Oxides; Hydroxides of metals of titanium
- C08K2003/2241—Titanium dioxide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
- C08K2003/3045—Sulfates
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
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Abstract
The invention discloses a preparation method and application of a modified HDI uretdione curing agent, wherein the method comprises the following steps: and mixing and reacting HDI uretdione and N-hydroxyethyl-2-imidazolidinone to generate the modified HDI uretdione curing agent. According to the method, HDI uretdione and N-hydroxyethyl-2-imidazolidinone are used as raw materials to react to prepare the curing agent, the curing agent can be applied to a polyurethane floor paint system, and compared with the traditional aliphatic polyurethane floor paint, the curing agent is matched with a main paint for use, the leveling property of a paint film is good, the drying speed after construction is high, the strength of the dried paint film is high, the weather resistance is excellent, and meanwhile, on the premise that a large amount of extinction powder is not added, the glossiness of the dried paint film is low, and the method is very suitable for the field of floor paint with matte requirements.
Description
Technical Field
The invention relates to a modified HDI uretdione curing agent, in particular to a preparation method and application of the modified HDI uretdione curing agent.
Background
The polyurethane floor coating has the advantages of good elasticity, good chemical resistance, high reaction activity at low temperature and the like. Currently, the commercial polyurethane floor paint curing agent mainly comprises polymeric MDI (diphenylmethane diisocyanate), and aromatic isocyanate curing agents such as polymeric MDI (diphenylmethane diisocyanate) have a benzene ring structure, so that the weather resistance and yellowing resistance of the coating after film formation are poor. In addition, a polyurethane coating system taking HDI tripolymer as a curing agent is also available in the market, and the product has excellent performances such as weather resistance, chemical resistance, wear resistance and the like, but because the reaction activity of aliphatic isocyanate is slow, a large amount of catalyst needs to be added for drying; in high volume applications, the fast curing feature is highly desirable because it is important to reduce construction cycle time and save cost. Therefore, the development of an isocyanate curing agent which has the characteristics of quick curing and excellent comprehensive properties such as weather resistance, yellowing resistance, mechanical properties and the like of the coating is of great significance.
On the other hand, on the premise of not adding the matting filler, the film gloss of the film formed by the traditional polyurethane floor finish paint is higher, if the polyurethane floor finish paint needs to realize lower gloss, the polyurethane floor finish paint can be realized only by adding a large amount of filling materials such as matting powder, and the like, which generally influences the transparency and other properties of the film.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method and application of a modified HDI uretdione curing agent.
According to one aspect of the invention, HDI uretdione and N-hydroxyethyl-2-imidazolidinone are used as raw materials to react to prepare the curing agent, the curing agent can be applied to a polyurethane floor paint system, compared with the traditional aliphatic polyurethane floor paint, the curing agent is matched with a main paint, the leveling property of a paint film is good, the drying speed after construction is high, the strength of the paint film is high after drying, the weather resistance is excellent, and meanwhile, on the premise that a large amount of matting powder is not added, the glossiness of the dried paint film is low, so that the preparation method is very suitable for the field of floor paints with matte requirements.
According to a second aspect of the present invention, there is also provided a modified HDI uretdione curing agent obtained by the foregoing preparation method.
According to the third aspect of the invention, the weather-resistant solvent-free polyurethane floor paint is prepared by matching the modified HDI uretdione curing agent prepared by the preparation method with the main paint.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the preparation method of the modified HDI uretdione curing agent comprises the following steps:
and mixing and reacting HDI uretdione and N-hydroxyethyl-2-imidazolidinone to generate the modified HDI uretdione curing agent.
In a pre-selected variant of the invention, the HDI uretdione is prepared from hexamethylene diisocyanate by oligomerization and contains 30 to 50 mol% of HDI uretdione, 15 to 40 mol% of HDI trimer and the remainder of other polymers, based on 100% of the total molar amount of HDI uretdione.
In a pre-selected variant of the invention, the HDI uretdione has an NCO functional group content of 20 to 23%.
In a preselected embodiment of the invention, the ratio of the HDI uretdione to N-hydroxyethyl-2-imidazolidinone used, based on the molar ratio of NCO functional groups to N-hydroxyethyl-2-imidazolidinone, is (2-6):1, preferably (2-4): 1.
In a pre-selected embodiment of the invention, the reaction is carried out at 70-80 ℃ for 4-5 h.
The HDI uretdione contains a plurality of active ingredients with NCO functional groups, such as uretdione shown in formula I, trimer shown in formula II, polymer shown in formula III and IV, and the like.
Taking the reaction of the uretdione shown in the formula I in the reaction system of the invention as an example (the reaction mechanism is shown in the following), one molecule of N-hydroxyethyl-2-imidazolidinone reacts with two molecules of HDI uretdione to generate a product with a longer molecular chain, a higher crosslinking degree and more tertiary amine group content, which is beneficial to remarkably improving the curing rate and the mechanical property when the product is applied to polyurethane floor paint, and simultaneously keeping good weather resistance, wear resistance, solvent resistance and the like. The reactions of the trimer shown in the formula II and the multimers shown in the formulas III, IV and V in the system of the invention are similar to the reaction of the uretdione shown in the formula I and the N-hydroxyethyl-2-imidazolidinone, and similar technical effects can be achieved by the same method, and are not repeated herein.
The invention also provides a modified HDI uretdione curing agent prepared by the method.
The invention also provides weather-resistant solvent-free polyurethane floor paint, which comprises main paint and a curing agent; the main paint comprises the following components in parts by weight:
the curing agent is the modified HDI uretdione curing agent prepared by the method;
the mass ratio of the main paint to the curing agent is 1 (1.2-1.5), preferably 1 (1.3-1.4).
In a pre-selected embodiment of the invention, the castor oil polyol has a hydroxyl number of 200-.
In a preselected embodiment of the invention, the catalyst is at least one of dibutyltin dilaurate, tin isooctanoate, and bismuth isooctanoate, preferably dibutyltin dilaurate.
In a preselected aspect of the invention, the wetting and dispersing agent is at least one of BYK-110, BYK-111, and EFKA-4015;
preferably, the defoaming agent is at least one of AFCONA-2270, AFCONA-2620-85D 1 and AFCONA-2791;
preferably, the filler is at least one of precipitated barium sulfate, talcum powder, calcium carbonate and wollastonite powder;
preferably, the pigment is selected from at least one of titanium dioxide and carbon black, preferably titanium dioxide R996 (herboa), carbon black C311 (Shanghai coking).
The preparation process of the weather-resistant solvent-free polyurethane floor paint can be prepared by adopting a conventional process, for example, castor oil polyol, a wetting dispersant, a defoaming agent, a filler, a pigment and a catalyst are uniformly mixed to prepare a main paint, then the main paint is prepared with a modified HDI uretdione curing agent in situ in the using process, and after the main paint and the modified HDI uretdione curing agent are uniformly mixed, the mixture is coated on a substrate by using a trowel and then dried.
Preferably, in the preparation process of the main paint, the raw material mixture is ground and dispersed by a high-speed dispersion machine under the mixing condition that the castor oil polyol, the wetting dispersant, the defoamer and the catalyst are added into a grinding tank, the mixture is stirred for 5min at the speed of 600r/min for 400-.
The invention has the following beneficial effects:
(1) the modified HDI uretdione curing agent disclosed by the invention is matched with the main paint prepared from castor oil polyol to produce the polyurethane floor paint, and the fact that the glossiness of a paint film is low compared with that of a paint film formed by a traditional HDI tripolymer curing agent is surprisingly found, so that the matting performance of the modified HDI uretdione curing agent disclosed by the invention is very excellent, and the required matte effect can be realized without adding matting powder in a paint film system.
(2) The modified HDI uretdione curing agent disclosed by the invention is low in initial reaction speed, so that the construction period of the bi-component polyurethane floor coating is long, the paint can be sufficiently leveled after construction, and the paint film defects such as trowel marks and roller marks are reduced.
(3) In the modified HDI uretdione curing agent, the structure containing tertiary amine groups can promote the later reaction of a system, so that the curing and film-forming process of a paint film is accelerated, and the defect of slow reaction activity of the traditional aliphatic isocyanate curing agent is effectively overcome.
(4) The modified HDI uretdione curing agent has high crosslinking degree and increased molecular weight, has a promoting effect on improving the mechanical properties such as tensile strength of a paint film, and can be used for preparing floor paint with excellent mechanical properties.
Detailed Description
The present invention is further illustrated by the following specific examples, which are intended to be illustrative of the invention and are not to be construed as limiting the scope of the invention.
The method for testing the performance of the floor coating in the following examples and comparative examples of the invention refers to the method in GB/T22374-2018.
The NCO content in the following examples and comparative examples according to the invention was determined by the di-n-butylamine titration method.
The main raw material information in the invention is as follows:
castor oil polyol (A4105) having a hydroxyl value of 315mgKOH/g and a functionality of 3, Shanghai Jing Nissan Material Co., Ltd
Wetting dispersant (BYK-110), German Bike
Antifoaming agent (AFCONA-2620-85D 1), Effolner
Precipitation of barium sulfate, Yibin Yaqi nanotechnology
Titanium dioxide (R996), boa herboria
Dibutyl tin dilaurate, alatin
HDI uretdione (trade designation HT-400), Vanhua Chemicals, containing 40 mol% HDI uretdione, 30 mol% HDI trimer and 30 mol% other polymers, and having an NCO content of 21.8%;
HDI uretdione (trade name N3400), scientific, containing 40 mol% HDI uretdione, 30 mol% HDI trimer and 30 mol% other polymers, with an NCO content of 21.8%;
n-hydroxyethyl-2-imidazolidinone, Hubeixin Rundchemical Co., Ltd
[ example 1 ]
592g of HDI uretdione (Wanhua HT-400) and 100g N-hydroxyethyl-2-imidazolidinone are added into a reaction kettle, mixed uniformly and heated to 70 ℃ for reaction for 5 hours. And when the NCO value in the system reaches about 9.3 wt%, stopping the reaction to obtain the modified HDI uretdione curing agent A, and putting the modified HDI uretdione curing agent A into a closed container for later use.
[ example 2 ]
740g of HDI uretdione (Wanhua HT-400) and 100g N-hydroxyethyl-2-imidazolidinone are added into a reaction kettle, mixed uniformly and heated to 80 ℃ for reaction for 4 h. And when the NCO value in the system reaches about 11.5 wt%, stopping the reaction to obtain a modified HDI uretdione curing agent B, and putting the modified HDI uretdione curing agent B into a closed container for later use.
[ example 3 ]
880g of HDI uretdione (CorsiChun N3400) and 100g N-hydroxyethyl-2-imidazolidinone are added into a reaction kettle, mixed uniformly and heated to 80 ℃ for reaction for 4 hours. And when the NCO value in the system reaches about 13.1 wt%, stopping the reaction to obtain a modified HDI uretdione curing agent C, and putting the modified HDI uretdione curing agent C into a closed container for later use.
[ example 4 ]
1036g of HDI uretdione (CorsiChun 3400) and 100g N-hydroxyethyl-2-imidazolidinone are added into a reaction kettle, mixed uniformly and heated to 75 ℃ for reaction for 4.5 h. And when the NCO value in the system reaches about 14.2 wt%, stopping the reaction to obtain a modified HDI uretdione curing agent D, and putting the modified HDI uretdione curing agent D into a closed container for later use.
[ example 5 ]
1184g of HDI uretdione (Wanhua HT-400) and 100g N-hydroxyethyl-2-imidazolidinone are added into a reaction kettle, mixed uniformly and heated to 80 ℃ for reaction for 4.5 h. And when the NCO value in the system reaches about 15.7 wt%, stopping the reaction to obtain the modified HDI uretdione curing agent E, and putting the modified HDI uretdione curing agent E into a closed container for later use.
[ application example ]
The main paint of the floor paint is prepared according to the following formula:
grinding and dispersing the components by a high-speed dispersion machine under the mixing conditions that: adding castor oil polyalcohol, a wetting dispersant, a defoaming agent and dibutyltin dilaurate into a grinding tank, starting 600r/min, stirring for 5min, uniformly mixing, adding precipitated barium sulfate and titanium dioxide, adjusting the rotating speed to 3000r/min, grinding for 2h until the fineness is less than 25um, and discharging to obtain the floor paint main paint.
After 100g of floor paint main paint and 130g of the modified HDI uretdione curing agent prepared in each example were respectively and uniformly mixed, the mixture was coated on the surface of a non-asbestos fiber cement board substrate by a trowel, and various performances of different obtained floor paints were tested according to the standard in GB/T22374-one 2018, and the test results are shown in Table 1. In addition, unmodified HDI uretdione (Wanhua HT-400), HDI trimer (Wanhua HT-100) and polymeric MDI (Wanhua PM-200) are respectively used as curing agents, floor paints are prepared by the same method, and performance tests are carried out, wherein the test results are shown in Table 1.
TABLE 1 results of Performance test
As can be seen from the above table, compared with the traditional HDI trimer curing agent paint film and polymeric MDI curing agent paint film, the modified HDI uretdione curing agent has the matte frosting effect, and the matte requirement can be met without adding a large amount of matting powder; paint films prepared directly from HDI uretdione as curing agent have the same matte appearance, but the drying time is too slow, the tensile strength is low, and the paint films after the QUV (ultraviolet light weathering test) are foamed and peeled off and have no use value.
In conclusion, the paint film prepared by applying the modified HDI uretdione curing agent has excellent performances in drying time, wear resistance, tensile strength, external light leveling property, weather resistance and other performances, and is very suitable for the field of matte weather-resistant floor paint.
The above description is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, several modifications and additions can be made without departing from the method of the present invention, and these modifications and additions should also be regarded as the protection scope of the present invention.
Claims (10)
1. The preparation method of the modified HDI uretdione curing agent is characterized by comprising the following steps:
and mixing and reacting HDI uretdione and N-hydroxyethyl-2-imidazolidinone to generate the modified HDI uretdione curing agent.
2. The method of preparing a modified HDI uretdione curing agent according to claim 1, wherein the HDI uretdione is prepared from hexamethylene diisocyanate by an oligomerization reaction, and comprises 30 to 50 mol% of HDI uretdione, 15 to 40 mol% of HDI trimer, and the balance other polymers, based on the total molar amount of HDI uretdione as 100%.
3. The method of claim 2, wherein the HDI uretdione has an NCO functional group content of 20 to 23%.
4. The method for preparing a modified HDI uretdione curing agent according to claim 3, wherein the HDI uretdione and N-hydroxyethyl-2-imidazolidinone are used in a ratio of (2-6):1, preferably (2-4):1, in terms of a molar ratio of the NCO functional group to the N-hydroxyethyl-2-imidazolidinone.
5. The method for preparing a modified HDI uretdione curing agent according to any one of claims 1 to 4, wherein the reaction is carried out at 70 to 80 ℃ for 4 to 5 hours.
6. A modified HDI uretdione curing agent obtainable by the process according to any of claims 1 to 5.
7. The weather-resistant solvent-free polyurethane floor paint is characterized by comprising main paint and a curing agent; the main paint comprises the following components in parts by weight:
the curing agent is a modified HDI uretdione curing agent prepared by the method of any one of claims 1 to 5;
the mass ratio of the main paint to the curing agent is 1 (1.2-1.5), preferably 1 (1.3-1.4).
8. The weather-resistant solvent-free polyurethane floor paint as claimed in claim 7, wherein the castor oil polyol has a hydroxyl value of 200-400mgKOH/g and a functionality of 3-5, and is preferably at least one of Sovermol 750, A4105 and Uric F40.
9. The weatherable, solventless polyurethane floor paint of claim 7 or 8, wherein the catalyst is at least one of dibutyltin dilaurate, tin isooctanoate, and bismuth isooctanoate, preferably dibutyltin dilaurate.
10. The weather-resistant solvent-free polyurethane floor paint of claim 9, wherein the wetting dispersant is at least one of BYK-110, BYK-111 and EFKA-4015;
preferably, the defoaming agent is at least one of AFCONA-2270, AFCONA-2620-85D 1 and AFCONA-2791;
preferably, the filler is at least one of precipitated barium sulfate, talcum powder, calcium carbonate and wollastonite powder;
preferably, the pigment is selected from at least one of titanium dioxide and carbon black, preferably titanium dioxide R996 and carbon black C311.
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Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5250632A (en) * | 1992-08-13 | 1993-10-05 | Texaco Chemical Company | Heimd-containing polyetheramine curative for flexible, toughened products |
| DE19549029A1 (en) * | 1995-12-28 | 1997-07-03 | Huels Chemische Werke Ag | Compounds containing cyclic amidine and uretdione groups, a process for their preparation and their use |
| JPH10182795A (en) * | 1996-12-26 | 1998-07-07 | Nippon Paint Co Ltd | Crater preventing agent and cation electrocoating material composition containing the same |
| US5859164A (en) * | 1996-09-13 | 1999-01-12 | Huels Aktiengesellschaft | Uretdione-functional polyaddition compounds, a process for their preparation, and their use |
| CN1649929A (en) * | 2002-03-27 | 2005-08-03 | 罗狄亚化学公司 | Low-viscosity polyisocyanate composition having high functionality and method for preparing same |
| US20120095162A1 (en) * | 2010-10-18 | 2012-04-19 | Basf Se | High-functionality polyetherols and preparation and use thereof |
| WO2012100532A1 (en) * | 2011-01-27 | 2012-08-02 | 襄阳精信汇明化工有限责任公司 | Modified 1,6-hexamethylene diisocyanate biuret curing agent and preparation method therefor |
| CN105229041A (en) * | 2013-05-17 | 2016-01-06 | 东洋纺株式会社 | Nitrogen-containing heterocycle compound modified polyolefin and containing its binder composition |
| CN108300276A (en) * | 2018-03-09 | 2018-07-20 | 广东达尔新型材料有限公司 | A kind of no-solvent polyurethane floor paint and preparation method thereof |
| CN114008100A (en) * | 2019-06-24 | 2022-02-01 | Sika技术股份公司 | Polyurethane composition for the manufacture of floors, in particular for marine applications |
-
2022
- 2022-05-13 CN CN202210524133.3A patent/CN114853742B/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5250632A (en) * | 1992-08-13 | 1993-10-05 | Texaco Chemical Company | Heimd-containing polyetheramine curative for flexible, toughened products |
| DE19549029A1 (en) * | 1995-12-28 | 1997-07-03 | Huels Chemische Werke Ag | Compounds containing cyclic amidine and uretdione groups, a process for their preparation and their use |
| US5859164A (en) * | 1996-09-13 | 1999-01-12 | Huels Aktiengesellschaft | Uretdione-functional polyaddition compounds, a process for their preparation, and their use |
| JPH10182795A (en) * | 1996-12-26 | 1998-07-07 | Nippon Paint Co Ltd | Crater preventing agent and cation electrocoating material composition containing the same |
| CN1649929A (en) * | 2002-03-27 | 2005-08-03 | 罗狄亚化学公司 | Low-viscosity polyisocyanate composition having high functionality and method for preparing same |
| US20120095162A1 (en) * | 2010-10-18 | 2012-04-19 | Basf Se | High-functionality polyetherols and preparation and use thereof |
| WO2012100532A1 (en) * | 2011-01-27 | 2012-08-02 | 襄阳精信汇明化工有限责任公司 | Modified 1,6-hexamethylene diisocyanate biuret curing agent and preparation method therefor |
| CN105229041A (en) * | 2013-05-17 | 2016-01-06 | 东洋纺株式会社 | Nitrogen-containing heterocycle compound modified polyolefin and containing its binder composition |
| CN108300276A (en) * | 2018-03-09 | 2018-07-20 | 广东达尔新型材料有限公司 | A kind of no-solvent polyurethane floor paint and preparation method thereof |
| CN114008100A (en) * | 2019-06-24 | 2022-02-01 | Sika技术股份公司 | Polyurethane composition for the manufacture of floors, in particular for marine applications |
Non-Patent Citations (1)
| Title |
|---|
| SANDRA REEMERS等: "Novel Route to Dendritic Structures and Their Application for Surface Modification", JOURNAL OF POLYMER SCIENCE, PART A: POLYMER CHEMISTRY, vol. 44, no. 4, pages 1372 - 1386, XP008085402, DOI: 10.1002/pola.21251 * |
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