CN116396192A - Diurea anti-sagging agent and synthesis method thereof - Google Patents
Diurea anti-sagging agent and synthesis method thereof Download PDFInfo
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- CN116396192A CN116396192A CN202310198376.7A CN202310198376A CN116396192A CN 116396192 A CN116396192 A CN 116396192A CN 202310198376 A CN202310198376 A CN 202310198376A CN 116396192 A CN116396192 A CN 116396192A
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- 238000007665 sagging Methods 0.000 title claims abstract description 73
- 238000001308 synthesis method Methods 0.000 title claims abstract description 10
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical compound O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 title description 2
- 239000011347 resin Substances 0.000 claims abstract description 45
- 229920005989 resin Polymers 0.000 claims abstract description 45
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 43
- 238000000576 coating method Methods 0.000 claims abstract description 29
- 239000011248 coating agent Substances 0.000 claims abstract description 27
- ULUZGMIUTMRARO-UHFFFAOYSA-N (carbamoylamino)urea Chemical compound NC(=O)NNC(N)=O ULUZGMIUTMRARO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 22
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 15
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 10
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 10
- 239000004925 Acrylic resin Substances 0.000 claims description 9
- 229920000178 Acrylic resin Polymers 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- MPWSRGAWRAYBJK-UHFFFAOYSA-N (4-tert-butylphenyl)methanamine Chemical compound CC(C)(C)C1=CC=C(CN)C=C1 MPWSRGAWRAYBJK-UHFFFAOYSA-N 0.000 claims description 7
- SFUPGSLHZPWQIZ-UHFFFAOYSA-N 1-tert-butyl-4-(isocyanatomethyl)benzene Chemical compound CC(C)(C)C1=CC=C(CN=C=O)C=C1 SFUPGSLHZPWQIZ-UHFFFAOYSA-N 0.000 claims description 7
- 229920001225 polyester resin Polymers 0.000 claims description 7
- 239000004645 polyester resin Substances 0.000 claims description 7
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims 1
- 238000002604 ultrasonography Methods 0.000 claims 1
- 239000011087 paperboard Substances 0.000 description 25
- 238000002474 experimental method Methods 0.000 description 17
- 239000002966 varnish Substances 0.000 description 17
- 239000003973 paint Substances 0.000 description 14
- 239000011521 glass Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000011247 coating layer Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- -1 small molecule compounds Chemical class 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
-
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- 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
- C09D7/63—Additives non-macromolecular organic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a biurea anti-sagging agent and a synthesis method thereof, wherein the molecular structural formula of the biurea anti-sagging agent is shown as the formula (I):
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a biurea anti-sagging agent and a synthesis method thereof.
Background
Ureido compounds are often used for the design and preparation of gels, bactericidal and anticancer drugs, rheological aids and the like due to the intermolecular hydrogen bonding effect. Bisurea small molecule compounds have been shown to act as sag and sedimentation resistance in coatings. This is generally explained by the fact that self-assembly or crystallization of small bisurea compounds forms anisotropic colloidal particles in the corresponding system, which then build up a three-dimensional network by particle-particle and particle interactions with other materials in the system, and which, before and after being subjected to shear forces, exert a thickening or thixotropic effect by disruption and reconstitution of the three-dimensional network, providing the desired rheological properties to the final product.
Traditional sag resistance agents, such as bentonite, fumed silica, are not ideal for chemical resistance and affect gloss; and polyamide waxes, are prone to azo compounds, yellowing and affect gloss. The urea anti-sagging agent has the characteristics of excellent anti-sagging property, small addition amount, convenient use, no reduction of leveling property, no influence on the gloss of a paint film, easy dispersion, wide application range and the like, so the urea anti-sagging agent is the best choice of high-end paint.
The coating field has been studied about urea anti-sagging agents and has been largely applied to industrial paint and automotive paint technologies. In order to overcome the adverse effect of the residual anti-sagging agent in the coating layer after the coating film is dried on the appearance of the coating layer, such as gloss and distinctness of image, the Ackersinobell company discloses a modified anti-sagging resin, which is called sagging control agent (Sag Control Agent, SCA) modified resin, and the SCA system consists of symmetrical urea derivative needle structures. The Ackersinobell company found that the leveling properties of the varnishes using the SCA system were significantly better than those of varnishes not using the SCA system, and that the desired film thickness of the coating could be achieved by increasing the flow of lacquer out. However, the anti-sagging agent added into the paint has the advantages of large dosage, high cost and pollution; the time consumption is long and the energy consumption is high when the paint is baked and coated.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a biurea anti-sagging agent.
The second object of the invention is to provide a method for synthesizing the biurea anti-sagging agent.
A third object of the present invention is to provide an anti-sagging resin.
A fourth object of the present invention is to provide a method for producing the above sag resistant resin.
A fifth object of the present invention is to provide the use of the above anti-sagging resin in the preparation of a coating.
The technical scheme of the invention is summarized as follows:
the molecular structural formula of the biurea anti-sagging agent is shown as the formula (I):
the synthesis method of the biurea anti-sagging agent comprises the following steps of one of two modes:
mode one: dripping the 1, 6-hexamethylene diisocyanate solution into the 4-tert-butyl benzyl amine solution, reacting under stirring, and filtering to obtain the biurea anti-sagging agent shown in the formula (I);
mode two: dripping 1, 6-hexamethylenediamine solution into 4-tert-butyl benzyl isocyanate solution, reacting under stirring, and filtering to obtain a biurea anti-sagging agent shown as a formula (I);
the solvent of the 1, 6-hexamethylene diisocyanate solution is preferably at least one of aromatic hydrocarbon 100, toluene, paraxylene and butyl acetate; the solvent of the 4-tertiary butyl benzylamine solution is preferably at least one of aromatic hydrocarbon 100, toluene, paraxylene and butyl acetate; the solvent of the 1, 6-hexamethylenediamine solution is preferably at least one of aromatic hydrocarbon 100, toluene, paraxylene and butyl acetate; the solvent of the 4-tert-butyl benzyl isocyanate solution is preferably at least one of aromatic hydrocarbon 100, toluene, paraxylene and butyl acetate.
A preparation method of sag-resistant resin comprises the following steps:
adding the biurea anti-sagging agent into resin under the condition of 0-25 ℃ and ultrasonic, and stirring to obtain anti-sagging resin; the mass ratio of the biurea anti-sagging agent to the resin is as follows: 4-10:90-96.
The power of the ultrasonic wave is preferably 100-500W; the stirring speed is preferably 300-600 rpm; the stirring time is preferably 10 to 60 minutes.
The resin is preferably a polyester resin or an acrylic resin.
The polyester resin is preferably at least one of SN805, SY961, CFR8675, ETERKYD 50031, ETERKYD50141-TK-40 and ETERKYD 5019-R-40.
The acrylic resin is preferably at least one of CY951, FX-W9286, HU56020, ETERAC 72827, WAP-347, setalux1184 and Setalux 1753.
The sagging-resistant resin prepared by the preparation method.
The application of the sagging resistant resin in preparing paint.
The invention has the advantages that:
the synthesis method of the biurea anti-sagging agent is simple, and the single-time yield is more than 95%; the preparation method of the sagging-resistant resin is simple, and different sagging-resistant resins can be applied to different fields; the application range is expanded, and compared with the traditional product, the anti-sagging resin has less addition; after the sag-resistant resin provided by the invention is applied to a coating, the sag resistance value of the coating is increased from 150 mu m to 200 mu m, and the coating is baked for 15min at 140 ℃ to become transparent.
Detailed Description
The invention is further illustrated by the following examples. It will be appreciated by persons skilled in the art that the particular embodiments described herein are illustrative only and are not limiting of the invention.
The experimental methods used in the embodiments are all conventional methods unless otherwise specified; the materials, reagents and the like used, unless otherwise specified, are all commercially available.
The varnish base material used in the invention is prepared by self, and the ingredients are listed below.
TABLE 1 varnish base formulation table
The varnish curing agent used in the invention, HDI isocyanate solvent HDI trimer yellowing-resistant curing agent, is purchased from Aloqi chemical industry Co., ltd.
The commercially available sag resistant resin product used in the present invention, setalux 91115 SS-55SCA, was purchased from Allnex coating resin company.
Example 1
The synthesis method of the biurea anti-sagging agent comprises the following steps:
3.30g of 4-tert-butylbenzylamine and 85.00g of aromatic hydrocarbon 100 are added into a 250mL three-necked flask equipped with a magnet, a thermometer and a dropping funnel at 20 ℃ and stirred uniformly at 300rpm to obtain a 4-tert-butylbenzylamine solution; another 25mL glass bottle is used to prepare 1.70g of 1, 6-hexamethylene diisocyanate solution obtained by mixing 1.70g of 1, 6-hexamethylene diisocyanate with 10.00g of aromatic hydrocarbon 100, after 10min of sonication, the mixture was transferred to a dropping funnel and added dropwise to a solution of 4-tert-butylbenzylamine at 300 rpm. After the completion of the dropwise addition, the reaction was stirred at room temperature for 4 hours. The reaction was stopped, and after suction filtration, the cake was washed twice with aromatic hydrocarbon 100, and white solid was collected by suction filtration again to obtain 26.64g of wet cake. Drying at 60deg.C to constant weight gives 4.82g of white powder with a yield of 96.40% and a melting range of 196.7-198.1 ℃. 1 H NMR(600MHz,DMSO-d 6 )δ7.30(d,J＝7.8Hz,4H),7.15(d,J＝7.7Hz,4H),6.18(s,2H),5.85(s,2H),4.16(d,J＝5.4Hz,4H),2.98(d,J＝5.9Hz,4H),1.24(s,26H)。
Experiments prove that butyl acetate and paraxylene are used or the volume ratio is 1:1 and toluene, and other components in the same manner as in this example, can be used to prepare the biurea anti-sagging agent with the molecular structural formula shown in formula (I).
Example 2
The synthesis method of the biurea anti-sagging agent comprises the following steps:
3.82g of 4-tert-butyl benzyl isocyanate and 85.00g of aromatic hydrocarbon 100 are added into a 250mL three-necked flask equipped with a magnet, a thermometer and a dropping funnel at 20 ℃ and stirred uniformly at 300rpm to obtain a 4-tert-butyl benzyl isocyanate solution; a25 mL glass bottle was used to prepare a 1, 6-hexamethylenediamine solution by mixing 1.18g of 1, 6-hexamethylenediamine with 10.00g of aromatic hydrocarbon 100, and after ultrasonic treatment for 10min, the solution was transferred into a dropping funnel, and was added dropwise to a 4-tert-butyl benzyl isocyanate solution at a rotation speed of 300 rpm. After the completion of the dropwise addition, the reaction was stirred at room temperature for 4 hours. The reaction was stopped, and after suction filtration, the cake was washed twice with aromatic hydrocarbon 100, and again, white solid was collected by suction filtration to obtain 25.48g of wet cake. Drying to constant weight at 60℃gave 4.78g of white powder in 95.60% yield.
Through the detection of the nuclear magnetism, 1 H NMR(600MHz,DMSO-d 6 ) Delta 7.30 (d, j=7.8 hz, 4H), 7.16 (d, j=7.7 hz, 4H), 6.20 (s, 2H), 5.85 (s, 2H), 4.15 (d, j=5.4 hz, 4H), 2.97 (d, j=5.9 hz, 4H), 1.25 (s, 26H). The structure of the compound is shown as formula I.
Experiments prove that the aromatic hydrocarbon 100 in the embodiment is replaced by butyl acetate, paraxylene or a mixture of paraxylene and toluene with the volume ratio of 1:1, and other embodiments can prepare the biurea anti-sagging agent with the molecular structural formula shown in the formula (I).
Example 3
A preparation method of sag-resistant resin comprises the following steps:
47.50g of acrylic resin ETERAC 72827 is taken in a 100mL beaker under the condition of 100W ultrasonic at 5 ℃, 2.50g of the biurea anti-sagging agent synthesized in the example 1 (optionally synthesized in the example 2) is added, and stirring is carried out at 300rpm for 60min, so that the milky anti-sagging resin is obtained.
Example 4
A preparation method of sag-resistant resin comprises the following steps:
45.00g of polyester resin CFR8675 is taken in a 100mL beaker under the condition of ultrasonic wave at 25 ℃ and 300W, 5.00g of the biurea anti-sagging agent synthesized in the example 1 (optionally synthesized in the example 2) is added, and the mixture is stirred for 30min at 500rpm, so that the milky anti-sagging resin is obtained.
Experiments prove that the polyester resins SN805, SY961, ETERKYD 50031, ETERKYD50141-TK-40, ETERKYD 5019-R-40 or the mixture of SN805 and SY961 with the mass ratio of 1:1 are used for replacing the polyester resin CFR8675 of the embodiment, and the milky anti-sagging resin is prepared respectively in the same way as the embodiment.
Example 5
A preparation method of sag-resistant resin comprises the following steps:
48g of acrylic resin CY951 is taken in a 100mL beaker under the condition of 500W ultrasonic at 0 ℃, 2g of the biurea anti-sagging agent synthesized in the example 1 (optionally synthesized in the example 2) is added, and stirring is carried out at 600rpm for 10min, so that the milky anti-sagging resin is obtained.
Experiments prove that acrylic resin CY951 in the embodiment is replaced by acrylic resins FX-W9286, HU56020, WAP-347 or a mixture of Setalux1184 and Setalux 1753 in a mass ratio of 1:1, and the milky anti-sagging resin is prepared respectively in the same manner as in the embodiment.
Example 6
The application of the sagging-resistant resin in preparing the paint comprises the following steps:
6.00g of the sag resistant resin prepared in example 3 and 18.00g of the varnish base were taken in a 100mL beaker, stirred at 300rpm for 10min, then 8.00g of the varnish curing agent was added and stirred with a spatula for 1min to give a coating.
Blade coating experiment: about 5.00g of paint is taken on a paperboard, the paperboard is uniformly scraped by a sagging coater with different gradient scales, the paperboard is vertically placed, and after the paperboard is naturally air-dried, the sagging resistance value of the paperboard is detected.
Baking experiment: about 5.00g of the coating was applied to a transparent glass plate, which was spread uniformly with a sagging coater having the same scale, and then the glass plate was heated on a constant temperature heating table, and the transparent temperature and the required time period were measured and recorded, see tables 2 and 3.
Example 7
The application of the sagging-resistant resin in preparing the paint comprises the following steps:
6.00g of the sag resistant resin prepared in example 4 and 18.00g of the varnish base were taken in a 100mL beaker, stirred at 300rpm for 10min, then 8.00g of the varnish curing agent was added and stirred with a spatula for 1min to give a coating.
Blade coating experiment: about 5.00g of paint is taken on a paperboard, the paperboard is uniformly scraped by a sagging coater with different gradient scales, the paperboard is vertically placed, and after the paperboard is naturally air-dried, the sagging resistance value of the paperboard is detected.
Baking experiment: about 5.00g of the coating was applied to a transparent glass plate, which was spread uniformly with a sagging coater having the same scale, and then the glass plate was heated on a constant temperature heating table, and the transparent temperature and the required time period were measured and recorded, see tables 2 and 3.
Example 8
The application of the sagging-resistant resin in preparing the paint comprises the following steps:
6.00g of the sag resistant resin prepared in example 5 and 18.00g of the varnish base were taken in a 100mL beaker, stirred at 300rpm for 10min, then 8.00g of the varnish curing agent was added and stirred with a spatula for 1min to give a coating.
Blade coating experiment: about 5.00g of paint is taken on a paperboard, the paperboard is uniformly scraped by a sagging coater with different gradient scales, the paperboard is vertically placed, and after the paperboard is naturally air-dried, the sagging resistance value of the paperboard is detected.
Baking experiment: about 5.00g of the coating was applied to a transparent glass plate, which was spread uniformly with a sagging coater having the same scale, and then the glass plate was heated on a constant temperature heating table, and the transparent temperature and the required time period were measured and recorded, see tables 2 and 3.
Comparative example 1
Preparation of coatings using Allnex Setalux 91115 SS-55SCA sag resistant resin:
6.00g of the Allnex Setalux 91710 SS-55SCA sag resistant resin and 18.00g of the varnish base were taken in a 100mL beaker, stirred at 300rpm for 10min, then 8.00g of varnish curing agent was added, and stirred with a spatula for 1min to obtain a coating.
Blade coating experiment: about 5.00g of paint is taken on a paperboard, the paperboard is uniformly scraped by a sagging coater with different gradient scales, the paperboard is vertically placed, and after the paperboard is naturally air-dried, the sagging resistance value of the paperboard is detected.
Baking experiment: about 5.00g of the coating was applied to a transparent glass plate, which was spread uniformly with a sagging coater having the same scale, and then the glass plate was heated on a constant temperature heating table, and the transparent temperature and the required time period were measured and recorded, see tables 2 and 3.
Comparative example 2
And (3) carrying out a doctor blade experiment without adding an anti-sagging agent, wherein the doctor blade experiment comprises the following steps of:
6.00g ETERAC 72827 acrylic resin and 18.00g of the varnish base were taken in a 100mL beaker, stirred at 300rpm for 10 minutes, then 8.00g of the varnish curing agent was added, and stirred using a spatula for 1 minute to obtain a coating.
Blade coating experiment: about 5.00g of varnish is taken on a paperboard, the paperboard is uniformly scraped and coated by a sagging coater with different gradient scales, the paperboard is vertically placed, and after the paperboard is naturally air-dried, the sagging resistance value of the paperboard is detected.
Baking experiment: about 5.00g of varnish was applied to a transparent glass plate and spread uniformly with a sagging coater having the same scale, and the spread coating was transparent.
TABLE 2 knife coating test data
TABLE 3 baking test data
Claims (10)
1. The bisurea anti-sagging agent is characterized in that the molecular structural formula is shown as the formula (I):
2. the method for synthesizing the biuret anti-sagging agent according to claim 1, which is characterized by comprising the steps of one of the following two ways:
mode one: dripping the 1, 6-hexamethylene diisocyanate solution into the 4-tert-butyl benzyl amine solution, reacting under stirring, and filtering to obtain the biurea anti-sagging agent shown in the formula (I);
mode two: dripping 1, 6-hexamethylenediamine solution into 4-tert-butyl benzyl isocyanate solution, reacting under stirring, and filtering to obtain a biurea anti-sagging agent shown as a formula (I);
3. the synthesis method according to claim 2, wherein the solvent of the 1, 6-hexamethylene diisocyanate solution is at least one of aromatic hydrocarbon 100, toluene, paraxylene and butyl acetate; the solvent of the 4-tertiary butyl benzylamine solution is at least one of aromatic hydrocarbon 100, toluene, paraxylene and butyl acetate; the solvent of the 1, 6-hexamethylenediamine solution is at least one of aromatic hydrocarbon 100, toluene, paraxylene and butyl acetate; the solvent of the 4-tert-butyl benzyl isocyanate solution is at least one of aromatic hydrocarbon 100, toluene, paraxylene and butyl acetate.
4. A preparation method of sag-resistant resin is characterized by comprising the following steps: adding the biurea anti-sagging agent in the resin under the condition of 0-25 ℃ and ultrasonic, and stirring to obtain the anti-sagging resin; the mass ratio of the biurea anti-sagging agent to the resin is as follows: 4-10:90-96.
5. The preparation method according to claim 4, wherein the power of the ultrasound is 100-500W; the stirring speed is 300-600 rpm; the stirring time is 10-60 min.
6. The process according to claim 4, wherein the resin is a polyester resin or an acrylic resin.
7. The method according to claim 6, wherein the polyester resin is at least one of SN805, SY961, CFR8675, ETERKYD 50031, ETERKYD50141-TK-40 and ETERKYD 5019-R-40.
8. The method according to claim 6, wherein the acrylic resin is at least one of CY951, FX-W9286, HU56020, ETERAC 72827, WAP-347, setalux1184 and Setalux 1753.
9. An anti-sagging resin prepared by the preparation method of any one of claims 4 to 8.
10. Use of the sag resistant resin according to claim 9 for preparing a coating.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299934A (en) * | 2017-09-07 | 2018-07-20 | 立邦涂料（中国）有限公司 | A kind of rheo-material, Preparation method and use |
| CN115286954A (en) * | 2022-09-02 | 2022-11-04 | 长兴化学工业(中国)有限公司 | Sag control agents and coating compositions containing the same |
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- 2023-03-03 CN CN202310198376.7A patent/CN116396192A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299934A (en) * | 2017-09-07 | 2018-07-20 | 立邦涂料（中国）有限公司 | A kind of rheo-material, Preparation method and use |
| CN115286954A (en) * | 2022-09-02 | 2022-11-04 | 长兴化学工业(中国)有限公司 | Sag control agents and coating compositions containing the same |
Non-Patent Citations (1)
| Title |
|---|
| YING-FENG HE等: "Multiscale structures and rheology of bisurea-loaded resins for anti-sagging applications", 《SOFT MATTER》, pages 10628 - 10639 * |
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