CN112521528B - Ionic liquid cyclodextrin-based UV resin and application thereof in coating - Google Patents
Ionic liquid cyclodextrin-based UV resin and application thereof in coating Download PDFInfo
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- CN112521528B CN112521528B CN202011325335.2A CN202011325335A CN112521528B CN 112521528 B CN112521528 B CN 112521528B CN 202011325335 A CN202011325335 A CN 202011325335A CN 112521528 B CN112521528 B CN 112521528B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
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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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention belongs to the technical field of coatings. Aiming at the problem that a film forming substance of the existing coating is derived from non-renewable resources, an ionic liquid cyclodextrin-based UV resin and application thereof are provided. The preparation method of the ionic liquid cyclodextrin-based UV resin comprises the following steps: dissolving cyclodextrin in NaOH aqueous solution to obtain a mixed solution I, and dissolving halogenated olefin in an organic solvent to obtain a mixed solution II; slowly dropwise adding the mixed solution II into the mixed solution I, heating for reaction, cooling after the reaction is finished, separating liquid, taking an organic phase, washing the organic phase to be neutral by using deionized water, and drying; dissolving the dried product in an organic solvent, dissolving the halogenated isocyanate in the same organic solvent, and mixing the two; adding an organic alkali reagent to carry out acid-base ionization reaction, and separating to obtain a final product; and dissolved in the UV monomer. According to the invention, cyclodextrin is taken as a biomass source monomer to synthesize a polymerizable prepolymer with carbon-carbon double bonds and an anion-cation structure, and the prepared paint film has environmental protection and excellent coating performance.
Description
Technical Field
The invention belongs to the technical field of coatings, and particularly relates to ionic liquid cyclodextrin-based UV resin and application thereof in a coating.
Background
The wide use of petroleum and coal resources brings various conveniences to people for clothes, eating and housing, and causes great pollution to human environment. The traditional furniture industry is the used coating, the film forming material of the coating is mainly derived from petroleum, and the renewable environment-friendly coating becomes a development trend under the influence of energy crisis and environmental protection safety factors.
The UV photocuring coating can excite active free radicals under the action of a photoinitiator through ultraviolet irradiation so as to promote cross-linking between molecules to form a film, and has the advantages of high solid content, low energy consumption, high cross-linking density, high efficiency, environmental friendliness and the like, so that the UV photocuring coating is widely applied to furniture coatings at present.
Ionic Liquids (ILs) are organic molten salts composed of positive and negative ions and exhibiting a liquid state at or near room temperature. The ionic liquid has unique physical and chemical properties such as low vapor pressure, high conductivity, wide electrochemical window, good thermal stability and the like, and has attracted interest and wide attention in academia and industry. Poly (ionic liquid) s refer to ionic liquid polymers which are generated by polymerizing ionic liquid monomers and have anionic and cationic groups on repeating units, and have the excellent properties of ionic liquids and polymers.
Cyclodextrin is a renewable energy source, is a general name of a series of cyclic oligosaccharides generated by amylose under the action of cyclodextrin glucosyltransferase produced by bacillus, and is widely used for pharmaceutical excipients and food additives at present. The problem to be solved is how to use cyclodextrin in coating.
Disclosure of Invention
Aiming at the problems that the film forming material of the existing paint is from non-renewable resources and the environmental protection performance is poor, the invention aims to provide the ionic liquid cyclodextrin-based UV resin and the application thereof in the paint.
The invention is realized by the following technical scheme:
a preparation method of ionic liquid cyclodextrin-based UV resin comprises the following steps:
A. dissolving cyclodextrin in 10-50% of NaOH aqueous solution by mass fraction to obtain a mixed solution I, and dissolving halogenated olefin in an organic solvent to obtain a mixed solution II;
B. slowly dropwise adding the mixed solution II into the mixed solution I, heating to 50-150 ℃, and reacting for 4-24 h; the molar ratio of the halogenated olefin in the mixed solution II to the hydroxyl on the cyclodextrin in the mixed solution I is (0.2-2) to 1;
C. after the reaction is finished, cooling to room temperature, separating liquid, taking organic phase solution, washing the organic phase solution to be neutral by deionized water, and drying to obtain a product;
D. dissolving the dried product in an organic solvent, dissolving halogenated isocyanate in the same organic solvent, slowly dripping the halogenated isocyanate solution into the dried product, and reacting at the temperature of 20-80 ℃ for 4-24 h; the molar ratio of the halogenated isocyanate to the hydroxyl on the initial cyclodextrin is (0.3-3): 1;
E. continuously adding an organic alkali reagent, reacting for 3-12h at the temperature of 30-100 ℃, and separating to obtain a final product;
F. dissolving the final product in an active UV monomer to obtain ionic liquid cyclodextrin UV resin;
the halogenated olefin is selected from at least one of the following compounds:
(a) halogenated olefin having one double bond: XCnH2n-1Wherein: x ═ Cl, Br, or I; n is more than or equal to 3 and less than or equal to 20;
(b) halogenated olefins containing two double bonds: XCnH2n-3Wherein: x ═ Cl, Br, or I; n is more than or equal to 5 and less than or equal to 20;
(c) halogenated olefins containing three double bonds: XCnH2n-5Wherein: x ═ Cl, Br, or I; n is more than or equal to 5 and less than or equal to 20;
(d) aromatic olefins containing double bonds:
the halogenated isocyanate is used for reacting isocyanate groups with cyclodextrin hydroxyl groups, and halogen atoms of the terminal groups are subsequently reacted with alkaline organic matters to obtain an ion pair structure, so that the final product has ionic liquid properties.
Further, the cyclodextrin is one of alpha-cyclodextrin, beta-cyclodextrin and gamma-cyclodextrin or a mixture of at least two of the above cyclodextrins, and the structure of the cyclodextrin is shown as follows:
wherein the number of the repeating units is in the range of 6, 7 and 8.
Further, in the step A, the mass concentration of the NaOH aqueous solution is 20-30%.
Further, in the step a, the organic solvent is at least one of 1, 4-dioxane, dimethyl sulfoxide, N-methylpyrrolidone, N-dimethylformamide and N, N-dimethylacetamide.
Further, in the step B, the reaction temperature is 100-120 ℃, and the reaction time is 8-12 h.
Further, in step A, X on the (a), (b) and (c) haloolefins is terminal.
In step B, the molar ratio of the halogenated olefin in the mixed solution II to the hydroxyl group on the cyclodextrin in the mixed solution I is (0.8-1.5): 1.
Further, in the step D, the halogenated isocyanate is at least one of ethyl chloroisocyanate, ethyl bromoisocyanate, butyl chloroisocyanate and butyl bromoisocyanate.
Further, in step D, the molar ratio of the halogenated isocyanate to the hydroxyl groups on the initial cyclodextrin is (0.8-1.5): 1.
Further, in the step D, the reaction temperature is 30-50 ℃, and the reaction time is 3-12 h.
Further, in step E, the organic base reagent is at least one selected from the following reagents:
imidazole-based organic bases:
pyridine organic base:
and other miscellaneous nitrogen-containing organic bases:
further, in the step F, the used active UV monomer is hydroxyethyl methacrylate, and the mass fraction of the UV monomer in the cyclodextrin UV resin is 10-40%.
The invention also provides a coating, which comprises the following components in percentage by weight:
the sum of the above components is 100%.
Further, the photoinitiator used is at least one of 2-hydroxy-2-methyl-1-phenyl-1-propanone (1173), 1-hydroxycyclohexyl phenyl ketone (184), phenyl bis (2,4, 6-Trimethylbenzoyl) Phosphine Oxide (TPO), 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide (819), and the addition range is 3% -6%.
Further, the defoaming agent is at least one of acrylate-based defoaming agent, organosilicon-based defoaming agent and fluorocarbon-based defoaming agent, and the addition amount is 0.2% -0.3%.
Furthermore, the wetting dispersant is polyester/polyether high molecular weight block polymer and/or organosilicon wetting dispersant, and the addition amount is 0.4-0.8%.
Furthermore, the anti-settling agent is mainly at least one of fumed silica, polyurea and polyamide, and the addition amount is 0.2-0.4%.
Further, the flatting agent is one or two of polyacrylate and polysiloxane, and the addition amount is 0.5% -1%.
Furthermore, the pigment and the filler are at least one of talcum powder, calcium carbonate, titanium dioxide and transparent powder.
Further, the reactive diluent is at least one of the following diluents: hydroxyethyl methacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, 1, 6-hexanediol diacrylate, trihydroxymethyl propane triacrylate.
Compared with the prior art, the invention has the following beneficial effects:
(a) the structure of the double bond part of the cyclodextrin modified resin is adjustable, the length of a chain segment carbon chain, an aliphatic chain and an aromatic chain can be adjusted according to the performance requirements of materials, the cyclodextrin modified resin has the characteristic of structural diversity, and the flexibility or rigidity of the chain segment can be adjusted, so that the control of the structure-activity relationship of the materials is realized; and the preparation process is simple and the conditions are mild.
(b) The cyclodextrin modified resin has carbamate groups simultaneously in the structure, so that the material can integrate the characteristics of polyurethane in performance; meanwhile, the positive and negative ion structures of the material can strengthen the physical and chemical properties of the material, and the ionic liquid has the advantages of thermal stability, chemical stability, low viscosity, adjustable water/oil solubility and the like, and has excellent comprehensive performance.
(c) The prepared coating has natural, green and degradable film forming substances, is clean, low-carbon and rich in source.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
Example 1
A preparation method of ionic liquid cyclodextrin-based UV resin comprises the following steps:
A. dissolving cyclodextrin in 10% NaOH aqueous solution to obtain mixed solution I, and adding halogenated olefin
Dissolving in dimethyl sulfoxide (DMSO) to obtain mixed solution II;
B. slowly dropwise adding the mixed solution II into the mixed solution I, heating to 50 ℃, and reacting for 4 hours; the molar ratio of the halogenated olefin in the mixed solution II to the hydroxyl on the cyclodextrin in the mixed solution I is 0.2: 1;
C. after the reaction is finished, cooling to room temperature, separating liquid, taking organic phase solution, washing the organic phase solution to be neutral by deionized water, and drying to obtain a product;
D. dissolving the dried product in an organic solvent dimethyl sulfoxide, dissolving ethyl chloroisocyanate in the same organic solvent, slowly dripping the ethyl chloroisocyanate solution into the solution of the dried product, and reacting for 4 hours at the temperature of 20 ℃; the molar ratio of the ethyl chloroisocyanate to the hydroxyl groups on the initial cyclodextrin is 0.3: 1;
E. continuously adding an organic alkali reagent, reacting for 8 hours at the temperature of 50 ℃, and separating to obtain a final product;
F. and dissolving the final product in active UV monomer hydroxyethyl methacrylate to obtain the ionic liquid cyclodextrin UV resin.
Example 2
A preparation method of ionic liquid cyclodextrin-based UV resin comprises the following steps:
A. dissolving cyclodextrin in 20% NaOH aqueous solution to obtain mixed solution I, and adding halogenated olefin
Dissolving in an organic solvent N-methyl pyrrolidone to obtain a mixed solution II;
B. slowly dropwise adding the mixed solution II into the mixed solution I, heating to 100 ℃, and reacting for 8 hours; the molar ratio of the halogenated olefin in the mixed solution II to the hydroxyl on the cyclodextrin in the mixed solution I is 0.8: 1;
C. after the reaction is finished, cooling to room temperature, separating liquid, taking organic phase solution, washing the organic phase solution to be neutral by deionized water, and drying to obtain a product;
D. dissolving the dried product in an organic solvent N-methylpyrrolidone, dissolving ethyl bromoisocyanate in the same organic solvent, slowly dripping the ethyl bromoisocyanate solution into the dried product, and reacting for 3 hours at the temperature of 30 ℃; the molar ratio of the ethyl bromoisocyanate to the hydroxyl groups on the initial cyclodextrin is 0.8: 1;
E. continuously adding an organic alkali reagent, reacting for 6 hours at the temperature of 60 ℃, and separating to obtain a final product;
F. and dissolving the final product in active UV monomer hydroxyethyl methacrylate to obtain the ionic liquid cyclodextrin UV resin.
Example 3
A preparation method of ionic liquid cyclodextrin-based UV resin comprises the following steps:
A. dissolving cyclodextrin in 30 wt% NaOH aqueous solution to obtain mixed solution I, and adding halogenated olefin
Dissolving in an organic solvent N, N-dimethylformamide to obtain a mixed solution II;
B. slowly dropwise adding the mixed solution II into the mixed solution I, heating to 120 ℃, and reacting for 12 hours; the molar ratio of the halogenated olefin in the mixed solution II to the hydroxyl on the cyclodextrin in the mixed solution I is 1.5: 1;
C. after the reaction is finished, cooling to room temperature, separating liquid, taking organic phase solution, washing the organic phase solution to be neutral by deionized water, and drying to obtain a product;
D. dissolving the dried product in an organic solvent N, N-dimethylformamide, dissolving butyl bromoisocyanate in the same organic solvent, slowly dropwise adding the butyl bromoisocyanate solution to the dried product, and reacting at the temperature of 50 ℃ for 12 hours; the molar ratio of butyl bromoisocyanate to hydroxyl on the initial cyclodextrin is 1.5: 1;
E. continuously adding an organic alkali reagent, reacting for 5 hours at the temperature of 50 ℃, and separating to obtain a final product;
F. and dissolving the final product in active UV monomer hydroxyethyl methacrylate to obtain the ionic liquid cyclodextrin UV resin.
Example 4
A preparation method of ionic liquid cyclodextrin-based UV resin comprises the following steps:
B. slowly dropwise adding the mixed solution II into the mixed solution I, heating to 150 ℃, and reacting for 24 hours; the molar ratio of the halogenated olefin in the mixed solution II to the hydroxyl on the cyclodextrin in the mixed solution I is 2: 1;
C. after the reaction is finished, cooling to room temperature, separating liquid, taking organic phase solution, washing the organic phase solution to be neutral by deionized water, and drying to obtain a product;
D. dissolving the dried product in an organic solvent 1, 4-dioxane, dissolving butyl chloroisocyanate in the same organic solvent, slowly dripping the butyl chloroisocyanate solution into the dried product, and reacting at the temperature of 80 ℃ for 24 hours; the molar ratio of the butyl chloroisocyanate to the hydroxyl on the initial cyclodextrin is 3: 1;
E. continuously adding an organic alkali reagent, reacting for 4 hours at the temperature of 80 ℃, and separating to obtain a final product;
F. and dissolving the final product in active UV monomer hydroxyethyl methacrylate to obtain the ionic liquid cyclodextrin UV resin.
EXAMPLE 5
The coating comprises the following components in parts by weight:
according to the formula, the coating is sprayed on the surface of the fraxinus mandshurica wood according to a mechanical arm spraying method, the production efficiency can be greatly improved through rapid ultraviolet curing, and the performance detection result is shown in table 1.
The result shows that after the formula is coated by a mechanical arm, the leveling property and the adhesive force are excellent after the formula is cured by UV, the base material can be effectively protected, and the decorative aesthetic feeling is improved.
Example 6
The coating comprises the following components in parts by weight:
the formula sprays the coating on the surface of the fraxinus mandshurica wood according to an electrostatic spraying method, and the production efficiency can be greatly improved through rapid ultraviolet curing, and the performance detection result is shown as follows.
The results show that the formulation after electrostatic coating has excellent defoaming and adhesion after UV curing.
Example 7
The coating comprises the following components in parts by weight:
the formula is used for spraying the coating on the surface of the fraxinus mandshurica wood according to a mechanical spraying method, the production efficiency can be greatly improved through the rapid ultraviolet curing, and the performance detection result is shown in table 1.
The result shows that the formula has better comprehensive performance after being coated and subjected to UV curing.
Example 8
The coating comprises the following components in parts by weight:
according to the formula, the coating is coated on the surface of the black walnut wood according to a roller coating method, and the production efficiency can be greatly improved through rapid ultraviolet curing, and the performance detection result is shown in table 1.
The result shows that the formula has better comprehensive performance after being subjected to UV curing after being coated by roller coating.
TABLE 1 examples 5-8 coating Properties
The performance detection is referred to GB/T23999-.
Acid and alkali resistance: the acid condition is acetic acid solution, the concentration is 0.1%; the alkaline condition is sodium carbonate solution, the concentration is 0.1 percent, and the test is carried out for 24 hours; the level of 1 is that the paint film is not damaged or marked; the level 2 is that the paint film has traces and can be recovered; level 3 is traceable and unrecoverable; the 4 th level is the film failure.
The above-mentioned embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solution of the present invention by those skilled in the art should fall within the protection scope defined by the claims of the present invention without departing from the spirit of the present invention.
Claims (8)
1. The coating is characterized by comprising the following components in percentage by weight:
the sum of the components is 100 percent;
the pigment and the filler are pigments and/or fillers;
the preparation method of the ionic liquid cyclodextrin-based UV resin comprises the following steps:
A. dissolving cyclodextrin in 10-50% of NaOH aqueous solution by mass fraction to obtain a mixed solution I, and dissolving halogenated olefin in an organic solvent to obtain a mixed solution II; the organic solvent is at least one of 1, 4-dioxane, dimethyl sulfoxide, N-methyl pyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide;
B. slowly dropwise adding the mixed solution II into the mixed solution I, heating to 50-150 ℃, and reacting for 4-24 h; the molar ratio of the halogenated olefin in the mixed solution II to the hydroxyl on the cyclodextrin in the mixed solution I is (0.2-2): 1;
C. after the reaction is finished, cooling to room temperature, separating liquid, taking organic phase solution, washing the organic phase solution to be neutral by deionized water, and drying to obtain a product;
D. dissolving the dried product in an organic solvent, dissolving halogenated isocyanate in the same organic solvent, slowly dripping the halogenated isocyanate solution into the dried product, and reacting at the temperature of 20-80 ℃ for 4-24 h; the molar ratio of the halogenated isocyanate to the hydroxyl groups on the initial cyclodextrin is (0.3-3) to 1;
E. continuously adding an organic alkali reagent, reacting for 3-12h at the temperature of 30-100 ℃, and separating to obtain a final product;
F. dissolving the final product in an active UV monomer to obtain ionic liquid cyclodextrin UV resin;
the halogenated olefin is selected from at least one of the following compounds:
(a) halogenated olefin having one double bond: XCnH2n-1Wherein: x ═ Cl, Br, or I; n is more than or equal to 3 and less than or equal to 20;
(b) halogenated olefins containing two double bonds: XCnH2n-3Wherein: x ═ Cl, Br, or I; n is more than or equal to 5 and less than or equal to 20;
(c) halogenated olefins containing three double bonds: XCnH2n-5Wherein: x ═ Cl, Br, or I; n is more than or equal to 5 and less than or equal to 20;
(d) aromatic olefins containing double bonds:
2. the coating of claim 1, wherein in step a, the mass concentration of the NaOH aqueous solution is 20% to 30%; the reaction temperature is 100-120 ℃, and the reaction time is 8-12 h.
3. The coating of claim 1 wherein in step a, X is at an end group on said (a), (b) and (c) haloolefins.
4. The paint according to claim 1, wherein in step D, the halogenated isocyanate is at least one of ethyl chloroisocyanate, ethyl bromoisocyanate, butyl chloroisocyanate and butyl bromoisocyanate; the molar ratio of the halogenated isocyanate to the hydroxyl groups on the initial cyclodextrin is (0.8-1.5): 1.
5. The coating according to claim 1, characterized in that, in step E, said organic alkaline agent is selected from at least one of the following agents:
imidazole-based organic bases:
pyridine organic base:
and other miscellaneous nitrogen-containing organic bases:
6. the coating of claim 1, wherein: in the step F, the used active UV monomer is hydroxyethyl methacrylate, and the mass fraction of the UV monomer in the cyclodextrin UV resin is 10-40%.
7. The coating according to claim 1, comprising the following components in weight percent:
the sum of the above components is 100%.
8. The coating of claim 1, wherein: the photoinitiator is at least one of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 1-hydroxycyclohexyl phenyl ketone, phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide and 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide;
the defoaming agent is at least one of acrylate-based defoaming agent, organosilicon defoaming agent and fluorocarbon defoaming agent;
the wetting dispersant is a polyester/polyether high molecular weight block polymer and/or an organic silicon wetting dispersant;
the anti-settling agent is at least one of fumed silica, polyurea and polyamide;
the flatting agent is one or two of polyacrylate and polysiloxane;
the pigment and the filler are at least one of talcum powder, calcium carbonate, titanium dioxide and transparent powder;
the active diluent is at least one of the following diluents: hydroxyethyl methacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, 1, 6-hexanediol diacrylate, trihydroxymethyl propane triacrylate.
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