CN112266651A - Application of propenyl phenol compound in preparation of light-colored raw lacquer, light-colored raw lacquer and preparation method thereof - Google Patents
Application of propenyl phenol compound in preparation of light-colored raw lacquer, light-colored raw lacquer and preparation method thereof Download PDFInfo
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- CN112266651A CN112266651A CN202011152613.9A CN202011152613A CN112266651A CN 112266651 A CN112266651 A CN 112266651A CN 202011152613 A CN202011152613 A CN 202011152613A CN 112266651 A CN112266651 A CN 112266651A
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- raw lacquer
- light
- propenyl
- urushiol
- colored
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- 239000004922 lacquer Substances 0.000 title claims abstract description 137
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- -1 propenyl phenol compound Chemical class 0.000 title claims description 35
- 229930015698 phenylpropene Natural products 0.000 title claims description 26
- QARRXYBJLBIVAK-UEMSJJPVSA-N 3-[(8e,11e)-pentadeca-8,11-dienyl]benzene-1,2-diol;3-[(8e,11e)-pentadeca-8,11,14-trienyl]benzene-1,2-diol;3-[(8e,11e,13e)-pentadeca-8,11,13-trienyl]benzene-1,2-diol;3-[(e)-pentadec-8-enyl]benzene-1,2-diol;3-pentadecylbenzene-1,2-diol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O.CCCCCC\C=C\CCCCCCCC1=CC=CC(O)=C1O.CCC\C=C\C\C=C\CCCCCCCC1=CC=CC(O)=C1O.C\C=C\C=C\C\C=C\CCCCCCCC1=CC=CC(O)=C1O.OC1=CC=CC(CCCCCCC\C=C\C\C=C\CC=C)=C1O QARRXYBJLBIVAK-UEMSJJPVSA-N 0.000 claims abstract description 58
- RMTXUPIIESNLPW-UHFFFAOYSA-N 1,2-dihydroxy-3-(pentadeca-8,11-dienyl)benzene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1O RMTXUPIIESNLPW-UHFFFAOYSA-N 0.000 claims abstract description 57
- IYROWZYPEIMDDN-UHFFFAOYSA-N 3-n-pentadec-8,11,13-trienyl catechol Natural products CC=CC=CCC=CCCCCCCCC1=CC=CC(O)=C1O IYROWZYPEIMDDN-UHFFFAOYSA-N 0.000 claims abstract description 57
- DQTMTQZSOJMZSF-UHFFFAOYSA-N urushiol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O DQTMTQZSOJMZSF-UHFFFAOYSA-N 0.000 claims abstract description 57
- 238000003756 stirring Methods 0.000 claims abstract description 21
- WHGXZPQWZJUGEP-UHFFFAOYSA-N 2-prop-1-enylphenol Chemical class CC=CC1=CC=CC=C1O WHGXZPQWZJUGEP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 238000005303 weighing Methods 0.000 claims abstract description 10
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 18
- 239000003085 diluting agent Substances 0.000 claims description 13
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 13
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- 238000010008 shearing Methods 0.000 claims description 10
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 9
- 239000005770 Eugenol Substances 0.000 claims description 9
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 9
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- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000002383 tung oil Substances 0.000 claims description 6
- 125000006017 1-propenyl group Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 241000723422 Catalpa Species 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
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- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 claims description 4
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- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 3
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims description 3
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 239000003973 paint Substances 0.000 abstract description 45
- 108090000790 Enzymes Proteins 0.000 abstract description 7
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 35
- 150000003254 radicals Chemical class 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- RGIBXDHONMXTLI-UHFFFAOYSA-N chavicol Chemical compound OC1=CC=C(CC=C)C=C1 RGIBXDHONMXTLI-UHFFFAOYSA-N 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 3
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- OCNIKEFATSKIBE-NSCUHMNNSA-N (e)-4-(4-hydroxyphenyl)but-3-en-2-one Chemical compound CC(=O)\C=C\C1=CC=C(O)C=C1 OCNIKEFATSKIBE-NSCUHMNNSA-N 0.000 description 2
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007385 chemical modification Methods 0.000 description 2
- DKZBBWMURDFHNE-NSCUHMNNSA-N coniferyl aldehyde Chemical compound COC1=CC(\C=C\C=O)=CC=C1O DKZBBWMURDFHNE-NSCUHMNNSA-N 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
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- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 2
- AUJXJFHANFIVKH-GQCTYLIASA-N trans-methylferulate Chemical compound COC(=O)\C=C\C1=CC=C(O)C(OC)=C1 AUJXJFHANFIVKH-GQCTYLIASA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 2
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- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- NFDFQCUYFHCNBW-SCGPFSFSSA-N dienestrol Chemical compound C=1C=C(O)C=CC=1\C(=C/C)\C(=C\C)\C1=CC=C(O)C=C1 NFDFQCUYFHCNBW-SCGPFSFSSA-N 0.000 description 1
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- 229940090028 ethyl linolenate Drugs 0.000 description 1
- JYYFMIOPGOFNPK-UHFFFAOYSA-N ethyl linolenate Natural products CCOC(=O)CCCCCCCC=CCC=CCC=CCC JYYFMIOPGOFNPK-UHFFFAOYSA-N 0.000 description 1
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- JTLOUXXZZFFBBW-UHFFFAOYSA-N isoferulic acid methyl ester Natural products COC(=O)C=CC1=CC=C(OC)C(O)=C1 JTLOUXXZZFFBBW-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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Images
Classifications
-
- 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
Abstract
The invention relates to the technical field of raw lacquer, and discloses an application of propenyl phenol compounds in preparing light-colored raw lacquer; discloses light-colored raw lacquer, which comprises raw lacquer and propenyl phenol compounds, wherein the propenyl phenol compounds account for 7-28 wt% of the urushiol content. Discloses a preparation method, which comprises the following steps: determining the urushiol content in the raw lacquer; weighing raw lacquer, adding propenyl phenol compounds under the protection of gas, and sequentially stirring and filtering to obtain light-color raw lacquer. The light-color raw lacquer prepared by the invention has the characteristics of light paint film color, high transparency, strong flexibility, high hardness, environmental protection and the like, and retains the characteristic of biological enzyme catalytic curing.
Description
Technical Field
The invention belongs to the technical field of raw lacquer, and particularly relates to application of propenyl phenol compounds in preparation of light-colored raw lacquer, the light-colored raw lacquer and a preparation method thereof.
Background
Raw lacquer, also known as natural lacquer, Chinese lacquer, earth lacquer and Chinese lacquer, is a natural resin coating which is a white viscous water-in-oil emulsion flowing out of the bast skin of a lacquer tree and is prepared by processing, and belongs to a pure natural coating product. The natural raw lacquer is a special resource in China, is natural lacquer sap artificially cut from lacquer trees, mainly contains urushiol, laccase, tree gum, water and the like, and is the only natural coating with biological enzyme catalytic curing characteristic used by human beings.
The raw lacquer is known as the king of coating because of the unique excellent performance, but the raw lacquer also has the defects of deep color of the coating, high viscosity, difficult construction, poor sensitization, poor alkali resistance and the like. Particularly, the natural color of a raw lacquer film is dark brown to black, and the color of a lacquered device and furniture is monotonous, so that the application range of the raw lacquer is seriously restricted, and the market competitiveness is further influenced.
Therefore, the raw lacquer light-coloring technology is an important research and development direction of the whole industry, but the problem is not solved well for a long time. The reason why the color of the raw lacquer is darker after film forming is mainly that the alkyl catechol compound generates quinone under the catalysis of laccase, and the quinone has stronger absorption in the visible light wavelength range. Although the chroma can be reduced to a certain extent by adding some natural diluents (such as rosin, gamboge and the like) or by pre-polymerizing and refining raw lacquer, the color of a lacquer film is dark, and the requirements for preparing varnish and colored lacquer cannot be met.
At present, the light-colored raw lacquer preparation technology focuses on the aspect of chemical modification, and the aim of color reduction is achieved mainly by introducing other active groups and inhibiting the generation of benzoquinone. However, the chemically modified raw lacquer is free from the biological enzyme catalysis mechanism of the raw lacquer, and is a synthetic coating obtained by chemical modification on the basis of using alkyl catechol as a molecule, and a high-VOC (volatile organic compound) diluting solvent and a curing agent are required, so that the chemically modified raw lacquer is not comparable to the natural raw lacquer in terms of environmental protection and human health.
In recent years, the influence of the traditional chemical coating on the environment and human health is concerned, so that the green coating becomes a hot point for development and has wide market prospect. The green coating refers to energy-saving and low-pollution water-based coatings, powder coatings, high-solid content coatings (or solvent-free coatings), radiation curing coatings and the like, and has the characteristics of low total organic Volatile Organic Compounds (VOC), low solvent or no solvent. The natural raw lacquer is a water-in-oil emulsion composed of urushiol, laccase, gum, water and the like, the solid content is up to 60% -75%, the organic volatilization amount is extremely low, and the natural raw lacquer is a natural green coating.
Therefore, a preparation technology of the light-color raw lacquer is sought, so that the preparation technology can keep the advantages of natural environmental protection, low VOC (volatile organic compound) emission and high solid content, can meet the manufacturing requirements of various varnishes and colored lacquers, has great significance for widening the application field of the raw lacquer, and can also conform to the requirement of the era of sustainable development.
Disclosure of Invention
Aiming at the defects of dark color, difficult color matching and the like of a raw lacquer film of the existing raw lacquer, the invention aims to provide an allyl phenol compound for preparing light-color raw lacquer, the prepared light-color raw lacquer has the characteristics of light color, high transparency, strong flexibility, high hardness, environmental protection and the like of the paint film, the characteristic of biological enzyme catalytic curing is kept, and the allyl phenol compound can be widely applied to the fields of furniture floor finishing, industrial art, building decoration and the like.
Therefore, the first object of the present invention is to provide the use of propenyl phenol compound in the preparation of light-colored raw lacquer, the structural formula of the propenyl phenol compound is shown as follows,
wherein R is1And R2Can be propenyl, propenyl derivative, hydrogen or C1-C3 alkoxy;
at R1And R2Of these, one and only one group is propenyl, which is 1-propenyl or 2-propenyl.
The second purpose of the invention is to provide a light-colored raw lacquer, which comprises raw lacquer and propenyl phenol compounds in parts by weight, wherein the propenyl phenol compounds account for 7-28% of the weight of urushiol in the raw lacquer.
The third purpose of the invention is to provide a preparation method of light-colored raw lacquer, which comprises the following steps:
determining the urushiol content in the raw lacquer; weighing raw lacquer, adding propenyl phenol compounds under the protection of gas, and sequentially stirring and filtering to obtain light-color raw lacquer.
Now, the technical mechanism of applying the propenyl phenol compound to the preparation of the light-colored raw lacquer is specifically explained:
< film Forming mechanism of raw paint >
The film forming process of raw lacquer is a biochemical reaction process, laccase is a biocatalyst, urushiol is a reaction substrate of laccase and a reaction medium of film forming polymerization, and raw lacquer is the only biopolymer with practicability of catalyzing polymerization reaction by using the biological enzyme.
Under the aerobic condition, urushiol in raw lacquer forms urushiol free radical under the action of laccase, then non-enzymatic free radical oxidative polymerization reaction is carried out, urushiol dimer, urushiol trimer and urushiol high polymer are formed from urushiol monomer, and finally, urushiol dimer, urushiol high polymer are self-assembled and aggregated through supermolecular interaction to form a continuous lacquer film.
The polymerization process of raw lacquer can be divided into two stages of enzymatic free radical reaction and autoxidation reaction.
Enzymatic free radical reaction stage
The enzymatic free radical reaction of raw lacquer is a reaction that urushiol is oxidized into semiquinone free radical under the catalysis of laccase, mainly comprises free radical substitution reaction and free radical addition reaction, and the specific polymerization path is shown in figure 1.
Firstly, laccase acts on urushiol to generate oxidation reaction to form a urushiol semiquinone free radical, laccase is reduced, the reduced laccase is oxidized in the air, and then the laccase with oxidation activity is recovered.
Radical substitution reaction pathway: the benzene ring of the semiquinone free radical has an active hydrogen, and biphenyl dimers are generated through intermolecular coupling; laccase reoxidizes the biphenyl dimers of urushiol to dibenzofurans.
Free radical addition reaction pathway: the urushiol semi-quinone generates free radical disproportionation reaction to generate urushiol quinone, and the urushiol quinone generates molecular transfer and reacts with unsaturated side chains in the urushiol to generate products of-C-C-coupling and-C-O-C-coupling.
Such enzymatic and radical reactions are repeated, finally allowing the paint film to dry completely.
During the enzymatic free radical reaction of raw lacquer, no matter free radical substitution reaction or free radical addition reaction, the products of-C-C-coupling still have catechol structure, and can be oxidized again into semiquinone and urushiol quinone by laccase or free radical transfer, and the semiquinone and urushiol quinone are difficult to react completely along with the formation of high polymer and supermolecule due to molecular movement and space effect, which is the main reason of darker paint film of raw lacquer, especially the influence of urushiol quinone on color is most obvious. In the free radical addition reaction path, due to-C-O-C-coupling, 1 of 2 urushiol molecules generates ether bonds, residual monophenol can not be oxidized into quinone, and the generated ether bond structure polymer absorbs weakly in a visible light range.
Auto-oxidation reaction stage
After the enzymatic free radical reaction of the raw lacquer, slow auto-oxidative polymerization reaction occurs on the unsaturated side chain of urushiol, so that the paint film can be completely dried and cured, and the reaction at the stage has very little influence on the color of the paint film.
< principles of action of Propenylphenol Compounds >
According to the invention, the allyl phenol compound is added into the raw lacquer, so that the-C-O-C-polymerization reaction can be remarkably promoted, and the raw lacquer can further react with residual urushiol quinone completely, thereby realizing the light color of the raw lacquer in the enzyme-catalyzed polymerization reaction. After the propenyl phenol compound is added, the original polymerization mechanism is not changed, and the polymerization becomes more complicated due to the introduction of a new molecule with polymerization activity, and the specific polymerization path is shown in fig. 2.
Firstly, laccase acts on urushiol to generate oxidation reaction to form urushiol semiquinone free radical, laccase is reduced, the reaction path of free radical substitution is consistent with the original mechanism, and biphenyl type and dibenzofuran type polymers are generated.
Free radical addition reaction stage: the urushiol quinone is transferred, on one hand, the urushiol quinone reacts with unsaturated side chains in the urushiol to generate-C-C-coupling and-C-O-C-coupling products; on the other hand, the allyl phenol is also subjected to-C-O-C-coupling with a side chain double bond in an allyl phenol molecule, and the rearrangement generates a structure similar to p-benzoquinone, the structure is unstable and easy to react with a urushiol side chain double bond, and finally a-C-O-C-coupled product is generated; the catechol structure existing on the-C-C-coupled product can be oxidized into semiquinone and urushiol quinone again by laccase, because of smaller molecular weight, the propenyl phenol which does not participate in the reaction can slowly diffuse in the three-dimensional network polymer, and reacts with the generated urushiol quinone to form-C-O-C-coupled product, and the urushiol quinone in the finally dried paint film is less.
The raw lacquer is refined at the temperature ranging from room temperature to 40 ℃ under the condition of sufficient oxygen, the molecular movement is accelerated under the action of relatively high temperature and external force through continuous stirring, and the sufficient oxygen accelerates the generation of urushiol polymers, so that the method is favorable for the reaction of-C-O-C-on one hand, and can promote the reaction of urushiol quinone on the-C-C-structure polymers on the other hand. Therefore, the paint film color of the refined raw lacquer is better than that of the raw lacquer.
The boiling point of the propenyl phenol compound is above 230 ℃, the propenyl phenol compound also participates in a film forming reaction as an active molecule, and the volatilization amount of the propenyl phenol compound is extremely low in the film forming process and after film forming.
The invention has the beneficial effects that:
the propenyl phenol compound is used for preparing the light-color raw lacquer, the prepared light-color raw lacquer has the characteristics of light color, high transparency, strong flexibility, high hardness, green environmental protection and the like, the characteristic of biological enzyme catalytic curing is retained, and the light-color raw lacquer can be widely applied to the fields of furniture floor finishing, industrial art, building decoration and the like.
Drawings
FIG. 1 is a schematic diagram of the film forming mechanism of raw lacquer in the summary of the invention;
FIG. 2 is a schematic diagram showing the mechanism of film formation of a light-colored raw lacquer in the summary of the invention;
FIG. 3 is a graph showing the light transmittance in the wavelength range of the visible region of the paint films of examples 1 to 2 and comparative examples 1 to 3;
FIG. 4 is a scan of the paint films of examples 1-2 and comparative examples 1-3;
note: a 1-example 1; a 2-example 2; b1-comparative example 1; b2-comparative example 2; b3-comparative example 3; c-reference;
in FIG. 4, the scanned paint film image of each test sample is gray-scale processed, and if the original is needed, the applicant can provide the original.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The invention provides the application of propenyl phenol compound in preparing light-colored raw lacquer, the structural formula of the propenyl phenol compound is shown as (I),
wherein R is1And R2Can be propenyl, propenyl derivative, hydrogen or C1-C3 alkoxy;
at R1And R2Of these, one and only one group is propenyl, which is 1-propenyl or 2-propenyl.
R1Or R2In the case of propenyl or a propenyl derivative, the substitution may be carried out at any position on the group.
Specifically, the method comprises the following steps: r1When it is 1-propenyl or 2-propenyl, R2Is H, methoxy, ethoxy or propoxy; or R1When H, methoxy, ethoxy or propoxy is present, R2Is 1-propenyl or 2-propenyl.
In the present invention, R1And R2Can be propenyl, hydrogen or methoxy.
In the invention, the propenyl phenol compound is ferulic acid or an ester thereof, eugenol or isoeugenol. The propenyl phenol compound may also be selected from 2-allyl phenol, vanillin acetone, 4-hydroxy-3-methoxycinnamaldehyde, 4-isopropenylphenol, 4-allyl phenol, p-hydroxybenzylideneacetone, p-hydroxycinnamic acid and its ester.
Secondly, the invention provides a light-color raw lacquer, which comprises raw lacquer and propenyl phenol compounds in parts by weight, wherein the propenyl phenol compounds account for 7-28% of the weight of urushiol in the raw lacquer.
In the invention, the propenyl phenol compound accounts for 12-20% of the urushiol in the raw lacquer in parts by weight.
The third, the invention provides a preparation method of light-colored raw lacquer, comprising the following steps: weighing raw lacquer, adding propenyl phenol compounds under the protection of gas, and sequentially stirring, shearing at high speed and filtering to obtain light-colored raw lacquer.
In the invention, under the condition that no reactive diluent is added, the color of a paint film prepared from the light-color raw lacquer becomes gradually lighter after the paint film is dried, and the paint film tends to be stable within 2-4 weeks; with the addition of reactive diluents, the color of the paint film after tack-free is better than the stable chroma of the paint film sample without the addition, because: on one hand, the molecular concentration of the long alkene is increased to promote the-C-O-C-coupling reaction, on the other hand, the reaction activity of the reactive diluent is weaker than that of urushiol and propenyl phenol, and a solvent effect is generated in a three-dimensional net space during the drying process and after film forming, the molecular diffusion of the propenyl phenol is accelerated, and the complete reaction with urushiol quinone can be effectively promoted.
In the invention, the active diluent comprises one or more of tung oil, linseed oil and catalpa oil; or the active diluent is fatty acid methyl ester or ethyl ester, and the fatty acid methyl ester or ethyl ester is prepared by taking tung oil, linseed oil or catalpa oil as raw materials.
In the invention, the reactive diluent accounts for 0-40% of the weight of urushiol in the raw lacquer.
In the invention, the repeated times of continuous stirring are 2-4 times and 2 min/time, the rotating speed is 6000 r/min-12000 r/min, and the temperature is not higher than 60 ℃.
In the invention, during preparation, the urushiol content in the raw lacquer or the heating decrement of the refined raw lacquer is firstly measured, and the measuring method refers to GB/T14703-2008.
In the present invention, raw lacquer is used which is derived from raw lacquer or refined raw lacquer of Rhus sources of china, japan and korea (Rhus vernicifera), Rhus sources of taiwan of vietnam and china (Rhus succanaea), or Rhus sources of thailand, burmese and srilanka (melanorrhaea usata). Rhus vernicifera mainly contains 3-pentadecane triassinol, Rhus succincana mainly contains 3-heptadecane triassinol, Melanorrhoea usitata mainly contains 4-C17-C18 alkane dienol, and the film-forming polymerization mechanism is similar despite some differences in molecular structure.
In the invention, the blending liquid obtained after the continuous stirring is water-in-oil emulsion, and the particle size range of the water-in-oil emulsion is 1-10 mu m.
In the invention, positive pressure filtration is adopted, and the filtration pore size is 25-120 μm.
In the present invention, the protective gas is nitrogen.
In the invention, the temperature in high-speed shearing is not higher than 60 ℃.
< example >
Example 1
A light-colored raw lacquer and a preparation method thereof comprise the following steps:
(1) determining the urushiol content in the raw lacquer by referring to GB/T14703-2008, and determining that the urushiol content in the raw lacquer (Rhus vernicifera) sample is 68.5%;
(2) weighing 101.3g of the raw lacquer to a beaker, blowing nitrogen above the liquid surface, slowly adding 12.2g of isoeugenol, stirring for 2min at the speed of 60r/min, then adding 12.0g of linseed oil, and continuously stirring for 3 min;
(3) shearing at 8000rpm for 3 times, 2 min/time, and 2min at interval to obtain stable water-in-oil emulsion at 40 deg.C;
(4) and (5) filtering by using a nylon filter cloth of 200 meshes under forward pressure to obtain the light-colored raw lacquer.
Example 2
A light-colored raw lacquer and a preparation method thereof comprise the following steps:
(1) determining the urushiol content in the raw lacquer by referring to GB/T14703-2008, and determining that the urushiol content in the raw lacquer (Rhus vernicifera) sample is 68.5%;
(2) weighing 100.1g of the raw lacquer to a beaker, blowing nitrogen above the liquid surface, slowly adding 12.0g of isoeugenol, and stirring for 3min at the speed of 60 r/min;
(3) shearing at 10000rpm of an internal cutting homogenizer for 2 times, 1 min/time and 3min at intervals to obtain stable water-in-oil emulsion, wherein the temperature of the emulsion is controlled at 40 ℃;
(4) and (3) filtering by adopting rapid filter paper (with the pore size distribution of 80-120 mu m) under positive pressure to obtain the light-colored raw lacquer.
Example 3
A light-colored raw lacquer and a preparation method thereof comprise the following steps:
(1) the urushiol content in the raw lacquer is determined by referring to GB/T14703-2008, and the urushiol content in the raw lacquer (Rhus vernicifera) sample is determined to be 65.1 percent.
(2) Weighing 305.9g of the raw lacquer into a beaker, blowing nitrogen above the liquid surface, slowly adding 24.5g of eugenol, stirring for 5min at the speed of 60r/min, then adding 54.0g of tung oil methyl ester, and continuously stirring for 5 min;
(3) transferring into an external cutting homogenizer, blowing nitrogen into the container, sealing, shearing at 12000rpm for 2 times, 1 min/time, and 2min at intervals to obtain stable water-in-oil emulsion at 40 deg.C;
(4) and (3) filtering by adopting medium-speed filter paper (with the pore size distribution of 30-50 mu m) under forward pressure to obtain the low-viscosity light-colored raw lacquer.
Example 4
A light-colored refined raw lacquer and a preparation method thereof comprise the following steps:
(1) the urushiol content in the raw lacquer is determined according to GB/T14703-2008, and the heating loss of a refined raw lacquer (Rhus vernicifera) sample is determined to be 5.6 percent;
(2) weighing 212.1g of the refined raw lacquer into a beaker, blowing nitrogen above the liquid surface, slowly adding 14.2g of 2-allylphenol, stirring for 5min at the speed of 100r/min, adding 28.5g of ethyl linolenate, and continuously stirring for 10 min;
(3) transferring into an external cutting homogenizer, blowing nitrogen into the container, sealing, shearing at 10000rpm for 3 times, 1 min/time, and 3min at intervals to obtain stable water-in-oil emulsion, wherein the temperature of the emulsion is controlled at 40 deg.C;
(4) adopting rapid filter paper (pore size distribution is 80-120 μm) to filter by positive pressure, and obtaining light-colored refined raw lacquer.
Example 5
A light-colored raw lacquer and a preparation method thereof comprise the following steps:
(1) the urushiol content in the raw lacquer is determined by referring to GB/T14703-2008, and the urushiol content in the raw lacquer (Rhus succinedaea) sample is 49.3 percent.
(2) Weighing 102.2g of the raw lacquer into a beaker, blowing nitrogen above the liquid surface, slowly adding 9.9g of methyl ferulate, stirring for 3min at the speed of 80r/min, adding about 10.1g of tung oil, and continuously stirring for 5 min;
(3) shearing at 10000rpm of an internal cutting homogenizer for 3 times, 1 min/time and 3min at intervals to obtain stable water-in-oil emulsion, wherein the temperature of the emulsion is controlled at 40 ℃;
(4) and (3) filtering by adopting rapid filter paper (with the pore diameter distribution of 80-120 mu m) under forward pressure to obtain the light-colored raw lacquer.
Example 6
A light-colored raw lacquer and a preparation method thereof comprise the following steps:
(1) determining the urushiol content in the raw lacquer by referring to GB/T14703-2008, and determining that the urushiol content in the raw lacquer (Melanorrhoea useitata) sample is 51.7 percent;
(2) weighing 103.4g of the raw lacquer into a beaker, blowing nitrogen above the liquid surface, slowly adding 11.0g of 4-isopropenylphenol, stirring for 5min at the speed of 80r/min, then adding about 7.3g of catalpa oil, and continuously stirring for 5 min;
(3) shearing at 10000rpm for 4 times, 1 min/time and 2min at interval by an internal cutting homogenizer to obtain stable water-in-oil emulsion, wherein the emulsion temperature is controlled at 40 ℃;
(4) and (5) filtering by using a nylon filter cloth of 200 meshes under forward pressure to obtain the high-viscosity light-colored raw lacquer.
Example 7
This example differs from example 3 in that eugenol is replaced by vanillin acetonide; (2) stirring for 5min at medium stirring parameter of 80r/min, or selecting 100 r/min.
Example 8
This example differs from example 3 in that eugenol is replaced by 4-hydroxy-3-methoxycinnamaldehyde.
Example 9
This example differs from example 3 in that eugenol is replaced by 4-allylphenol.
Example 10
This example differs from example 3 in that eugenol is replaced by p-hydroxybenzylideneacetone.
Example 11
This example differs from example 3 in that eugenol is replaced by p-hydroxycinnamic acid.
Example 12
This example differs from example 3 in that eugenol is replaced by p-hydroxycinnamate.
<Test examples>
(1) Determination of film transmittance
Test samples: examples 1 to 2, comparative example 1-raw lacquer, comparative example 2-refined raw lacquer, comparative example 3-clear lacquer (japan).
The test method comprises the following steps: the transparency of the paint film is compared by adopting a visible spectrophotometry, the samples are respectively and uniformly coated on quartz glass sheets (50 x 1mm) by using a wire bar coater (50 mu m), the quartz glass sheets are placed in a constant temperature and humidity box with the temperature of 25 +/-1 ℃/humidity of 75 +/-2 percent, the quartz glass sheets are taken out after 30 days, the quartz glass sheets are taken as reference, the quartz glass sheets are placed in a film sample frame, the wavelength interval is set to be 1nm, and a light transmittance spectrogram in the wavelength range of a visible light region (400 nm-760 nm) is measured, and is shown in figure 3.
The average values were calculated from the transmittance at all wavelengths and each colorband in fig. 3, and the specific data are shown in table 1.
The average light transmittance values of the paint films of example 1, example 2, comparative example 1, comparative example 2 and comparative example 3 in the visible light range (400 nm-760 nm) are 72.47%, 64.38%, 49.89%, 24.98% and 8.98%, respectively, the light-color raw paint films of example 1 and example 2 are obviously better than the paint films of comparative examples 1-3, and the light transmittance of the light-color raw paint of example 1 is better than that of the light-color raw paint of example 2. The higher the light transmittance of the paint film in the visible light region, the better the light transmittance of the paint film, and the lighter the chroma of the paint film obtained from the raw paint.
② the light-colored raw lacquer films of examples 1 and 2 have a significantly better light transmittance than the lacquer films of comparative examples 1 to 3 as the wavelength is closer to the ultraviolet band.
TABLE 1 visible wavelength range of the film transmittance
(2) Determination of the paint film Properties
Sample preparation: examples 1-6, comparative examples 1-3.
Specifically, examples 1 to 2, examples 4 to 6, comparative examples 1 to 3 were paint films prepared using a wire bar coater (50 μm), and example 3 was a wet film of 50. + -.1 μm prepared using a high-pressure airless sprayer, placed in a constant temperature and humidity cabinet at a temperature of 25. + -. 1 ℃/humidity of 75%. + -. 2%, taken out after 30 days, and each performance index was measured.
Example 3 the film forming treatment was carried out by a high-pressure airless sprayer because: the low-viscosity reactive diluent is added in the embodiment 3, so that the viscosity of the light-color raw lacquer can be obviously reduced, the industrial spraying can be carried out, the construction convenience and the construction efficiency of the product can be improved, and a high-pressure airless sprayer is selected.
The results of the paint film property measurements are shown in Table 2.
As can be seen from Table 2, the paint film properties of the example group are superior to those of the comparative example group, which shows that the paint film obtained by adding the propenyl phenol compound into the raw paint has light color, high transparency, high hardness and strong flexibility.
(3) Color contrast of paint film under visible light
Comparative examples 1 to 3 and examples 1 to 2 were each uniformly coated on a glass plate (100 x 1.5mm) using a wire bar coater (50 μm), placed in a constant temperature and humidity cabinet at a temperature of 25 ℃ ± 1 ℃ and a humidity of 75% ± 2%, taken out after 30 days, and scanned on a white background with reference to a blank glass plate, and the scanning pattern is shown in fig. 4.
As can be seen from FIG. 4, the paint films of the examples (with the addition of the propenyl phenol compound) are significantly better in color than the paint films of the comparative examples, and the results show that the addition of the propenyl phenol compound to the raw paint or the refined raw paint can make the raw paint light in color. Compared with the paint prepared in example 2, the paint film of the light-color raw paint added with the reactive diluent (example 1) is better than the paint film of the light-color raw paint not added with the reactive diluent (example 2), and the light-color raw paint added with the reactive diluent has more excellent color reduction effect.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The application of the propenyl phenol compound shown in the formula I in preparing light-colored raw lacquer,
wherein R is1And R2Independently selected from propenyl, propenyl derivatives, hydrogen or C1-C3 alkoxy;
at R1And R2Of these, one and only one group is propenyl, which is 1-propenyl or 2-propenyl.
2. Use of the propenyl phenol compound according to claim 1 in the preparation of raw lacquer with a light colour, characterized in that R is1And R2Can be propenyl, hydrogen or methoxy.
3. Use of an allylphenol compound according to claim 1 in the preparation of a light colored raw lacquer, wherein the allylphenol compound is selected from at least one of ferulic acid, ferulic acid ester, eugenol, or isoeugenol.
4. A light-colored raw lacquer, characterized in that, each component comprises raw lacquer and propenyl phenol compound as claimed in any one of claims 1 to 3, wherein the propenyl phenol compound accounts for 7 to 28 percent of the weight of urushiol in the raw lacquer.
5. A light-colored raw lacquer according to claim 4, characterized in that the propenyl phenol compound accounts for 12 to 20% of the weight of urushiol in the raw lacquer.
6. A process for the preparation of a light-coloured raw lacquer according to claim 4 or 5, characterized in that it comprises the following steps:
weighing raw lacquer, adding propenyl phenol compounds under the protection of gas, and sequentially stirring, shearing at high speed and filtering to obtain light-colored raw lacquer.
7. A process for the preparation of raw lacquer according to claim 6, characterized in that the number of repetitions of stirring is 2 to 4 times, 2 min/time, the rotation speed is 6000 to 12000r/min and the temperature is not higher than 60 ℃.
8. The method of preparing a light-colored raw lacquer according to claim 6, further comprising a reactive diluent comprising at least one of tung oil, linseed oil, or catalpa oil; or fatty acid methyl ester or ethyl ester prepared from tung oil, linseed oil or catalpa oil as raw materials.
9. A process for preparing a light-coloured raw lacquer according to claim 8, characterized in that the reactive diluent constitutes 0-40% by weight of the urushiol in the raw lacquer.
10. The method for producing a light-colored raw lacquer according to claim 6, wherein the blend after the high-speed shearing treatment is a water-in-oil emulsion having a water droplet diameter in the range of 1 μm to 10 μm.
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Effective date of registration: 20231120 Address after: No. 26-15 Xiaonan Street, Junlian Town, Junlian County, Yibin City, Sichuan Province, 645250 Patentee after: Hao Jiasi Address before: No. 1408, unit 1, building 4, No. 366, Ronghua South Road, high tech Zone, Chengdu, Sichuan 610000 Patentee before: Sichuan Shangyu Biotechnology Co.,Ltd. |