CN112538015A - Preparation process of odor-free film-forming additive - Google Patents
Preparation process of odor-free film-forming additive Download PDFInfo
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- CN112538015A CN112538015A CN202011627765.XA CN202011627765A CN112538015A CN 112538015 A CN112538015 A CN 112538015A CN 202011627765 A CN202011627765 A CN 202011627765A CN 112538015 A CN112538015 A CN 112538015A
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- isobutyraldehyde
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- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 239000000654 additive Substances 0.000 title claims abstract description 15
- 230000000996 additive effect Effects 0.000 title claims abstract description 15
- -1 hexadecyl alcohol ester Chemical class 0.000 claims abstract description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- LQZZUXJYWNFBMV-UHFFFAOYSA-N ethyl butylhexanol Natural products CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims abstract description 22
- 230000009965 odorless effect Effects 0.000 claims abstract description 22
- 238000000576 coating method Methods 0.000 claims abstract description 16
- 150000001298 alcohols Chemical class 0.000 claims abstract description 10
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 74
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 51
- 239000000839 emulsion Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000012295 chemical reaction liquid Substances 0.000 claims description 14
- 239000011248 coating agent Substances 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims description 7
- 239000003973 paint Substances 0.000 claims description 7
- 229940045872 sodium percarbonate Drugs 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 abstract description 37
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 6
- 238000005886 esterification reaction Methods 0.000 abstract description 4
- 238000001035 drying Methods 0.000 abstract description 3
- IFPMZBBHBZQTOV-UHFFFAOYSA-N 1,3,5-trinitro-2-(2,4,6-trinitrophenyl)-4-[2,4,6-trinitro-3-(2,4,6-trinitrophenyl)phenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C=2C(=C(C=3C(=CC(=CC=3[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)C(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O IFPMZBBHBZQTOV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000007864 aqueous solution Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 235000019645 odor Nutrition 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000012752 auxiliary agent Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229960000541 cetyl alcohol Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 2
- KESQFSZFUCZCEI-UHFFFAOYSA-N 2-(5-nitropyridin-2-yl)oxyethanol Chemical compound OCCOC1=CC=C([N+]([O-])=O)C=N1 KESQFSZFUCZCEI-UHFFFAOYSA-N 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/44—Preparation of carboxylic acid esters by oxidation-reduction of aldehydes, e.g. Tishchenko reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of preparation of odorless coatings, and particularly relates to a preparation process of an odorless film-forming aid. The invention utilizes alcohols to react with residual isobutyric acid in the preparation of dodecyl or hexadecyl alcohol ester to generate isobutyrate, thereby eliminating the odor in the film forming additive; the resulting isobutyrate ester can be used as an active ingredient of a film-forming aid. The addition amount of the alcohol substance is larger than the generation amount of isobutyric acid in the preparation process of the dodeca-or hexadecanol ester, so that the esterification reaction of the isobutyric acid and the alcohol substance is promoted, the hydrolysis of the dodeca/hexadecanol ester is inhibited, and the redundant alcohol can be used as a quick-drying component and an antifreezing component of the film-forming additive without influencing the performance of the film-forming additive.
Description
Technical Field
The invention belongs to the technical field of preparation of odorless coatings, and particularly relates to a preparation process of an odorless film-forming aid.
Background
When the environment temperature is lower than the film-forming temperature of the emulsion, the emulsion is not easy to form a film, and the film-forming auxiliary agent can reduce the minimum film-forming temperature of the emulsion, help film formation and does not influence the characteristic of damaging a film. At present, the film forming auxiliary agents mainly used for water-based paint on the market comprise two products, namely dodecyl alcohol ester and hexadecyl alcohol ester, and the two products can effectively reduce the film forming temperature of the emulsion.
Wherein the synthesis of the cetyl alcohol ester generally comprises the steps of: 1) under the action of a basic catalyst, partial aldol condensation reaction and disproportionation reaction of isobutyraldehyde are carried out to obtain 2, 2, 4-trimethyl-1, 3-pentanediol monoisobutyrate and reaction liquid of unreacted isobutyraldehyde; 2) removing the basic catalyst in the reaction liquid, then carrying out oxidation reaction under the action of an oxidant and an oxidation catalyst, and oxidizing unreacted isobutyraldehyde into isobutyric acid; 3) after removing the oxidation catalyst in the reaction solution, 2, 2, 4-trimethyl-1, 3-pentanediol monoisobutyrate and isobutyric acid are subjected to esterification reaction under the catalysis of an esterification catalyst to finally obtain 2, 2, 4-trimethyl-1, 3-pentanediol diisobutyrate.
The synthesis process has unreacted isobutyric acid, and the synthesized product 2, 2, 4-trimethyl-1, 3-pentanediol diisobutyrate is hydrolyzed to generate isobutyric acid. Isobutyric acid has a bad smell of feet, and a very small amount can stimulate the smell. The main method for improving the odor problem of cetyl alcohol ester in the prior art is to cover the odor problem by adding essence, but the odor problem cannot be completely solved, and even in the process of adding the essence, the essence components and the coating components interact to cause the denaturation of the essence components and generate other odors.
Disclosure of Invention
In order to solve the problem that the film-forming assistant in the prior art has peculiar smell, the invention aims to provide a preparation process of the odor-free film-forming assistant, wherein the twelve or hexadecanol ester product produced by the process has the total content of more than 98 percent, meets the content quality standard of the film-forming assistant and can effectively solve the problem of peculiar smell of the product.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
a preparation process of an odorless film forming aid specifically comprises the following steps:
1) synthesizing dodecyl alcohol ester by taking isobutyraldehyde as a raw material under an alkaline condition, and reacting at the temperature of 160-200 ℃ for 8-15 min; the mass ratio of isobutyraldehyde to alkali is 50-180: 1;
2) removing isobutyraldehyde which does not participate in the reaction in the dodecanol ester reaction solution, and then adding alcohols, wherein the mass ratio of the addition amount of the alcohols to the dodecanol ester is (0.1-1): 99-99.9, and reacting for 1-2 h; the alcohol is any one of ethylene glycol, ethanol or propanol.
Preferably, the mass ratio of isobutyraldehyde to base in the step 1) is 50-53: 1.
a preparation process of an odorless film forming aid specifically comprises the following steps:
1) synthesizing dodecyl alcohol ester by taking isobutyraldehyde as a raw material under an alkaline condition, and reacting at the temperature of 160-200 ℃ for 8-15 min; the mass ratio of isobutyraldehyde to alkali is 140-180: 1;
2) adding sodium percarbonate into the reaction liquid obtained in the step 1), wherein the temperature is 190-200 ℃, and the reaction time is 0.5-1 h;
the adding amount of the sodium percarbonate is 18-22% of the mass of the isobutyraldehyde in the step 1);
3) continuously reacting for 0.5-1 h at 190-200 ℃ under an acidic condition to obtain a reaction solution of the hexadecanol ester;
4) adding alcohols into the reaction liquid obtained in the step 3), wherein the mass ratio of the addition amount of the alcohols to the reaction liquid is (0.1-1): 99-99.9, and reacting for 1-2 h; the alcohol is any one of ethylene glycol, ethanol or propanol.
Based on a general inventive concept, the invention also comprises the odorless film-forming aid prepared by the preparation process.
Based on one general inventive concept, the present invention also includes the use of the above described odor-free coalescent as an auxiliary component of a coating.
Preferably, the coating is a water-based coating.
More preferably, the aqueous coating is a mixture of any one or two or more of an acrylate emulsion, a styrene emulsion, a vinyl acetate emulsion, a polyurethane emulsion, an epoxy emulsion, a styrene/butadiene emulsion, and an acrylonitrile/butadiene/styrene emulsion in any proportion.
Preferably, the addition amount of the odorless film-forming aid in the coating is 3% -7%.
The technical principle of the invention is that alcohols are used for reacting with residual isobutyric acid in the preparation of dodecyl alcohol ester or hexadecyl alcohol ester to generate isobutyrate, thereby eliminating the odor in the film-forming auxiliary agent; the resulting isobutyrate ester can be used as an active ingredient of a film-forming aid. The addition amount of the alcohol substance is larger than the generation amount of isobutyric acid in the preparation process of the dodeca-or hexadecanol ester, so that the esterification reaction of the isobutyric acid and the alcohol substance is promoted, the hydrolysis of the dodeca/hexadecanol ester is inhibited, and the redundant alcohol can be used as a quick-drying component and an antifreezing component of the film-forming additive without influencing the performance of the film-forming additive. After verification, after the film-forming additive is added into the water-based paint, the paint has no peculiar smell or the degree of the peculiar smell is obviously improved, and particularly, when the addition amount of glycol or ethanol in the film-forming additive is 0.7-1%, the peculiar smell of isobutyric acid is completely eliminated, so that the odor-free paint standard can be reached.
Compared with the prior art, the invention has the beneficial effects that:
1) according to the invention, excessive alcohol substances are added in the preparation of the twelve or sixteen carbon alcohol ester, so that residual isobutyric acid in the reaction liquid is reacted, thereby eliminating odor sources, and the generated isobutyrate can be used as an effective component of a film-forming additive, so that the performance of the film-forming additive is improved; the film-forming additive does not need to add essence or spice additionally during use, avoids the product quality problem caused by the denaturation of essence components, and can reduce the production cost;
2) by optimizing the proportion, the added redundant alcohol substances are soft in taste and can be used as quick-drying components and anti-freezing components in the film-forming auxiliary agent, and the overall performance of the film-forming auxiliary agent is not influenced.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments;
the reagents used in the present invention are either commonly available or available to one skilled in the art through published routes.
Example 1
A preparation process of an odorless film-forming aid specifically comprises the following steps:
1) adding 10kg of isobutyraldehyde into 0.2kg of sodium hydroxide aqueous solution, reacting for 10min at 180 ℃; the mass concentration of the sodium hydroxide aqueous solution is 35 percent;
2) adding 1.9kg of sodium percarbonate, stirring and reacting at the reaction temperature of 200 ℃ for 45 min;
3) both the step 1) and the step 2) can generate partial isobutyric acid, so that the reaction liquid is acidic, and the reaction is continued for 1h at the temperature of 200 ℃ to obtain the hexadecanol ester;
4) adding 9.50mL of glycol, and continuing to react for 1h to obtain the compound.
The yield of the final hexadecanol ester is about 95.02 percent based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of the ethylene glycol to the hexadecanol ester is 0.1%: 99.9 percent.
Example 2
A preparation process of an odorless film-forming aid specifically comprises the following steps:
1) adding 10kg of isobutyraldehyde into 0.15kg of sodium hydroxide aqueous solution, reacting for 10min at 180 ℃; the mass concentration of the sodium hydroxide aqueous solution is 38 percent;
2) adding 1.85kg of sodium percarbonate, stirring and reacting at the reaction temperature of 200 ℃ for 40 min;
3) both the step 1) and the step 2) can generate partial isobutyric acid, so that the reaction liquid is acidic, and the reaction is continued for 1h at the temperature of 200 ℃ to obtain the hexadecanol ester;
4) adding 27.57mL of ethanol, and continuing to react for 1.5h to obtain the compound.
The yield of the final hexadecanol ester is about 91.89% based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of the ethanol to the hexadecanol ester is 0.3%: 99.7 percent.
Example 3
A preparation process of an odorless film-forming aid specifically comprises the following steps:
1) adding 9kg of isobutyraldehyde into 0.15kg of sodium hydroxide aqueous solution, reacting for 12min at the temperature of 170 ℃; the mass concentration of the sodium hydroxide aqueous solution is 36 percent;
2) adding 1.9kg of sodium percarbonate, stirring and reacting at the reaction temperature of 200 ℃ for 40 min;
3) both the step 1) and the step 2) can generate partial isobutyric acid, so that the reaction liquid is acidic, and the reaction is continued for 1h at the temperature of 200 ℃ to obtain the hexadecanol ester;
4) adding 40.59mL of glycol, and continuing to react for 1h to obtain the compound.
The yield of the final hexadecanol ester is about 90.21% based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of the ethylene glycol to the hexadecanol ester is 0.5%: 99.5 percent.
Example 4
A process for the preparation of an odorless film forming aid, the process comprising the specific steps of referring to example 1;
the difference from the embodiment 1 is that 66.46mL of ethylene glycol is added in the step 4), and the reaction is continued for 1h to obtain the compound;
the yield of the final hexadecanol ester is about 94.95 percent based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of the ethylene glycol to the hexadecanol ester is 0.7%: 99.3 percent.
Example 5
A process for the preparation of an odorless film forming aid, the process comprising the specific steps of referring to example 2;
the difference from the embodiment 2 is that 92mL of ethanol is added in the step 4), and the reaction is continued for 1.5h to obtain the compound;
the yield of the final hexadecanol ester is about 92 percent based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of ethanol to the hexadecanol ester is 1%: 99 percent.
Example 6
A preparation process of an odorless film-forming aid specifically comprises the following steps:
1) slowly adding 3.6kg of isobutyraldehyde into 0.2kg of sodium hydroxide aqueous solution, reacting for 10min at the temperature of 180 ℃; the mass concentration of the sodium hydroxide aqueous solution is 35 percent;
2) filtering unreacted isobutyraldehyde to obtain a reaction solution with the main component of dodecyl alcohol ester; adding 2.34mL of glycol, and continuing to react for 2h to obtain the compound.
The yield of the final dodecyl alcohol ester is about 64.92 percent based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of the ethylene glycol to the lauryl alcohol ester is 0.1%: 99.9 percent.
Example 7
A preparation process of an odorless film-forming aid specifically comprises the following steps:
1) slowly adding 3kg of isobutyraldehyde into 0.15kg of sodium hydroxide aqueous solution, reacting at 180 ℃ for 10 min; the mass concentration of the sodium hydroxide aqueous solution is 38 percent;
2) filtering unreacted isobutyraldehyde after the reaction is completed to obtain reaction liquid of which the main component is dodecyl alcohol ester; adding 5.72mL of ethanol, and continuing to react for 2h to obtain the compound.
The yield of the final dodecyl alcohol ester is about 63.52 percent based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of ethanol to the dodecanol ester is 0.3%: 99.7 percent.
Example 8
A preparation process of an odorless film-forming aid specifically comprises the following steps:
1) slowly adding 3.6kg of isobutyraldehyde into 0.2kg of sodium hydroxide aqueous solution, reacting for 10min at the temperature of 180 ℃; the mass concentration of the sodium hydroxide aqueous solution is 36 percent;
2) after the reaction is completed, filtering unreacted isobutyraldehyde to obtain reaction liquid with the main component of alcohol ester twelve; adding 12.2mL of glycol, and continuing to react for 2h to obtain the product.
The yield of the final dodecyl alcohol ester is about 68.01% based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of the ethylene glycol to the lauryl alcohol ester is 0.5%: 99.5 percent.
Example 9
A process for the preparation of an odorless film forming aid, the process comprising the steps of referring to example 6;
the difference from the example 6 is that 16.16mL of ethylene glycol is added in the step 3), and the reaction is continued for 2h to obtain the compound.
The yield of the final dodecyl alcohol ester is about 64.15% based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of the ethylene glycol to the lauryl alcohol ester is 0.7%: 99.3 percent.
Example 10
A process for the preparation of an odorless coalescent, the process comprising the steps of referring to example 7;
the difference from the embodiment 7 is that 18.91mL of ethanol is added in the step 3), and the reaction is continued for 2h to obtain the compound;
the yield of the final dodecyl alcohol ester is about 63.05 percent based on the amount of isobutyraldehyde in the process; the mass concentration ratio of the addition amount of ethanol to the mass concentration of the dodecyl alcohol ester is 1%: 99 percent.
In examples 1 to 10, the yield of the dodecanol ester or hexadecanol ester and the amount ratio of the dodecanol ester or hexadecanol ester to the alcohol (ethylene glycol or ethanol) are shown in table 1;
TABLE 1 dosage ratio of film forming assistant to alcohol in examples 1 to 10
In order to show the technical effect of the invention, the film-forming assistant obtained in the embodiment 1-10 is added into the coating for effect verification, and the specific process is as follows.
Test examples
The film-forming assistant obtained in examples 1 to 10 was added to an aqueous coating material (a commercially available acrylic emulsion) in an amount of 5%; after uniform dispersion, coating a film; after standing for 48 hours, performance evaluation was performed. In the test, isobutyraldehyde is used as a raw material, a film-forming aid without adding alcohol in the preparation process is used as a control group (cetyl alcohol ester obtained in the preparation process is used as a control group 1, and lauryl alcohol ester is used as a control group 2), and a treatment group without adding the film-forming aid is used as a blank; three replicates were set for each condition and the test results averaged.
The film forming effect is measured by using a minimum film forming temperature instrument according to GB/T9267-2008 'determination of white point temperature and minimum film forming temperature of emulsion and paint for paint and polymer dispersoid for plastics', the temperature is 20 ℃, and the relative humidity is 50%; the odor was determined by olfaction with reference to GB/T15549-. The film forming effect under different conditions is compared and shown in the table 2;
TABLE 2 comparison of film-Forming Effect of acrylic emulsions under different conditions
As can be seen from the above table, the film-forming additive obtained in examples 1 to 10 has good compatibility with acrylic emulsion; after the film is kept stand for 24h, the appearance is good, the film is formed, and the powder is not dropped off after dry wiping. It is demonstrated that the film-forming aids obtained in examples 1 to 10 do not affect the performance of the acrylic emulsion. However, from the aspect of odor, after the film-forming additive obtained in the embodiments 1 to 10 is added, the acrylic emulsion has no peculiar smell or the degree of peculiar smell is obviously improved, and particularly, when the addition amount of the glycol or the ethanol reaches 0.7 to 1 percent, the peculiar smell of the isobutyric acid is completely eliminated or covered, so that the odor-free coating standard can be reached.
Claims (8)
1. A preparation process of an odorless film-forming aid is characterized by comprising the following steps:
1) synthesizing dodecyl alcohol ester by taking isobutyraldehyde as a raw material under an alkaline condition, and reacting at the temperature of 160-200 ℃ for 8-15 min; the mass ratio of isobutyraldehyde to alkali is 50-180: 1;
2) removing isobutyraldehyde which does not participate in the reaction in the dodecanol ester reaction solution, and then adding alcohols, wherein the mass ratio of the addition amount of the alcohols to the dodecanol ester is (0.1-1): 99-99.9, and reacting for 1-2 h; the alcohol is any one of ethylene glycol, ethanol or propanol.
2. The process of claim 1, wherein: step 1), the mass ratio of isobutyraldehyde to alkali is 50-53: 1.
3. a preparation process of an odorless film-forming aid is characterized by comprising the following steps:
1) synthesizing dodecyl alcohol ester by taking isobutyraldehyde as a raw material under an alkaline condition, and reacting at the temperature of 160-200 ℃ for 8-15 min; the mass ratio of isobutyraldehyde to alkali is 140-180: 1;
2) adding sodium percarbonate into the reaction liquid obtained in the step 1), wherein the temperature is 190-200 ℃, and the reaction time is 0.5-1 h; the adding amount of the sodium percarbonate is 18-22% of the mass of the isobutyraldehyde in the step 1);
3) continuously reacting for 0.5-1 h at 190-200 ℃ under an acidic condition to obtain a reaction solution of the hexadecanol ester;
4) adding alcohols into the reaction liquid obtained in the step 3), wherein the mass ratio of the addition amount of the alcohols to the reaction liquid is (0.1-1): 99-99.9, and reacting for 1-2 h; the alcohol is any one of ethylene glycol, ethanol or propanol.
4. An odorless film-forming additive prepared by the preparation process as claimed in any one of claims 1 to 3.
5. Use of the odor-free coalescent of claim 4 as an auxiliary component of a coating.
6. The use of claim 5, wherein: the coating is a water-based coating.
7. The use of claim 6, wherein: the water paint is any one or mixture of more than two of acrylate emulsion, styrene emulsion, vinyl acetate emulsion, polyurethane emulsion, epoxy emulsion, styrene/butadiene emulsion and acrylonitrile/butadiene/styrene emulsion in any proportion.
8. Use according to any one of claims 5 to 7, wherein: the addition amount of the odorless film-forming aid in the coating is 3% -7%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114262469A (en) * | 2021-12-24 | 2022-04-01 | 华昌智典新材料(江苏)有限公司 | Preparation process for preparing film forming additive by using alcohol ester hexadecane |
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| EP2436667A1 (en) * | 2010-09-08 | 2012-04-04 | Politechnika Opolska | A method to manufacture a mixture of aliphatic hydroxyesters, especially from isobutyric aldehyde |
| US20150166450A1 (en) * | 2013-12-13 | 2015-06-18 | Eastman Chemical Company | Reduction of ester formation in isobutyraldehyde oxidation |
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| WO1983002940A1 (en) * | 1982-02-18 | 1983-09-01 | Grote, Dace | Formation of isobutyric acid or mehtyl isobutyrate |
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| CN114262469A (en) * | 2021-12-24 | 2022-04-01 | 华昌智典新材料(江苏)有限公司 | Preparation process for preparing film forming additive by using alcohol ester hexadecane |
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