CN113387803A - Isocaprylic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid and preparation method thereof - Google Patents

Isocaprylic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid and preparation method thereof Download PDF

Info

Publication number
CN113387803A
CN113387803A CN202110668433.4A CN202110668433A CN113387803A CN 113387803 A CN113387803 A CN 113387803A CN 202110668433 A CN202110668433 A CN 202110668433A CN 113387803 A CN113387803 A CN 113387803A
Authority
CN
China
Prior art keywords
film
forming
substituted
alkoxy
bromide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202110668433.4A
Other languages
Chinese (zh)
Inventor
季永新
邹心如
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nanjing Forestry University
Original Assignee
Nanjing Forestry University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nanjing Forestry University filed Critical Nanjing Forestry University
Priority to CN202110668433.4A priority Critical patent/CN113387803A/en
Publication of CN113387803A publication Critical patent/CN113387803A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
    • C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Abstract

The invention relates to an isooctanoic acid-3-alkoxy-2-hydroxypropyl ester film-forming additive and a preparation method thereof, wherein the structure expression of the film-forming additive is as follows:
Figure DDA0003117865420000011
wherein, R is1Represents any one of a substituted or unsubstituted C3-C5 alkyl group, a substituted or unsubstituted C3-C5 alkenyl group, and a substituted or unsubstituted C3-C5 alkynyl group. When 4 wt% of the film-forming aid prepared by the invention is added into an emulsion with a glass transition temperature of 46 ℃, the lowest film-forming temperature is 13-15 ℃, a continuous and transparent film can be formed, and the film-forming aid shows excellent film-forming property and is superior to the traditional film-forming aid. The film forming assistant prepared by the invention has good compatibility with latex, low film forming temperature and easy realizationLatex particles are absorbed, are not easy to volatilize, are safe and environment-friendly, and have wide market application prospect.

Description

Isocaprylic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid and preparation method thereof
Technical Field
The invention belongs to an emulsion film forming technology, and particularly relates to a film forming auxiliary agent and a preparation method thereof.
Background
The film-forming assistant is a strong solvent for polymer latex particles, is used for reducing the glass transition temperature (Tg) of a polymer in an emulsion in the water-based paint, can promote the plastic flow and elastic deformation of a high molecular compound, can reduce the minimum film-forming temperature (MMFT) of the water-based paint, enables the water-based paint to form a film at a lower temperature, and improves various performances of a coating film, such as scrub resistance, color development, weather resistance and the like, so that the film-forming assistant is an indispensable key material in the water-based paint. At present, most of the film-forming aids in China are alcohol ethers such as glycol ethers, diethylene glycol ethers, propylene glycol butyl ether or propylene glycol phenyl ether, and because the alcohol ethers are limited by chemical properties, any single alcohol ether compound cannot have good compatibility with all emulsions, and if the alcohol ether compound is not properly added, the emulsion breaking of the coating in the production process can be caused, so that the production loss is caused. In addition, most of the alcohol ether film-forming aids are added with high-boiling organic compounds which have high volatility and certain toxicity, and the high-boiling organic compounds can slowly migrate to the surface and volatilize into the atmosphere over time, so that the environment can be seriously polluted, and the anti-blocking property and the scratch resistance of a coating film can be deteriorated.
Disclosure of Invention
In order to solve the technical problems, the invention provides, in a first aspect, an isooctanoic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid, wherein the structure expression of the film-forming aid is as follows:
Figure BDA0003117865400000011
wherein, R is1Represents any one of a substituted or unsubstituted C3-C5 alkyl group, a substituted or unsubstituted C3-C5 alkenyl group, and a substituted or unsubstituted C3-C5 alkynyl group.
As a preferred technical scheme, the reaction raw materials of the film-forming auxiliary agent at least comprise:
Figure BDA0003117865400000021
wherein, R is2Represents any one of a substituted or unsubstituted C3-C5 alkyl group, a substituted or unsubstituted C3-C5 alkenyl group, and a substituted or unsubstituted C3-C5 alkynyl group.
As a preferred technical scheme, the reaction raw material of the film-forming auxiliary agent
Figure BDA0003117865400000022
The molar ratio of (1) to (0.8-1.2).
As a preferable technical scheme, the reaction raw material of the film-forming assistant also comprises a catalyst and an antioxidant.
As a preferable technical scheme, the catalyst is selected from one or more of quaternary ammonium salt, quaternary pyridinium salt and quaternary ammonium salt ionic liquid.
Preferably, the quaternary ammonium salt is selected from one or more of tetramethylammonium bromide, tetrabutylammonium bromide, tetraethylammonium bromide, tetrapropylammonium bromide, benzyltriethylammonium chloride, trioctylmethylammonium chloride, tetramethylammonium bromide, tetrapropylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, triethylbenzylammonium bromide, triethylhexylammonium bromide, and triethyloctylammonium bromide.
As a preferred technical scheme, the antioxidant is selected from a mixed solution of hypophosphorous acid and triphenyl phosphite or hypophosphorous acid and phosphite, and the mass ratio of the hypophosphorous acid to triphenyl phosphite or the hypophosphorous acid to phosphite is 1:1.
The second aspect of the present invention provides a method for preparing the above-mentioned film-forming aid, comprising the steps of:
(1) will be provided with
Figure BDA0003117865400000031
The catalyst and the antioxidant react for 3-7 hours at the temperature of 90-130 ℃;
(2) and carrying out reduced pressure distillation on the product obtained in the step to obtain the film-forming aid.
The third aspect of the invention provides an application of the film-forming assistant in preparing water-based coatings such as emulsion paint, solvent-based coatings, PE elastomers, adhesives, cleaning solvents and strong-moisturizing resins.
The invention has the advantages that: the film forming additive prepared by the invention only needs to be added toThe emulsion can show excellent film forming property by adding 4 wt%, and the film forming temperature is 13-15 ℃, so that a transparent continuous film can be formed without whitening phenomenon. The film forming assistant prepared by the invention adopts
Figure BDA0003117865400000032
Figure BDA0003117865400000033
The emulsion is a reaction raw material, has good compatibility with emulsion, is easy to be absorbed by emulsion particles, has a boiling point of about 270 ℃, does not have the condition that an organic compound migrates to the surface, is not volatile, is safe and environment-friendly, and has very wide market prospect.
Drawings
FIG. 1 is a comparison of the emulsion filming performance of isooctanoic acid-3-alkoxy-2-hydroxypropyl ester film forming aid of the present invention and lauryl ester film forming aid.
Detailed Description
The technical features of the technical solutions provided by the present invention are further clearly and completely described below with reference to the specific embodiments, and the scope of protection is not limited thereto.
The words "preferred", "more preferred", and the like, in the present invention refer to embodiments of the invention that may provide certain benefits, under certain circumstances. However, other embodiments may be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.
In one embodiment, the coalescent has the structural formula:
Figure BDA0003117865400000041
wherein, R is1Represents any one of a substituted or unsubstituted C3-C5 alkyl group, a substituted or unsubstituted C3-C5 alkenyl group, and a substituted or unsubstituted C3-C5 alkynyl group.
In a preferred embodiment, R is1Indicates not to fetchThe substituted C3-C5 alkyl is selected from any one of n-butyl, isobutyl, n-propyl and isopropyl.
In a preferred embodiment, R is1The unsubstituted C3-C5 alkenyl group is selected from any one of 1-butenyl, 2-methylpropenyl, 1, 3-butadienyl and allyl.
In a preferred embodiment, R is1Alkynyl representing unsubstituted C3-C5 is selected from any one of 1-butynyl, 2-butynyl, and 1, 3-butynyl.
In a most preferred embodiment, R is1Is selected from-CH2CH2CH2CH3、-CH(CH3)2Any one of the above.
In one embodiment, the reaction feed for the coalescent should include at least:
Figure BDA0003117865400000042
wherein, R is2Represents any one of a substituted or unsubstituted C3-C5 alkyl group, a substituted or unsubstituted C3-C5 alkenyl group, and a substituted or unsubstituted C3-C5 alkynyl group.
In one embodiment, the
Figure BDA0003117865400000051
In a molar ratio of 1: 0.5 or 1:0.8 or 1:0.9 or 1:1 or 1:1.1 or 1: 1.2.
Preferably, the
Figure BDA0003117865400000052
Is 1: 0.8.
Preferably, the
Figure BDA0003117865400000053
Is 1: 0.9.
Most preferably, the
Figure BDA0003117865400000054
In a molar ratio of 1: 1.1.
In a preferred embodiment, R is2Represents any of an alkyl group having C3-C5, an alkenyl group having C3-C5, and an alkynyl group having C3-C5.
In a more preferred embodiment, the alkyl group of C3-C5 is selected from any one of n-butyl, isobutyl, n-propyl, and isopropyl.
In a more preferred embodiment, the alkenyl group of C3-C5 is selected from any one of 1-butenyl, 2-methylpropenyl, 1, 3-butadienyl, allyl.
In a more preferred embodiment, the alkynyl group of C3-C5 is selected from any one of 1-butynyl, 2-butynyl, 1, 3-butynyl.
In a most preferred embodiment, R is2Is selected from-CH2CH2CH2CH3、-CH(CH3)2Any one of the above.
In one embodiment, the reaction feed of the coalescent further comprises a catalyst.
In one embodiment, the catalyst has a mass of
Figure BDA0003117865400000061
Figure BDA0003117865400000062
0.6-1.0 wt% of the total mass.
Preferably, the catalyst has a mass of
Figure BDA0003117865400000063
Figure BDA0003117865400000064
0.8 wt% of the total mass.
In one embodiment, the catalyst is selected from one or more of quaternary ammonium salts, quaternary pyridinium salts, quaternary ammonium salt ionic liquids.
Preferably, the quaternary ammonium salt catalyst is selected from one or more of tetramethylammonium bromide, tetrabutylammonium bromide, tetraethylammonium bromide, tetrapropylammonium bromide, benzyltriethylammonium chloride, trioctylmethylammonium chloride, tetramethylammonium bromide, tetrapropylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, triethylbenzylammonium bromide, triethylhexylammonium bromide, triethyloctylammonium bromide.
More preferably, the quaternary ammonium salt catalyst is tetrabutylammonium bromide.
In one embodiment, the reaction feed of the coalescent further comprises an antioxidant.
In one embodiment, the antioxidant is selected from a mixed solution of hypophosphorous acid and triphenyl phosphite or hypophosphorous acid and phosphite in a mass ratio of 1:1.
Preferably, the antioxidant is a mixed solution of hypophosphorous acid and triphenyl phosphite.
The second aspect of the present invention provides a method for preparing the above-mentioned film-forming aid, comprising the steps of:
(1) will be provided with
Figure BDA0003117865400000071
The catalyst and the antioxidant react for 3 to 7 hours at the temperature of between 90 and 130 ℃;
(2) and carrying out reduced pressure distillation on the product prepared in the step to obtain the film-forming aid. In one embodiment, the method of making the coalescing agent comprises the steps of:
(1) will be provided with
Figure BDA0003117865400000072
The catalyst and the antioxidant react for 5 hours at 130 ℃;
(2) and carrying out reduced pressure distillation on the product obtained in the step to obtain the film-forming aid.
The invention adopts
Figure BDA0003117865400000073
Is a reactant, and the film forming additive prepared by the invention
Figure BDA0003117865400000074
The resin contains lipophilic groups with proper chain length, and is easy to associate with the colloidal resin; in addition, the polar group of the film-forming additive prepared by the invention has 7 carbons, so the boiling point can be kept at 265-300 ℃, and the film-forming additive has the characteristics of easy diffusion to the surface of a polar colloid, high volatilization speed, difficult film re-adhesion and the like. The coalescing property, weather resistance, scrub resistance, color development property, storage stability and the like of the film-forming additive prepared by the invention are obviously superior to those of a commercial lauryl ester film-forming additive.
The third aspect of the invention provides an application of the film-forming assistant in preparing water-based coatings such as emulsion paint, solvent-based coatings, PE elastomers, adhesives, cleaning solvents and strong-moisturizing resins.
In one embodiment, the use of the coalescent in a styrene-acrylic emulsion.
In one embodiment, the film-forming aid is present in an amount of 3 to 5 wt% based on the weight of the styrene-acrylic emulsion.
Preferably, the mass of the film-forming assistant is 4 wt% of the mass of the styrene-acrylic emulsion.
In one embodiment, the styrene-acrylic emulsion is available under the trademark BLJ-8600H, available from Shanghai Baoligai chemical Co.
The present invention will be specifically described below by way of examples. It should be noted that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention, and that the insubstantial modifications and adaptations of the present invention by those skilled in the art based on the above disclosure are still within the scope of the present invention.
In addition, the starting materials used are all commercially available, unless otherwise specified.
Example 1
Example 1 provides a coalescent M1Said film-forming assistant M1Is expressed as
Figure BDA0003117865400000081
(wherein, said R1Represents n-butyl); the film-forming assistant M1The reaction raw materials are
Figure BDA0003117865400000082
(A1)、
Figure BDA0003117865400000083
(B1Wherein, R is2Represents n-butyl);
the film-forming assistant M1Reaction raw material A of1、B1In a molar ratio of 1: 1; the selected catalyst is quaternary ammonium salt catalyst with the mass of A1、B10.8 wt% of the total mass; the selected antioxidant is mixed solution of hypophosphorous acid and triphenyl phosphite, and the mass is A1、B10.01 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
(1) a is to be1、B1Reacting with a catalyst for 5 hours at 130 ℃;
(2) then carrying out reduced pressure distillation on the product obtained in the step to obtain the film-forming additive M1。
Example 2
Example 2 provides a coalescent M2Said film-forming assistant M2The structural expression of (A) is as follows:
Figure BDA0003117865400000091
(wherein, said R1Represents an isopropyl group); the film-forming assistant M2The reaction raw materials are
Figure BDA0003117865400000092
(A2)、
Figure BDA0003117865400000093
(B2Wherein, said R2Represents an isopropyl group);
the film-forming assistant M2Reaction raw material A of2、B2In a molar ratio of 1: 1; the selected catalyst is quaternary ammonium salt catalyst with the mass of A2、B20.8 wt% of the total mass; the selected antioxidant is mixed solution of hypophosphorous acid and triphenyl phosphite, and the mass is A2、B20.01 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
1) a is to be2、B2Reacting with a catalyst for 5 hours at 130 ℃;
2) then carrying out reduced pressure distillation on the product obtained in the step to obtain the film-forming additive M2。
Example 3
Example 3 provides a coalescent M3Said film-forming assistant M3The structural expression of (A) is as follows:
Figure BDA0003117865400000101
(wherein, said R1Represents n-butyl); the film-forming assistant M3The reaction raw materials are
Figure BDA0003117865400000102
(A3)、
Figure BDA0003117865400000103
(B3Wherein, said R2Represents n-butyl);
the film-forming assistant M3Reaction raw material A of3、B3In a molar ratio of 1: 0.9; the selected catalyst is quaternary ammonium salt catalyst with the mass of A3、B30.8 wt% of the total mass; the selected antioxidant is mixed solution of hypophosphorous acid and triphenyl phosphite, and the mass is A3、B30.01 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
1) a is to be3、B3And catalystReacting the reagent at 130 ℃ for 5 h;
2) then carrying out reduced pressure distillation on the product obtained in the step to obtain the film-forming additive M3。
Example 4
Example 4 provides a coalescent M4Said film-forming assistant M4The structural expression of (A) is as follows:
Figure BDA0003117865400000104
(wherein, said R1Represents n-butyl); the film-forming assistant M4The reaction raw materials are
Figure BDA0003117865400000105
(A4)、
Figure BDA0003117865400000111
(B4Wherein, said R2Represents n-butyl);
the film-forming assistant M4Reaction raw material A of4、B4In a molar ratio of 1: 1.1; the selected catalyst is quaternary ammonium salt catalyst with the mass of A4、B40.8 wt% of the total mass; the selected antioxidant is mixed solution of hypophosphorous acid and triphenyl phosphite, and the mass is A4、B40.01 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
1) a is to be4、B4Reacting with a catalyst for 5 hours at 130 ℃;
2) then carrying out reduced pressure distillation on the product obtained in the step to obtain the film-forming additive M4。
Example 5
Example 5 provides a coalescent M5Said film-forming assistant M5The structural expression of (A) is as follows:
Figure BDA0003117865400000112
(wherein, said R1Represents n-butyl); the film-forming assistant M5The reaction raw materials are
Figure BDA0003117865400000113
(A5)、
Figure BDA0003117865400000114
(B5Wherein, said R2Represents n-butyl);
the film-forming assistant M5Reaction raw material A of5、B5In a molar ratio of 1: 1; the selected catalyst is pyridine quaternary ammonium salt with the mass of A5、B50.8 wt% of the total mass; the selected antioxidant is mixed solution of hypophosphorous acid and triphenyl phosphite, and the mass is A5、B50.01 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
1) a is to be5、B5Reacting with a catalyst for 5 hours at 130 ℃;
2) then carrying out reduced pressure distillation on the product obtained in the step to obtain the film-forming additive M5。
Example 6
Example 6 provides a coalescent M6Said film-forming assistant M6The structural expression of (A) is as follows:
Figure BDA0003117865400000121
(wherein, said R1Represents n-butyl); the film-forming assistant M6The reaction raw materials are
Figure BDA0003117865400000122
(A6)、
Figure BDA0003117865400000123
(B6Wherein, said R2Represents n-butyl);
the film-forming assistant M6Reaction raw material A of6、B6In a molar ratio of 1: 1; the selected catalyst is quaternary ammonium salt ionic liquid with the mass of A6、B60.8 wt% of the total mass; the selected antioxidant isA mixed solution of hypophosphorous acid and triphenyl phosphite with the mass of A6、B60.01 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
1) a is to be6、B6Reacting with a catalyst for 5 hours at 130 ℃;
2) then carrying out reduced pressure distillation on the product obtained in the step to obtain the film-forming additive M6。
Performance testing
1. Film forming temperature: respectively mixing the film-forming aid described in examples 1-6 and the emulsion BLJ-8600H according to a mass ratio of 4:100, and testing the film forming temperature by using a film forming tester according to GB/T9267, wherein the film forming temperature is less than 15 ℃ and is marked as A, the temperature is 15-20 ℃ and is marked as B, the temperature is more than 20 ℃ and is marked as C, and the test results are shown in Table 1.
2. Boiling point: the boiling points of the coalescents described in examples 1-6 were determined using boiling point detectors as described in examples 1-6, wherein the boiling point was designated A when the temperature was below 265 ℃, B when the boiling point was 265-270 ℃ and C when the temperature was above 270 ℃, and the results are shown in Table 1.
3. Compatibility: the film-forming aid described in examples 1 to 6 and the emulsion BLJ-8600H were mixed in a mass ratio of 4:100, and whether the film-forming aid and the emulsion polymer were compatible was judged by DSC analysis, wherein the film-forming aid with good compatibility was denoted as A, the film-forming aid with good compatibility was denoted as B, and the film-forming aid with poor compatibility was denoted as C, and the test results are shown in Table 1.
Table 1 results of performance testing
Film formation temperature Boiling point Compatibility
Example 1 A B A
Example 2 A B A
Example 3 C A A
Example 4 B C A
Example 5 A A A
Example 6 B A B
4. Film forming property: aiming at the comparison of the film forming performance of the novel film forming additive and the existing film forming additive (dodecanol ester), the film forming additive, the dodecanol ester film forming additive and the emulsion BLJ-8600H in the mass ratio of 4:100, and the minimum film forming temperature was measured, and the test results are shown in fig. 1.
When 4 wt% of the film forming aid described in example 1 was added, the minimum film forming temperature was 13 ℃; when 4 wt% of dodecanol ester coalescing agent is added, the minimum film forming temperature is 18 ℃. The comparison shows that the isooctanoic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid disclosed by the invention has lower film-forming temperature and better film-forming effect compared with dodecanol ester under the condition of the same addition amount.
The foregoing examples are merely illustrative and serve to explain some of the features of the method of the present invention. The appended claims are intended to claim as broad a scope as is contemplated, and the examples presented herein are merely illustrative of selected implementations in accordance with all possible combinations of examples. Accordingly, it is applicants' intention that the appended claims are not to be limited by the choice of examples illustrating features of the invention. Also, where numerical ranges are used in the claims, subranges therein are included, and variations in these ranges are also to be construed as possible being covered by the appended claims.

Claims (8)

1. A3-alkoxy-2-hydroxypropyl isooctanoate film-forming aid is characterized in that the structure expression of the film-forming aid is as follows:
Figure FDA0003117865390000011
wherein, R is1Represents any one of a substituted or unsubstituted C3-C5 alkyl group, a substituted or unsubstituted C3-C5 alkenyl group, and a substituted or unsubstituted C3-C5 alkynyl group.
2. 3-alkoxy-2-hydroxypropyl isooctanoate film-forming additive according to claim 1, wherein the film-forming additive comprises at least:
Figure FDA0003117865390000012
wherein, R is2Represents a substituted or unsubstituted C3-C5 alkyl group, substituted or unsubstitutedAny of substituted C3-C5 alkenyl, substituted or unsubstituted C3-C5 alkynyl.
3. 3-alkoxy-2-hydroxypropyl isooctanoate film-forming additive according to claim 2, wherein the film-forming additive is a reaction raw material
Figure FDA0003117865390000013
The molar ratio of (1) to (0.8-1.2).
4. 3-alkoxy-2-hydroxypropyl isooctanoate film-forming aid according to claim 2 wherein the reaction raw materials further comprise a catalyst and an antioxidant.
5. 3-alkoxy-2-hydroxypropyl isooctanoate film-forming aid according to claim 4 wherein the catalyst is selected from the group consisting of quaternary ammonium salts, quaternary pyridinium salts, and quaternary ammonium salt ionic liquids.
6. The isooctanoic acid-3-alkoxy-2-hydroxypropyl ester coalescent of claim 5, wherein the quaternary ammonium salt catalyst is one or more of tetramethylammonium bromide, tetrabutylammonium bromide, tetraethylammonium bromide, tetrapropylammonium bromide, benzyltriethylammonium chloride, trioctylmethylammonium chloride, tetramethylammonium bromide, tetrapropylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, triethylbenzylammonium bromide, triethylhexylammonium bromide, triethyloctylammonium bromide.
7. The isooctanoic acid-3-alkoxy-2-hydroxypropyl ester coalescing agent of claim 4, wherein the antioxidant is selected from a mixed solution of hypophosphorous acid and triphenyl phosphite or a mixed solution of hypophosphorous acid and phosphite, and the mass ratio of hypophosphorous acid to triphenyl phosphite or a mixed solution of hypophosphorous acid and phosphite is 1:1.
8. A process for the preparation of 3-alkoxy-2-hydroxypropyl isooctanoate coalescent according to any one of claims 4-6 comprising the steps of:
(1) will be provided with
Figure FDA0003117865390000021
The catalyst and the antioxidant react for 3-7 hours at the temperature of 90-130 ℃;
(2) and carrying out reduced pressure distillation on the product obtained in the step to obtain the film-forming aid.
CN202110668433.4A 2021-06-16 2021-06-16 Isocaprylic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid and preparation method thereof Pending CN113387803A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202110668433.4A CN113387803A (en) 2021-06-16 2021-06-16 Isocaprylic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202110668433.4A CN113387803A (en) 2021-06-16 2021-06-16 Isocaprylic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid and preparation method thereof

Publications (1)

Publication Number Publication Date
CN113387803A true CN113387803A (en) 2021-09-14

Family

ID=77621454

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202110668433.4A Pending CN113387803A (en) 2021-06-16 2021-06-16 Isocaprylic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid and preparation method thereof

Country Status (1)

Country Link
CN (1) CN113387803A (en)

Similar Documents

Publication Publication Date Title
CN105504287A (en) Preparation methods and application of silane oligomer composition
CN1344300A (en) Paint compsns.
CN113354756B (en) Bio-based halogen-free flame retardant, preparation thereof and halogen-free flame-retardant water-based acrylic coating
CN111825627A (en) Preparation method of high-solid-content hydroxyl resin
CN110437711A (en) A kind of low temperature curing type B68 extinction powder epoxy resin and the preparation method and application thereof
CN113387803A (en) Isocaprylic acid-3-alkoxy-2-hydroxypropyl ester film-forming aid and preparation method thereof
WO2021124129A1 (en) Process for preparing a bonding resin
JP2697883B2 (en) Method for producing high molecular weight epoxy dimer acid ester resin
CN106317764B (en) A kind of method of modifying improving phenolic resin toughness and anti-flammability
CN112876934A (en) Novel water-based graphene polyurethane coating and preparation method thereof
CN109851758B (en) Degradable recyclable hyperbranched epoxy resin and preparation method and application thereof
WO2019034149A1 (en) Catalyst for preparing propylene glycol phenyl ether and method for synthesizing propylene glycol phenyl ether
CN112358456B (en) Preparation method of film forming aid, film forming aid and coating containing film forming aid
CN114072374B (en) Aromatic enol ethers
CN113880790A (en) Phase transfer catalytic synthesis method of 3, 4-epoxy cyclohexyl methyl-3 ',4' -epoxy cyclohexyl formic ether
CN109942795B (en) Gallic acid-based waterborne phosphorus-containing epoxy curing agent and preparation method thereof
CN112500554A (en) Latent macromolecular polythiol curing agent and preparation method and application thereof
CN112010739A (en) Film forming additive and preparation method thereof
CN115820071B (en) Corrosion-resistant coating and preparation method thereof
KR100296249B1 (en) Alpha-glycol-containing glycidyl ether resin production method
KR20010033581A (en) Low voc coating composition
CN114621468B (en) Synthesis method of chlorine-free environment-friendly toughening diluent
JP7541392B2 (en) Epoxy resin, raw material composition thereof and production method
CN112552800B (en) Single-component water-based FEVE coating resin and preparation method thereof
CN114874417B (en) Epoxy resin diluent and preparation method and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination