CN105885028B - Polyether alcohol ester compound and application thereof - Google Patents
Polyether alcohol ester compound and application thereof Download PDFInfo
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- CN105885028B CN105885028B CN201610430720.0A CN201610430720A CN105885028B CN 105885028 B CN105885028 B CN 105885028B CN 201610430720 A CN201610430720 A CN 201610430720A CN 105885028 B CN105885028 B CN 105885028B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/50—Sebacic acid esters
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
- C09D5/024—Emulsion paints including aerosols characterised by the additives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- 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
-
- 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
- C09D7/65—Additives macromolecular
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
- C08G2650/04—End-capping
Abstract
The invention relates to a polyether alcohol ester compound and application thereof. The polyether alcohol ester compound is obtained by esterification reaction of polyether alcohol and aliphatic organic acid. The film forming test of the water-based paint shows that: the polyether alcohol ester compound provided by the invention is an efficient film-forming auxiliary agent which has a high boiling point and is friendly to human bodies and environment. Therefore, the polyether alcohol ester compound provided by the invention can be used as a film forming aid of a water-based paint.
Description
Technical Field
The invention relates to a polyether alcohol ester compound and application thereof, in particular to application of the polyether alcohol ester compound synthesized by polyether alcohol and aliphatic organic acid as a film forming aid of a water-based paint.
Background
Latex paints are a broad class of waterborne coatings that contain very low levels of Volatile Organic Compounds (VOC), and are "green paints". Latex paints are primarily a mixture of aqueous dispersions of polymer particles and aqueous dispersions of pigment particles. However, they have no good workability, so that it is difficult to obtain good paint films, and various additives must be added to achieve the required workability and film-forming quality, and the film-forming additive is one of the most important additives in the latex paint.
The film forming process after the emulsion paint is coated mainly comprises three stages, wherein the emulsion paint is in a wet state and then slowly dries after being coated on a wall, namely the first process of film forming, the evaporation of moisture is critical in the stage, emulsion particles, pigments and fillers and other components become the main components of the paint film along with the evaporation of the moisture, and then the emulsion paint enters the second process of film forming of the paint, namely the key process of film forming, at the moment, as the moisture is continuously evaporated, protective layers on the surfaces of the emulsion particles are gradually peeled off, and exposed emulsion particles are close to each other to be in contact with each other, so that the degree of tight accumulation is achieved. At the same time, water-soluble substances in the composition will still be present in the moisture between the particles. After this stage, the evaporation rate of the moisture is greatly reduced compared to the first process. Finally, with the mutual fusion of the exposed particles, the emulsion particles are gradually deformed, condensed and fused to finally form a continuous coating film.
Film-forming aids are high boiling solvents added to latex paints to aid in film formation, which can allow higher Tg (glass transition temperature) polymers to form films at lower temperatures. The film-forming aid is adsorbed on the polymer particles, the particles are more easily deformed due to dissolution, and the Tg of the film-forming aid is low, so that more free volume can be provided, and a better film-forming effect can be achieved.
Given the increasing restrictions imposed by legislation and standards on VOCs, film-forming aids will move toward high boiling points, multiple functionalities, low odor, multi-component differentiation, and low toxicity, safety, acceptable biodegradability.
Disclosure of Invention
The inventor designs and prepares a polyether alcohol ester compound. The polyether alcohol ester compound is obtained by esterification reaction of polyether alcohol and aliphatic organic acid (such as aliphatic carboxylic acid or aliphatic sulfonic acid). The film forming test of the water-based paint shows that: the polyether alcohol ester compound provided by the invention is an efficient film-forming auxiliary agent which has a high boiling point and is friendly to human bodies and environment.
The invention aims to provide a polyether alcohol ester compound.
The polyether alcohol ester compound is a compound shown as a formula A:
in the formula A, R1And R2Each independently selected from: hydrogen (H) or C1～C10One of a linear or branched alkyl group; r3Is H or
R4And R5Each independently selected from:
one of the above two methods; or the like, or, alternatively,
R3,R4and R5Any two of them are combined into
m is 2 to 50, n is 2 to 50;
wherein R is6Is H or C1～C10Straight or branched alkyl, R7Is composed of
p is 2 to 50, R8And R9Each independently selected from: c3～C18One of a straight chain or branched alkyl chain, q is an integer of 1-8, and the mark position of the curve is a substitution position (the same below).
Another object of the present invention is to disclose a use of the compound of formula A as described above, i.e., an application of the compound of formula A as a film-forming aid for aqueous coating materials (e.g., latex paints).
In addition, the invention also provides a method for preparing the compound shown in the formula A, which mainly comprises the following steps: carrying out esterification reaction on polyether alcohol (a compound shown in a formula B) and corresponding monobasic or dibasic aliphatic organic carboxyl to obtain a target object (a compound shown in a formula A);
in the formula B, R1～R3M and n are as defined above.
Detailed Description
In a preferred embodiment of the present invention, R1And R2Each independently selected from: hydrogen (H) or C1～C5One of a linear or branched alkyl group; r3Is H;
R4and R5Are all made of
Or the like, or, alternatively,
R4and R5Combination (R)4+R5) Is composed of
m is 2 to 50, n is 2 to 50;
wherein R is8Is C7～C11A straight chain or branched chain alkyl group, and q is an integer of 1-8.
In another preferred embodiment of the present invention, R1And R2Each independently selected from: c1～C5One of a linear or branched alkyl group; r3Is composed of
R4And R5Are all made of
m is 2 to 50, n is 2 to 50;
wherein R is6Is C1～C5Straight or branched alkyl, R7Is composed of
p is 2 to 50, R8Is C7～C11Straight or branched chain alkyl.
The invention provides a method for preparing a compound shown as a formula A, which specifically comprises the following steps:
in the presence of catalyst (acid catalyst for esterification reaction such as acid cation exchange resin) and inert gas (such as nitrogen), polyether polyol (compound shown in formula B) and long carbon chain fatty organic acid are kept at 100-150 ℃ for at least 5 hours under stirring, cooled, added with proper amount of solvent for suction filtration, filtrate is transferred to a separating funnel, added with proper amount of water for extraction, kept still, taken organic phase is washed to neutrality by alkali liquor and water in sequence, and low-boiling-point substances are removed by evaporation to obtain the target compound (compound shown in formula A).
When the polyether alcohol ester compound (the compound shown in the formula A) is used as a film forming aid for water-based coatings (such as emulsion paints and the like), the addition amount of the polyether alcohol ester compound in the water-based coatings is 0.1-2.0 wt% (based on the total weight of the water-based coatings being 100%).
The polyether alcohol ester compound designed and prepared by the invention is used as a film forming auxiliary agent of the water-based paint, not only does not influence the performance of the water-based paint, but also has a higher boiling point and a lower VOC (volatile organic compound) to a certain extent compared with the existing film forming auxiliary agent.
The present invention is further illustrated by the following examples, which are intended to better understand the contents of the present invention and not to limit the scope of the present invention.
In the following examples, the specifications of the raw materials involved are as follows:
polyether polyol: fine chemical Co Ltd of Industrial grade, Shanghai Hao
Emulsion paint: industrial grade, Nippon coatings (China) Ltd
Preparation of polyether alcohol ester compounds
Example 1
Preparation of a Compound represented by the formula A-1:
10 parts of polyether polyol (a compound shown as a formula B-1 and having a molecular weight of 400), 6 parts of 2-ethyl-hexanoic acid and anhydrous sodium sulfate are placed in a four-neck flask provided with a mechanical stirring and condensing tube and a thermometer, the reaction system is slowly heated to 100-150 ℃ in the presence of p-toluenesulfonic acid (a catalyst) and nitrogen, and stirring is kept for 5 hours at the temperature of 100-150 ℃. Cooling, adding appropriate amount of dichloromethane (solvent), filtering, transferring filtrate to a separating funnel, adding appropriate amount of water for extraction, standing, separating out water phase, washing organic phase with alkali liquor and water sequentially to neutrality, evaporating to remove low boiling point substance to obtain light yellow transparent substance (compound shown in formula A-1), wherein the infrared spectrogram data is as follows:
IR (tabletting method): 2968.58(s, upsilon-C-H), 1738.79(s, upsilon-C ═ O), 1345.72(s, upsilon-C-O-C), 1247.85, 1108.23(d, upsilon-CO-O).
Example 2
Preparation of a Compound represented by the formula A-2:
10g of polyether polyol (a compound shown as a formula B-2 and having a molecular weight of 300), 6 parts of 2-ethyl-hexanoic acid and anhydrous sodium sulfate are placed in a four-neck flask provided with a mechanical stirring and condensing tube and a thermometer, the reaction system is slowly heated to 150 ℃ in the presence of p-toluenesulfonic acid (a catalyst) and nitrogen, and stirring is kept at 100-150 ℃ for 5 hours. Cooling, adding appropriate amount of dichloromethane (solvent), filtering, transferring filtrate to a separating funnel, adding appropriate amount of water for extraction, standing, separating out water phase, sequentially washing organic phase with alkali liquor and water to neutrality, evaporating to remove low-boiling-point substance to obtain light yellow transparent substance (compound shown in formula A-2), wherein the infrared spectrogram data is as follows:
IR (tabletting method): 2968.58(s, upsilon-C-H), 1738.79(s, upsilon-C ═ O), 1345.72(s, upsilon-C-O-C), 1247.85, 1108.23(d, upsilon-CO-O).
Example 3
Preparation of a Compound represented by the formula A-3:
the same procedures and conditions as in example 1 were repeated except that 10 parts of sebacic acid was used instead of 6 parts of 2-ethyl-hexanoic acid in example 1, to obtain a pale yellow transparent substance (compound represented by formula A-3) whose IR spectrum data was as follows:
IR (tabletting method): 2968.58(s, upsilon-C-H), 1738.79(s, upsilon-C ═ O), 1345.72(s, upsilon-C-O-C), 1247.85, 1108.23(d, upsilon-CO-O).
Example 4
Preparation of a Compound represented by the formula A-4:
the same procedures and conditions as in example 2 were repeated except that 10 parts of lauric acid was used instead of 6 parts of 2-ethyl-hexanoic acid in example 2, to give a pale yellow transparent substance (a compound represented by the formula A-4) whose IR spectrum data were as follows:
IR (tabletting method): 2968.58(s, upsilon-C-H), 1738.79(s, upsilon-C ═ O), 1345.72(s, upsilon-C-O-C), 1247.85, 1108.23(d, upsilon-CO-O).
film-Forming Properties of polyether alcohol esters prepared in examples 1 to 4
Example 5
(1) VOC testing
VOC generally refers to an organic compound that readily develops at ordinary temperatures. More common are benzene, toluene, xylene, ethylbenzene, styrene, formaldehyde, ketones, and the like. These compounds have the characteristics of being volatile and hydrophilic, and are widely applied to the industrial fields of indoor and outdoor, automobile decoration materials and the like. VOC has great influence on human health, can harm the liver, kidney, brain and nervous system of people, causes serious consequences such as hypomnesis and even can cause cancer. Therefore, the synthesis of high boiling point zero VOC compounds is very commercial value.
Testing procedure of VOC: selecting proper internal standard substances (such as isobutanol, ethylene glycol phenyl ether, hexadecane, DEA and the like), measuring corresponding factors of all components subjected to qualitative analysis, (measuring standard substances of all components required by the corresponding factors, if the corresponding factors are not set to be 1), weighing a certain amount of polyether alcohol ester surfactant samples, adding a proper amount of internal standard substances, diluting the internal standard substances to a proper volume by using methanol, detecting according to the conditions, and calculating the VOC content according to the content of volatile matters. The VOC was required to be <2g/L (acceptable).
The compounds of formulae A-1, A-2, A-3 and A-4 and the existing film-forming auxiliaries (as comparison) were tested for their VOC under identical conditions, the results of which are given in Table 1.
TABLE 1
The comparatives 1-4 are the existing film forming aids.
As can be seen from Table 1, none of the VOC's of the conventional film-forming aids meet the standards at 280 ℃.
(2) Film Forming Property test
The prepared polyether alcohol ester surfactant is applied to a formula of the water-based paint emulsion paint, equivalent replacement is carried out on the prepared polyether alcohol ester surfactant and the conventional film-forming auxiliaries, and the film-forming performance is compared, so that the prepared polyether alcohol ester surfactant can help to form a film; meanwhile, other properties of the latex paint are tested, such as the water resistance, alkali resistance, stain resistance and other paint full performance tests of a latex paint film.
The specific test method comprises the following steps: the polyether alcohol ester surfactant (a compound shown in formulas A-1, A-2, A-3 or A-4) and Coasol or DIB (the existing film forming auxiliary agent) prepared by the invention are respectively prepared into water-based paint emulsion paint according to the formula tables in tables 2 and 3, a coating film is prepared under a standard state, and the film forming time and the film forming state are observed.
TABLE 2 composition of zero VOC waterborne coating formulation
TABLE 3A zero VOC waterborne coating formulation two composition components
The experimental results are as follows: the film forming time of the polyether alcohol ester film forming additive prepared by the experiment is equivalent to that of the existing film forming additive, and the film forming effect is superior to that of the existing film forming additive.
(3) Full performance testing
The polyether alcohol ester surfactant (the compound shown in the formula A-1, A-2, A-3 or A-4) prepared by the invention is prepared into water-based paint emulsion paint according to the formula tables of the table 2 and the table 3 respectively, and the comprehensive performance of the water-based paint emulsion paint is examined, wherein the specific result is shown in the table 4.
TABLE 4 full Performance test
As can be seen from Table 4: the polyether alcohol ester compound provided by the invention has excellent film forming performance, high efficiency, easy preparation and low cost when being applied to a formula of a water-based paint emulsion paint, meets the requirement of industrial production, and can replace the conventional common film forming auxiliary agent. And the product of the invention has no influence on the performance of the coating.
Claims (4)
1. A polyether alcohol ester compound is a compound shown as a formula A:
in the formula A, R1And R2Each independently selected from: hydrogen or C1～C10One of a linear or branched alkyl group; r3Is H or
R4And R5Each independently selected from:
one of the above two methods; or the like, or, alternatively,
R3,R4and R5Any two of them are combined into
m is 2 to 50, n is 2 to 50;
wherein R is6Is H or C1～C10Straight or branched alkyl, R7Is composed of
p is 2 to 50, R8And R9Each independently selected from: c3～C18One of a straight chain or branched alkyl chain, and q is an integer of 1 to 8.
2. The polyether alcohol ester compound according to claim 1, wherein R is1And R2Each independently selected from: hydrogen or C1～C5One of a linear or branched alkyl group; r3Is H; r4And R5Are all made of
Or, R4And R5In combination of
Wherein R is8Is C7～C11A straight chain or branched chain alkyl group, and q is an integer of 1-8.
3. The polyether alcohol ester compound according to claim 1, wherein R is1And R2Each independently selected from: c1～C5One of linear chain or branched chain alkyl；R3Is composed of
R4And R5Are all made of
Wherein R is6Is C1～C5Straight or branched alkyl, R7Is composed of
R8Is C7～C11Straight or branched chain alkyl.
4. The application of a polyether alcohol ester compound as a film-forming assistant of a water-based paint;
wherein, the polyether alcohol ester compound is a compound shown as a formula A:
in the formula A, R1And R2Each independently selected from: hydrogen or C1～C10One of a linear or branched alkyl group; r3Is H or
R4And R5Each independently selected from:
one of the above two methods; or the like, or, alternatively,
R3，R4and R5Any two of them are combined into
m is 2 to 50, n is 2 to 50;
wherein R is6Is H or C1～C10Straight chainOr a branched alkyl radical, R7Is composed of
p is 2 to 50, R8And R9Each independently selected from: c3～C18One of a straight chain or branched alkyl chain, and q is an integer of 1 to 8.
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| CN106565486B (en) * | 2016-10-31 | 2019-04-05 | 华东理工大学 | Branch polyether alkoxide compound and application thereof |
| CN108912323B (en) * | 2018-07-25 | 2021-01-15 | 肇庆欧迪斯实业有限公司 | Bridge type polyether compound and preparation method and application thereof |
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