CN112010739A - Film forming additive and preparation method thereof - Google Patents
Film forming additive and preparation method thereof Download PDFInfo
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- CN112010739A CN112010739A CN202010797163.2A CN202010797163A CN112010739A CN 112010739 A CN112010739 A CN 112010739A CN 202010797163 A CN202010797163 A CN 202010797163A CN 112010739 A CN112010739 A CN 112010739A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000000654 additive Substances 0.000 title abstract description 9
- 230000000996 additive effect Effects 0.000 title abstract description 9
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims description 46
- -1 sodium alkoxide Chemical class 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 3
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 abstract description 24
- 238000009835 boiling Methods 0.000 abstract description 11
- 239000012752 auxiliary agent Substances 0.000 abstract description 6
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 230000002087 whitening effect Effects 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000002131 composite material Substances 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 50
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 40
- 229910015900 BF3 Inorganic materials 0.000 description 25
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000000576 coating method Methods 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000012855 volatile organic compound Substances 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960001948 caffeine Drugs 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 125000003136 n-heptyl 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])* 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- RYYVLZVUVIJVGH-UHFFFAOYSA-N trimethylxanthine Natural products CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical compound FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YGPZMMIGZREXJQ-UHFFFAOYSA-N [Na+].[Na+].CC[O-].CC[O-] Chemical compound [Na+].[Na+].CC[O-].CC[O-] YGPZMMIGZREXJQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([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])[H] 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/135—Saturated ethers containing hydroxy or O-metal groups having more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/06—Printing inks based on fatty oils
-
- 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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5022—Organic solvents containing oxygen
Abstract
The invention belongs to an emulsion film forming technology, and particularly relates to a film forming auxiliary agent and a preparation method thereof. The structural expression of the film-forming additive is as follows:
wherein, R is1、R2Each independently represents substituted or unsubstituted C1-C20Any one of substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, and substituted or unsubstituted C1-C20 alkoxy. The film forming additive prepared by the invention can realize excellent film forming property only by adding 4 wt% into the emulsion, and a transparent continuous film can be formed at the film forming temperature of about 14 ℃ without whitening phenomenon; the composite material has good compatibility, the boiling point is about 270 ℃, organic compounds cannot migrate to the surface and are not volatile, the VOC emission is low, the composite material is safe and environment-friendly, and the market prospect is wide.
Description
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
Most of the film-forming aids used at present are added with high-boiling-point organic compounds, which are non-VOC, but slowly migrate to the surface of the paint and volatilize into the atmosphere over time, so that the air is polluted, and the defects of poor blocking resistance, poor scratch resistance, easy dust adhesion and the like are brought to a coating film; there are also occasions when low-boiling film-forming auxiliaries are chosen, which inevitably volatilize to give VOCs. After the existing latex paint and other coatings prepared by the film-forming additive are used for the inner wall of a wall body, if the wall surface is exposed to the sun, the phenomenon of serious fading can occur in 5 years generally. Further, when the film-forming aid is applied and dried at a temperature not higher than the minimum film-forming temperature, a transparent continuous film is not generally formed, and a whitening phenomenon occurs, in which the minimum film-forming temperature of the acrylic emulsion resin is high, and a sufficient adhesive force cannot be obtained in a relatively cold region, and a continuous film cannot be formed.
The film-forming assistant is a strong solvent of polymer latex particles, alcohol ethers are mostly used at present, propylene glycol butyl ether, propylene glycol methyl ether acetate and ethylene glycol are commonly used, and alcohol ester twelve is commonly used in a latex paint system at present. However, due to the chemical property limitation of alcohol ether, 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 brought. The alcohol ethers have high volatility and certain toxicity, and are greatly limited in safety and environmental protection. In addition, some film-forming aids such as glycol ethers undergo hydrolysis reactions in high pH emulsion systems, which seriously affect performance.
Therefore, the development of an environment-friendly film-forming aid with good compatibility, low VOC emission and excellent film-forming property is very important.
Disclosure of Invention
To understandIn order to solve the above-mentioned technical problems, a first aspect of the present invention provides a film-forming additive, the structural expression of which is:
wherein, R is1、R2Each independently represents any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C10 carboxyl group, and a substituted or unsubstituted C1-C10 amide group.
As a preferred technical scheme, the reaction raw materials of the film-forming auxiliary agent at least comprise:
wherein, R is3、R4Each independently represents any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C1-C20 alkoxy group.
As a preferable technical means, the above
The molar ratio of (2-1): (1-2).
As a preferred technical scheme, the R is3、R4Each independently represents any one of a saturated aliphatic alkyl group having 1-10 carbon atoms, an unsaturated aliphatic alkyl group having 1-10 carbon atoms, and a cycloalkyl group having 3-10 carbon atoms.
As a preferred technical scheme, the R is3Represents a saturated fatty alkyl group having a carbon number of 1 to 6.
As a preferred technical scheme, the R is4Represents a saturated fatty alkyl group having a carbon number of 1 to 8.
As a preferable technical scheme, the reaction raw material of the film-forming assistant also comprises a catalyst I and a catalyst II.
As a preferred technical scheme, the catalyst II is selected from one or more of sodium alkoxide, hydroxide and quaternary ammonium salt.
As a preferred technical scheme, the quaternary ammonium salt is selected from one or more of tetramethyl ammonium bromide, tetraethyl ammonium bromide, tetrapropyl ammonium bromide and tetrabutyl ammonium bromide.
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
Reacting with a catalyst I at 60-200 ℃ for 1-4 h;
(2) and adding a catalyst II, and reacting at 60-200 ℃ for 3-7h 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.
Has the advantages that: the invention provides a film forming additive, which can realize excellent film forming property only by adding 4 wt% into emulsion, and can form a transparent continuous film without whitening phenomenon when the film forming temperature is about 14 ℃; the film forming assistant prepared by the invention adopts
The organic silicon dioxide is a reaction raw material, has good compatibility, has a boiling point of about 270 ℃, does not cause organic compounds to migrate to the surface, is not volatile, has low VOC emission, is safe and environment-friendly, and has wide market prospect.
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 order to solve the above technical problems, a first aspect of the present invention provides a coalescent, the coalescent having a structural formula of:
wherein, R is1、R2Each independently represents any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C10 carboxyl group, and a substituted or unsubstituted C1-C10 amide group.
In one embodiment, the coalescent has the structural formula:
wherein, R is1、R2Each independently represents any one of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C1-C20 alkoxy group.
In a preferred embodiment, R is1、R2Each independently represents any one of a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C2-C10 alkenyl group, and a substituted or unsubstituted C2-C10 alkynyl group.
In a preferred embodiment, R is1、R2Each independently represents an unsubstituted C1-C10 alkyl group or an unsubstituted C2-C10 alkenyl group.
In a preferred embodiment, the unsubstituted C1-C10 alkyl group is selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, n-hexyl, isohexyl, sec-hexyl, n-heptyl, isoheptyl, sec-heptyl, n-octyl, isooctyl, sec-octyl, n-nonyl, isononyl, sec-nonyl, n-decyl, isodecyl, cyclopentyl, cyclohexyl, cycloheptyl, methylcyclopentyl, methylcyclohexyl.
In a preferred embodiment, the unsubstituted C2-C10 alkenyl group is selected from any one of vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, isopentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl.
In a more preferred embodiment, R is1、R2Each independently represents any one of methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl.
In a most preferred embodiment, R is1Is selected from-CH2-、-CH2CH2-、-CH2CH2CH2-any of the above.
In a most preferred embodiment, R is2Is selected from-CH2CH2CH3、-CH2CH2CH2CH3、-CH2CH2CH2CH2CH2CH2CH2CH3、-CH(CH3)CH2CH3Any one of the above.
In one embodiment, the reaction feed for the coalescent includes at least:
wherein, R is3、R4Each independently represents any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C1-C20 alkoxy groupAnd (4) seed preparation.
In one embodiment, the
The molar ratio of (2-1): (1-2).
Preferably, the
In a molar ratio of (1.2-1): (1-1.2).
More preferably, the
In a molar ratio of 1.2: 1 or 1.1: 1 or 1: 1 or 1: 1.1 or 1: 1.2.
most preferably, the
In a molar ratio of 1: 1.
in a preferred embodiment, R is3、R4Each independently represents any one of a saturated aliphatic alkyl group having 1-10 carbon atoms, an unsaturated aliphatic alkyl group having 1-10 carbon atoms, and a cycloalkyl group having 3-10 carbon atoms.
In a more preferred embodiment, R is3Represents a saturated fatty alkyl group having a carbon number of 1 to 6.
In one embodiment, the saturated aliphatic alkyl group of C1-C6 is selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, n-hexyl, isohexyl, sec-hexyl, cyclopentyl, and cyclohexyl.
In a preferred embodiment, the saturated fatty alkyl group of C1-C6 is selected from any one of methyl, ethyl and n-propyl.
In a preferred embodiment, R is3Is selected from-CH2-、-CH2CH2-、-CH2CH2CH2-any of the above.
In a most preferred embodiment, R is3is-CH2-or-CH2CH2-。
In a more preferred embodiment, R is4Represents a saturated fatty alkyl group having a carbon number of 1 to 8.
In one embodiment, the saturated aliphatic alkyl group of C1-C8 is selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, n-hexyl, isohexyl, sec-hexyl, cyclopentyl, cyclohexyl, cycloheptyl, methylcyclopentyl, methylcyclohexyl, n-heptyl, isoheptyl, sec-heptyl, n-octyl, isooctyl, and sec-octyl.
In a preferred embodiment, R is4Is selected from-CH2CH2CH3、-CH2CH2CH2CH3、-CH2CH2CH2CH2CH2CH2CH2CH3、-CH(CH3)CH2CH3Any one of the above.
In a most preferred embodiment, R is4is-CH2CH2CH3or-CH2CH2CH2CH3。
In one embodiment, the reaction feed for the coalescent further includes catalyst I and catalyst II.
In one embodiment, the mass of catalyst I is
0.1-0.3 wt% of the total mass.
Preferably, the mass of the catalyst I is
0.2 wt% of the total mass.
In one embodiment, the catalyst I is boron trifluoride.
In one embodiment, the catalyst II is selected from one or more of sodium alkoxide, hydroxide, quaternary ammonium salt.
Preferably, the catalyst II is a mixture of sodium alkoxide or hydroxide and quaternary ammonium salt.
In a preferred embodiment, the mass ratio of the sodium alkoxide or hydroxide to the quaternary ammonium salt is (1-2): 1.
more preferably, the mass ratio of the sodium alkoxide or hydroxide to the quaternary ammonium salt is 1: 1.
in one embodiment, the sodium alkoxide or hydroxide has a mass of
0.3-1 wt% of the total mass.
Preferably, the mass of the sodium alkoxide or hydroxide is
0.6 wt% of the total mass.
In one embodiment, the sodium alkoxide is selected from one or more of sodium methoxide, sodium ethoxide, sodium diethoxide.
Preferably, the sodium alkoxide is sodium methoxide or sodium ethoxide.
In one embodiment, the hydroxide is selected from one or more of sodium hydroxide, potassium hydroxide, barium hydroxide.
Preferably, the hydroxide is potassium hydroxide.
In one embodiment, the quaternary ammonium salt is selected from one or more of tetramethylammonium bromide, tetraethylammonium bromide, tetrapropylammonium bromide, tetrabutylammonium bromide.
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
Reacting with a catalyst I at 60-200 ℃ for 1-4 h;
(2) and adding a catalyst II, and reacting at 60-200 ℃ for 3-7h 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
Reacting with a catalyst I at 90 ℃ for 4 h;
(2) and adding a catalyst II, and reacting at 120 ℃ for 4 hours to obtain the film-forming aid.
The invention adopts
The film-forming assistant prepared by using boron trifluoride, sodium alkoxide or mixture of hydroxide and quaternary ammonium salt as reactants and adopting step-by-step catalytic reaction as catalyst has good compatibility with any polymer emulsion, and can not cause emulsion breaking in the production process, especially when R is used3Methyl or ethyl, and R4 is n-propyl or n-butyl, not only can reduce the lowest film-forming temperature of the emulsion coating,
the rigid structure of the middle benzene ring can also regulate and control the distance between emulsion coating particles, and the structures such as alkoxy, 2-propanol and the like can inhibit the film-forming auxiliary agent from migrating to the surface of the emulsion coating, so that the film-forming performance of the film-forming auxiliary agent is obviously improved, the blocking resistance is good, and sufficient adhesive force can be obtained in a cold region to form a continuous film; meanwhile, the film forming additive prepared by the invention
The dosage is small, the boiling point is high, the performance of the styrene-acrylic emulsion can be particularly improved, the film forming property of the styrene-acrylic emulsion is improved, the formed coating has good scratch resistance, and the color development property, the luster and the weather resistance of the coating are obviously superior to those of the alcohol ester dodecafilming auxiliary agent sold in the market.
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 comprises 3 to 5 wt% of the styrene-acrylic emulsion by mass.
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.
Examples
Example 1
Example 1 provides a coalescent M1Said film-forming assistant M1The structural expression of (A) is as follows:
wherein, R is11represents-CH2-，R21represents-CH2CH2CH3；
The film-forming assistant M1The reaction raw materials are as follows:
(A1wherein, said R31represents-CH2-)、
(B1Wherein, said R41represents-CH2CH2CH3) Boron trifluoride and a catalyst II; a is described1、B1In a molar ratio of 1: 1; the mass of the boron trifluoride is A1、B10.1 wt% of the total mass; the catalyst II is a mixture of sodium methoxide and tetrapropylammonium bromide; the mass ratio of the sodium methoxide to the tetrapropylammonium bromide is 1: 1; the mass of the sodium methoxide is A1、B10.6 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
(1) a is to be1、B1Reacting with boron trifluoride at 90 ℃ for 4 h;
(2) adding a catalyst II, and reacting at 120 ℃ for 4 hours to obtain the film-forming assistant M1。
Example 2
Example 2 provides a coalescent M2Said film-forming assistant M2The structural expression of (A) is as follows:
wherein, R is12represents-CH2CH2-，R22represents-CH2CH2CH2CH3；
The film-forming assistant M2The reaction raw materials are as follows:
(A2wherein, said R32represents-CH2CH2-)、
(B2Wherein, said R42represents-CH2CH2CH2CH3) Boron trifluoride and a catalyst II; a is described2、B2In a molar ratio of 1: 1; the mass of the boron trifluoride is A2、B20.1 wt% of the total mass; the catalyst II is a mixture of sodium ethoxide and tetrabutylammonium bromide; the mass ratio of the sodium ethoxide to the tetrabutylammonium bromide is 1: 1; the mass of the sodium ethoxide is A2、B20.6 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
(1) a is to be2、B2Reacting with boron trifluoride at 90 ℃ for 4 h;
(2) adding a catalyst II, and reacting at 120 ℃ for 4 hours to obtain the film-forming assistant M2。
Example 3
Example 3 provides a coalescent M3Said film-forming assistant M3The structural expression of (A) is as follows:
wherein, R is13represents-CH2-，R23represents-CH2CH2CH3；
The film-forming assistant M3The reaction raw materials are as follows:
(A3wherein, said R33represents-CH2-)、
(B3Wherein, said R43represents-CH2CH2CH3) Boron trifluoride and a catalyst II; a is described3、B3In a molar ratio of 1.2: 1; the mass of the boron trifluoride is A3、B3Total mass0.1 wt% of; the catalyst II is a mixture of sodium ethoxide and tetrabutylammonium bromide; the mass ratio of the sodium ethoxide to the tetrabutylammonium bromide is 1: 1; the mass of the sodium ethoxide is A3、B30.6 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
(1) a is to be3、B3Reacting with boron trifluoride at 90 ℃ for 4 h;
(2) adding a catalyst II, and reacting at 120 ℃ for 4 hours to obtain the film-forming assistant M3。
Example 4
Example 4 provides a coalescent M4Said film-forming assistant M4The structural expression of (A) is as follows:
wherein, R is14represents-CH2-，R24represents-CH2CH2CH3；
The film-forming assistant M4The reaction raw materials are as follows:
(A4wherein, said R34represents-CH2-)、
(B4Wherein, said R44represents-CH2CH2CH3) Boron trifluoride and a catalyst II; a is described4、B4In a molar ratio of 1: 1.2; the mass of the boron trifluoride is A4、B40.1 wt% of the total mass; the catalyst II is a mixture of sodium methoxide and tetrapropylammonium bromide; the mass ratio of the sodium methoxide to the tetrapropylammonium bromide is 1: 1; the mass of the sodium methoxide is A4、B40.6 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
(1) a is to be4、B4Reacting with boron trifluoride at 90 ℃ for 4 h;
(2) adding a catalyst II, and reacting at 120 ℃ for 4 hours to obtain the film-forming assistant M4。
Example 5
Example 5 provides a coalescent M5Said film-forming assistant M5The structural expression of (A) is as follows:
wherein, R is15represents-CH2-，R25represents-CH2CH2CH3；
The film-forming assistant M5The reaction raw materials are as follows:
(A5wherein, said R35represents-CH2-)、
(B5Wherein, said R45represents-CH2CH2CH3) Boron trifluoride and a catalyst II; a is described5、B5In a molar ratio of 1: 1; the mass of the boron trifluoride is A5、B50.1 wt% of the total mass; the catalyst II is a mixture of potassium hydroxide and tetrapropylammonium bromide; the mass ratio of the potassium hydroxide to the tetrapropylammonium bromide is 1: 1; the mass of the potassium hydroxide is A5、B50.6 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
(1) a is to be5、B5Reacting with boron trifluoride at 90 ℃ for 4 h;
(2) adding a catalyst II, and reacting at 120 ℃ for 4 hours to obtain the film-forming assistant M5。
Example 6
Example 6 provides a coalescent M6The formation of the filmAuxiliary agent M6The structural expression of (A) is as follows:
wherein, R is16represents-CH2-，R26represents-CH2CH2CH3；
The film-forming assistant M6The reaction raw materials are as follows:
(A6wherein, said R36represents-CH2-)、
(B6Wherein, said R46represents-CH2CH2CH3) Boron trifluoride, sodium methoxide; a is described6、B6In a molar ratio of 1: 1; the mass of the boron trifluoride is A6、B60.1 wt% of the total mass; the mass of the sodium methoxide is A6、B60.6 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
(1) a is to be6、B6Reacting with boron trifluoride at 90 ℃ for 4 h;
(2) adding sodium methoxide, and reacting at 120 ℃ for 4h to obtain the film-forming additive M6。
Example 7
Example 7 provides a coalescent M7Said film-forming assistant M7The structural expression of (A) is as follows:
wherein, R is17represents-CH2-，R27represents-CH2CH2CH3；
The film-forming assistant M7The reaction raw materials are as follows:
(A7wherein, said R37represents-CH2-)、
(B7Wherein, said R47represents-CH2CH2CH3) A catalyst II; a is described7、B7In a molar ratio of 1: 1; the catalyst II is a mixture of sodium methoxide and tetrapropylammonium bromide; the mass ratio of the sodium methoxide to the tetrapropylammonium bromide is 1: 1; the mass of the sodium methoxide is A7、B70.6 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
a is to be7、B7Reacting with a catalyst II at 120 ℃ for 4h to obtain the film-forming assistant M7。
Example 8
Example 8 provides a coalescent M8Said film-forming assistant M8The structural expression of (A) is as follows:
wherein, R is18represents-CH2CH2CH2-，R28represents-CH2CH2CH2CH2CH2CH2CH2CH3；
The film-forming assistant M8The reaction raw materials are as follows:
(A8wherein, said R38represents-CH2CH2CH2-)、
(B8Wherein, said R48represents-CH2CH2CH2CH2CH2CH2CH2CH3) Trifluoro benzene and trifluoro benzeneBoron removal and catalyst II; a is described8、B8In a molar ratio of 1: 1; the mass of the boron trifluoride is A8、B80.1 wt% of the total mass; the catalyst II is a mixture of sodium methoxide and tetrapropylammonium bromide; the mass ratio of the sodium methoxide to the tetrapropylammonium bromide is 1: 1; the mass of the sodium methoxide is A8、B80.6 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
(1) a is to be8、B8Reacting with boron trifluoride at 90 ℃ for 4 h;
(2) adding a catalyst II, and reacting at 120 ℃ for 4 hours to obtain the film-forming assistant M8。
Example 9
Example 9 provides a coalescent M9Said film-forming assistant M9The structural expression of (A) is as follows:
wherein, R is19represents-CH2CH2-，R29represents-CH (CH)3)CH2CH3；
The film-forming assistant M9The reaction raw materials are as follows:
(A9wherein, said R39represents-CH2CH2-)、
(B9Wherein, said R49represents-CH (CH)3)CH2CH3) Boron trifluoride and a catalyst II; a is described9、B9In a molar ratio of 1: 1; the mass of the boron trifluoride is A9、B90.1 wt% of the total mass; the catalyst II is a mixture of sodium methoxide and tetrapropylammonium bromide; the mass ratio of the sodium methoxide to the tetrapropylammonium bromide is 1: 1; the mass of the sodium methoxide is A9、B90.6 wt% of the total mass.
The preparation method of the film-forming aid comprises the following steps:
(1) a is to be9、B9Reacting with boron trifluoride at 90 ℃ for 4 h;
(2) adding a catalyst II, and reacting at 120 ℃ for 4 hours to obtain the film-forming assistant M9。
Performance testing
1. Film forming temperature: respectively mixing the film-forming aid described in examples 1-9 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 10 ℃ and is marked as A, the temperature is 10-20 ℃ 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 film-forming aids of examples 1-9 were taken and the boiling points of the film-forming aids of examples 1-9 were determined by a boiling point analyzer, wherein the boiling point was 270 ℃ lower than A, the boiling point was 270 ℃ and 280 ℃ lower than B, and the boiling point was 280 ℃ higher than C, respectively, and the results are shown in Table 1.
3. Compatibility: respectively mixing the film-forming aid described in examples 1-9 and the emulsion BLJ-8600H according to a mass ratio of 4: 100, and judging whether the film-forming aid is compatible with the emulsion polymer or not by a DSC analysis method, wherein the film-forming aid with good compatibility is marked as A, the film-forming aid with good compatibility is marked as B, the film-forming aid with poor compatibility is marked 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 | B | A | A |
| Example 2 | A | C | A |
| Example 3 | B | B | A |
| Example 4 | B | A | A |
| Example 5 | B | A | A |
| Example 6 | B | A | A |
| Example 7 | B | A | A |
| Example 8 | A | C | B |
| Example 9 | A | C | B |
4. Film forming property: respectively mixing the film-forming aid described in example 1, the alcohol ester dodecafilm-forming aid and the emulsion BLJ-8600H according to a mass ratio of 4: 100, where M represents the test coalescent described in example 1 and W represents the alcohol ester dodecacoalescent, and the test results are shown in figure 1.
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 (10)
1. A coalescent, wherein the coalescent has the structural formula:
wherein, R is1、R2Each independently represents any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C10 carboxyl group, and a substituted or unsubstituted C1-C10 amide group.
2. The coalescent of claim 1, wherein the reaction feed of the coalescent comprises at least:
wherein, R is3、R4Each independently represents any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, and a substituted or unsubstituted C1-C20 alkoxy group.
3. The coalescing agent of claim 2, wherein the coalescing agent is a surfactant
The molar ratio of (2-1): (1-2).
4. The coalescing agent of claim 2 or 3, wherein R is3、R4Each independently represents any one of a saturated aliphatic alkyl group having 1-10 carbon atoms, an unsaturated aliphatic alkyl group having 1-10 carbon atoms, and a cycloalkyl group having 3-10 carbon atoms.
5. The coalescing agent of claim 4, wherein R is3Represents a saturated fatty alkyl group having a carbon number of 1 to 6.
6. The coalescing agent of claim 4, wherein R is4Represents a saturated fatty alkyl group having a carbon number of 1 to 8.
7. The coalescent of claim 2, wherein the reaction feed of the coalescent further comprises catalyst I and catalyst II.
8. The coalescent of claim 7, wherein the catalyst II is selected from one or more of sodium alkoxide, hydroxide, and quaternary ammonium salt.
9. The coalescing agent of claim 8, wherein the quaternary ammonium salt is selected from one or more of tetramethylammonium bromide, tetraethylammonium bromide, tetrapropylammonium bromide, tetrabutylammonium bromide.
10. A process for the preparation of a coalescent according to any one of claims 7 to 9, comprising the steps of:
(1) will be provided with
Reacting with a catalyst I at 60-200 ℃ for 1-4 h;
(2) and adding a catalyst II, and reacting at 60-200 ℃ for 3-7h to obtain the film-forming aid.
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