CN105061347A - Novel oxazolidine, preparation method, application, and mono-component polyurethane waterproof paint - Google Patents
Novel oxazolidine, preparation method, application, and mono-component polyurethane waterproof paint Download PDFInfo
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- CN105061347A CN105061347A CN201510455213.8A CN201510455213A CN105061347A CN 105061347 A CN105061347 A CN 105061347A CN 201510455213 A CN201510455213 A CN 201510455213A CN 105061347 A CN105061347 A CN 105061347A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/2875—Monohydroxy compounds containing tertiary amino groups
Abstract
The invention discloses novel oxazolidine, a preparation method, application, and mono-component polyurethane waterproof paint. The novel oxazolidine is named as 4-mehtyl-3-(2-phenylcarbinol)-1,3-oxazolidine. The novel oxazolidine is used as a latent curing agent of the mono-component polyurethane waterproof paint. During the production process of the waterproof paint, the novel oxazolidine is added into the raw materials, one naked hydroxy group of the novel oxazolidine will react with the polyurethane prepolymer formed by the raw materials, thus the novel oxazolidine is grafted to the polyurethane prepolymer, and the novel oxazolidine (latent curing agent) can be more evenly dispersed in the waterproof paint. If the waterproof paint is stored for a long time, the grafted novel oxazolidine will be dissolved out continuously, the stability of the waterproof paint is improved, the latent curing effect is improved, and avoided is the phenomenon that the latent curing agent is precipitated from the mono-component polyurethane waterproof paint or the latent curing agent aggregates in the waterproof paint. After the waterproof paint is used, the quality of the film formed by the waterproof paint is improved.
Description
Technical field
The invention belongs to polyurethane additive technical field, be specifically related to a kind of novel oxazole alkane, preparation method, application and mono-composition poyurethane water-proof paint.
Background technology
Polyurethane material is one of most widely used general, material that best performance is different, is divided into mono-component polyurethane product and two component polyurethane product from composition.The mainly applied product of current mono-component polyurethane has monocomponent polyurethane adhesive, one-component polyurethane sealant, mono-composition poyurethane water-proof paint etc.Compared to two component polyurethane product, mono-component polyurethane product eliminates the step of stirring, more easy to operate and construction, nor needs to add the chainextenders such as mocha, and environmental protection more, meets modern development idea.
Mono-component polyurethane refers in particular to the urethane resin of NCO base end-blocking, its curing mechanism is after polyurethane products are exposed to air, NCO base in urethane and the water cross-linking reaction film forming in air, but the generation of carbonic acid gas can be attended by, easily produce bubble (reaction formula one).The carbon dioxide gas that mono-component polyurethane product produces in the curing process is known from experience makes polyurethane surface or producing bubbles inside, both affects finished appearance, and has a strong impact on again the mechanical property of finished product.And it is very large by envrionment temperature and humidity effect, under high temperature, high humidity environment, curing speed is very fast, cause internal porosity more greatly, more.What these two shortcomings were serious hinders further developing of mono-component polyurethane product.
Reaction formula one:
2RNCO+H
2O→RNHCONHR+CO
2↑
In mono-component polyurethane product, Tian Jia oxazolidine latent curing agent, can solve above-mentioned two problems in theory completely.The curing mechanism of oxazole alkanes latent curing agent product is: the speed of response of water and oxazolidine is far longer than the reaction of water and NCO base, when latent curing type one-pack polyurethane water-proof paint runs into the moisture in air, preferential and oxazole alkanes latent curing agent generation hydrolysis reaction (reaction formula two) of water, generate the active hydrogen compounds containing amino and hydroxyl, again with the NCO radical reaction (reaction formula three) in product, generate carbamate and urea groups, this reaction produces without gas, solves the textural defect such as material pin hole, bubble.
Reaction formula two:
Reaction formula three:
The single-component polyurethane water-proof paint of Han oxazolidine class latent curing agent of the prior art is in standing storage, oxazole alkanes latent curing agent in it has precipitation or clustering phenomena in waterproof paint, and the consequence directly caused is exactly have a large amount of bubbles after single-component polyurethane water-proof paint film forming.
Summary of the invention
Technical problem to be solved by this invention is for above shortcomings in prior art, a kind of novel oxazole alkane, preparation method, application and mono-composition poyurethane water-proof paint are provided, the polyurethane prepolymer precursor reactant that this novel oxazole alkane has an exposed hydroxyl can be formed with raw material, make novel oxazole alkane be grafted on base polyurethane prepolymer for use as become be integrated, the novel oxazole alkane as latent curing agent disperse in waterproof paint evenly.
The technical scheme that solution the technology of the present invention problem adopts is to provide a kind of novel oxazole alkane, and its name is called 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines, and chemical structural formula is:
The present invention also provides a kind of preparation method of novel oxazole alkane, comprises the following steps:
(1) by the 2-fluorobenzaldehyde of 20 ~ 30 mass parts and the organic solvent N of 10 ~ 100 mass parts, dinethylformamide mixes, add 10 ~ 20 mass parts oxazolidines again, add the first catalyzer salt of wormwood, react 1 ~ 10 hour at 130 ~ 150 DEG C, obtain 2-(3-oxazolidinyl) phenyl aldehyde;
(2) by the first organic solvent mixing of 2-(3-oxazolidinyl) phenyl aldehyde of 10 ~ 20 mass parts, the second catalyzer trifluoromethanesulfonic acid scandium, 100 ~ 500 mass parts, react 1 ~ 10 hour at 80 ~ 100 DEG C, obtain benzoxazine Bing oxazolidine;
(3) by the second organic solvent mixing of the benzoxazine Bing oxazolidine of 10 ~ 15 mass parts, 30 ~ 100 mass parts, add methyl Grignard, there is grignard reaction, add ammonium chloride saturated solution cancellation reaction again, obtain 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines.
Preferably, the described first catalyzer salt of wormwood in described step (1) is 20 ~ 30 mass parts.
Preferably, the described second catalyzer trifluoromethanesulfonic acid scandium in described step (2) is 5 ~ 10 mass parts.
Preferably, the temperature of the grignard reaction of described step (3) is-5 ~ 5 DEG C.
Preferably, described first organic solvent is one or more in ethylene dichloride, benzene, tetracol phenixin;
Described second organic solvent is one or more in ethylene dichloride, benzene, tetracol phenixin.
The present invention also provides a kind of above-mentioned novel oxazole alkane as the application of the latent curing agent of mono-composition poyurethane water-proof paint.
The present invention also provides a kind of mono-composition poyurethane water-proof paint, and the composition of raw materials preparing this mono-composition poyurethane water-proof paint comprises: polyether glycol, isocyanic ester, catalyzer, above-mentioned latent curing agent, softening agent, filler, solvent.
Preferably, described polyether glycol is 25 ~ 35 mass parts;
Described isocyanic ester is 3 ~ 3.8 mass parts;
Described catalyzer is 0.05 ~ 0.5 mass parts;
Described latent curing agent is 1 ~ 1.5 mass parts;
Described softening agent is 10 ~ 20 mass parts;
Described filler is 30 ~ 45 mass parts;
Described solvent is 8 ~ 10 mass parts.
Preferably, described polyether glycol is polyether glycol DL-2000D, polyether glycol DL-3000D, polyether glycol DL-1000D, one or more in polyether glycol EP-330N;
Described isocyanic ester is tolylene diisocyanate (TDI) and/or diphenylmethanediisocyanate (MDI); It is further preferred that described tolylene diisocyanate is TDI (80/20); Described diphenylmethanediisocyanate is diphenylmethanediisocyanate MDI50, diphenylmethanediisocyanate MDI100.
Described catalyzer is dibutyl tin laurate and/or stannous octoate;
Described softening agent is clorafin, dibutyl phthalate, one or more in dioctyl phthalate (DOP);
Described filler is talcum powder, kaolin, water-ground limestone, one or more in light calcium carbonate;
Described solvent is solvent oil 120#, solvent oil 150#, one or more in dimethylbenzene.
Preferably, the composition of raw materials preparing this mono-composition poyurethane water-proof paint also comprises pigment, and described pigment is 1 ~ 1.5 mass parts, and described pigment is one or more in carbon black, red iron oxide, iron oxide brown.
Add above-mentioned latent curing agent in mono-component polyurethane product after, after standing storage, can not defoaming effect be affected, improve the stability of mono-component polyurethane product performance.
Novel oxazole alkane in the present invention, its name is called 4-methyl-3-(2-phenylcarbinol base)-1, 3 oxazolidines, this novel oxazole alkane is applied to the latent curing agent of mono-composition poyurethane water-proof paint, in the production process of mono-composition poyurethane water-proof paint, novel oxazole alkane is joined after in the raw material preparing waterproof paint, the polyurethane prepolymer precursor reactant that this novel oxazole alkane has an exposed hydroxyl can be formed with raw material, novel oxazole alkane is made to be grafted on base polyurethane prepolymer for use as to become to be integrated (as reaction formula four), novel oxazole alkane as latent curing agent disperse in waterproof paint evenly.After mono-composition poyurethane water-proof paint prolonged storage, novel oxazole alkane after grafting also can not therefrom be separated out, thus improve the stability of waterproof paint, improve latent solidification effect, avoid precipitation or the clustering phenomena of the latent curing agent in single-component polyurethane water-proof paint of the prior art.Mono-composition poyurethane water-proof paint in the present invention experienced by the standing storage phase, after enabling, in film process, novel oxazole alkane after grafting runs into the water in air, will decompose (principle is with reaction formula two), still can eliminate bubble completely, thus improve the quality of forming film of waterproof paint.
Reaction formula four:
Accompanying drawing explanation
Fig. 1 is the cross-sectional view that mono-composition poyurethane water-proof paint in the embodiment of the present invention 2 carries out the diaphragm of film;
Fig. 2 is the cross-sectional view that mono-composition poyurethane water-proof paint in comparative example 1 of the present invention carries out the diaphragm of film.
Embodiment
For making those skilled in the art understand technical scheme of the present invention better, below in conjunction with the drawings and specific embodiments, the present invention is described in further detail.
Embodiment 1
The present embodiment provides a kind of preparation method of novel oxazole alkane, comprises the following steps:
(1) by the 2-fluorobenzaldehyde of 20 mass parts and the organic solvent N of 50 mass parts, dinethylformamide mixes, add again 20 mass parts oxazolidine, 30 mass parts the first catalyzer salt of wormwood, react 10 hours at 130 DEG C, obtain 2-(3-oxazolidinyl) phenyl aldehyde;
(2) by the first organic solvent ethylene dichloride mixing of the second catalyzer trifluoromethanesulfonic acid scandium of 2-(3-oxazolidinyl) phenyl aldehyde of 20 mass parts, 5 mass parts, 400 mass parts, react 10 hours at 80 DEG C, obtain benzoxazine Bing oxazolidine;
(3) by the second organic solvent ethylene dichloride mixing of the benzoxazine Bing oxazolidine of 10 mass parts, 100 mass parts, add methyl Grignard, there is grignard reaction, the temperature of grignard reaction is-5 DEG C, add ammonium chloride saturated solution cancellation reaction again, obtain 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines.
The present embodiment provides a kind of above-mentioned preparation method the novel oxazole alkane prepared, and its name is called 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines, and chemical structural formula is:
The present embodiment provides above-mentioned novel oxazole alkane as the application of the latent curing agent of mono-composition poyurethane water-proof paint.
The present embodiment provides a kind of mono-composition poyurethane water-proof paint, and the composition of raw materials preparing this mono-composition poyurethane water-proof paint comprises: polyether glycol, isocyanic ester, catalyzer, above-mentioned latent curing agent, softening agent, filler, solvent
Described polyether glycol is 25 mass parts;
Described isocyanic ester is 3.8 mass parts;
Described catalyzer is 0.5 mass parts;
Described latent curing agent is 1.5 mass parts;
Described softening agent is 20 mass parts;
Described filler is 45 mass parts;
Described solvent is 10 mass parts;
Wherein, described polyether glycol is polyether glycol DL-2000D, polyether glycol DL-3000D, polyether glycol DL-1000D, one or more in polyether glycol EP-330N;
Described isocyanic ester is tolylene diisocyanate and/or diphenylmethanediisocyanate;
Described catalyzer is dibutyl tin laurate and/or stannous octoate;
Described softening agent is clorafin, dibutyl phthalate, one or more in dioctyl phthalate (DOP);
Described filler is talcum powder, kaolin, water-ground limestone, one or more in light calcium carbonate;
Described solvent is solvent oil 120#, solvent oil 150#, one or more in dimethylbenzene.
Preferably, the composition of raw materials preparing this mono-composition poyurethane water-proof paint comprises: also comprise pigment, and described pigment is 1 ~ 1.5 mass parts, and described pigment is one or more in carbon black, red iron oxide, iron oxide brown.
Novel oxazole alkane in the present embodiment, its name is called 4-methyl-3-(2-phenylcarbinol base)-1, 3 oxazolidines, this novel oxazole alkane is applied to the latent curing agent of mono-composition poyurethane water-proof paint, in the production process of mono-composition poyurethane water-proof paint, novel oxazole alkane is joined after in the raw material preparing waterproof paint, the polyurethane prepolymer precursor reactant that this novel oxazole alkane has an exposed hydroxyl can be formed with raw material, novel oxazole alkane is made to be grafted on base polyurethane prepolymer for use as to become to be integrated (as reaction formula four), novel oxazole alkane as latent curing agent disperse in waterproof paint evenly.After mono-composition poyurethane water-proof paint prolonged storage, novel oxazole alkane after grafting also can not therefrom be separated out, thus improve the stability of waterproof paint, improve latent solidification effect, avoid precipitation or the clustering phenomena of the latent curing agent in single-component polyurethane water-proof paint of the prior art.Mono-composition poyurethane water-proof paint in the present embodiment experienced by the standing storage phase, after enabling, in film process, novel oxazole alkane after grafting runs into the water in air, will decompose (principle is with reaction formula two), still can eliminate bubble completely, thus improve the quality of forming film of waterproof paint.
Reaction formula four:
Embodiment 2
The present embodiment provides a kind of preparation method of novel oxazole alkane, comprises the following steps:
(1) by the 2-fluorobenzaldehyde of 22 mass parts and the organic solvent N of 20 mass parts, dinethylformamide (DMF) mixes, add again 18 mass parts oxazolidine, 28 mass parts the first catalyzer salt of wormwood, react 6 hours at 150 DEG C, obtain 2-(3-oxazolidinyl) phenyl aldehyde;
(2) by the first organic solvent ethylene dichloride (DCE) mixing of the second catalyzer trifluoromethanesulfonic acid scandium of 2-(3-oxazolidinyl) phenyl aldehyde of 10 mass parts, 7 mass parts, 500 mass parts, react 2 hours at 90 DEG C, obtain benzoxazine Bing oxazolidine;
(3) by the second organic solvent ethylene dichloride (DCE) mixing of the benzoxazine Bing oxazolidine of 12 mass parts, 50 mass parts, add methyl Grignard (methyl-magnesium-bromide), there is grignard reaction, the temperature of grignard reaction is 0 DEG C, add ammonium chloride saturated solution cancellation reaction again, obtain 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines.
The present embodiment provides a kind of above-mentioned preparation method the novel oxazole alkane prepared, and its name is called 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines, and chemical structural formula is:
The present embodiment provides above-mentioned novel oxazole alkane as the application of the latent curing agent of mono-composition poyurethane water-proof paint.
The present embodiment provides a kind of mono-composition poyurethane water-proof paint, and the composition of raw materials preparing this mono-composition poyurethane water-proof paint comprises: polyether glycol, isocyanic ester, catalyzer, above-mentioned latent curing agent, softening agent, filler, solvent
Described polyether glycol is 30 mass parts;
Described isocyanic ester is 3.2 mass parts;
Described catalyzer is 0.2 mass parts;
Described latent curing agent is 1.2 mass parts;
Described softening agent is 18 mass parts;
Described filler is 42 mass parts;
Described solvent is 9 mass parts;
Described pigment is 1 mass parts;
Wherein, described polyether glycol is the mixture of polyether glycol DL-2000D and polyether glycol EP-330N, and wherein, the mass ratio of polyether glycol DL-2000D and polyether glycol EP-330N is 1:1;
Described isocyanic ester is tolylene diisocyanate (80/20);
Described catalyzer is dibutyl tin laurate;
Described softening agent is one or more in clorafin;
Described filler is the mixture of talcum powder and water-ground limestone, and wherein, the mass ratio of talcum powder and water-ground limestone is 2:1;
Described solvent is solvent oil 120#;
Described pigment is carbon black.
The present embodiment provides a kind of preparation method of above-mentioned mono-composition poyurethane water-proof paint, operates, comprise the following steps according to above-mentioned formula:
By polyether glycol (technical grade, blue star east is large), softening agent, filler, pigment adds in reactor, 110 DEG C ± 5 DEG C, below vacuum tightness 0.095MPa dewaters 2h, be cooled to 70 DEG C, add tolylene diisocyanate (80/20), be warming up to 80 DEG C ± 5 DEG C reaction 2.5h, then add catalyst dibutyltin dilaurylate reaction 0.5h.Add latent curing agent 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines and solvent again, keep 80 DEG C ± 5 DEG C reaction 1h in whipping process, obtain above-mentioned mono-composition poyurethane water-proof paint.
Novel oxazole alkane in the present embodiment, its name is called 4-methyl-3-(2-phenylcarbinol base)-1, 3 oxazolidines, this novel oxazole alkane is applied to the latent curing agent of mono-composition poyurethane water-proof paint, in the production process of mono-composition poyurethane water-proof paint, novel oxazole alkane is joined after in the raw material preparing waterproof paint, the polyurethane prepolymer precursor reactant that this novel oxazole alkane has an exposed hydroxyl can be formed with raw material, novel oxazole alkane is made to be grafted on base polyurethane prepolymer for use as to become to be integrated (as reaction formula four), novel oxazole alkane as latent curing agent disperse in waterproof paint evenly.After mono-composition poyurethane water-proof paint prolonged storage, novel oxazole alkane after grafting also can not therefrom be separated out, thus improve the stability of waterproof paint, improve latent solidification effect, avoid precipitation or the clustering phenomena of the latent curing agent in single-component polyurethane water-proof paint of the prior art.Mono-composition poyurethane water-proof paint in the present embodiment experienced by the standing storage phase, after enabling, in film process, novel oxazole alkane after grafting runs into the water in air, will decompose (principle is with reaction formula two), still can eliminate bubble completely, thus improve the quality of forming film of waterproof paint.
Reaction formula four:
Comparative example 1
The latent curing agent prepared in the composition of raw materials of the mono-composition poyurethane water-proof paint in this comparative example 1 is
3-methyl-2-phenyl-1,3 oxazolidines, the consumption of the latent curing agent in this comparative example is 1.27 times (calculate according to the active hydrogen equivalent weight after hydrolysis and get) of the consumption of the latent curing agent in comparative example 2, identical all with embodiment 2 of all the other components in composition of raw materials in this comparative example and content, identical with embodiment 2 of preparation method's condition.Wherein, the structural formula of 3-methyl-2-phenyl-1,3 oxazolidine is:
Respectively the mono-composition poyurethane water-proof paint in the mono-composition poyurethane water-proof paint prepared in embodiment 2, this comparative example 1 is placed 6 months in normal temperature environment curing room, temperature: 25 DEG C ± 5 DEG C, humidity: 40%-60%; The material (oxazolidine removing upper strata about 1/3 is lighter, likely can precipitate into position, liquid upper strata), from the part feeding film of remainder, contrast diaphragm visual appearance (cross section of the diaphragm of film is the position best embodying bubble in diaphragm), the surface drying time of investigation film respectively, do solid work time, mechanical property (tensile property).Diaphragm cutter is cut cross section, the mono-composition poyurethane water-proof paint be illustrated in figure 1 in the embodiment of the present invention 2 carries out the cross-sectional view of the diaphragm of film, and the mono-composition poyurethane water-proof paint be illustrated in figure 2 in comparative example 1 of the present invention carries out the cross-sectional view of the diaphragm of film.As seen from Figure 1, the diaphragm that the mono-composition poyurethane water-proof paint in the embodiment of the present invention 2 carries out film is fine and close, does not have bubble, fullys meet the effect eliminating bubble.As seen from Figure 2, there is a lot of bubble the diaphragm inside that the mono-composition poyurethane water-proof paint in comparative example 1 of the present invention carries out film, illustrates that mono-composition poyurethane water-proof paint in comparative example 1 is after standing storage, latent curing agent wherein
3-methyl-2-phenyl-1,3 oxazolidine skewness or precipitation in mono-composition poyurethane water-proof paint, thus greatly reduce latent solidification effect, namely reduce the effect eliminating bubble.
Table 1
| Numbering | Surface drying time/h | The time of doing solid work/h |
| Comparative example 1 | 8 | 22 |
| Embodiment 2 | 4 | 6 |
Table 1 is surface drying time and the correlation data of actual drying time of single-component polyurethane water-proof paint in comparative example 1 and embodiment 2, the surface drying time of the single-component polyurethane water-proof paint as can be seen from Table 1 in embodiment 2 and actual drying time are respectively well below the single-component polyurethane water-proof paint in comparative example 1, this illustrates after standing storage, latent curing agent skewness in waterproof paint of the single-component polyurethane water-proof paint in comparative example 1, cause some polyurethanes performed polymer can only lean on and water cross-linking reaction film forming, therefore surface drying time and actual drying time increase greatly.And the latent curing agent of single-component polyurethane water-proof paint in embodiment 2 is evenly distributed in waterproof paint, film forming is even, therefore surface drying time and actual drying time reduce greatly.
Table 2
| Numbering | Tensile strength/MPa | Elongation at break/% |
| Comparative example 1 | 2.2 | 510 |
| Embodiment 2 | 4.0 | 850 |
Table 2 is the tensile strength of single-component polyurethane water-proof paint in comparative example 1 and embodiment 2 and the correlation data of elongation at break, the tensile strength of the single-component polyurethane water-proof paint as can be seen from Table 2 in embodiment 2 and elongation at break are respectively far away higher than the single-component polyurethane water-proof paint in comparative example 1, this illustrates because the existence of the bubble for the single-component polyurethane water-proof paint in example 1 causes tensile strength and elongation at break all greatly to reduce respectively, that is in the single-component polyurethane water-proof paint in embodiment 2 owing to there is no bubble so tensile strength and elongation at break all improve respectively greatly.
Embodiment 3
The present embodiment provides a kind of preparation method of novel oxazole alkane, comprises the following steps:
(1) by the 2-fluorobenzaldehyde of 30 mass parts and the organic solvent N of 10 mass parts, dinethylformamide mixes, add again 12 mass parts oxazolidine, 25 mass parts the first catalyzer salt of wormwood, at 140 DEG C react 1 hour, obtain 2-(3-oxazolidinyl) phenyl aldehyde;
(2) by the first organic solvent-benzene mixing of the second catalyzer trifluoromethanesulfonic acid scandium of 2-(3-oxazolidinyl) phenyl aldehyde of 12 mass parts, 6 mass parts, 300 mass parts, react 6 hours at 100 DEG C, obtain benzoxazine Bing oxazolidine;
(3) by the second organic solvent-benzene mixing of the benzoxazine Bing oxazolidine of 15 mass parts, 30 mass parts, add methyl Grignard, there is grignard reaction, the temperature of grignard reaction is 5 DEG C, add ammonium chloride saturated solution cancellation reaction again, obtain 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines.
The present embodiment provides a kind of above-mentioned preparation method the novel oxazole alkane prepared, and its name is called 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines, and chemical structural formula is:
The present embodiment provides above-mentioned novel oxazole alkane as the application of the latent curing agent of mono-composition poyurethane water-proof paint.
The present embodiment provides a kind of mono-composition poyurethane water-proof paint, and the composition of raw materials preparing this mono-composition poyurethane water-proof paint comprises: polyether glycol, isocyanic ester, catalyzer, above-mentioned latent curing agent, softening agent, filler, solvent
Described polyether glycol is 35 mass parts;
Described isocyanic ester is 3.6 mass parts;
Described catalyzer is 0.4 mass parts;
Described latent curing agent is 1 mass parts;
Described softening agent is 10 mass parts;
Described filler is 40 mass parts;
Described solvent is 8.5 mass parts;
Described pigment is 1.5 mass parts;
Wherein, described polyether glycol is polyether glycol DL-1000D;
Described isocyanic ester is diphenylmethanediisocyanate MDI50;
Described catalyzer is dibutyl tin laurate and stannous octoate, and wherein, the mass ratio of dibutyl tin laurate and stannous octoate is 1:1;
Described softening agent is dibutyl phthalate;
Described filler is talcum powder;
Described solvent is solvent oil 150#;
Described pigment is red iron oxide.
Embodiment 4
The present embodiment provides a kind of preparation method of novel oxazole alkane, comprises the following steps:
(1) by the 2-fluorobenzaldehyde of 28 mass parts and the organic solvent N of 100 mass parts, dinethylformamide mixes, add again 16 mass parts oxazolidine, 20 mass parts the first catalyzer salt of wormwood, react 8 hours at 135 DEG C, obtain 2-(3-oxazolidinyl) phenyl aldehyde;
(2) by the first organic solvent carbon tetrachloride mixing of the second catalyzer trifluoromethanesulfonic acid scandium of 2-(3-oxazolidinyl) phenyl aldehyde of 16 mass parts, 8 mass parts, 200 mass parts, react 1 hour at 85 DEG C, obtain benzoxazine Bing oxazolidine;
(3) by the second organic solvent carbon tetrachloride mixing of the benzoxazine Bing oxazolidine of 11 mass parts, 80 mass parts, add methyl Grignard, there is grignard reaction, the temperature of grignard reaction is 0 DEG C, add ammonium chloride saturated solution cancellation reaction again, obtain 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines.
The present embodiment provides a kind of above-mentioned preparation method the novel oxazole alkane prepared, and its name is called 4-methyl 3-(2-phenylcarbinol base)--1,3 oxazolidines, and chemical structural formula is:
The present embodiment provides above-mentioned novel oxazole alkane as the application of the latent curing agent of mono-composition poyurethane water-proof paint.
The present embodiment provides a kind of mono-composition poyurethane water-proof paint, and the composition of raw materials preparing this mono-composition poyurethane water-proof paint comprises: polyether glycol, isocyanic ester, catalyzer, above-mentioned latent curing agent, softening agent, filler, solvent
Described polyether glycol is 32 mass parts;
Described isocyanic ester is 3.4 mass parts;
Described catalyzer is 0.3 mass parts;
Described latent curing agent is 1.4 mass parts;
Described softening agent is 16 mass parts;
Described filler is 32 mass parts;
Described solvent is 9.5 mass parts;
Described pigment is 1.4 mass parts;
Wherein, described polyether glycol is polyether glycol DL-3000D;
Described isocyanic ester is diphenylmethanediisocyanate MDI100;
Described catalyzer is stannous octoate;
Described softening agent is the mixture of dibutyl phthalate, dioctyl phthalate (DOP), wherein, dibutyl phthalate, the mass ratio of dioctyl phthalate (DOP) is 2:1;
Described filler is light calcium carbonate;
Described solvent is dimethylbenzene;
Described pigment is iron oxide brown.
Embodiment 5
The present embodiment provides a kind of preparation method of novel oxazole alkane, comprises the following steps:
(1) by the 2-fluorobenzaldehyde of 26 mass parts and the organic solvent N of 80 mass parts, dinethylformamide mixes, add again 10 mass parts oxazolidine, 22 mass parts the first catalyzer salt of wormwood, at 145 DEG C react 4 hours, obtain 2-(3-oxazolidinyl) phenyl aldehyde;
(2) by the first organic solvent ethylene dichloride mixing of the second catalyzer trifluoromethanesulfonic acid scandium of 2-(3-oxazolidinyl) phenyl aldehyde of 14 mass parts, 10 mass parts, 100 mass parts, react 8 hours at 95 DEG C, obtain benzoxazine Bing oxazolidine;
(3) by the second organic solvent ethylene dichloride mixing of the benzoxazine Bing oxazolidine of 13 mass parts, 60 mass parts, add methyl Grignard, there is grignard reaction, the temperature of grignard reaction is 2 DEG C, add ammonium chloride saturated solution cancellation reaction again, obtain 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines.
The present embodiment provides a kind of above-mentioned preparation method the novel oxazole alkane prepared, and its name is called 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines, and chemical structural formula is:
The present embodiment provides above-mentioned novel oxazole alkane as the application of the latent curing agent of mono-composition poyurethane water-proof paint.
The present embodiment provides a kind of mono-composition poyurethane water-proof paint, and the composition of raw materials preparing this mono-composition poyurethane water-proof paint comprises: polyether glycol, isocyanic ester, catalyzer, above-mentioned latent curing agent, softening agent, filler, solvent
Described polyether glycol is 28 mass parts;
Described isocyanic ester is 3 mass parts;
Described catalyzer is 0.05 mass parts;
Described latent curing agent is 1.3 mass parts;
Described softening agent is 14 mass parts;
Described filler is 30 mass parts;
Described solvent is 8 mass parts;
Described pigment is 1.2 mass parts;
Wherein, described polyether glycol is polyether glycol EP-330N;
Described isocyanic ester is the mixture of diphenylmethanediisocyanate MDI50 and diphenylmethanediisocyanate MDI100, and wherein, the mass ratio of diphenylmethanediisocyanate MDI50 and diphenylmethanediisocyanate MDI100 is 3:4;
Described catalyzer is dibutyl tin laurate;
Described softening agent is dioctyl phthalate (DOP);
Described filler is kaolin;
Described solvent is the mixture of solvent oil 120#, solvent oil 150#, and wherein, the mass ratio of solvent oil 120#, solvent oil 150# is 4:5;
Described pigment is carbon black.
Be understandable that, the illustrative embodiments that above embodiment is only used to principle of the present invention is described and adopts, but the present invention is not limited thereto.For those skilled in the art, without departing from the spirit and substance in the present invention, can make various modification and improvement, these modification and improvement are also considered as protection scope of the present invention.
Claims (10)
1. a novel oxazole alkane, is characterized in that, its name is called 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines, chemical structural formula is:
2. a preparation method for novel oxazole alkane, is characterized in that, comprises the following steps:
(1) by the 2-fluorobenzaldehyde of 20 ~ 30 mass parts and the organic solvent N of 10 ~ 100 mass parts, dinethylformamide mixes, add 10 ~ 20 mass parts oxazolidines again, add the first catalyzer salt of wormwood, react 1 ~ 10 hour at 130 ~ 150 DEG C, obtain 2-(3-oxazolidinyl) phenyl aldehyde;
(2) by the first organic solvent mixing of 2-(3-oxazolidinyl) phenyl aldehyde of 10 ~ 20 mass parts, the second catalyzer trifluoromethanesulfonic acid scandium, 100 ~ 500 mass parts, react 1 ~ 10 hour at 80 ~ 100 DEG C, obtain benzoxazine Bing oxazolidine;
(3) by the second organic solvent mixing of the benzoxazine Bing oxazolidine of 10 ~ 15 mass parts, 30 ~ 100 mass parts, add methyl Grignard, grignard reaction occurs, then add ammonium chloride saturated solution cancellation reaction, obtain 4-methyl-3-(2-phenylcarbinol base)-1,3 oxazolidines.
3. the preparation method of novel oxazole alkane according to claim 2, is characterized in that, the described first catalyzer salt of wormwood in described step (1) is 20 ~ 30 mass parts.
4. the preparation method of novel oxazole alkane according to claim 2, is characterized in that, the described second catalyzer trifluoromethanesulfonic acid scandium in described step (2) is 5 ~ 10 mass parts.
5. the preparation method of novel oxazole alkane according to claim 2, is characterized in that, the temperature of the grignard reaction of described step (3) is-5 ~ 5 DEG C.
6. the preparation method of the novel oxazole alkane according to claim 2 ~ 5 any one, is characterized in that, described first organic solvent is one or more in ethylene dichloride, benzene, tetracol phenixin;
Described second organic solvent is one or more in ethylene dichloride, benzene, tetracol phenixin.
7. the novel oxazole alkane in claim 1 is as the application of the latent curing agent of mono-composition poyurethane water-proof paint.
8. a mono-composition poyurethane water-proof paint, is characterized in that, the composition of raw materials preparing this mono-composition poyurethane water-proof paint comprises: the latent curing agent in polyether glycol, isocyanic ester, catalyzer, claim 7, softening agent, filler, solvent.
9. mono-composition poyurethane water-proof paint according to claim 8, is characterized in that, described polyether glycol is 25 ~ 35 mass parts;
Described isocyanic ester is 3 ~ 3.8 mass parts;
Described catalyzer is 0.05 ~ 0.5 mass parts;
Described latent curing agent is 1 ~ 1.5 mass parts;
Described softening agent is 10 ~ 20 mass parts;
Described filler is 30 ~ 45 mass parts;
Described solvent is 8 ~ 10 mass parts.
10. mono-composition poyurethane water-proof paint according to claim 8 or claim 9, it is characterized in that, described polyether glycol is polyether glycol DL-2000D, polyether glycol DL-3000D, polyether glycol DL-1000D, one or more in polyether glycol EP-330N;
Described isocyanic ester is tolylene diisocyanate and/or diphenylmethanediisocyanate;
Described catalyzer is dibutyl tin laurate and/or stannous octoate;
Described softening agent is clorafin, dibutyl phthalate, one or more in dioctyl phthalate (DOP);
Described filler is talcum powder, kaolin, water-ground limestone, one or more in light calcium carbonate;
Described solvent is solvent oil 120#, solvent oil 150#, one or more in dimethylbenzene.
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| CN108300253A (en) * | 2017-07-31 | 2018-07-20 | 王敏 | A kind of modified mono-composition poyurethane water-proof paint |
| CN112280449A (en) * | 2020-10-16 | 2021-01-29 | 中国航发北京航空材料研究院 | Single-component infrared coating for repairing and preparation method thereof |
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Application publication date: 20151118 |