CN107311891B - A kind of preparation method of imines deicer - Google Patents
A kind of preparation method of imines deicer Download PDFInfo
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- CN107311891B CN107311891B CN201710451658.8A CN201710451658A CN107311891B CN 107311891 B CN107311891 B CN 107311891B CN 201710451658 A CN201710451658 A CN 201710451658A CN 107311891 B CN107311891 B CN 107311891B
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- deicer
- imines
- diamine
- preparation
- nitrile
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
Abstract
The invention discloses a kind of preparation methods of imines deicer, it includes the following steps: that step 1. reacts the alkene organic compound of nitrile group-containing with excessive diamine by a certain percentage, end of reaction removes excessive diamine, to obtain the diamine that one end is blocked by itrile group alkane；Step 2. reacts the product obtained by step 1 with aldehydes or ketones class compound, and removes the moisture of generation, to obtain the imines deicer.The present invention passes through the obtained imines deicer of above method, after chance water resolves into corresponding amine, it can be reacted with isocyano and generate allophanamide bond structure, either there is fabulous physical property as water-repellent paint or sealant and adhesive, so, the obtained imines deicer of the present invention has the characteristics that at low cost, storge quality is stable, water removal rate is fast, is obviously improved to material physical property, and to sum up, the present invention is a kind of preparation method of ideal imines deicer.
Description
Technical field
The invention belongs to organic compound synthesis technical fields, and in particular to a kind of preparation method of imines deicer.
Background technique
Polyurethane material has good toughness, wearability, adhesiveness and resistance to ag(e)ing, in water-repellent paint, sealant, glue
Glutinous agent field, which has, greatly applies.Polyurethane material can be divided into mono-component polyurethane material and two component polyurethane material by component
Material, wherein bi-component is polyurethane material common type.Compared with bi-component polyurethane ester material, mono-component polyurethane material has
The advantages such as construction is simple, easy to operate, curing rate are controllable, product is not easy to foaming, still, since mono-component polyurethane material exists
Isocyano can be reacted with the water in system or air when solidification generates a large amount of bubbles, to influence the physical of material
Can, therefore selecting suitable deicer is the important content of mono-component polyurethane material.
Epoxy resin is high with hardness, dielectric properties are good, adhesive strength is excellent, steady performance, in sealant, knot
The fields such as structure glue, binder, coating have very big application, and are widely used in each department of national economy production.Epoxy
Resin material can be divided into one-component epoxy resin material and bi-component epoxide-resin material by component, due to the ring in epoxy resin
Oxygen groups reactivity is higher, with general curing agent act on when react comparatively fast, when as one pack system can not long-term preservation, therefore
Bi-component is the common type of epoxide resin material.Compared with bi-component epoxide-resin material, one-component epoxy resin material tool
There are the advantages such as easy for construction, easy to operate, curing rate is controllable, therefore one-component epoxy resin material applies city with very big
?.The presence of moisture influences the performance of epoxy hardener to a certain extent, and then influences the adhesive property of epoxide resin material, because
This selects important content of the suitable deicer as one-component epoxy resin material.
Patent CN103865310A discloses a kind of preparation method of polyurethane water-proof paint deicer, described in this patent
Deicer is stated as oxazole alkanes, and oxazolidine meets water and resolves into amido alcohol, and amido alcohol and the isocyanates root in polyurethane system are anti-
It should be to play the role of crosslinking curing.The deicer of the method preparation can be used only in polyurethane system, cannot be used in asphalt mixtures modified by epoxy resin
Resin system, and amido alcohol reacts one end with isocyano and generates urethane linkages one end generation urea bond, and film performance is bad.
Patent CN104004441A discloses a kind of single-component epoxy priming paint and preparation method thereof, the curing agent category of preparation
In kitimine, the method uses initial reactant of the uncapped diamine as epoxy hardener, excessive to the consumption of ketone,
There is a problem of that higher cost, curing rate are slower.Simultaneously primary amine curing agent and epoxy resin reaction post-crosslinking spend greatly, into
And influence coating property.
Imine linkage is unstable to water electrode, it can the moisture in absorption system or air decomposed, therefore imines
Compound can be as the deicer of polyurethane and epoxy material；Corresponding amine is generated when imines is reacted with water simultaneously, amine can
It is reacted with the isocyanates root in polyurethane material and the epoxy group in epoxide resin material, to play the work of crosslinking curing
With therefore, imines deicer can be used as the curing agent of mono-component polyurethane material and one-component epoxy resin material, still
The prior art can not also provide the preparation method of the imines deicer of complete set, as the technical staff of the industry, very
It is necessary to break through to the technology, the preparation and use of imines deicer are realized.
Summary of the invention
To realize above-mentioned technical functionality, it is described that technical scheme is as follows: it includes the following steps:
Step 1. reacts the alkene organic compound of nitrile group-containing with excessive diamine by a certain percentage, end of reaction
Excessive diamine is removed, to obtain the diamine that one end is blocked by itrile group alkane；
Step 2. reacts the product obtained by step 1 with aldehydes or ketones class compound, and removes the moisture of generation, to obtain
The imines deicer.
The alkene organic compound of above-mentioned nitrile group-containing is preferred are as follows: acrylonitrile, methacrylonitrile, 2- butene nitrile, 3- butene nitrile,
One of 2- allyl acetonitrile, 3 pentene nitrile, 3,7- dimethyl -6- octenes nitrile or more than one mixtures arbitrarily matched.
The alkene organic compound of nitrile group-containing and the molar ratio of diamine are preferably 1: 2~14 in above-mentioned steps 1.
Above-mentioned diamine is preferably ethylenediamine, 1,2- propane diamine, Putriscine, 2 methyl pentamethylenediamine, 1,3- hexamethylene two
One of methylamine, cyclohexanediamine, isophorone diamine, m-xylene diamine, dimethyl-dicyclohexylmethane diamine or it is a kind of with
The mixture of upper any proportion.
Above-mentioned aldehydes or ketones compound is preferably formaldehyde, acetaldehyde, n-butanal, isobutylaldehyde, salicylide, benzaldehyde, furfural, isophthalic
One of oxygroup benzaldehyde, cyclohexanone, cyclopentanone, -2 butanone of 3- methyl, methyl ethyl ketone, acetophenone or methyl iso-butyl ketone (MIBK) or one
The mixture of kind any of the above proportion.
Imines deicer prepared by the present invention is applicable to polyurethane material and epoxide resin material field, according to not
Same application is tested referring to corresponding national standard.
Beneficial effects of the present invention: the present invention passes through the obtained imines deicer of above method, implementation letter
It, can be anti-with isocyano after list is easy production, and the imines deicer chance water of this patent preparation resolves into corresponding amine
Allophanamide bond structure should be generated, either there is fabulous physical property as water-repellent paint or sealant and adhesive, so,
By above method to imines deicer may be used as monocomponent polyurethane material and single component epoxy material
Curing agent has the characteristics that at low cost, storge quality is stable, water removal rate is fast, is obviously improved to material physical property；To sum up,
The present invention is a kind of preparation method of ideal imines deicer.
Specific embodiment
The present invention is further described through below with reference to embodiment.
In order to better explain the present invention, the present invention is done below with reference to embodiment and is further illustrated, but is of the invention
Content is not limited solely to the following examples.
Embodiment 1
Step 1 is added 228g's in the 500ml three-necked flask equipped with blender, thermometer, condenser and constant pressure funnel
Cyclohexanediamine (2 moles), by the way that acrylonitrile 53g (1 mole) is added dropwise into system in constant pressure funnel 1h, control dropping temperature 30 ±
It 2 DEG C, is added dropwise and continues to stir 1h, excessive cyclohexanediamine is removed by way of vacuum distillation, obtains N- propionitrile-hexamethylene two
Amine；
167g step is added in step 2 in the 500ml three-necked flask equipped with blender, thermometer, condenser and constant pressure funnel
The propionitrile of N- made from rapid 1-cyclohexanediamine (1 mole), by the way that acetophenone 120g is added dropwise in constant pressure funnel 2h into system, (1 rubs
You), 35 ± 2 DEG C of dropping temperature are controlled, is added dropwise and continues to stir 1h, the moisture of generation is removed by way of vacuum distillation,
Required imines deicer is obtained, cooling is sealed.
Embodiment 2
Step 1 is added 148g's in the 500ml three-necked flask equipped with blender, thermometer, condenser and constant pressure funnel
1,2- propane diamine (2 moles) controls dropping temperature by the way that 2- butene nitrile 67g (1 mole) is added dropwise into system in constant pressure funnel 1h
It 30 ± 2 DEG C, is added dropwise and continues to stir 1h, excessive 1,2- propane diamine is removed by way of vacuum distillation, obtains N- butyronitrile-
1,2 propane diamine；
141g step is added in step 2 in the 500ml three-necked flask equipped with blender, thermometer, condenser and constant pressure funnel
N- butyronitrile -1,2 propane diamine (1 mole) made from rapid 1, n-butanal 72g is added dropwise into system in 2h by constant pressure funnel, and (1 rubs
You), 35 ± 2 DEG C of dropping temperature are controlled, is added dropwise and continues to stir 1h, the moisture of generation is removed by way of vacuum distillation,
Required imines deicer is obtained, cooling is sealed.
Embodiment 3
Imines deicer prepared by example 1 and example 2 is applied to polyurethane water-proof paint, with specific reference to formula (matter
Measure part) and operating procedure it is as follows:
1 single-component polyurethane water-proof paint formula of table
| Polyethers 2000 | 140 |
| Polyethers 3050 | 60 |
| Dispersing agent KH550 | 0.4 |
| Chlorinated paraffin 52 | 100 |
| Kaolin | 140 |
| Coarse whiting (800 mesh) | 320 |
| TDI | 34 |
| No. 120 solvents | 120 |
| Organotin | 0.7 |
| Deicer prepared by embodiment 1 | 17.5 |
| Deicer prepared by embodiment 2 | 13 |
Polyethers, dispersing agent, chlorinated paraffin 52 are added in three-necked flask and is heated to 120~130 DEG C, is slowly added to kaolin
And TDI and solvent is added in 120~130 DEG C of vacuum dehydration 2h in coarse whiting when cooling to 90 DEG C, organotin is added in 80 DEG C of reaction 2h
Continue 80 DEG C to react 1 hour, is divided to two parts for reacted liquid, is separately added into embodiment 1 and embodiment 2 in ratio shown in table 1
The imines deicer of preparation, 80 DEG C are continued to stir half an hour, cooling discharging film, referring to national standard GB/T 19250- after seven days
2013 test correlated performances.
The performance parameter of single-component polyurethane water-proof paint obtained by 2 examples detailed above of table
Table 2 gives imines deicer prepared by embodiment 1 and embodiment 2 and is used as polyurethane water-proof paint products obtained therefrom
Performance parameter, it can be seen from Table 2 that, imines deicer prepared by the present invention solidifies as single-component polyurethane water-proof paint
When agent, products obtained therefrom performance can reach GB/T 19250-2013 technical standard, and imines deicer prepared by the present invention is not
It is singly confined to single-component polyurethane water-proof paint, may be also used in one-component polyurethane sealant and monocomponent polyurethane gluing
Agent can reach corresponding national standard by test, and those skilled in the art can be made with claim according to the present invention
Equivalent replacement.
Embodiment 4
Step 1 is added 272g's in the 500ml three-necked flask equipped with blender, thermometer, condenser and constant pressure funnel
M-xylene diamine (2 moles) controls dropping temperature by the way that 3- butene nitrile 67g (1 mole) is added dropwise into system in constant pressure funnel 1h
It 30 ± 2 DEG C, is added dropwise and continues to stir 1h, excessive m-xylene diamine is removed by way of vacuum distillation, obtains N- butyronitrile-
M-xylene diamine；
203g step is added in step 2 in the 500ml three-necked flask equipped with blender, thermometer, condenser and constant pressure funnel
The butyronitrile of N- made from rapid 1-m-xylene diamine (1 mole), by the way that cyclohexanone 98g is added dropwise in constant pressure funnel 2h into system, (1 rubs
You), 35 ± 2 DEG C of dropping temperature are controlled, is added dropwise and continues to stir 1h, the moisture of generation is removed by way of vacuum distillation,
Required imines deicer is obtained, cooling is sealed.
Embodiment 5
Step 1 is added 120g's in the 500ml three-necked flask equipped with blender, thermometer, condenser and constant pressure funnel
Ethylenediamine (2 moles) controls dropping temperature 30 ± 2 by the way that acrylonitrile 53g (1 mole) is added dropwise into system in constant pressure funnel 1h
DEG C, it is added dropwise and continues to stir 1h, excessive ethylenediamine is removed by way of vacuum distillation, obtains N- propionitrile-ethylenediamine；
113g step is added in step 2 in the 500ml three-necked flask equipped with blender, thermometer, condenser and constant pressure funnel
The propionitrile of N- made from rapid 1-ethylenediamine (1 mole), by the way that benzaldehyde 106g (1 mole) is added dropwise into system in constant pressure funnel 2h,
35 ± 2 DEG C of dropping temperature of control is added dropwise and continues to stir 1h, the moisture of generation is removed by way of vacuum distillation, is obtained
Required imines deicer, cooling are sealed.
Embodiment 6
Imines deicer prepared by example 4 and example 5 is applied to epoxy resin floor coatings coating, with specific reference to matching
Side's (mass parts) and operating procedure are as follows:
3 single component epoxy primer base formula of table
| E-44 epoxy resin | 100 |
| Iso-octyl glycidyl ether | 30 |
| DMP-30 | 2.4 |
| Quartz sand | 200 |
| Deicer prepared by embodiment 4 | 41.8 |
| Deicer prepared by embodiment 5 | 29.5 |
Epoxy resin, iso-octyl glycidyl ether, DMP-30 are added in three-necked flask and is heated to 120~130 DEG C, slowly
Quartz sand is added and cools to 80 DEG C in 120~130 DEG C of vacuum dehydration 2h, is divided to two parts for gained liquid, in ratio shown in table 3 point
Not Jia Ru the imines deicer for preparing of embodiment 4 and embodiment 5, continue to stir half an hour, cooling discharging film, reference after seven days
National standard tests correlated performance.
The performance parameter of single component epoxy floor coatings coating obtained by 4 examples detailed above of table
| Detection project | National standard | Example 1 | Example 2 |
| Surface drying time/h | ≤6 | 2 | 3 |
| Compression strength/MPa | ≥60 | 72 | 76 |
| Adhesion strength/MPa | ≥2.0 | 2.4 | 2.6 |
| Pencil hardness/H | ≥3 | 4 | 4 |
| Chemical resistance | Film is complete | Film is complete | Film is complete |
Table 4 gives imines deicer prepared by embodiment 4 and embodiment 5 and is used as obtained by epoxy resin floor coatings coating
The performance parameter of product, it can be seen from Table 4 that, imines deicer prepared by the present invention is used as single component epoxy coating
When curing agent, products obtained therefrom performance can reach national standard technical standard.
Finally, it is stated that: imines deicer prepared by the present invention be not confined to singly single-component polyurethane water-proof paint and
Single component epoxy coating may be also used in one-component polyurethane sealant, single-component polyurethane adhesive, single-component epoxy
Resin sealer, single component epoxy adhesive can reach corresponding national standard by test.Above embodiments are not
Technology and application scheme described in the invention are limited, those skilled in the art can be with claim according to the present invention work etc.
With replacement.
Claims (2)
1. a kind of preparation method of imines deicer, it is characterised in that: it uses following steps to obtain:
Step 1. reacts the alkene organic compound of nitrile group-containing with excessive diamine by a certain percentage, and end of reaction removes
Excessive diamine, to obtain the diamine that one end is blocked by itrile group alkane；The alkene organic compound of the nitrile group-containing are as follows: third
One of alkene nitrile, methacrylonitrile, 2- butene nitrile, 3- butene nitrile or more than one mixtures arbitrarily matched；Above-mentioned binary
Amine be one of ethylenediamine, 1,2- propane diamine, Putriscine, 2 methyl pentamethylenediamine, 1,3- hexamethylene dimethylamine or it is a kind of with
The mixture of upper any proportion；
Step 2. reacts the product obtained by step 1 with aldehydes or ketones class compound, and removes the moisture of generation, described to obtain
Imines deicer；Above-mentioned aldehyde be one of formaldehyde, acetaldehyde, n-butanal, isobutylaldehyde, salicylide, benzaldehyde or it is a kind of with
The mixture of upper any proportion；Above-mentioned ketone compound be one of cyclohexanone, cyclopentanone, -2 butanone of 3- methyl or it is a kind of with
The mixture of upper any proportion.
2. a kind of preparation method of imines deicer according to claim 1, it is characterised in that: contain in the step 1
The alkene organic compound of itrile group and the molar ratio of diamine are 1: 2~14.
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| EP4157918B1 (en) | 2020-05-29 | 2024-04-10 | Basf Se | Amphoterically-modified oligopropyleneimine ethoxylates for improved stain removal of laundry detergents |
| WO2021239453A1 (en) | 2020-05-29 | 2021-12-02 | Unilever Ip Holdings B.V. | A liquid laundry composition |
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