CN107011503A - Cashew pnenolic aldehyde amine epoxy curing agent and preparation method that a kind of thiocarbamide is modified - Google Patents
Cashew pnenolic aldehyde amine epoxy curing agent and preparation method that a kind of thiocarbamide is modified Download PDFInfo
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- CN107011503A CN107011503A CN201710357554.0A CN201710357554A CN107011503A CN 107011503 A CN107011503 A CN 107011503A CN 201710357554 A CN201710357554 A CN 201710357554A CN 107011503 A CN107011503 A CN 107011503A
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- Prior art keywords
- thiocarbamide
- modified
- curing agent
- pnenolic aldehyde
- amine
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
- C08G14/08—Ureas; Thioureas
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Lubricants (AREA)
Abstract
The invention discloses the cashew pnenolic aldehyde amine epoxy curing agent that a kind of thiocarbamide is modified, it is made up of thiocarbamide, fatty amine, anacardol and formaldehyde.The present invention obtains optimal raw material by many experiments screening and constituted and proportioning and its optimal preparation technology, the present invention first pass through thiocarbamide fatty amine is modified, again with anacardol, formaldehyde reaction generation cashew pnenolic aldehyde amine hardener, due to there are long chain hydrocarbon groups in molecular structure in anacardol, the pliability of film after solidification can be improved, also the viscosity of curing agent can be significantly reduced, due to introducing thiocarbamide in the molecule, is obviously improved the low temperature curing properties of cashew pnenolic aldehyde amine.Test result indicates that, the cashew pnenolic aldehyde amine hardener that the present invention is prepared using preferred feedstock is a kind of low viscosity, and hypotoxicity, the excellent curing agent of low temperature curing properties achieves extraordinary unexpected technique effect compared with prior art.
Description
Technical field
The present invention relates to a kind of curing agent, and in particular to a kind of viscosity is low, and toxicity is low, and low temperature is that curable thiocarbamide is modified
Cashew pnenolic aldehyde amine epoxy curing agent and preparation method, belong to technical field of polymer materials.
Background technology
Epoxy resin has excellent adhesion strength and antiseptic property, is widely used in many fields.Epoxy
Resin must be valuable with the use of ability with curing agent, and curing agent species mainly has polyamide, phenolic aldehyde amine, acid anhydrides etc..But it is sour
Acid anhydride needs ability cured epoxy resin, polyamide and the general normal temperature curable epoxy resin of phenolic aldehyde amine under high temperature, but in low temperature
When (less than 5 DEG C), curing reaction can not be all participated in well, reach that certain intensity needs long time, hardening time is long.Sulphur
Urea can significantly reduce the solidification temperature of epoxy resin, there is the curing agent that thiocarbamide is modified with fatty amine, but molecular weight in the prior art
Smaller, volatility is larger, still suffers from certain toxicity.Also there is the phenol prepared after thiocarbamide modified fatty amine with phenol, formaldehyde reaction
Aldehyde amine hardener, but viscosity is larger, it has not been convenient to construct.
Therefore, on the basis of prior art, it would be highly desirable to research and develop a kind of small toxicity, viscosity is small, low temperature curing properties are good
Epoxy hardener.
The content of the invention
Goal of the invention:The purpose of the present invention is that in view of the shortcomings of the prior art, screening raw material by many experiments, there is provided one
Kind viscosity is low, and toxicity is low, and low temperature is the cashew pnenolic aldehyde amine epoxy curing agent that curable thiocarbamide is modified;Another mesh of the invention
The preparation method for being to provide the epoxy hardener.
Technical scheme, to realize object above, the technical solution adopted by the present invention is:
The cashew pnenolic aldehyde amine epoxy curing agent that a kind of thiocarbamide is modified, it is characterised in that it is by thiocarbamide, fatty amine, anacardol
It is made with formaldehyde.
Preferably, the cashew pnenolic aldehyde amine epoxy curing agent that a kind of above-described thiocarbamide is modified, it is by mol ratio
For 1~2:1:1:1~3 waist thiocarbamide, fatty amine, anacardol and formaldehyde are made.
Preferably, the cashew pnenolic aldehyde amine epoxy curing agent that a kind of above-described thiocarbamide is modified, described fat
Amine is ethylenediamine, diethylenetriamine, triethylene tetramine or TEPA;Described formaldehyde is the formaldehyde that volumetric concentration is 37%
Solution or paraformaldehyde solid.
The preparation method for the cashew pnenolic aldehyde amine epoxy curing agent that a kind of thiocarbamide of the present invention is modified, it includes following step
Suddenly:
(1) fatty amine and thiocarbamide are added in reaction bulb, under the protection of nitrogen, Hybrid Heating stirring, then heating rises
Temperature is risen to 120~135 DEG C, then 1~3h of back flow reaction naturally cools to by temperature to 40~60 DEG C after thiocarbamide melts completely
Room temperature, obtains thiocarbamide modified amine;
(2) the thiocarbamide modified amine for preparing anacardol and step (1) is sequentially added in reaction bulb, and Hybrid Heating is stirred
Mix, be then heated to 40~60 DEG C, start that formalin is added dropwise;
(3) after formaldehyde completion of dropwise addition, 90~110 DEG C are heated to, continues 1~3h of insulation reaction, then vacuumizes and remove
The water gone in system, obtains thiocarbamide and is modified cashew pnenolic aldehyde amine epoxy curing agent.
Preferably, the preparation side for the cashew pnenolic aldehyde amine epoxy curing agent that a kind of thiocarbamide of the present invention is modified
Method, it comprises the following steps:
(1) fatty amine and thiocarbamide are added in reaction bulb, under the protection of nitrogen, Hybrid Heating stirring, then heating rises
Temperature is risen to 125~135 DEG C, then back flow reaction 3h naturally cools to room by temperature to 45~55 DEG C after thiocarbamide melts completely
Temperature, obtains thiocarbamide modified amine;
(2) the thiocarbamide modified amine for preparing anacardol and step (1) is sequentially added in reaction bulb, and Hybrid Heating is stirred
Mix, be then heated to 50 DEG C, start that formalin is added dropwise, control the rate of addition of formaldehyde, and control temperature to be no more than 100
℃;
(3) after formaldehyde completion of dropwise addition, 95~105 DEG C are heated to, continues insulation reaction 3h, then vacuumizes removing body
Water in system, obtains thiocarbamide and is modified cashew pnenolic aldehyde amine epoxy curing agent.
Preferably, the preparation method for the cashew pnenolic aldehyde amine epoxy curing agent that a kind of above-described thiocarbamide is modified,
Formalin is the formalin or paraformaldehyde solution that volumetric concentration is 37%.
Preferably, the preparation method for the cashew pnenolic aldehyde amine epoxy curing agent that a kind of above-described thiocarbamide is modified,
The mol ratio of described waist thiocarbamide, fatty amine, anacardol and formaldehyde is 1~2:1:1:1~3.
Beneficial effect:Compared to the prior art, the present invention has the following advantages:
The present invention obtains optimal raw material by many experiments screening and constituted and proportioning and its optimal preparation technology, this hair
It is bright first pass through thiocarbamide fatty amine is modified, again with anacardol, formaldehyde reaction generation cashew pnenolic aldehyde amine hardener, anacardol by
There are long chain hydrocarbon groups in molecular structure, the pliability of film after solidification can be improved, the viscosity of curing agent can be also significantly reduced,
Additionally, due to thiocarbamide is introduced in the molecule, it is obviously improved the low temperature curing properties of cashew pnenolic aldehyde amine.Experimental result
Show, the cashew pnenolic aldehyde amine hardener that the present invention is prepared using preferred feedstock is a kind of low viscosity, hypotoxicity, low-temperature setting
The curing agent of excellent performance, achieves extraordinary unexpected technique effect compared with prior art.
Embodiment
Embodiment 1
1st, a kind of thiocarbamide is modified cashew pnenolic aldehyde amine epoxy curing agent, and it includes following raw material:Thiocarbamide 76g, diethylenetriamine
103g, anacardol 304g, 37% formalin 81g.
2nd, thiocarbamide is modified the preparation method of cashew pnenolic aldehyde amine epoxy curing agent, and it comprises the following steps:
(1) the diethylenetriamine 103g of the weight and thiocarbamide 76g is added in reaction bulb, under the protection of nitrogen, mixed
Close heating stirring;50 ± 5 DEG C are heated to, temperature is risen to 130 ± 5 DEG C after thiocarbamide melts completely;Back flow reaction 3h is naturally cold
But to room temperature, that is, low viscosity, the thiocarbamide modified amine of buff are obtained;
(2) and then by anacardol 304g add in reaction bulb, Hybrid Heating stirring;Then 50 DEG C are warming up to, starts to be added dropwise
37% formalin 81g, controls the rate of addition of formaldehyde, temperature is no more than 100 DEG C;100 DEG C are then heated to continue to protect
Temperature reaction 3h;
(3) after reaction terminates, weighed after vacuumizing away the water in system, cooling, obtain thiocarbamide and be modified cashew pnenolic aldehyde amine ring
Oxygen curing agent 478g.
Embodiment 2
1st, a kind of thiocarbamide is modified cashew pnenolic aldehyde amine epoxy curing agent, and it includes following raw material:Thiocarbamide 76g, triethylene tetramine
146g, anacardol 304g, 37% formalin 81g.
2nd, thiocarbamide is modified the preparation method of cashew pnenolic aldehyde amine epoxy curing agent, and it comprises the following steps:
(1) diethylenetriamine 146g and thiocarbamide 76g is added in reaction bulb, under the protection of nitrogen, Hybrid Heating stirring;
50 ± 5 DEG C are heated to, temperature 130 ± 5 DEG C are risen to after thiocarbamide melts completely, back flow reaction 3h naturally cools to room temperature, i.e.,
Obtain low viscosity, the thiocarbamide modified amine of buff;
(2) and then by anacardol 304g add in reaction bulb, Hybrid Heating stirring;Then 50 DEG C are warming up to, starts to be added dropwise
37% formalin 81g, controls the rate of addition of formaldehyde, temperature is no more than 100 DEG C;100 DEG C are then heated to continue to protect
Temperature reaction 3h;
(3) after reaction terminates, weighed after vacuumizing away the water in system, cooling, obtain thiocarbamide and be modified cashew pnenolic aldehyde amine ring
Oxygen curing agent 521g.
Embodiment 3
1st, a kind of thiocarbamide is modified cashew pnenolic aldehyde amine epoxy curing agent, and it includes following raw material:Thiocarbamide 152g, diethylenetriamine
206g, anacardol 304g, 37% formalin 162g.
2nd, thiocarbamide is modified the preparation method of cashew pnenolic aldehyde amine epoxy curing agent, and it comprises the following steps:
(1) diethylenetriamine 206g and thiocarbamide 152g is added in reaction bulb, under the protection of nitrogen, Hybrid Heating is stirred
Mix;50 DEG C are heated to, temperature is risen to 135 DEG C after thiocarbamide melts completely;Back flow reaction 3h, naturally cools to room temperature, produces
To low viscosity, the thiocarbamide modified amine of buff;
(2) and then by anacardol 304g add in reaction bulb, Hybrid Heating stirring;Then 50 DEG C are warming up to, starts to be added dropwise
37% formalin 162g, controls the rate of addition of formaldehyde, temperature is no more than 100 DEG C;105 DEG C are then heated to continue to protect
Temperature reaction 3h;
(3) after reaction terminates, weighed after vacuumizing the water in removing system, cooling, obtain thiocarbamide and be modified cashew pnenolic aldehyde amine ring
Oxygen curing agent 686g.
Embodiment 4
1st, a kind of thiocarbamide is modified cashew pnenolic aldehyde amine epoxy curing agent, and it includes following raw material:Thiocarbamide 76g, diethylenetriamine
103g, anacardol 304g, paraformaldehyde 30g.
2nd, thiocarbamide is modified the preparation method of cashew pnenolic aldehyde amine epoxy curing agent, and it comprises the following steps:
(1) diethylenetriamine 103g and thiocarbamide 76g is added in reaction bulb, under the protection of nitrogen, Hybrid Heating stirring;
55 DEG C are heated to, temperature is risen to 130 DEG C after thiocarbamide melts completely;Back flow reaction 3h, naturally cools to room temperature, that is, obtains low
Viscosity, the thiocarbamide modified amine of buff;
(2) and then by anacardol 304g add in reaction bulb, Hybrid Heating stirring;Then 50 DEG C are warming up to, point 3 batches add
Enter paraformaldehyde 30g, control temperature is no more than 100 DEG C;Then heat to 105 DEG C and continue insulation reaction 3h;
(3) after reaction terminates, weighed after vacuumizing the water in removing system, cooling, obtain thiocarbamide and be modified cashew pnenolic aldehyde amine ring
Oxygen curing agent 478g.
The performance test of embodiment 5
Gained modified by cardanol amine hardener, is pressed in Example 4《The measure of adhesive viscosity》(GB/T 2794-
1995) tested.It is 1500mPa.s to measure curing agent viscosity at 25 DEG C;HClO is used again4It is 565 that method, which determines its amine value,.
By 100 part of 828 epoxy resin of mass parts, the curing agent is mixed with 25 parts, is stirred, respectively in the 5 DEG C of surveys of 25 DEG C of room temperature and low temperature
Try its presetting period, the presetting period is 6min at 25 DEG C, the presetting period is 30min at 5 DEG C.With with phenol, ethylenediamine, formaldehyde is
The curing agent T-31 (amine value 560) of raw material is compared, and normal temperature cure performance and low temperature curing properties will be well a lot, and T-31 is in low temperature
Under not gel solidification.
Described above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (7)
1. the cashew pnenolic aldehyde amine epoxy curing agent that a kind of thiocarbamide is modified, it is characterised in that it is by thiocarbamide, fatty amine, anacardol and
Formaldehyde is made.
2. the cashew pnenolic aldehyde amine epoxy curing agent that a kind of thiocarbamide according to claim 1 is modified, it is 1~2 by mol ratio:
1:1:1~3 waist thiocarbamide, fatty amine, anacardol and formaldehyde are made.
3. the cashew pnenolic aldehyde amine epoxy curing agent that described a kind of thiocarbamide according to claim 2 is modified, described fat
Amine is ethylenediamine, diethylenetriamine, triethylene tetramine or TEPA;Described formaldehyde is the formaldehyde that volumetric concentration is 37%
Solution or paraformaldehyde solid.
4. the preparation method for the cashew pnenolic aldehyde amine epoxy curing agent that the thiocarbamide described in any one of claims 1 to 3 is modified, it includes
Following steps:
(1) fatty amine and thiocarbamide are added in reaction bulb, under the protection of nitrogen, then Hybrid Heating stirring is heated to
40~60 DEG C, temperature is risen to 120~135 DEG C after thiocarbamide melts completely, then 1~3h of back flow reaction naturally cools to room
Temperature, obtains thiocarbamide modified amine;
(2) the thiocarbamide modified amine for preparing anacardol and step (1) is sequentially added in reaction bulb, Hybrid Heating stirring, so
After be heated to 40~60 DEG C, start be added dropwise formalin;
(3) after formaldehyde completion of dropwise addition, 90~110 DEG C are heated to, continues 1~3h of insulation reaction, then vacuumizes removing body
Water in system, obtains thiocarbamide and is modified cashew pnenolic aldehyde amine epoxy curing agent.
5. the preparation method for the cashew pnenolic aldehyde amine epoxy curing agent that a kind of thiocarbamide according to claim 4 is modified, it includes
Following steps:
(1) fatty amine and thiocarbamide are added in reaction bulb, under the protection of nitrogen, then Hybrid Heating stirring is heated to
45~55 DEG C, temperature is risen to 125~135 DEG C after thiocarbamide melts completely, then back flow reaction 3h naturally cools to room temperature, obtains
To thiocarbamide modified amine;
(2) the thiocarbamide modified amine for preparing anacardol and step (1) is sequentially added in reaction bulb, Hybrid Heating stirring, so
After be heated to 50 DEG C, start be added dropwise formalin, control formaldehyde rate of addition, and control temperature be no more than 100 DEG C;
(3) after formaldehyde completion of dropwise addition, 95~105 DEG C are heated to, continues insulation reaction 3h, then vacuumizes in removing system
Water, obtain thiocarbamide be modified cashew pnenolic aldehyde amine epoxy curing agent.
6. the preparation side for the cashew pnenolic aldehyde amine epoxy curing agent that a kind of thiocarbamide according to described in claim 4 or 5 is modified
Method, formalin is the formalin or paraformaldehyde solution that volumetric concentration is 37%.
7. the preparation side for the cashew pnenolic aldehyde amine epoxy curing agent that a kind of thiocarbamide according to described in claim 4 or 5 is modified
The mol ratio of method, described waist thiocarbamide, fatty amine, anacardol and formaldehyde is 1~2:1:1:1~3.
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Cited By (7)
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CN110615881A (en) * | 2019-08-20 | 2019-12-27 | 浙江万盛股份有限公司 | Preparation method of water-based epoxy curing agent |
CN113105721A (en) * | 2021-04-14 | 2021-07-13 | 中国人民解放军陆军工程大学 | Rapid hardening and solidifying material for soft sand texture, preparation method and application |
CN113480727A (en) * | 2021-06-08 | 2021-10-08 | 华南理工大学 | Preparation method of modified polyether amine epoxy resin curing agent |
CN113651764A (en) * | 2021-08-20 | 2021-11-16 | 浙江工业大学 | Synthesis method and application of heavy metal stabilizer |
CN113717339A (en) * | 2021-09-16 | 2021-11-30 | 上海交通大学 | Curing agent for reducing volatile matters of adhesive |
CN114031750A (en) * | 2021-11-24 | 2022-02-11 | 山东天茂新材料科技股份有限公司 | Low-temperature thin-coating type phenolic aldehyde amine curing agent and preparation method thereof |
CN118291071A (en) * | 2024-04-17 | 2024-07-05 | 佛山禾邦新材料科技有限公司 | Epoxy heat-conducting structural adhesive capable of realizing rapid positioning and curing at room temperature and preparation method thereof |
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CN103980463A (en) * | 2014-04-23 | 2014-08-13 | 中科院广州化学有限公司南雄材料生产基地 | Epoxy resin solvent-free low temperature curing agent, preparation method and application thereof |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110615881A (en) * | 2019-08-20 | 2019-12-27 | 浙江万盛股份有限公司 | Preparation method of water-based epoxy curing agent |
CN113105721A (en) * | 2021-04-14 | 2021-07-13 | 中国人民解放军陆军工程大学 | Rapid hardening and solidifying material for soft sand texture, preparation method and application |
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CN113480727A (en) * | 2021-06-08 | 2021-10-08 | 华南理工大学 | Preparation method of modified polyether amine epoxy resin curing agent |
CN113651764A (en) * | 2021-08-20 | 2021-11-16 | 浙江工业大学 | Synthesis method and application of heavy metal stabilizer |
CN113717339A (en) * | 2021-09-16 | 2021-11-30 | 上海交通大学 | Curing agent for reducing volatile matters of adhesive |
CN114031750A (en) * | 2021-11-24 | 2022-02-11 | 山东天茂新材料科技股份有限公司 | Low-temperature thin-coating type phenolic aldehyde amine curing agent and preparation method thereof |
CN118291071A (en) * | 2024-04-17 | 2024-07-05 | 佛山禾邦新材料科技有限公司 | Epoxy heat-conducting structural adhesive capable of realizing rapid positioning and curing at room temperature and preparation method thereof |
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Application publication date: 20170804 |