CN109467692A - A kind of non-isocyanate urea groups epoxy hardener - Google Patents
A kind of non-isocyanate urea groups epoxy hardener Download PDFInfo
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- CN109467692A CN109467692A CN201811103436.8A CN201811103436A CN109467692A CN 109467692 A CN109467692 A CN 109467692A CN 201811103436 A CN201811103436 A CN 201811103436A CN 109467692 A CN109467692 A CN 109467692A
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- urea groups
- epoxy hardener
- groups epoxy
- isocyanate urea
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
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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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4057—Carbamates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
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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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
- C08G2650/04—End-capping
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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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention provides a kind of non-isocyanate urea groups epoxy hardener, its formula composition includes dialkyl carbonate, diamine compounds and Amino End Group polymer, with diamine compounds ammonia esterification occurs for dialkyl carbonate at a certain temperature under catalyst, deviate from alkylol, the alkyl diamino-methyl formate of small molecule is obtained after reaction a period of time, with Amino End Group polymer condensation reaction occurs for alkyl diamino-methyl formate at a certain temperature under catalyst, deviate from alkylol, a kind of non-isocyanate urea groups epoxy hardener required for being obtained after reaction a period of time, this curing agent is a kind of thick liquid of low viscosity.The present invention joined polyether soft segments, urea bond inside epoxy hardener, so that the performances such as the toughness of epoxy resin, intensity and heat resistance have obtained comprehensive raising；Compared with traditional epoxy curing agent, the present invention has not only selected low toxicity or nontoxic in raw material, but also the product synthesized is also to be safe from harm, accomplished environmentally protective to human health for non-toxic product.
Description
Technical field
The invention belongs to technical field of polymer materials, and in particular to a kind of non-isocyanate urea groups epoxy hardener.
Background technique
Epoxy resin contains various polarity group and the very big epoxy group of activity, thus with metal, glass, cement, timber,
The various polarities material such as plastics, the especially material of high surface activity have very strong bonding force, while epoxy curing compound is interior
Poly- intensity is also very big, so its glue-joint strength is very high.It is substantially generated without low molecular weight volatile object when epoxy resin cure.It is corrosion-resistant
Property and dielectric properties are good.The corrosion of a variety of media such as energy acid and alkali resistance, salt, solvent after epoxy resin cure.
Although epoxy resin has These characteristics, simple epoxy resin itself does not have these performance characteristics, only
Have and uses his performance advantage of rear competence exertion by arranging in pairs or groups with curing agent in certain proportion.The type of epoxy hardener also very
It is more, it is arranged in pairs or groups using different curing agent, the performance of obtained epoxy resin is different, and the classification of epoxy resin includes following a few sides
Face:
(1) alkaline curing agent: aliphatic diamine, polyamines, aromatic polyamine, dicyandiamide, imidazoles, modified amine；
(2) acid curing agent: organic acid anhydride, boron trifluoride and complex compound；
(3) add-on type curing agent: fatty amines, aromatic series, cycloaliphatic ring class, modified amine, anhydride, Versamid and latent
Volt property amine；
(4) catalytic curing agent: three-level amine and imidazoles.
Cured above dose of application is up to amine curing agent, but in terms of amine curing agent is because of its toxicity, toughness, intensity
Deficiency causes it using being limited, and the polyetheramine containing ehter bond can substitute its application, but polyetheramine is poor in terms of heat resistance, Gu
The disadvantages of changing time and speed bad control.Therefore in recent years, everybody has excellent performance finding one kind, curing time and speed
Controllably, the epoxy curing agent that can be used under various circumstances, everybody has carried out many researchs to this, and Wang Honghua etc. is utilized
Rosin, fumaric acid and aminated compounds have prepared the rosin amide class epoxy hardener of a kind of application and powdery paints.Yang Yu
River etc. is prepared for a kind of ring that application is good with low-temperature setting, impact resistance using cardanol glycidyl ether and aminated compounds
Oxygen curing agent.
In order to solve, traditional epoxy hardener curing rate is too fast or excessively slow, heat resistance is bad, performance hair after solidification
Crisp, the problems such as toxicity is big.The present invention provides a kind of non-isocyanate urea groups type ring oxidant, and curing rate is adjustable, resistance to
Hot excellent and good toughness novel Curing Agents for Epoxy Resins.
Summary of the invention
It is an object of the invention to overcome the above technical problem, the present invention is by the rational principle to raw material, to molecule knot
Structure brand-new design, provides a kind of non-isocyanate urea groups type ring oxidant, curing rate is adjustable, excellent heat resistance and
The novel Curing Agents for Epoxy Resins of good toughness.
To achieve the above object, the technical solution used in the present invention is: to provide a kind of non-isocyanate urea groups epoxy solid
Agent, formula composition include dialkyl carbonate, diamine compounds and Amino End Group polymer, the chemical formula of epoxy hardener
Are as follows:
In formula: R2Represent C1 ~ C18 fatty group or alicyclic group or aromatic series base；
R3For polyether structure or alkylen structures.
The non-isocyanate urea groups epoxy hardener is by dialkyl carbonate and diamine compounds according to mole matching
Than 1:10 ~ 10:1, synthesis of alkyl diamino-methyl formate；Again by alkyl diamino-methyl formate and Amino End Group polymer according to rubbing
Your proportion is that 0.5:8 ~ 1:10 is synthesized.
The fatty group or alicyclic group or aromatic series base that the R1 of the dialkyl carbonate is C1 ~ C8, preferably carbonic acid two
Methyl esters, diethyl carbonate and dipropyl carbonate it is one or more.
R2 in the diamine compounds is C1 ~ C18 fatty group or alicyclic group or aromatic series base, preferably second two
Amine, 1,2- propane diamine, 1,3- propane diamine, 1,4- butanediamine, 1,6- hexamethylene diamine it is one or more.
Described Amino End Group polymer preferred D230, D400, D800's is one or more.
The synthesis of the alkyl diamino-methyl formate: dialkyl carbonate under catalyst at a certain temperature with diamines
Ammonia esterification occurs for class compound, deviates from alkylol, obtains the alkyl diamino acid first of small molecule after reacting a period of time
Ester,
The synthesis of the non-isocyanate urea groups epoxy hardener: alkyl diamino-methyl formate is under catalyst in certain temperature
Condensation reaction occurs for lower and Amino End Group polymer, deviates from alkylol, obtains a kind of required non-isocyanide after reacting a period of time
Acid esters urea groups epoxy hardener, this curing agent are a kind of thick liquid of low viscosity.
The preparation method of the non-isocyanate urea groups epoxy hardener, the specific steps are as follows:
(1) diamine compounds, dialkyl carbonate, catalysis the synthesis of alkyl diamino-methyl formate: are weighed by mass fraction
Agent A reacts 1 ~ 8h at 60 ~ 100 DEG C of normal pressure, rectifying, which goes out, reacts the alkylol generated, and rectifying column tip temperature is 60 ~ 80 DEG C,
Then 90 DEG C are increased the temperature to, deviates from remaining dialkyl carbonate in the case where vacuum degree is -0.07MPa, reaction equation is such as
Under:
(1)
In formula (1):
R1Represent the fatty group or alicyclic group or aromatic series base of C1 ~ C8；
R2Represent C1 ~ C18 fatty group or alicyclic group or aromatic series base；
Mol ratio 1:10 ~ 10:1 of the dialkyl carbonate and diamine compounds；
The dosage of the catalyst A is 0.001 ~ 5%.
(2) synthesis of non-isocyanate urea groups epoxy hardener: under the action of catalyst B, alkyl diamino acid first
Ester and amine terminated polyether are condensed, and carry out abjection alkylol under 80 ~ 200 DEG C of reaction temperature, vacuum degree -0.097MPa, after 1 ~ 10h
Alkylol stops reaction after reaching theoretical value, obtains light yellow viscous liquid non-isocyanate urea groups epoxy hardener, reacts
Equation is as follows:
(2)
In formula (2):
R2Represent C1 ~ C18 fatty group or alicyclic group or aromatic series base；
R3For polyether structure or alkylen structures；
The catalyst B dosage is 0.001 ~ 5%.
The mol ratio of the alkyl diamino-methyl formate and Amino End Group polymer is 0.5:8 ~ 1:10.
The catalyst A is the oxide or simple substance or hydride or alcoholates or organic base of alkali or alkaline earth metal,
Preferably potassium, potassium oxide, potassium methoxide, sodium, sodium oxide molybdena, sodium methoxide it is one or more.
The catalyst B is tin catalyst, titanium class catalyst, and tin catalyst is preferred: Dibutyltin oxide, octanoic acid are sub-
Tin, dibutyl tin dilaurate it is one or more, titanium class catalyst is preferred: tetraethyl titanate, tetraisopropyl titanate, metatitanic acid four
Butyl ester it is one or more.
Non-isocyanate urea groups epoxy hardener and epoxy resin cure: according to the obtained non-isocyanate of above-mentioned steps
Under room temperature or heating curing reaction occurs for urea groups epoxy hardener and epoxy resin, obtains function admirable, environmentally protective ring
Oxygen resin solidification product, reaction equation are as follows:
(3)
In above formula (3)Representing epoxy resin general formula includes bisphenol A type epoxy resin, bisphenol F type epoxy tree
Rouge, diglycidyl ether type epoxy resin etc..
In the step (3)The preferred bisphenol A-type of epoxy resin: E44, E51, E54, bisphenol-f type:
6458,6453, diglycidyl ether type: 662,664 it is one or more.
The temperature of curing reaction is preferably -5 ~ 130 DEG C, and curing time is preferred are as follows: 1min ~ 12 hour；And to ability after solidification
Product is tested for the property, and improves the tensile strength and elongation at break of epoxy resin.
Dimethyl carbonate used in this application is a kind of environmentally protective industrial chemicals, the phosgene of alternative severe toxicity,
Methylchloroformate, dimethyl suflfate etc. are used as methylating agent or carbonyl agent, improve the safety of production operation, reduce ring
Border pollution.Entire synthesis process " zero-emission ", does not use organic solvent, in synthesis process, dimethyl carbonate and amination
It closes object and reacts methanol removal, after Methanol Recovery, can be used as the raw material for preparing dimethyl carbonate, recycle, be a kind of environment
Friendly technical process.It is too crisp after general traditional epoxy resin cure, and intensity is not high, the epoxy hardener that the present invention is done
The inside joined polyether soft segments, to solve the problems, such as that epoxy resin is hard and crisp, and introduce urea bond, urea groups has
It is highly polar, the adhesive force of substrate is improved, and urea bond has improvement to the heat resistance of system, so that epoxy resin
The performances such as toughness, intensity and heat resistance have obtained comprehensive raising.
The beneficial effects of the present invention are: joined polyether soft segments, urea bond inside epoxy hardener, so that epoxy resin
The performances such as toughness, intensity and heat resistance obtained comprehensive raising；Compared with traditional epoxy curing agent, the present invention is not only
Low toxicity or nontoxic is selected in raw material, and the product synthesized is also to be safe from harm, do to human health for non-toxic product
It has arrived environmentally protective.Each step reaction used catalyst system simple and stable, and be commercial product, it is cheap and easy to get, need not after
Separation.Reaction condition is mild, technical process gradual change, and the first step after the reaction was completed, directly feeds intake and carries out second step reaction, be not necessarily to
Filter and purification, it is easy to accomplish industrialization.
Specific embodiment
Below by specific embodiment narration product of the present invention and preparation method thereof.Embodiment is interpreted as illustrating
Property, the range being not intended to limit the present invention.For a person skilled in the art, without departing substantially from spirit and scope of the present invention
Under the premise of, protection scope of the present invention is belonged to the various changes of material component and dosage progress in these embodiments.
Embodiment 1
It is poly- that 20 parts of 1,6 hexamethylene diamine, 62 parts of dimethyl carbonate, 0.05 part of sodium methoxide, 5 parts of methanol and Amino End Group are weighed by mass fraction
138 parts of ether D400,3h is reacted at 70 DEG C of normal pressure, then increases the temperature to 88 DEG C, rectifying goes out to react the methanol generated, rectifying
Top end temperature is 63 DEG C, and rectifying object reaches theoretical amount after 5h, deviates from remaining carbonic acid in the case where vacuum degree is -0.07MPa at this time
Then dimethyl ester is added amine terminated polyether D400 condensation, carries out abjection first under 120 DEG C of reaction temperature, vacuum degree -0.097MPa
Alcohol, methanol stops reaction after reaching theoretical value after 2h, obtains light yellow viscous liquid non-isocyanate urea groups epoxy hardener.It is logical
Detection is crossed, the yield of product is 90%, measures number-average molecular weight 1250.
Embodiment 2
It is poly- that 13 parts of 1,4 butanediamine, 80 parts of dimethyl carbonate, 0.2 part of sodium methoxide, 10 parts of methanol and Amino End Group are weighed by mass fraction
68 parts of ether D230,3h is reacted at 70 DEG C of normal pressure, then increases the temperature to 88 DEG C, rectifying goes out to react the methanol generated, rectifying column
Tip temperature is 63 DEG C, and rectifying object reaches theoretical amount after 5h, deviates from remaining carbonic acid two in the case where vacuum degree is -0.07MPa at this time
Then methyl esters is added amine terminated polyether D400 condensation, carries out abjection first under 120 DEG C of reaction temperature, vacuum degree -0.097MPa
Alcohol, methanol stops reaction after reaching theoretical value after 2h, obtains light yellow viscous liquid non-isocyanate urea groups epoxy hardener.It is logical
Detection is crossed, the yield of product is 95%, measures number-average molecular weight 850.
Embodiment 3
32 parts of 1,6 hexamethylene diamine, 148 parts of dimethyl carbonate, 0.5 part of sodium methoxide, 20 parts of methanol and Amino End Group are weighed by mass fraction
128 parts of polyethers D230,3h is reacted at 70 DEG C of normal pressure, then increases the temperature to 88 DEG C, rectifying, which goes out, reacts the methanol generated, essence
Fractional distillation column tip temperature is 63 DEG C, and rectifying object reaches theoretical amount after 5h, deviates from remaining carbon in the case where vacuum degree is -0.07MPa at this time
Then dimethyl phthalate is added amine terminated polyether D400 condensation, is deviate under 120 DEG C of reaction temperature, vacuum degree -0.097MPa
Methanol, methanol stops reaction after reaching theoretical value after 2h, obtains light yellow viscous liquid non-isocyanate urea groups epoxy hardener.
By detection, the yield of product is 96%, measures number-average molecular weight 930.
Embodiment 4
60 parts of non-isocyanate urea groups epoxy hardener, the bisphenol A epoxide resin E44 that embodiment 1 obtains are weighed by mass fraction
26 parts, the non-isocyanate urea groups epoxy hardener and epoxy resin E44 that weigh up are put into container, in high-speed stirred 0.5h,
Then mixture is poured into grinding tool, and is put into 50 DEG C of curing ovens, take the epoxy resin being cured after 3h.Pass through detection point
Analysis, obtained epoxy resin cured product, bending strength 130MPa, stretch is 16MPa by force, elongation at break 200%, and to it
Antiseptic property is detected: salt-fog resistant time 4500h, after being fully cured after energy 33% hydrochloric acid 72h, the aqueous solution of resistance to 3%NaCl 168h
It is without exception, it is without exception after the aqueous solution of resistance to 5%NaOH 168h.
Embodiment 5
76 parts of non-isocyanate urea groups epoxy hardener, the bisphenol F epoxy resin 6458 that embodiment 1 obtains are weighed by mass fraction
40 parts, the non-isocyanate urea groups epoxy hardener and bisphenol F epoxy resin 6458 that weigh up are put into container, in high-speed stirring
0.5h is mixed, then mixture is poured into grinding tool, and is put into 50 DEG C of curing ovens, takes the epoxy resin being cured after 2h.It is logical
Detection and analysis are crossed, obtained epoxy resin cured product, bending strength 150MPa, stretch is 20MPa by force, and elongation at break is
140%, and its antiseptic property is detected: salt-fog resistant time 4800h, 33% hydrochloric acid 78h of energy, the water of resistance to 3%NaCl after being fully cured
It is without exception after solution 168h, it is without exception after the aqueous solution of resistance to 5%NaOH 168h.
Embodiment 6
83 parts of non-isocyanate urea groups epoxy hardener, the glycidol ether 662 27 that embodiment 1 obtains are weighed by mass fraction
Part, the non-isocyanate urea groups epoxy hardener and bisphenol F epoxy resin 6458 that weigh up are put into container, in high-speed stirred
Then 0.5h pours into mixture in grinding tool, and be put into 50 DEG C of curing ovens, takes the epoxy resin being cured after 1h.Pass through
It tests and analyzes, obtained epoxy resin cured product, bending strength 100MPa, stretch is 12MPa by force, elongation at break 260%,
And its antiseptic property is detected: salt-fog resistant time 3500h, 33% hydrochloric acid 60h of energy, the aqueous solution of resistance to 3%NaCl after being fully cured
It is without exception after 168h, it is without exception after the aqueous solution of resistance to 5%NaOH 168h.
Claims (6)
1. a kind of non-isocyanate urea groups epoxy hardener, it is characterised in that: the non-isocyanate urea groups epoxy hardener
Formula composition includes dialkyl carbonate, diamine compounds and Amino End Group polymer, chemical formula are as follows:
In formula: R2Represent C1 ~ C18 fatty group or alicyclic group or aromatic series base；
R3For polyether structure or alkylen structures；
The non-isocyanate urea groups epoxy hardener is by dialkyl carbonate and diamine compounds according to mol ratio 1:
10 ~ 10:1, synthesis of alkyl diamino-methyl formate；Again by alkyl diamino-methyl formate and Amino End Group polymer according to mole matching
Than being synthesized for 0.5:8 ~ 1:10.
2. a kind of non-isocyanate urea groups epoxy hardener according to claim 1, it is characterised in that: the dialkyl carbonate
Any one or more in base ester, preferably dimethyl carbonate, diethyl carbonate and dipropyl carbonate.
3. a kind of non-isocyanate urea groups epoxy hardener according to claim 1, it is characterised in that: the Diamines
Close object, preferably any one or more of ethylenediamine, 1,2- propane diamine, 1,3- propane diamine, Putriscine, 1,6- hexamethylene diamine.
4. a kind of non-isocyanate urea groups epoxy hardener according to claim 1, it is characterised in that: the Amino End Group is poly-
Close the one or more of object preferred D230, D400, D800.
5. a kind of non-isocyanate urea groups epoxy hardener according to claim 1, it is characterised in that: the non-isocyanic acid
Ester urea groups epoxy hardener the preparation method is as follows:
(1) diamine compounds, dialkyl carbonate, catalysis the synthesis of alkyl diamino-methyl formate: are weighed by mass fraction
Agent A.
6. reacting 1 ~ 8h at 60 ~ 100 DEG C of normal pressure, rectifying, which goes out, reacts the alkylol generated, and rectifying column tip temperature is 60 ~ 80
DEG C, 90 DEG C are then increased the temperature to, deviates from remaining dialkyl carbonate, reaction equation in the case where vacuum degree is -0.07MPa
It is as follows:
(1)
In formula (1): R1Represent the fatty group or alicyclic group or aromatic series base of C1 ~ C8；
R2Represent C1 ~ C18 fatty group or alicyclic group or aromatic series base；
The dosage of the catalyst A is 0.001 ~ 5%；
The catalyst A is basic catalyst, comprising: the oxide of alkali metal and alkaline-earth metal, simple substance, hydride, alcoholates
Or any one in organic base；
(2) synthesis of non-isocyanate urea groups epoxy hardener: under the action of catalyst B, alkyl diamino-methyl formate with
Amine terminated polyether condensation, carries out abjection alkylol, alkyl after 1 ~ 10h under 80 ~ 200 DEG C of reaction temperature, vacuum degree -0.097MPa
Alcohol stops reaction after reaching theoretical value, obtains light yellow viscous liquid non-isocyanate urea groups epoxy hardener, reactional equation
Formula is as follows:
(2)
In formula (2):
R1 represents the fatty group or alicyclic group or aromatic series base of C1 ~ C8；
R2 represents C1 ~ C18 fatty group or alicyclic group or aromatic series base；
R3 is polyether structure or alkylen structures；
The catalyst B is tin catalyst, titanium class catalyst, and dosage is 0.001 ~ 5%.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811103436.8A CN109467692A (en) | 2018-09-20 | 2018-09-20 | A kind of non-isocyanate urea groups epoxy hardener |
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| CN201811103436.8A CN109467692A (en) | 2018-09-20 | 2018-09-20 | A kind of non-isocyanate urea groups epoxy hardener |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1501366A (en) * | 1975-03-06 | 1978-02-15 | Texaco Development Corp | Polyether urea epoxy curing agent |
| US4562241A (en) * | 1984-10-04 | 1985-12-31 | Ciba-Geigy Corporation | Diurethane diureas and the use thereof |
| US20070179257A1 (en) * | 2006-02-01 | 2007-08-02 | Schile Richard D | Epoxy hardener systems based on aminomethylene-ethyleneureas |
| CN101348561A (en) * | 2008-08-01 | 2009-01-21 | 中国林业科学研究院林产化学工业研究所 | Preparation of amine terminated polyether aqueous epoxy hardener |
-
2018
- 2018-09-20 CN CN201811103436.8A patent/CN109467692A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1501366A (en) * | 1975-03-06 | 1978-02-15 | Texaco Development Corp | Polyether urea epoxy curing agent |
| US4562241A (en) * | 1984-10-04 | 1985-12-31 | Ciba-Geigy Corporation | Diurethane diureas and the use thereof |
| US20070179257A1 (en) * | 2006-02-01 | 2007-08-02 | Schile Richard D | Epoxy hardener systems based on aminomethylene-ethyleneureas |
| CN101348561A (en) * | 2008-08-01 | 2009-01-21 | 中国林业科学研究院林产化学工业研究所 | Preparation of amine terminated polyether aqueous epoxy hardener |
Non-Patent Citations (1)
| Title |
|---|
| SHUANG MA ET AL.: ""Catalysts for Isocyanate-Free Polyurea Synthesis Mechanism and Application"", 《ACS CATALYSIS》 * |
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