CN103764712B - Liquid curing-agent and surfactant - Google Patents
Liquid curing-agent and surfactant Download PDFInfo
- Publication number
- CN103764712B CN103764712B CN201280041013.2A CN201280041013A CN103764712B CN 103764712 B CN103764712 B CN 103764712B CN 201280041013 A CN201280041013 A CN 201280041013A CN 103764712 B CN103764712 B CN 103764712B
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- Prior art keywords
- alkyl
- liquid
- hydroxylation
- polyamine
- phenol
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Classifications
-
- 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
- C08G59/50—Amines
-
- 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
- C08G59/50—Amines
- C08G59/5006—Amines aliphatic
- C08G59/5013—Amines aliphatic containing more than seven carbon atoms, e.g. fatty amines
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
Abstract
The invention discloses a kind of liquid as curing agent and/or surface active cpd, it includes the alkyl polyamine (A) of stoichiometry and the phenol (B) of substitution, the wherein R in alkyl polyamine (A) preferably represents linear or branched C1‑C24Alkyl or alkylaryl chain, and in the phenol (B) wherein replaced, X and Y can have several meanings；B is most preferably catechol or salicylic acid.
Description
Introduction
It is common in numerous applications by fatty amine and the fatty amine carboxylate of acetic acid production, such as aliphatic amine-acetic acid salt
Surface active cpd.However, a problem of this kind of compound is, they at room temperature and usually up to about 45 DEG C or
It is solid and not pourable product at higher temperature, the problem of which results in processing.Moreover, because consider health side
Face, the processing of hard fat amine carboxylate need using mask and vest come protect oneself with resist particle, dust and
Steam.
Patent WO2010/146030 describes a kind of excellent (elegant) liquid composition, wherein fatty (poly-) amine and
Carboxylic acid, preferably acetic acid or propionic acid and water combine.Obtained mixture is stable within some time.Due to the combination
Object contains water, the product economically with it is technical due to it is not always desired.
Therefore, still having for more highly enriched, not aqueous (solvent), stable liquid aliphatic (poly-) amine composition needs
It asks.It is an object of the invention to prepare to meet the product of above-mentioned standard.
Fatty (poly-) amine is widely used as the curing agent of epoxy resin based coating systems.Although the carboxylic acid of known low content such as water
Poplar acid, can accelerate and/or optimize curing reaction, but without report its with higher concentration at room temperature be used as curing agent.This
Another purpose of invention is to prepare curing agent, such as containing epoxy resin product based on fat (poly-) amine and carboxylic acid.
Invention content
Applicant is surprisingly it has been found that by the substituted phenol of stoichiometry, particularly hydroxybenzoic acid
After (hydroxybenzoic acid) such as salicylic acid mixing, fatty (poly-) amine can be liquefied.Gained mixture is even at about 0 DEG C
At a temperature of, showing is stable in a long time and is in a liquid state.The product is very soluble in water, and typically high hair
Bubble.According to concentration, foam can be stablized a few days.
This is used as curing agent and/or the liquid of surface-active compositions includes stoichiometry：
Alkyl polyamine (alkylated polyamine) with formula (A)
With the substituted phenol with formula (B)
Preferably, the R group in the alkyl polyamine (A) represents the linear or branched C of Integer n=0 to 101-C24Alkane
Base or alkylaryl chain.Amino in polyamine (A) passes through linear alkyl ((CH2)m), branched-alkyl ((CH2)m), alkylaryl
((CH2)m(aryl)), poly- (aryl), alkylene (alkylene) or poly- (alkylene) connection.
In preferred embodiments, the amino passes through acrylic ((CH2)3) connection, and alkyl R is dodecyl chain.
Dialkyl amine (bisalkylated amines) (C) has with formula R ' NHR ", wherein R ' and R " representative
Saturation, undersaturated linear and/or branched C6-C24Bis- (fatty alkyl) amine of alkyl chain or its mixture, dialkyl amine (C)
Also it can be liquefied after being mixed with substituted phenol (B).
In all cases, the substituted phenol (B) is by X=COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl,
Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO) and Y=H, COOH, carboxylate, OH, NH2、NO2、 SO3H, ester, Cl,
Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO) composition.
In preferred embodiments, the substituted phenol (B) is catechol or salicylic acid.
In addition, after fat (poly-) amine of applied chemistry metering ratio and the phenol of substitution, epoxy resin-matrix system etc. can obtain
To good curing.The excellent of the phenol product of fatty (poly-) amine-substituted will be advocated in the independent patent parallel with this patent
Curing properties more.
In addition, it has been found that i.e. pour-point depressant (pour point depressant), solvent and bulking agent
(compatibliser) it can help to more easily process starting material, but fat (poly-) amine composition for keeping reaction
Property it is certainly not necessary.
In addition to fatty (poly-) amine, it is found by the applicant that fatty alkyl secondary amine, such as the TYPICAL DECOMPOSITION product two of octadecylamine
(octadecyl) amine, can be liquefied (liquified) after being mixed with substituted phenol.
It will be apparent to one skilled in the art that the present invention can be extended to containing monomeric form on a large scale
Or primary, secondary, the tertiary amine of the compound of polymerized form.Compound below is formed usually as the by-product in amine production.
Detailed description of the invention
Fatty (poly-) amine, such as exist by the commercially available alkyl base diamines such as Duomeen, Dinoramax of trade name
It is solid at room temperature.Appropriate processing usually occur over just heat the product after.It can decompose at high temperature, it is usually adjoint
The release of ammonia.Applicant encounters these problems in practice, and is studied to avoid these problems.
The neutralization of fatty amine, which is widely used in optimization processing and (temporarily), reduces the nucleophilic property of amine degree of functionality.Usual carboxylic acid
It is used for this purpose.Substituted phenol also can to amine transmit proton, but mainly basic research (see, for example,
J.Phys.Chem.B, 2008,112 (25), 7748-7759) in inquire into.US 2703765 has claimed taking for a small amount of (catalytic amount)
The benzoic acid in generation such as salicylic acid, can be used as the curing agent of both epoxy-urea formaldehyde and amine-aldehyde resins.However, never it is disclosed this
Stabilizer of a little acid as fatty (poly-) amine.
It has been found that the phenol such as salicylic acid of substitution, it, can be with shape when with higher or lower stoichiometric ratio mixing
Into the liquid with fatty (poly-) amine such as stabilization of cocoyl propane diamine (cocopropylenediamine).FT-IR spectrum
Researches show that going out, even if after being stored for a long time at 60 DEG C, there is not the formation of amide, i.e. typical case between carboxylic acid and amine yet
Reaction.
This superior stability is considered as to be originated from through propane diamine degree of functionality,
And/or the substituted phenol, such as
And the six of stabilization ring-like hydrogen bond (the six-ring type of formed with intermolecular proton exchange
Hydrogen bond) product.
Invention relates further specifically to the liquid as curing agent and/or surface-active compositions, include stoichiometry：
Alkyl polyamine with formula (A)
With the substituted phenol with formula (B)
Preferably, the R in the alkyl polyamine (A) represents linear or branched C1-C24Alkyl or alkylaryl chain, it is more excellent
Select R=C6-C18Linear alkyl chain, particularly R=C8-C14Linear alkyl chain.
Described in the polyamine of formula (A), n=0 to 10.
Amino in polyamine (A) preferably passes through linear alkyl ((CH2)m), branched-alkyl ((CH2)m), alkylaryl
((CH2)m(aryl)), poly- (aryl), alkylene or poly- (alkylene), more preferably pass through the linear alkyl of m=1 to 10
((CH2)m), conveniently by acrylic ((CH2)3) connection.
In the preferred embodiment of this composition, the alkyl polyamine (A) is dodecyl propylene diamine or alkane
Base diallyl triamine.
In the substituted phenol (B), X and Y preferably have following meanings：
X=COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO)；
Y=H, COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde
(CHO),
More preferable X=COOH, carboxylate or OH and Y=H, COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl,
Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO).
In preferred embodiments, the substituted phenol (B) be catechol or salicylic acid, more preferable salicylic acid.
It is according to the present invention as curing agent and/or surface-active compositions by alkyl polyamine (A) and replace
In the liquid of phenol (B) composition, the molar ratio of A and B are preferably 0.8：1.2, more preferable 1.2：0.8, particularly 1：1.
The suitable embodiment of the composition of the present invention is, as curing agent and/or surface-active compositions by 50-99
The liquid of the dodecyl propylene diamine of weight % and the salicylic acid composition of 1-50 weight %.
Preferably, this composition contains the dodecyl propylene diamine of 60-70 weight % and 30-40 weight %
Salicylic acid.
In the present compositions, the substituted phenol (B) can at least partly hydroxylated thiophene, hydroxylation pyridine, hydroxylation pyrrole
The polycyclic hydrocarbon for coughing up, being hydroxylated furans, hydroxylation polycyclic hydrocarbon or hydroxylation substitution is replaced；The hydroxylation thiophene, hydroxylation pyridine, hydroxylation pyrrole
Carboxylic acid or carboxylate groups can be further included by coughing up, be hydroxylated the polycyclic hydrocarbon of furans, hydroxylation polycyclic hydrocarbon or hydroxylation substitution.
The invention further relates to liquid composition, comprising：
Dialkyl amine (C) and
Substituted phenol (B)
The dialkyl amine (C) is preferably with saturation, undersaturated linear and/or branched C6-C24Pair of alkyl chain
(fatty alkyl) amine or its mixture；More preferably carry C14-C20Bis- (fatty alkyl) amine of saturated linear alkyl chain.
In the substituted phenol (B), X and Y preferably have following meanings：
X=COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO)；
Y=H, COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde
(CHO),
More preferable X=COOH, carboxylate or OH and Y=H, COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl, Br,
F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO).
In preferred embodiments, the substituted phenol (B) be catechol or salicylic acid, more preferable salicylic acid.
According to the present invention, liquid is suitably by dialkyl amine (C) and the phenol (B) of substitution with 0.6：1.4 mole
Than more specifically with 1.4：0.6 molar ratio, particularly with 1：1 molar ratio composition.
In the present compositions, the substituted phenol (B) can at least partly hydroxylated thiophene, hydroxylation pyridine, hydroxylation pyrrole
The polycyclic hydrocarbon for coughing up, being hydroxylated furans, hydroxylation polycyclic hydrocarbon or hydroxylation substitution is replaced, the hydroxylation thiophene, hydroxylation pyridine, hydroxylation pyrrole
Carboxylic acid or carboxylate groups can be further included by coughing up, be hydroxylated the polycyclic hydrocarbon of furans, hydroxylation polycyclic hydrocarbon or hydroxylation substitution.
Embodiment：
The present invention will be illustrated by several embodiments, but the range being not intended to be limiting of the invention.It will be to this field
It is obvious to the skilled person that without departing from the spirit and scope, many modifications and variations can be made.
By cocoyl propane diamine (Duomeen CD- Akzo Nobels surface chemistry (Akzo Nobel Surface
Chemistry)) melt at 40 DEG C.50 grams of Duomeen CD are transferred in the glass beaker equipped with magnetic stirring bar, with
After be slowly added to 27 grams of salicylic acids (1:1 molar ratio).Lasting stirring is until obtaining limpid pale yellow solution.By gained mixture
It assigns in several glass flasks.The flask is stored at least one week at 4 DEG C, 20 DEG C and 40 DEG C.Under all conditions, liquid
Product keeps optical stabilization.
In another experiment, 50 grams of Duomeen CD are melted and is transferred to the glass beaker equipped with magnetic stirring bar
In.Then slowly (with 1:1 molar ratio) 21 grams of catechols (99%, Acros Organics) are added in, while lasting stirring is mixed
Close object.Limpid yellow solution is finally obtained, is carried out several storage tests.In addition to (solidification point is about 8 for solidification at 4 DEG C
DEG C) situation, in each case product all keep stable.
In addition, by 65 grams of third triamines of cocoyl (Triameen C- Akzo Nobels surface chemistry) and 35 grams of salicylic acids
It is sufficiently mixed.Stable muddiness (hazy) liquid is obtained, and it keeps stable for a long time at room temperature.
In another experiment, by 65 grams of tallow diallyl triamines (tallowdipropylene triamine)
(Triameen YT- Akzo Nobel's surface chemistries melt 15-25 DEG C of range) merges with 35 grams of salicylic acids.Fully mixed
After conjunction, liquid keeps muddy.Mixture is shown keeps more weeks to stablize at 4 DEG C.
In addition, 40 grams of bis- (octadecyl) amine (are decomposed by octadecylamine and obtained, average molecular weight 540g/mol melts
Change point 55 DEG C) and 10 grams of salicylic acids (with 1:1 molar ratio) it is sufficiently mixed.It obtains troubled liquor and it keeps steady at room temperature
It is fixed.
Claims (29)
1. the liquid as curing agent and/or surface-active compositions, includes stoichiometry：
Alkyl polyamine with formula (A)
With the substituted phenol with formula (B)
R in the formula (A) of wherein described alkyl polyamine represents linear or branched C1-C24Alkyl or alkylaryl chain,
Wherein n=0-10, and
Wherein in the substituted phenol (B)：
X=COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO)；
Y=H, COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO),
Condition is when X is alkyl, and Y is not H,
The ring-like hydrogen bond product of stable six wherein can be formed by propane diamine degree of functionality and/or the substituted phenol.
2. liquid as described in claim 1, wherein R=C6-C18Linear alkyl chain.
3. liquid as described in claim 1, wherein R=C8-C14Linear alkyl chain.
4. the amino in liquid as described in claim 1, wherein polyamine (A) passes through linear alkyl, branched-alkyl, alkyl virtue
Base, poly- (aryl), alkylene or poly- (alkylene) connection.
5. the amino in liquid as described in claim 1, wherein polyamine (A) is connected by the linear alkyl of m=1-10.
6. the amino in liquid as described in claim 1, wherein polyamine (A) is connected by acrylic.
7. liquid as described in claim 1, wherein the alkyl polyamine (A) is dodecyl propylene diamine.
8. liquid as described in claim 1, wherein the alkyl polyamine (A) is alkyl diallyl triamine.
9. liquid as described in claim 1, wherein the alkyl polyamine is the corresponding polymer of formula (A).
10. liquid as described in claim 1, wherein X=COOH, carboxylate or OH and Y=H, COOH, carboxylate, OH,
NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO).
11. liquid as described in claim 1, wherein the substituted phenol (B) is catechol or salicylic acid.
12. liquid as claimed in claim 11, wherein the substituted phenol (B) is salicylic acid.
13. liquid as described in claim 1 is used as curing agent and/or surface active cpd, and by alkyl polyamine
(A) and the phenol (B) of substitution composition, wherein A are 0.8 to the molar ratio of B:1.2.
14. liquid as described in claim 1 is made of the phenol (B) of alkyl polyamine (A) and substitution, wherein A is to B's
Molar ratio is 1.2:0.8.
15. liquid as described in claim 1 is made of the phenol (B) of alkyl polyamine (A) and substitution, wherein A is to B's
Molar ratio is 1:1.
16. the liquid as curing agent and/or surface-active compositions, by the dodecyl acrylic two of 50-99 weight %
The salicylic acid of amine and 1-50 weight % form.
17. liquid as claimed in claim 16, by dodecyl propylene diamine and the 30-40 weight of 60-70 weight %
Measure the salicylic acid composition of %.
18. liquid as described in claim 1, wherein at least partly hydroxylated thiophene of the substituted phenol (B), hydroxylation pyrrole
Pyridine, hydroxylation pyrroles, hydroxylation furans or hydroxylation polycyclic hydrocarbon are replaced.
19. liquid as claimed in claim 18, wherein the hydroxylation thiophene, hydroxylation pyridine, hydroxylation pyrroles, hydroxylation furans or hydroxyl
Change polycyclic hydrocarbon and further include carboxylic acid or carboxylate groups.
20. liquid composition, it includes：
Dialkyl amine (C) with formula R ' NHR " and
Substituted phenol (B)
Wherein described dialkyl amine (C) is with saturation, undersaturated linear and/or branched C6-C24Bis- (fat of alkyl chain
Alkyl) amine or its mixture, and
Wherein in the substituted phenol (B)：
X=COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO)；And
Y=H, COOH, carboxylate, OH, NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO)；
Condition is when X is alkyl, and Y is not H,
The ring-like hydrogen bond product of stable six wherein can be formed by the substituted phenol.
21. liquid composition as claimed in claim 20, wherein the dialkyl amine (C) is with C14-C20Saturated linear
Bis- (fatty alkyl) amine of alkyl chain.
22. liquid composition as claimed in claim 20, wherein X=COOH, carboxylate or OH and Y=H, COOH, carboxylic acid
Salt, OH, NH2、NO2、SO3H, ester, Cl, Br, F, I, alkyl, alkenyl, ether, ketone or aldehyde (CHO).
23. liquid composition as claimed in claim 20, wherein the substituted phenol (B) is catechol or salicylic acid.
24. liquid composition as claimed in claim 23, wherein the substituted phenol (B) is salicylic acid.
25. liquid composition as claimed in claim 20, by dialkyl amine (C) and the phenol (B) of substitution with 0.6:1.4
Molar ratio composition.
26. liquid composition as claimed in claim 20, by dialkyl amine (C) and the phenol (B) of substitution with 1.4:0.6
Molar ratio composition.
27. liquid composition as claimed in claim 20 is made of the phenol (B) of dialkyl amine (C) and substitution, wherein
C is 1 to the molar ratio of B:1.
28. liquid composition as claimed in claim 20, wherein at least partly hydroxylated thiophene of the substituted phenol (B),
Hydroxylation pyridine, hydroxylation pyrroles, hydroxylation furans or hydroxylation polycyclic hydrocarbon are replaced.
29. liquid composition as claimed in claim 28, wherein the hydroxylation thiophene, hydroxylation pyridine, hydroxylation pyrroles, hydroxylation furan
It mutters or is hydroxylated polycyclic hydrocarbon and further include carboxylic acid or carboxylate groups.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1038883 | 2011-06-23 | ||
| NL1038883A NL1038883C2 (en) | 2011-06-23 | 2011-06-23 | Novel liquid curing agents and surfactants. |
| PCT/NL2012/000040 WO2012177121A1 (en) | 2011-06-23 | 2012-06-25 | Novel liquid curing agents and surfactants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103764712A CN103764712A (en) | 2014-04-30 |
| CN103764712B true CN103764712B (en) | 2018-06-22 |
Family
ID=46514747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280041013.2A Expired - Fee Related CN103764712B (en) | 2011-06-23 | 2012-06-25 | Liquid curing-agent and surfactant |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP2723795A1 (en) |
| CN (1) | CN103764712B (en) |
| NL (2) | NL1038883C2 (en) |
| WO (1) | WO2012177121A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI625343B (en) * | 2013-03-28 | 2018-06-01 | 彼 布萊恩私人有限公司 | Curing agent for epoxy resins |
| US20190256734A1 (en) | 2016-06-29 | 2019-08-22 | Holland Novochem Technical Coatings B.V. | Adhesion promoter for coatings on metal surfaces |
| KR102283811B1 (en) | 2016-09-28 | 2021-07-30 | 코오롱인더스트리 주식회사 | Quinone-type curing composition and additive composition using the same |
| WO2019138059A1 (en) | 2018-01-11 | 2019-07-18 | Holland Novochem Technical Coatings B.V. | Curing agent and coating composition |
| EP3620494A1 (en) | 2018-09-06 | 2020-03-11 | Holland Novochem Technical Coatings B.V. | Rheology modifier and compatibilizer |
| WO2020221916A2 (en) | 2019-05-01 | 2020-11-05 | Novochem Green Additives B.V. | Eutectic composition |
| WO2020221917A1 (en) | 2019-05-01 | 2020-11-05 | Novochem Green Additives B.V. | Eutectic composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3366600A (en) * | 1964-06-02 | 1968-01-30 | Grace W R & Co | Process for preparing amine-phenol curing agent epoxy resin compositions |
| US3694409A (en) * | 1968-05-08 | 1972-09-26 | Armour Ind Chem Co | Epoxy resin cured with a fatty tetraamine |
| US3853812A (en) * | 1972-01-07 | 1974-12-10 | Schering Ag | Mixed amine-phenol hardeners for epoxy resins |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2703765A (en) | 1953-01-15 | 1955-03-08 | Du Pont | Salicylic acid cured coating composition comprising an epoxy polyhydroxy polyether resin and an amine-aldehyde resin |
| DE2951603A1 (en) * | 1979-12-21 | 1981-07-02 | Chemische Werke Hüls AG, 4370 Marl | Room temp. curable epoxy resin compsns. - contg. mixt. of prim. and sec. alkylene di:amine(s) as curing agent |
| US8492572B2 (en) | 2009-06-18 | 2013-07-23 | Akzo Nobel Chemicals International B.V. | Liquid fatty amine carboxylate salt composition |
-
2011
- 2011-06-23 NL NL1038883A patent/NL1038883C2/en not_active IP Right Cessation
-
2012
- 2012-06-25 WO PCT/NL2012/000040 patent/WO2012177121A1/en unknown
- 2012-06-25 EP EP12735663.2A patent/EP2723795A1/en not_active Withdrawn
- 2012-06-25 NL NL1039698A patent/NL1039698C2/en not_active IP Right Cessation
- 2012-06-25 CN CN201280041013.2A patent/CN103764712B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3366600A (en) * | 1964-06-02 | 1968-01-30 | Grace W R & Co | Process for preparing amine-phenol curing agent epoxy resin compositions |
| US3694409A (en) * | 1968-05-08 | 1972-09-26 | Armour Ind Chem Co | Epoxy resin cured with a fatty tetraamine |
| US3853812A (en) * | 1972-01-07 | 1974-12-10 | Schering Ag | Mixed amine-phenol hardeners for epoxy resins |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103764712A (en) | 2014-04-30 |
| EP2723795A1 (en) | 2014-04-30 |
| NL1039698A (en) | 2013-01-02 |
| WO2012177121A1 (en) | 2012-12-27 |
| NL1038883C2 (en) | 2013-01-02 |
| NL1039698C2 (en) | 2013-02-19 |
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