NL1039698C2 - Novel liquid curing agents and surfactants. - Google Patents

Novel liquid curing agents and surfactants. Download PDF

Info

Publication number
NL1039698C2
NL1039698C2 NL1039698A NL1039698A NL1039698C2 NL 1039698 C2 NL1039698 C2 NL 1039698C2 NL 1039698 A NL1039698 A NL 1039698A NL 1039698 A NL1039698 A NL 1039698A NL 1039698 C2 NL1039698 C2 NL 1039698C2
Authority
NL
Netherlands
Prior art keywords
hydroxylated
composition
alkyl
substituted phenol
carboxylate
Prior art date
Application number
NL1039698A
Other languages
Dutch (nl)
Other versions
NL1039698A (en
Inventor
Alexander Maslow
Alexander Schoolen
Erik Alexander Bijpost
Original Assignee
Holland Novochem Technical Coatings B V
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Holland Novochem Technical Coatings B V filed Critical Holland Novochem Technical Coatings B V
Priority to NL1039698A priority Critical patent/NL1039698C2/en
Publication of NL1039698A publication Critical patent/NL1039698A/en
Application granted granted Critical
Publication of NL1039698C2 publication Critical patent/NL1039698C2/en

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

Title: Novel liquid curing agents and surfactants
Introduction
Fatty amine carboxylate salts, such as fatty amine acetate salts, produced from fatty amine and acetic acid, are 5 common surface active compounds used in many applications. However, one problem of this class of compounds is that they are solid, non-pourable products at room temperature and often up to about 45 °C or higher, leading to handling problems. Further, due to health aspects, handling of solid fatty amine 10 carboxylate salts requires the use of protection masks and protective clothes to protect oneself against particles, dust and vapours .
Patent W02010/146030 describes an elegant liquid composition in which fatty (poly)amines, are combined with 15 carboxylic acid, preferably acetic or propionic acid, and water. The resulting mixtures are claimed to be stable over a long period of time. As the compositions contain water, the products are not always desired for both economic and technical reasons .
20 Hence there is still a need for higher concentrated, water (solvent) free, stable, liquid fatty (poly)amine composition. An objective of this invention is to formulate products, meeting the mentioned criteria.
Fatty (poly)amines are widely applied as curing agent for 25 epoxy-based coating systems. Though carboxylic acids, such as salicylic acid, at low amounts are known to accelerate and/or to optimize curing reactions, they have yet not been reported to act as curing agent at higher concentrations at room temperature. Another objective of this invention is to prepare 30 a curing agent, based on fatty (poly)amines and carboxylic acids, for example epoxy-containing products.
1039698 2
Invention:
Applicant has surprisingly found that fatty (poly)amines can be liquefied upon mixing stoichiometric amounts of 5 substituted phenols, in particular hydroxybenzoic acids, such as salicylic acid. The resulting mixtures appeared even to be stable and liquid at temperatures around 0 °C for a long period of time. The products dissolve very easily in water and are usually very high foaming. Depending on the concentration 10 the foams can be stable for several days.
The liquids acting as curing agent and/or surface active composition comprise stoichiometric amount of: • An alkylated polyamine having formula (A)
R. .N NH
L Jn *
.s A
• And a substituted phenol having formula (B)
OH
X
B
20
Preferably the R group in said alkylated polyamine (A) represents a linear or branched Cl - C24 alkyl or alkylaryl chain with integer n = 0 to 10. The amino groups in polyamine (A) are connected via linear alkyl ((CH2)m)/ branched alkyl 25 ( (CH2)m) / alkylaryl ( (CH2)m(aryl) , poly(aryl), alkylene or poly(alkylene) groups .
In a preferred embodiment the amino groups are connected via a propylene group ((CH2)3), whereas the alkyl group R is a dodecyl chain.
3
Bisalkylated amines (C), with the formula R' NHR", wherein R' and R" represent bis(fatty alkyl) amine with saturated, unsaturated, linear and/or branched C6-C24 alkyl chains or mixtures thereof can be liquefied upon admixing with 5 substituted phenol (B) as well.
In all cases, the said substituted phenol (B) consists of X = COOH, carboxylate, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO) and Y = H, COOH, carboxylate, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, 10 alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO).
In a preferred embodiment, the substituted phenol (B) is catechol or salicylic acid.
Moreover, upon applying stoichiometric ratios of fatty 15 (poly)amine and substituted phenols, excellent curing of epoxy-based systems and the like can be obtained. The exceptional curing properties of fatty (poly)amines-substituted phenols products will be claimed in an independent patent parallel to the underlying patent.
20 In addition, Applicant found that i.e. pour point depressants, solvents and compatiblisers, can contribute to easier processing the starting materials, but are definitely not necessary to maintain the properties of the reacted fatty (poly)amine composition.
25 Apart from fatty (poly)amines Applicant found that fatty alkyl secondary amines, such as di(octadecyl)amine, a typical decomposition product of octadecylamine, can be liquefied as well upon mixing with substituted phenols.
It is obvious for those-skilled-in-the arts that the 30 invention can be extended to a wide range of primary, secondary, tertiary amine containing compounds, either in monomeric form or in polymeric form. The latter compounds are commonly formed as by-product in the production of amines.
35 Description:
Fatty (poly)amines, such as alkylpropylenediamines, commercially available under brand names Duomeen, Dinoramax etc, are solid at room temperature. Proper handling usually 4 can only occur upon wanning up the product. At high temperature decomposition can take place, usually with release of ammonia. Applicant encountered these problems in practice and undertook a study to avoid these problems.
5 Neutralization of fatty amines is widely applied to optimize handling and decrease (temporarily) the nucleophilic properties of the amine functionality. Commonly carboxylic acids are used for this purpose. Substituted phenols can transfer a proton to an amine as well, but are mainly explored 10 in fundamental studies (see for example J. Phys. Chem. B, 2008, 112 (25), 7748-7759). US 2703765 claims that small (catalytic) amounts of substituted benzoic acids, such as salicylic acid, can act as curing agent for both epoxy- and amine-aldehyde resins. However, these acids have never been 15 published as stabilizer for fatty (poly)amines.
Applicant found that substituted phenols, such as salicylic acid, can form stable liquids with fatty (poly)amines, such as cocopropylenediamine, when mixed in more or less stoichiometric ratios. FT-IR spectroscopic studies 20 showed that amide formation, a typical reaction between carboxylic acid and amine, does not occur, even after storage at 60 °C for a long period of time.
The exceptional stability is believed to originate from the formation of stable six-ring type of hydrogen bond 25 products via both the propylene diamine functionality,
Fk /H. Fk .hk n nh2 __ nh nh and/or the substituted phenol, for example, 30 5 O o and the accompanying intermolecular exchange of protons.
The present invention more specifically relates to a 5 liquid acting as curing agent and/or surface active composition, comprising a stoichiometric amount of: • An alkylated polyamine having formula (A) FL N NH Nx L Jn *
A
10 • And a substituted phenol having formula (B)
OH
X
B
15 Preferably, R in said alkylated polyamine (A) represents a linear or branched Cl - C24 alkyl or alkylaryl chain, more preferably is R = C6-C18 linear alkyl chain, especially R = C8-C14 linear alkyl chain.
In the polyamine having formula (A) is n = 0 to 10.
20 The amino groups in polyamine (A) are preferably connected via linear alkyl ((CH2)m), branched alkyl ((CH2)m), alkylaryl ( (CH2)m(aryl), poly (aryl), alkylene or poly(alkylene) groups, more preferably via linear alkyl ((CH2)m) with m = 1 to 10, expediently via a propylene group ((CH2)3)- 6
In a preferred embodiment of the present composition is the alkylated polyamine (A) dodecylpropylenediamine, or alkyldipropylenetriamine.
In said substituted phenol (B) have X and Y preferably 5 the following meanings: • X = COOH, carboxylate, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO); • Y = H, COOH, carboxylate, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde 10 (CHO), more preferably X = COOH, carboxylate, or OH and Y = H, COOH, carboxylate, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO).
In a preferred embodiment is said substituted phenol (B) 15 catechol or salicylic acid, more preferably salicylic acid.
In a liquid, according to the invention acting as curing agent and/or surface active compound consisting of alkylated polyamine (A) and substituted phenol (B) is the molar ratio of A to B preferably 0.8 to 1.2, more preferably 1.2 to 0.8, 20 especially 1 to 1.
An expedient embodiment of a composition according to the invention is a liquid acting as curing agent and/or surface active composition consisting of 50 - 99% by weight of dodecylpropylenediamine and 1 - 50% by weight of salicylic 25 acid.
Preferably such a composition contains 60 - 70% by weight of dodecylpropylenediamine and 30 - 40% by weight of salicylic acid.
In the present composition may the substituted phenol (B) 30 at least partially be replaced by a hydroxylated thiophene, hydroxylated pyridine, hydroxylated pyrrole, hydroxylated furan, hydroxylated polycyclic hydrocarbon or hydroxylated substituted polycyclic hydrocarbon; said hydroxylated thiophene, hydroxylated pyridine, hydroxylated pyrrole, 35 hydroxylated furan, hydroxylated polycyclic hydrocarbon or hydroxylated substituted polycyclic hydrocarbon may further comprise a carboxylic acid or carboxylate group.
The invention also relates to a liquid composition, comprising: 7 • Bisalkylated amine (C) and • Substituted phenol (B)
OH
X
XX
B
5
The bisalkylated amine (C) is preferably a bis(fatty alkyl) amine with saturated, unsaturated, linear and/or branched C6-C24 alkyl chains or mixtures thereof; more preferably a bis(fatty alkyl) amine with C14-C20 saturated 10 linear alkyl chains.
In said substituted phenol (B) have X and Y preferably the following meanings: • X = COOH, carboxylate, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO); 15 • Y = H, COOH, carboxylate, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO), more preferably is X = COOH, carboxylate, or OH and Y = H, COOH, carboxylate, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, 20 alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO).
In a preferred embodiment is said substituted phenol (B) catechol or salicylic acid, more preferably salicylic acid.
A liquid, according to the invention, consists expediently of bis(alkylated) amine (C) and substituted phenol 25 (B) in a molar ratio 0.6 to 1.4, more specifically a molar ratio 1.4 to 0.6, especially a molar ratio of C to B of 1 to 1.
In the present composition may the substituted phenol (B) at least partially be replaced by a hydroxylated thiophene, 30 hydroxylated pyridine, hydroxylated pyrrole, hydroxylated furan, hydroxylated polycyclic hydrocarbon or hydroxylated substituted polycyclic hydrocarbon, and may said hydroxylated thiophene, hydroxylated pyridine, hydroxylated pyrrole, hydroxylated furan, hydroxylated polycyclic hydrocarbon or 8 hydroxylated substituted polycyclic hydrocarbon further comprise a carboxylic acid or carboxylate group.
Examples .-5
The invention will be illustrated by a number of examples, but is not intended to limit the scope of the invention. Many modifications and variations can be made without departing from its spirit and scope, as will be 10 apparent to those skilled-in-the-arts.
Cocopropylene diamine (Duomeen CD - Akzo Nobel Surface Chemistry) is molten at 40 °C. 50 grams Duomeen CD is transferred into a glass beaker, equipped with a magnetic stirring bar, followed by slow addition of 27 grams salicylic 15 acid (1:1 molar ratio). Stirring is continued till a clear light yellow solution is obtained. The resulting mixture is divided over a number of glass flasks. The flasks are stored at 4 °C, 20 °C and 40 °C for at least one week. Under all conditions, the liquid product remains stable optically.
20 In another experiment, 50 grams Duomeen CD is molten and transferred into a glass beaker, equipped with a magnetic stirring bar. Then slowly 21 grams catechol (99%, Acros Organics) is added (1:1 molar ratio) whilst continuously stirring the mixture. Finally a clear yellow solution is 25 obtained, which has been subjected to several storage tests.
In each case a stable product remained, except at 4 °C due to solidification (solidification point of approximately 8 °C).
In addition, 65 grams cocopropylene triamine (Triameen C - Akzo Nobel Surface Chemistry) is thoroughly mixed with 35 30 grams salicylic acid. A hazy stable liquid is obtained and remains stable at room temperature over a long period of time.
In another experiment, 65 grams tallowdipropylene triamne (Triameen YT - Akzo Nobel Surface Chemistry, melting range 15-25 °C) is combined with 35 grams salicylic acid. After 35 thoroughly mixing, a hazy liquid remains. The mixture appears to be stable a 4 °C for many weeks.
Moreover, 40 grams Di(octadecyl)amine (obtained by decomposition of octadecylamine, average molecular weight 540 g/mol, melting point 55 °C) and 10 grams salicylic acid (1:1 9 molar ratio) is mixed thoroughly. A hazy liquid is obtained and remains stable at room temperature.
1039698

Claims (32)

1. Vloeistof die werkt als hardingsmiddel en/of oppervlakteactieve samenstelling, die een stoichiometrische hoeveelheid omvat van: • een gealkyleerd polyamine met formule (A), waarin R 5 een lineaire of vertakte C6-C18 alkyl of alkylarylketen voorstelt, het polyamine een mono of di (polyamine) is, de aminogroep driewaardig is, die 0 of 1 actief waterstofatoom bevat, en * 2 waterstofatomen of 1 waterstofatoom en een 10 koolstofbevattende groep voorstelt, FL .N N NL Jn * A 15. en een gesubstitueerd fenol met formule (B), waarin X en Y waterstofatomen of een polaire functionele groep voorstellen, doch waarbij X en Y niet tegelijkertijd een waterstofatoom voorstellen, 20 OH X BA fluid that acts as a curing agent and / or surfactant composition comprising a stoichiometric amount of: an alkylated polyamine of formula (A), wherein R 5 represents a linear or branched C 6 -C 18 alkyl or alkylaryl chain, the polyamine a mono or di (polyamine), the amino group is trivalent, containing 0 or 1 active hydrogen atom, and * representing 2 hydrogen atoms or 1 hydrogen atom and a carbon-containing group, FL .NN NL Jn * A 15. and a substituted phenol of formula (B ), wherein X and Y represent hydrogen atoms or a polar functional group, but where X and Y do not simultaneously represent a hydrogen atom, OH XB 2. Samenstelling volgens conclusie 1, waarbij R = C8-C14 lineaire alkylketen. 25 1039698The composition of claim 1, wherein R = C 8 -C 14 linear alkyl chain. 25 1039698 3. Samenstelling volgens conclusie 1 of 2, waarbij n = 0 tot 10.The composition of claim 1 or 2, wherein n = 0 to 10. 4. Samenstelling volgens één of meer van de conclusies 1-3, 5 waarbij de aminogroepen in polyamine (A) zijn verbonden via lineaire alkyl ((CH2)m), vertakte alkyl ((CH2)m), alkylaryl ( (CH2)m(aryl), poly(aryl), alkyleen of poly(alkyleen) groepen.The composition of any one of claims 1-3, wherein the amino groups in polyamine (A) are linked via linear alkyl ((CH2) m), branched alkyl ((CH2) m), alkylaryl ((CH2) m (aryl), poly (aryl), alkylene or poly (alkylene) groups. 5. Samenstelling volgens één of meer van de conclusies 1-4, 10 waarbij de aminogroepen in polyamine (A) zijn verbonden via lineaire alkyl ( (CH2)m) met m = 1 tot 10.A composition according to any one of claims 1-4, wherein the amino groups in polyamine (A) are connected via linear alkyl ((CH 2) m) with m = 1 to 10. 6. Samenstelling volgens één of meer van de conclusies 1-5, waarbij de aminogroepen in polyamine (A) zijn verbonden via 15 een propyleengroep ((CH2 )3).6. Composition according to one or more of claims 1-5, wherein the amino groups in polyamine (A) are connected via a propylene group ((CH2) 3). 7. Samenstelling volgens één of meer van de conclusies 1-6, waarbij het gealkyleerde polyamine (A) dodecylpropyleendiamine is. 20The composition of any one of claims 1-6, wherein the alkylated polyamine (A) is dodecylpropylene diamine. 20 8. Samenstelling volgens één of meer van de conclusies 1-7, waarbij het gealkyleerde polyamine (A) alkyldipropyleentriamine is.A composition according to any one of claims 1-7, wherein the alkylated polyamine (A) is alkyl dipropylene triamine. 9. Samenstelling volgens één of meer van de conclusies 1-8, waarbij het gealkyleerde polyamine het overeenkomende polymeer van (A) is.The composition of any one of claims 1-8, wherein the alkylated polyamine is the corresponding polymer of (A). 10. Samenstelling volgens één of meer van de conclusies 1-9, 30 waarbij in het gesubstitueerde fenol (B): • X = COOH, carboxylaat, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, keton (COR) of aldehyde (CHO); • Y = H, COOH, carboxylaat, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, keton (COR) of aldehyde 35 (CHO).10. Composition according to any one of claims 1-9, wherein in the substituted phenol (B): X = COOH, carboxylate, OH, NH 2, NO 2, SO 3 H, COOR, Cl, Br, F, I, alkyl , alkenyl, ether, ketone (COR) or aldehyde (CHO); Y = H, COOH, carboxylate, OH, NH 2, NO 2, SO 3 H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO). 11. Samenstelling volgens één of meer van de conclusies 1-10, waarbij X = COOH, carboxylaat, of OH en Y = H, COOH, carboxylaat, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, keton (COR) of aldehyde (CHO).A composition according to any one of claims 1-10, wherein X = COOH, carboxylate, or OH and Y = H, COOH, carboxylate, OH, NH 2, NO 2, SO 3 H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO). 12. Samenstelling volgens één of meer van de conclusies 1-11, 5 waarbij het gesubstitueerde fenol (B) catechol of salicylzuur is.The composition of any one of claims 1 to 11, wherein the substituted phenol (B) is catechol or salicylic acid. 13. Samenstelling volgens één of meer van de conclusies 1-12, waarbij gesubstitueerd fenol (B) salicylzuur is. 10The composition of any one of claims 1 to 12, wherein substituted phenol (B) is salicylic acid. 10 14. Vloeistof volgens één of meer conclusies 1-13, die werkt als hardingsmiddel en/of oppervlakteactieve verbinding, bestaande uit gealkyleerd polyamine (A) en gesubstitueerd fenol (B), waarbij de molverhouding van A tot B 0,8 tot 1,2 15 is.Liquid according to one or more of claims 1-13, which acts as a curing agent and / or surfactant, consisting of alkylated polyamine (A) and substituted phenol (B), wherein the molar ratio of A to B is 0.8 to 1.2 15 is. 15. Vloeistof volgens één of meer van de conclusies 1-14, bestaande uit gealkyleerd polyamine (A) en gesubstitueerd fenol (B) waarbij de molverhouding van A tot B 1,2 tot 0,8 is. 20Liquid according to one or more of claims 1-14, consisting of alkylated polyamine (A) and substituted phenol (B) wherein the molar ratio of A to B is 1.2 to 0.8. 20 16. Vloeistof volgens één of meer van de conclusies 1-15, bestaande uit gealkyleerd polyamine (A) en gesubstitueerd fenol (B) waarbij de molverhouding van A tot B 1 tot 1 is.Liquid according to one or more of claims 1 to 15, consisting of alkylated polyamine (A) and substituted phenol (B) wherein the molar ratio of A to B is 1 to 1. 17. Vloeistof die werkt als hardingsmiddel en/of oppervlakteactieve samenstelling, bestaande uit 50 - 99 gew.% dodecylpropyleendiamine en 1 - 50 gew.% salicylzuur.17. Liquid that acts as a curing agent and / or surfactant composition, consisting of 50 - 99% by weight dodecylpropylenediamine and 1 - 50% by weight salicylic acid. 18. Samenstelling volgens conclusie 17, waarbij het mengsel 60 30 - 70 gew.% dodecylpropyleendiamine en 30 - 40 gew.% salicylzuur bevat.The composition of claim 17, wherein the mixture comprises 60 to 30% by weight of dodecylpropylenediamine and 30 to 40% by weight of salicylic acid. 19. Samenstelling volgens één of meer van de conclusies 1-18, waarbij het gesubstitueerde fenol (B) ten minste gedeeltelijk 35 is vervangen door een gehydroxyleerd thiofeen, gehydroxyleerd pyridine, gehydroxyleerd pyrrool, gehydroxyleerd furan, gehydroxyleerde polycyclische koolwaterstof of gehydroxyleerde gesubstitueerde polycyclische koolwaterstof.19. A composition according to any one of claims 1-18, wherein the substituted phenol (B) is replaced at least in part by a hydroxylated thiophene, hydroxylated pyridine, hydroxylated pyrrole, hydroxylated furan, hydroxylated polycyclic hydrocarbon or hydroxylated substituted polycyclic hydrocarbon. 20. Samenstelling volgens conclusie 19, waarbij het gehydroxyleerde thiofeen, gehydroxyleerde pyridine, gehydroxyleerde pyrrool, gehydroxyleerde furan, gehydroxyleerde polycyclische koolwaterstof of gehydroxyleerde 5 gesubstitueerde polycyclische koolwaterstof voorts een carbonzuur of carboxylaatgroep omvat.20. The composition of claim 19, wherein the hydroxylated thiophene, hydroxylated pyridine, hydroxylated pyrrole, hydroxylated furan, hydroxylated polycyclic hydrocarbon or hydroxylated substituted polycyclic hydrocarbon further comprises a carboxylic acid or carboxylate group. 21. Vloeistofsamenstelling die omvat: • Bisgealkyleerd amine (C) , met formule R' NHR' ' en 10 • Gesubstitueerd fenol (B) OH X B21. Liquid composition comprising: • bis-alkylated amine (C), of formula R 'NHR' 'and • substituted phenol (B) OH X B 22. Samenstelling volgens conclusie 22, waarbij het 15 bisgealkyleerde amine (C) bis(vetalkyl)amine met verzadigde, onverzadigde, lineaire en/of vertakte C6-C24 alkylketens of mengsels daarvan is.22. A composition according to claim 22, wherein the bis-alkylated amine is (C) bis (fatty alkyl) amine with saturated, unsaturated, linear and / or branched C 6 -C 24 alkyl chains or mixtures thereof. 23. Samenstelling volgens conclusie 21-22, waarbij het 20 bisgealkyleerde amine (C) bis(vetalkyl)amine met C14-C20 verzadigde lineaire alkylketens, is.23. A composition according to claims 21-22, wherein the bisalkylated amine is (C) bis (fatty alkyl) amine C14 -C20 saturated linear alkyl chains. 24. Samenstelling volgens één of meer van de conclusies 21-23, waarbij in het gesubstitueerde fenol (B):The composition of any one of claims 21 to 23, wherein in the substituted phenol (B): 25. Samenstelling volgens één of meer van de conclusies 21-24, waarbij X = COOH, carboxylaat, of OH en Y = H, COOH, carboxylaat, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, keton (COR) of aldehyde (CHO).The composition of any one of claims 21 to 24, wherein X = COOH, carboxylate, or OH and Y = H, COOH, carboxylate, OH, NH 2, NO 2, SO 3 H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO). 25. X = COOH, carboxylaat, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, keton (COR) of aldehyde (CHO); • Y = H, COOH, carboxylaat, OH, NH2, N02, S03H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, keton (COR) of aldehyde (CHO). 3025. X = COOH, carboxylate, OH, NH 2, NO 2, SO 3 H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO); Y = H, COOH, carboxylate, OH, NH 2, NO 2, SO 3 H, COOR, Cl, Br, F, I, alkyl, alkenyl, ether, ketone (COR) or aldehyde (CHO). 30 26. Samenstelling volgens één of meer van de conclusies 21-25, waarbij gesubstitueerd fenol (B) catechol of salicylzuur is.The composition of any one of claims 21 to 25, wherein substituted phenol (B) is catechol or salicylic acid. 27. Samenstelling volgens één of meer van de conclusies 21-26, waarbij gesubstitueerd fenol (B) salicylzuur is.The composition of any one of claims 21 to 26, wherein substituted phenol (B) is salicylic acid. 28. Vloeistof volgens één of meer van de conclusies 21-27, bestaande uit bis(gealkyleerd) amine (C) en gesubstitueerd 10 fenol (B) in een molverhouding van 0,6 tot 1,4.28. Liquid according to one or more of claims 21-27, consisting of bis (alkylated) amine (C) and substituted phenol (B) in a molar ratio of 0.6 to 1.4. 29. Vloeistof volgens één of meer van de conclusies 21-28, bestaande uit bis(gealkyleerd) amine en gesubstitueerd fenol (B) in een molverhouding van 1,4 tot 0,6. 15Liquid according to one or more of claims 21 to 28, consisting of bis (alkylated) amine and substituted phenol (B) in a molar ratio of 1.4 to 0.6. 15 30. Vloeistof volgens één of meer van de conclusies 21-29, bestaande uit bis(gealkyleerd) amine (C) en gesubstitueerd fenol (B) waarbij de molverhouding van A tot B 1 tot 1 is.A liquid according to any one of claims 21 to 29, consisting of bis (alkylated) amine (C) and substituted phenol (B) wherein the molar ratio of A to B is 1 to 1. 31. Samenstelling volgens één of meer van de conclusies 21-30, waarbij het gesubstitueerde fenol (B) ten minste gedeeltelijk is vervangen door een gehydroxyleerd thiofeen, gehydroxyleerd pyridine, gehydroxyleerd pyrrool, gehydroxyleerd furan, gehydroxyleerde polycyclische koolwaterstof of gehydroxyleerde 25 gesubstitueerde polycyclische koolwaterstof.31. A composition according to any one of claims 21-30, wherein the substituted phenol (B) is at least partially replaced by a hydroxylated thiophene, hydroxylated pyridine, hydroxylated pyrrole, hydroxylated furan, hydroxylated polycyclic hydrocarbon or hydroxylated substituted polycyclic hydrocarbon. 32. Samenstelling volgens conclusie 31, waarbij het gehydroxyleerde thiofeen, gehydroxyleerde pyridine, gehydroxyleerde pyrrool, gehydroxyleerde furan, 30 gehydroxyleerde polycyclische koolwaterstof of gehydroxyleerde gesubstitueerde polycyclische koolwaterstof voorts een carbonzuur of carboxylaatgroep omvat. 103969832. The composition of claim 31, wherein the hydroxylated thiophene, hydroxylated pyridine, hydroxylated pyrrole, hydroxylated furan, hydroxylated polycyclic hydrocarbon or hydroxylated substituted polycyclic hydrocarbon further comprises a carboxylic acid or carboxylate group. 1039698
NL1039698A 2011-06-23 2012-06-25 Novel liquid curing agents and surfactants. NL1039698C2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NL1039698A NL1039698C2 (en) 2011-06-23 2012-06-25 Novel liquid curing agents and surfactants.

Applications Claiming Priority (4)

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.
NL1039698A NL1039698C2 (en) 2011-06-23 2012-06-25 Novel liquid curing agents and surfactants.
NL1039698 2012-06-25

Publications (2)

Publication Number Publication Date
NL1039698A NL1039698A (en) 2013-01-02
NL1039698C2 true NL1039698C2 (en) 2013-02-19

Family

ID=46514747

Family Applications (2)

Application Number Title Priority Date Filing Date
NL1038883A NL1038883C2 (en) 2011-06-23 2011-06-23 Novel liquid curing agents and surfactants.
NL1039698A NL1039698C2 (en) 2011-06-23 2012-06-25 Novel liquid curing agents and surfactants.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
NL1038883A NL1038883C2 (en) 2011-06-23 2011-06-23 Novel liquid curing agents and surfactants.

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)

* Cited by examiner, † Cited by third party
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
EP3478776A2 (en) 2016-06-29 2019-05-08 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
WO2020221917A1 (en) 2019-05-01 2020-11-05 Novochem Green Additives B.V. Eutectic composition
WO2020221916A2 (en) 2019-05-01 2020-11-05 Novochem Green Additives B.V. Eutectic composition

Family Cites Families (6)

* Cited by examiner, † Cited by third party
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
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
BE793700A (en) * 1972-01-07 1973-07-05 Schering Ag HARDENERS FOR EPOXIDIC RESINS
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
EP2443218B1 (en) 2009-06-18 2013-08-07 Akzo Nobel Chemicals International B.V. Liquid fatty amine carboxylate salt composition

Also Published As

Publication number Publication date
WO2012177121A1 (en) 2012-12-27
NL1038883C2 (en) 2013-01-02
CN103764712B (en) 2018-06-22
CN103764712A (en) 2014-04-30
EP2723795A1 (en) 2014-04-30
NL1039698A (en) 2013-01-02

Similar Documents

Publication Publication Date Title
NL1039698C2 (en) Novel liquid curing agents and surfactants.
RU2622339C2 (en) Systems of n-alkyltiophosphoric acid triamides with solvent and methods of their application in agriculture
HRP20171676T1 (en) Bituminous composition with thermoreversible properties
MX2010004340A (en) Thermally stable compositions and use thereof in drilling fluids.
ES2603610T3 (en) Polyisobutene emulsions, substance and procedure
US7341985B2 (en) 2-Hydroxy-3-alkoxypropyl sulfides, sulfones, and sulfoxides: new surface active agents
JP2014533762A (en) Alkoxylated polyalkylene polyamine
EP3294843B1 (en) Nitrogen-containing anti-agglomerants for preserving the fluidity of fluids containing gas hydrates
CN111492046A (en) Aromatic-based polyetheramine alkoxylates
CN113286780A (en) Process for preparing organic sulfates of amino acid esters
US5672739A (en) Class of three tail surfactants law388
US11174215B2 (en) Method of producing methyl methacrylate or methacrylic acid
NL1039697C2 (en) Novel polymers and polymer compositions.
US6310174B1 (en) Primary alkanolamides
WO2014033967A1 (en) Photo acid generator and its synthetic method
JP2017528586A5 (en)
US3799909A (en) Method of curing epoxy resins using n-aminoalkylphthalamides
NL1038105C2 (en) Heat-resistant, chemical resistant, room temperature curable, solvent-free resin compositions to apply as protective coating.
JP2010241877A (en) Liquid phenol-based curing agent, composition, cured product, and use of the same
KR101776034B1 (en) Polyhydroxylated amine based polymer and method for preparing thereof
JP2006045155A (en) Phosphonium salt preparation for water treatment and method for preventing environmental stress crack
WO2023247445A1 (en) Solution of polyphenols in amine
FR3119395A1 (en) POLYESTERAMINES AND POLYESTERQUATS
US20220177415A1 (en) Quaternary fatty amidoamine detergents
JP2010031067A (en) Polyhydrazone compound and method for producing the same, and anticorrosive agent for metal comprising polyhydrazone compound

Legal Events

Date Code Title Description
MM Lapsed because of non-payment of the annual fee

Effective date: 20200701