NL1039698A - Novel liquid curing agents and surfactants. - Google Patents

Novel liquid curing agents and surfactants. Download PDF

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NL1039698A
NL1039698A NL1039698A NL1039698A NL1039698A NL 1039698 A NL1039698 A NL 1039698A NL 1039698 A NL1039698 A NL 1039698A NL 1039698 A NL1039698 A NL 1039698A NL 1039698 A NL1039698 A NL 1039698A
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hydroxylated
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alkyl
substituted phenol
carboxylate
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NL1039698A
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Alexander Maslow
Alexander Schoolen
Erik Alexander Bijpost
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Holland Novochem Technical Coatings B V
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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
    • C08G59/50—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

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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 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 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 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 .
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 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 a curing agent, based on fatty (poly)amines and carboxylic acids, for example epoxy-containing products.
Invention:
Applicant has surprisingly found that fatty (poly)amines can be liquefied upon mixing stoichiometric amounts of 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 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)
Figure NL1039698AD00031
• And a substituted phenol having formula (B)
Figure NL1039698AD00032
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 ((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.
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 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, 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 (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.
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.
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 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.
Description:
Fatty (poly)amines, such as alkylpropylenediamines, commercially available under brand names Duomeen, Dinoramax etc, are solid at room temperature. Proper handling usually 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.
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 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 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 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 products via both the propylene diamine functionality,
Figure NL1039698AD00051
and/or the substituted phenol, for example,
Figure NL1039698AD00061
and the accompanying intermolecular exchange of protons.
The present invention more specifically relates to a liquid acting as curing agent and/or surface active composition, comprising a stoichiometric amount of: • An alkylated polyamine having formula (A)
Figure NL1039698AD00062
• And a substituted phenol having formula (B)
Figure NL1039698AD00063
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.
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)·
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 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 (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) 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, 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 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) 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, 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: • Bisalkylated amine (C) and • Substituted phenol (B)
Figure NL1039698AD00081
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 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); • 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, 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 (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, 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 hydroxylated substituted polycyclic hydrocarbon further comprise a carboxylic acid or carboxylate group.
Examples .-
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 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 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.
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 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 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 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 molar ratio) is mixed thoroughly. A hazy liquid is obtained and remains stable at room temperature.

Claims (34)

1. Vloeistof die werkt als hardingsmiddel en/of oppervlakteactieve samenstelling, die een stoichiometrische hoeveelheid omvat van: • een gealkyleerd polyamine met formule (A)A liquid that acts as a curing agent and / or surfactant composition, comprising a stoichiometric amount of: an alkylated polyamine of formula (A)
Figure NL1039698AC00111
Figure NL1039698AC00111
 • en een gesubstitueerd fenol met formule (B)• and a substituted phenol of formula (B)
Figure NL1039698AC00112
Figure NL1039698AC00112
 2. Samenstelling volgens conclusie 1, waarbij R in het gealkyleerde polyamine (A) een lineaire of vertakte Cl - C24 alkyl of alkylaryl keten voorstelt.The composition of claim 1, wherein R in the alkylated polyamine (A) represents a linear or branched C 1 -C 24 alkyl or alkylaryl chain. 3. Samenstelling volgens conclusie 1 of 2, waarbij R = C6-C18 lineaire alkylketen.The composition according to claim 1 or 2, wherein R = C 6 -C 18 linear alkyl chain. 4. Samenstelling volgens één of meer van de conclusies 1-3, waarbij R = C8-C14 lineaire alkylketen.The composition of any one of claims 1-3, wherein R = C8 -C14 linear alkyl chain. 5. Samenstelling volgens één of meer van de conclusies 1-4, waarbij n = 0 tot 10.The composition of any one of claims 1-4, wherein n = 0 to 10. 6. Samenstelling volgens één of meer van de conclusies 1-5, 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 1-5, wherein the amino groups in polyamine (A) are linked via linear alkyl ((CH2) m), branched alkyl ((CH2) m), alkylaryl ((CH2) m (6) aryl), poly (aryl), alkylene or poly (alkylene) groups. 7. Samenstelling volgens één of meer van de conclusies 1-6, 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 1-6, wherein the amino groups in polyamine (A) are connected via linear alkyl ((CH 2) m) with m = 1 to 10. 8. Samenstelling volgens één of meer van de conclusies 1-7, waarbij de aminogroepen in polyamine (A) zijn verbonden via een propyleengroep ((CH2)3).A composition according to any one of claims 1-7, wherein the amino groups in polyamine (A) are connected via a propylene group ((CH 2) 3). 9. Samenstelling volgens één of meer van de conclusies 1-8, waarbij het gealkyleerde polyamine (A) dodecylpropyleendiamine is.The composition of any one of claims 1-8, wherein the alkylated polyamine (A) is dodecylpropylene diamine. 10. Samenstelling volgens één of meer van de conclusies 1-9, waarbij het gealkyleerde polyamine (A) alkyldipropyleentriamine is.The composition of any one of claims 1 to 9, wherein the alkylated polyamine (A) is alkyl dipropylene triamine. 11. Samenstelling volgens één of meer van de conclusies 1-10, waarbij het gealkyleerde polyamine het overeenkomende polymeer van (A) is.The composition of any one of claims 1-10, wherein the alkylated polyamine is the corresponding polymer of (A). 12. Samenstelling volgens één of meer van de conclusies 1-11, 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 (CHO).A composition according to any one of claims 1 to 11, 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). 13. Samenstelling volgens één of meer van de conclusies 1-12, 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 1-12, 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). 14. Samenstelling volgens één of meer van de conclusies 1-13, waarbij het gesubstitueerde fenol (B) catechol of salicylzuur is.A composition according to any one of claims 1-13, wherein the substituted phenol (B) is catechol or salicylic acid. 15. Samenstelling volgens één of meer van de conclusies 1-14, waarbij gesubstitueerd fenol (B) salicylzuur is.The composition of any one of claims 1-14, wherein substituted phenol (B) is salicylic acid. 16. Vloeistof volgens één of meer conclusies 1-15, 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 is.Liquid according to one or more of claims 1-15, 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 is. 17. Vloeistof volgens één of meer van de conclusies 1-16, bestaande uit gealkyleerd polyamine (A) en gesubstitueerd fenol (B) waarbij de molverhouding van A tot B 1,2 tot 0,8 is.A liquid according to any one of claims 1-16, consisting of alkylated polyamine (A) and substituted phenol (B) wherein the molar ratio of A to B is 1.2 to 0.8. 18. Vloeistof volgens één of meer van de conclusies 1-17, bestaande uit gealkyleerd polyamine (A) en gesubstitueerd fenol (B) waarbij de molverhouding van A tot B 1 tot 1 is.A liquid according to any one of claims 1-17, consisting of alkylated polyamine (A) and substituted phenol (B) wherein the molar ratio of A to B is 1 to 1. 19. Vloeistof die werkt als hardingsmiddel en/of oppervlakteactieve samenstelling, bestaande uit 50 - 99 gew.% dodecylpropyleendiamine en 1 - 50 gew.% salicylzuur.19. Liquid acting as a hardener and / or surfactant composition consisting of 50 - 99% by weight dodecylpropylenediamine and 1 - 50% by weight salicylic acid. 20. Samenstelling volgens conclusie 19, waarbij het mengsel 60 - 70 gew.% dodecylpropyleendiamine en 30 - 40 gew.% salicylzuur bevat.The composition of claim 19, wherein the mixture contains 60 to 70% by weight of dodecylpropylenediamine and 30 to 40% by weight of salicylic acid. 21. Samenstelling volgens één of meer van de conclusies 1-20, 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 gesubstitueerde polycyclische koolwaterstof.A composition according to any one of claims 1-20, 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. 22. Samenstelling volgens conclusie 21, waarbij het gehydroxyleerde thiofeen, gehydroxyleerde pyridine, gehydroxyleerde pyrrool, gehydroxyleerde furan, gehydroxyleerde polycyclische koolwaterstof of gehydroxyleerde gesubstitueerde polycyclische koolwaterstof voorts een carbonzuur of carboxylaatgroep omvat.The composition of claim 21, 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. 23. Vloeistofsamenstelling die omvat: • Bisgealkyleerd amine (C) , met formule R' NHR'' en • Gesubstitueerd fenol (B)A liquid composition comprising: • bis-alkylated amine (C), of formula R “NHR” “and • substituted phenol (B)
Figure NL1039698AC00141
Figure NL1039698AC00141
 24. Samenstelling volgens conclusie 23, waarbij het bisgealkyleerde amine (C) bis(vetalkyl)amine met verzadigde, onverzadigde, lineaire en/of vertakte C6-C24 alkylketens of mengsels daarvan is.The composition of claim 23, wherein the bisalkylated amine is (C) bis (fatty alkyl) amine with saturated, unsaturated, linear and / or branched C 6 -C 24 alkyl chains or mixtures thereof. 25. Samenstelling volgens conclusie 23-24, waarbij het bisgealkyleerde amine (C) bis(vetalkyl)amine met C14-C20 verzadigde lineaire alkylketens, is.The composition of claims 23-24, wherein the bisalkylated amine is (C) bis (fatty alkyl) amine C14 -C20 saturated linear alkyl chains. 26. Samenstelling volgens één of meer van de conclusies 23-25, 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 (CHO).The composition of any one of claims 23 to 25, 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). 27. Samenstelling volgens één of meer van de conclusies 23-26, 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 of claims 23-26, 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). 28. Samenstelling volgens één of meer van de conclusies 23-27, waarbij gesubstitueerd fenol (B) catechol of salicylzuur is.The composition of any one of claims 23 to 27, wherein substituted phenol (B) is catechol or salicylic acid. 29. Samenstelling volgens één of meer van de conclusies 23-28, waarbij gesubstitueerd fenol (B) salicylzuur is.The composition of any one of claims 23 to 28, wherein substituted phenol (B) is salicylic acid. 30. Vloeistof volgens één of meer van de conclusies 23-29, bestaande uit bis(gealkyleerd) amine (C) en gesubstitueerd fenol (B) in een molverhouding van 0,6 tot 1,4.A liquid according to any one of claims 23 to 29, consisting of bis (alkylated) amine (C) and substituted phenol (B) in a molar ratio of 0.6 to 1.4. 31. Vloeistof volgens één of meer van de conclusies 23-30, bestaande uit bis(gealkyleerd) amine en gesubstitueerd fenol (B) in een molverhouding van 1,4 tot 0,6.A liquid according to any one of claims 23-30, consisting of bis (alkylated) amine and substituted phenol (B) in a molar ratio of 1.4 to 0.6. 32. Vloeistof volgens één of meer van de conclusies 23-31, bestaande uit bis(gealkyleerd) amine (C) en gesubstitueerd fenol (B) waarbij de molverhouding van A tot B 1 tot 1 is.The fluid of any one of claims 23 to 31, consisting of bis (alkylated) amine (C) and substituted phenol (B) wherein the molar ratio of A to B is 1 to 1. 33. Samenstelling volgens één of meer van de conclusies 23-32, 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 gesubstitueerde polycyclische koolwaterstof.A composition according to any one of claims 23-32, 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 hydrocarbon. 34. Samenstelling volgens conclusie 33, waarbij het gehydroxyleerde thiofeen, gehydroxyleerde pyridine, gehydroxyleerde pyrrool, gehydroxyleerde furan, gehydroxyleerde polycyclische koolwaterstof of gehydroxyleerde gesubstitueerde polycyclische koolwaterstof voorts een carbonzuur of carboxylaatgroep omvat.The composition of claim 33, 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.
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