Stabilized crosslinking composition
View Patent ↗This invention relates to a crosslinking composition comprising an organic acid and a compound having the structure of Formula I: A′-NR A —R D wherein A′, R A , and R D are defined in the specification. This invention also relates to a process for producing the crosslinking composition by reacting an amino compound containing amino groups; a mono(alkylaldehyde) and/or a poly(alkylaldehyde), and an alcohol; and adding an organic compound where said amino compound is selected from the group consisting of: triazine, linear or cyclic ureas, cyanuric acid, substituted cyanuric acids, linear or cyclic amides, glycolurils, hydantoins, linear or cyclic carba mates and mixtures thereof.
1. A stabilized crosslinking composition consisting essentially of:
(I) a compound of Formula I:
A′-NR A —R D (Formula 1),
in which A′ is selected from: (a) a monovalent moiety of a compound selected from: linear ureas, cyclic ureas, cyanuric acid, substituted cyanuric acids, linear amides, cyclic amides, glycolurils, hydantoins, linear carbamates, cyclic carbamates and mixtures thereof, and (b) a moiety of Formula 2:
R A is selected from: R D , hydrogen, C 1-20 alkyl, and where R A taken together with A′ forms a cyclic compound; R D is <—CHR C OR B , where
R B is selected from: hydrogen, C 1-24 alkyl, C 3-24 aryl, C 4-24 aralkyl and C 4-24 alkaryl; and
R C is selected from: optionally halogenated C 1-24 alkyl; C 3-24 aryl, optionally halogenated C 4-24 aralkyl; C 2-24 alkoxyalkyl, and C 4-24 alkaryl, and
A is a monovalent moiety of a compound selected from: linear ureas, cyclic ureas, cyanuric acid, substituted cyanuric acids, linear amides, cyclic amides, glycolurils, hydantoins, linear carbamates, cyclic carbamates and mixtures thereof;
B is a divalent residue of a poly(alkylaldehyde) with n aldehyde groups;
n is an integer of from 2 to 8 (inclusive);
R a is selected from: R d , hydrogen, C 1-20 alkyl and where R a taken together with A forms a cyclic compound; and
R b selected from: hydrogen, C 1-24 alkyl, C 3-24 aryl, C 4-24 aralkyl and C 4-24 alkaryl; where
R d is selected from: a radical <—CHR C OR b and a moiety of Formula 3:
R c is selected from: optionally halogenated C 1-24 alkyl; C 3-24 aryl; optionally halogenated C 4-24 aralkyl; C 2-24 alkoxyalkyl; and C 4-24 alkaryl;
and where, when A′ is from a compound other than triazine, the alkyl and aryl groups in each radical may optionally have heteroatoms in their structure;
(II) a carboxylic acid group containing organic acid stabilizer in amount of from 1:50 to 50:1 moles of the amount of moles of (I) the compound of Formula 1; and
(III) a solvent.
2. The crosslinking composition of claim 1 , where the mole ratio of the carboxylic acid stabilizer (II) to the compound of Formula 1 (I) is from 1:20 to 20:1.
3. The crosslinking composition of claim 2 , where the mole ratio of the carboxylic acid stabilizer (II) to the compound of Formula 1 (I) is from 1:10 to 10:1.
4. The crosslinking composition of claim 3 , where the mole ratio of the carboxylic acid stabilizer (II) to the compound of Formula 1 (I) is from 1:5 to 4:1.
5. The crosslinking composition of claim 4 , where the mole ratio of the carboxylic acid stabilizer (II) to the compound of Formula 1 (I) is from 1:2.5 to 2:1.
6. The crosslinking composition of claim 5 , where the mole ratio of the carboxylic acid stabilizer (II) to the compound of Formula 1 (I) is from 1:2 to 1.5:1.
7. The crosslinking composition of claim 6 , where the mole ratio of the carboxylic acid stabilizer (II) to the compound of Formula 1 (I) is 1:1.
8. The crosslinking composition of claim 1 , where (I) A′ is from a compound other than a triazine.
9. The crosslinking composition of claim 1 , where (I) A′ is other than a moiety of Formula 2.
10. The crosslinking composition of claim 1 , where (II) the organic acid stabilizer is selected from: acetic acid, formic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, benzoic acid, phthalic acid, carbonic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, malic acid, tartaric acid, citric acid, latic acid, glycolic acid, glyoxylic acid, and mixtures thereof.
11. The composition according of claim 10 , where (II) the organic acid is selected from: acetic acid, formic acid, propionic acid and mixtures thereof.
12. The crosslinking composition of claim 10 , where (II) the organic acid stabilizer is selected from: glacial acetic acid, monohalogenated acetic acids and polyhalogenated acetic acids.
13. The crosslinking composition of claim 1 , where (I) the compound of Formula 1 is selected from: compounds where R D is <—CHR C OR B and compounds where A′ is Formula 2; and where
R b (where present) and R B are independently derived from alcohols selected from: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, cyclohexanol, phenol, benzyl alcohol, monoalkyl ether of ethylene, monoalkyl ether of propylene glycol and mixtures thereof.
14. The crosslinking composition of claim 1 , where (I) A′ is Formula 2 and
B is from compounds selected from: glutaraldehyde, the reaction products of crotonaldehyde and polyhydritic alcohols, adducts of α,β-unsaturated aldehydes; and polymers of α,β-unsaturated aldehydes.
15. The crosslinking composition of claim 1 , where (I) the compound of Formula 1 is selected from: compounds where R D is <—CHR C OR B and compounds where A′ is Formula 2; and where
R c (where present) and R C are independently C 1-8 alkyl; and
R b (where present) and R B are independently selected from:
C 1-8 alkyl and C 1-8 alkoxyalkyl.
16. The crosslinking composition of claim 1 , where (I) A′ is from a compound selected from: melamines, guanamines, linear ureas, cyclic ureas and mixtures thereof.
17. A process for producing the crosslinking composition of claim 1 , comprising the steps of:
(A) producing a compound of Formula 1, by reacting
(i) an amino group containing a compound selected from: linear ureas, cyclic ureas, cyanuric acid, substituted cyanuric acids, linear amides, cyclic amides, glycolurils, hydantoins, linear carbamates, cyclic carbamates and mixtures thereof;
(ii) an aldehyde selected from: a mono(alkylaldehyde), a poly(alkylaldehyde) and mixtures thereof; and
(iii) an alcohol; and
(B) adding an organic acid comprising a carboxylic acid group where the molar ratio of the organic acid (B) to the amino compound (A)(i) is from 1:50 to 50:1;
with the proviso that where A′ is other than Formula 2, the aldehyde (A)(ii) is a mono (alkylaldehyde).
18. The process of claim 17 , where the mole ratio of the carboxylic acid stabilizer (B) to the amino compound (A)(i) is from 1:20 to 20:1.
19. The process of claim 18 , where the mole ratio of the carboxylic acid stabilizer (B) to the amino compound (A)(i) is from 1:10 to 10:1.
20. The process of claim 19 , where the mole ratio of the carboxylic acid stabilizer (B) to the amino compound (A)(i) is from 1:5 to 4:1.
21. The process of claim 20 , where the mole ratio of the carboxylic acid stabilizer (B) to the amino compound (A)(i) is from 1:2.5 to 2:1.
22. The process of claim 21 , where the mole ratio of the carboxylic acid stabilizer (B) to the amino compound (A)(i) is from 1:2 to 1.5:1.
23. The process of claim 22 , where the mole ratio of the carboxylic acid stabilizer (B) to the amino compound (A)(i) is 1:1.
24. The process of claim 17 , where A′ is a moiety from a triazine and the aldehyde (A)(ii) is a mono (alkylaldehyde).
25. The process of claim 17 , wherein at least some of the organic acid (B) is added before or during the reaction (A).
26. The process of claim 17 , wherein at least some of the organic acid (B) is added after the reaction (A).
27. The process of claim 17 , where the amino compound (A)(i) is selected from: melamine, guanamine, linear urea, cyclic urea and mixtures thereof.
28. The process of claim 17 , where the mono(alkylaldehyde) (A)(ii) is selected from: acetaldehyde, propionaldehyde, n-butyraldehyde, isobutyraldehyde, valeraldehyde, chloral, caproaldehyde, octylaldehyde, acrolein and crotonaldehyde.
29. The process of claim 17 , wherein the poly(alkylaldehyde) (A)(ii) is selected from: glutaraldehyde, the reaction product of crotonaldehyde and polyhydritic alcohols; adducts of α,β-unsaturated aldehydes and polymers of α,β-unsaturated aldehydes.
30. The process of claim 17 , where the alcohol (A)(iii) is selected from: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, cyclohexanol, phenol, benzyl alcohol, monoalkyl ether of ethylene, monoalkyl ether of propylene glycol and mixtures thereof.
31. The process of claim 17 , where the organic acid (B) is selected from: acetic acid, formic acid, propionic acid and mixtures thereof.
32. The process of claim 17 , where A′ is Formula 2; and:
the molar ratio of the amino group (A)(i) to the mono(alkylaldehyde) (A)(ii) is 1:0.1 to 1:30,
the molar ratio of amino group (A)(i) to the aldehyde groups in the poly(alkylaldehyde) (A)(ii) is 0.1:1 to 50:1; and
the molar ratio of aldehyde groups in the mono(alkylaldehyde) (A)(ii) and the poly(alkylaldehyde) (A)(ii) to the alcohol (A)(iii) is 1:0.2 to 1:50.
33. The process of claim 17 , where A′ is other than Formula 2; and:
the molar ratio of the amino group (A)(i) to the mono(alkylaldehyde) (A)(ii) is 1:0.1 to 1:30, and
the molar ratio of aldehyde groups in the mono(alkylaldehyde) (A)(ii) to the alcohol (A)(iii) is 1:0.2 to 1:50.