Crosslinking composition
View Patent ↗This invention relates to a crosslinking composition comprising a compound having the structure of Formula I: A′-NR A —R D where A′ is a moiety derived from the group consisting of linear or cyclic ureas, cyanuric acid, substituted cyanuric acids, linear or cyclic amides, glycolurils, hydantoins, linear or cyclic carbamates and mixtures thereof, or a moiety comprising the structure: where R A is R D , hydrogen, an alkyl of 1 to 20 carbon atoms, or taken together with A′ forms a cyclic compound; R D is —CHR C OR B , wherein R B is hydrogen, alkyl, aryl, aralkyl or an alkaryl having from 1 to about 24 carbon atoms and R C is an alkyl, halogenated alkyl, aryl, aralkyl, halogenated aralkyl, alkoxyalkyl or an alkaryl having from 1 to about 24 carbon atoms; A is a moiety derived from the group consisting of linear or cyclic ureas, cyanuric acid, substituted cyanuric acids, linear or cyclic amides, glycolurils, hydantoins, linear or cyclic carbamates and mixtures thereof; B is a residue of a poly(alkylaldehyde) with n aldehyde groups; n is an integer of 2 to about 8; R a is R d , hydrogen, an alkyl of 1 to about 20 carbon atoms, or taken together with A forms a cyclic compound; where R d is CHR c OR b or where R b is hydrogen, alkyl, aryl, aralkyl or an alkaryl having from 1 to about 24 carbon atoms and R c is an alkyl, halogenated alkyl, aryl, aralkyl, halogenated aralkyl, alkoxyalkyl or an alkaryl having from 1 to about 24 carbon atoms; and where the alkyl or aryl groups in each radical may optionally have heteroatoms in their structure. 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; where said amino compound is selected from the group consisting of: linear or cyclic ureas, cyanuric acid, substituted cyanuric acids, linear or cyclic amides, glycolurils, hydantoins, linear or cyclic carbamates and mixtures thereof.
1. A crosslinking composition comprising the structure of Formula I:
A′-NR A —R D (Formula 1)
wherein A′ represents a moiety from Group 2 optionally mixed with a moiety from Group 1; wherein
Group 1 consists of: a mono or divalent moiety derived from melamine or guanamine; and
Group 2 consists of:
(a) a monovalent or divalent 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′ is a divalent moiety (together forming a cyclic compound when attached to the nitrogen in Formula 1); R A is selected from divalent R D , a bond and C 1-20 alkylene;
R D is <—CHR C OR B , wherein
R B is selected from: 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 or divalent 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 represents a mixture of residues from propionaldehyde and from glutaraldehyde;
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: C 1-24 alkyl, C 3-24 aryl, C 4-24 aralkyl and C 4-24 alkaryl; wherein
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 wherein the alkyl and aryl groups in each radical may optionally have heteroatoms in their structure.
2. The composition of claim 1 , wherein said compound having the Formula 1 is an oligomer having a number average molecular weight of from about 200 to about 500.
3. The composition of claim 1 , wherein A and A′ are each independently moieties derived from a mixture of ureas and glycolurils.
4. The composition of claim 1 , wherein A and A′ are each independently moieties derived from a mixture of melamine, urea and glycoluril.
5. A process for producing the cross-linking composition of claim 1 , comprising reacting:
(i) an amino group containing 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) a mixture of propionaldehyde and glutaraldehyde;
(iii) an alcohol; and
(iv) optionally a melamine and/or guanamine.
6. The process of claim 5 wherein said amino group containing compounds are a mixture of ureas and glycolurils.
7. The process of claim 5 wherein said ingredients (i) and (iv) are together a mixture of melamine, urea and glycoluril.
8. The process of claim 5 , wherein said alcohol is selected from the group consisting of: methanol, ethanol, propanol, isopropanol, butanol, isobutanol, cyclohexanol, phenol, benzyl alcohol, monoalkyl ether of ethylene glycol, monoalkyl ether of propylene glycol and mixtures thereof.
9. The process of claim 5 , wherein the molar ratio of the amino groups of said ingredient (i) and said ingredient (iv) where present to the propionaldehyde of said ingredient (ii) is from 1:0.1 to 1:30; the molar ratio of amino groups of said ingredient (i) and said ingredient (iv) where present to the aldehyde groups in the glutaraldehyde of said ingredient (ii) is from 0.1:1 to 50:1; and the molar ratio of aldehyde groups in said ingredient (ii) to said ingredient (iii) is from 1:0.2 to 1:50.
10. A curable composition comprising:
(i) the cross-linking composition of claim 1 ;
(ii) an active-hydrogen containing material; and
(iii) optionally a cure catalyst.