Accelerator solution and process for curing curable resins
AssigneeAkzo Nobel Chemicals International B.V.
InventorsFrederik Willem Karel Koers, Johannes Martinus Gerardus Maria Reijnders, Auke Gerardus Talma, Johannes Hermanus Ter Beek
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Abstract
Solution suitable for accelerating the cure of a curable resin using a peroxide, said accelerator solution comprising (i) at least one organic solvent, (ii) a manganese salt, a copper salt, or a combination thereof, and (iii) an iron complex of a tetradentate, pentadentate or hexadentate nitrogen donor ligand.
Claims18
Accelerator solution comprising (I) at least one organic solvent, (II) a manganese salt, a copper salt, or a combination thereof, end (III) an iron complex of a tetradentate, pentadentate or hexadeniate nitrogen donor ligand according to any of the formulae (I), (II), (III), (IV), (V), and (VI),
- the ligand of formula (I) having the following structure:
- wherein each R is independently selected from:
- hydrogen, F, Cl, Br, hydroxyl, C1-12-alkylO—, —NH—CO—H, —NH—CO—C1-12-alkyl, —NH2, —NH—C1-12-alkyl, and C1-12-alkyl;
- R1 and R2 are independently selected from:
- C1-24-alkyl, C6-10-aryl, and a group containing a heteroatom capable of coordinating to a transition metal;
- R3 and R4 are independently selected from hydrogen, C1-12 alkyl, C1-12-alkyl-O—C1-12-alkyl, C1-12-alkyl-O—C6-10-aryl, C6-10-aryl, C1-12-hydroxyalkyl, and —(CH2)n—C(O)OR5, wherein R5 is independently selected from hydrogen and C1-4-alkyl and n ranges from 0 to 4,
- X Is selected from C═O, —[C(R6)2]y- wherein y ranges from 0 to 3 and each R6 is independently selected from hydrogen, hydroxyl, C1-12-alkoxy, and C1-12-alkyl;
- the ligand of formula (II) having the following structure:
- wherein each R1 and R2 independently represents —R4-R5,
- R3 represents hydrogen, optionally substituted alkyl, aryl or arylalkyl or —R4-R5,
- each R4 independently representing a single bond or optionally substituted alkylene, alkenylene, oxyalkylene, aminoalkylene, alkylene ether, carboxylic ester or carboxylic amide, and
- each R5 independently representing an optionally N− substituted aminoalkyl group or an optionally substituted heteroaryl group selected from pyridinyl, pyrazinyl, pyrazolyl, pyrrolyl, imidazolyl, benzimidazolyl, pyrimidinyl, triazolyl, end thiazolyl;
- the ligand of formula (III) having the following structure:
- wherein each R20 is selected from alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, aryl, and arylalkyl groups optionally substituted with a substituent selected from hydroxy, alkoxy, phenoxy, carboxylate, carboxamide, carboxylic ester, sulphonate, amine, alkylamine and N+(R21)3, wherein R21 is selected from hydrogen, alkanyl, alkenyl, arylalkanyl, arylalkenyl, oxyalkanyl, oxyalkenyl, aminoalkanyl, aminoalkenyl, alkanyl ether, alkenyl ether, and —CY2R22, in which Y is
- independently selected from H, CH3, C2H5, C3H7 and R22 is independently selected from optionally substituted pyridinyl, pyrazinyl, pyrazolyl, pyrrolyl, imidazolyl, benzimidazolyl, pyrimidinyl, triazolyl and thiazolyl groups, and wherein at feast one of R20 is —CY2—R22;
- the ligand of formula (IV) having the following structure:
- wherein Q is independently selected from
- wherein p is 4, R is independently selected from hydrogen, C1-12alkyl, CH2CH2OH, pyridin-2ylmethyl, and CH2COOH;
- R1, R2, R3, R4, R5 and R6 are independently selected from H, C1-12-alkyl, and C1-12-alkylhydroxy;
- the ligand of formula (V) having the following structure:
- wherein R1 is independently selected from H and linear or branched, substituted or unsubstituted C1-20-alkyl, -alkylaryl, -alkenyl or -alkynyl:
- and all nitrogen atoms in the macropolycyclic rings are capable of coordinating to transition metals;
- the ligand of formula (VI) having the following structure:
- (R17)(R17)N—X—N(R17)(R17) (VI)
- wherein X is selected from —CH2CH2—, —CH2CH2CH2—, and —CH2C(OH)HCH2—;
- and each R17 is independently selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, aryl and arylalkyl groups optionally substituted with a substituent selected from hydroxy, alkoxy, phenoxy, carboxylate, carboxamide, carboxylic ester, sulphonate, amine, alkylamine and N+(R19)3, wherein R19 is selected from hydrogen, alkanyl, alkenyl, arylalkanyl, arylalkenyl, oxyalkanyl, oxyalkenyl, aminoalkanyl, aminoalkenyl, alkanyl ether, alkenyl ether, and —CY2—R18, in which Y is independently selected from H, CH3, C2H5, C3H7 and R18 is independently selected from an optionally substituted heteroaryl group selected from pyridinyl, pyrazinyl, pyrazolyl, pyrrolyl, imidazolyl, benzimidazolyl, pyrimidinyl, triazolyl and thiazolyl;
- and wherein at least two of R17 are —CY2—R16.
Dependencies are inferred from the claim text.