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US 5,859,153 AGranted
Novolak compounds useful as adhesion promoters for epoxy resins
AssigneeMinnesota Mining and Manufacturing Company
InventorsAlan R. Kirk, Allen L. Griggs
Life of this patent
Estimating the term…
Abstract
A composition useful as a powder coating comprises an epoxy resin and a novolak compound or resin having a structure obtained from the reaction of a substituted phenol such as cresol and an aldehyde to form a substituted bis(hydroxymethyl) phenol intermediate which is then reacted with a polyhydroxyphenol containing adjacent hydroxyl groups such as catechol to yield a polyhydroxyphenol-endcapped novolak compound or resin.
Claims7
A curable composition comprising:
- (a) an epoxy resin;
- (b) a compound comprising a polymer of the formula:
- ##STR4## wherein:
- R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are each independently selected from the group consisting of --OH, --SH, --H, C.sub.1-20 alkyl, --F, --Cl, --Br, --I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are selected such that at least two vicinal groups selected from the group consisting of --OH, --SH, and combinations thereof are present on a ring structure to which R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are attached;
- one of the groups selected from the group consisting of R.sup.6, R.sup.7, and R.sup.9 are --OH or --SH and the remainder of the groups selected from the group consisting of R.sup.6, R.sup.7, and R.sup.9 are selected independently from the group consisting of --H, C.sub.1-20 alkyl, --F, --Cl, --Br, --I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.8 is selected from the group consisting of C.sub.1-20 alkyl, --H, --F, --Cl, --Br, --I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.11 is selected from the group consisting of --OH and --SH,
- R.sup.10 and R.sup.12 are each independently selected from the group consisting of --OH, --SH, --H, C.sub.1-20 alkyl, --F, --Cl, --Br, --I, alkoxy, aryl, alkaryl, and alkenyl groups;
- wherein at least one of R.sup.10 and R.sup.12 is --OH or --SH;
- R.sup.13 is selected from the group consisting of --H, C.sub.1-20 alkyl, --OH, --SH, --F, --Cl, --Br, --I, alkoxyl, aryl, alkaryl, and alkenyl groups;
- one of the groups selected from R.sup.14, R.sup.15, and R.sup.17 are --OH or --SH and the remainder of the groups selected from the group consisting of R.sup.14, R.sup.15, and R.sup.17 are independently selected from the group consisting of --H, C.sub.1-20 alkyl, --F, --Cl, --Br, --I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.16 is selected from the group consisting of C.sub.1-20 alkyl, --H, --F, --Cl, --Br, --I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.18, R.sup.19, R.sup.20, R.sup.21, and R.sup.22 are each independently selected from the group consisting of --OH, --SH, --H, C.sub.1-20 alkyl, --F, --Cl, --Br, --I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.18, R.sup.19, R.sup.20, R.sup.21, and R.sup.22 are selected such that at least two vicinal groups selected from the group consisting of --OH, --SH, and combinations thereof are present on a ring structure to which R.sup.18, R.sup.19, R.sup.20, R.sup.21, and R.sup.22 are attached;
- and
- n is an integer of zero or greater;
- (c) a catalyst;
- (d) optionally a hygroscopic solvent;
- and
- (e) optionally a curing agent different than that of element (b).
18 more elements
A process of promoting adhesion properties of an epoxy resin, the process comprising the step of adding a compound of the formula:
- ##STR5## wherein:
- R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are each independently selected from the group consisting of OH, SH, H, C.sub.1-20 alkyl, F, Cl, Br, I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are selected such that at least two vicinal groups selected from the group consisting of OH, SH, and combinations thereof are present on a ring structure to which R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are attached;
- one of the groups selected from the group consisting of R.sup.6, R.sup.7, and R.sup.9 are OH or SH and the remainder of the groups selected from the group consisting of R.sup.6, R.sup.7, and R.sup.9 are selected independently from the group consisting of H, C.sub.1-20 alkyl, F, Cl, Br, I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.8 is selected from the group consisting of C.sub.1-20 alkyl, H F, Cl, Br, I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.11 is selected from the group consisting of OH and SH;
- R.sup.10 and R.sup.12 are each independently selected from the group consisting of OH, SH, H, C.sub.1-20 alkyl, F, Cl, Br, I, alkoxy, aryl,,alkaryl, and alkenyl groups;
- wherein at least one of R.sup.10 and R.sup.12 is OH or SH;
- R.sup.13 is selected from the group consisting of H, C.sub.1-20 alkyl, OH, SH, F, Cl, Br, I, alkoxyl, aryl, alkaryl, and alkenyl groups;
- one of the groups selected from R.sup.14, R.sup.15, and R.sup.17 are OH or SH and the remainder of the groups selected from the group consisting of R.sup.14, R.sup.15, and R.sup.17 are independently selected from the group consisting of C.sub.1-20 alkyl, F, Cl, Br, I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.16 is selected from the group consisting of C.sub.1-20 alkyl, H, F, Cl, Br, I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.18, R.sup.19, R.sup.20, R.sup.21, and R.sup.22 are each independently selected from the group consisting of OH, SH, H, C.sub.1-20 alkyl, F, Cl, Br, I, alkoxy, aryl, alkaryl, and alkenyl groups;
- R.sup.18, R.sup.19, R.sup.20, R.sup.21, and R.sup.22 are selected such that at least two vicinal groups selected from the group consisting of OH, SH, and combinations thereof are present on a ring structure to which R.sup.18, R.sup.19, R.sup.20, R.sup.21, and R.sup.22 are attached;
- and
- n is an integer of zero or greater.
12 more elements
Dependencies are inferred from the claim text.