IP Library Granted Patent US 9,951,256
Granted Patent B2
US 9,951,256 · App. 14/636,508 · Granted Apr 24, 2018

Storage-stable heat-activated tertiary amine catalysts for epoxy resins

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Quick Facts
Patent No.
US 9,951,256
App. No.
14/636,508
Granted
Apr 24, 2018
Kind
B2
Abstract

Epoxy adhesive compositions contain a heat-activatable catalyst. The heat-activatable catalyst includes a tertiary amine catalyst and a novolac resin that has a weight average molecular weight of at least 3000. One-component epoxy adhesive formulations that contain the heat-activatable catalyst have unexpectedly good storage stability.

Claims (9)

1. A one-component epoxy adhesive, comprising

A) one or more epoxy resins;

B) at least one epoxy hardener having a melting temperature of at least 50° C.; and

C) a particulate heat-activatable catalyst composition having a volume average particle size of 100 nanometers to 10 microns comprising a mixture of a liquid aminophenol compound selected from the group consisting of 2,6-bis(dimethylaminomethyl)phenol and 2,4-bis(dimethylaminomethyl)phenol, or a solid aminophenol compound that has a boiling temperature of at least 130° C. and a melting temperature of no greater than 60° C.; and a phenol novolac resin that has a weight average molecular weight of 10,000 to 25,000 and a softening temperature of 130 to 200° C.;

wherein the weight ratio of the aminophenol compound and the phenol novolac resin is from 40:60 to 70:30.

2. The one-component epoxy adhesive of claim 1 wherein the heat-activatable catalyst composition is made in a process that includes the steps of:

a) mixing the aminophenol compound with a liquid solution of the phenol novolac resin in ethanol or methanol, at a temperature above the melting temperature of the aminophenol compound but not greater than 80° C. and not greater than the boiling temperature of the ethanol or methanol and at proportions such that from 0.1 to 10 equivalents of phenol groups are provided by the phenol novolac resin per equivalent of tertiary amine groups provided by the aminophenol compound, whereby the reaction mixture separates into a liquid phase containing mainly the ethanol or methanol and a precipitate of the aminophenol compound and the phenol novolac resin;

b) separating the precipitate from the liquid phase while maintaining the temperature of the precipitate at no greater than 80° C. and

c) drying the separated precipitate at a temperature of no greater than 80° C. to remove residual ethanol or methanol from the precipitate.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2024
From: DOW GLOBAL TECHNOLOGIES LLC
To: THE DOW CHEMICAL COMPANY
Reel/Frame 069923/0030 →
CHANGE OF LEGAL ENTITY Recorded Sep 10, 2024
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
Reel/Frame 068907/0881 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2024
From: THE DOW CHEMICAL COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
Reel/Frame 068922/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2018
From: FROESE, ROBERT D.; EAGLE, GLENN G.; JIALANELLA, GARY L.; COLE, ERIC E.; GOLDEN, MICHAEL R.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 045284/0495 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2018
From: LUTZ, ANDREAS
To: DOW EUROPE GMBH
Reel/Frame 045284/0708 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2018
From: DOW EUROPE GMBH
To: THE DOW CHEMICAL COMPANY
Reel/Frame 045284/0847 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2018
From: MING, MING; FENG, SHAOGUANG; LIU, YAN FEI
To: DOW CHEMICAL (CHINA) COMPANY LIMITED
Reel/Frame 045285/0165 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2018
From: DOW CHEMICAL (CHINA) COMPANY LIMITED
To: THE DOW CHEMICAL COMPANY
Reel/Frame 045285/0222 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2018
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 045285/0303 →