IP Library Granted Patent US 7,557,168
Granted Patent B2
US 7,557,168 · App. 11/891,446 · Granted Jul 7, 2009

Applying adhesive stream of epoxy resin, rubber modified epoxy resin and capped isocyanate prepolymer

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Quick Facts
Patent No.
US 7,557,168
App. No.
11/891,446
Granted
Jul 7, 2009
Kind
B2
Abstract

The invention is a composition comprising applying to a substrate a stream of an adhesive comprising: one or more epoxy resins; one or more rubber modified epoxy resins; one or more toughening compositions comprising the reaction product of one or more isocyanate terminated prepolymers and one or more capping compounds having one or more phenolic, benzyl alcohol, aminophenyl, or, benzylamino groups wherein the reaction product is terminated with the capping compounds; one or more curing agents for epoxy resins and one or more catalysts which initiate cure at a temperature of about 100° C. or greater; and optionally; fillers adhesion promoters, wetting agents or rheological additives useful in epoxy adhesive compositions; wherein the adhesive composition has a viscosity at 45° C. of about 20 Pa·s to about 400 Pa.s. The composition can be used as an adhesive and applied as a stream using a high speed streaming process.

Claims (57)

1. A method of applying an adhesive composition comprising applying a stream of the adhesive composition to a substrate at a speed of from about 200 to about 500 mm/s, wherein the adhesive composition comprises,

A. one or more epoxy resins;

B. one or more rubber modified epoxy resins;

C. one or more toughening compositions comprising the reaction product of one or more isocyanate terminated prepolymers and one or more capping compounds having one or more bisphenolic, phenolic, benzyl alcohol, aminophenyl or, benzylamino moieties wherein the reaction product is terminated with the capping compound;

D. one or more curing agents and one or more catalysts for epoxy resins which initiates cure at a temperature of about 100° C. or greater; and

E. optionally; fillers, adhesion promoters, wetting agents and rheological additives useful in epoxy adhesive compositions;

wherein the adhesive composition has a viscosity at 45° C. of about 20 Pa·s to about 400 Pa.

2. A method according to claim 1 wherein the toughening agent has a crosslink density of about 2 or less.

3. A method of claim 1 wherein the capping compound corresponds to the formula

wherein

R 4 is a direct bond or an alkylene, carbonyl, oxygen, carboxyloxy or amido moiety;

R 5 is independently in each occurrence an alkyl, alkenyl, alkyloxy or aryloxy moiety with the proviso that if p=1 then q=0;

X is O or —NR 6 with the proviso that X is O where p is 1; and that where p is 0, X is O in at least one occurrence;

o is independently in each occurrence 0 or 1 if p is 0, and 0 if p is 1;

p is independently in each occurrence 0 or 1; and

q is independently in each occurrence a number of from 0 to 1.

4. A method according to claim 1 wherein the bisphenolic, phenolic, benzyl alcohol, aminophenyl or, benzylamino moieties of the capping compound contains one aromatic moiety and one aliphatic substituent on the aromatic ring which does not interfere in the reaction of the amino or hydroxyl groups with an isocyanate groups.

5. The method according to claim 4 wherein the isocyanate terminated prepolymer corresponds to one of the formulas

wherein

R 1 is independently in each occurrence a C 2-20 m valent alkyl moiety;

R 2 is independently in each occurrence a polyether chain;

R 3 is independently in each occurrence an alkylene, cycloalkylene or mixed alkylene and cycloalkylene moiety;

X is O or —NR 6 with the proviso that X is O where p is 1; and that where p is 0, X is O in at least one occurrence;

R 6 is independently in each occurrence hydrogen or alkyl;

m is independently in each occurrence a number of 1 to 6; and

n is independently in each occurrence a number of 1 or greater.

6. A composition according to claim 1 wherein the toughening composition corresponds to one of the formulas

wherein

R 1 is independently in each occurrence a C 2-20 m valent alkyl moiety;

R 2 is independently in each occurrence a polyether chain;

R 3 is independently in each occurrence an alkylene, cycloalkylene or mixed alkylene and cycloalkylene moiety, optionally containing one or more oxygen or sulfur atoms;

R 4 is a direct bond or an alkylene, carbonyl, oxygen, carboxyloxy, or amido moiety;

R 5 is independently in each occurrence an alkyl, alkenyl, alkyloxy or aryloxy moiety with the proviso that if p=1 then q=0;

X is O or —NR 6 with the proviso that X is O where p is 1; that where p is 0, X is O in at least one occurrence;

R 6 is independently in each occurrence hydrogen or alkyl;

m is independently in each occurrence a number of about 1 to about 6;

n is independently in each occurrence a number of 1 or greater;

o is independently in each occurrence 0 or 1 if p is 0, and 0 if p is 1;

p is independently in each occurrence 0 or 1; and

q is independently in each occurrence a number of from 0 to 1.

7. A method according to claim 6 wherein

R 1 is independently in each occurrence a 2 to 3 valent C 2-8 alkyl moiety;

R 2 is a polyalkylene polyether chain having a weight average molecular weight of about 400 to about 4000;

R 3 is independently in each occurrence a C 1-20 alkylene, cycloalkylene or mixed alkylene and cycloalkylene moiety;

R 4 is a C 1-20 straight or branched chain alkylene moiety;

R 5 is independently in each occurrence C 1-20 alkyl, C 2-20 alkenyl, C 1-20 alkoxy or

C- 6-20 aryloxy moiety with the proviso that where p is 0, R 5 is a C 1-20 alkyl moiety;

R 6 is independently in each occurrence hydrogen or C 1-4 alkyl moiety;

m is independently in each occurrence about 2 to about 4;

n is independently in each occurrence about 1 to about 3;

p is independently in each occurrence a number of 0 or 1 and

q is 0 or 1.

8. A method according to claim 2 wherein the adhesive demonstrates a viscosity of about 30 Pa·s to about 150 Pa·s at 45° C.

9. A method according to claim 8 wherein the adhesive is sprayed as a bead from a nozzle which is located about 3 to about 10 mm from the substrate surface.

10. A method according to claim 8 wherein the adhesive is sprayed using a pressure of about 50 to about 300 bar.

11. A method according to claim 8 wherein the adhesive is sprayed at a temperature of about 20° C. to about 65° C.

12. A method according to claim 11 wherein the adhesive is subjected to heating to a temperature at which the curing agent initiates cure of the adhesive.

Assignments (6)
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 Nov 1, 2017
From: LUTZ, ANDREAS; ROHRER, PAUL; SCHONBACHLER, HANS
To: DOW EUROPE GMBH
Reel/Frame 044009/0454 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 1, 2017
From: DOW EUROPE GMBH
To: THE DOW CHEMICAL COMPANY
Reel/Frame 044009/0535 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 1, 2017
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 044009/0603 →