IP Library Granted Patent US 11,987,730
Granted Patent B2
US 11,987,730 · App. 16/978,982 · Granted May 21, 2024

Waterbased one coat adhesive composition

Inventors: Stefan Dehnicke (Neu Isenburg, DE); Gerd Becker (Schwalbach, DE); Anna Osichow (Wiesbaden, DE); Philipp Zutavern (Neu Isenburg, DE); Gerald Wessling (Neu Isenburg, DE); David Kistner (Neu Isenburg, DE)
Assignee: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
C09J111/02C08J5/127C08K3/04C08K3/22C08K3/32C08K5/32C08K11/005C09J115/02C09J123/34C08K2003/2296C08K2003/327C09J2400/163C09J2400/166
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,987,730
App. No.
16/978,982
Granted
May 21, 2024
Kind
B2
Abstract

Disclosed is an aqueous adhesive composition which comprises an admixture of: (a) a first aqueous composition comprising, (i) one or more film forming polymers, (ii) one or more lower crystallinity polynitroso compounds, (iii) one or more higher crystallinity polynitroso compounds, and (iv) one or more bismaleimide-containing monomers; and (b) a second aqueous composition comprising (i) an aqueous dispersion of at least one phenolic resin which is a condensation product of a phenol and formaldehyde, wherein the aqueous dispersion is stabilized by at least one polyacrylate; (b) one or more latices formed from one or more halogenated polyolefins; and (c) one or more metal oxides.

Claims (42)

1. An aqueous adhesive composition which comprises an admixture of:

(a) a first aqueous composition comprising, (i) one or more film forming polymers, (ii) one or more lower crystallinity polynitroso compounds, (iii) one or more higher crystallinity polynitroso compounds, and (iv) one or more bismaleimide-containing monomers; and

(b) a second aqueous composition comprising (i) an aqueous dispersion of at least one phenolic resin which is a condensation product of a phenol and formaldehyde, wherein the aqueous dispersion is stabilized by at least one polyacrylate derived from a monomer represented by Formula I:

wherein R 1 is H, CH 3 , C 2 to C 4 alkyl or C 6 to C 12 aryl; R 2 is H, OH, CN, CH 3 , C 2 to C 8 alkyl, or a halogen; and R 3 and R 4 are each independently H, CH 3 , C 2 to C 8 alkyl, C 6 to C 12 aryl, O—CH 3 , O—C 2 to C 8 alkyl, and O-aryl; (b) one or more latices formed from one or more halogenated polyolefins; and (c) one or more metal oxides.

2. The aqueous adhesive composition according to claim 1 , wherein the one or more film forming polymers are a halogenated olefin polymer.

3. The aqueous adhesive composition according to claim 1 , wherein the one or more film forming polymers are a halogenated substituted polydiene polymer.

4. The aqueous adhesive composition according to claim 1 , wherein the one or more lower crystallinity polynitroso compounds has a crystallinity of less than 30% by weight as determined by X-ray diffraction and the one or more higher crystallinity polynitroso compounds has crystallinity of greater than 40% by weight as determined by X-ray diffraction.

5. The aqueous adhesive composition according to claim 4 , wherein the one or more lower crystallinity polynitroso compounds and the one or more higher crystallinity polynitroso compounds are poly-(1,4-phenylyenazine-N,N-dioxide).

6. The aqueous adhesive composition according to claim 1 , wherein a weight ratio of the one or more lower crystallinity polynitroso compounds to the one or more higher crystallinity polynitroso compounds is 1:2 to 2:1.

7. The aqueous adhesive composition according to claim 1 , wherein the one or more bismaleimide-containing monomers are represented by the formula:

wherein R is a alkylene, cycloalkylene, heterocyclic, arylene, mixtures thereof.

8. The aqueous adhesive composition according to claim 1 , wherein the first aqueous composition comprises:

(i) 2 wt. % to 75 wt. %, based on the total weight of the first aqueous composition, of the one or more film forming polymers,

(ii) 2 wt. % to 30 wt. %, based on the total weight of the first aqueous composition, of the one or more lower crystallinity polynitroso compounds,

(iii) 3 wt. % to 30 wt. %, based on the total weight of the first aqueous composition, of the one or more higher crystallinity polynitroso compounds, and

(iv) 0.1 wt. % to 15 wt. %, based on the total weight of the first aqueous composition, of the one or more bismaleimide-containing monomers.

9. The aqueous adhesive composition according to claim 1 , wherein the polyacrylate is an alkali or ammonium salt of a polyacrylic acid and/or a substituted polyacrylic acid.

10. The aqueous adhesive composition according to claim 1 , wherein the one or more latices formed from one or more halogenated polyolefins comprises an emulsion copolymer of a chlorinated polyolefin with an ethylenically unsaturated monomer.

11. The aqueous adhesive composition according to claim 1 , wherein the second aqueous composition comprises:

(i) 2 wt. % to 30 wt. %, based on the total weight of the second aqueous composition, of the aqueous dispersion of at least one phenolic resin,

(ii) 5 wt. % to 40 wt. %, based on the total weight of the second aqueous composition, of the one or more latices formed from one or more halogenated polyolefins, and

(iii) 3 wt. % to 30 wt. %, based on the total weight of the second aqueous composition, of the one or more metal oxides.

12. The aqueous adhesive composition according to claim 1 , further comprising a surfactant and carbon black.

13. The aqueous adhesive composition according to claim 1 , wherein the first aqueous composition and second aqueous composition are admixed in a volume ratio of the first aqueous composition to the second aqueous composition of 10:0.5 to 0.5:10.

14. The aqueous adhesive composition according to claim 1 , having a Brookfield viscosity of from 10 to 1500 cPs at 20° C.

15. A bonded assembly comprising;

(a) a rigid substrate having an interfacial bond area,

(b) an unvulcanized rubber; and

(c) an aqueous adhesive composition bonding the rigid substrate to the unvulcanized rubber; wherein the aqueous adhesive composition comprises an admixture of:

(i) a first aqueous composition comprising, (1) one or more film forming polymers, (2) one or more lower crystallinity polynitroso compounds, (3) one or more higher crystallinity polynitroso compounds, and (4) one or more bismaleimide-containing monomers; and

(ii) a second aqueous composition comprising (1) an aqueous dispersion of at least one phenolic resin which is a condensation product of a phenol and formaldehyde, wherein the aqueous dispersion is stabilized by at least one polyacrylate derived from a monomer represented by Formula I:

wherein R 1 is H, CH 3 , C 2 to C 4 alkyl or C 6 to C 12 aryl; R 2 is H, OH, CN, CH 3 , C 2 to C 8 alkyl, or a halogen; and R 3 and R 4 are each independently H, CH 3 , C 2 to C 8 alkyl, C 6 to C 12 aryl, O—CH 3 , O—C 2 to C 8 alkyl, and O-aryl; (2) one or more latices formed from one or more halogenated polyolefins; and (3) one or more metal oxides.

16. The bonded assembly according to claim 15 , wherein the rigid substrate is steel.

17. The bonded assembly according to claim 15 , wherein the first aqueous composition and second aqueous composition are admixed in a volume ratio of the first aqueous composition to the second aqueous composition of 10:0.5 to 0.5:10.

18. The bonded assembly according to claim 15 , after heating the bonding assembly to a vulcanization temperature and under pressure for a time sufficient to vulcanize the unvulcanized rubber and the aqueous adhesive composition thereby bonding the rubber to the rigid substrate.

19. A method for bonding rubber to a rigid substrate, the method comprising:

(a) interposing an aqueous adhesive composition between at least a portion of a rigid substrate and an unvulcanized rubber to form an assemblage, wherein the aqueous adhesive composition comprises:

(i) a first aqueous composition comprising, (a) one or more film forming polymers, (2) one or more lower crystallinity polynitroso compounds, (3) one or more higher crystallinity polynitroso compounds, and (4) one or more bismaleimide-containing monomers; and

(ii) a second aqueous composition comprising (1) an aqueous dispersion of at least one phenolic resin which is a condensation product of a phenol and formaldehyde, wherein the aqueous dispersion is stabilized by at least one polyacrylate derived from a monomer represented by Formula I:

wherein R 1 is H, CH 3 , C 2 to C 4 alkyl or C 6 to C 12 aryl; R 2 is H, OH, CN, CH 3 , C 2 to C 8 alkyl, or a halogen; and R 3 and R 4 are each independently H, CH 3 , C 2 to C 8 alkyl, C 6 to C 12 aryl, O—CH 3 , O—C 2 to C 8 alkyl, and O-aryl; (2) one or more latices formed from one or more halogenated polyolefins; and (3) one or more metal oxides; and

(b) heating the assemblage to a vulcanization temperature and under pressure for a time sufficient to vulcanize the unvulcanized rubber and the aqueous adhesive composition thereby bonding the rubber to the rigid substrate.

20. The method according to claim 19 , wherein the first aqueous composition and second aqueous composition are admixed in a volume ratio of the first aqueous composition to the second aqueous composition of 10:0.5 to 0.5:10.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 16, 2021
From: DEHNICKE, STEFAN; BECKER, GERD; OSICHOW, ANNA; ZUTAVERN, PHILIPP; WESSLING, GERALD; KISTNER, DAVID
To: DOW PRODUKTIONS UND VERTRIEBS GMBH & CO. OHG
Reel/Frame 055264/0518 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 16, 2021
From: DOW PRODUCTIONS UND VERTRIEBS GMBH & CO. OHG
To: THE DOW CHEMICAL COMPANY
Reel/Frame 055264/0557 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 16, 2021
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 055264/0811 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 16, 2021
From: THE DOW CHEMICAL COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US, INC.
Reel/Frame 055305/0001 →
CHANGE OF NAME Recorded Feb 16, 2021
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC.
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
Reel/Frame 055305/0388 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 16, 2021
From: DOW GLOBAL TECHNOLOGIES LLC
To: THE DOW CHEMICAL COMPANY
Reel/Frame 055305/0395 →
Continuity (2)
Provisional Application 62661183 · Apr 23, 2018
Related Publication 20200407605A1 · Dec 31, 2020