US4557979A
Expired / Lapsed
US
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Process for deposition of resin dispersions on metal substrates
Assignee: Monsanto Co
•
Filing: 1984-02-17
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Granted: 1985-12-10
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Expires: 2004-02-17
Abstract
Abstract Coating of a resin blend on a metal substrate by electrodeposition wherein the resin blend comprises a poly(3,4-dihydro-3-substituted-1,3-benzoxazine) and a reactive polyamine. The resin blend is dispersed in an aqueous medium containing a protonating acid and is subjected to cathodic electrophoresis to deposit the blend on a metal substrate as an adherent film which is dried and cured by the application of heat. The resin blend cures at relatively low temperatures without evolution of volatile matter.
Inventors
- 👤 Harold P. Higginbottom
- 👤 Manuel F. Drumm
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:19
CPC Classifications
C; C09; C09D; C09D5/00; C09D5/44; C09D5/4488; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31678; Y10T428/31688
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
197 words
A process for the deposition of a film of a blend of a poly(3,4-dihydro-3-substituted-1,3-benzoxazine) and a reactive polyamine on a metal substrate which comprises forming a dispersion of the polydihydrobenzoxazine and the reactive polyamine in an aqueous medium containing a protonating acid, forming an electrolytic cell using the metal substrate as the cathode of the cell and the aqueous dispersion as the electrolyte, and subjecting the aqueous dispersion to electrophoresis whereby to deposit the blend of the polydihydrobenzoxazine and the reactive polyamine on the metal substrate as an adherent film, wherein the poly(dihydrobenzoxazine) is of number average molecular weight in the range of about 250 to about 2000, with the majority of the individual molecules containing at least two dihydrobenzoxazine groups, and is the reaction product of about 1 equivalent of a primary amine selected from the group consisting of mono- and poly-primary amines, about 1 equivalent of a phenol selected from the group consisting of mono- and poly-phenols having phenolic hydroxy groups with at least one unsubstituted position ortho to such hydroxy groups and about 2 equivalents of formaldehyde, and wherein the reactive polyamine is at least difunctional, the reactive groups being primary or secondary amine.
Claim 2
Dependent Claim
197 words
A process for the deposition of a film of a blend of a poly(3,4-dihydro-3-substituted-1,3-benzoxazine) and a reactive polyamine on a metal substrate which comprises forming a dispersion of the polydihydrobenzoxazine and the reactive polyamine in an aqueous medium containing a protonating acid, forming an electrolytic cell using the metal substrate as the cathode of the cell and the aqueous dispersion as the electrolyte, and subjecting the aqueous dispersion to electrophoresis whereby to deposit the blend of the polydihydrobenzoxazine and the reactive polyamine on the metal substrate as an adherent film, wherein the poly(dihydrobenzoxazine) is of number average molecular weight in the range of about 250 to about 2000, with the majority of the individual molecules containing at least two dihydrobenzoxazine groups, and is the reaction product of about 1 equivalent of a primary amine selected from the group consisting of mono- and poly-primary amines, about 1 equivalent of a phenol selected from the group consisting of mono- and poly-phenols having phenolic hydroxy groups with at least one unsubstituted position ortho to such hydroxy groups and about 2 equivalents of formaldehyde, and wherein the reactive polyamine is at least difunctional, the reactive groups being primary or secondary amine.
Claim 3
Dependent Claim
21 words
The process of claim 1 wherein the dispersion contains about 0.2 to 2.0 equivalents of dihydrobenzoxazine per equivalent of reactive polyamine.
Claim 4
Dependent Claim
40 words
The process of claim 2 wherein the reactive polyamine is of number average molecular weight in the range of about 500 to about 15,000 and has a reactive amine equivalent weight in the range of about 250 to about 1500.
Claim 5
Dependent Claim
26 words
The process of claim 1 wherein the primary amine reactant for the production of the poly(dihydrobenzoxazine) is an amine of pK b less than about 7.
Claim 6
Dependent Claim
26 words
The process of claim 1 wherein the primary amine reactant for the production of the poly(dihydrobenzoxazine) is an amine of pK b at least about 7.
Claim 7
Dependent Claim
22 words
The process of claim 5 wherein the primary amine reactant is a C 6 to C 40 unsubstituted or substituted aromatic amine.
Claim 8
Dependent Claim
24 words
The process of claim 4 wherein the primary amine reactant is a C 1 to C 40 unsubstituted or unsubstituted aliphatic amine or hydrazine.
Claim 9
Dependent Claim
28 words
The process of claim 1 wherein the dispersion contains at least about 1 equivalent of protonating acid for each equivalent of reactive amine group in the reactive polyamine.
Claim 10
Dependent Claim
13 words
The process of claim 1 wherein the protonating acid is a carboxy acid.
Claim 11
Dependent Claim
18 words
The process of claim 1 wherein the protonating acid is a C 1 to C 4 carboxy acid.
Claim 12
Dependent Claim
16 words
The process of claim 1 wherein the electrodeposited film is dried and heated to effect cure.
Claim 13
Dependent Claim
98 words
The process of claim 4 wherein the phenol reactant for the production of the poly(dihydrobenzoxazine) is selected from the group consisting of C 6 to C 30 phenols, alkyl substituted C 6 to C 30 phenols, alkoxy substituted C 6 to C 30 phenols, arylsubstituted C 6 to C 30 phenols, halo substituted C 6 to C 30 phenols, C 6 to C 70 polyphenols, alkyl substituted C 6 to C 70 polyphenols, alkoxy substituted C 6 to C 70 polyphenols, aryl substituted C 6 to C 70 polyphenols and halo substituted C 6 to C 70 polyphenols.
Claim 14
Dependent Claim
98 words
The process of claim 5 wherein the phenol reactant for the production of the poly(dihydrobenzoxazine) is selected from the group consisting of C 6 to C 30 phenols, alkyl substituted C 6 to C 30 phenols, alkoxy substituted C 6 to C 30 phenols, arylsubstituted C 6 to C 30 phenols, halo substituted C 6 to C 30 phenols, C 6 to C 70 polyphenols, alkyl substituted C 6 to C 70 polyphenol,s alkoxy substituted C 6 to C 70 polyphenols, aryl substituted C 6 to C 70 polyphenols and halo substituted C 6 to C 70 polyphenols.
Claim 15
Dependent Claim
196 words
A process for the deposition of a film of a blend of a poly(3,4-dihydro-3-substituted-1,3-benzoxazine) and a reactive polyamine on a metal substrate which comprises forming a dispersion of the polydihydrobenzoxazine and the reactive polyamine in an aqueous medium containing a protonating acid, forming an electrolytic cell using the metal substrate as the cathode of the cell and the aqueous dispersion as the electrolyte, and subjecting the aqueous dispersion to electrophoresis whereby to deposit the blend of the polydihydrobenzoxazine and the reactive polyamine on the metal substrate as an adherent film, wherein the poly(dihydrobenzoxazine) is the reaction product of about 1 equivalent of a weak base amine of pK b of about 7 or greater, about 1 equivalent of a polyphenol selected from the group consisting of C 6 to C 70 polyphenols, alkyl substituted C 6 to C 70 polyphenols, alkoxy substituted C 6 to C 70 polyphenols, aryl substituted C 6 to C 70 polyphenols and halo substituted C 6 to C 70 polyphenols and about 2 equivalents of formaldehyde, and wherein the protonated reactive polyamine is at least difunctional, its reactive groups being primary or secondary amine of pK b less than about 5.
Claim 16
Dependent Claim
196 words
A process for the deposition of a film of a blend of a poly(3,4-dihydro-3-substituted-1,3-benzoxazine) and a reactive polyamine on a metal substrate which comprises forming a dispersion of the polydihydrobenzoxazine and the reactive polyamine in an aqueous medium containing a protonating acid, forming an electrolytic cell using the metal substrate as the cathode of the cell and the aqueous dispersion as the electrolyte, and subjecting the aqueous dispersion to electrophoresis whereby to deposit the blend of the polydihydrobenzoxazine and the reactive polyamine on the metal substrate as an adherent film, wherein the poly(dihydrobenzoxazine) is the reaction product of about 1 equivalent of a weak base amine of pK b of about 7 or greater, about 1 equivalent of a polyphenol selected from the group consisting of C 6 to C 70 polyphenols, alkyl substituted C 6 to C 70 polyphenols, alkoxy substituted C 6 to C 70 polyphenols, aryl substituted C 6 to C 70 polyphenols and halo substituted C 6 to C 70 polyphenols and about 2 equivalents of formaldehyde, and wherein the protonated reactive polyamine is at least difunctional, its reactive groups being primary or secondary amine of pK b less than about 5.
Claim 17
Dependent Claim
33 words
The process of claim 14 wherein the C 6 to C 70 polyphenol is selected from the group consisting of hydroquinone, bisphenol A, bis(4-hydroxy-phenyl)-methane, 4-hydroxyphenyl ether, 4-hydroxyphenyl sulfone, and 4,4'-bisphenol and novolac oligomers.
Claim 18
Dependent Claim
28 words
The process of claim 14 wherein the dispersion contains at least about 1 equivalent of protonating acid for each equivalent of reactive amine group in the reactive polyamine.
Claim 19
Dependent Claim
13 words
The process of claim 14 wherein the protonating acid is a carboxy acid.
Claim 20
Dependent Claim
18 words
The process of claim 14 wherein the protonating acid is a C 1 to C 4 carboxy acid.
Claim 21
Dependent Claim
16 words
The process of claim 15 wherein the electrodeposited film is dried and heated to effect cure.
Claim 22
Dependent Claim
10 words
A metal substrate electrocoated by the process of claim 1.
Claim 23
Dependent Claim
10 words
A metal substrate electrocoated by the process of claim 2.
Claim 24
Dependent Claim
10 words
A metal substrate electrocoated by the process of claim 3.
Claim 25
Dependent Claim
10 words
A metal substrate electrocoated by the process of claim 14.
Claim 26
Dependent Claim
10 words
A metal substrate electrocoated by the process of claim 17.
Claim 27
Dependent Claim
10 words
A metal substrate electrocoated by the process of claim 18.
Claim 28
Dependent Claim
10 words
A metal substrate electrocoated with the dispersion of claim 1.
Claim 29
Dependent Claim
10 words
A metal substrate electrocoated with the dispersion of claim 2.
Claim 30
Dependent Claim
10 words
A metal substrate electrocoated with the dispersion of claim 3.
Claim 31
Dependent Claim
10 words
A metal substrate electrocoated with the dispersion of claim 14.
Claim 32
Dependent Claim
10 words
A metal substrate electrocoated with the dispersion of claim 17.
Claim 33
Dependent Claim
10 words
A metal substrate electrocoated with the dispersion of claim 18.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-12-09 | 1989-06-10 | 1989-12-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-09 | 1993-06-10 | 1993-12-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-09 | 1997-06-10 | 1997-12-10 | $7700.00 | Window Closed / Lapsed |