US4180598A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Radiation-curable coating compositions and method of coating metal substrates therewith
Assignee: Rohm and Haas Co
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Filing: 1978-08-11
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Granted: 1979-12-25
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Expires: 1998-08-11
Abstract
Abstract The present invention is concerned with improvement in coating compositions that are curable by actinic radiation, such as ultraviolet, electron beam, or mercury arc radiation, and especially those that are rapidly cured at ambient temperature conditions while subjected to radiation in the ultraviolet wave length range from about 2,000 to about 5,000 Angstroms or longer. β-acryloxypropionic acid is added to such compositions as part or all of the reactive diluent in the radiation curable compositions to impart improved adhesion of the cured coating to many substrates, especially to bare metals, such as aluminum, steel, copper, zinc, etc.
Inventors
- 👤 William D. Emmons
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 15:48
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/085; C; C09; C09D; C09D4/00; C09D4/06
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
85 words
A readiation-curable composition, characterized by improved adhesion to metal substrates, having a film-forming binder consisting essentially of: (A) At least one ethylenically unsaturated monomer selected from the group consisting of isobornyl acrylate, 2-ethylhexyl acrylate, ethoxyethoxyethyl acrylate, dicyclopentenyloxyethyl acrylate and dicyclopentenyloxyethyl methacrylate, and (B) At least one acrylated oligomeric condensation or addition product having at least two terminal or pendant acryloxy groups of the formula H.sub.2 C═C(H)C(O)O--, and about 1% to 15% by weight, based on the total weight of (A) and (B), of 3-acryloxypropionic acid.
Claim 2
Dependent Claim
85 words
A readiation-curable composition, characterized by improved adhesion to metal substrates, having a film-forming binder consisting essentially of: (A) At least one ethylenically unsaturated monomer selected from the group consisting of isobornyl acrylate, 2-ethylhexyl acrylate, ethoxyethoxyethyl acrylate, dicyclopentenyloxyethyl acrylate and dicyclopentenyloxyethyl methacrylate, and (B) At least one acrylated oligomeric condensation or addition product having at least two terminal or pendant acryloxy groups of the formula H.sub.2 C═C(H)C(O)O--, and about 1% to 15% by weight, based on the total weight of (A) and (B), of 3-acryloxypropionic acid.
Claim 3
Dependent Claim
27 words
A composition according to claim 1 further comprising a photosensitizer in a small but effective amount, and optionally an amine activator in a small but effective amount.
Claim 4
Dependent Claim
18 words
A composition according to claim 1 or 2 in which the oligomer is an acrylated epoxidized soybean oil.
Claim 5
Dependent Claim
13 words
A composition according to claim 3 in which component (A) comprises isobornyl acrylate.
Claim 6
Dependent Claim
13 words
A composition according to claim 3 in which component (A) comprises dicyclopentenyloxyethyl methacrylate.
Claim 7
Dependent Claim
13 words
A composition according to claim 3 in which component (A) comprises dicyclopentenyloxyethyl acrylate.
Claim 8
Dependent Claim
13 words
A composition according to claim 3 in which component (A) comprises 2-ethylhexyl acrylate.
Claim 9
Dependent Claim
13 words
A composition according to claim 3 in which component (A) comprises ethoxyethoxyethyl acrylate.
Claim 10
Dependent Claim
68 words
In a radiation-curable coating composition having a film-forming binder comprising unsaturated monomeric and oligomeric components (A) and (B), as defined in claim 1, the improvement which consists in the incorporation therein of about 2 to 8 weight percent, based on the total weight of (A) and (B), of 3-acryloxypropionic acid to improve the adhesion of the cured coating to metal substrates on which they are cured by radiation.
Claim 11
Dependent Claim
49 words
A method for coating a metal substrate, which comprises preparing a radiation-curable composition as defined in claim 1, applying a thin film of the composition to the surface of a substrate, and then subjecting the film to actinic radiation for a length of time sufficient to cure the film.
Claim 12
Dependent Claim
42 words
A composition according to claim 1 wherein the weight ratio of (A) to (B) is from 10:90 to 90:10 and the amount of 3-acryloxypropionic acid is from about 2 to 8% by weight, based on the total weight of (A) and (B).
Claim 13
Dependent Claim
12 words
A composition according to claim 11 which is a 100% solids composition.
Claim 14
Dependent Claim
32 words
A composition according to claim 12 wherein the component (A) consists essentially of at least 1 monomer selected from the group consisting of isobornyl acrylate, ethoxyethoxyethyl acrylate, dicyclopentenyloxyethyl acrylate, and dicyclopentenyloxyethyl methacrylate.
Claim 15
Dependent Claim
13 words
A composition according to claim 12 wherein (A) consists essentially of isobornyl acrylate.
Claim 16
Dependent Claim
13 words
A composition according to claim 12 wherein (A) consists essentially of dicyclopentenyloxyethyl acrylate.
Claim 17
Dependent Claim
33 words
A composition according to claim 11 wherein the composition may comprise a photosensitizer in an effective amount of at least 0.1% by weight of the total weight of (A), (B), and 3-acryloxypropionic acid.
Claim 18
Dependent Claim
15 words
A method according to claim 10 wherein the radiation is effected by an electron beam.
Claim 19
Dependent Claim
48 words
A method for coating a metal substrate which comprises preparing a radiation-curable composition according to claim 11, applying a thin film of the composition to the surface of the metal, and then subjecting the film to actinic radiation for a length of time sufficent to cure the film.
Claim 20
Dependent Claim
20 words
A method according to claim 18 wherein the radiation-curable composition is a 100% solids composition as defined in claim 14.
Claim 21
Dependent Claim
16 words
A method according to claim 19 in which the radiation is that of an electron beam.
Claim 22
Dependent Claim
33 words
A method according to claim 19 in which the radiation is effected by light having a wave length or a band of wave lengths in the range of about 2,000 to 5,000 Angstroms.
Claim 23
Dependent Claim
33 words
A composition according to claim 1 or 11 wherein the acrylated oligomeric product is a poly(meth)acrylate obtained by the reaction of (meth)acrylic acid by addition to epoxy groups of a bisphenol-based epoxy resin.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-24 | 1983-06-25 | 1983-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-24 | 1987-06-25 | 1987-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-24 | 1991-06-25 | 1991-12-25 | $7700.00 | Window Closed / Lapsed |