US4565857A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Radiation-curable cellulose coating
Assignee: 3M Co
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Filing: 1984-11-21
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Granted: 1986-01-21
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Expires: 2004-11-21
Abstract
Abstract Ethylenically unsaturated cellulose esters are provided. These ethylenically unsaturated cellulose esters are the reaction product of a cellulose ester having unreacted hydroxyl groups and a polymerizable ethylenically unsaturated compound having an isocyanato group reactive with the hydroxyl groups of the cellulose ester. The product is substantially free of unreacted isocyanate groups and is particularly useful in protective coatings.
Inventors
- 👤 Richard J. Grant
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 17:11
CPC Classifications
C; C08; C08L; C08L1/00; C08L1/08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/81; C08G18/8108; C08B; C08B15/00; C08B15/05; C08B15/06; C08B3/00; C08B3/14; C08G18/28; C08G18/40; C08G18/64; C08G18/6484; C08G18/8141; C08G18/815; C08G18/8158; C08G18/8175
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
77 words
Ethylenically unsaturated cellulose ester comprising the reaction product of (a) a cellulose ester of cellulose and saturated aliphatic monocarboxylic acids having 2 to 4 carbon atoms or aromatic monocarboxylic acids, said cellulose ester having an average of about 0.1 to 2.0 unreacted hydroxyl groups per anhydroglucose unit, and (b) a polymerizable ethylenically unsaturated compound having an isocyanato group reactive with the hydroxyl groups of the cellulose ester, said reaction product being substantially free of unreacted isocyanate groups.
Claim 2
Dependent Claim
77 words
Ethylenically unsaturated cellulose ester comprising the reaction product of (a) a cellulose ester of cellulose and saturated aliphatic monocarboxylic acids having 2 to 4 carbon atoms or aromatic monocarboxylic acids, said cellulose ester having an average of about 0.1 to 2.0 unreacted hydroxyl groups per anhydroglucose unit, and (b) a polymerizable ethylenically unsaturated compound having an isocyanato group reactive with the hydroxyl groups of the cellulose ester, said reaction product being substantially free of unreacted isocyanate groups.
Claim 3
Dependent Claim
190 words
The ethylenically unsaturated cellulose ester of claim 1 having the formula [C.sub.6 H.sub.7 O.sub.2 (OR.sup.1).sub.x (OR.sup.2).sub.3-x ].sub.n wherein each R 1 is independently selected from hydrogen ##STR8## in which R is H or --CH 3 ; R 3 is an alkylene group having 2 to 12 carbon atoms; R 4 is a divalent organic group selected from linear and branched alkylene groups having 2 to 12 carbon atoms, cyclopentamethylene groups, cyclohexamethylene groups, phenylene groups, naphthalene groups, and phenylenemethylenephenylene groups; R 5 is a divalent organic group having 1 to 6 carbon atoms selected from saturated or unsaturated straight or branched aliphatic or cycloaliphatic groups or aromatic groups; each R 2 is independently selected from ##STR9## R 6 is a monovalent organic radical having 1 to 24 carbon atoms selected from saturated or unsaturated straight or branched aliphatic groups or aromatic groups; x is 0.1 to 2.0; n is a number of at least about 20 or larger, the various OR 1 and OR 2 groups are randomly distributed in the n sub units and said ethylenically unsaturated cellulose ester has an ethylenic unsaturation equivalent weight of less than about 1000.
Claim 4
Dependent Claim
66 words
The ethylenically unsaturated cellulose ester of claim 2 having the formula ##STR10## where R 6 is independently selected from --C 2 H 5 and --C 3 H 7 , and the sum of a and b is 3-x, and each of a and b are 0 to 2.9, and the a, b and c groups are randomly distributed in the n subunits of the cellulose ester.
Claim 5
Dependent Claim
38 words
The ethylenically unsaturated cellulose ester of claim 2 wherein said organic group R 4 is substituted by up to four lower alkyl groups having 1 to 4 carbon atoms and a total of up to 15 carbon atoms.
Claim 6
Dependent Claim
18 words
The ethylenically unsaturated cellulose ester of claim 1 having an unsaturated equivalent weight of less than about 500.
Claim 7
Dependent Claim
31 words
The ethylenically unsaturated cellulose ester of claim 1 wherein at least 30 percent of the hydroxyl groups of the cellulose ester (a) are reacted with the polymerizable ethylenically unsaturated compound (b).
Claim 8
Dependent Claim
24 words
The ethylenically unsaturated cellulose ester of claim 1 wherein cellulose ester (a) is selected from cellulose acetate, cellulose acetate propionate, and cellulose acetate butyrate.
Claim 9
Dependent Claim
23 words
The ethylenically unsaturated cellulose ester of claim 1 wherein polymerizable ethylenically unsaturated compound (b) is selected from isocyanatoethyl acrylate, isocyanatoethyl methacrylate, 2-(6-isocyanatohexylaminocarbonyloxy)ethyl acrylate.
Claim 10
Dependent Claim
20 words
A coating composition comprising a solution of the ethylenically unsaturated cellulose ester as defined in claim 1 in organic solvent.
Claim 11
Dependent Claim
25 words
The ethylenically unsaturated cellulose ester of claim 1 wherein cellulose ester (a) is cellulose acetate propionate and polymerizable ethylenically unsaturated compound (b) is isocyanatoethyl methacrylate.
Claim 12
Dependent Claim
17 words
The ethylenically unsaturated cellulose ester of claim 1 wherein polymerizable ethylenically unsaturated compound (b) is 2-(5-isocyanato-1,3,3-trimethylcyclohexylmethylaminocarbonyloxy)ethyl acrylate.
Claim 13
Dependent Claim
25 words
The ethylenically unsaturated cellulose ester of claim 1 wherein cellulose ester (a) is cellulose acetate propionate and polymerizable ethylenically unsaturated compound (b) is 2-(5-isocyanato-1,3,3-trimethylcyclohexylmethylaminocarbonyloxy)ethyl acrylate.
Claim 14
Dependent Claim
25 words
The ethylenically unsaturated cellulose ester of claim 1 wherein cellulose ester (a) is cellulose acetate propionate and polymerizable ethylenically unsaturated compound (b) is isocyanatoethyl acrylate.
Claim 15
Dependent Claim
24 words
The ethylenically unsaturated cellulose ester of claim 1 wherein cellulose ester (a) is cellulose acetate and polymerizable ethylenically unsaturated compound (b) is isocyanatoethyl methacrylate.
Claim 16
Dependent Claim
48 words
Ethylenically unsaturated cellulose ester comprising the reaction product of (a) a cellulose ester selected from cellulose acetate, cellulose acetate propionate and cellulose acetate butyrate and (b) a polymerizable ethylenically unsaturated compound selected from isocyanatoethyl acrylate and isocyanatoethyl methacrylate said reaction product being substantially free of unreacted isocyanate groups.
Claim 17
Dependent Claim
48 words
Ethylenically unsaturated cellulose ester comprising the reaction product of (a) a cellulose ester selected from cellulose acetate, cellulose acetate propionate and cellulose acetate butyrate and (b) a polymerizable ethylenically unsaturated compound selected from isocyanatoethyl acrylate and isocyanatoethyl methacrylate said reaction product being substantially free of unreacted isocyanate groups.
Claim 18
Dependent Claim
12 words
A coating composition as claimed in claim 15 further comprising a photoinitiator.
Claim 19
Dependent Claim
12 words
A substrate having a cured coating of the composition of claim 5.
Claim 20
Dependent Claim
31 words
A substrate having a coating comprising the polymerized product of claim 15 wherein said coating has a solvent resistance of at least 400 rubs with a cotton swab saturated with acetone.
References Cited (Backward Citations)
GB656643A
Cited
US2647884A
Cited
US2821544A
Cited
US3311608A
Cited
US3475356A
Cited
US3782950A
Cited
US3749592A
Cited
JPS5048091A
Cited
US4066828A
Cited
US4147603A
Cited
US4112182A
Cited
JPS5443299A
Cited
US4233425A
Cited
US4407855A
Cited
US4404347A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-01-20 | 1989-07-22 | 1990-01-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-01-20 | 1993-07-22 | 1994-01-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-01-20 | 1997-07-22 | 1998-01-21 | $7700.00 | Window Closed / Lapsed |