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US4565857A Expired / Lapsed US ⏱️ 0.0 years remaining

Radiation-curable cellulose coating

Assignee: 3M Co
•
Filing: 1984-11-21
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Granted: 1986-01-21
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Expires: 2004-11-21
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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 19:06
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.

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

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