Patent US4777276A successfully refreshed from Google Patents.
US4777276A
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US
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Acrylamidoacylated oligomers
Assignee: 3M Co
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Filing: 1981-10-29
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Granted: 1988-10-11
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Expires: 2001-10-29
Abstract
Abstract A composition of matter comprising an acrylamido-acyl or methacrylamido-acyl oligomer derived from at least one nucleophilic oligomer having at least one amino-, hydroxyl-, or thiol-substituted polyoxyalkylene, polyalkyleneimine, polyester, polyolefin, polyacrylate, or polysiloxane oligomer, said nucleophilic oliogmer having a molecular weight in the range of 200 to 20,000 is disclosed. Also disclosed are free radically polymerizable monomer-containing compositions containing said oligomers as well as acrylamido- and methacrylamido-acylated polymers which are the thermal or photocured products of said oligomers. In addition, a process is disclosed for providing said acrylamido- and methacrylamido-acylated oligomers which are useful, for example, in coatings, films, printing inks, adhesives, and saturants.
Inventors
- 👤 Jerald K. Rasmussen
- 👤 Steven M. Heilmann
- 👤 Frederick J. Palensky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 17:27
CPC Classifications
C; C09; C09D; C09D4/00; C08; C08F; C08F299/00; C08F299/02; C08F299/022; C08F299/024; C09J; C09J4/00
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
261 words
An acrylamido- or methacrylamido-acyl oligomer having the general formula: A.sub.p (HX).sub.n-p R wherein R is an organic group having a valence of n and is the residue of a nucleophilic group-substituted oligomer, (HX) n R, the oligomer being selected from polyoxyalkylene, polyalkyleneimine, and polyolefin oligomers having one or more hydroxyl, amino, or thiol groups and having a molecular weight of 200 to 20,000; n is a positive number of at least one and represents the valence of R; p is a positive number between 1 and n; A is an acrylamido-acyl group or a methacrylamido-acyl group having the formula ##STR9## wherein R 1 is hydrogen, chlorine, or a methyl group; R 2 is a single bond or a methylene or ethylene group that can be substituted by an alkyl group having 1 to 6 carbon atoms or phenyl; R 3 and R 4 are independently hydrogen, an alkyl or cycloalkyl group having 1 to 12 carbon atoms, phenyl or alkyl-substituted phenyl having 6 to 12 carbon atoms, or R 3 and R 4 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; and X is ##STR10## in which R 5 is (a) hydrogen, (b) a group selected from an alkyl or cycloalkyl group having 1 to 12 carbon atoms optionally substituted by a cyano, hydroxyl, or an alkoxy group having 1 to 4 carbon atoms, or A; with the proviso that when R 5 is an alkyl or cycloalkyl group, then at least one of R 3 and R 4 is hydrogen.
Claim 2
Dependent Claim
261 words
An acrylamido- or methacrylamido-acyl oligomer having the general formula: A.sub.p (HX).sub.n-p R wherein R is an organic group having a valence of n and is the residue of a nucleophilic group-substituted oligomer, (HX) n R, the oligomer being selected from polyoxyalkylene, polyalkyleneimine, and polyolefin oligomers having one or more hydroxyl, amino, or thiol groups and having a molecular weight of 200 to 20,000; n is a positive number of at least one and represents the valence of R; p is a positive number between 1 and n; A is an acrylamido-acyl group or a methacrylamido-acyl group having the formula ##STR9## wherein R 1 is hydrogen, chlorine, or a methyl group; R 2 is a single bond or a methylene or ethylene group that can be substituted by an alkyl group having 1 to 6 carbon atoms or phenyl; R 3 and R 4 are independently hydrogen, an alkyl or cycloalkyl group having 1 to 12 carbon atoms, phenyl or alkyl-substituted phenyl having 6 to 12 carbon atoms, or R 3 and R 4 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; and X is ##STR10## in which R 5 is (a) hydrogen, (b) a group selected from an alkyl or cycloalkyl group having 1 to 12 carbon atoms optionally substituted by a cyano, hydroxyl, or an alkoxy group having 1 to 4 carbon atoms, or A; with the proviso that when R 5 is an alkyl or cycloalkyl group, then at least one of R 3 and R 4 is hydrogen.
Claim 3
Dependent Claim
17 words
The oligomer according to claim 1 wherein R 2 of the oligomer formula is a single bond.
Claim 4
Dependent Claim
30 words
The oligomer according to claim 1 wherein both R 3 and R 4 of the oligomer formula independently represent an alkyl or cycloalkyl group of 1 to 12 carbon atoms.
Claim 5
Dependent Claim
43 words
The oligomer according to claim 1 wherein R 1 is hydrogen, R 3 and R 4 are each a methyl group, X is selected from --O-- and --NH, and R is the residue iof polyoxyalkylene oligomer having one or more primary amino groups.
Claim 6
Dependent Claim
17 words
The oligomer according to claim 1 which is the reaction product of a polyoxypropylenediamine oligomer and 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one.
Claim 7
Dependent Claim
16 words
The oligomer according to claim 1 which the reaction product of a polyoxyethylenediamine oligomer and 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one.
Claim 8
Dependent Claim
17 words
The oligomer according to claim 1 which is the reaction product of a polytetramethyleneoxidediamine oligomer and 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one.
Claim 9
Dependent Claim
17 words
The oligomer according to claim 1 which is the reaction product of a polyoxypropylenediamine oligomer and 2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one.
Claim 10
Dependent Claim
17 words
The oligomer according to claim 1 which is the reaction product of a polyoxypropylenediamine oligomer and 2-ethenyl-4,5-dihydro-4H-1,3-oxazin-6-one.
Claim 11
Dependent Claim
19 words
The oligomer according to claim 1 which is the reaction product of a polyethylene oxide monomethylether oligomer and 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one.
Claim 12
Dependent Claim
54 words
An oligomer which is the reaction product of a polycaprolactonediol oligomer and 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one, said oligomer having the formula A.sub.p (HX).sub.n-p R wherein A is ##STR11## R is an organic group having a valence of 2 and is the residue of a polycaprolactonediol oligomer, n is equal to 2, and p is equal to 2.
Claim 13
Dependent Claim
54 words
An oligomer which is the reaction product of a polycaprolactonediol oligomer and 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one, said oligomer having the formula A.sub.p (HX).sub.n-p R wherein A is ##STR11## R is an organic group having a valence of 2 and is the residue of a polycaprolactonediol oligomer, n is equal to 2, and p is equal to 2.
Claim 14
Dependent Claim
258 words
An acrylamido- or methacrylamido-acyl oligomer having the general formula: A.sub.p (HX).sub.n-p R wherein R is an organic group having a valence of n and is the residue of a nucleophilic group-substituted oligomer, (HX) n R, said oligomer being an organic polyester oligomer having one or more hydroxyl, amino, or thiol groups and having a molecular weight of 200 to 20,000; n is a positive number of at least one and represents the valence of R; p is a positive number between 1 and n; A is an acrylamido-acyl group or a methacrylamido-acyl group having the formula ##STR12## wherein R 1 is hydrogen, chlorine, or a methyl group; R 2 is a single bond or a methylene or ethylene group that can be substituted by an alkyl group haivng 1 to 6 carbon atoms or phenyl; R 3 or R 4 are independently hydrogen, an alkyl or cycloalkyl group having 1 to 12 carbon atoms, phenyl or alkyl-substituted phenyl having 6 to 12 carbon atoms, or R 3 and R 4 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; and X is ##STR13## in which R 5 is (a) hydrogen, (b) a group selected from an alkyl or cycloalkyl group having 1 to 12 carbon atoms optionally substituted by a cyano, hydroxyl, or an alkoxy group having 1 to 4 carbon atoms, or A; with the proviso that when R 5 is an alkyl or cycloalkyl group, then at least one of R 3 and R 4 is hydrogen.
Claim 15
Dependent Claim
258 words
An acrylamido- or methacrylamido-acyl oligomer having the general formula: A.sub.p (HX).sub.n-p R wherein R is an organic group having a valence of n and is the residue of a nucleophilic group-substituted oligomer, (HX) n R, said oligomer being an organic polyester oligomer having one or more hydroxyl, amino, or thiol groups and having a molecular weight of 200 to 20,000; n is a positive number of at least one and represents the valence of R; p is a positive number between 1 and n; A is an acrylamido-acyl group or a methacrylamido-acyl group having the formula ##STR12## wherein R 1 is hydrogen, chlorine, or a methyl group; R 2 is a single bond or a methylene or ethylene group that can be substituted by an alkyl group haivng 1 to 6 carbon atoms or phenyl; R 3 or R 4 are independently hydrogen, an alkyl or cycloalkyl group having 1 to 12 carbon atoms, phenyl or alkyl-substituted phenyl having 6 to 12 carbon atoms, or R 3 and R 4 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; and X is ##STR13## in which R 5 is (a) hydrogen, (b) a group selected from an alkyl or cycloalkyl group having 1 to 12 carbon atoms optionally substituted by a cyano, hydroxyl, or an alkoxy group having 1 to 4 carbon atoms, or A; with the proviso that when R 5 is an alkyl or cycloalkyl group, then at least one of R 3 and R 4 is hydrogen.
Claim 16
Dependent Claim
257 words
An acrylamido- or methacrylamido-acyl oligomer having the general formula: A.sub.p (HX).sub.n-p R wherein R is an organic group having a valence of n and is the residue of a nucleophilic group-substituted oligomer, (HX) n R, said oligomer being a polysiloxane oligomer having one or more hydroxyl, amino, or thiol groups and having a molecular weight of 200 to 20,000; n is a positive number of at least one and represents the valence of R; p is a positive number between 1 and n; A is an acrylamido-acyl group or a methylacrylamido-acyl group having the formula ##STR14## wherein R 1 is hydrogen, chlorine, or a methyl group; R 2 is a single bond or a methylene or ethylene group that can be substituted by an alkyl group having 1 to 6 carbon atoms or phenyl; R 3 and R 4 are independently hydrogen, an alkyl or cycloalkyl group having 1 to 12 carbon atoms, phenyl or alkyl-substituted phenyl having 6 to 12 carbon atoms, or R 3 and R 4 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; and X is ##STR15## in which R 5 is (a) hydrogen, (b) a group selected from an alkyl or cycloalkyl group having 1 to 12 carbon atoms optionally substituted by a cyano, hydroxyl, or an alkoxy group having 1 to 4 carbon atoms, or A; wherein the proviso that when R 5 is an alkyl or cycloalkyl group, then at least one of R 3 and R 4 is hydrogen.
Claim 17
Dependent Claim
257 words
An acrylamido- or methacrylamido-acyl oligomer having the general formula: A.sub.p (HX).sub.n-p R wherein R is an organic group having a valence of n and is the residue of a nucleophilic group-substituted oligomer, (HX) n R, said oligomer being a polysiloxane oligomer having one or more hydroxyl, amino, or thiol groups and having a molecular weight of 200 to 20,000; n is a positive number of at least one and represents the valence of R; p is a positive number between 1 and n; A is an acrylamido-acyl group or a methylacrylamido-acyl group having the formula ##STR14## wherein R 1 is hydrogen, chlorine, or a methyl group; R 2 is a single bond or a methylene or ethylene group that can be substituted by an alkyl group having 1 to 6 carbon atoms or phenyl; R 3 and R 4 are independently hydrogen, an alkyl or cycloalkyl group having 1 to 12 carbon atoms, phenyl or alkyl-substituted phenyl having 6 to 12 carbon atoms, or R 3 and R 4 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; and X is ##STR15## in which R 5 is (a) hydrogen, (b) a group selected from an alkyl or cycloalkyl group having 1 to 12 carbon atoms optionally substituted by a cyano, hydroxyl, or an alkoxy group having 1 to 4 carbon atoms, or A; wherein the proviso that when R 5 is an alkyl or cycloalkyl group, then at least one of R 3 and R 4 is hydrogen.
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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) | 1991-10-11 | 1992-04-11 | 1992-10-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-10-11 | 1996-04-11 | 1996-10-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-10-11 | 2000-04-11 | 2000-10-11 | $7700.00 | Window Closed / Lapsed |