US4619867A
Expired / Lapsed
US
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Azlactone-containing pressure-sensitive adhesives
Assignee: 3M Co
•
Filing: 1984-11-28
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Granted: 1986-10-28
•
Expires: 2004-11-28
Abstract
Abstract Pressure-sensitive adhesives are prepared by the simultaneous polymerization of minor amounts of at least one alkenyl azlactone monomer and at least one arylic-functional carboxylic acid monomer, or precursors thereof, with a major amount of at least one acrylic monomer. The pressure-sensitive adhesives, after application to a substrate, will significantly increase in adhesion to the resultant bonded substrate after they are in the bonded configuration.
Inventors
- 👤 Robert R. Charbonneau
- 👤 Steven M. Heilmann
- 👤 Jerald K. Rasmussen
- 👤 Michael L. Tumey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 21:14
CPC Classifications
C; C09; C09J; C09J133/00; C09J133/04; C09J133/06; C09J133/08; C09J2301/00; C09J2301/30; C09J2301/302; Y; Y10; Y10T; Y10T428/00; Y10T428/28; Y10T428/2852; Y10T428/2878; Y10T428/2887; Y10T428/2891
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
335 words
A pressure-sensitive adhesive tape comprising (a) a tape backing, and (b) coated on at least one surface thereof a pressure-sensitive, normally-tacky, adhesive interpolymer which is the product of simultaneous polymerization of ethylenically-unsaturated monomers which comprise (1) from about 70 to 90 molar parts of monomers consisting of (a) 69-100 mole percent of an acrylic acid ester of at least one non-tertiary alkyl alcohol, the molecules of said alcohol containing 1-14 carbon atoms, the average being 5-12 carbon atoms, (b) 31-0 mole percent of at least one monomer selected from the group consisting of vinyl acetate, styrene, vinyl ethers, and alkyl methacrylates, the alkyl group having 1 to 14 carbon atoms, and (c) 10-0 mole percent of at least one monomer selected from the group consisting of acrylamide, methacrylamide, acrylonitrile, methacrylonitrile, and N-vinyl pyrrolidone, and (2) from 25 to 5 molar parts of at least one alkenyl azlactone monomer having the formula I ##STR6## where R 1 is hydrogen or methyl; R 2 is selected from a single bond, --R 3 --, or ##STR7## in which R 3 is a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, and W is --O--, --S--, or --NH--; R 4 and R 7 are independently selected from a single bond, methylene, or substituted methylene having 1 to 12 carbon atoms; R 5 and R 6 are independently substituted or unsubstituted alkyl or cycloalkyl having 1 to 12 carbon atoms, aryl or aralkyl having 6 to 12 carbon atoms, or R 5 and R 6 taken together with the carbon to which they are joined forming a 5- or 6-membered carbocyclic ring or R 5 and R 6 each may be hydrogen when at least one of R 4 and R 7 is methylene; and (3) from 25 to 5 molar parts of at least one acrylic-functional carboxylic acid monomer selected from acrylic acid, methacrylic acid, itaconic acid, maleic acid, or an N-acryloylamino acid; said interpolymer exhibiting a glass transition temperature (Tg) of less than -15° C.
Claim 2
Dependent Claim
335 words
A pressure-sensitive adhesive tape comprising (a) a tape backing, and (b) coated on at least one surface thereof a pressure-sensitive, normally-tacky, adhesive interpolymer which is the product of simultaneous polymerization of ethylenically-unsaturated monomers which comprise (1) from about 70 to 90 molar parts of monomers consisting of (a) 69-100 mole percent of an acrylic acid ester of at least one non-tertiary alkyl alcohol, the molecules of said alcohol containing 1-14 carbon atoms, the average being 5-12 carbon atoms, (b) 31-0 mole percent of at least one monomer selected from the group consisting of vinyl acetate, styrene, vinyl ethers, and alkyl methacrylates, the alkyl group having 1 to 14 carbon atoms, and (c) 10-0 mole percent of at least one monomer selected from the group consisting of acrylamide, methacrylamide, acrylonitrile, methacrylonitrile, and N-vinyl pyrrolidone, and (2) from 25 to 5 molar parts of at least one alkenyl azlactone monomer having the formula I ##STR6## where R 1 is hydrogen or methyl; R 2 is selected from a single bond, --R 3 --, or ##STR7## in which R 3 is a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, and W is --O--, --S--, or --NH--; R 4 and R 7 are independently selected from a single bond, methylene, or substituted methylene having 1 to 12 carbon atoms; R 5 and R 6 are independently substituted or unsubstituted alkyl or cycloalkyl having 1 to 12 carbon atoms, aryl or aralkyl having 6 to 12 carbon atoms, or R 5 and R 6 taken together with the carbon to which they are joined forming a 5- or 6-membered carbocyclic ring or R 5 and R 6 each may be hydrogen when at least one of R 4 and R 7 is methylene; and (3) from 25 to 5 molar parts of at least one acrylic-functional carboxylic acid monomer selected from acrylic acid, methacrylic acid, itaconic acid, maleic acid, or an N-acryloylamino acid; said interpolymer exhibiting a glass transition temperature (Tg) of less than -15° C.
Claim 3
Dependent Claim
29 words
The pressure-sensitive adhesive tape according to claim 1 wherein said ethylenically-unsaturated monomer of component (1) (a) of said interpolymer is an acrylic acid ester derived from an 8-carbon alcohol.
Claim 4
Dependent Claim
38 words
The pressure-sensitive adhesive tape according to claim 1 wherein said monomer component of said interpolymer is selected from the group consisting of (1) (a) components 2-ethylhexyl acrylate, iso-octyl acrylate, and 2-methylbutyl acrylate, and (1) (b) component lauryl methacrylate.
Claim 5
Dependent Claim
28 words
The pressure-sensitive adhesive tape according to claim 1 wherein said alkenyl azlactone monomer component of said interpolymer is selected from the group consisting of 2-vinyl-4,4-dimethyl-1,3-oxazolin-5-one, 2-vinyl-4,4-pentamethylene-1,3-oxazolin-5-one, and 2-vinyl-4,4-dimethyl-1,3-oxazin-6-one.
Claim 6
Dependent Claim
33 words
The pressure-sensitive adhesive tape according to claim 1 wherein said acrylic-functional carboxylic acid monomer component (3) of said interpolymer is selected from the group consisting of acrylic acid, methacrylic acid, and N-acryloylaspartic acid.
Claim 7
Dependent Claim
25 words
The pressure-sensitive adhesive tape according to claim 1 wherein said acrylic-functional carboxylic acid monomer component (3) of said interpolymer is replaced by a precursor thereof.
Claim 8
Dependent Claim
27 words
The pressure-sensitive adhesive tape according to claim 1 wherein said interpolymer component (1) (a) is iso-octyl acrylate, component (2) is 2-vinyl-4,4-diethyl-1,3-oxazolin-5-one, and component (3) is acrylic acid.
Claim 9
Dependent Claim
25 words
The pressure-sensitive adhesive tape according to claim 1 wherein component (1) (a) is iso-octyl acrylate, component (2) is 2-vinyl-4,4-pentamethylene-1,3-oxazolin-5-one, and component (3) is acrylic acid.
Claim 10
Dependent Claim
66 words
The pressure-sensitive adhesive tape according to claim 1 wherein R 3 , R 4 , R 5 , R 6 and R 7 of said alkenyl azlactone monomer component of said interpolymer are substituted by one or more groups selected from alkyl having 1 to 12 carbon atoms, halo, cyano, ether, ester, keto, silyl, and sulfide, the carbon-containing substituent groups having up to 12 carbon atoms.
Claim 11
Dependent Claim
18 words
The pressure sensitive adhesive tape according to claim 1 in which said pressure-sensitive adhesive interpolymer has been cured.
Claim 12
Dependent Claim
324 words
A pressure-sensitive adhesive tape comprising: a. a tape backing, and b. coated on at least one surface thereof a pressure-sensitive adhesive interpolymer which is the reaction product of ethylenically-unsaturated monomers which comprise (1) from about 70 to 90 molar parts of monomers consisting of (a) 75-100 mole percent acrylic acid ester of at least one non-tertiary alkyl alcohol, the molecules of said alcohol containing 1-14 carbon atoms, (b) 15-0 mole percent of at least one monomer selected from the group consisting of vinyl acetate, styrene, vinyl ethers, and alkyl methacrylates, the alkyl group having 1 to 14 carbon atoms, and (c) 10-0 mole percent of at least one monomer selected from the group consisting of acrylamide, methacrylamide, acrylonitrile, methacrylonitrile, and N-vinyl pyrrolidone, and (2) from 25 to 5 molar parts of at least one alkenyl azlactone monomer of the formula I ##STR8## where R 1 is hydrogen or methyl; R 2 is selected from a single bond, --R 3 --, or ##STR9## in which R 3 is a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, and W is --O--, --S--, or --NH--; R 4 and R 7 are independently selected from a single bond, methylene, or substituted methylene having 1 to 12 carbon atoms; R 5 and R 6 are independently substituted or unsubstituted alkyl or cycloalkyl having 1 to 12 carbon atoms, aryl or aralkyl having 6 to 12 carbon atoms, or R 5 and R 6 taken together with the carbon to which they are joined forming a 5- or 6-membered carbocyclic ring, or R 5 and R 6 each may be hydrogen when at least one of R 4 and R 7 is methylene; and (3) from 25 to 5 molar parts of at least one acrylic-functional carboxylic acid monomer selected from acrylic acid, methacrylic acid, itaconic acid, maleic acid, or an N-acryloylamino acid; said interpolymer exhibiting a glass transition temperature (Tg) of less than -15° C.
Claim 13
Dependent Claim
324 words
A pressure-sensitive adhesive tape comprising: a. a tape backing, and b. coated on at least one surface thereof a pressure-sensitive adhesive interpolymer which is the reaction product of ethylenically-unsaturated monomers which comprise (1) from about 70 to 90 molar parts of monomers consisting of (a) 75-100 mole percent acrylic acid ester of at least one non-tertiary alkyl alcohol, the molecules of said alcohol containing 1-14 carbon atoms, (b) 15-0 mole percent of at least one monomer selected from the group consisting of vinyl acetate, styrene, vinyl ethers, and alkyl methacrylates, the alkyl group having 1 to 14 carbon atoms, and (c) 10-0 mole percent of at least one monomer selected from the group consisting of acrylamide, methacrylamide, acrylonitrile, methacrylonitrile, and N-vinyl pyrrolidone, and (2) from 25 to 5 molar parts of at least one alkenyl azlactone monomer of the formula I ##STR8## where R 1 is hydrogen or methyl; R 2 is selected from a single bond, --R 3 --, or ##STR9## in which R 3 is a substituted or unsubstituted alkylene group having 1 to 12 carbon atoms, and W is --O--, --S--, or --NH--; R 4 and R 7 are independently selected from a single bond, methylene, or substituted methylene having 1 to 12 carbon atoms; R 5 and R 6 are independently substituted or unsubstituted alkyl or cycloalkyl having 1 to 12 carbon atoms, aryl or aralkyl having 6 to 12 carbon atoms, or R 5 and R 6 taken together with the carbon to which they are joined forming a 5- or 6-membered carbocyclic ring, or R 5 and R 6 each may be hydrogen when at least one of R 4 and R 7 is methylene; and (3) from 25 to 5 molar parts of at least one acrylic-functional carboxylic acid monomer selected from acrylic acid, methacrylic acid, itaconic acid, maleic acid, or an N-acryloylamino acid; said interpolymer exhibiting a glass transition temperature (Tg) of less than -15° C.
Claim 14
Dependent Claim
15 words
The pressure-sensitive adhesive tape according to claim 11 in which component b has been cured.
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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) | 1989-10-27 | 1990-04-28 | 1990-10-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-10-27 | 1994-04-28 | 1994-10-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-10-27 | 1998-04-28 | 1998-10-28 | $7700.00 | Window Closed / Lapsed |