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Azlactone-containing pressure-sensitive adhesives

Assignee: 3M Co
•
Filing: 1986-06-24
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Granted: 1987-10-13
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Expires: 2006-06-24
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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 2026-11-06 15:54
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 366 words
A composite structure comprising: (a) two substrates, and (b) coated between said substrates 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## wherein 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., with the proviso that said substituting groups are unreactive with said azlactone ring and said monomers having been polymerized in a medium free of alcohol and other crosslinking agents capable of reacting with the azlactone ring.
Claim 2
Dependent Claim 366 words
A composite structure comprising: (a) two substrates, and (b) coated between said substrates 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## wherein 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., with the proviso that said substituting groups are unreactive with said azlactone ring and said monomers having been polymerized in a medium free of alcohol and other crosslinking agents capable of reacting with the azlactone ring.
Claim 3
Dependent Claim 365 words
A composite structure comprising: (a) two substrates, and (b) coated between said substrates 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) 75-100 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) 15-0 mole percent of at least one monomer selected from the group consisting of vinyl acetate, styrene, vinyl ethers, and alkyl methacrylate, 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 least one alkenyl azlactone monomer having 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., with the proviso that said substituting groups are unreactive with said azlactone ring and said monomers having been polymerized in a medium free of alcohol and other crosslinking agents capable of reacting with the azlactone ring.
Claim 4
Dependent Claim 365 words
A composite structure comprising: (a) two substrates, and (b) coated between said substrates 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) 75-100 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) 15-0 mole percent of at least one monomer selected from the group consisting of vinyl acetate, styrene, vinyl ethers, and alkyl methacrylate, 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 least one alkenyl azlactone monomer having 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., with the proviso that said substituting groups are unreactive with said azlactone ring and said monomers having been polymerized in a medium free of alcohol and other crosslinking agents capable of reacting with the azlactone ring.
Claim 5
Dependent Claim 27 words
The composite structure 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 6
Dependent Claim 35 words
The composite structure 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 7
Dependent Claim 27 words
The composite structure 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 8
Dependent Claim 32 words
The composite structure 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 9
Dependent Claim 24 words
The composite structure according to claim 1 wherein said acrylic-functional carboxylic acid monomer component (3) of said interpolymer is replaced by a precursor thereof.
Claim 10
Dependent Claim 26 words
The composite structure according to claim 1 wherein component (1)(a) of said interpolymer is iso-octyl acrylate, component (2) is 2-vinyl-4,4-dimethyl-1,3-oxazolin-5-one, and component (3) is acrylic acid.
Claim 11
Dependent Claim 27 words
The composite structure according to claim 1 wherein component (1)(a) of said interpolymer is iso-octyl acrylate, component (2) is 2-vinyl-4,4-pentamethylene-1,3-oxazolin-5-one monomer, and component (3) is acrylic acid.
Claim 12
Dependent Claim 11 words
The composite structure of claim 1 wherein the interpolymer is cured.
Claim 13
Dependent Claim 61 words
The composite structure according to claim 1 wherein R 3 , R 4 , R 5 , R 6 and R 7 of said alkenyl azlactone monomer 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 14
Dependent Claim 11 words
The composite structure of claim 2 wherein the interpolymer is cured.

References Cited (Backward Citations)

US24906A Cited
CA627947A Cited
USRE24906E Cited
US3061567A Cited
GB1121418A Cited
US3598790A Cited
US3583950A Cited
US4181752A Cited
US4216252A Cited
US4157418A Cited
US4304705A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-10-12 1991-04-13 1991-10-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-10-12 1995-04-13 1995-10-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-10-12 1999-04-13 1999-10-13 $7700.00 Window Closed / Lapsed

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