US5883208A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Initiator system and adhesive composition made therewith
Assignee: 3M Co
•
Filing: 1996-11-08
•
Granted: 1999-03-16
•
Expires: 2016-11-08
Abstract
Abstract Systems for initiating the polymerization of acrylic monomers comprising (1) organoborane amine complexes and (2) decomplexers comprising at least one anhydride group. Adhesive compositions prepared from the initiator systems advantageously exhibit low levels of mobile constituents, excellent solvent resistance, and good adhesion to low energy surfaces.
Inventors
- 👤 E. John Deviny
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 16:40
CPC Classifications
C; C09; C09J; C09J4/00; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/12; C08F4/00; C08F4/42; C08F4/44; C08F4/52; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/3154; Y10T428/31544; Y10T428/31855; Y10T428/31909; Y10T428/31928
Claims Analysis
Total Claims: 49
Claim 1
Independent Claim
35 words
An initiator system capable of initiating the polymerization of acrylic monomers comprising (1) an organoborane amine complex and (2) a decomplexer comprising at least one anhydride group and at least one free radically polymerizable group.
Claim 2
Dependent Claim
35 words
An initiator system capable of initiating the polymerization of acrylic monomers comprising (1) an organoborane amine complex and (2) a decomplexer comprising at least one anhydride group and at least one free radically polymerizable group.
Claim 3
Dependent Claim
32 words
An initiator system capable of initiating the polymerization of acrylic monomers comprising (1) an organoborane amine complex and (2) a decomplexer having a cyclic structure and comprising at least one anhydride group.
Claim 4
Dependent Claim
32 words
An initiator system capable of initiating the polymerization of acrylic monomers comprising (1) an organoborane amine complex and (2) a decomplexer having a cyclic structure and comprising at least one anhydride group.
Claim 5
Dependent Claim
59 words
A polymerizable acrylic composition comprising: a) at least one acrylic monomer; b) an effective amount of an organoborane amine complex; and c) an effective amount of a decomplexer having a cyclic structure and comprising at least one anhydride group, said decomplexer being reactive with said amine to liberate the organoborane to initiate polymerization of at least one acrylic monomer.
Claim 6
Dependent Claim
59 words
A polymerizable acrylic composition comprising: a) at least one acrylic monomer; b) an effective amount of an organoborane amine complex; and c) an effective amount of a decomplexer having a cyclic structure and comprising at least one anhydride group, said decomplexer being reactive with said amine to liberate the organoborane to initiate polymerization of at least one acrylic monomer.
Claim 7
Dependent Claim
18 words
An initiator system according to claim 1 wherein said organoborane amine complex comprises at least two amine groups.
Claim 8
Dependent Claim
34 words
An initiator system according to claim 1 wherein said decomplexer has the structure: ##STR10## wherein each R 1 and R 2 are independently selected from the group consisting of aliphatic, cycloaliphatic and aromatic groups.
Claim 9
Dependent Claim
46 words
An initiator system according to claim 5 wherein at least one of the R 1 and R 2 groups comprises a group selected from the group consisting of monosubstituted alkene groups, 1,1-disubstituted alkene groups, and 1,2-disubstituted alkene groups which are part of an α,β-unsaturated carbonyl structure.
Claim 10
Dependent Claim
23 words
An initiator system according to claim 2 wherein said decomplexer has the following structure: ##STR11## wherein R 3 is a divalent organic radical.
Claim 11
Dependent Claim
37 words
An initiator system according to claim 7 wherein R 3 comprises a group selected from the group consisting of monosubstituted alkene groups, 1,1-disubstituted alkene groups, and 1,2-disubstituted alkene groups which are part of an α,β-unsaturated carbonyl structure.
Claim 12
Dependent Claim
24 words
An initiator system according to claim 7 wherein said cyclic structure comprises the reaction product of an active hydrogen containing compound and a polyanhydride.
Claim 13
Dependent Claim
71 words
An initiator system according to claim 9 wherein said active hydrogen containing compound has the following structure: ##STR12## wherein R 4 is selected from the group consisting of hydrogen, methyl, ethyl and chlorine; R 5 is selected from the group consisting of alkyl groups; and X is selected from the group consisting of oxygen and NR 6 wherein R 6 is selected from the group consisting of hydrogen and alkyl groups.
Claim 14
Dependent Claim
41 words
An initiator system according to claim 10 wherein R 4 is selected from the group consisting of hydrogen and methyl; R 5 is selected from the group consisting of alkyl groups having 2 to 4 carbon atoms; and X is oxygen.
Claim 15
Dependent Claim
85 words
An initiator system according to claim 9 wherein said active hydrogen containing compound-has the following structure: ##STR13## wherein R 1 is selected from the group consisting of hydrogen, methyl, ethyl and chlorine; each R 2 and R 4 are independently selected from the group consisting of alkyl groups; X is selected from the group consisting of oxygen and NR 6 wherein R 6 is selected from the group consisting of hydrogen and alkyl groups; and m is an integer greater than or equal to 1.
Claim 16
Dependent Claim
67 words
An initiator system according to claim 12 wherein R 4 is selected from the group consisting of hydrogen and methyl; R 5 is selected from the group consisting of alkyl groups having 2 to 4 carbon atoms; X is oxygen; R 7 is selected from the group consisting of alkyl groups having 3 to 5 carbon atoms; and m is an integer greater from 1 to 4.
Claim 17
Dependent Claim
27 words
An initiator system according to claim 1 wherein said decomplexer is selected from the group consisting of methacrylic anhydride, itaconic anhydride, maleic anhydride and isobutenyl succinic anhydride.
Claim 18
Dependent Claim
18 words
An initiator system according to claim 1 wherein said organoborane amine complex comprises at least two amine groups.
Claim 19
Dependent Claim
89 words
An initiator system according to claim 1 wherein said complex has the structure: ##STR14## wherein R 8 is selected from the group consisting of alkyl groups having 1 to 10 carbon atoms; R 9 and R 10 are independently selected from the group consisting of alkyl groups having 1 to 10 carbon atoms and phenyl-containing groups; the value of v is selected so as to provide a 0.5:1 to 4:1 ratio of primary or secondary amine nitrogen atoms to boron atoms in the complex; and Am is an amine.
Claim 20
Dependent Claim
80 words
An initiator system according to claim 16 wherein Am has the structure: ##STR15## where R 11 and R 12 are independently selected from the group consisting of hydrogen, alkyl groups having 1 to 10 carbon atoms, hydroxyethyl and ##STR16## wherein R 13 and R 14 are independently selected from the group consisting of hydrogen and alkyl groups having 1 to 10 carbon atoms; m is an integer from 2 to 10; and n is an integer from 1 to 6.
Claim 21
Dependent Claim
91 words
An initiator system according to claim 16 wherein Am is a polyoxyalkylenepolyamine having a structure selected from the group consisting of: H.sub.2 NR.sub.15 O--(R.sub.16 O).sub.w --(R.sub.17 O).sub.x --(R.sub.16 O).sub.y --R.sub.15 NH.sub.2 or H.sub.2 NR.sub.15 O--(R.sub.16 O).sub.w !.sub.z --R.sub.18 wherein R 15 , R 16 and R 17 are independently selected from the group consisting of alkylene and alkyl groups; R 18 is selected from the group consisting of polyol residues; the value of w is ≧1; the value of x and y are ≧0; and the value of z is >2.
Claim 22
Dependent Claim
60 words
An initiator system according to claim 16 wherein Am has the structure E--(L--E) q --L--E wherein each E group is independently selected from the group consisting of the residues of diprimary amine-terminated materials; each L is independently selected from the group consisting of the residues of materials having at least two groups reactive with primary amines; and q is ≧0.
Claim 23
Dependent Claim
62 words
A polymerizable acrylic composition comprising: a) at least one acrylic monomer; b) an effective amount of an organoborane amine complex; and c) an effective amount of a decomplexer comprising at least one anhydride group and at least one free radically polymerizable group, said decomplexer being reactive with said amine to liberate the organoborane to initiate polymerization of at least one acrylic monomer.
Claim 24
Dependent Claim
62 words
A polymerizable acrylic composition comprising: a) at least one acrylic monomer; b) an effective amount of an organoborane amine complex; and c) an effective amount of a decomplexer comprising at least one anhydride group and at least one free radically polymerizable group, said decomplexer being reactive with said amine to liberate the organoborane to initiate polymerization of at least one acrylic monomer.
Claim 25
Dependent Claim
38 words
A polymerizable acrylic composition according to claim 20 wherein the at least one acrylic monomer is selected from the group consisting of monofunctional acrylate ester, monofunctional methacrylate ester, substituted derivatives of the foregoing, and blends of the foregoing.
Claim 26
Dependent Claim
19 words
A polymerizable acrylic composition according to claim 20, wherein said organoborane amine complex comprises at least two amine groups.
Claim 27
Dependent Claim
35 words
A polymerizable acrylic composition according to claim 20 wherein said decomplexer has the structure: ##STR17## wherein each R 1 and R 2 are independently selected from the group consisting of aliphatic, cycloaliphatic and aromatic groups.
Claim 28
Dependent Claim
46 words
A polymerizable acrylic composition according to claim 23 wherein at least one of the R 1 and R 2 comprises a group selected from the group consisting of monosubstituted alkene groups, 1,1-disubstituted alkene groups, and 1,2-disubstituted alkene groups which are part of an α,β-unsaturated carbonyl structure.
Claim 29
Dependent Claim
24 words
A polymerizable acrylic composition according to claim 3 wherein said decomplexer has the following structure: ##STR18## wherein R 3 is a divalent organic radical.
Claim 30
Dependent Claim
40 words
A polymerizable acrylic composition according to claim 25 wherein R 3 comprises at least one group selected from the group consisting of monosubstituted alkene groups, 1,1-disubstituted alkene groups, and 1,2-disubstituted alkene groups which are part of an α,β-unsaturated carbonyl structure.
Claim 31
Dependent Claim
24 words
A polymerizable acrylic composition according to claim 25 wherein said decomplexer comprises the reaction product of an active hydrogen containing compound and a polyanhydride.
Claim 32
Dependent Claim
72 words
A polymerizable acrylic composition according to claim 27 wherein said active hydrogen containing compound has the following structure: ##STR19## wherein R 4 is selected from the group consisting of hydrogen, methyl, ethyl and chlorine; R 2 is selected from the group consisting of alkyl groups; and X is selected from the group consisting of oxygen and NR 6 wherein R 6 is selected from the group consisting of hydrogen and alkyl groups.
Claim 33
Dependent Claim
87 words
A polymerizable acrylic composition according to claim 27 wherein said active hydrogen containing compound has the following structure: ##STR20## wherein R 1 is selected from the group consisting of hydrogen, methyl, ethyl and chlorine; each R 2 and R 4 are independently selected from the group consisting of alkyl groups; X is selected from the group consisting of oxygen and NR 6 wherein R 6 is selected from the group consisting of hydrogen and alkyl groups; and m is an integer greater than or equal to 1.
Claim 34
Dependent Claim
28 words
A polymerizable acrylic composition according to claim 20 wherein said decomplexer is selected from the group consisting of methacrylic anhydride, itaconic anhydride, maleic anhydride and isobutenyl succinic anhydride.
Claim 35
Dependent Claim
9 words
A polymerized acrylic adhesive composition according to claim 20.
Claim 36
Independent Claim
102 words
A method of initiating a polymerization of at least one acrylic monomer, the method comprising the steps of: a) providing at least one acrylic monomer; b) blending the at least one acrylic monomer with the components of a polymerization initiator system, said system comprising; i) an organoborane amine complex, ii) an effective amount of a decomplexer comprising at least one anhydride group and at least one free radically polymerizable group, said decomplexer being reactive with amine for liberating the organoborane to initiate the polymerization of the at least one acrylic monomer; and c) initiating polymerization of the at least one acrylic monomer.
Claim 37
Independent Claim
102 words
A method of initiating a polymerization of at least one acrylic monomer, the method comprising the steps of: a) providing at least one acrylic monomer; b) blending the at least one acrylic monomer with the components of a polymerization initiator system, said system comprising; i) an organoborane amine complex, ii) an effective amount of a decomplexer comprising at least one anhydride group and at least one free radically polymerizable group, said decomplexer being reactive with amine for liberating the organoborane to initiate the polymerization of the at least one acrylic monomer; and c) initiating polymerization of the at least one acrylic monomer.
Claim 38
Independent Claim
93 words
A method of increasing the solvent resistance of a polymerized acrylic adhesive composition obtained by organoborane-initiated polymerization of acrylic monomer, said method comprising the steps of a) providing at least one acrylic monomer; b) providing an organoborane amine complex comprising at least two amine groups; c) providing a decomplexer comprising at least one anhydride group and at least one free radically polymerizable group; d) blending components a), b) and c), and; e) initiating polymerization of the at least one acrylic monomer and continuing polymerization until a solvent resistant acrylic adhesive composition is obtained.
Claim 39
Independent Claim
93 words
A method of increasing the solvent resistance of a polymerized acrylic adhesive composition obtained by organoborane-initiated polymerization of acrylic monomer, said method comprising the steps of a) providing at least one acrylic monomer; b) providing an organoborane amine complex comprising at least two amine groups; c) providing a decomplexer comprising at least one anhydride group and at least one free radically polymerizable group; d) blending components a), b) and c), and; e) initiating polymerization of the at least one acrylic monomer and continuing polymerization until a solvent resistant acrylic adhesive composition is obtained.
Claim 40
Dependent Claim
52 words
An initiator system capable of initiating the polymerization of acrylic monomers comprising (1) an organoborane amine complex, and (2) a decomplexer comprising at least one hydride group selected from the group consisting of aliphatic anhydrides having an aliphatic group comprising at least 2 carbon atoms cycloaliphatic anhydrides, cyclic anhydrides, and aromatic anhydrides.
Claim 41
Dependent Claim
52 words
An initiator system capable of initiating the polymerization of acrylic monomers comprising (1) an organoborane amine complex, and (2) a decomplexer comprising at least one hydride group selected from the group consisting of aliphatic anhydrides having an aliphatic group comprising at least 2 carbon atoms cycloaliphatic anhydrides, cyclic anhydrides, and aromatic anhydrides.
Claim 42
Dependent Claim
51 words
An initiator system capable of initiating the polymerization of acrylic monomers comprising (1) an organoborane amine complex and (2) a decomplexer comprising at least one anhydride group capable of reacting with the amine portion of the organoborane amine complex to form a decomplexer-amine reaction product comprising a free radically polymerizable group.
Claim 43
Dependent Claim
51 words
An initiator system capable of initiating the polymerization of acrylic monomers comprising (1) an organoborane amine complex and (2) a decomplexer comprising at least one anhydride group capable of reacting with the amine portion of the organoborane amine complex to form a decomplexer-amine reaction product comprising a free radically polymerizable group.
Claim 44
Dependent Claim
20 words
An initiator system according to claim 35, wherein said decomplexer-amine reaction product comprises more than one free radically polymerizable group.
Claim 45
Dependent Claim
81 words
A polymerizable acrylic composition comprising: a) at least one acrylic monomer; b) an effective amount of an organoborane amine complex; and c) an effective amount of a decomplexer comprising at least one anhydride group, said decomplexer being reactive with said amine to liberate the organoborane to initiate polymerization of at least one acrylic monomer, said anhydride group capable of reacting with the amine portion of the organoborane amine complex to form a decomplexer-amine reaction product comprising a free radically polymerizable group.
Claim 46
Dependent Claim
81 words
A polymerizable acrylic composition comprising: a) at least one acrylic monomer; b) an effective amount of an organoborane amine complex; and c) an effective amount of a decomplexer comprising at least one anhydride group, said decomplexer being reactive with said amine to liberate the organoborane to initiate polymerization of at least one acrylic monomer, said anhydride group capable of reacting with the amine portion of the organoborane amine complex to form a decomplexer-amine reaction product comprising a free radically polymerizable group.
Claim 47
Dependent Claim
20 words
A polymerizable acrylic composition of claim 37, wherein said decomplexer-amine reaction product comprises more than one free radically polymerizable group.
Claim 48
Dependent Claim
75 words
A polymerizable acrylic composition comprising: a) at least one acrylic monomer; b) an effective amount of an organoborane amine complex; and c) an effective amount of a decomplexer comprising at least one anhydride group selected from the group consisting of aliphatic anhydrides having a C 2 or greater alkyl group, cycloaliphatic anhydrides, and aromatic anhydrides, said decomplexer being reactive with said amine to liberate the organoborane to initiate polymerization of at least one acrylic monomer.
Claim 49
Dependent Claim
75 words
A polymerizable acrylic composition comprising: a) at least one acrylic monomer; b) an effective amount of an organoborane amine complex; and c) an effective amount of a decomplexer comprising at least one anhydride group selected from the group consisting of aliphatic anhydrides having a C 2 or greater alkyl group, cycloaliphatic anhydrides, and aromatic anhydrides, said decomplexer being reactive with said amine to liberate the organoborane to initiate polymerization of at least one acrylic monomer.
References Cited (Backward Citations)
CA664459A
Cited
US2985633A
Cited
US3275611A
Cited
US3340193A
Cited
US3141862A
Cited
GB904403A
Cited
US3451952A
Cited
GB988632A
Cited
GB1113722A
Cited
GB1132261A
Cited
US3425988A
Cited
JPS4214318Y1
Cited
US3476727A
Cited
US3418260A
Cited
JPS4529195Y1
Cited
US3527737A
Cited
JPS4818928B1
Cited
US3829973A
Cited
JPS53102394A
Cited
US4167616A
Cited
EP0051796A1
Cited
US4639498A
Cited
US4638092A
Cited
US4379728A
Cited
US4515724A
Cited
US4676858A
Cited
US4524181A
Cited
US4485229A
Cited
US4731416A
Cited
US4921921A
Cited
US4874814A
Cited
US4985516A
Cited
US4656229A
Cited
US4684538A
Cited
US5021507A
Cited
JPS62288675A
Cited
US4904360A
Cited
US4721751A
Cited
US4920188A
Cited
US4775734A
Cited
JPH03177470A
Cited
JPH03264509A
Cited
EP0511464A1
Cited
US5143884A
Cited
CA2061021A1
Cited
US5106928A
Cited
JPH05235089A
Cited
US5286821A
Cited
AU649582B2
Cited
US5376746A
Cited
US5401805A
Cited
US5310835A
Cited
US5539070A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2002-03-15 | 2002-09-14 | 2003-03-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2006-03-15 | 2006-09-14 | 2007-03-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2010-03-15 | 2010-09-14 | 2011-03-16 | $7700.00 | Window Closed / Lapsed |