US5616796A
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Organoborane polyamine complexes and adhesive composition made therewith
Assignee: 3M Innovative Properties Co
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Filing: 1995-04-14
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Granted: 1997-04-01
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Expires: 2015-04-14
Abstract
Abstract A complex comprises organoborane and polyamine. The polyamine is the reaction product of a diprimary amine-terminated material and a material having at least two groups reactive with primary amine. The complexes are useful in systems for initiating the polymerization of acrylic monomer, which systems further include a material reactive with amine. Polymerizable acrylic monomer compositions useful as adhesives can be prepared.
Inventors
- 👤 Alphonsus V. Pocius
- 👤 Tadesse G. Nigatu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 21:10
CPC Classifications
C; C09; C09J; C09J4/00; B; B32; B32B; B32B27/00; B32B27/30; B32B7/00; B32B7/04; B32B7/12; C07; C07F; C07F5/00; C07F5/02; C07F5/027; C08; C08F; C08F4/00; C08F4/42; C08F4/44; C08F4/52; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31855; Y10T428/31909; Y10T428/31913; Y10T428/31928
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
43 words
A complex comprising organoborane and polyamine, wherein the polyamine comprises the reaction product of a diprimary amine-terminated material and a material having at least two groups reactive with primary amine, wherein a majority of the terminal groups in the polyamine are primary amine.
Claim 2
Dependent Claim
43 words
A complex comprising organoborane and polyamine, wherein the polyamine comprises the reaction product of a diprimary amine-terminated material and a material having at least two groups reactive with primary amine, wherein a majority of the terminal groups in the polyamine are primary amine.
Claim 3
Dependent Claim
46 words
A complex according to claim 1 wherein the organoborane has structure ##STR23## wherein: R 1 is an alkyl group having 1 to 10 carbon atoms; and R 2 and R 3 are independently selected from alkyl groups having 1 to 10 carbon atoms and phenyl-containing groups.
Claim 4
Dependent Claim
28 words
A complex according to claim 1 wherein the diprimary amine-terminated material is selected from the group consisting of polyoxyalkylenediamine, alkyl diamine, aryl diamine, alkaryl diamine, and blends thereof.
Claim 5
Dependent Claim
60 words
A complex according to claim 1 wherein the material having at least two groups reactive with primary amine has the structure Y--R--Z, wherein Y and Z are moieties reactive with primary amine and are independently selected from the group consisting of carboxylic acid, carboxylic acid halide, ester, aldehyde, epoxide, amino alcohol, and acrylic, and R is a divalent organic radical.
Claim 6
Dependent Claim
13 words
A complex according to claim 1 that is not pyrophoric under ambient conditions.
Claim 7
Dependent Claim
105 words
An organoborane polyamine complex having the structure ##STR24## wherein: R 1 is an alkyl group having 1 to 10 carbon atoms; R 2 and R 3 are independently selected from alkyl groups having 1 to 10 carbon atoms and phenyl-containing groups; Am is a polyamine that comprises the reaction product of a diprimary amine-terminated material and a material having at least two groups reactive with primary amine, wherein a majority of the terminal groups in the polyamine are primary amine; and the value of v is selected so as to provide an effective ratio of primary amine nitrogen atoms to boron atoms in the complex.
Claim 8
Dependent Claim
105 words
An organoborane polyamine complex having the structure ##STR24## wherein: R 1 is an alkyl group having 1 to 10 carbon atoms; R 2 and R 3 are independently selected from alkyl groups having 1 to 10 carbon atoms and phenyl-containing groups; Am is a polyamine that comprises the reaction product of a diprimary amine-terminated material and a material having at least two groups reactive with primary amine, wherein a majority of the terminal groups in the polyamine are primary amine; and the value of v is selected so as to provide an effective ratio of primary amine nitrogen atoms to boron atoms in the complex.
Claim 9
Dependent Claim
29 words
An organoborane polyamine complex according to claim 6 wherein R 1 , R 2 and R 3 are independently selected from alkyl groups having 1 to 5 carbon atoms.
Claim 10
Dependent Claim
20 words
An organoborane polyamine complex according to claim 7 wherein R 1 , R 2 and R 3 are the same.
Claim 11
Dependent Claim
15 words
An organoborane polyamine complex according to claim 6 wherein the diprimary amine-terminated material is polyoxyalkylenediamine.
Claim 12
Dependent Claim
74 words
An organoborane polyamine complex according to claim 9 wherein the polyoxyalkylenediamine has the structure H 2 NR 4 O--(R 5 O) w --(R 6 O) x --(R 5 O) y --R 4 NH 2 wherein R 4 , R 5 , and R 6 are alkylene groups having 1 to 10 carbon atoms and which may be the same or which may be different; w is ≧1; x is ≧0; and y is ≧0.
Claim 13
Dependent Claim
46 words
An organoborane polyamine complex according to claim 10 wherein R 4 is an alkyl group having 2 to 4 carbon atoms, R 5 is an alkyl group having 2 or 3 carbon atoms, and R 6 is an alkyl group having 2 or 3 carbon atoms.
Claim 14
Dependent Claim
29 words
An organoborane polyamine complex according to claim 6 wherein the diprimary amine-terminated material is a linear alkyldiamine in which the alkyl group has from 1 to 12 carbon atoms.
Claim 15
Dependent Claim
56 words
An organoborane polyamine complex according to claim 6 wherein the material having at least two groups reactive with primary amine has the structure Y--R--Z wherein Y and Z are moieties independently selected from the group consisting of carboxylic acid, carboxylic acid halide, ester, aldehyde, epoxide, amino alcohol, and acrylic, and R is a divalent organic radical.
Claim 16
Dependent Claim
21 words
An organoborane polyamine complex according to claim 13 wherein Y and Z are the same and the polyamine is substantially linear.
Claim 17
Dependent Claim
27 words
An organoborane polyamine complex according to claim 6 wherein the ratio of primary amine nitrogen atoms to boron atoms in the complex is about 0.5:1 to 4.1.
Claim 18
Dependent Claim
25 words
An organoborane polyamine complex according to claim 15 wherein the ratio of primary amine nitrogen atoms to boron atoms in the complex is about 1:1.
Claim 19
Independent Claim
74 words
A system capable of initiating the polymerization of an acrylic monomer, the system comprising: a) a complex comprising organoborane and polyamine, the polyamine comprising the reaction product of a diprimary amine-terminated material and a material having at least two groups reactive with primary amine, wherein a majority of the terminal groups in the polyamine are primary amine; and b) an effective amount of a compound that is reactive with amine for liberating the organoborane.
Claim 20
Independent Claim
74 words
A system capable of initiating the polymerization of an acrylic monomer, the system comprising: a) a complex comprising organoborane and polyamine, the polyamine comprising the reaction product of a diprimary amine-terminated material and a material having at least two groups reactive with primary amine, wherein a majority of the terminal groups in the polyamine are primary amine; and b) an effective amount of a compound that is reactive with amine for liberating the organoborane.
Claim 21
Dependent Claim
228 words
A system according to claim 16 wherein the complex has the structure ##STR25## wherein: R 1 is an alkyl group having 1 to 10 carbon atoms; R 2 and R 3 are independently selected from alkyl groups having 1 to 10 carbon atoms and phenyl-containing groups; E--(L--E) z --L--E is a polyamine wherein: each E is the residue of a material that is selected from the group consisting of: (a) polyoxyalkylenediamine having the structure H 2 NR 4 O--(R 5 O) w --(R 6 O) x --(R 5 O) y --R 4 NH 2 wherein R 4 , and R 6 , and R 6 are alkylene groups having 1 to 10 carbon atoms and which may be the same or which may be different; w is ≧1; x is ≧0; y is ≧0; and (b) linear alkyldiamine in which the alkyl group has from 1 to 12 carbon atoms; and each L is a linking group that is the residue of a material having the structure Y--R 7 --X, wherein Y and X are independently selected from the group consisting of carboxylic acid, carboxylic acid halide, ester, aldehyde, epoxide, amino alcohol, and acrylic and R 7 is a divalent organic radical z≧0; and the value of v is selected so as to provide an effective ratio of primary amine nitrogen atoms to boron atoms in the complex.
Claim 22
Dependent Claim
123 words
A system according to claim 18 wherein: R 1 , R 2 and R 3 are alkyl groups having 1 to 5 carbon atoms and are the same; R 4 is an alkyl group having 2 to 4 carbon atoms; R 5 is an alkyl group having 2 or 3 carbon atoms; R 6 is an alkyl group having 2 or 3 carbon atoms; Y and X are the same and are selected from the group consisting of epoxide, acrylic and carboxylic acid; the value of v is selected such that the ratio of to primary amine nitrogen atoms to boron atoms in the complex is about 1:1 to 2:1; and the complex is a liquid at room temperature and is substantially linear.
Claim 23
Dependent Claim
32 words
A system according to claim 18 wherein the compound that is reactive with amine for liberating organoborane is selected from the group consisting of isocyanate, acid, acid chloride, sulfonyl chloride, and aldehyde.
Claim 24
Dependent Claim
23 words
A system according to claim 20 wherein the compound that is reactive with amine for liberating organoborane is acrylic acid or methacrylic acid.
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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) | 2000-03-31 | 2000-09-30 | 2001-04-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-03-31 | 2004-09-30 | 2005-04-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-03-31 | 2008-09-30 | 2009-04-01 | $7700.00 | Window Closed / Lapsed |