US4182823A
Expired / Lapsed
US
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Anionic polymerization inhibitor for cyanoacrylate adhesives
Assignee: Ingredion Inc
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Filing: 1978-08-18
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Granted: 1980-01-08
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Expires: 1998-08-18
Abstract
Abstract An adhesive composition based on 2-cyanoacrylate esters contains as an anionic polymerization inhibitor an acid chelate formed of boric acid or a derivative thereof and a selected polyhydroxy compound. The chelate is conveniently formed in situ in the 2-cyanoacrylate ester, but may also be prepared separately and added to the ester directly. An exemplary acid chelate used as stabilizer is prepared from boric acid and pyrogallol. The resulting stabilized adhesive compositions have a rapid cure rate and may be used on a wide variety of substrates.
Inventors
- 👤 Jules E. Schoenberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 19:23
CPC Classifications
C; C08; C08F; C08F22/00; C08F22/30; C08F22/32; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31855
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
114 words
An adhesive composition comprising a mixture of: A. at least 65% by weight of a monomeric ester of 2-cyanoacrylic acid of the general formula: ##STR4## wherein R is an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cyclohexyl group, or a phenyl group; and B. a stabilizing amount of a protonic acid chelate containing a boron atom bonded to at least three oxygen atoms formed from reaction of boric acid, or a compound which forms boric acid or tetravalent monoborate ions in the monomeric ester, with a polyhydroxy compound capable of forming said chelate and containing no reactive groups which can initiate anionic polymerization.
Claim 2
Dependent Claim
114 words
An adhesive composition comprising a mixture of: A. at least 65% by weight of a monomeric ester of 2-cyanoacrylic acid of the general formula: ##STR4## wherein R is an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cyclohexyl group, or a phenyl group; and B. a stabilizing amount of a protonic acid chelate containing a boron atom bonded to at least three oxygen atoms formed from reaction of boric acid, or a compound which forms boric acid or tetravalent monoborate ions in the monomeric ester, with a polyhydroxy compound capable of forming said chelate and containing no reactive groups which can initiate anionic polymerization.
Claim 3
Dependent Claim
28 words
The composition of claim 1 wherein said chelate is present in said 2-cyanoacrylic acid ester in an amount of 10-600 ppm., based on the weight of the ester.
Claim 4
Dependent Claim
23 words
The composition of claim 1 wherein said compound which forms boric acid or tetravalent monoborate ions is an anhydride or a borate ester.
Claim 5
Dependent Claim
15 words
The composition of claim 3 wherein said compound is boric oxide or a trialkyl borate.
Claim 6
Dependent Claim
40 words
The composition of claim 1 wherein said polyhydroxy compound has at least two hydroxyl groups attached to adjacent carbon atoms or to carbon atoms separated by one atom, such that the chelate formed therefrom contains a five- or six-membered ring.
Claim 7
Dependent Claim
33 words
The composition of claim 1 wherein at least one of the hydroxyl groups of said polyhydroxy compound which react to form said chelate is attached to a carbon atom containing a multiple bond.
Claim 8
Dependent Claim
26 words
The composition of claim 1 wherein said polyhydroxy compound is selected from the group consisting of ortho-dihydroxybenzenes, ortho-hydroxybenzoic acids, aliphatic α-hydroxy acids, and aliphatic dicarboxylic acids.
Claim 9
Dependent Claim
25 words
The composition of claim 7 wherein said polyhydroxy compound is selected from the group consisting of pyrogallol, catechol, salicylic acid, tartaric acid, and oxalic acid.
Claim 10
Dependent Claim
15 words
The composition of claim 1 wherein there is additionally present a free radical polymerization inhibitor.
Claim 11
Dependent Claim
15 words
The composition of claim 1 wherein there is additionally present a gaseous anionic polymerization inhibitor.
Claim 12
Dependent Claim
28 words
The composition of claim 1 wherein R of said 2-cyanoacrylic acid ester is a C 1 -C 4 alkyl group or a C 2 -C 4 alkenyl group.
Claim 13
Dependent Claim
75 words
In a process for preparing 2-cyanoacrylate adhesive compositions, the improvement which comprises adding to said composition a stabilizing amount of a protonic acid chelate containing a boron atom bonded to at least three oxygen atoms formed from reaction of boric acid, or a compound which forms boric acid or tetravalent monoborate ions in the monomeric ester, with a polyhydroxy compound capable of forming said chelate and containing no reactive groups which can initiate anionic polymerization.
Claim 14
Dependent Claim
75 words
In a process for preparing 2-cyanoacrylate adhesive compositions, the improvement which comprises adding to said composition a stabilizing amount of a protonic acid chelate containing a boron atom bonded to at least three oxygen atoms formed from reaction of boric acid, or a compound which forms boric acid or tetravalent monoborate ions in the monomeric ester, with a polyhydroxy compound capable of forming said chelate and containing no reactive groups which can initiate anionic polymerization.
Claim 15
Dependent Claim
105 words
In a process for preparing 2-cyanoacrylate adhesive compositions, the improvement which comprises adding to said composition an amount of boric acid, or a compound which forms boric acid or tetravalent monoborate ions in the monomeric ester, and an amount of a polyhydroxy compound capable of forming a protonic acid chelate containing a boron atom bonded to at least three oxygen atoms with said boric acid or boric-acid-forming compound and containing no reactive groups which can initiate anionic polymerization, the amounts of said boric acid, or boric-acid-forming compound, and said polyhydroxy compound being sufficient to provide a stabilizing amount of said chelate in said 2-cyanoacrylate adhesive.
Claim 16
Dependent Claim
105 words
In a process for preparing 2-cyanoacrylate adhesive compositions, the improvement which comprises adding to said composition an amount of boric acid, or a compound which forms boric acid or tetravalent monoborate ions in the monomeric ester, and an amount of a polyhydroxy compound capable of forming a protonic acid chelate containing a boron atom bonded to at least three oxygen atoms with said boric acid or boric-acid-forming compound and containing no reactive groups which can initiate anionic polymerization, the amounts of said boric acid, or boric-acid-forming compound, and said polyhydroxy compound being sufficient to provide a stabilizing amount of said chelate in said 2-cyanoacrylate adhesive.
Claim 17
Dependent Claim
40 words
The process of claim 13 wherein said boric acid or boric-acid-forming compound is added in an amount of 5-1000 ppm. and said polyhydroxy compound is added in an amount of 5-500 ppm., based on the weight of the 2-cyanoacrylate ester.
Claim 18
Dependent Claim
32 words
The composition of claim 1 wherein said chelate contains a group of the formula ##STR5## wherein the carbon atoms are directly bonded to each other or separated by one or more atoms.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-01-07 | 1983-07-09 | 1984-01-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-07 | 1987-07-09 | 1988-01-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-07 | 1991-07-09 | 1992-01-08 | $7700.00 | Window Closed / Lapsed |