US5386047A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Di-α-cyanopentadienoate disiloxane compounds for use in adhesives
Assignee: Henkel Loctite Corp
•
Filing: 1994-03-11
•
Granted: 1995-01-31
•
Expires: 2014-03-11
Abstract
Abstract Anionically polymerizable di-α-cyanopentadienoate disiloxane compounds of the formula: [CH.sub.2 ═CH--CH═C(CN)--C(═O)--O--CH.sub.2 --R--Si(R").sub.2 ] 2 --O where R is --CH═CH-- or --C(═CH 2 )-- and the R" groups are the same or different hydrocarbon or halo substituted hydrocarbon groups are prepared by hydrolysis of a cyanoacetoxypropenylsilane having a hydrolyzable group attached to the silicon atom and then condensing the resulting disiloxane compound with acrolein. The di-α-cyanopentadienoate disiloxane compounds are useful as instant adhesives and as co-monomers in cyanoacrylate or cyanopentadienoate instant adhesives, providing the adhesive polymers or copolymers with improved thermal resistance.
Inventors
- 👤 Steven T. Nakos
- 👤 John G. Woods
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 22:26
CPC Classifications
C; C08; C08F; C08F136/00; C08F136/02; C08F136/20; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0834; C07F7/0838; C09; C09J; C09J4/00
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
37 words
A silicon containing di-α-cyanopentadienoate disiloxane compound of the formula: [CH.sub.2 ═CH--CH═C(CN)--C(═O)--O--CH.sub.2 --R--Si(R").sub.2 ].sub.2 --O where R is --CH═CH-- or --C(═CH 2 )-- and the R" groups are the same or different hydrocarbon or halo substituted hydrocarbon groups.
Claim 2
Dependent Claim
37 words
A silicon containing di-α-cyanopentadienoate disiloxane compound of the formula: [CH.sub.2 ═CH--CH═C(CN)--C(═O)--O--CH.sub.2 --R--Si(R").sub.2 ].sub.2 --O where R is --CH═CH-- or --C(═CH 2 )-- and the R" groups are the same or different hydrocarbon or halo substituted hydrocarbon groups.
Claim 3
Dependent Claim
18 words
The compound according to claim 1 in which the R" groups are independently alkyl, aromatic or haloalkyl groups.
Claim 4
Dependent Claim
9 words
The compound according to claim 1 which is 1,3-bis(2-cyano-2,4-pentadienoylpropenyl)-1,1,3,3-tetramethyldisiloxane.
Claim 5
Dependent Claim
19 words
The compound according to claim 1 in which the R" groups are a mixture of methyl and phenyl groups.
Claim 6
Dependent Claim
60 words
A method of forming a compound as in claim 1 comprising: hydrolyzing a compound of the formula: A--Si(R").sub.2 --X where A is a cyanoacetoxypropenyl group, R" is as defined in claim 1 and X is a hydrolyzable group, to produce a compound of the formula: A--Si(R".sub.2 --O--Si(R").sub.2 --A and then, condensing the compound A--Si(R") 2 --O--Si(R") 2 --A with acrolein.
Claim 7
Dependent Claim
21 words
A method as in claim 5 wherein the hydrolysis step is carried out in the presence of an alkali bicarbonate catalyst.
Claim 8
Dependent Claim
13 words
A method as in claim 6 wherein the alkali bicarbonate is sodium bicarbonate.
Claim 9
Dependent Claim
18 words
A method as in claim 6 wherein said hydrolyzable group is selected from chloro, alkoxy, acetoxy and ketoximo.
Claim 10
Dependent Claim
15 words
A method as in claim 6 wherein the compound A--Si(R") 2 --X is a cyanoacetoxypropenylchlorodialkylsilane.
Claim 11
Dependent Claim
16 words
A method as in claim 5 wherein the compound A--Si(R") 2 --O--Si(R") 2 --A is 1,3-bis(cyanoacetoxypropenyl)tetramethyldisiloxane.
Claim 12
Dependent Claim
24 words
A polymerizable composition comprising a monomer component which includes a silicon containing di-α-cyanopentadienoate disiloxane compound as in claim 1 and an anionic polymerization inhibitor.
Claim 13
Dependent Claim
24 words
A composition as in claim 11 wherein the di-α-cyanopentadienoate disiloxane compound comprises at least 5% by weight of the monomer component of the composition.
Claim 14
Dependent Claim
13 words
A composition as in claim 11 wherein the di-α-cyanopentadienoate disiloxane compound is 1,3-bis(2-cyano-2,4-pentadienoylpropenyl)-1,1,3,3-tetramethyldisiloxane.
Claim 15
Dependent Claim
17 words
A composition as in claim 11 wherein the monomer component further comprises a non-silicon containing α-cyanopentadienoate compound.
Claim 16
Dependent Claim
15 words
A composition as in claim 11 wherein the monomer component further comprises an α-cyanoacrylate compound.
References Cited (Backward Citations)
US3142698A
Cited
US3316227A
Cited
US3554990A
Cited
SU405873A1
Cited
GB1374464A
Cited
JPS492009A
Cited
SU438260A1
Cited
SU446198A1
Cited
GB1415102A
Cited
US4012402A
Cited
US4153641A
Cited
SU744018A1
Cited
US4276402A
Cited
US4313865A
Cited
JPS56135570A
Cited
JPS56135571A
Cited
JPS57147565A
Cited
JPS57151610A
Cited
JPS57164176A
Cited
JPS57164172A
Cited
JPS57164173A
Cited
JPS57164175A
Cited
JPS57164174A
Cited
US4425471A
Cited
JPS5936652A
Cited
JPS5936177A
Cited
JPS5947272A
Cited
JPS5949099A
Cited
JPS5964681A
Cited
JPS60115676A
Cited
JPS60133082A
Cited
JPS61145267A
Cited
JPS61168607A
Cited
JPS6277393A
Cited
JPS62215595A
Cited
JPS6312677A
Cited
JPS6366276A
Cited
US4793886A
Cited
US4810766A
Cited
JPS63118387A
Cited
JPS6456687A
Cited
US4965387A
Cited
US5187048A
Cited
JPH03167279A
Cited
US5140084A
Cited
US5200238A
Cited
JPH04154880A
Cited
JPH04202195A
Cited
US5136065A
Cited
US5194460A
Cited
JPH05241213A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1998-01-30 | 1998-08-01 | 1999-01-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-01-30 | 2002-08-01 | 2003-01-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-01-30 | 2006-08-01 | 2007-01-31 | $7700.00 | Window Closed / Lapsed |