US6183593B1
Expired / Lapsed
US
⏱️ 0.0 years remaining
1,1-disubstituted ethylene adhesive compositions containing polydimethylsiloxane
Assignee: Ethicon Inc
•
Filing: 1999-12-23
•
Granted: 2001-02-06
•
Expires: 2019-12-23
Abstract
Abstract An adhesive composition that contains cyanoacrylate monomers and cyclic or alkyl- or phenyl-terminated linear polydimethylsiloxane is particularly useful in applications requiring flexibility and elasticity.
Inventors
- 👤 Upvan Narang
- 👤 William S. C. Nicholson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:15
CPC Classifications
A; A61; A61L; A61L15/00; A61L15/16; A61L15/42; A61L15/58; A61L15/585; A61P; A61P17/00; A61P17/02; A61P41/00; C; C09; C09D; C09D4/00; C09J; C09J4/00
Claims Analysis
Total Claims: 63
Claim 1
Independent Claim
48 words
An adhesive composition, comprising polydimethylsiloxane and polymerizable 1,1-disubstituted ethylene adhesive monomer; wherein said composition is substantially free of silanes, said polydimethylsiloxane is dissolved in, or in a microemulsion in, said monomer; said polydimethylsiloxane is cyclic, or alkyl- or phenyl-terminated linear, polydimethylsiloxane; and said polydimethylsiloxane is optionally alkyl substituted.
Claim 2
Dependent Claim
48 words
An adhesive composition, comprising polydimethylsiloxane and polymerizable 1,1-disubstituted ethylene adhesive monomer; wherein said composition is substantially free of silanes, said polydimethylsiloxane is dissolved in, or in a microemulsion in, said monomer; said polydimethylsiloxane is cyclic, or alkyl- or phenyl-terminated linear, polydimethylsiloxane; and said polydimethylsiloxane is optionally alkyl substituted.
Claim 3
Dependent Claim
12 words
The composition of claim 1 , wherein said monomer is α-cyanoacrylate monomer.
Claim 4
Dependent Claim
13 words
The composition of claim 1 , wherein said monomer is alkyl α-cyanoacrylate monomer.
Claim 5
Dependent Claim
27 words
The composition of claim 1 , wherein said monomer comprises at least one member selected from the group consisting of ethyl cyanoacrylate, butyl cyanoacrylate, and 2-octyl cyanoacrylate.
Claim 6
Dependent Claim
11 words
The composition of claim 1 , wherein said polydimethylsiloxane is linear.
Claim 7
Dependent Claim
17 words
The composition of claim 5 , wherein said polydimethylsiloxane has an average of about 2-12 monomer units.
Claim 8
Dependent Claim
17 words
The composition of claim 5 , wherein said polydimethylsiloxane has an average of about 3-4 monomer units.
Claim 9
Dependent Claim
14 words
The composition of claim 1 , wherein said polydimethylsiloxane is linear trimethylsiloxy terminated polydimethylsiloxane.
Claim 10
Dependent Claim
22 words
The composition of claim 1 , wherein said polydimethylsiloxane has a weight average molecular weight of from about 150 to about 1500.
Claim 11
Dependent Claim
20 words
The composition of claim 5 , wherein said polydimethylsiloxane has a viscosity of less than 8 centipoise at 25° C.
Claim 12
Dependent Claim
11 words
The composition of claim 1 , wherein said polydimethylsiloxane is cyclic.
Claim 13
Dependent Claim
17 words
The composition of claim 11 , wherein said polydimethylsiloxane has an average of about 3-12 monomer units.
Claim 14
Dependent Claim
24 words
The composition of claim 1 , wherein said polydimethylsiloxane is at least one member selected from the group consisting of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane.
Claim 15
Dependent Claim
34 words
The composition of claim 1 , wherein said polydimethylsiloxane is present in the composition in an amount of between about 5% and about 30% by weight relative to the total monomer and polydimethylsiloxane content.
Claim 16
Dependent Claim
18 words
The composition of claim 14 , wherein said amount is between about 10% and about 25% by weight.
Claim 17
Dependent Claim
14 words
The composition of claim 14 , wherein said amount is about 10-20% by weight.
Claim 18
Dependent Claim
11 words
The composition of claim 5 , wherein said polydimethylsiloxane is alkyl-terminated.
Claim 19
Dependent Claim
16 words
The composition of claim 5 , wherein said polydimethylsiloxane has methyl, ethyl or propyl terminal groups.
Claim 20
Dependent Claim
12 words
The composition of claim 5 , wherein said polydimethylsiloxane is methyl terminated.
Claim 21
Dependent Claim
11 words
The composition of claim 1 , wherein said polydimethylsiloxane is unsubstituted.
Claim 22
Dependent Claim
13 words
The composition of claim 1 , wherein said composition is free of silica.
Claim 23
Dependent Claim
16 words
The composition of claim 1 , wherein said composition further comprises at least one stabilizing agent.
Claim 24
Dependent Claim
16 words
The composition of claim 1 , further comprising at least one plasticizer different from said polydimethylsiloxane.
Claim 25
Dependent Claim
24 words
The composition of claim 23 , wherein said plasticizer is selected from the group consisting of tributyl citrate, acetyl tributyl citrate, polymethylmethacrylate and hexadimethylsilazane.
Claim 26
Dependent Claim
37 words
The composition of claim 23 , wherein a viscosity of said composition is at least 100 centipoise at 25° C. and said plasticizer is at least one member selected from the group consisting of polymethylmethacrylate and hexadimethylsilazane.
Claim 27
Dependent Claim
22 words
The composition of claim 1 , further comprising at least one antimicrobial preservative selected from the group consisting of cresols and parabens.
Claim 28
Dependent Claim
11 words
The composition of claim 1 , wherein said composition is sterile.
Claim 29
Dependent Claim
12 words
The composition of claim 1 , packaged in a post-fluorinated polymeric container.
Claim 30
Dependent Claim
25 words
A method of making the composition of claim 1 , comprising dissolving a polydimethylsiloxane in a polymerizable 1,1-disubstituted ethylene adhesive monomer to form a solution.
Claim 31
Dependent Claim
20 words
The method of claim 29 , wherein the polydimethylsiloxane is at least 98.5% by weight pure prior to said mixing.
Claim 32
Dependent Claim
11 words
The method of claim 29 , wherein the polydimethylsiloxane is cyclic.
Claim 33
Dependent Claim
11 words
The method of claim 29 , further comprising sterilizing said solution.
Claim 34
Dependent Claim
14 words
An adhesive composition comprising a polymerizable 1,1-disubstituted ethylene adhesive monomer and a cyclic polydimethylsiloxane.
Claim 35
Dependent Claim
14 words
An adhesive composition comprising a polymerizable 1,1-disubstituted ethylene adhesive monomer and a cyclic polydimethylsiloxane.
Claim 36
Dependent Claim
12 words
The composition of claim 33 , wherein said monomer is α-cyanoacrylate monomer.
Claim 37
Dependent Claim
13 words
The composition of claim 33 , wherein said monomer is alkyl α-cyanoacrylate monomer.
Claim 38
Dependent Claim
27 words
The composition of claim 33 , wherein said monomer comprises at least one member selected from the group consisting of ethyl cyanoacrylate, butyl cyanoacrylate, and 2-octyl cyanoacrylate.
Claim 39
Dependent Claim
24 words
The composition of claim 33 , wherein said polydimethylsiloxane is at least one member selected from the group consisting of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane.
Claim 40
Dependent Claim
20 words
The composition of claim 33 , wherein the cyclic polydimethylsiloxane has a viscosity of about 5-7.5 centipoise at 25° C.
Claim 41
Dependent Claim
45 words
An adhesive composition comprising: (a) 2-alkyl cyanoacrylate 65-90 wt %; (b) cyclic polydimethylsiloxane 10-35 wt %; (c) plasticizer 0-10 wt %; (d) anionic stabilizer 0-1 wt %; (e) radical stabilizer 0-1 wt %; (f) antimicrobial preservative 0-1 wt %; and (g) colorant 0-0.01 wt %.
Claim 42
Dependent Claim
45 words
An adhesive composition comprising: (a) 2-alkyl cyanoacrylate 65-90 wt %; (b) cyclic polydimethylsiloxane 10-35 wt %; (c) plasticizer 0-10 wt %; (d) anionic stabilizer 0-1 wt %; (e) radical stabilizer 0-1 wt %; (f) antimicrobial preservative 0-1 wt %; and (g) colorant 0-0.01 wt %.
Claim 43
Dependent Claim
19 words
The composition of claim 39 , wherein said alkyl cyanoacrylate is 2-octyl cyanoacrylate and said cyclic polydimethylsiloxane is octamethyltetracyclosiloxane.
Claim 44
Dependent Claim
24 words
The composition of claim 40 , wherein said plasticizer is selected from the group consisting of polymethylmethacrylate, hexadimethylsilazane, tributyl citrate and acetyl tributyl citrate.
Claim 45
Dependent Claim
12 words
The composition of claim 40 , wherein said preservative is methyl paraben.
Claim 46
Independent Claim
32 words
A method of making a sterile composition comprising: placing a mixture of a polymerizable cyanoacrylate monomer and a polydimethylsiloxane in a container, sealing said container, and sterilizing the mixture in the container.
Claim 47
Independent Claim
32 words
A method of making a sterile composition comprising: placing a mixture of a polymerizable cyanoacrylate monomer and a polydimethylsiloxane in a container, sealing said container, and sterilizing the mixture in the container.
Claim 48
Dependent Claim
11 words
The method of claim 43 , wherein said polydimethylsiloxane is cyclic.
Claim 49
Dependent Claim
20 words
The method of claim 43 , wherein said polydimethylsiloxane is selected from the group consisting of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane and dodecamethylcyclohexasiloxane.
Claim 50
Dependent Claim
26 words
The method of claim 43 , wherein said sterilizing is performed by dry heat, moist heat, retort canning, gamma irradiation, electron beam irradiation, or microwave irradiation.
Claim 51
Dependent Claim
15 words
The method of claim 43 , wherein said sterilizing is performed by electron beam irradiation.
Claim 52
Dependent Claim
15 words
A method of treating tissue, comprising applying the composition of claim 1 to said tissue.
Claim 53
Dependent Claim
18 words
The method of claim 48 , wherein said tissue is at or adjacent a joint of a mammal.
Claim 54
Dependent Claim
15 words
The method of claim 49 , wherein said joint is a human knee or elbow.
Claim 55
Dependent Claim
16 words
The method of claim 49 , wherein said joint is on a human hand or foot.
Claim 56
Dependent Claim
14 words
The method of claim 48 , wherein said tissue is on a human face.
Claim 57
Dependent Claim
17 words
The method of claim 48 , wherein said monomer is 2-octyl cyanoacrylate and said polydimethylsiloxane is cyclic.
Claim 58
Dependent Claim
11 words
The method of claim 48 , wherein said tissue is compromised.
Claim 59
Dependent Claim
16 words
The method of claim 54 , wherein said tissue is burned, lacerated, irritated, abraded or incised.
Claim 60
Dependent Claim
11 words
The method of claim 48 , wherein said tissue is skin.
Claim 61
Dependent Claim
11 words
The method of claim 56 , wherein said skin is compromised.
Claim 62
Dependent Claim
11 words
The method of claim 56 , wherein said skin is intact.
Claim 63
Dependent Claim
20 words
A polymer film formed by polymerizing the monomer of a film of an adhesive composition according to claim 1 .
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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) | 2004-02-06 | 2004-08-07 | 2005-02-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2008-02-06 | 2008-08-07 | 2009-02-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2012-02-06 | 2012-08-07 | 2013-02-06 | $7700.00 | Window Closed / Lapsed |