IP Library › Granted Patent US 10,729,806
Granted Patent B2
US 10,729,806 · App. 15/569,777 · Granted Aug 4, 2020

Adhesive composition

Inventors: Bahar Bingol (Copenhagen OE, DK); Kristoffer Hansen (Naerum, DK)
Assignee: Coloplast A/S
A61L24/043A61F5/443A61L24/001A61L24/0021A61L24/0031A61L24/0089A61M27/00C09J183/04A61L2400/14A61M25/0017C08G77/16C08G77/18
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Quick Facts
Patent No.
US 10,729,806
App. No.
15/569,777
Granted
Aug 4, 2020
Kind
B2
Abstract

Moisture-curable adhesive compositions, their preparation and use are disclosed herein. The moisture-curable adhesive compositions include one or more reactive polymers, such as reactive silicone polymers, one or more adhesive components, such as a silicone pressure sensitive polymer(s) (PSAs), a cross-linker and a catalyst. Typically, the reactive silicone polymer or polymers are hydroxyl terminated polydimethylsiloxanes (PDMS) having at least two hydroxyl functionalities associated with the polymer(s).

Claims (60)

1. A moisture-curable adhesive composition comprising:

a reactive component, wherein the reactive component comprises a reactive silicone polymer or a mixture of reactive silicone polymers;

an adhesive component, wherein the adhesive component comprises a cured polycondensed organopolysiloxane resin that is a reaction product or products of a silanol terminated organopolysiloxane and a silicate organopolysiloxane resin containing at least one RSiO 3/2 or SiO 4/2 siloxyl unit, wherein each R, individually, is H, an alkyl group, aryl group, a reactive functional group or an alkoxy group;

a cross-linker;

a catalyst; and

a hydrocolloid, wherein the hydrocolloid is selected from guar gum, locust bean gum, pectin, potato starch, alginates, gelatine, xanthan or gum karaya, cellulose derivatives, salts of carboxymethyl cellulose, sodium carboxymethyl cellulose, methyl cellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, sodium starch glycolate, polyvinylalcohol, and mixtures thereof.

2. The moisture-curable adhesive composition according to claim 1 , wherein the reactive silicone polymer or mixture of reactive silicone polymers comprises a polysiloxane of the formula (I):

X—R 1 R 2 Si—(O—SiR 1 R 2 ) n —Y  (I)

wherein X and Y are OH;

wherein R 1 and R 2 independently are the same or different and selected form the group consisting of C 1 -C 10 alkyl, C 1 -C 10 alkyl substituted at one or more carbons with one or more halogen atoms, C 1 -C 18 alkyl substituted at one or more carbons with a cyano (—CN) group, phenyl, and phenyl substituted at one or more carbons with a halogen atom or a cyano group; and

wherein n is a number from 1 to 10,000.

3. The moisture-curable adhesive composition according to claim 1 , wherein the reactive silicone polymer or mixture of reactive silicone polymers comprises a polysiloxane of the formula (II):

(R 3 O) m —Si(R 4 ) 3-m —(O—SiR 1 R 2 ) n —Si(R 4 ) 3-k —(OR 3 ) k   (II)

wherein k and m independently are integers from 0 to 3, provided that k+m>0;

wherein R 1 , R 2 , and R 4 independently are the same or different and selected form the group consisting of C 1 -C 10 alkyl, C 1 -C 10 alkyl substituted at one or more carbons with one or more halogen atoms, C 1 -C 18 alkyl substituted at one or more carbons with a cyano (—CN) group, phenyl, and phenyl substituted at one or more carbons with a halogen atom or a cyano group;

wherein R 3 is C 1 -C 10 alkyl; and

wherein n is a number from 1 to 10,000.

4. The moisture-curable adhesive composition according to claim 1 , wherein the reactive silicone polymer or mixture of reactive silicone polymers comprises a polysiloxane of the formula (III):

W—Z—W  (III)

wherein W is selected from the group consisting of —Si(R1)2OH and —Si(R″)2-(D)d-R′″—SiR″k(OR5)3-k, wherein R 1 is selected from the group consisting of C 1 -C 10 alkyl, C 1 -C 10 alkyl substituted at one or more carbons with one or more halogen atoms, C 1 -C 18 alkyl substituted at one or more carbons with a cyano (—CN) group, phenyl, and phenyl substituted at one or more carbons with a halogen atom or a cyano group; wherein D is —R′″—(Si(R″)2-O)r-Si(R″)2- and R″ is selected from the group consisting of a C 1 -C 6 alkyl, a vinyl group, a phenyl group, and a fluorinated C 1 -C 6 alkyl, R′″ is a divalent hydrocarbon group, r is an integer between 1 and 6, and d is 0 or an integer from 1 to 100, R5 is a C 1 -C 6 alkyl or alkoxy group, and k has is 0, 1 or 2;

wherein Z is a linear polysiloxane polymer backbone.

5. The moisture-curable adhesive composition according to claim 4 , wherein Z is a polysiloxane of the formula (IV):

—[SiO (4-p)/2 (R 1 ) p ] b —  (IV)

wherein b is an integer from 50 to 5,000, p is on average 1.9-2.0, and R 1 is selected form the group consisting of C 1 -C 10 alkyl, C 1 -C 10 alkyl substituted at one or more carbons with one or more halogen atoms, C 1 -C 18 alkyl substituted at one or more carbons with a cyano (—CN) group, phenyl, and phenyl substituted at one or more carbons with a halogen atom or a cyano group.

6. The moisture-curable adhesive composition according to claim 1 , wherein the silanol terminated organopolysiloxane comprises a structure:

wherein R 1 is OH;

R 2 is methyl, phenyl, or vinyl; and

n is from 1 to 500.

7. The moisture-curable adhesive composition according to claim 1 , wherein the cross-linker contains at least two hydrolysable groups and is selected from the group consisting of a silicone, an organic polymer, a monosilane molecule, and a disilane molecule.

8. The moisture-curable adhesive composition according to claim 1 , wherein the cross-linker is a monosilane of the formula (V):

R IV 4-q Si(OR 5 ) q   (V)

wherein R IV is an organic radical selected from the group consisting of linear alkyl, branched alkyl, allyl, phenyl, substituted phenyl, acethoxy, and oxime;

wherein R 5 is selected from the group consisting of hydrogen, methyl, and ethyl; and

wherein q is 0 or an integer from 1 to 4, or

wherein the cross-linker is a disilane of the formula (VI):

Si(OR 7 ) t R V Si(OR 7 ) q   (VI)

wherein t and q independently are integers from 1 to 3;

wherein R V is an organic or poly-siloxane-based moiety; and

wherein R 7 is selected from the group consisting of hydrogen, methyl, and ethyl.

9. The moisture-curable adhesive composition according to claim 1 , wherein the cross-linker is selected from the group consisting of methyltri(methoxy)silane (MTM), vinyltrimethoxysilane, methyltriethoxysilane, vinyltriethoxysilane, isobutyltrimethoxysilane (iBTM), ethyltrimethoxysilane, vinyltriethoxysilane, phenyltrimethoxysilane, oximosilanes, acetoxy silane, acetonoxime silane, and enoxy silane.

10. The moisture-curable adhesive composition according to claim 1 , wherein the catalyst is a metal-containing catalyst comprising a metal selected from the group consisting of tin, lead, antimony, iron, cadmium, barium, manganese, zinc, chromium, cobalt, nickel, aluminium, gallium, germanium, titanium and zirconium.

11. The moisture-curable adhesive composition according to claim 10 , wherein the catalyst is a titanium catalyst.

12. The moisture-curable adhesive composition according to claim 1 , wherein the hydrocolloid is present in an amount from 30 weight percent to 50 weight percent.

13. The moisture-curable adhesive composition according to claim 1 , further comprising an adhesion promoter.

14. The moisture-curable adhesive composition according to claim 13 , wherein the adhesion promoter is 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 2-3(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, or methacryloxypropyltrimethoxysilane.

15. The moisture-curable adhesive composition according to claim 1 , wherein the adhesive composition is a one-part curable composition.

16. A method to prepare a moisture-curable adhesive composition according to claim 1 , comprising the step:

providing one or more reactive silicone polymers;

combining the one or more reactive silicone polymer(s) with a cured polycondensed organopolysiloxane resin that is a reaction product or products of a silanol terminated organopolysiloxane and a silicate organopolysiloxane resin containing at least one RSiO 3/2 or SiO 4/2 siloxyl unit, wherein each R, individually, is H, an alkyl group, aryl group, a reactive functional group or an alkoxy group, a cross-linker; a source of moisture; and a catalyst to form the moisture-curable adhesive composition.

17. A method to releasably and adhesively attach a medical device to a skin surface comprising the steps:

providing a medical device comprising a moisture-curable adhesive composition without water, the moisture-curable adhesive composition comprising a reactive component, wherein the reactive component comprises a reactive silicone polymer or a mixture of reactive silicone polymers; an adhesive component, wherein the adhesive component comprises a cured polycondensed organopolysiloxane resin that is a reaction product or products of a silanol terminated organopolysiloxane and a silicate oranopolysiloxane resin containing at least one RSiO 3/2 or SiO 4/2 siloxyl unit, wherein each R, individually, is H, an alkyl group, aryl group, a reactive functional group or an alkoxy group; a cross-linker; and a catalyst;

applying the moisture-curable adhesive to the skin surface;

exposing the moisture-curable adhesive to moisture, thereby switching the moisture-curable adhesive from a liquid state to an adhesive state.

18. A packaged product comprising:

a moisture-curable adhesive composition comprising a reactive component, wherein the reactive component comprises a reactive silicone polymer or a mixture of reactive silicone polymers;

an adhesive component, wherein the adhesive component comprises a cured polycondensed organopolysiloxane and a silicate oranopolysiloxane resin containing at least one RSiO 3/2 or SiO 4/2 siloxyl unit, wherein each R, individually, is H, an alkyl group, aryl group, a reactive functional group or an alkoxy group;

a cross-linker;

and a catalyst; and

instructions to apply the moisture-curable composition to a skin surface in the presence of moisture.

19. The packaged product according to claim 18 , wherein the packaged product further comprises a medical device associated with the packaged product, wherein the medical device is an ostomy device.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 27, 2017
From: BINGOL, BAHAR; HANSEN, KRISTOFFER
To: COLOPLAST A/S
Reel/Frame 043964/0401 →
Priority Claims (3)
DK 2015 70255 · Apr 30, 2015 · national
WO PCT/DK2015/050305 · Oct 8, 2015 · international
DK 2016 70225 · Apr 13, 2016 · national
Continuity (1)
Related Publication 20180133360A1 · May 17, 2018
Cited By (6)
US 12,186,228 US 12,193,964 US 12,357,494 US 12,427,049 US 12,668,698 US 12,668,726