IP Library Granted Patent US 11,045,576
Granted Patent B2
US 11,045,576 · App. 15/517,519 · Granted Jun 29, 2021

Composition comprising a polymer and a switch initiator

Inventors: Peter Kwok Hing Lam (Frederiksberg C, DK); Esben Stroebech (Hoersholm, DK); Kristoffer Hansen (Naerum, DK); Anders Grove Sund (Dyssegaard, DK); Anca Gabriela Bejenariu (Koebenhavn S, DK); Charlotte Juel Fristrup (Virum, DK); Bahar Bingol (Copenhagen OE, DK)
Assignee: Coloplast A/S
A61L24/0031A61F5/443A61L24/043A61L2400/14
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Quick Facts
Patent No.
US 11,045,576
App. No.
15/517,519
Granted
Jun 29, 2021
Kind
B2
Abstract

Disclosed is a composition including a polymer and a switch initiator. The composition can be switched from a first liquid state to a second adhesive state by activation of the switch initiator. The composition has in the first liquid state a complex viscosity |η*| below 0.4 MPa s; and the composition has in the second adhesive state a second repeated peel force above 1 N/25 mm.

Claims (36)

1. A switchable adhesive composition comprising a polymer, a photo-crosslinkable polyurethane, and a hydrocolloid, wherein the switchable adhesive composition can be switched from a liquid state to an adhesive state by activation of the photo-crosslinkable polyurethane; the switchable adhesive composition

having in the liquid state a complex viscosity |η*| below 0.4 MPa s; and

having in the adhesive state a higher complex viscosity |η*| than the complex viscosity |η*| of the liquid state, and having in the adhesive state a repeated peel force above 1 N/25 mm.

2. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the adhesive state has a first peel force above 1 N/25 mm.

3. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the adhesive state has a first peel force and wherein the repeated peel force is at least 50% of the first initial peel force.

4. The switchable adhesive composition according to claim 1 , wherein the polymer is an acrylate polymer or an acrylate copolymer.

5. The switchable adhesive composition according to claim 4 , wherein the acrylate polymer or acrylate copolymer comprises monomer units selected from ethyl acrylate, butyl acrylate, ethylhexyl acrylate, hydroxyethyl acrylate, lauryl acrylate, and acrylic acid.

6. The switchable adhesive composition according to claim 1 , wherein the polymer is a polyurethane.

7. The switchable adhesive composition according to claim 6 , wherein the polyurethane comprises a diisocyante selected from the group consisting of cycloaliphatic isocyanates, 4,4′-Methylenebis(cyclohexyl isocyanate) (HMDI), isophore diisocyanate, aromatic isocyanates, tolylene diisocyanate, 4,4′-diphenyl methyl diisocyanate (MDI), aliphatic isocyanates, and 1,6-hexane diisocyanate.

8. The switchable adhesive composition according to claim 6 , wherein the polyurethane comprises a diol of polydimethylsiloxane (PDMS) based polyols, bis(hydroxyalkyl) terminated PDMS, 4-{3-[bis(2-hydroxyethyl)amino]propoxy}-1-chloro-9H-thioxanthen-9-one (thioxanthone diol) and mixtures thereof.

9. The switchable adhesive composition according to claim 1 , wherein the photo-crosslinkable polyurethane comprises a free radical generating photoinitiator.

10. The switchable adhesive composition according to claim 1 , wherein the photo-crosslinkable polyurethane includes a photoinitiator moiety comprising an α-hydroxyketone, a benzophenone, benzophenone derivatives, a benzophenone/α-hydroxyketone, phenylglyoxylate, a benzyldimethyl-ketal, an aminoketone, acylphosphine derivatives, mono acyl phosphine (MAPO), MAPO/α-hydroxyketone, bis acyl phosphine (BAPO), a BAPO dispersion, a BAPO/α-hydroxyketone, phosphine oxide, a metallocene, an ionium salt, thioxanthone derivatives, a mixture of triarylsulphonium hexafluorophosphate salts in propylene carbonate, a mixture of triarylsulphonium hexafluoroantimonate salts in propylene carbonate, amphorquinone derivatives, benzil derivatives, anthraquinone derivatives, benzoin ether derivatives, polysilanes, and mixtures thereof.

11. The switchable adhesive composition according to claim 1 , wherein the activation of the photo-crosslinkable polyurethane is caused by exposure of the photo-crosslinkable polyurethane to visible light and/or ultraviolet light.

12. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition comprises the hydrocolloid in an amount of 1-60% (w/w) of the switchable adhesive composition.

13. The switchable adhesive composition according to claim 1 , wherein the hydrocolloid is a guar gum, a locust bean gum, a pectin, a potato starch, alginates, a gelatine, a xantan, a gum karaya, cellulose derivatives, salts of carboxymethyl cellulose, a sodium carboxymethyl cellulose, a methyl cellulose, a hydroxypropyl cellulose, a hydroxyethyl cellulose, a sodium starch glycolate, polyvinylalcohol, and mixtures thereof.

14. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the liquid state has moisture absorption of at least 0.1 g/cm 3 /2 h.

15. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the adhesive state has moisture absorption of at least 0.05 g/cm 3 /2 h.

16. The switchable adhesive composition according to claim 1 , wherein the moisture absorption of the switchable adhesive composition in the liquid state is higher than the absorption of the moisture in the adhesive state.

17. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the liquid state and/or the adhesive state is moisture vapor permeable.

18. The switchable adhesive composition according to claim 1 , wherein the moisture vapor transmission rate (MVTR) of the switchable adhesive composition in the liquid state is above 250 g/m 2 /24 h.

19. The switchable adhesive composition according to claim 1 , wherein the moisture vapor transmission rate (MVTR) of the switchable adhesive composition in the adhesive state is above 250 g/m 2 /24 h.

20. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the adhesive state has a G′ in the range 10 3 -10 5 Pa at 1 Hz.

21. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the adhesive state has a G″ in the range 10 3 -10 5 Pa at 1 Hz.

22. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the liquid state has a complex viscosity |η*| below 0.1 MPa s.

23. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the adhesive state has a complex viscosity that is at least 2 times higher than the complex viscosity of the switchable adhesive composition in the liquid state.

24. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition in the liquid state has a lower cohesion than the switchable adhesive composition in the adhesive state.

25. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition is hydrophobic.

26. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition is hydrophilic.

27. The switchable adhesive composition according to claim 1 , wherein the polymer forms a hydrophobic polymer matrix.

28. The switchable adhesive composition according to claim 1 , wherein the switchable adhesive composition is a one-component switchable adhesive composition.

29. The switchable adhesive composition according to claim 1 , wherein the complex viscosity |η*| is measured on 1 mm thick 25 mm diameter sample in a Haake RheoStress 6000 rotational rheometer, wherein the geometry applied was parallel plates 25 mm, the shear stress was fixed at 5556 Pa, and a gap size of 0.9-1.05 mm was applied to the sample in the beginning of the measurement to obtain a normal force of approximately 5 N, and wherein the measurements were carried out at 32° C. and at a frequency of 0.01 Hz.

30. The switchable adhesive composition according to claim 1 , wherein the repeated peel force is measured on a sample of 25×100 mm with a 25×300 mm piece of tape added on the top of the switchable adhesive composition, wherein the measurement is carried out after 30 minutes of conditioning at 23° C. and at 50% relative humidity with the sample mounted in a tensile testing machine (INSTRON 5564) and a 90-degree peel test performed from a Teflon substrate at a speed of 304 mm/min.

31. A re-attachable ostomy device comprising:

an ostomy device having a switchable adhesive composition disposed thereon,

wherein the switchable adhesive composition comprises a polymer, a photo-crosslinkable polyurethane, and a hydrocolloid, wherein the switchable adhesive composition can be switched from a liquid state to an adhesive state by activation of the photo-crosslinkable polyurethane; the switchable adhesive composition having in the liquid state a complex viscosity |η*| below 0.4 MPa s; and

having in the adhesive state a higher complex viscosity |η*| than the complex viscosity |η*| of the liquid state, and having in the adhesive state a repeated peel force above 1 N/25 mm.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 23, 2020
From: HING LAM, PETER KWOK; STROEBECH, ESBEN; HANSEN, KRISTOFFER; SUND, ANDERS GROVE; BEJENARIU, ANCA GABRIELA; FRISTRUP, CHARLOTTE JUEL; BINGOL, BAHAR
To: COLOPLAST A/S
Reel/Frame 053286/0301 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 23, 2018
From: LAM, PETER KWOK HING; STROEBECH, ESBEN; HANSEN, KRISTOFFER; SUND, ANDERS GROVE; BEJENARIU, ANCA GABRIELA; FRISTRUP, CHARLOTTE JUEL; BINGOL, BAHAR
To: COLOPLAST A/S
Reel/Frame 046421/0474 →
Priority Claims (6)
DK PA 2014 70626 · Oct 9, 2014 · national
DK PA 2014 70770 · Dec 9, 2014 · national
DK PA 2015 70057 · Feb 2, 2015 · national
DK PA 2015 70166 · Mar 24, 2015 · national
DK PA 2015 70210 · Apr 10, 2015 · national
DK PA 2015 70255 · Apr 30, 2015 · national
Continuity (1)
Related Publication 20170239384A1 · Aug 24, 2017