IP Library Granted Patent US 8,821,901
Granted Patent B2
US 8,821,901 · App. 12/754,331 · Granted Sep 2, 2014

Method of preparing polymeric adhesive compositions utilizing the mechanism of interaction between the polymer components

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Quick Facts
Patent No.
US 8,821,901
App. No.
12/754,331
Granted
Sep 2, 2014
Kind
B2
Abstract

A method of selecting components for use in water-absorbing pressure-sensitive adhesive compositions is provided. The method involves selecting a film-forming polymer, a ladder-like non-covalent crosslinker that is capable of forming a ladder-like interpolymer complex with the film-forming polymer selected, and selecting a carcass-like non-covalent crosslinker that is capable of forming a carcass-like complex with at least one of the film-forming polymer selected or the ladder-like non-covalent crosslinker selected. The adhesive hydrogels provide high adhesion in a swollen state and bridge the gap between conventional pressure sensitive adhesives and bioadhesives. Methods for preparing and using the resulting compositions are also disclosed.

Claims (29)

1. A method of preparing a bioadhesive, tooth whitening composition comprising:

(i) blending a mixture comprising a (1:1) methyacrylic acid-ethyl acrylate copolymer, polyvinylpyrrolidone, poly(ethylene glycol) having a molecular weight from 200-600, and a tooth whitening agent, to thereby form a blended polymer-tooth whitening agent composition, wherein the amount of polyvinylpyrrolidone on a weight basis is greater than the amount of the methyacrylic acid-ethyl acrylate copolymer or the amount of the poly(ethylene)glycol,

(ii). melting the blended polymer-tooth whitening agent composition from (i) to form a melted composition, and

(iii). extruding the melted composition from (ii) to form an extruded tooth whitening composition,

the extruded tooth whitening composition comprising from about 20-95 wt % polyvinylpyrrolidone, from about 0.5-40 wt % of methyacrylic acid-ethyl acrylate copolymer, and from about 0.5-60 wt % poly(ethylene glycol).

2. The method of claim 1 wherein the tooth whitening agent is selected from the group consisting of peroxides, metal chlorites, perborates, percarbonates, peroxyacids, and combinations thereof.

3. The method of claim 1 , wherein in step (iii), the melted composition is extruded onto a suitable substrate or backing member.

4. The method of claim 1 , wherein the extruded tooth whitening composition comprises about 30-50 wt % polyvinyl pyrrolidone; about 5-10 wt % (1:1) methyacrylic acid-ethyl acrylate copolymer; and about 15-30 wt % polyethylene glycol.

5. The method of claim 2 , wherein the tooth whitening agent is hydrogen peroxide.

6. The method of claim 5 , wherein the extruded tooth whitening composition comprises from about 5-25 wt % hydrogen peroxide.

7. The method of claim 1 , wherein the melting step is carried out at a temperature from about 90° C. to 170° C.

8. The method of claim 7 , wherein the melting step is carried out at a temperature from about 100° C. to 140° C.

9. The method of claim 1 , wherein additional components are present in the blended polymer-tooth whitening agent composition of step (i).

10. The method of claim 9 , wherein a solvent or water is additionally present in the blended polymer-tooth whitening agent composition of step (i).

11. The method of claim 1 , further comprising after the extruding step, pressing the extruded teeth whitening composition against a backing member.

12. The method of claim 1 , further comprising after the extruding step, laminating the extruded teeth whitening composition to a backing member.

13. The method of claim 3 , wherein the thickness of the resulting extruded teeth whitening composition ranges from about 0.050 to 0.80 millimeters.

14. The method of claim 1 , wherein the tooth whitening agent mixed in step (i) is in solid form.

15. The method of claim 1 , wherein the tooth whitening agent mixed in step (i) is dissolved in a solvent.

16. The method of claim 3 , further comprising adding a release liner to the melted composition that has been extruded onto a suitable substrate or backing member.

17. The method of claim 3 , wherein the backing member is erodible.

18. The method of claim 2 , wherein the tooth whitening agent is a peroxide.

19. The method of claim 5 , wherein the extruded tooth whitening composition comprises about 6 weight percent hydrogen peroxide.

20. The method of claim 1 , wherein the extruded bioadhesive tooth whitening composition formed in step (iii) is substantially non-tacky but exhibits adhesion upon contact with a moist surface.

21. In a method of preparing a bioadhesive, tooth whitening composition comprising the steps of:

(i) blending a (1:1) methyacrylic acid-ethyl acrylate copolymer, polyvinylpyrrolidone, and poly(ethylene glycol) having a molecular weight from 200-600, wherein the amount of polyvinylpyrrolidone on a weight basis is greater than the amount of the methyacrylic acid-ethyl acrylate copolymer or the amount of the poly(ethylene)glycol,

(ii). melting the blended composition from (i) to form a melted composition, and

(iii). extruding the melted composition from (ii) to form an, extruded composition,

the improvement comprising the inclusion of a tooth whitening agent directly in the blending step to form a blended polymer-tooth whitening agent composition, wherein the extruded tooth whitening composition comprises from about 20-95 wt % polyvinylpyrrolidone, from about 0.5-40 wt % of methyacrylic acid-ethyl acrylate copolymer, and from about 0.5-60 wt % poly(ethylene glycol).

Assignments (14)
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER PREVIOUSLY RECORDED AT REEL: 61852 FRAME: 207. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 30, 2025
From: CORIUM, INC.
To: CORIUM PHARMA SOLUTIONS, INC.
Reel/Frame 071915/0691 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2022
From: CORIUM, INC.
To: CORIUM PHARMA SOLUTIONS, INC.
Reel/Frame 062760/0731 →
RELEASE OF SECURITY INTEREST Recorded Oct 19, 2022
From: HERCULES CAPITAL, INC., AS AGENT
To: CORIUM, INC.
Reel/Frame 061713/0557 →
SECURITY INTEREST Recorded Oct 17, 2022
From: CORIUM PHARMA SOLUTIONS, INC.
To: SILICON VALLEY BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 061689/0581 →
RELEASE OF SECURITY INTEREST Recorded Oct 17, 2022
From: HERCULES CAPITAL, INC.
To: CORIUM, INC.
Reel/Frame 061687/0281 →
CHANGE OF NAME Recorded Oct 14, 2022
From: CORIUM, INC.
To: CORIUM PHARMA SOLUTIONS, INC.
Reel/Frame 061852/0207 →
SECURITY INTEREST Recorded Sep 24, 2021
From: CORIUM, INC.
To: HERCULES CAPITAL, INC., AS AGENT
Reel/Frame 057597/0907 →
CHANGE OF NAME Recorded Apr 9, 2019
From: CORIUM INTERNATIONAL, INC.
To: CORIUM, INC.
Reel/Frame 048841/0324 →
RELEASE OF SECURITY INTEREST Recorded Mar 6, 2018
From: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "B" (CAYMAN) L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 046909/0855 →
RELEASE OF SECURITY INTEREST Recorded Mar 6, 2018
From: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "B" (CAYMAN) L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 045513/0686 →
RELEASE OF SECURITY INTEREST Recorded Nov 27, 2017
From: SILICON VALLEY BANK
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 044229/0054 →
SECURITY INTEREST Recorded Dec 4, 2014
From: CORIUM INTERNATIONAL, INC.
To: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II ? PARALLEL FUND ?A? L.P.; CAPITAL ROYALTY PARTNERS II ? PARALLEL FUND ?B? (CAYMAN) L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.
Reel/Frame 034535/0238 →
SECURITY AGREEMENT Recorded Sep 10, 2012
From: CORIUM INTERNATIONAL, INC.
To: SILICON VALLEY BANK
Reel/Frame 028927/0365 →
SECURITY AGREEMENT Recorded Sep 4, 2012
From: CORIUM INTERNATIONAL, INC.
To: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
Reel/Frame 028895/0961 →