WO1994024177B1 - Crosslinked absorbent pressure sensitive adhesive and wound dressing - Google Patents
Crosslinked absorbent pressure sensitive adhesive and wound dressingInfo
- Publication number
- WO1994024177B1 WO1994024177B1 PCT/US1994/003881 US9403881W WO9424177B1 WO 1994024177 B1 WO1994024177 B1 WO 1994024177B1 US 9403881 W US9403881 W US 9403881W WO 9424177 B1 WO9424177 B1 WO 9424177B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- monomer
- sensitive adhesive
- acrylate
- pressure
- amendment
- Prior art date
Links
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract 7
- 239000002250 absorbent Substances 0.000 title claims abstract 4
- 230000002745 absorbent Effects 0.000 title claims abstract 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract 6
- 239000000203 mixture Substances 0.000 claims abstract 5
- 239000000853 adhesive Substances 0.000 claims abstract 3
- 230000001070 adhesive Effects 0.000 claims abstract 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 methacrylate ester Chemical class 0.000 claims abstract 3
- 239000000178 monomer Substances 0.000 claims 9
- 238000004132 cross linking Methods 0.000 claims 3
- 238000010521 absorption reaction Methods 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- GAVHQOUUSHBDAA-UHFFFAOYSA-N 3-butyl-1-ethenylaziridin-2-one Chemical compound CCCCC1N(C=C)C1=O GAVHQOUUSHBDAA-UHFFFAOYSA-N 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- RFJIPESEZTVQHZ-UHFFFAOYSA-N oxirane;prop-2-enoic acid Chemical group C1CO1.OC(=O)C=C RFJIPESEZTVQHZ-UHFFFAOYSA-N 0.000 claims 1
- 210000003491 Skin Anatomy 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 1
Abstract
Crosslinked, absorbent pressure sensitive adhesive compositions are disclosed comprising an acrylate or methacrylate ester of an alcohol, a hydrophilic alkylene oxide acrylate, a hydrophilic N-vinyl lactam, and an effective amount of a crosslinking agent. The compositions have an enhanced skin adhesion profile and are moderately absorbent. Also disclosed are precursor adhesive compositions and low-profile wound dressings.
Claims
1. An absorbent pressure-sensitive adhesive comprising a crosslinked copolymer of A, B, C and PX wherein the pressure-sensitive adhesive has a twenty four hour immersed absorption capacity (Imrs24) of at least 200 percent and further wherein:
(a) A is an acrylate monomer selected from the group consisting of (i) an acrylate or methacrylate ester of a non-tertiary C^ alcohol, and (ii) an acrylate or methacrylate ester of a mixture of non-tertiary C 14 alcohols with a resultant average of between about 4-12 carbon atoms per alcohol molecule;
(b) B is a hydrophilic alkylene oxide acrylate monomer having an average of about 3 to 40 alkylene oxide units;
(c) C is a hydrophilic N-vinyl lactam monomer; and
(d) PX is a crosslinking monomer effective for crosslinking the copolymer upon exposure to ultraviolet radiation.
2. The pressure-sensitive adhesive of claim 1 wherein monomer B is an ethylene oxide acrylate.
3. The pressure-sensitive adhesive of claim 1 wherein monomer C is selected from the group consisting of N-vinyl pyrrolidone, N-vinyl-2-caprolactam, and combinations thereof.
4. The pressure-sensitive adhesive of claim 1 wherein the adhesive comprises about 30 to 70 wt% monomer A, about 15 to 40 wt% monomer B, about 15 to 50 wt% monomer C, and about 0.01 to 2 wt% crosslinking monomer PX.
3 8
STATEMENT UNDER ARTICLE19
Claim 1 has been amended. Support for the amendment is found in the specification at page 14, lines 19-21 where it is stated that "the adhesive of the present invention possesses a twenty-four hour immersed absorption capacity..." Further support for the amendment is found in Table 2 (pp. 30-33) which include the MVTR T24 results from the Examples. No new matter is added by the amendment.
Applicant requests that the Examiner enter the amendment.
39
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52333094A JP3527241B2 (en) | 1993-04-14 | 1994-04-08 | Crosslinkable absorbent pressure sensitive adhesive and wound dressing |
| DE69403473T DE69403473T2 (en) | 1993-04-14 | 1994-04-08 | CROSS-LINKED ABSORBENT ADHESIVES AND Wound Bandage |
| EP94912971A EP0694045B1 (en) | 1993-04-14 | 1994-04-08 | Crosslinked absorbent pressure sensitive adhesive and wound dressing |
| CA002157296A CA2157296C (en) | 1993-04-14 | 1994-04-08 | Crosslinked absorbent pressure sensitive adhesive and wound dressing |
| HK98107039A HK1007752A1 (en) | 1993-04-14 | 1998-06-26 | Crosslinked absorbent pressure sensitive adhesive and wound dressing |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/047,637 US5407717A (en) | 1993-04-14 | 1993-04-14 | Crosslinked absorbent pressure sensitive adhesive and wound dressing |
| US08/047,637 | 1993-04-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1994024177A1 WO1994024177A1 (en) | 1994-10-27 |
| WO1994024177B1 true WO1994024177B1 (en) | 1994-11-24 |
Family
ID=21950077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/003881 WO1994024177A1 (en) | 1993-04-14 | 1994-04-08 | Crosslinked absorbent pressure sensitive adhesive and wound dressing |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5407717A (en) |
| EP (1) | EP0694045B1 (en) |
| JP (1) | JP3527241B2 (en) |
| CA (1) | CA2157296C (en) |
| DE (1) | DE69403473T2 (en) |
| HK (1) | HK1007752A1 (en) |
| WO (1) | WO1994024177A1 (en) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5731387A (en) * | 1994-07-11 | 1998-03-24 | Adhesives Research, Inc. | Ionically-crosslinked water-absorbent graft copolymer |
| US5726250A (en) * | 1994-07-11 | 1998-03-10 | Adhesives Research, Inc. | Covalently crosslinked water-absorbent graft copolymer |
| US5614310A (en) * | 1994-11-04 | 1997-03-25 | Minnesota Mining And Manufacturing Company | Low trauma wound dressing with improved moisture vapor permeability |
| US5733570A (en) * | 1996-09-05 | 1998-03-31 | Minnesota Mining And Manufacturing Company | Absorbent dressing |
| US6479073B1 (en) * | 1996-10-07 | 2002-11-12 | 3M Innovative Properties Company | Pressure sensitive adhesive articles and methods for preparing same |
| US6221997B1 (en) | 1997-04-28 | 2001-04-24 | Kimberly Ann Woodhouse | Biodegradable polyurethanes |
| US6420622B1 (en) | 1997-08-01 | 2002-07-16 | 3M Innovative Properties Company | Medical article having fluid control film |
| US6007532A (en) | 1997-08-29 | 1999-12-28 | 3M Innovative Properties Company | Method and apparatus for detecting loss of contact of biomedical electrodes with patient skin |
| US6356779B1 (en) | 1999-06-04 | 2002-03-12 | 3M Innovative Properties Company | Universally functional biomedical electrode |
| US6558790B1 (en) | 1999-11-30 | 2003-05-06 | Avery Dennison Corporation | Water vapor-permeable, pressure-sensitive adhesives |
| US6525129B1 (en) | 1999-12-20 | 2003-02-25 | Avery Dennison Corporation | Water-soluble pressure-sensitive adhesives |
| US7005143B2 (en) * | 2002-04-12 | 2006-02-28 | 3M Innovative Properties Company | Gel materials, medical articles, and methods |
| CN1324081C (en) * | 2002-07-03 | 2007-07-04 | 宝洁公司 | Radiation curable low stress relaxation elastomeric materials |
| US6613857B1 (en) | 2002-07-26 | 2003-09-02 | Avery Dennison Corporation | UV-crosslinked, pressure-sensitive adhesives |
| US20060229209A1 (en) * | 2002-12-02 | 2006-10-12 | Lysander Chrisstoffels | Copolymers based on n-vinylamide as adjuvants and agents for using in the agrotechnical field |
| US6939492B2 (en) * | 2002-12-26 | 2005-09-06 | Kimberly-Clark Worldwide, Inc. | Method for making fibrous web materials |
| US6825278B2 (en) * | 2003-01-16 | 2004-11-30 | Resolution Specialty Materials Llc | Modified pressure sensitive adhesive |
| US20050070688A1 (en) * | 2003-09-26 | 2005-03-31 | 3M Innovative Properties Company | Reactive hydrophilic oligomers |
| EA200900482A1 (en) * | 2006-10-05 | 2009-10-30 | Басф Се | BURNED POLYMERS AND THEIR APPLICATION FOR OBTAINING COMPOSITIONS OF ACTING OR EFFECTIVE SUBSTANCE |
| JP5426822B2 (en) * | 2006-11-07 | 2014-02-26 | コラノ・アクチェンゲゼルシャフト | Wound covering and method for producing the same |
| US20080300526A1 (en) * | 2007-06-01 | 2008-12-04 | Yulex Corporation | Guayule rubber and resin wet-stick bioadhesives |
| US8765217B2 (en) | 2008-11-04 | 2014-07-01 | Entrotech, Inc. | Method for continuous production of (meth)acrylate syrup and adhesives therefrom |
| US20100113692A1 (en) * | 2008-11-04 | 2010-05-06 | Mcguire Jr James E | Apparatus for Continuous Production of Partially Polymerized Compositions |
| KR20110105794A (en) * | 2008-12-12 | 2011-09-27 | 바스프 에스이 | Modified polyvinyllactams |
| US8329079B2 (en) * | 2009-04-20 | 2012-12-11 | Entrochem, Inc. | Method and apparatus for continuous production of partially polymerized compositions and polymers therefrom |
| EP2335661B1 (en) * | 2009-12-18 | 2012-12-12 | Paul Hartmann AG | Cutting aid for wound dressing for suppression therapy |
| US8541498B2 (en) | 2010-09-08 | 2013-09-24 | Biointeractions Ltd. | Lubricious coatings for medical devices |
| JP2016519171A (en) | 2013-03-14 | 2016-06-30 | スリーエム イノベイティブ プロパティズ カンパニー | Hydrocolloid wound dressings with elevated WVTR |
| US10617794B2 (en) * | 2015-02-23 | 2020-04-14 | Trustees Of Boston University | Macroinitiators for hydrophilic coatings on latex and applications thereof |
| WO2016204258A1 (en) * | 2015-06-19 | 2016-12-22 | 日産化学工業株式会社 | Polymer for gel formation and dermatological adhesive material |
| WO2017091515A1 (en) | 2015-11-24 | 2017-06-01 | University Of Washington | Photosensitive medical tape |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT610737A (en) * | 1955-11-18 | 1900-01-01 | ||
| US3121021A (en) * | 1960-04-18 | 1964-02-11 | Minnesota Mining & Mfg | Breathable surgical adhesive tapes |
| US3321451A (en) * | 1965-07-02 | 1967-05-23 | Johnson & Johnson | Adhesive compositions |
| GB1166682A (en) * | 1965-12-23 | 1969-10-08 | Johnson & Johnson | Pressure-Sensitive Acrylate Adhesives |
| US3532652A (en) * | 1966-07-14 | 1970-10-06 | Ppg Industries Inc | Polyisocyanate-acrylate polymer adhesives |
| JPS52774B2 (en) * | 1973-10-12 | 1977-01-10 | ||
| US4140115A (en) * | 1973-12-03 | 1979-02-20 | Johnson & Johnson | Pressure sensitive adhesive compositions for coating articles to be attached to skin |
| US4181752A (en) * | 1974-09-03 | 1980-01-01 | Minnesota Mining And Manufacturing Company | Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing |
| US4030639A (en) * | 1975-04-28 | 1977-06-21 | Pennwalt Corporation | Charcoal adsorber filter fill system |
| US4165266A (en) * | 1977-03-30 | 1979-08-21 | Union Carbide Corporation | Radiation curable pressure sensitive adhesive compositions |
| US4337325A (en) * | 1978-10-30 | 1982-06-29 | The Kendall Company | Pressure-sensitive adhesive |
| US4370380A (en) * | 1980-04-04 | 1983-01-25 | The Kendall Company | Pressure-sensitive adhesive |
| SU1243627A3 (en) * | 1979-12-05 | 1986-07-07 | Дзе Кендалл Компани (Фирма) | Jelly-forming composition |
| CA1192825A (en) * | 1980-11-10 | 1985-09-03 | Minnesota Mining And Manufacturing Company | Device and method for applying conformable, thin adhesive-coated films |
| CA1218954A (en) * | 1982-02-25 | 1987-03-10 | David L. Sieverding | Hydrophilic, elastomeric, pressure-sensitive adhesive |
| US4499896A (en) * | 1982-03-30 | 1985-02-19 | Minnesota Mining And Manufacturing Co. | Reservoir wound dressing |
| IN161966B (en) * | 1983-06-27 | 1988-03-05 | Johnson & Johnson Prod Inc | |
| USRE33353E (en) * | 1985-01-24 | 1990-09-25 | Minnesota Mining And Manufacturing Company | Thin film surgical dressing with delivery system |
| US5153040A (en) * | 1985-03-11 | 1992-10-06 | Minnesota Mining And Manufacturing Co. | Wound dressing |
| GB8611838D0 (en) * | 1986-05-15 | 1986-06-25 | Yarsley Technical Centre Ltd | Hydrophilic copolymers |
| US4737559A (en) * | 1986-05-19 | 1988-04-12 | Minnesota Mining And Manufacturing Co. | Pressure-sensitive adhesive crosslinked by copolymerizable aromatic ketone monomers |
| US4737410A (en) * | 1986-11-28 | 1988-04-12 | Minnesota Mining And Manufacturing Company | Polyalkyloxazoline-reinforced acrylic pressure-sensitive adhesive composition |
| US4871812A (en) * | 1986-11-28 | 1989-10-03 | Minnesota Mining And Manufacturing Company | Moldable medical adhesive |
| US5088483A (en) * | 1988-11-04 | 1992-02-18 | Minnesota Mining And Manufacturing Co. | Adhesive frame bandage |
| US5160315A (en) * | 1991-04-05 | 1992-11-03 | Minnesota Mining And Manufacturing Company | Combined adhesive strip and transparent dressing delivery system |
-
1993
- 1993-04-14 US US08/047,637 patent/US5407717A/en not_active Expired - Lifetime
-
1994
- 1994-04-08 EP EP94912971A patent/EP0694045B1/en not_active Expired - Lifetime
- 1994-04-08 WO PCT/US1994/003881 patent/WO1994024177A1/en active IP Right Grant
- 1994-04-08 JP JP52333094A patent/JP3527241B2/en not_active Expired - Fee Related
- 1994-04-08 CA CA002157296A patent/CA2157296C/en not_active Expired - Fee Related
- 1994-04-08 DE DE69403473T patent/DE69403473T2/en not_active Expired - Lifetime
-
1995
- 1995-01-17 US US08/373,586 patent/US5468821A/en not_active Expired - Lifetime
-
1998
- 1998-06-26 HK HK98107039A patent/HK1007752A1/en not_active IP Right Cessation
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