WO2012103181A1 - Methods to improve the blending of amphiphilic copolymers such as tris-nipam into silicone gel adhesive - Google Patents

Methods to improve the blending of amphiphilic copolymers such as tris-nipam into silicone gel adhesive Download PDF

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Publication number
WO2012103181A1
WO2012103181A1 PCT/US2012/022498 US2012022498W WO2012103181A1 WO 2012103181 A1 WO2012103181 A1 WO 2012103181A1 US 2012022498 W US2012022498 W US 2012022498W WO 2012103181 A1 WO2012103181 A1 WO 2012103181A1
Authority
WO
WIPO (PCT)
Prior art keywords
copolymer
nipam
silicone gel
silicone
blending
Prior art date
Application number
PCT/US2012/022498
Other languages
French (fr)
Inventor
Mahesh Sambasivam
Ann Beal Salamone
Joseph C. Salamone
Xiang Yu
Original Assignee
Convatec Technologies Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Convatec Technologies Inc. filed Critical Convatec Technologies Inc.
Publication of WO2012103181A1 publication Critical patent/WO2012103181A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
    • A61L24/043—Mixtures of macromolecular materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/068—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/28—Non-macromolecular organic substances
    • C08L2666/38—Sulfur-, selenium- or tellurium-containing compounds

Definitions

  • copolymer compatibility in the silicone gel prior to cure can be improved by one or more of the following methods: Copolymer Molecular weight and its composition:
  • the molecular weight and its distribution can have a significant impact on compatibility with silicone gel. Lower molecular weights of the copolymer with broader distribution are preferred. In addition, increasing the TRIS component should improve the compatibility.
  • Solvents with solubility parameter similar to the copolymer and the silicone are preferred.
  • the preferred solvent solubility parameter range is 7-10.
  • suitable solvents are ethyl acetate, hexamethydisiloxane, acetone, toluene, and tetrahydrofuran.
  • the copolymer is initially dissolved in the solvent(s) and mixed thoroughly.
  • the polymer solution is then added to the uncured gel with Part A and Part B, which are separately mixed together thoroughly before adding the polymer solution.
  • the copolymers could be diblocks, triblocks, random blocks, star shaped, or combed, or a combination.
  • Examples of such copolymers are poly(TRIS-b- NIPAM), and poly(dimethylsiloxane-b-1-ethoxyethyl methacrylate) (from Polymer Source Inc.).
  • the copolymer is a solid.
  • Silicone or non-silicone based surfactants Silicone or non-silicone based surfactants.
  • the temperature and shear rate during mixing of the copolymer into the gel is critical.
  • a lower mixing temperature can favor the stability of the gel but can affect the solubility of the copolymer in the selected solvent or gel.
  • Higher shear rates can improve the mixing process.
  • adding the copolymer slowly into the gel is preferred.

Abstract

The blending of TRIS-NIPAM copolymer into a silicone gel adhesive could be difficult depending on the amount of NIPAM co-monomer present in the copolymer. This is due to the chemical incompatibility between NIPAM segment of the copolymer and silicone gel. To facilitate blending of the copolymer into silicone gel prior to cure, and to obtain a useful gel with suitable properties after cure, it is necessary to incorporate additives during the blending process that are compatible with silicone and the copolymer, especially the NIPAM component.

Description

Methods to improve the blending of amphiphilic copolymers such as TRIS-NIPAM into silicone gel adhesive This application incorporates by reference published application
WO2011/005839.
The blending of TRIS-NIPAM copolymer into a silicone gel adhesive could be difficult depending on the amount of NIPAM co-monomer present in the copolymer. This is due to the chemical incompatibility between NIPAM segment of the copolymer and silicone gel. To facilitate blending of the copolymer into silicone gel prior to cure, and to obtain a useful gel with suitable properties after cure, it is necessary to incorporate additives during the blending process that are compatible with silicone and the copolymer, especially the NIPAM component. Further, the additive should not interfere with the catalyst, used in the gel cure.
The copolymer compatibility in the silicone gel prior to cure can be improved by one or more of the following methods: Copolymer Molecular weight and its composition:
The molecular weight and its distribution can have a significant impact on compatibility with silicone gel. Lower molecular weights of the copolymer with broader distribution are preferred. In addition, increasing the TRIS component should improve the compatibility.
Solvents:
Solvents with solubility parameter similar to the copolymer and the silicone are preferred. The preferred solvent solubility parameter range is 7-10. Examples of suitable solvents are ethyl acetate, hexamethydisiloxane, acetone, toluene, and tetrahydrofuran. The copolymer is initially dissolved in the solvent(s) and mixed thoroughly. The polymer solution is then added to the uncured gel with Part A and Part B, which are separately mixed together thoroughly before adding the polymer solution.
Compatibilizers:
Based on siloxanes:
Low molecular weight fluid phenyl-containing polysiloxanes; low molecular weight fluid polysiloxanes and cyclic siloxanes. Based on copolymers:
The copolymers could be diblocks, triblocks, random blocks, star shaped, or combed, or a combination. Examples of such copolymers are poly(TRIS-b- NIPAM), and poly(dimethylsiloxane-b-1-ethoxyethyl methacrylate) (from Polymer Source Inc.). Preferably, the copolymer is a solid.
Surfactants:
Silicone or non-silicone based surfactants.
Mixing conditions:
The temperature and shear rate during mixing of the copolymer into the gel is critical. A lower mixing temperature can favor the stability of the gel but can affect the solubility of the copolymer in the selected solvent or gel. Higher shear rates can improve the mixing process. Also, adding the copolymer slowly into the gel is preferred.

Claims

We Claim:
1. A method for making a silicone pressure sensitive adhesive to be used on human skin, comprising the steps of: a) dissolving an amphiphilic copolymer having at least one
comonomer that is nitrogen based into a solvent forming a solution; b) adding the solution to the silicone gel; and c) curing the silicone gel/solution to form a pressure sensitive adhesive.
2. A method for making a silicone pressure sensitive adhesive to be used on human skin, comprising the steps of: a) adding an amphiphilic copolymer having at least one comonomer that is nitrogen based into a silicone gel to form a mixture: and b) curing the mixture to form a pressure sensitive adhesive.
3. A method for making a silicone pressure sensitive adhesive to be used on human skin, comprising the steps of: a) dissolving an amphiphilic copolymer having at least one
comonomer that is nitrogen based into a solvent forming a solution; b) adding the solution to the silicone gel; c) adding at least one compatibilizer to the solution or the silicone gel; d) adding the solution comprising the compatibilizer to the silicone gel; e) curing the silicone gel/solution to form a pressure sensitive adhesive.
4. The method for making a silicone pressure sensitive adhesive to be used on human skin, according to claim 3, wherein the compatibilizer is a copolymer of silicone.
PCT/US2012/022498 2011-01-25 2012-01-25 Methods to improve the blending of amphiphilic copolymers such as tris-nipam into silicone gel adhesive WO2012103181A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161435908P 2011-01-25 2011-01-25
US61/435,908 2011-01-25

Publications (1)

Publication Number Publication Date
WO2012103181A1 true WO2012103181A1 (en) 2012-08-02

Family

ID=46581146

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2012/022498 WO2012103181A1 (en) 2011-01-25 2012-01-25 Methods to improve the blending of amphiphilic copolymers such as tris-nipam into silicone gel adhesive

Country Status (1)

Country Link
WO (1) WO2012103181A1 (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20010029143A1 (en) * 1996-12-31 2001-10-11 Mumick Pavneet Singh Temperature sensitive polymers and water-dispersible products containing the polymers
US7138458B2 (en) * 2001-05-01 2006-11-21 Corium International, Inc. Method for preparing a two-phase water-absorbent bioadhesive composition
US20070129474A1 (en) * 2005-12-07 2007-06-07 Rochal Industries, Llp. Conformable bandage and coating material
US20080140192A1 (en) * 2006-11-29 2008-06-12 University Of Southern California Reversible thermoresponsive adhesives for implants
US20100261814A1 (en) * 2005-09-23 2010-10-14 University Of North Texas Synthesis of columnar hydrogel colloidal crystals in water-organic solvent mixture
WO2011005839A1 (en) * 2009-07-07 2011-01-13 Convatec Technologies Inc. Pressure sensitive silicone adhesives with amphiphilic copolymers

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20010029143A1 (en) * 1996-12-31 2001-10-11 Mumick Pavneet Singh Temperature sensitive polymers and water-dispersible products containing the polymers
US7138458B2 (en) * 2001-05-01 2006-11-21 Corium International, Inc. Method for preparing a two-phase water-absorbent bioadhesive composition
US20100261814A1 (en) * 2005-09-23 2010-10-14 University Of North Texas Synthesis of columnar hydrogel colloidal crystals in water-organic solvent mixture
US20070129474A1 (en) * 2005-12-07 2007-06-07 Rochal Industries, Llp. Conformable bandage and coating material
US20080140192A1 (en) * 2006-11-29 2008-06-12 University Of Southern California Reversible thermoresponsive adhesives for implants
WO2011005839A1 (en) * 2009-07-07 2011-01-13 Convatec Technologies Inc. Pressure sensitive silicone adhesives with amphiphilic copolymers

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