WO2009063025A2 - Implant comportant un élastomère thermoplastique - Google Patents

Implant comportant un élastomère thermoplastique Download PDF

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Publication number
WO2009063025A2
WO2009063025A2 PCT/EP2008/065507 EP2008065507W WO2009063025A2 WO 2009063025 A2 WO2009063025 A2 WO 2009063025A2 EP 2008065507 W EP2008065507 W EP 2008065507W WO 2009063025 A2 WO2009063025 A2 WO 2009063025A2
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WIPO (PCT)
Prior art keywords
block
small joint
hard
soft
polyester
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PCT/EP2008/065507
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English (en)
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WO2009063025A3 (fr
Inventor
Darren Donald Obrigkeit
Atze Jan Nijenhuis
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Dsm Ip Assets Bv
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Publication of WO2009063025A2 publication Critical patent/WO2009063025A2/fr
Publication of WO2009063025A3 publication Critical patent/WO2009063025A3/fr

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    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04—Macromolecular materials
    • A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L2430/00—Materials or treatment for tissue regeneration
    • A61L2430/24—Materials or treatment for tissue regeneration for joint reconstruction

Definitions

  • the invention relates to a small joint implant.
  • the invention further relates to the use of a thermoplastic elastomer (TPE) in a small joint implant and in procedures for small joint arthrodesis, arthroplasty and bone replacement.
  • TPE thermoplastic elastomer
  • proximal phalangeal bone or proximal phalanx in the case of the metacarpophalangeal (MCP) or metatarsophalangeal (MTP) joint
  • Known treatments for arthritis include debridement of the articulating surfaces, excision or fusion of the affected joint or replacement of the joint with a prosthesis or arthroplasty.
  • one-piece joint replacements have received wide medical acclaim and improved markedly the prognosis for restriction patients.
  • one-piece designs for example those listed in Table 1 , ease surgical implantation and produce a more stable implant with less joint dislocation.
  • Such one-piece joint replacements can for example be made of silicone rubbers, optionally with other materials.
  • O ⁇ o currently used arthroplasty implant known as the Swanson prosthesis, has a central generally U-shaped hinge element and a pair of oppositely projecting intramedullary stems which are in use seated in holes drilled for tht? purpose in the ends of the bones which meet at the joint Tho device is made of a flexiblo silicone
  • silicone rubbers are associated with several other complications.
  • high performance silicone rubber is used in space-filler type joints in artificial joint replacement.
  • arthroplasty devices consist of two components with cooperating convex and concave surfaces which articulate against one another in the joint. Examples are listed in Table 2.
  • the components are attached to their respective bones by rigid intramedullary stems which seat in holes formed in the ends of the bones.
  • a single component is fixed to one bone end to articulate against a shaped end of the other bone.
  • Other articulating designs replace only one half of the joint; these also fail to provide the stability of a one-piece implant.
  • other non-elastomeric engineering plastics such as PEEK can be used.
  • MCP metacarpophalangeal implant
  • PIP proximal
  • DIP distal
  • MTP metatarsalphalangeal implant
  • the aim of the invention is therefore to provide an implant for a small joint that does not show the aforementioned disadvantages, or at least shows them to a lesser extent.
  • thermoplastic elastomer comprising a hard phase and soft phase.
  • the small joint implant according to the invention has particular superior flex fatigue performance and crack growth resistance, high wear resistance, low creep, low compression set, high dimensional stability and high resistance to moisture, such that a compliant durable implant can be made.
  • Such implant may comprise only one part without the need to articulate to preserve motion, such that wear due to articulation is avoided.
  • the implant may consist of two or more parts of which at least one part comprises the TPE according to the invention.
  • the TPE can be combined with other elastomeric materials of different stiffness and flexibility and/or hard materials, such as metals and higher modulus polymers.
  • TPE has a crystalline (hard phase) component which is very resilient to mechanical forces, it can easily be processed to provide a variety of designs, by for example injection molding and that the shape of the implant according to the invention can easily be adapted during surgery to adapt it to the patient's anatomy.
  • the small joint implant according to the invention comprises a thermoplastic elastomer (TPE) comprising a hard phase and a soft phase.
  • TPE thermoplastic elastomer
  • the hard phase in the TPE comprises a rigid polymer phase with a melting temperature (Tm) or a glass transition temperature (Tg) higher than 35 0 C.
  • the soft phase in the TPE comprises a flexible, amorphous polymer phase with a Tg lower than 35 0 C, preferably lower than 0 0 C.
  • the TPE used according to the invention, comprises, for example, blends of hard phase polymers with soft phase polymers and block copolymers.
  • the hard and the soft phase can comprise one polymer type, but can also be composed of a mixture of two or more polymeric materials.
  • TPE's examples include styrenic TPE's, polyolefin-based TPE's including polyolefin blends, elastomeric alloys, thermoplastic polyurethanes, thermoplastic copolyesters and thermoplastic polyamides, TPE's based on halogen-containing polyolefins, polyether- ester elastomers, ionomeric TPE's and polyacrylate-based TPE's.
  • the TPE used according to the invention, comprises a hard phase comprising a polymer chosen from the group consisting of polyester, polyamide, polystyrene, polyacrylate and polyolefin and a soft phase comprising a - A -
  • polymer chosen from the group consisting of polyether, polyester, polyacrylate, polyolefin and polysiloxane.
  • the TPE used according to the invention, is a block- copolymer.
  • the TPE used in the small joint implant comprises a thermoplastic elastomer comprising hard blocks and soft blocks, wherein the hard blocks comprise a polymer chosen from the group consisting of polyester, polyamide, polystyrene, polyacrylate and polyolefin and the soft blocks comprise a polymer chosen from the group consisting of polyether, polyester, polyacrylate, polyolefin and polysiloxane.
  • TPE block-copolymers are block-copolyesterester, block-copolyetherester, block-copolycarbonateester, block-copolysiloxaneester, block-copolyesteramide, block-copolymer containing polybutylene terephthalate (PBT) hard blocks and poly(oxytetramethylene) soft blocks, block-copolymer containing polystyrene hard blocks and ethylene butadiene soft blocks (SEBS).
  • PBT polybutylene terephthalate
  • SEBS ethylene butadiene soft blocks
  • the hard blocks in the thermoplastic elastomer consist of a rigid polymer, as described above, with a Tm or Tg higher than 35 0 C.
  • the different polymers as described above can be used as the hard blocks.
  • a polycarbonate is understood to be a polyester.
  • copolymers of esters, amides, styrenes, acrylates and olefins can be used as the hard polymer block as long as the Tm or Tg of the hard polymer block is higher than 35 0 C.
  • the hard block of the TPE is a polyester block.
  • the hard block consists of repeating units derived from at least one alkylene glycol and at least one aromatic dicarboxylic acid or an ester thereof.
  • the alkylene group generally contains 2-6 carbon atoms, preferably 2-4 carbon atoms.
  • Preferable for use as the alkylene glycol are ethylene glycol, propylene glycol and in particular butylene glycol.
  • Terephthalic acid, 2,6-naphthalenedicarboxylic acid and 4,4'-diphenyldicarboxylic acid are very suitable for use as the aromatic dicarboxylic acid. Combinations of these dicarboxylic acids, and/or other dicarboxylic acids such as isophthalic acid may also be used. Their effect is to influence the crystallization behaviour, e.g. melting point, of the hard polyester blocks.
  • the hard block is polybutyleneterephthalate.
  • the soft blocks in the thermoplastic elastomer consist of a flexible polymer, as described above, with a Tg lower than 35 0 C. In principle the polymers as described above can be used as the soft blocks.
  • a polycarbonate is understood to be a polyester.
  • copolymers of ethers, esters, acrylates, olefins and siloxanes can be used as the soft polymer block as long as the Tg of the soft polymer block is lower than 35 0 C.
  • the soft block comprises a polyester or a polyether; more preferably an aliphatic polyester or polyether.
  • TPE's comprising polyester, or polyether soft blocks is that aliphatic polyesters, and polyethers feature a high chemical stability.
  • alkylene carbonates and aliphatic polyesthers are preferred as the soft block, which result in thermoplastic elastomers with particularly low moisture sensitivity and favourable adhesive properties.
  • the soft blocks in the TPE are derived from at least one alkylene carbonate and optionally, a polyester made up of repeating units derived from an aliphatic diol and an aliphatic dicarboxylic acid.
  • the alkylene carbonate can be represented by the formula
  • the aliphatic diol units are preferably derived from an alkylenediol containing 2 - 20 C atoms, preferably 3 - 15 C atoms, in the chain and an alkylenedicarboxylic acid containing 2 - 20 C atoms, preferably 4 - 15 C atoms. More preferably, the soft block comprises a polycarbonate.
  • thermoplastic block-copolyesters as defined in ISO 18064: 2003
  • TPC-ET thermoplastic block-copolyesters
  • the TPE comprises a hard block comprising polybutyleneterephthalate and a soft block comprising polycarbonate.
  • this TPE is chain-extended with diisocyanate.
  • block-copolyether esters are for example described in the Handbook of Thermoplastics, ed. O.OIabishi, Chapter 17, Marcel Dekker Inc., New York 1997, ISBN 0-8247-9797-3, Thermoplastic Elastomers, 2nd Ed., Chapter 8, Carl Hanser Verlag (1996), ISBN 1-56990-205-4, and the Encyclopedia of Polymer Science and Engineering, Vol. 12, pp.75-1 17, and the references contained therein.
  • the ratio of the soft and hard blocks in the TPE used in the small joint implant according to the invention may generally vary within a wide range but is in particular chosen in view of the desired modulus of the TPE.
  • the desired modulus will depend on the structure and size (e.g. thickness) of the small joint implant and the functionality of the TPE in it. Generally, a higher soft block content results in higher flexibility and better toughness.
  • the TPE according to the invention may contain one or more additives such as stabilizers, anti-oxidants, colorants, fillers, binders, fibers, meshes, substances providing radiopacity, surface active agents, foaming agents, processing aids, plasticizers, biostatic/biocidal agents, and any other known agents which are described in Rubber World Magazine Blue Book, and in Gaether et al., Plastics Additives Handbook, (Hanser 1990).
  • Suitable examples of fillers, e.g. radiopaque fillers and bone-mineral based fillers, and binders are described in U.S. Patent Number 6,808,585B2 in columns 8-10 and in U.S. Patent Number 7, 044,972B2 in column 4, I. 30-43, which are herein incorporated by reference.
  • Suitable commercially available TPE's include Arnitel ® TPE (DSM Engineering Plastics), in particular Arnitel ® E (polyether ester, PTMEG), Arnitel ® C (polycarbonate-ester, PHMC) and Arnitel ® P (polyether ester, polyols, polypropylene and polyethylene).
  • Arnitel ® grades include 55D, EL250, EM400, EM450, EM550, EM630, EL740, PL380, PL381 , PM381 , PL580, PM581 , 3103, 3104, and 3107.
  • thermoplastic block polyesters have been the subject of numerous FDA regulatory approvals. Specifically, Arnitel ® copolyesters have been listed under the Drug Master Files 13260, 13261 , 13263, 13264, 13259, and 13262. Additionally, these compositions have been cleared for use in permanent implants (510(k) K990952, K896946). According to the FDA MAUDE database, adverse events dating back to prior April, 2000 are mild and due to mechanical failure (see catalog number 8886441433, 447071 , 8886471011 V, and 8886470401 ). The absence of adverse effects due to material confirms the long-term biocompatibility of these compositions.
  • Arnitel ® E grades are in compliance with the code of Federal regulation, issued by the Food and Drug Administration (FDA) 21 CFR 177.2600 (rubber articles for repeated use) in the USA, the so-called FDA approval. Moreover, US Pharmacopoeia approvals were received for the following Arnitel ® grades: EM400, EM450, EM550, EM740, PL580 and 3104 (USP Class Vl), and PL380 and PM381 (USP Class IV).
  • FDA Food and Drug Administration
  • multiblock poly(aliphatic/aromatic ester) (PED) copolymers as described in M. El Fray and V. Altstadt, Polymer, 44 (2003) pp. 4643-4650 can suitably be used as the TPE according to the invention.
  • the small joint implant according to the invention can be produced in many different ways. Known techniques include (co-)injection molding, (co-)extrusion molding, blow molding or injection overmolding.
  • the temperature and other processing conditions at which the TPE can best be processed depends on the melting temperature, the viscosity and other rheological properties of the TPE and can easily be determined by the person skilled in the art once said properties are known.
  • the above mentioned Arnitel ® grades have melting temperatures (measured according to ISO 11357-1/-3) between 180 and 221 0 C and are preferably processed at temperatures between 200 and 250 0 C.
  • TPE's according to the invention in particular Arnitel ® TPE's, can be sterilized by any known means.
  • the TPE's according to the invention can be cut with a fluid jet for customizing the implant shape to the patient's anatomy.
  • a fluid jet for customizing the implant shape to the patient's anatomy.
  • Such fluid jets are described in patent US6960182 and are commercially provided by Hydrocision, Inc. (Billerica, MA).
  • the ability to customize an implant with a fluid jet represents a significant advance over the current standard of practice, where grinding tools (e.g. Dremel) are used to abrade the surfaces of implants, which result in damaged implant surfaces, possible introduction of wear particles in the operating room, etc. This is particularly relevant for small joints.
  • the FDA database often cites wrong finger size as a reason for revision surgery (FDA MAUDE database).
  • implants are subjected to repeated cycles and rotations.
  • hard-soft block systems are unique because they have a crystalline (hard block) component which is very resilient to mechanical forces. Moreover they are easily processible to provide a variety of designs and possess exceptional flex fatigue, which can be measured according to e.g. ISO 132 in which Arnitel ® TPE has been demonstrated to survive an excess of 15 million cycles.
  • TPE's offer the unique advantage of improved wear and fatigue resistance over traditional materials (e.g. silicone). This allows the creation of an implant with both 1.) the superior stability of a one-piece implant and 2.) the superior durability of a two-piece performance. Therefore, the use of TPE is especially advantageous in one-piece prostheses requiring good flex fatigue resistance such as MCP, PIP, DIP, MTP, Great Toe, etc (Tables 1 and 2). For these implants, improved flex fatigue resistance especially reduces the incidence of implant fracture at the hinge (for example when used in implant parts as disclosed in US387559, Fig. 2, 12; GB1192960, Fig. 1 , 12; US4871367, Fig. 2, 14; Fig 3. 34; US5824095, Fig.
  • a particular advantage of the use of a TPE according to the invention is its very good adhesion to different materials, for example to a different TPE, e.g. a TPE with a different stiffness or modulus, or a metal.
  • a different TPE e.g. a TPE with a different stiffness or modulus
  • a metal for example Ti 6 AI 4 V
  • This property is expressed as a high peel strength.
  • the peel strength is higher than 6 N/cm, measured according to ISO/IEC standard 7810. This is particularly advantageous for implants which employ grommets as described, for example, in US6319284B1 Fig. 4, 84, 86.
  • TPE's provides the ability to meet requirements without articulating surfaces, which minimizes the occurrence of wear, particles and/or reactions.
  • Examples of known small joint implant designs that can be made partially or completely from the TPE according to the invention, or that can be partially or completely overmolded with the TPE according to the invention are a metacarpophalangeal implant, a proximal or distal interphalangeal implant, a trapezium/metacarpal spacer implant and a metatarsalphalangeal implant.
  • a metacarpophalangeal implant a proximal or distal interphalangeal implant
  • a trapezium/metacarpal spacer implant and a metatarsalphalangeal implant.
  • the known one-piece small joint implants according to Table 1 can be entirely made of TPE.
  • the two-component small joint implants according to Table 2 can be entirely or partly made of the TPE according to the invention, for example by using different grades of TPE with different properties, or by combining TPE with other materials, for example metals, PEEK or pyrolitic carbon.
  • Arnitel ® 55D hard block: polybutylene terepthalate (PBT), soft-block: polycarbonate, modulus 140 MPa
  • Arnitel ® EL250 hard block polybutylene terepthalate (PBT), soft-block: polytetramethyleneoxide (PTMO), modulus 25 MPa) from DSM N.V.
  • Arnitel ® EM400 hard block: polybutylene terepthalate (PBT), soft-block: polytetramethyleneoxide (PTMO), modulus 50 MPa) from DSM N.V.
  • Arnitel ® EM460 hard block polybutylene terepthalate (PBT), soft-block: polytetramethyleneoxide (PTMO), modulus 100 MPa) from DSM N.V.
  • Arnitel ® EM550 hard block polybutylene terepthalate (PBT), soft-block: polytetramethyleneoxide (PTMO), modulus 200 MPa) from DSM N.V.
  • Arnitel ® EM630 and 630-H hard block polybutylene terepthalate (PBT), soft-block: polytetramethyleneoxide (PTMO), modulus 310 MPa) from DSM
  • Arnitel ® EM740 hard block polybutylene terepthalate (PBT), soft-block: polytetramethyleneoxide (PTMO), modulus 1 100 MPa) from DSM N.V.
  • Arnitel ® PL380 hard block polybutylene terepthalate (PBT), soft block:
  • the crack-growth resistance was measured according to ASTM D 1052 on a Ross tester, measuring the resistance of a material against crack growth under cyclic loading.
  • a through thickness crack (2.5 mm width) was made in a sample with dimensions 25.4 x 6.4 x 152.4 mm 3 .
  • the sample was flexed between 0° and 90° and the growth of the crack was monitored as a function of the number of cycles.
  • Silastic Q7-4565 shows 500 % increase in crack length after 250,000 cycles (D. T. Hutchinson et al., J. Biomed. Mat. Res., vol 37, no. 1 , pp 94-99 (1998)).
  • Silastic HP100 shows 500 % increase in crack length after 390,000 cycles, and complete failure of the sample after 950,000 cycles (K.M. Savory et al., J. Biomed. Mat. Res., vol 28, No. 10, pp 1209-1219 (1994)).
  • thermoplastic polyether ester elastomer block copolymers which are examples of the TPE according to the invention, perform significantly better on crack-growth resistance than the silicone rubbers tested.
  • GLP conditions according to ISO 10993 parts 3, 5, 6, 7, 10, and 11 : ISO10993-3 Tests for genotoxicity, carcinogenicity, and reproductive toxicity.
  • EM400, EM460, EL630, and EL740 were tested for the effects of gamma sterilization up to 100 KGray (roughly 4 times a typical sterilization dose). These samples were subsequently mechanically tested to determine the effects on E-modulus, Stress at Break, and Strain at Break. In all instances little or no changes in the material properties were observed.
  • Arnitel ® EM400 and Elastollan ® 1190A TPU were tested according to the ISO 132 deMattia test. The results showed comparable crack growth numbers for Arnitel ® EM400 and Elastollan ® 1 190A.
  • Example V Comparison of tensile and creep properties
  • the tensile modulus and the creep properties were determined at room temperature according to ISO 527.
  • the sample used was type 5A.
  • the determined tensile modulus of three materials was similar.
  • Cylindrical samples having a 13 mm diameter and 6 mm height were mounted between the plates of a MTS 810-11 servo-hydraulic tensile tester.
  • the samples were loaded force controlled by a harmonically time varying compressive force.
  • the cycle frequency of the force signal was 0.25 Hz.
  • the maximum compressive stress during a cycle was 4 MPa whereas the minimum compressive stress was 0.4 MPa.
  • the experiments were carried out in an oven at 37°C.
  • the stress levels that were applied were derived from ASTM 2423-05, and were chosen to be higher by a factor 4.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Materials For Medical Uses (AREA)
  • Prostheses (AREA)

Abstract

L'invention concerne une petite prothèse d'articulation incluant un élastomère thermoplastique qui comporte une phase dure et une phase molle. De préférence, l'élastomère comporte une phase dure contenant un polymère choisi dans le groupe constitué par un polyester, un polyamide, un polystyrène, un polyacrylate et une polyoléfine, et une phase molle contenant un polymère choisi dans le groupe constitué par un polyéther, un polyester, un polyacrylate, une polyoléfine et un polysiloxane.
PCT/EP2008/065507 2007-11-13 2008-11-13 Implant comportant un élastomère thermoplastique WO2009063025A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US99634607P 2007-11-13 2007-11-13
US60/996,346 2007-11-13
EP08151528.0 2008-02-15
EP08151528 2008-02-15

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WO2009063025A2 true WO2009063025A2 (fr) 2009-05-22
WO2009063025A3 WO2009063025A3 (fr) 2010-05-06

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10640614B2 (en) 2016-07-28 2020-05-05 3M Innovative Properties Company Segmented silicone polyamide block copolymers and articles containing the same
US10865330B2 (en) 2016-07-28 2020-12-15 3M Innovative Properties Company Segmented silicone polyamide block copolymers and articles containing the same

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EP0891783A1 (fr) * 1997-07-16 1999-01-20 Isotis B.V. Dispositif pour la régénération osseuse consistant d'un copolyester thermoplastique biodégradable et de cellules cultivées
EP1027897A1 (fr) * 1999-02-10 2000-08-16 Isotis B.V. Systèmes de régénération du tissus de cartilage
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US20070014848A1 (en) * 2005-07-15 2007-01-18 Boehringer Ingelheim Pharma Gmbh & Co. Kg Resorbable Polyetheresters and Medicinal Implants Made Therefrom

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PROWANS P ET AL: "Biocompatibility studies of new multiblock poly(ester-ester)s composed of poly(butylene terephthalate) and dimerized fatty acid" BIOMATERIALS, ELSEVIER SCIENCE PUBLISHERS BV., BARKING, GB, vol. 23, no. 14, 1 July 2002 (2002-07-01), pages 2973-2978, XP004353896 ISSN: 0142-9612 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10640614B2 (en) 2016-07-28 2020-05-05 3M Innovative Properties Company Segmented silicone polyamide block copolymers and articles containing the same
US10865330B2 (en) 2016-07-28 2020-12-15 3M Innovative Properties Company Segmented silicone polyamide block copolymers and articles containing the same

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