WO2016105998A1 - Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer - Google Patents

Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer Download PDF

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Publication number
WO2016105998A1
WO2016105998A1 PCT/US2015/065557 US2015065557W WO2016105998A1 WO 2016105998 A1 WO2016105998 A1 WO 2016105998A1 US 2015065557 W US2015065557 W US 2015065557W WO 2016105998 A1 WO2016105998 A1 WO 2016105998A1
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WO
WIPO (PCT)
Prior art keywords
composition
polymer
film
polyvinyl acetate
plasticizer
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US2015/065557
Other languages
English (en)
French (fr)
Inventor
Ning Zhou
Robert S. Clough
Derek J. Dehn
Jeffrey P. KALISH
William W. Merrill
Kevin M. Lewandowski
Jayant Chakravarty
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties Co
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 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Priority to EP24174876.3A priority Critical patent/EP4389843A3/en
Priority to KR1020177019948A priority patent/KR102465303B1/ko
Priority to JP2017533272A priority patent/JP6787897B2/ja
Priority to US15/528,791 priority patent/US10577494B2/en
Priority to CN201580070021.3A priority patent/CN107109041B/zh
Priority to EP15828578.3A priority patent/EP3237541B1/en
Publication of WO2016105998A1 publication Critical patent/WO2016105998A1/en
Priority to JP2018549760A priority patent/JP6983170B2/ja
Priority to EP16876383.7A priority patent/EP3390563B1/en
Priority to US15/768,957 priority patent/US20190218423A1/en
Priority to CN201680073200.7A priority patent/CN108473837B/zh
Priority to PCT/US2016/064897 priority patent/WO2017105887A1/en
Anticipated expiration legal-status Critical
Priority to US16/748,040 priority patent/US11254812B2/en
Priority to US17/570,862 priority patent/US11787929B2/en
Ceased legal-status Critical Current

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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08L31/04—Homopolymers or copolymers of vinyl acetate
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    • 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
    • C09J2431/00—Presence of polyvinyl acetate
    • C09J2431/006—Presence of polyvinyl acetate in the substrate
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer
    • 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
    • C09J2467/00—Presence of polyester
    • 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
    • C09J2467/00—Presence of polyester
    • C09J2467/006—Presence of polyester in the substrate
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31909—Next to second addition polymer from unsaturated monomers
    • Y10T428/31928—Ester, halide or nitrile of addition polymer

Definitions

  • composition comprising semicrystalline polylactic acid polymer; polyvinyl acetate polymer having a glass transition temperature (Tg) of at least 25°C; plasticizer; and optionally amorphous polylactic acid polymer.
  • Tg glass transition temperature
  • a film comprising such composition(s).
  • the film preferably has a net melting endotherm for the first heating scan, AHnmi, greater than 10, 11, 12, 13, 14, or 15 and less than 40 J/g. Further, the film preferably has a Tg less than 30°C, 25°C or 20°C.
  • FIG. 4 depicts Dynamic Mechanical Analysis results of Example 16.
  • the PLA polymers are preferably "film grade" polymers, having a melt flow rate (as measured according to ASTM D1238) of no greater than 25, 20, 15, or 10 g/min at 210°C with a mass of 2.16 kg. In some embodiments, the PLA polymer has a melt flow rate of less than 10 or 9 g/min at 210°C. The melt flow rate is related to the molecular weight of the PLA polymer.
  • the PLA polymer typically has a weight average molecular weight (Mw) as determined by Gel Permeation Chromatography with polystyrene standards of at least 50,000 g/mol; 75,000 g/mol; 100,000 g/mol; 125,000 g/mol; 150,000 g/mol. In some embodiments, the molecular weight (Mw) is no greater than 400,000 g/mol; 350,000 g/mol or 300,000 g/mol.
  • comonomers provided that the Tg of the polyvinyl acetate polymer is within the ranges previously described.
  • Other comonomers include for example acrylic monomers such as acrylic acid and methyl acrylate; vinyl monomers such as vinyl chloride and vinyl pyrollidone; and C2-C8 alkylene monomers, such as ethylene.
  • the total concentration of repeats derived from other comonomers of the polyvinyl acetate polymer is typically no greater than 10, 9, 8, 7, 6, or 5 wt.-%. In some embodiments, the concentration of repeats derived from other comonomers of the polyvinyl acetate polymer is typically no greater than 4, 3, 2, 1 or 0.5 wt.-%.
  • composition and film may optionally contain one or more conventional additives.
  • Additives include, for example, antioxidants, stabilizers, ultraviolet absorbers, lubricants, processing aids, antistatic agents, colorants, impact resistance aids, fillers, matting agents, flame retardants (e.g. zinc borate), pigments, and the like.
  • the multilayer film typically has the thickness just described.
  • the thickness of the film layer may be less than 10 microns.
  • the film layer comprising the composition described herein is an exterior layer or in other words a skin layer.
  • a second film layer is disposed upon the skin layer. The second film layer typically has a different composition than the skin layer.
  • the PLA, PVAc, plasticizer, nucleating agent, etc. are heated (e.g. 180 - 250 °C) and thoroughly mixed using any suitable means known by those of ordinary skill in the art.
  • the composition may be mixed by use of a (e.g., Brabender) mixer, extruder, kneader or the like.
  • PLA compositions and films described herein can be used in a variety of products.
  • the PLA film has similar or even better properties to polyvinyl chloride (PVC) film, and thus can be used in place of PVC films.
  • PVC polyvinyl chloride
  • the film and compositions can have various properties, as determined by the test methods set forth in the examples.
  • the film and composition generally has a glass transition temperature ranging from about -20°C, -15°C, or -10°C to 40°C; below the Tg of both the PLA polymer and the polyvinyl acetate polymer.
  • the film and composition has a glass transition temperature of at least -5, -4, -3, -2, -1 or 0°C.
  • the film and composition has a glass transition temperature of less than 35°C or 30°C or 25°C.
  • the film and composition has a glass transition temperature of less than 20°C, 19°C, or 18°C.
  • the film and composition typically has a melting temperature, Tmi or T m2 , ranging from of at least about 150°C or 155 °C to about 165°C or 170°C. Further, the composition can have a crystallization peak temperature Tc ranging from 100 °C to 120°C.
  • the acrylic pressure sensitive adhesive comprises polymerized units of one or more low Tg (meth)acrylate monomers, i.e. a (meth)acrylate monomer when reacted to form a homopolymer has a T g no greater than 0°C.
  • the low Tg monomer has a T g no greater than -5°C, or no greater than -10°C.
  • the Tg of these homopolymers is often greater than or equal to -80°C, greater than or equal to -70°C, greater than or equal to -60°C, or greater than or equal to -50°C.
  • a 0.5 inch (-1.3 cm) wide by 6 inch (-15 cm) long strip of adhesive was laminated onto a stainless steel panel using a roller. Dwell time was 10 minutes in the CTH (constant temperature and humidity) room conditioned at 23°C/50% RH. Peel strength

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Manufacturing & Machinery (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Biological Depolymerization Polymers (AREA)
  • Adhesive Tapes (AREA)
  • Laminated Bodies (AREA)
  • Adhesives Or Adhesive Processes (AREA)
PCT/US2015/065557 2014-12-22 2015-12-14 Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer Ceased WO2016105998A1 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
EP24174876.3A EP4389843A3 (en) 2014-12-22 2015-12-14 Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer
KR1020177019948A KR102465303B1 (ko) 2014-12-22 2015-12-14 폴리락트산 중합체, 폴리비닐 아세테이트 중합체 및 가소제를 포함하는 조성물 및 필름
JP2017533272A JP6787897B2 (ja) 2014-12-22 2015-12-14 ポリ乳酸ポリマーとポリ酢酸ビニルポリマーと可塑剤とを含む組成物及びフィルム
US15/528,791 US10577494B2 (en) 2014-12-22 2015-12-14 Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer
CN201580070021.3A CN107109041B (zh) 2014-12-22 2015-12-14 包含聚乳酸聚合物、聚乙酸乙烯酯聚合物和增塑剂的组合物和膜
EP15828578.3A EP3237541B1 (en) 2014-12-22 2015-12-14 Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer
PCT/US2016/064897 WO2017105887A1 (en) 2015-12-14 2016-12-05 Polylactic acid polymer based film comprising an adhesive layer
JP2018549760A JP6983170B2 (ja) 2015-12-14 2016-12-05 接着剤層を備えたポリ乳酸ポリマー系フィルム
EP16876383.7A EP3390563B1 (en) 2015-12-14 2016-12-05 Polylactic acid polymer based film comprising an adhesive layer
US15/768,957 US20190218423A1 (en) 2015-12-14 2016-12-05 Polylactic acid polymer based film comprising an adhesive layer
CN201680073200.7A CN108473837B (zh) 2015-12-14 2016-12-05 包括粘合剂层的基于聚乳酸聚合物的膜
US16/748,040 US11254812B2 (en) 2014-12-22 2020-01-21 Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer
US17/570,862 US11787929B2 (en) 2014-12-22 2022-01-07 Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer

Applications Claiming Priority (2)

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US201462095285P 2014-12-22 2014-12-22
US62/095,285 2014-12-22

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US16/748,040 Continuation US11254812B2 (en) 2014-12-22 2020-01-21 Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer

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EP (2) EP3237541B1 (OSRAM)
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CN (1) CN107109041B (OSRAM)
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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018106486A1 (en) 2016-12-05 2018-06-14 3M Innovative Properties Company Composition and films comprising polylactic acid polymer and copolymer comprising long chain alkyl moiety
KR101875130B1 (ko) * 2017-05-31 2018-08-02 한국과학기술연구원 물성이 개선된 pla 조성물
US10434493B2 (en) 2015-12-18 2019-10-08 3M Innovative Properties Company Metal-containing sorbents for nitrogen-containing compounds
US10597564B2 (en) 2015-12-22 2020-03-24 3M Innovative Properties Company Internally incorporated phenolic resins in water-based (meth)acrylate adhesive compositions, pre-adhesive reaction mixtures, methods, and articles
US10759980B1 (en) 2015-12-22 2020-09-01 3M Innovative Properties Company Packaged pre-adhesive composition including a polylactic acid-containing packaging material, adhesives, and articles
US10982090B2 (en) 2016-06-21 2021-04-20 3M Innovative Properties Company Graphic articles comprising polylactic acid polymer based film
US11066551B2 (en) 2016-05-20 2021-07-20 3M Innovative Properties Company Oriented polylactic acid polymer based film
US11286405B2 (en) 2016-12-05 2022-03-29 3M Innovative Properties Company Adhesive articles comprising polylactic acid polymer film and method of making
US11407872B2 (en) 2016-06-21 2022-08-09 3M Innovative Properties Company Foam compositions comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer, articles, and methods of making and using same
US11766822B2 (en) 2019-08-20 2023-09-26 3M Innovative Properties Company Microstructured surface with increased microorganism removal when cleaned, articles and methods
US11981810B2 (en) 2019-03-29 2024-05-14 3M Innovative Properties Company Film comprising polylactic acid polymer suitable for graphic articles
US12434427B2 (en) 2019-08-20 2025-10-07 Solventum Intellectual Properties Company Microstructured surface with increased microorganism removal when cleaned, articles and methods
WO2025238446A1 (en) 2024-05-17 2025-11-20 3M Innovative Properties Company Coating comprising methyl methacrylate copolymer with silicon-oxygen groups and articles

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3237541B1 (en) * 2014-12-22 2024-07-10 3M Innovative Properties Company Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer
JP6983170B2 (ja) * 2015-12-14 2021-12-17 スリーエム イノベイティブ プロパティズ カンパニー 接着剤層を備えたポリ乳酸ポリマー系フィルム
US10662273B2 (en) * 2016-12-19 2020-05-26 Celanese International Corporation Waterborne acrylic dispersions with high biorenewable content
EP3728430A1 (en) 2017-12-20 2020-10-28 3M Innovative Properties Company Composite particles, compositions and foam compositions containing composite particles, articles, and methods of making and using same
KR101854321B1 (ko) * 2018-01-04 2018-05-03 박철원 피니싱 호일 접착용 친환경 접착제 조성물, 그리고 이의 제조 방법
WO2020053826A1 (en) 2018-09-13 2020-03-19 3M Innovative Properties Company Foam compositions and methods of making same
CN111718567A (zh) * 2019-03-22 2020-09-29 汉达精密电子(昆山)有限公司 一种透明生物降解复合材料及其制品
US11767406B2 (en) 2019-06-18 2023-09-26 3M Innovative Properties Company Compositions and foam compositions containing composite particles, articles, composite particles, and methods
JP2023539733A (ja) * 2020-08-21 2023-09-19 スリーエム イノベイティブ プロパティズ カンパニー 溶媒バリア及びプライマー層を含むフィルム
JP2024507741A (ja) * 2021-02-09 2024-02-21 ニューライト テクノロジーズ インコーポレイテッド 高屈曲性ｐｈａシートの製造のための組成物および方法
KR20230146084A (ko) 2021-02-17 2023-10-18 와커 헤미 아게 첨가제 함유 바이오폴리머 조성물
CN113512181B (zh) * 2021-08-09 2022-08-12 重庆大学 一种可低温加工的聚乳酸及其制备方法
WO2024253647A1 (en) * 2023-06-07 2024-12-12 Sanson Gelmi Water-soluble and disposable glove

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0587069A1 (en) * 1992-09-04 1994-03-16 MITSUI TOATSU CHEMICALS, Inc. Degradable adhesive film and degradable resin composition
US6005068A (en) 1992-10-02 1999-12-21 Cargill Incorporated Melt-stable amorphous lactide polymer film and process for manufacture thereof

Family Cites Families (160)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3011988A (en) 1957-05-21 1961-12-05 Minnesota Mining & Mfg Acrylic tetrapolymer, aqueous dispersion thereof and article coated therewith
JP2561853B2 (ja) * 1988-01-28 1996-12-11 株式会社ジェイ・エム・エス 形状記憶性を有する成形体及びその使用方法
US5216050A (en) 1988-08-08 1993-06-01 Biopak Technology, Ltd. Blends of polyactic acid
WO1990001521A1 (en) 1988-08-08 1990-02-22 Battelle Memorial Institute Degradable thermoplastic from lactides
CA1339026C (en) * 1988-08-08 1997-03-25 Richard G. Sinclair Degradable thermoplastics from lactides
US5502158A (en) 1988-08-08 1996-03-26 Ecopol, Llc Degradable polymer composition
JP2694854B2 (ja) 1988-12-16 1997-12-24 光洋化学 株式会社 粘着テープ
US5032460A (en) 1989-08-14 1991-07-16 Minnesota Mining And Manufacturing Company Method of making vinyl-silicone copolymers using mercapto functional silicone chain-transfer agents and release coatings made therewith
EP0548284A1 (en) 1990-09-06 1993-06-30 Biopak Technology Ltd Packaging thermoplastics from lactic acid
JPH04242109A (ja) 1991-01-11 1992-08-28 Hitachi Metals Ltd 超音波による膜厚測定方法
US5296277A (en) 1992-06-26 1994-03-22 Minnesota Mining And Manufacturing Company Positionable and repositionable adhesive articles
JPH0623836A (ja) 1992-07-09 1994-02-01 Shimadzu Corp ポリ乳酸延伸フィルムの製造方法
US5698279A (en) 1992-09-23 1997-12-16 Viskase Corporation Heat shrinkable nylon food casing having a functionalized ethylenic polymer core layer
US5338822A (en) * 1992-10-02 1994-08-16 Cargill, Incorporated Melt-stable lactide polymer composition and process for manufacture thereof
US5677376A (en) 1994-01-14 1997-10-14 Minnesota Mining And Manufacturing Company Acrylate-containing polymer blends
US5763513A (en) 1994-05-19 1998-06-09 Mitsui Toatsu Chemicals, Inc. L-lactic acid polymer composition, molded product and film
US5804610A (en) 1994-09-09 1998-09-08 Minnesota Mining And Manufacturing Company Methods of making packaged viscoelastic compositions
CA2220409C (en) 1995-05-10 2002-07-16 Avery Dennison Corporation Pigmented, uv-cured, acrylic-based, pressure sensitive adhesives, and method for making same
US5623010A (en) 1995-06-22 1997-04-22 Minnesota Mining And Manufacturing Company Acrylate-containing polymer blends and methods of using
US5726220A (en) 1995-08-30 1998-03-10 Shin-Etsu Chemical Co., Ltd. Biodegradable polymer compositions and shrink films
JPH09151310A (ja) 1995-08-30 1997-06-10 Shin Etsu Chem Co Ltd 生分解性を有するポリマー組成物および収縮フィルム
JP3257391B2 (ja) 1996-03-18 2002-02-18 東洋インキ製造株式会社 インクジェット記録液
JP2000514129A (ja) 1996-10-08 2000-10-24 ミネソタ マイニング アンド マニュファクチャリング カンパニー 下塗り剤組成物および有機ポリマー基材の接着
US5981113A (en) 1996-12-17 1999-11-09 3M Innovative Properties Company Curable ink composition and imaged retroreflective article therefrom
US6197397B1 (en) 1996-12-31 2001-03-06 3M Innovative Properties Company Adhesives having a microreplicated topography and methods of making and using same
EP0966502A4 (en) 1997-03-14 2000-05-10 Univ Nebraska DEGRADABLE COMPOSITE POLYMER AND METHOD FOR THE PRODUCTION THEREOF
US5883199A (en) 1997-04-03 1999-03-16 University Of Massachusetts Polyactic acid-based blends
US6008286A (en) 1997-07-18 1999-12-28 3M Innovative Properties Company Primer composition and bonding of organic polymeric substrates
ATE266434T1 (de) * 1998-02-23 2004-05-15 Massachusetts Inst Technology Bioabbaubare polymere mit formgedächtnis
US6114495A (en) * 1998-04-01 2000-09-05 Cargill Incorporated Lactic acid residue containing polymer composition and product having improved stability, and method for preparation and use thereof
US6534172B1 (en) 1998-04-14 2003-03-18 Sony Chemicals Corp. Pressure-sensitive adhesive tape and process for producing the same
EP1008629A1 (en) * 1998-05-30 2000-06-14 DAICEL CHEMICAL INDUSTRIES, Ltd. Biodegradable polyester resin composition, biodisintegrable resin composition, and molded objects of these
EP1785449A3 (en) 1998-07-22 2007-08-29 Toyo Boseki Kabushiki Kasisha Aliphatic polyester film and gas barrier film
US6113679A (en) 1998-10-06 2000-09-05 3M Innovative Properties Company Piezo inkjet inks and methods for making and using same
DE60007789T2 (de) 1999-03-26 2004-11-04 Toyo Boseki K.K. Folie aus Polymilchsäure
JP4200405B2 (ja) 1999-04-09 2008-12-24 東洋紡績株式会社 離型フィルムの製造方法
US6498202B1 (en) 1999-12-14 2002-12-24 Lexmark International, Inc Ink jet ink compositions including latex binder and methods of ink jet printing
US6710135B2 (en) * 2000-08-02 2004-03-23 Mitsui Chemicals, Inc. Resin composition and use thereof
WO2002044249A1 (en) * 2000-11-30 2002-06-06 Daicel Chemical Industries, Ltd. Aliphatic polyester copolymer and process for producing the same, biodegradable resin molding based on aliphatic polyester, and lactone-containing resin
NL1017840C2 (nl) 2001-04-12 2002-10-15 Dsm Nv LPA-hybride.
US6905759B2 (en) * 2001-04-23 2005-06-14 Kimberly Clark Worldwide, Inc. Biodegradable films having enhanced ductility and breathability
ATE492389T1 (de) * 2001-04-30 2011-01-15 Treofan Germany Gmbh & Co Kg Verfahren zur herstellung von biologisch abbaubaren verpackungen aus biaxial verstreckten folien und derartige verpackungen
US6896944B2 (en) 2001-06-29 2005-05-24 3M Innovative Properties Company Imaged articles comprising a substrate having a primed surface
US20050106345A1 (en) 2002-01-07 2005-05-19 Toyo Boseki Kabush Iki Kaisha Easy-to-tear stretched aliphatic-polyester film
JP4242109B2 (ja) 2002-04-11 2009-03-18 ユニチカ株式会社 粘着テープ
US6869985B2 (en) 2002-05-10 2005-03-22 Awi Licensing Company Environmentally friendly polylactide-based composite formulations
US20030215628A1 (en) 2002-05-14 2003-11-20 3M Innovative Properties Company Long lasting outdoor tape
US6881458B2 (en) 2002-06-03 2005-04-19 3M Innovative Properties Company Ink jet receptive coating
JP2004010843A (ja) 2002-06-11 2004-01-15 Idemitsu Petrochem Co Ltd ポリ乳酸樹脂組成物
AU2003242475B2 (en) * 2002-06-20 2008-09-25 Toray Industries, Inc. Polylactic acid base polymer composition, molding thereof and film
JP2004034631A (ja) * 2002-07-08 2004-02-05 Nitto Denko Corp 光学フィルム用表面保護フィルム
ATE498648T1 (de) * 2002-10-11 2011-03-15 Univ Connecticut Mischungen von amorphen und semikristallinen polymeren mit formgedächtniseigenscchaften
US6949212B2 (en) 2002-11-27 2005-09-27 3M Innovative Properties Company Methods and devices for stretching polymer films
JP2004204128A (ja) * 2002-12-26 2004-07-22 Mitsubishi Plastics Ind Ltd 熱成形用ポリ乳酸系重合体組成物、熱成形用ポリ乳酸系重合体シート、及びこれを用いた熱成形体
AU2003241790A1 (en) 2003-05-27 2005-01-21 Asahi Kasei Kabushiki Kaisha Biodegradable resin film or sheet and process for producing the same
US20060188706A1 (en) * 2003-06-13 2006-08-24 Mitsuaki Kobayashi Thermally activatable removable adhesive tapes
JP4452574B2 (ja) * 2003-07-18 2010-04-21 三菱樹脂株式会社 脂肪族ポリエステルフィルム及び包装材
JP2005143413A (ja) 2003-11-17 2005-06-09 Fuji Mold:Kk 生分解性樹脂を用いた疑似餌
US20050112352A1 (en) 2003-11-26 2005-05-26 Laney Thomas M. Polylactic-acid-based sheet material and method of making
JP4321717B2 (ja) 2004-02-10 2009-08-26 日東電工株式会社 溶剤含有物除去用粘着シート
EP1785453B1 (en) 2004-06-16 2012-04-18 Unitika Ltd. Polylactic acid-containing resin composition and molded body obtained from same
JP2006035666A (ja) * 2004-07-28 2006-02-09 C I Kasei Co Ltd 複層ポリ乳酸系樹脂フィルム及びその製造方法
JP4394536B2 (ja) * 2004-08-02 2010-01-06 シーアイ化成株式会社 半硬質ポリ乳酸系樹脂フィルム及びその製造方法
JP4811982B2 (ja) * 2004-10-27 2011-11-09 シーアイ化成株式会社 梨地状外観を呈するポリ乳酸フィルムの製造方法
CN104893609A (zh) 2005-04-22 2015-09-09 因赛特解决方案有限责任公司 地面标示胶带
CA2508859A1 (en) 2005-05-30 2006-11-30 Thomas L. Inglis An improved film and sheet for folding packaging containers
WO2007027163A2 (en) 2005-09-01 2007-03-08 Super Film Ambalaj Sanayi Ve Ticaret A. S. Degradable biodegradable polypropylene film
JP2007186562A (ja) 2006-01-12 2007-07-26 Three M Innovative Properties Co ポリ乳酸含有樹脂組成物、ポリ乳酸含有樹脂フィルム及び樹脂繊維
DE202006001693U1 (de) 2006-02-01 2006-03-30 Logo tape Gesellschaft für Selbstklebebänder GmbH Co. KG Biologisch abbaubares Klebeband auf der Basis von nachwachsenden Rohstoffen
JP2007217513A (ja) 2006-02-15 2007-08-30 Taiyo Kagaku Kk ポリ乳酸系樹脂組成物および成形品
JP5030435B2 (ja) 2006-02-17 2012-09-19 大八化学工業株式会社 ポリ乳酸系樹脂積層フィルム、その製造方法、及びその易分解化処理方法
US9163141B2 (en) 2006-04-27 2015-10-20 Cryovac, Inc. Polymeric blend comprising polylactic acid
JPWO2008035762A1 (ja) 2006-09-21 2010-01-28 旭化成ホームプロダクツ株式会社 ポリ乳酸フィルムの製造方法
US7385020B2 (en) 2006-10-13 2008-06-10 3M Innovative Properties Company 2-octyl (meth)acrylate adhesive composition
WO2008051443A1 (en) 2006-10-20 2008-05-02 Natureworks Llc Impact modified polylactide resins
CA2672476C (en) * 2006-12-14 2013-10-22 Pactiv Corporation Expanded and extruded biodegradable and reduced emission foams made with methyl formate-based blowing agents
NL1033719C2 (nl) 2007-04-19 2008-10-21 Synbra Tech Bv Deeltjesvormig expandeerbaar polymelkzuur, werkwijze voor het vervaardigen hiervan, geschuimd vormdeel op basis van deeltjesvormig expandeerbaar polymelkzuur evenals werkwijze voor het vervaardigen hiervan.
CN101104779A (zh) 2007-07-19 2008-01-16 中国科学院长春应用化学研究所 一种可完全生物降解的聚乳酸压敏粘合胶带及其制备方法
CN101397394B (zh) 2007-09-27 2012-05-02 东丽纤维研究所（中国）有限公司 耐水解柔性聚乳酸取向制品及生产方法
JP2009107669A (ja) 2007-10-30 2009-05-21 Unitika Ltd 包装袋
EP2065435A1 (en) * 2007-11-29 2009-06-03 Sukano Management+Services AG Biodegradable polyester compositions
WO2009076458A1 (en) * 2007-12-10 2009-06-18 Toray Plastics (America) , Inc. Biaxially oriented polylactic acid film with high barrier
WO2009076541A1 (en) * 2007-12-11 2009-06-18 Toray Plastics (America), Inc. Process to produce biaxially oriented polylactic acid film at high transverse orientation rates
WO2009120311A2 (en) 2008-03-24 2009-10-01 Michael Riebel Biolaminate composite assembly and related methods
US20110287237A1 (en) 2008-03-24 2011-11-24 Biovation, Llc Wear Resistant Biolaminate Composite Assembly and Related Methods
US20090286090A1 (en) 2008-05-19 2009-11-19 Ting Yuan-Ping R Enhance performance on current renewable film using functional polymer coatings
EP2293949B1 (en) 2008-05-27 2015-07-29 Hewlett-Packard Development Company, L.P. Media for use in inkjet printing
JP5645122B2 (ja) 2008-07-24 2014-12-24 東洋紡株式会社 脂肪族ポリエステル樹脂及びその製造方法
JP5604037B2 (ja) 2008-08-06 2014-10-08 日東電工株式会社 ポリエステル、ポリエステル組成物、粘着剤組成物、粘着剤層及び粘着シート
EP2323788B1 (en) 2008-08-15 2014-07-30 Toray Plastics (America) , Inc. Biaxially oriented polylactic acid film with high barrier
WO2010035911A1 (ja) 2008-09-29 2010-04-01 帝人株式会社 ボリ乳酸フィルム
DE102008042893A1 (de) 2008-10-16 2010-04-29 Wacker Chemie Ag Mischungen zur Herstellung von biologisch abbaubaren Formkörpern auf Basis von aliphatischen Polyestern und in Wasser redispergierbaren Polymerpulvern
US8481620B2 (en) * 2008-10-24 2013-07-09 Kao Corporation Process for producing resin composition
WO2010055903A1 (ja) 2008-11-13 2010-05-20 東洋製罐株式会社 生分解性樹脂組成物
JP5651932B2 (ja) * 2009-06-26 2015-01-14 東洋製罐株式会社 生分解性樹脂組成物
CN102325643B (zh) 2008-12-29 2014-09-24 3M创新有限公司 具有结构化表面的膜及其制造方法
JP5171674B2 (ja) 2009-01-30 2013-03-27 スリーエム イノベイティブ プロパティズ カンパニー ポリ乳酸含有樹脂組成物、ポリ乳酸含有樹脂フィルム及びそれらの製造方法
JP5477944B2 (ja) 2009-04-03 2014-04-23 日東電工株式会社 粘着製品
CN102421819A (zh) 2009-04-06 2012-04-18 梅塔玻利克斯公司 改进聚羟基烷酸酯聚合物的膜加工以及注塑模制的方法
US20120135169A1 (en) 2009-05-19 2012-05-31 Robert Tangelder Bioplastics
BRPI1012778B1 (pt) * 2009-05-19 2021-03-16 Wacker Chemie Ag composições processáveis termoplásticas, composições multicomponentes, processo para preparação dessas composições, processo para a preparação de materiais bioplásticos, materiais bioplásticos e uso dos mesmos
KR101506762B1 (ko) 2009-05-22 2015-03-27 도요보 가부시키가이샤 폴리락트산 수지 조성물 및 필름
EP2442962B1 (en) * 2009-06-16 2014-08-27 3M Innovative Properties Company Debondable adhesive article
US9150004B2 (en) * 2009-06-19 2015-10-06 Toray Plastics (America), Inc. Biaxially oriented polylactic acid film with improved heat seal properties
CN102459219A (zh) * 2009-06-22 2012-05-16 赛格提斯公司 缩酮化合物及其用途
WO2010151872A1 (en) * 2009-06-26 2010-12-29 Toray Plastics (America) , Inc. Biaxially oriented polylactic acid film with improved moisture barrier
CN102597107B (zh) 2009-08-27 2015-09-16 梅塔玻利克斯公司 增韧的聚羟基烷酸酯组合物
WO2011053131A1 (en) 2009-10-30 2011-05-05 Stichting Kennis Exploitatie Rb Starch-based biodegradable polymer; method of manufacture and articles thereof
WO2011060001A1 (en) 2009-11-10 2011-05-19 3M Innovative Properties Company Method for making polylactide films
US8178190B2 (en) 2009-11-17 2012-05-15 Brady Worldwide, Inc. Floor marking tape
JP5351007B2 (ja) * 2009-12-25 2013-11-27 三菱樹脂株式会社 ポリ乳酸系熱収縮性積層フィルム、並びに該フィルムを用いた成形品、熱収縮性ラベル、及び該成形品を用いた、又は該ラベルを装着した容器
WO2011082052A1 (en) 2009-12-28 2011-07-07 3M Innovative Properties Company Plasticized polylactide
CN102115576B (zh) 2009-12-31 2014-09-17 金伯利-克拉克环球有限公司 天然生物聚合物热塑性膜
US8158731B2 (en) 2010-01-27 2012-04-17 Hallstar Innovations Corp. Biopolymer compositions having improved flexibility
WO2011103452A1 (en) * 2010-02-19 2011-08-25 Toray Plastics (America) , Inc. Multi-layer high moisture barrier polylactic acid film
US9492962B2 (en) 2010-03-31 2016-11-15 Toray Plastics (America), Inc. Biaxially oriented polylactic acid film with reduced noise level and improved moisture barrier
WO2011123682A1 (en) 2010-03-31 2011-10-06 Toray Plastics (America) , Inc. Biaxially oriented polylactic acid film with reduced noise level and improved moisture barrier
WO2011123165A1 (en) 2010-03-31 2011-10-06 Toray Plastics (America), Inc. Biaxially oriented polyactic acid film with reduced noise level
KR20130079395A (ko) * 2010-05-19 2013-07-10 미쓰비시 가가꾸 가부시키가이샤 카드용 시트 및 카드
FR2965814B1 (fr) 2010-10-08 2012-11-16 Roquette Freres Plastification de polyesters aliphatiques par des esters alkyliques de dianhydrohexitols
KR20130117798A (ko) 2010-11-26 2013-10-28 닛토덴코 가부시키가이샤 폴리락트산계 필름 또는 시트
EP2679633A4 (en) * 2011-02-24 2017-03-22 Toray Industries, Inc. Polylactic acid-based film
US8530021B2 (en) 2011-03-08 2013-09-10 3M Innovative Properties Company Microstructured tape
JP5811555B2 (ja) 2011-03-17 2015-11-11 東レ株式会社 ポリ乳酸系二軸積層フィルム
EP2702110B1 (en) 2011-04-29 2020-02-19 Hewlett-Packard Development Company, L.P. Thermal inkjet latex inks
JP2013001024A (ja) 2011-06-20 2013-01-07 Toray Ind Inc 延伸フィルム
EP2736994A4 (en) 2011-07-27 2015-03-25 3M Innovative Properties Co MANUALLY RETRACTABLE COVER BELT WITH BACK WITH LOW LIABILITY
WO2013031755A1 (ja) 2011-08-31 2013-03-07 東レ株式会社 ポリ乳酸系フィルム
JPWO2013038770A1 (ja) * 2011-09-12 2015-03-23 東レ株式会社 フィルム
US20130154151A1 (en) 2011-12-20 2013-06-20 Kimberly-Clark Worldwide, Inc. Method for Forming a Thermoplastic Composition that Contains a Renewable Biopolymer
JP2013147580A (ja) 2012-01-20 2013-08-01 Toray Ind Inc ポリ乳酸系配向フィルム
US8980964B2 (en) 2012-02-10 2015-03-17 Kimberly-Clark Worldwide, Inc. Renewable polyester film having a low modulus and high tensile elongation
ES2879250T3 (es) 2012-06-05 2021-11-22 Cj Cheiljedang Corp Mezclas poliméricas biodegradables
JP6041550B2 (ja) 2012-06-15 2016-12-07 日東電工株式会社 ポリ乳酸系樹脂組成物及びそれを用いたフィルム又はシート
US20140087108A1 (en) * 2012-09-26 2014-03-27 Earth Renewable Technologies Extrudable composition derived from renewable resources and method of making molded articles utilizing the same
JP6339939B2 (ja) 2012-10-15 2018-06-06 株式会社カネカ ポリエステル樹脂組成物および該樹脂組成物を含む成形体
JP6247703B2 (ja) * 2012-12-27 2017-12-13 サン−ゴバン パフォーマンス プラスティックス コーポレイション 安定化ポリエステル系組成物
US20140272357A1 (en) 2013-03-12 2014-09-18 Clopay Plastic Products Company, Inc. Film materials comprising biodegradable and/or sustainable polymeric components
WO2014172185A1 (en) 2013-04-15 2014-10-23 3M Innovative Properties Company Adhesives comprising crosslinker with (meth)acrylate group and olefin group and methods
US10174160B2 (en) 2013-04-26 2019-01-08 Xyleco, Inc. Processing hydroxy-carboxylic acids to polymers
CN103265798B (zh) 2013-06-03 2015-11-25 山东昊达化学有限公司 聚乳酸(pla)与乙烯-醋酸乙烯酯共聚物(eva)共混组合物及其成型制品
US9574082B2 (en) * 2013-08-06 2017-02-21 Kaneka Corporation Soft thermoplastic resin composition
DE102013223495A1 (de) 2013-11-18 2015-05-21 Tesa Se Klebeband zum Ummanteln von langgestrecktem Gut wie insbesondere Kabelsätzen und Verfahren zur Ummantelung
JP2015120807A (ja) * 2013-12-20 2015-07-02 花王株式会社 ホットスタンプ用基材
US20170037282A1 (en) 2014-04-11 2017-02-09 3M Innovative Properties Company Adhesives comprising (meth)allyl crosslinker and methods
US9249268B2 (en) * 2014-06-13 2016-02-02 Fina Technology, Inc. Polymeric blends and articles made therefrom
EP3237541B1 (en) * 2014-12-22 2024-07-10 3M Innovative Properties Company Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer
EP3362286B1 (en) 2015-10-16 2019-07-31 Tarkett GDL Decorative multi-layer surface covering comprising polylactic acid
JP6983170B2 (ja) 2015-12-14 2021-12-17 スリーエム イノベイティブ プロパティズ カンパニー 接着剤層を備えたポリ乳酸ポリマー系フィルム
US20190218423A1 (en) * 2015-12-14 2019-07-18 3M Innovative Properties Company Polylactic acid polymer based film comprising an adhesive layer
WO2017112386A1 (en) 2015-12-22 2017-06-29 3M Innovative Properties Company Packaged pre-adhesive composition including a polylactic acid-containing packaging material, adhesives, and articles
CN108699272B (zh) 2016-02-15 2021-10-26 3M创新有限公司 包括结构化表面的聚乳酸聚合物基膜和制品
JP7090555B2 (ja) 2016-05-20 2022-06-24 スリーエム イノベイティブ プロパティズ カンパニー 配向されたポリ乳酸ポリマー系フィルム
US10982090B2 (en) * 2016-06-21 2021-04-20 3M Innovative Properties Company Graphic articles comprising polylactic acid polymer based film
US11407872B2 (en) * 2016-06-21 2022-08-09 3M Innovative Properties Company Foam compositions comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer, articles, and methods of making and using same
EP3475084A4 (en) * 2016-06-22 2020-04-08 3M Innovative Properties Company BARRIER FILM MULTILAYER ARTICLES HAVING A THERMOPLASTIC ALIPHATIC POLYESTER, POLYVINYL ALKANOATE POLYMER AND PLASTICIZER
WO2018106486A1 (en) * 2016-12-05 2018-06-14 3M Innovative Properties Company Composition and films comprising polylactic acid polymer and copolymer comprising long chain alkyl moiety
US10435557B2 (en) * 2017-03-24 2019-10-08 The United States Of America, As Represented By The Secretary Of Agriculture High heat deflection temperature polylactic acids with tunable flexibility and toughness
JP7081335B2 (ja) 2018-03-15 2022-06-07 株式会社リコー 立体造形物の製造装置及び立体造形物の製造方法
US11981810B2 (en) * 2019-03-29 2024-05-14 3M Innovative Properties Company Film comprising polylactic acid polymer suitable for graphic articles

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0587069A1 (en) * 1992-09-04 1994-03-16 MITSUI TOATSU CHEMICALS, Inc. Degradable adhesive film and degradable resin composition
US6005068A (en) 1992-10-02 1999-12-21 Cargill Incorporated Melt-stable amorphous lactide polymer film and process for manufacture thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GAJRIA A M ET AL: "Miscibility and biodegradability of blends of poly(lactic acid) and poly(vinyl acetate)", POLYMER, ELSEVIER SCIENCE PUBLISHERS B.V, GB, vol. 37, no. 3, 1 January 1996 (1996-01-01), pages 437 - 444, XP004065446, ISSN: 0032-3861, DOI: 10.1016/0032-3861(96)82913-2 *
MAJID JAMSHIDIAN ET AL: "Poly-Lactic Acid: Production, Applications, Nanocomposites, and Release Studies", COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY, vol. 9, no. 5, 26 September 2010 (2010-09-26), US, pages 552 - 571, XP055223602, ISSN: 1541-4337, DOI: 10.1111/j.1541-4337.2010.00126.x *

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