US20090142981A1 - Novel Compositions Comprising Structural Isomers Of 1,4-Cyclohexanedimethanol Dibenzoate and Polymer Compositions Containing Same - Google Patents

Novel Compositions Comprising Structural Isomers Of 1,4-Cyclohexanedimethanol Dibenzoate and Polymer Compositions Containing Same Download PDF

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US20090142981A1
US20090142981A1 US11/949,378 US94937807A US2009142981A1 US 20090142981 A1 US20090142981 A1 US 20090142981A1 US 94937807 A US94937807 A US 94937807A US 2009142981 A1 US2009142981 A1 US 2009142981A1
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composition
weight percent
trans isomer
trans
group
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William D. Arendt
Makarand Joshi
Yvonne Aileen Berry-Walker
Paul Steven Lakomiak
Mirnahini Jeganathan
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Eastman Specialties Holdings Corp
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Velsicol Chemical LLC
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Priority to US11/949,378 priority Critical patent/US20090142981A1/en
Assigned to VELSICOL CHEMICAL CORPORATION reassignment VELSICOL CHEMICAL CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ARENDT, WILLIAM D., BERRY-WALKER, YVONNE AILEEN, JEGANATHAN, MIRNAHINI, JOSHI, MAKARAND, LAKOMIAK, PAUL STEVEN
Assigned to GENOVIQUE SPECIALTIES HOLDINGS CORPORATION reassignment GENOVIQUE SPECIALTIES HOLDINGS CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: VELSICOL CHEMICAL CORPORATION
Priority to EP08856230.1A priority patent/EP2222460B1/de
Priority to JP2010536975A priority patent/JP5718643B2/ja
Priority to PCT/US2008/084279 priority patent/WO2009073393A1/en
Priority to CN2008801264508A priority patent/CN101939160A/zh
Priority to BRPI0819711A priority patent/BRPI0819711A8/pt
Priority to ES08856230.1T priority patent/ES2494965T3/es
Publication of US20090142981A1 publication Critical patent/US20090142981A1/en
Assigned to EASTMAN SPECIALTIES HOLDINGS CORPORATION reassignment EASTMAN SPECIALTIES HOLDINGS CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: GENOVIQUE SPECIALTIES HOLDINGS CORPORATION
Priority to US13/870,176 priority patent/US9200137B2/en
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    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
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    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
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    • 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
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/30—Woven fabric [i.e., woven strand or strip material]
    • Y10T442/3472—Woven fabric including an additional woven fabric layer
    • Y10T442/3602—Three or more distinct layers
    • Y10T442/3667—Composite consisting of at least two woven fabrics bonded by an interposed adhesive layer [but not two woven fabrics bonded together by an impregnation which penetrates through the thickness of at least one of the woven fabric layers]
    • 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
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/30—Woven fabric [i.e., woven strand or strip material]
    • Y10T442/3854—Woven fabric with a preformed polymeric film or sheet
    • 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
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
    • Y10T442/659—Including an additional nonwoven fabric
    • Y10T442/673—Including particulate material other than fiber
    • 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
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
    • Y10T442/674—Nonwoven fabric with a preformed polymeric film or sheet

Definitions

  • This invention relates to novel mixtures containing two structural isomers of 1,4-cyclohexanedimethanol dibenzoate in controlled portions. More particularly this invention relates to a method for preparing these isomeric mixtures and the use of these mixtures to impart desirable properties to a variety of polymer compositions including but not limited to hot melt adhesives.
  • CHDM dibenzoate of 1,4-cyclohexanedimethanol
  • the second is a cis form that can be represented by the formula
  • the isomeric distribution in the resultant mixture of cis and trans isomers is determined by the starting materials and hydrogenation catalyst.
  • U.S. Pat. No. 6,919,489, which issued to Orth et al. uses a Raney nickel catalyst doped with rhenium to obtain CHDM with a cis to trans ratio of 0.7 or less from the dimethyl ester of the corresponding dicarboxylic acid having a cis to trans ratio of 1.2 to 2.1.
  • the present invention is based on the discovery of a method for separating a commercially available version of CHDM dibenzoate containing about 70 weight percent of the trans isomer and about 30 weight percent of the cis isomer into fractions containing up to 100 percent by weight of either isomer. Mixtures containing from 1 to 66 weight percent or from 72 to 99 weight percent of the trans isomer have not been reported in the literature and are therefore considered novel compositions.
  • the present inventors have discovered that the properties imparted to polymer compositions, particularly hot melt adhesives, by the present benzoate ester mixtures will vary considerably depending upon the relative concentrations of trans and cis isomers in the mixture.
  • the ability to reproducibly solidify makes the isomers of CHDMDB uniquely suitable for use in hot melt adhesives.
  • the aforementioned Arendt patent contains the curve produced when a sample of CHDMDB is heated in a differential scanning calorimeter. The curve is described as bimodal, with melting points at “about 80 and 123° C.” The higher melting point is more sharply defined.
  • the CHDMDB described in the aforementioned Arendt patent is prepared from a commercially available product containing about 68 weight percent of the trans isomer and about 32 weight percent of the cis-isomer of CHDM.
  • the present invention is based on the discovery that when a mixture of CHDMDB isomers referred to in the aforementioned Arendt patent is heated above its melting point and then gradually cooled, a partial solidification in the form of a crystalline material occurs at a temperature of about 100° C. Analysis of this crystalline material by gas chromatography reveals that it is a mixture typically containing more than 90 weight percent of the trans isomer. The remainder of the molten material solidifies below about 70° C. to a non-crystalline material containing approximately equal weights of the trans and cis isomers.
  • the present trans- and cis-rich mixtures impart different properties to polymer compositions in general and to hot melt adhesives in particular.
  • one of the present CHDMDB mixtures containing more than about 72 percent by weight of the trans isomer as a modifier both the open time and the time required for the adhesive to achieve its ultimate properties are substantially reduced relative to the values obtained using the isomer distribution of the product described in the Arendt patent.
  • the second of these advantages allows for a substantial increase in the maximum speed of a production line on which hot melt adhesives are used to bond two layers of paper, cardboard, fabric or other material. It was also found that adhesives containing a mixture with more than about 72 weight percent of the trans isomer can be designed to be significantly stronger than adhesives based on prior art modifiers.
  • Open time is the time interval during which the adhesive applied to the first substrate remains sufficiently adhesive to effect a bond between this substrate and a second one applied to it.
  • Set time is defined as the time required for bonding once the two substrates to be joined are pressed together.
  • This invention provides novel solid benzoate ester compositions containing both the cis and trans isomers of 1,4-cyclohexane dimethanol dibenzoate wherein the trans isomer constitutes from 1 to 66 or from 72 to 99 weight percent of the compositions.
  • a preferred composition contains 90 to 94 weight percent of the trans isomer, and most preferably more than 95 weight percent of the trans isomer.
  • the composition includes 48 to 52 weight percent of the trans isomer.
  • This invention also provides a method for separating a commercially available form of 1,4-cyclohexane dimethanol dibenzoate (CHDMDB) using melt refining into a crystalline solid composition containing from 72 to about 99 weight percent of the trans isomer of 1,4-cyclohexanedimethanol dibenzoate and a partially crystalline solid containing from 1 up to about 66 weight percent of this trans isomer.
  • CHDMDB 1,4-cyclohexane dimethanol dibenzoate
  • a third aspect of the present invention provides a wide variety of polymer compositions containing any of the isomer mixtures of this invention as a plasticizer or other type of modifier.
  • the ester compositions of this invention impart a variety of desirable properties to polymer compositions.
  • Hot melt adhesives constitute a preferred class of polymer compositions of this invention. These compositions typically comprise 1) a polymer typically selected from the group consisting of olefinic polymers, including but not limited to ethylene/vinyl acetate copolymers and styrene/olefin copolymers, 2) at least one hydrocarbon resin and 3) one of the present CHDMDB isomer mixtures as a modifier.
  • Benzoate ester compositions of this invention containing more than about 72 weight percent of the trans isomer of 1,4-cyclohexanedimethanol dibenzoate typically decrease set times and can increase bond strength of hot melt adhesives, among other advantages.
  • Ester compositions of this invention containing less than about 66 weight percent of this trans isomer can increase open time of these adhesives in addition to providing other advantages.
  • FIG. 1 is a DSC trace of commercially available CHDMDB, Benzoflex 352.
  • FIG. 2 is a DSC trace of trans rich CHDMDB, XP-7007.
  • FIG. 3 is a DSC trace of cis rich CHDMDB, XP-7008.
  • novel benzoate ester mixtures of this invention are prepared by melt refining using the following series of process steps:
  • the CHDMDB used as a starting material to obtain the isomeric mixtures of this invention can be prepared by reacting benzoic acid or a suitable derivative thereof with one of the commercially available forms of 1,4-cyclohexanedimethanol.
  • One such product contains about 70 weight percent of the trans isomer and about 30 weight percent of the cis isomer.
  • the resultant benzoate ester is commercially available as Benzoflex® 352.
  • CHDMDB isomers containing from 72 to 99 weight percent of the trans isomer are particularly suitable for use as modifiers in hot melt adhesives based on the processing advantages of faster set time with a sufficiently long open time relative to Benzoflex® 352.
  • Data in the accompanying examples demonstrate that these isomer mixtures also increase the crystallization rate of the resin component of the adhesive by up to two times relative to Benzoflex® 352 in addition to providing stronger bonds. In practical terms, this reduces the time required for development of maximum bond strength.
  • CHDMDB mixtures containing more than about 34 weight percent of the cis isomer will provide this longer open time.
  • the types of polymers typically used in hot melt adhesives include but are not limited to ethylene/vinyl acetate copolymers, polyolefins, block copolymers based on styrene, acrylates and olefins, olefins based on metallocene catalysts, amorphous polyalphaolefins, acrylic rubber including acrylic triblocks, ethylene/ethyl acrylate copolymers, polyurethanes of the reactive and non-reactive types, polyesters, sulfopolyesters and polyamides.
  • tackifying resins used in hot melt adhesives include but are not limited to aliphatic resins, aromatic resins, pure monomer resins, mixed aromatic and aliphatic resins, rosins, rosin esters, terpene and other mixed monomer resins.
  • the concentration range for these mixtures is from 2 to 50 weight percent, preferably from 15 to 35 weight percent, based on the total weight of the adhesive formulation.
  • the optimum concentration is determined by a number of parameters, including but not limited to desired open and set times, melt viscosity, adhesion and strength.
  • Hot melt adhesives include but are not limited to production of non-woven fabrics, packaging materials, product assembly, book binding adhesives, and adhering of labels.
  • Composite articles may include two bonded layers of materials selected from the group consisting of woven and non-woven fabrics, solid films and sheets formed from natural and synthetic polymers, packaging materials, glue sticks, construction materials, book bindings, and labels.
  • Non-woven fabric may include a diaper or feminine hygiene article.
  • Bonding is achieved using a molten adhesive composition that includes an organic polymer, a resin and a modifier selected from the group consisting of a first mixture containing more than 72 weight percent of the trans isomer of 1,4-cyclohexanedimethanol dibenzoate, preferably 90-94 weight percent of the trans isomer, or a second mixture containing less than 66 weight percent of the trans isomer of 1,4-cyclohexanedimethanol dibenzoate.
  • a molten adhesive composition that includes an organic polymer, a resin and a modifier selected from the group consisting of a first mixture containing more than 72 weight percent of the trans isomer of 1,4-cyclohexanedimethanol dibenzoate, preferably 90-94 weight percent of the trans isomer, or a second mixture containing less than 66 weight percent of the trans isomer of 1,4-cyclohexanedimethanol dibenzoate.
  • CHDMDB compositions of this invention offer processing and/or product advantages relative to other types of plasticizers and modifiers in a variety of polymer compositions, including but not limited to powder coatings, waterborne coatings, hot melt coatings, solvent-based coatings, u.v. curable coatings, and inks of the jet such as hot melt jet ink, varnish such as overprint varnish, solution and water-borne types.
  • the benzoate compositions may include organic polymer and a modifier for said polymer.
  • the modifier may include mixtures of the trans and cis isomers of 1,4-cyclohexane-dimethanol dibenzoate, where the trans isomer constitutes from 72 to 99 weight percent of the composition; or mixtures the isomers where the trans isomer constitutes from 1 to 66 weight percent of the composition.
  • the composition may be a plastisol.
  • the composition may be used in engineering plastics for the fabrication of articles by extrusion or injection molding. Further, the composition may include an organic or aqueous vehicle.
  • the present benzoate compositions act as a processing aid for a variety of plastics, and as both a reinforcing filler and process aid in engineering plastics such as polycarbonates, polyphenylene oxide/styrene blends and similar polymers.
  • processing aides are materials that can be added in small quantities (1-5%) whereupon substantial improvement results in the processing without significant detraction from other properties. Abstracted from Encyclopedia of PVC Volume II, Page 602 Marcel Dekker, Inc, NY.
  • This example describes the preparation of a CHDMDB isomer mixture of the present invention.
  • control 100 parts by weight of a CHDMDB isomer mixture containing about 70 weight percent trans-CHDMDB and about 30 percent of the cis isomer, available as Benzoflex® 352 (hereinafter referred to as “control”), were placed in an oven heated to a temperature of 140° C. The temperature of the oven was then lowered to 100° C. and maintained at this temperature for 16 hours. The liquid portion of the composition was decanted, leaving a solid crystalline material. Analysis of the crystalline material by gas chromatography revealed a trans isomer content of 96 percent. This material will be referred to hereinafter as XP-7007
  • FIG. 1 for the control
  • FIG. 2 for XP-7007
  • FIG. 3 for XP-7008.
  • the peak for the crystalline XP 7008 material occurs at 80.2° C., considerably higher than the peaks for the commercial ester mixture at 56.77° C. and the considerably broader peak for XP-7008, which is indicative of a higher content of the cis isomer.
  • This example compares the effect on resin crystallization rates of the three CHDMDB isomers of example 1.
  • the five resins evaluated are conventionally used in hot melt adhesives and can be described as follows:
  • Wingtack® 95 (Resin B)—A C 5 aliphatic resin available from Goodyear Chemical
  • Nevex® 100 (Resin C)—An aromatic resin available from Neville Chemical
  • Eastotac® H-100R (Resin D)—A hydrogenated aliphatic resin available from Eastman Chemical
  • Crystallization rates were determined using the following procedure: The samples were heated in an oven at 177° C. for 15 minutes, stirred and heated for an additional 15 minutes at the same temperature. The samples were then removed from the oven and allowed to crystallize. The time intervals for initial and complete crystallization are recorded in Table 1.
  • the isomer mixtures are identified as follows:
  • control a commercially available mixture identified as Benzoflex® 352 containing a tran:cis isomer weight ratio of 70:30
  • All of the adhesive formulations were prepared by melting the ingredients other than the polymer at 177° C. while mixing at low speed (400 RPM's). The polymer was then added in slowly and mixed until homogeneous, which required a maximum mixing time of 30 minutes. If degassing was required, the adhesive formulation was placed in a can and heated for one hour in an oven.
  • Inorgox®1010 an antioxidant available from Ciba Geigy Corporation 35 parts of the isomeric CHDMDB to be evaluated, identified as described in Example 1. 25 parts of Kraton® G-1652, a styrene/ethylene/butadiene/styrene copolymer available from Kraton Polymers
  • the formulation to be evaluated was heated to 177° C. in an oven.
  • a 10 mil-thick film of the molten adhesive was applied to the paper strip using a 3 inch-long Bird draw-down bar and a timer was started.
  • a second strip of Kraft paper was applied over the adhesive at the desired time interval using a back and forth stroke with a 50 gram wood block and immediately removed. This procedure was repeated at longer time intervals until no fiber-tearing bonds were observed. The time interval at which this occurred was recorded and appears in Table 2.
  • the formulation had been heated to a temperature of 177° C. in an oven.
  • a 10-mil thick film of the adhesive was applied to the paper strip using a draw down bar and a second paper strip was applied followed by hand pressure.
  • the upper layer of paper was pulled away at a constant rate.
  • Adhesion to a variety of substrates was determined by applying the molten formulation to a sheet of 110-pound lithographic paper and allowing the coating to solidify.
  • the coated paper was cut into 2 by 2 inch (5 cm. by 5 cm.) squares and the coated side applied to glass, white pigmented (W) or clear (C) PVC (polyvinyl chloride), steel, aluminum and oak.
  • the coated paper was heated with a hot air blower to activate the adhesive, following which the resultant composite was allowed to cool.
  • the cooled paper was pulled off the substrate and the percentage of torn paper fibers was evaluated.
  • the temperature at which adhesion failed due to shearing forces was determined by applying a 6 mil thick layer of the molten adhesive to be evaluated on to a piece of Mylar® film.
  • SAFT shear adhesion fail temperature
  • the area of overlap was then heated with a hot air gun to melt the adhesive, forming the bond.
  • the free end of the film strip was attached to a one kilogram weight using a paper clip.
  • the resultant composite was then attached to a support with sufficient clearance to allow the weight to fall.
  • the assembly was then placed in an oven heated to 50° C. The oven temperature was increased by 5° C. every half hour. The temperature at which the weight fell was noted.
  • the temperature of adhesion failure was determined for adhesive formulation 2 (the palletizing adhesive) by application of a 3/16 inch-diameter bead of this formulation to a 2′′ by 16′′ piece of corrugated cardboard.
  • the adhesive was used to form a bonded laminate with a 2′′ ⁇ 2′′ piece of laminated cardboard. At one-minute intervals the strength of the bond was determined. The time required for complete bond failure was recorded.
  • Melt viscosity values were obtained at 177° C. using a model DV II RVT Brookfield viscometer equipped with a Thermosel® apparatus and a number 18 spindle rotating at a speed of 5 RPM was selected to determine apparent viscosity.
  • the results of the evaluations are recorded in the following tables.
  • the samples of CHDMDB are identified as “Control” for the commercial material, XP-007 for the mixture containing 96 percent of the trans isomer and XP 008 for the material containing substantially equal weights of the trans and cis isomers.

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US11/949,378 2007-12-03 2007-12-03 Novel Compositions Comprising Structural Isomers Of 1,4-Cyclohexanedimethanol Dibenzoate and Polymer Compositions Containing Same Abandoned US20090142981A1 (en)

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US11/949,378 US20090142981A1 (en) 2007-12-03 2007-12-03 Novel Compositions Comprising Structural Isomers Of 1,4-Cyclohexanedimethanol Dibenzoate and Polymer Compositions Containing Same
ES08856230.1T ES2494965T3 (es) 2007-12-03 2008-11-21 Nuevas composiciones que comprenden isómeros estructurales de dibenzoato de 1,4-ciclohexanodimetanol y composiciones poliméricas que contienen los mismos
BRPI0819711A BRPI0819711A8 (pt) 2007-12-03 2008-11-21 Composição, métodos para preparar uma composição sólida e para acelerar um tempo de endurecimento e a taxa de cristalização de uma composição de adesivo termorreversível, e, artigo compósito.
PCT/US2008/084279 WO2009073393A1 (en) 2007-12-03 2008-11-21 Novel compositions comprising structural isomers of 1,4-cyclohexanedimethanol dibenzoate and polymer compositions containing same
JP2010536975A JP5718643B2 (ja) 2007-12-03 2008-11-21 １，４−シクロヘキサンジメタノールジベンゾエートの構造異性体を含む新規組成物およびそれを含有するポリマー組成物
EP08856230.1A EP2222460B1 (de) 2007-12-03 2008-11-21 Strukturisomere aus 1,4-cyclohexandimethanoldibenzoat umfassende neue zusammensetzungen und diese enthaltende polymerzusammensetzungen
CN2008801264508A CN101939160A (zh) 2007-12-03 2008-11-21 包含1,4-环己烷二甲醇二苯甲酸酯结构异构体的新的组合物和含有它们的聚合物组合物
US13/870,176 US9200137B2 (en) 2007-12-03 2013-04-25 Compositions comprising structural isomers of 1,4-cyclohexanedimethanol dibenzoate and polymer compositions containing same

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WO2016044238A1 (en) * 2014-09-16 2016-03-24 Eastman Chemical Company Polymeric compositions with improved noise suppression
US9439334B2 (en) 2012-04-03 2016-09-06 X-Card Holdings, Llc Information carrying card comprising crosslinked polymer composition, and method of making the same
DE102013222568B4 (de) * 2012-11-19 2020-03-26 Xerox Corporation Bioerneuerbare schnell kristallisierende phasenwechsel-druckfarben
US10625915B2 (en) 2008-01-21 2020-04-21 Cpi Card Group—Minnesota, Inc. Ultrasecure card package
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WO2018070051A1 (ja) * 2016-10-14 2018-04-19 日立化成株式会社 エポキシ樹脂、エポキシ樹脂組成物、エポキシ樹脂硬化物及び複合材料
JP7194059B2 (ja) * 2019-03-26 2022-12-21 三井化学株式会社 エステル化合物及びその製造方法、熱可塑性樹脂用可塑剤、並びに、熱可塑性樹脂組成物

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US11170281B2 (en) 2012-04-03 2021-11-09 Idemia America Corp. Information carrying card comprising crosslinked polymer composition, and method of making the same
US9183486B2 (en) * 2012-04-03 2015-11-10 X-Card Holdings, Llc Information carrying card comprising a cross-linked polymer composition, and method of making the same
DE102013222568B4 (de) * 2012-11-19 2020-03-26 Xerox Corporation Bioerneuerbare schnell kristallisierende phasenwechsel-druckfarben
US10906287B2 (en) 2013-03-15 2021-02-02 X-Card Holdings, Llc Methods of making a core layer for an information carrying card, and resulting products
US11884051B2 (en) 2013-03-15 2024-01-30 X-Card Holdings, Llc Methods of making a core layer for an information carrying card, and resulting products
WO2016044238A1 (en) * 2014-09-16 2016-03-24 Eastman Chemical Company Polymeric compositions with improved noise suppression
KR102479318B1 (ko) 2014-09-16 2022-12-19 이스트만 케미칼 컴파니 개선된 소음 억제성을 갖는 중합체 조성물
US10077352B2 (en) 2014-09-16 2018-09-18 Eastman Chemical Company Polymeric compositions with improved noise suppression
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KR20170055529A (ko) * 2014-09-16 2017-05-19 이스트만 케미칼 컴파니 개선된 소음 억제성을 갖는 중합체 조성물
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