EP0458814A1 - Compositions de fluoropolymeres - Google Patents

Compositions de fluoropolymeres

Info

Publication number
EP0458814A1
EP0458814A1 EP90902715A EP90902715A EP0458814A1 EP 0458814 A1 EP0458814 A1 EP 0458814A1 EP 90902715 A EP90902715 A EP 90902715A EP 90902715 A EP90902715 A EP 90902715A EP 0458814 A1 EP0458814 A1 EP 0458814A1
Authority
EP
European Patent Office
Prior art keywords
fluoropolymer
accordance
weight
composition
containing compounds
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.)
Withdrawn
Application number
EP90902715A
Other languages
German (de)
English (en)
Inventor
Hans E. Lunk
Stephen L. Tondre
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.)
Raychem Corp
Original Assignee
Raychem Corp
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 Raychem Corp filed Critical Raychem Corp
Publication of EP0458814A1 publication Critical patent/EP0458814A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
    • H01B3/443—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins from vinylhalogenides or other halogenoethylenic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/267—Marking of plastic artifacts, e.g. with laser
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/10—Greenhouse gas [GHG] capture, material saving, heat recovery or other energy efficient measures, e.g. motor control, characterised by manufacturing processes, e.g. for rolling metal or metal working

Definitions

  • This invention relates to a laser markable fluoropolymer composition, an article, such as an electrical conductor coated therewith, a shaped article, in particular a heat recoverable article, formed from said composition, a method of rendering a fluoropolymer markable by a laser and a method of marking a fluoropolymer surface using a laser.
  • Fluoropolymers are known to be difficult to mark by con ⁇ ventional printing methods. It is at times desirable to mark a fluoropolymer surface, e.g. a fluoropolymer wire coating or cable jacket, marker sleeves, or the like.
  • Needham et al disclose using a laser to mark a polyarylene sulfide com ⁇ position containing an additive system, for example, nickel- •antimony-titanium, or monoazo-nickel complex.
  • an additive system for example, nickel- •antimony-titanium, or monoazo-nickel complex.
  • various fillers such as fiberglass, talc, titanium dioxide, silica or calcium sulfate is mentioned.
  • U.S. Patent No. 4,654,290 to Spanjer discloses laser marking of a composition comprising a resin, such as an epoxy, sili- cone or polyimide, titanium dioxide and optionally an inorganic additive such as chromium oxide or carbon black.
  • the composition may also contain a filler such as aluminum
  • One aspect of this invention provides a laser markable composition
  • a laser markable composition comprising a fluoropolymer having a processing temperature above about 250°C, about 2 to about 7% by weight, based on the weight of the fluoropolymer, of a com ⁇ pound capable of absorbing energy from a laser and about 1 to about 15% by weight, based on the weight of the fluoropo ⁇ lymer, of a mark enhancing organic compound having a decom ⁇ position temperature above the processing temperature of the fluoropolymer, the composition being capable of undergoing a visible color change when exposed to a laser.
  • a further aspect of this invention provides an article coated on the surface thereof with a fluoropolymer com ⁇ position comprising a fluoropolymer having a processing temperature above about 250°C, about 2 to about 7% by weight, based on the weight of the fluoropolymer, of a com ⁇ pound capable of absorbing energy from a laser, and about 1 to about 15% by weight, based on the weight of the fluoropo ⁇ lymer, of a mark enhancing organic compound having a decom ⁇ position temperature above the processing temperature of the fluoropolymer, said composition being capable of undergoing a visible change when exposed to a laser.
  • An additional aspect of this invention provides a heat recoverable article formed from a fluoropolymer composition
  • a fluoropolymer composition comprising a fluoropolymer having a processing temperature above about 250°C, about 2 to about 7% by weight, based on the weight of the fluoropolymer, of a compound capable of absorbing energy from a laser, and about 1 to about 15% by weight, based on the weight of the fluoropolymer, of a mark enhancing organic compound having a decomposition tem ⁇ perature above the processing temperature of the fluoropo ⁇ lymer.
  • Another aspect of this invention provides a method of rendering a fluoropolymer markable by a laser which compri ⁇ ses admixing with the fluoropolymer about 2 to about 7 % by weight, based on the weight of the fluoropolymer, of a com ⁇ pound capable of absorbing energy from the laser and about 1 to about 15% by weight, based on the weight of the fluoropo ⁇ lymer, of a mark enhancing organic compound having a decom ⁇ position temperature above the processing temperature of the fluoropolymer.
  • Yet another aspect of this invention provides a method of marking a surface comprising a fluoropolymer composition which comprises incorporating in the fluoropolymer com ⁇ position, about 2 to about 7% by weight, based on the weight of the fluoropolymer, of a compound capable of absorbing energy from a laser, and about 1 to about 15% by weight, based on the weight of the fluoropolymer, of a mark enhancing organic compound having a decomposition tem ⁇ perature above the processing temperature of the fluoropo ⁇ lymer and exposing the surface of the composition to a laser.
  • Fluoropolymers suitable for use in this invention include thermoplastic and elastomeric fluoropolymers, for example, tetrafluoroethylene homo- and copolymers, such as polytetrafluoroethylene, ethylene-tetrafluoroethylene copo ⁇ lymers tetrafluoroethylene-propylene copolymers; vinylidene fluoride homo- and copolymers, such as polyvinylidene fluoride, vinylidene fluoride-hexafluoropropylene copoly ⁇ mers, vinylidene fluoride-tetrafluoroethylene- hexafluoropropylene terpolymers, ; perfluoroalkoxy polymers; fluorinated ethylene-propylene copolymers; and the like.
  • Preferred fluoropolymers are ethylene-tetrafluoroethylene copolymers (ETFE).
  • composition of this invention comprises about 2 to about 7% by weight, based on the weight of the fluoropo ⁇ lymer, of a compound capable of absorbing energy from the laser employed.
  • the composition comprises about 2 to about 5% of the energy absorber and most preferably about 2 to about 4%, all percentages being by weight, based on the weight of the fluoropolymer.
  • the energy absorber employed depends, in part, on the laser selected. For example, with a neodymium yttrium- arsenic-garnet (Nd:YAG) laser, titanium dioxide is a pre ⁇ ferred energy absorber.
  • Nd:YAG neodymium yttrium- arsenic-garnet
  • the composition of this invention further comprises a mark enhancing organic compound having a decomposition temperature higher than the melt processing temperature of the particular fluoropolymer.
  • a fluoropolymer in general, have relatively high processing temperatures, about 220 to about 400°C.
  • Commercially available ethylene-tetrafloroethylene copolymers preferred in the practice of this invention, have melting points of about 220°C to about 280°C.
  • the organic compound alone does not impart laser markability to the fluoropolymer.
  • a fluoropolymer composition containing the energy absorber and the organic compound are readily markable by a laser.
  • Suitable organic compounds can readily be determined by one skilled in the art.
  • One quick method for identifying mark enhancing compounds is to select compounds having a decomposition temperature above the processing temperature of the fluoropolymer and then heating the compound to a tem ⁇ perature of about 400°C to see if it undergoes a visible color change.
  • the compositions of this invention are typi ⁇ cally light in color and the resulting laser mark is dark.
  • Compositions comprising only one of the energy absorber or organic compound or inadequate amounts of either compounds, unlike the compositions of this invention, are not readily markable by a laser. If the energy output of the laser is adjusted to provide sufficient energy to mark such a com ⁇ position, damage to the fluoropolymer composition may result.
  • Compositions of this invention are markable at relatively low energy levels and the fluoropolymer com ⁇ position suffers no detrimental effects.
  • Preferred organic compounds are sulfur-containing com ⁇ pounds, such as distearyl thiodipropionate, dilauryl thio- dipropionate or oligomers thereof, 4,4'-thiobis(6-t-butyl- m-cresol), or the like, hydroxy-containing compounds, such as tetrakis (methylene 3-(3,5-di-t-butyl-4-hydroxyphenyl) propionate) merhane, 2,2'-oxamidobis(ethyl 3-(3,5-di-t- butyl-4-hydroxyphenyl)prop ⁇ onate, resorcinol monoacetate, or the like, nitrogen-containing compounds, such as triallyl isocyanurate, triallyl cyanurate, bis-melaminium pentate, acetylene diurene, L- -alanine, melamine, acetanilide, guanine, dibenzylamine, dibenzyldipheny
  • composition of this invention comprises about 1 to about 15% by weight, based on the weight of the fluoropo ⁇ lymer, of the organic compound.
  • the composition comprises about 2 to about 10% of the organic compound and most preferably about 2 to about 7%, all percentages being by weight, based on the weight of the fluoropolymer.
  • additives can be added to the polymeric com ⁇ position.
  • additives include for example, antioxidants such as alkylated phenols, e.g. those commercially available as Goodrite 3125, Irganox 1010, Irganox 1035, Irganox 1076, Irganox 1093, Vulkanox BKF, organic phosphite or phosphates, e.g. dilauryl phosphite, Mark 1178, alJylidene polyphenols, e.g. Ethanox 330, thio-bis alkylated phenol, e.g. Santonox R, dilauryl thio-dipropionate, e.g.
  • antioxidants such as alkylated phenols, e.g. those commercially available as Goodrite 3125, Irganox 1010, Irganox 1035, Irganox 1076, Irganox 1093, Vulkanox BKF
  • Carstab DLTDP dimyristyl thiodipropionate
  • Carstab DMTDP distearyl thiodipropionate
  • Cyanox STDP amines, e.g. ingstay 29 etc.
  • UV stabilizers such as [2,2'-thio-bis (4-t-octyl- phenolato)!
  • composition of this invention can be prepared by mixing the fluoropolymer, energy absorbing compound and* organic compound in an internal mixer such as a Banbury or Brabender, a twin screw extruder such as a Brabender or ZSK, or the like, at a temperature above the melting temperature of the fluoropolymer (or above the processing temperature if the fluoropolymer is elastomeric) .
  • an internal mixer such as a Banbury or Brabender, a twin screw extruder such as a Brabender or ZSK, or the like.
  • composition of this invention can be crosslinked, if desired.
  • Crosslinking can be achieved for example by use of a suitable cross-linking agent, such as a peroxide or amine, or by irradiation.
  • the composition is cross-linked by irradiation.
  • the dosage employed in the irradiation step is generally below about 50 Mrads to ensure that the polymer is not degraded by excessive irradiation.
  • the dosage preferably employed depends upon the extent of cross-linking desired, balanced against the tendency of the polymer to be degraded by high doses of irradiation. Suitable dosages are generally in the range 2 to 40 Mrads, for example 2 to 30 Mrads, preferably 3 to 20 Mrads, espe ⁇ cially 4 to 25 or 4 to 20 Mrads, particularly 4 to 15 Mrads.
  • the ionizing radiation can for example be in the form of accelerated electrons or gamma rays. Irradiation is generally carried out at about room temperature, but higher temperatures can also be used.
  • a cross-linking agent Prior to irradiation it is preferred to incorporate a cross-linking agent into the composition.
  • Preferred radiation cross-linking agents contain carbon-carbon unsa ⁇ turated groups. In many cases the cross-linking agent con ⁇ tains at least two ethylenic double bonds, which may be present, for example, in allyl, methallyl, propargyl, or vinyl groups.
  • Preferred cross-linking agent contain at least two allyl groups, especially three or four allyl groups.
  • cross-linking agents are triallyl cyanurate (TAC) and triallyl isocyanurate (TAIC); other specific cross-linking agents include triallyl tri- mellitate, triallyl trimesate, tetrallyl pyromellitate, the diallyl ester of l,l,3-trimethyl-5-carboxy-3-(p_-carboxy- phenyl) indan.
  • TAC triallyl cyanurate
  • TAIC triallyl isocyanurate
  • Other cross-linking agents which are known for incorporation into fluorocarbon polymers prior to shaping, for example those disclosed in U.S. Patents Nos.
  • cross-linking agents can be used. Certain of these cross-linking agents can be used as the organic com ⁇ pound if present in appropriate amounts.
  • compositions can be formed into shaped articles, coatings, or the like, by melt processing, lamination, extrusion or other suitable techniques.
  • a preferred use of the composition of this invention is as an insulation for an elongate electrical conductor, such as a wire or cable.
  • the composition is preferably coated onto the conductor by extrusion, but can be applied by any other method such as tape wrapping or the like.
  • composition of this inven ⁇ tion is in the preparation of heat recoverable articles, particularly articles for use as marker sleeves for wire and cable.
  • a heat recoverable article is one whose dimensional configuration may be made to change when subjected to an appropriate treatment.
  • heat-recoverable articles comprise a heat-shrinkable sleeve made from a polymeric material exhibiting the property of elastic or plastic memory as described, for example, in U.S. Patents Nos. 2,027,962, 3,086,242 and 3,597,372. As is made clear in, for example, U.S. Patent No.
  • the original dimen- sionally heat-stable form may be a transient form in a con ⁇ tinuous process in which, for example, an extruded tube is expanded, while hot, to a dimensionally heat-unstable form but, in other applications, a preformed dimensionally heat- stable article is deformed to a dimensionally heat-unstable form in a separate stage.
  • the polymeric material may be cross-linked (as discussed above) at any stage in the production of the article that will enhance the desired dimensional recoverability.
  • One manner of producing a heat-recoverable article comprises shaping the polymeric article into the desired heat-unstable form, subsequently cross-linking the polymeric material, heating the article to a temperature above the crystalline melting point of the polymer, deforming the article and cooling the article whilst in the deformed state so that the deformed state of the article is retained.
  • application of heat will cause the article to assume its original heat- stable shape.
  • compositions were prepared by blending an ethylene- tetrafluoroethylene copolymer, ETFE, (Tefzel HT-2055 commer- cially available from du Pont), titanium dioxide, and an organic compound in amounts specified in Table I in a Brabender twin screw mixer at 290°C (all zones of the mixer) and at 20 rpm.
  • the organic compounds are designated as follows:
  • Irg 1010 Tetrakis(methylene-3-(3,5-di-t-butyl-4- hydroxyphenyl) propionate) methane (commercially available as Irganox 1010 from Ciba-Geigy)
  • Irgaf 168 Tris(2,4-di-t-butylphenyl)-4,4'-phosphite (commercially available as Irgafos 168 from Ciba-Geigy)
  • compositions were prepared by blending a fluorinated ethylene-propylene copolymer (FEP commercially available from du Pont), titanium dioxide, an organic compound and various additives as set forth in Table II in a Brabender internal mixer having a 60 cc mixing bowl at a temperature of 335°C and run at 50 rpm.
  • FEP fluorinated ethylene-propylene copolymer

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Optics & Photonics (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Printing Methods (AREA)
  • Insulated Conductors (AREA)

Abstract

Une composition de fluoropolymère que l'on peut marquer à l'aide d'un laser, par exemple un laser Nd:YAG, contient environ 2 à environ 7 % d'un absorbeur d'énergie et environ 1 à environ 15 % d'un composé organique améliorant le marquage, ayant une température de décomposition supérieure à la température de traitement du fluoropolymère, tous les pourcentages étant exprimés en poids sur la base du poids du fluoropolymère. La composition subit un changement visible, de préférence irréversible, lorsqu'on l'expose au laser. Ladite composition de fluoropolymère peut comprendre une couche de surface, tel qu'un revêtement, sur un article, tel qu'un conducteur électrique. On peut donner à ladite composition de fluoropolymère la forme d'un article façonné, notamment d'un article thermomodifiable.
EP90902715A 1989-01-25 1990-01-24 Compositions de fluoropolymeres Withdrawn EP0458814A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30284589A 1989-01-25 1989-01-25
US302845 1989-01-25

Publications (1)

Publication Number Publication Date
EP0458814A1 true EP0458814A1 (fr) 1991-12-04

Family

ID=23169457

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90902715A Withdrawn EP0458814A1 (fr) 1989-01-25 1990-01-24 Compositions de fluoropolymeres

Country Status (4)

Country Link
EP (1) EP0458814A1 (fr)
JP (1) JPH04503081A (fr)
CA (1) CA2046881A1 (fr)
WO (1) WO1990008805A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3917294A1 (de) * 1989-05-27 1990-11-29 Huels Chemische Werke Ag Mit laserlicht beschriftbare hochpolymere materialien
GB9005872D0 (en) * 1990-03-15 1990-05-09 British Aerospace A laser markable white pigment composition
WO1992020526A1 (fr) * 1991-05-16 1992-11-26 Raychem Limited Marquage au laser de polymeres fluores
FR2732030B1 (fr) 1995-03-20 1997-04-30 Plastic Omnium Cie Meteriau de revetement a base de polytetrafluoroethylene apte au marquage par laser.
AU2002219838A1 (en) 2000-11-14 2002-05-27 Coltec Industrial Products Inc Abrasion-resistant polytetrafluoroethylene tape
US20030215592A1 (en) 2002-05-14 2003-11-20 3M Innovative Properties Company Imageable multi-wall elastic sleeves
CN100343075C (zh) * 2002-10-01 2007-10-17 Nok株式会社 标记形成方法以及形成标记的成形品
JP4224290B2 (ja) * 2002-11-28 2009-02-12 三菱樹脂株式会社 剥離性フィルム
JP2004321395A (ja) * 2003-04-23 2004-11-18 Vayu:Kk 医療用チューブ
SE531642C2 (sv) * 2007-02-23 2009-06-16 Swerea Kimab Ab Diffusionsfördröjning i fluorplaster
US10256009B2 (en) 2014-06-19 2019-04-09 Saint-Gobain Performance Plastics Corporation Laser-markable insulation material for wire or cable assemblies
US9881714B2 (en) 2014-06-19 2018-01-30 Saint-Gobain Performance Plastics Corporation Laser-markable insulation material for wire or cable assemblies
JP6738181B2 (ja) * 2016-03-30 2020-08-12 住友電気工業株式会社 樹脂組成物及び熱回復物品
KR102630306B1 (ko) 2017-10-31 2024-01-29 에이지씨 가부시키가이샤 성형체, 금속 피복 적층체, 프린트 배선판 및 그것들의 제조 방법
CN118076693A (zh) * 2021-10-13 2024-05-24 大金工业株式会社 组合物、电路基板和组合物的制造方法

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US3557050A (en) * 1967-03-08 1971-01-19 Daikin Ind Ltd Stabilized vinyl fluoride polymers
US3947525A (en) * 1973-01-30 1976-03-30 Allied Chemical Corporation Melt-processable, radiation cross-linkable E-CTFE copolymer compositions
GB8726482D0 (en) * 1987-11-12 1987-12-16 Bicc Plc Marking flourocarbon surfaces

Non-Patent Citations (1)

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Title
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Also Published As

Publication number Publication date
JPH04503081A (ja) 1992-06-04
CA2046881A1 (fr) 1990-07-26
WO1990008805A1 (fr) 1990-08-09

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