WO2000005291A1 - Ruban auto-adhesif a deroulement silencieux - Google Patents

Ruban auto-adhesif a deroulement silencieux Download PDF

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Publication number
WO2000005291A1
WO2000005291A1 PCT/US1998/015233 US9815233W WO0005291A1 WO 2000005291 A1 WO2000005291 A1 WO 2000005291A1 US 9815233 W US9815233 W US 9815233W WO 0005291 A1 WO0005291 A1 WO 0005291A1
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WO
WIPO (PCT)
Prior art keywords
sensitive adhesive
pressure
adhesive tape
γçö
unwind
Prior art date
Application number
PCT/US1998/015233
Other languages
English (en)
Inventor
John L. Thiele
Raymond R. Rivera
Dieter Jung
Maria Margareta Luca
Original Assignee
Minnesota Mining And Manufacturing Company
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 Minnesota Mining And Manufacturing Company filed Critical Minnesota Mining And Manufacturing Company
Priority to JP2000561245A priority Critical patent/JP2002521513A/ja
Priority to BR9815954-2A priority patent/BR9815954A/pt
Priority to AU85093/98A priority patent/AU8509398A/en
Priority to EP98935948A priority patent/EP1097180A1/fr
Priority to PCT/US1998/015233 priority patent/WO2000005291A1/fr
Publication of WO2000005291A1 publication Critical patent/WO2000005291A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • 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
    • C09J7/201—Adhesives in the form of films or foils characterised by their carriers characterised by the release coating composition on the carrier layer
    • 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
    • C09J7/22—Plastics; Metallised plastics
    • 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
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
    • 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
    • C09J2421/00—Presence of unspecified rubber
    • 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
    • C09J2423/00—Presence of polyolefin
    • C09J2423/006—Presence of polyolefin 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
    • C09J2453/00—Presence of block copolymer
    • 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
    • C09J2483/00—Presence of polysiloxane
    • C09J2483/005—Presence of polysiloxane in the release coating

Definitions

  • the present invention relates to preparing pressure-sensitive adhesive tape.
  • Pressure-sensitive adhesive tape often includes a backing, a release coating, and an adhesive composition.
  • Release coatings such as, for example, silicone-based release coatings
  • pressure-sensitive adhesive compositions such as, for example, (meth)acrylate-based pressure-sensitive adhesive compositions and natural rubber-based pressure-sensitive adhesive compositions, to decrease the unwind force of a roll of tape. It is, however, often difficult to provide a controlled unwind force with silicone-based release coatings. If the unwind force is too low, the pressure-sensitive adhesive of the roll of tape may release or slide from the backside of the underlying lap causing the roll of tape to telescope.
  • the release coating may be fully or partly transferred to the pressure-sensitive adhesive layer upon unwinding of the roll, resulting in a partial detackifying of the adhesive and/or decrease of the peel adhesion of the tape to a substrate.
  • Transfer of the release coating to the adhesive layer can be reduced or avoided when using a release coating that includes the reaction product of an MQ silicone resin and an organopolysiloxane bearing one or more reactive (meth)acrylate groups as described in U.S. Patent No. 5,494,979.
  • Pressure-sensitive adhesive tapes are used in a wide variety of technical fields. When applied by end-users such tapes are often adhered at relatively low unwinding forces such as, for example, 0.1 - 30 m min "1 , whereas in some industrial applications such as, for example, packaging and diaper manufacturing, adhesive tapes are applied semi-automatically or automatically at high unwind speeds of, for example, 100 - 150 m/min "1 or more.
  • One of the problems encountered with adhesive tapes is that unwinding the tape from the roll both at low and high unwinding speeds frequently results in an unacceptably high level of noise which causes discomfort and, in industrial applications, potential hearing damage to the workers in the taping area. The noise at unwind is influenced by the unwind force.
  • Adhesive tapes that include a silicone-based release coating may exhibit low noise at unwind.
  • the noise level is influenced by both the release coating and the type of pressure-sensitive adhesive of the tape.
  • a tape system that can be prepared to produce low noise is a tape system that includes an epoxy-organopolysiloxane release composition and a synthetic rubber-based pressure-sensitive adhesive composition, as described in WO 94/28,080.
  • Pressure-sensitive adhesive compositions based on, e.g., acrylate or natural rubber are typically coated onto a backing using organic solvent- based and dispersion coating processes.
  • Organic solvent-based coating operations are undesirable from an environmental point of view and are often characterized by low coating speeds relative to hot melt coating processes.
  • Dispersion coating processes are also often characterized by low coating speeds relative to hot melt processes.
  • the invention features a pressure-sensitive adhesive tape that includes a backing having a first major surface and a second major surface, a pressure-sensitive adhesive provided on the first major surface, and a release coating provided on the second major surface.
  • the release coating includes the reaction product of:
  • R 1 independently from each other is an alkyl group having 1-3 carbon atoms
  • R 2 independently from each other is an optionally branched alkyl group with
  • R 5 C C — C — O — , CHY, — , CH 2 Y — , or HCO
  • R 5 independently from each other is H or an optionally branched alkyl group having 1-5 carbon atoms
  • R 6 independently from each other is H or R 1 , X independently from each other is F or Cl,
  • Y independently from each other is F, Cl or OH, x is 0 or a number of up to 200, y is 0 or a number of up to 40, z is 0 or a number of up to 200, with the provisos that
  • the amount of the radiation-curable organopolysiloxane of formula (II) is no greater than about 15 wt %
  • the pressure-sensitive adhesive tape when in the form of a roll, exhibits no greater than about 80 dB(A), upon unwind at unwind speeds of up to about 110 m/min, when measured according to the
  • the pressure sensitive adhesive tape when in the form of a roll, exhibits less than 75 dB(A), upon unwind at unwind speeds of up to about 100 m/min, when measured according to the "Noise Level at Free-Standing Unwind Stand” test.
  • the pressure-sensitive adhesive tape when in the form of a roll, also preferably exhibits an unwind force of at least about 0.5 N/cm, at an unwind speed of about 0.3 m/min.
  • the backing includes an oriented polymeric film selected from the group consisting of polyester, polyolefin, and combinations thereof. In some embodiments, the backing layer has a thickness of about 20
  • the pressure-sensitive adhesive is a hot- melt coatable pressure-sensitive adhesive.
  • the adhesive is selected from the group consisting of ABA-type, and AB-type synthetic resin block copolymers, where A is a thermoplastic block and B is a rubber block.
  • the pressure-sensitive adhesive includes a block copolymer selected from the group consisting of styrene-isoprene-styrene, styrene-butadiene-styrene, styrene-ethylene-butylene-styrene, and combinations thereof.
  • the pressure-sensitive adhesive further includes one or more tackifiers.
  • the pressure-sensitive adhesive has a thickness of about 10-50 ⁇ m.
  • the invention features the use of the above- described tape as a packaging or box-sealing tape.
  • the method features uwinding a roll of the above-described pressure-sensitive adhesive tape and adhering the tape to a cardboard substrate (e.g., a box).
  • the invention features the use of the above- described pressure-sensitive adhesive tape as low-noise packaging and box- sealing tapes.
  • the invention provides pressure-sensitive adhesive tapes that have a relatively low noise-level at unwind, and an unwind force that is sufficiently high to allow for stable rolls of tape and that is sufficiently low to allow for smooth unwinding.
  • the adhesive tapes can also be formulated to have a relatively low shockiness index.
  • the invention also provides hot-melt coatable pressure-sensitive adhesive tapes that are particularly useful as packaging tapes and box sealing tapes.
  • the pressure-sensitive adhesive tapes of the invention can be selectively prepared to exhibit a noise upon unwinding of preferably no greater than about 80 dB(A), at unwind speeds of about 110 m/min, as measured according to the test method "Noise Level at Free-Standing Unwind Stand" described below.
  • the composition of the precursor of the release coating can be selected so that the unwind force is at least about 0.5 N/cm, at a low unwind speed of about 0.3 m/min.
  • the pressure-sensitive adhesive tapes of the invention include a backing, a pressure-sensitive adhesive on a first major surface of the backing, and a release coating on a second major surface of the backing.
  • Useful backing materials for the pressure-sensitive adhesive tape include films and layers of various stiffness. Preferred backings are flexible. Suitable backing materials include, e.g., polymeric films and layers, paper (e.g., treated paper) films and layers, layers of non-wovens, laminates (such as, for example, polyacrylate foams laminated on both sides with polyolefin films, and papers laminated or jig-welded with polyethylene terephthalate), metals, and combinations thereof.
  • Useful polymeric films and layers include, for example, polyolefin polymers, monoaxially oriented polypropylene (MOPP), biaxially oriented polypropylene (BOPP), simultaneously biaxially oriented polypropylene (SBOPP), polyethylene, copolymers of polypropylene and polyethylene, polyester polymers, polycarbonate polymers, polymethacrylate polymers, cellulose acetate, polyester (e.g., biaxially oriented polyethylene terephthalate), vinyl acetates, and combinations thereof.
  • Useful backings also include surface modified backings modified by, e.g., flame treatment, corona treatment, and roughening.
  • Preferred backings have a thicknesses between 20 ⁇ m and 3,000 ⁇ m, preferably between 20 ⁇ m and l,000 ⁇ m, more preferably between 25 ⁇ m and lOO ⁇ m.
  • Suitable pressure-sensitive adhesive (PSA) compositions include hot-melt coatable, solvent coatable, transfer-coatable, and latex coatable PSA compositions.
  • Pressure-sensitive adhesive compositions are normally tacky at room temperature and can be adhered to a surface by application of, at most, light finger pressure.
  • useful adhesive compositions include thermoplastic elastomer, polyacrylate, polyvinyl ether, diene- containing rubber such as natural rubber, polyisoprene, and polybutadiene- acrylonitrile polymer; amorphous polyolefin; silicone; ethylene containing copolymers such as, e.g., ethylene vinyl acetate, ethylacrylate, and ethyl methacrylate; polyurethane; polyamide; epoxy; polyvinylpyrrolidone and vinylpyrrolidone copolymer; polyester; and mixtures of the above.
  • a general description of useful pressure sensitive adhesive compositions can be found in Encyclopedia of Polymer Science and Engineering, vol. 13, Wiley-Interscience Publishers (New York, 1988). Additional description of useful pressure sensitive adhesives can be found in Encyclopedia of Polymer Science and Technology, vol. 1, Interscience Publishers (New York, 1964).
  • Preferred pressure-sensitive adhesive compositions are hot-melt coatable and include one or more synthetic rubber block copolymers that preferably are of the ABA- or AB-block type, where A is a thermoplastic block and B is a rubbery block.
  • the block copolymers can be linear, branched, radial, and combinations thereof.
  • suitable block copolymers include styrene-isoprene-styrene (SIS), styrene-butadiene- styrene (SBS), styrene-ethylene-butadiene-styrene (SEBS), styrene-butadiene (SB), ethylene-propylene-diene, and hydrogenation products thereof.
  • SIS styrene-isoprene-styrene
  • SBS styrene-butadiene-styrene
  • SEBS styrene-ethylene-butadiene-sty
  • Suitable commercially available block copolymers include, e.g., those block copolymers available under product numbers 1107, 1101, 1111, 1112, and 1117 from Shell Chemical Company under the KratonTM trademark.
  • Other useful block copolymers include VectorTM 4100 series block copolymers, available from Dexco Polymers.
  • Hot-melt coatable, pressure-sensitive adhesive compositions preferably additionally include tackifiers, which can be solid, liquid, and combinations thereof.
  • Suitable solid tackifiers include, e.g., rosin, rosin derivatives, hydrocarbon resins, polyterpenes, coumarone indenes, and combinations thereof.
  • Suitable liquid tackifiers include, e.g., liquid hydrocarbon resins, hydrogenated liquid polystyrene resins, liquid polyterpenes, liquid rosin esters, and combinations thereof. Suitable tackifier resins are described in D. Satas, Handbook of Pressure-sensitive Adhesive, loc. cit, and pp. 527-544.
  • Preferred commercially available tackifier resins include Escorez 2203 and 1310 from Exxon Chemicals, WingtackTM 95 and WingtackTMPlus from the Goodyear Tire & Rubber Company, and RegalrezTM 1018 and 1078 from Hercules, Inc.
  • the hot-melt coatable, pressure-sensitive adhesive compositions can also include one or more additives such as, for example, bonding agents, plasticizers, antioxidants, stabilizers, fillers, oils, polymer additives such as, for example, poly (ethylene vinyl acetate), dyes, pigments and combinations thereof.
  • the hot-melt coatable, synthetic rubber based pressure-sensitive adhesive is preferably prepared using a compounder, for example, a twin screw extruder to mix the components of the adhesive. A suitable twin screw extruder is described, for example, in the Short Course Notes of the Technical Association of the Pulp and Paper Industry, 1981, Hot Melt Coatings, "Liquid Resin Injection System for Continuous Mixing of
  • the extruder described includes a port valve for injecting liquid resins.
  • the preferred release coating of the pressure-sensitive adhesive tape includes the reaction product of: (i) 15-35 wt.% (preferably 20-35 wt.%, more preferably 25-35 wt.%) of one or more silicone MQ resins bearing one or more (meth)acrylic functional groups and, optionally, one or more vinyl and/or ethenylene functional groups; (ii) 50-85 wt.% (preferably 60-80 wt.%, more preferably 65-80 wt.%) of one or more radiation curable (preferably UV-curable) organopolysiloxanes of formula I described below;
  • an effective amount preferably between 0.1 and 5 wt.%, more preferably between 0.5 and 4 wt.%) of one or more photoinitiators.
  • weight percentages given above refer to the sum of the masses of components (i), (ii) and (iii), which add up to 100% wt.
  • Preferred silicone MQ resins are three-dimensional silicone resin that include quadrofunctional silicate groups Q, and monofunctional end-capping groups M
  • X 1 and X 2 preferably have the following meanings: X 1 independently from each other is an optionally branched alkyl group having
  • X 2 independently from each other is an optionally branched alkyl group having 1 to 8 carbon atoms, wherein 1 or 2 - CH 2 - groups may be replaced by
  • H H X 4 X 4 and wherein one or two CH 3 groups may be replaced with H 2 C CX 4 -, HOCH 2 - or halogen-CH 2 - with X 4 being independently from each other H, CH 3 , C 2 H 5 or
  • Preferred MQ resins have an M/Q ratio between 0.1 and 10, preferably between 0.2 and 8, (more preferably between 0.25 and 7.5), an average molecular weight M think of between 500 and 100,000 g/mol (preferably between 500 and 80,000 g/mol, more preferably between 600 and 60,000 g/mol), and an OH-content of between 0.0001 and 4 wt.% (more preferably of between 0.005 and 2.5 wt.%) with respect to the mass of the MQ resin.
  • MQ resins are described, for example, in EP 0,464,706 incorporated herein.
  • Preferred MQ resins include the MQ resins defined in claim 1 of US 5,494,979 and designated there as siloxane resin A.
  • Particularly preferred MQ resins are those resins disclosed, for example, in US 5,494,979 at col. 11, 11. 12-15.
  • MQ resins are commercially available, for example, from the silicone division of General Electric Co.
  • One method for preparing (meth) acrylate, vinyl and/or ethenylene modified siloxane MQ resins of component (i) includes reacting one or more
  • One preferred method for preparing acrylate-modified MQ resins includes reacting an MQ resin with one or more (meth)acrylate substituted organopolysiloxanes in the presence of an acidic equilibration catalyst at a temperature of about 0 to 140°C as described in US 5,494,979, which is incorporated herein.
  • Preferred meth(acrylate) substituted organopolysiloxane compounds include, e.g., the compounds of formulae I and II described below and the organopolysiloxane compounds described in U.S. Patent No. 5,494,979, col. 11, 1. 16 - col. 13, 1. 15, and that are designated therein as organopolysiloxanes B.
  • Suitable equilibrating catalysts are described in U.S.
  • R 1 independently from each other is an alkyl group having 1-3 carbon atoms
  • R 2 independently from each other is an optionally branched alkyl group with
  • I I II may be replaced with — C — , - — C — , — O — , — C — ,
  • R 5 c C — C — O — , CHY 2 — , CH 2 Y — , or HCO —
  • R 5 independently from each other is H or an optionally branched alkyl group having 1-5 carbon atoms
  • R 6 independently from each other is H or R 1
  • X independently from each other is F or Cl
  • Y independently from each other is F, Cl or OH
  • x is 0 or a number of up to 200
  • y is 0 or a number of up to 40
  • z is 0 or a number of up to 200, with the provisos that
  • the organopolysiloxanes of formula I are long-chain organopolysiloxanes where 60 ⁇ x+y+z ⁇ 300, preferably 80 ⁇ x+y+z ⁇ 250. In the organopolysiloxanes of formula I, at least one of R 2 exhibits one or more (meth)acrylate groups and, optionally one or more vinyl and/or ethenylene groups.
  • R 2 and/or y are selected so that the acrylate, vinyl and/or ethenylene functionality of the organopolysiloxane compounds on average is at least 2 and more preferably at least 2.1 in order to obtain upon curing (e.g., UV or electron (E)-beam curing) a crosslinked, 3-dimensional release coating.
  • group R 2 include • H 3 C —
  • H 2 C CH — C — O — CH 2 — C — CH 2 — O — (CH 2 ) r —
  • organopolysiloxanes of formula I can be prepared using the methods described in DE 38 10 140 and incorporated herein.
  • Tego ® RC 726 is commercially available from Th. Goldschmidt AG, Essen, Germany.
  • Tego ® RC 726 was analytically determined by the present inventors, by nuclear magnetic resonance (NMR) spectroscopy ('H, 13 C, 29 Si), and gel permeation chromatography (GPC), to be
  • a 2 is — (CH 2 ) 4 OC (CH 2 ) 9 CH 3 ,
  • a 3 is — (CH 2 ) 5 — CH 3 , m is 0.7, n is 0.1, and o is 0.2.
  • Tego ® RC 7008 A particularly useful example of a mixture of components (i) and (ii) is Tego ® RC 708, which is commercially available from Th. Goldschmidt.
  • Tego ® RC 708 was determined by the present inventors to include about 25-30% MQ resins and about 70% RC 726.
  • the MQ resin component of Tego ® RC 708 is an acrylate-modified MQ-resin.
  • the MQ resin was determined by the present inventors, using NMR and GPC analysis, to have approximately the following properties: a polystyrene equivalent number-average molecular weight of about 3000 with a heterodispersity index of about 2.8, indicating a very broad molecular weight distribution; and a ratio of M units over Q units of about 48-56%: 44-52%) where the
  • the preferred radiation curable (e.g., UV or E-beam curable) organopolysiloxanes of formula (II) are:
  • the organopolysiloxanes of formula II are short-chain compounds where 5 ⁇ a+b+c ⁇ 60, preferably 10 ⁇ a+b+c ⁇ 40, more preferably 10 ⁇ a+b+c ⁇ 30.
  • the organopolysiloxanes of formula II are preferably added to the precursor of the release coating to improve the dissolvability of the (meth)acrylate-modified MQ resins of component (i) in the (meth)acrylate- modified organopolysiloxane compounds.
  • R 2 and/or y in the organopolysiloxanes of formula II are selected such that the average acrylate, vinyl and/or ethenylene functionality is at least 2, more preferably at least 2.1.
  • organopolysiloxanes of formula II can be prepared using the methods described in DE 38 10 140.
  • a useful example of a organopolysiloxane of formula II is Tego ®
  • Tego ® RC 711 commercially available from Th. Goldschmidt AG, Essen, Germany. Tego ® RC 711 was analytically determined by the present inventors, using NMR spectroscopy ('H, 13 C, 29 Si) and GPC, to be
  • Tego ® RC 715 Another example of an organopolysiloxane of formula II is Tego ® RC 715, which is commercially available from Th. Goldschmidt AG.
  • Tego ® RC 715 was analytically determined by the present inventors, by NMR spectroscopy ( ⁇ , 13 C, 29 Si) and GPC, to be
  • organopolysiloxanes of formula II include, e.g.,
  • the amount of the short-chain organopolysiloxanes of formula II is selected to allow the acrylate modified MQ resin of component (i) to dissolve in the release coating composition, and to allow sufficient anchoring of the release coating to the backing. It was found to be essential that the amount of such components be less than 25 wt. %, preferably no greater than about 15 wt. %), and more preferably about 10 wt %> or less. If the concentration of the short-chain organopolysiloxane components in the release coating of the present invention is more than 15 wt %>, the noise level upon unwinding of the adhesive tape tends to become unacceptably high.
  • Tego ® RC 708 which, as indicated above, is a mixture of 30 wt. % of an acrylate modified MQ resin and 70 wt. % Tego ® RC726, is recommended by the preliminary data sheet of Tego ® RC 708 published by Goldschmidt AG in November 1993, to be blended with at least 30 wt. % of Tego ® RC 711.
  • a minimum of 30 wt. % of Tego ® RC 711 in combination with Tego ® RC 708 is also mentioned, for example, in T. Ebbrecht et al., Silicone Acrylate Systems, lecture on the COWISE Conference, Chicago, U.S.A., March 2-3, 1992, p. 7, charts 10 and 11.
  • photoinitiators examples include benzyl ketals, benzoin ethers, acetophenone derivatives, ketoxime ethers, benzophenone, benzo- or thioxanthones, etc..
  • Specific examples of photoinitiators include: 2,2- diethoxyacetophenone; 2- or 3- or 4- bromoacetophenone; benzoin; benzophenone; 4- chlorobenzophenone; 4- phenylbenzophenone; benzoquinone; 1- chloroanthroquinone; p- diacetyl-benzene; 9, 10 dibromoanthracene; l,3-diphenyl-2-propanone; 1,4-naphtyl-phenyl ketone;
  • An example of a suitable photoinitiator is Darocure 1173, which is commercially available from Ciba Geigy, Switzerland.
  • the concentration of the components of the radiation curable release coating composition are preferably selected within the ranges as given above so that the precursor of the release coating forms a coatable mixture or solution. If necessary a small amount of solvent such as, for example, heptane may be added.
  • the precursor of the release coating composition may also include additives such as, for example, stabilizers, dyes, pigments, antioxidants, fillers and combinations thereof.
  • additives such as, for example, stabilizers, dyes, pigments, antioxidants, fillers and combinations thereof.
  • the amount of such additives preferably is no greater than 25 wt.%>, more preferably no greater than 20 wt.%, of components (i), (ii) and (iii).
  • the pressure-sensitive adhesive tape can be made by coating the precursor of the release coating onto a major surface of the backing and subsequently radiation-curing the release coating. The adhesive can then be applied to the other major surface of the backing. The processes may be carried out separately, in-line sequentially, and simultaneously. Both the precursor of the release coating and the adhesive coating are preferably selected to allow for solvent-less coating.
  • the backing may be treated to enhance adhesion of the composition to the backing.
  • treatments include chemical priming, flame treatment, corona treatment, and combinations thereof.
  • Pressure-sensitive adhesive tapes according to the present invention wherein the (meth)acrylate modified silicone MQ resins of component (i) are present in an amount of 25-35 wt.%>, the long-chain organopolysiloxane compounds of formula I (component (ii)) are present in an amount of 55-75 wt.% and the short-chain organopolysiloxane compounds of formula II (component (iii)) are present in an amount of 0-10 wt.%>, are especially preferred for use as packaging and box-sealing tapes.
  • the objectives and advantages of this invention are further illustrated by the following examples but the particular materials and the amounts thereof recited in these examples should not be construed to unduly limit the invention. Several test methods which are utilized in the examples, are also described. Parts given herein are parts by weight.
  • a 50 mm wide roll of adhesive tape is unwound in a tangential direction at 25 m/min or 110 m/min, respectively, using HSU- 1000 High
  • Test 815 sound probe (Testo, Lenkirch, Germany) is placed 1 m from the unwinding in the direction of the rotation axis around which the tape roll is unwound. The sound level in dB(A) is read from the meter and recorded.
  • a 50 mm wide roll of adhesive tape is placed horizontally in the middle of a wooden box having the dimensions of 60 cm x 60 cm x 60 cm.
  • the roll is unwound in a tangential direction at a speed of 20 m/min whereby the tape is travelling through a vertical slit (2 cm x 8 cm) in the front wall of the wooden box.
  • One of the side walls of the box next to the front wall of the box has a second vertical slit (2cm x 8 cm) facing the horizontally placed roll and oriented parallel to the rotation axis of the tape roll.
  • the sound level in dB(A) is read from the meter and recorded.
  • the force required to unwind a 50 mm wide roll of tape at high speed is measured using the HSU- 1000 Unwind Machine having an unwind motor, a winder station, and the capability of electronically evaluating the unwind behavior of the adhesive tape.
  • the output is then printed out in the form of a graph showing the actual unwind force in N/cm as a function of distance along the tape.
  • the shockiness index (SI) is calculated from such graph as the ratio (maximum unwind force-minimum unwind force)/ average unwind force.
  • the unwind force at a low speed of 0.3 m / min is measured according to Association Des Fabricants Europeens De Rubans Auto- Adhesifs (AFERA) 4013.
  • the unwind force is recorded in N/cm and the average unwind force and the shockiness index is obtained as described above.
  • Static shear to fiberboard is measured according to AFERA 4012 with the exception that instead of the stainless steel substrate required by this method, a substrate of Mosinee C696 virgin fiberboard (Mosinee Paper Corp, Wisconsin) is used. The adhered sample area is 1.27 x 1.27 cm and a weight of 1 kg is used. Time to bond failure is recorded in minutes.
  • Rolling ball tack of the adhesive surface is measured according to PSTC 6 (Pressure-Sensitive Tape Council, Chicago, Illinois). The results were recorded in mm.
  • Results were measured on tape rolls which had been freshly prepared and stored at 23°C and a relative humidity of 50% for approximately one week, and on aged tape rolls.
  • the aging procedure included storing of the above mentioned rolls at 50°C in a forced air oven for 11 days. The tape rolls were reconditioned to 23 °C and 50% relative humidity for at least 24 hrs before testing
  • Test procedures used in Example 7 include the following.
  • the noise level at free-standing unwind is determined by unwinding a 48 mm wide roll of adhesive tape in a tangential direction at 5, 25, 60 and 100 m/min, respectively, using a HSU- 1000 High Speed Unwind Machine (Chemsultants International Network, Cincinnati, Ohio).
  • a Real-Time Frequency analyzer Type 2144 with microphone type 4185 sound probe is determined by unwinding a 48 mm wide roll of adhesive tape in a tangential direction at 5, 25, 60 and 100 m/min, respectively, using a HSU- 1000 High Speed Unwind Machine (Chemsultants International Network, Cincinnati, Ohio).
  • the force required to unwind a 48 mm wide roll of tape at 5, 25, 60 and 100 m/min is measured using a HSU- 1000 Unwind Machine having an unwind motor, a winder station, and the capability of electronically evaluating the unwind properties of the adhesive tape.
  • the output is printed in the form of a graph showing the actual unwind force in N/cm as a function of distance along the tape.
  • the shockiness index (SI) is calculated form such graph as the ratio (maximum unwind force-minimum unwind force)/average unwind force. Unwind Force at Low Speed Test II
  • the unwind force at a speed of 12 in/min (0.3 m/min) is measured according to PSTC 8 (Pressure-Sensitive Tape Council, Chicago, Illinois, U.S.A.).
  • PSTC 8 Pressure-Sensitive Tape Council, Chicago, Illinois, U.S.A.
  • the unwind force is recorded in N/cm and the average unwind force and the shockiness index are obtained as described above.
  • Peel adhesion is measured according to PSTC 1 from a stainless steel substrate at 12 in/min (0.3 m/min). Results are recorded in oz/in.
  • Rolling ball tack of the adhesive surface is measured according to PSTC 6. The results are recorded in mm.
  • Results were measured on tape rolls which had been freshly prepared and stored at 23°C and a relative humidity of 50% for approximately, one week, and on aged tape rolls.
  • the aging procedure included storing of the above mentioned rolls at 120°F (50°C) in a forced air oven for 11 days. The tape rolls were reconditioned to 23 °C and 50% relative humidity for at least 24 hrs before testing.
  • a 35 ⁇ m thick, biaxially-oriented polypropylene (BOPP) film was corona-treated on one side and then coated with a UV-curable precursor of a release coating composition that included 100 parts Tego ® RC 708 (Th. Goldschmidt AG, Essen, Germany), and 3 parts of Darocur 1173 UV photoinitiator (Ciba-Geigy, Basel, Switzerland ) based on 100 parts of Tego ® RC 708.
  • the release coating was prepared using a five-roll coater at a coating weight of the precursor of 0.6 g/m 2 (thickness of the cured release coating about 0.6 ⁇ m), and then cured by UV radiation (120 W/cm) using lamps Model F-450 (Fusion UV Systems, Inc., Gaithersberg, Maryland) in a nitrogen atmosphere.
  • the adhesive composition was applied at a coating weight of 18 g/m 2 corresponding to a thickness of about 18 ⁇ m.
  • the tape was rolled up onto itself, slit into 50 mm rolls and stored as described above to give freshly prepared or aged, respectively, tape rolls.
  • Example 1 was repeated with the exception that the coating weight of the precursor was reduced to 0.42 and 0.30 g/m 2 , respectively.
  • Example 1 was repeated with the exception that the precursor of the release coating composition included a mixture of Tego ® RC 708 (Th. Goldschmidt AG) and Tego ® RC 711 (Th. Goldschmidt AG) instead of 100 parts of Tego ® RC 708.
  • the weight ratio of Tego ® RC 708 to RC 711 was 95 parts/5 parts and in Example 5, the weight ratio was 90 parts/10 parts.
  • Example 1 was repeated with the exception that the precursor of the release coating composition included instead of 100 parts of Tego ® RC 708, a mixture of Tego ® RC 726 and the same acrylate modified MQ silicone resin contained in Tego ® RC 708, in a weight ratio of 80 parts/20 parts.
  • a 35 ⁇ m thick, biaxially-oriented polypropylene (BOPP) film was corona-treated on one side and then coated with a UV-curable precursor of a release coating composition that included 100 parts Tego RC 708 and 3 parts of Darocur 1173 UV photoinitiator (Ciba-Geigy, Basel, Switzerland) based on 100 parts of RC 708.
  • the release coating was prepared using a five-roll coater at a coating weight of the precursor of 0.6 g/m 2 (thickness of the cured release coating about 0.6 ⁇ m), and then cured by UV radiation using lamps (Fusion UV Systems, Inc., Gaithersberg, Maryland) in a nitrogen atmosphere.
  • the opposite side of the BOPP was flame-treated and then coated with a synthetic rubber resin pressure-sensitive adhesive that included Kraton
  • the adhesive composition also included 1.5 parts of Irganox 1076 antioxidant (Ciba Geigy) and 1.5 parts Cyanox LTDP antioxidant (Ciba Geigy).
  • the adhesive composition was applied at a coating weight of 23 g/m 2 corresponding to a thickness of about 23 ⁇ m.
  • the tape was rolled up onto itself, slit into 48 mm rolls, and stored as described above to give freshly prepared or aged, respectively, tape rolls.
  • Example 1 was repeated with the exception that the precursor of the release coating composition included a mixture of Tego ® RC 708 and Tego ® RC 711 in a ratio of 70 parts/30 parts instead of 100 parts Tego ® RC 708. Comparative Example 2
  • Example 1 was repeated with the exception that the precursor of the release coating composition included 100 parts of Tego ® RC 726 instead of 100 parts of Tego ® RC 708.
  • Example 6 was repeated with the exception that the precursor of the release coating composition included a mixture of Tego ® RC 726 and the acrylate-modified MQ silicone resin contained in Tego ® RC 708 in a weight ratio of 60 parts/40 parts.
  • Example 1 was repeated with the exception that the precursor of the release coating composition included a mixture of Tego ® RC 902 (Th. Goldschmidt AG) and the same acrylate-modified MQ silicone resin contained in Tego ® RC 708 in a weight ratio of 70 parts/30 parts instead of
  • the coating weight of the precursor composition was 0.50 g/m 2 in Comparative Example 4 and reduced to 0.36 g/m 2 in

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)

Abstract

L'invention concerne un ruban auto-adhésif à déroulement silencieux comprenant un revêtement détachable renfermant le produit réactionnel de i) entre 15 et 35 % en poids de résines MQ de silicium contenant un ou plusieurs groupes fonctionnels de (méth)acrylate; ii) entre 50 et 85 % en poids d'organopolysiloxane à longue chaîne durcissable par rayonnement contenant au moins un groupe de (méth)acrylate; iii) moins de 25 % en poids d'organopolysiloxane à longue chaîne durcissable par rayonnement contenant au moins un groupe de (méth)acrylate; iv) une quantité efficace d'un photoamorceur. Les pourcentages en poids donnés pour le composant i), ii) et iii) se réfèrent respectivement au total des masses des composant i), ii) et iii) qui font 100 % en poids.
PCT/US1998/015233 1998-07-21 1998-07-21 Ruban auto-adhesif a deroulement silencieux WO2000005291A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2000561245A JP2002521513A (ja) 1998-07-21 1998-07-21 低騒音巻き戻し感圧接着テープ
BR9815954-2A BR9815954A (pt) 1998-07-21 1998-07-21 Fita adesiva sensìvel à pressão, uso da mesma, e, processo para utilizar um rolo da fita adesiva sensìvel à pressão.
AU85093/98A AU8509398A (en) 1998-07-21 1998-07-21 Low noise unwind pressure-sensitive adhesive tape
EP98935948A EP1097180A1 (fr) 1998-07-21 1998-07-21 Ruban auto-adhesif a deroulement silencieux
PCT/US1998/015233 WO2000005291A1 (fr) 1998-07-21 1998-07-21 Ruban auto-adhesif a deroulement silencieux

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1998/015233 WO2000005291A1 (fr) 1998-07-21 1998-07-21 Ruban auto-adhesif a deroulement silencieux

Publications (1)

Publication Number Publication Date
WO2000005291A1 true WO2000005291A1 (fr) 2000-02-03

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EP (1) EP1097180A1 (fr)
JP (1) JP2002521513A (fr)
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WO (1) WO2000005291A1 (fr)

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CN102897579A (zh) * 2012-10-31 2013-01-30 东莞市兴盛胶粘制品有限公司 纸芯内径为25.4mm的低噪音BOPP压敏胶粘带的生产方法
US20220002595A1 (en) * 2018-11-21 2022-01-06 Shin-Etsu Chemical Co., Ltd. Ultraviolet ray curable silicone adhesive composition and cured product thereof

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US20150111017A1 (en) * 2012-05-03 2015-04-23 3M Innovative Properties Company Packaging Tape
WO2014054701A1 (fr) * 2012-10-05 2014-04-10 東洋紡株式会社 Film de protection de surface auto-adhésif
KR20160135256A (ko) * 2014-03-19 2016-11-25 린텍 가부시키가이샤 박리제 조성물, 박리 필름, 박리 필름의 권취체 및 당해 권취체의 제조 방법
KR101768307B1 (ko) * 2015-04-29 2017-08-16 삼성에스디아이 주식회사 실리콘 점착제 조성물, 이로부터 형성된 실리콘 점착 필름 및 이를 포함하는 광학표시장치
KR20170045608A (ko) * 2015-10-19 2017-04-27 김대영 무소음 테이프 및 그의 제조방법
KR101775368B1 (ko) * 2016-04-18 2017-09-06 주식회사 제일에스엔씨 저소음 점착테이프 및 그 제조방법
KR101868033B1 (ko) * 2016-05-24 2018-06-15 조경국 코로나방전을 이용한 박리 시 소음방지형 접착테이프의 제조방법

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CN102897579A (zh) * 2012-10-31 2013-01-30 东莞市兴盛胶粘制品有限公司 纸芯内径为25.4mm的低噪音BOPP压敏胶粘带的生产方法
CN102897579B (zh) * 2012-10-31 2015-03-18 东莞市兴盛胶粘制品有限公司 纸芯内径为25.4mm的低噪音BOPP压敏胶粘带的生产方法
US20220002595A1 (en) * 2018-11-21 2022-01-06 Shin-Etsu Chemical Co., Ltd. Ultraviolet ray curable silicone adhesive composition and cured product thereof

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JP2002521513A (ja) 2002-07-16
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