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WO1982002721A1 - Compositions d'etancheite - Google Patents

Compositions d'etancheite Download PDF

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Publication number
WO1982002721A1
WO1982002721A1 PCT/GB1982/000036 GB8200036W WO8202721A1 WO 1982002721 A1 WO1982002721 A1 WO 1982002721A1 GB 8200036 W GB8200036 W GB 8200036W WO 8202721 A1 WO8202721 A1 WO 8202721A1
Authority
WO
WIPO (PCT)
Prior art keywords
rubbery polymer
composition according
filler
sealing
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB1982/000036
Other languages
English (en)
Inventor
R Grace & Co W
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.)
WR Grace and Co
Original Assignee
WR Grace and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by WR Grace and Co filed Critical WR Grace and Co
Publication of WO1982002721A1 publication Critical patent/WO1982002721A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • 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
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/02—Inorganic compounds
    • C09K2200/0204—Elements
    • C09K2200/0213—Metals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0607—Rubber or rubber derivatives

Definitions

  • This invention relates to sealing compositions intended for sealing container closures such as top or bottom end closures of cans or replaceable or non-replaceable caps for jars or bottles.
  • the compositions can also be used for other sealing purposes but, for clarity, since they are formulated to meet the particular requirements of can and other container closure seals the invention is described solely in terms of compositions for sealing container closures.
  • Traditional container end sealing compositions have comprised a liquid medium in which has been dispersed or dissolved rubber or other polymeric material and which includes also fillers, tackifying resin and other additives.
  • the liquid medium may be aqueous, for instance as in US Patent Specification No. 5,409,567 or British Patent Specification No.
  • liquid medium may be organic, for instance as in British Patent Specification No. 1,340,730.
  • fillers have been proposed for use in the compositions, for instance as is shown by these patent specifications, but only a few have proved to be satisfactory in use.
  • Typical fillers that have been found satisfactory include kaolin, talc, zinc oxide and calcium carbonate. Generally the amount of filler must not be too high or else the sealing properties are impaired.
  • the liquid composition is applied to one at least of the mating surfaces of the closure and the sealing race 01 the container, generally to the closure, and is then dried on the surface.
  • the closure is pressed onto the sealing face of the container so as to grip the container firmly and the composition provides a seal between the container and the closure.
  • composition should have appropriate rheological and other physical properties.
  • the composition when applied to can ends it should flow adequately during sealing so as to distribute itself over the mating surfaces, but preferably it does not flow to such an extent that significant extrusion of the composition occurs along the walls of the can.
  • the seal provided by the composition should prevent ingress of bacteria. Generally it should also prevent loss of liquid, vacuum or gas.
  • the filler is such that, compared to use of fillers commonly used at present, either the seal is improved or the amounts of either the rubber or other polymeric material or the tackifying resin, or both, can be reduced without reducing the sealing properties. It has also been our object to provide methods of sealing containers using such compositions, and to provide sealed containers.
  • a sealed container according to the invention has a closure sealed to it by a seal that includes a gasket formed of a rubbery polymer in which is dispersed filler including crush resistant metal particles having a particle size of less than 200 microns.
  • a novel composition according to the invention comprises a rubbery polymer and filler that is dispersed throughout the composition and that includes the particles and generally also tackifying resin.
  • the composition may be a meltable solid but preferably comprises also a liquid medium in which the polymer is dissolved or dispersed.
  • the sealed container may be fully sealed, for instance being a jar or a one piece can or a can sealed at both ends, or it may be a can. that has a closure sealed to it one end but which is open at the other.
  • a sealed container can be formed from a container and a container closure in conventional manner.
  • the sealing face of the closure is lined with a liquid composition comprising rubbery polymer and a dispersion of the filler, the composition is solidified (generally by drying) to form a gasket, and the sealing face of the closure is compressed around the end of the container thereby sealing the closure to the sealing face with the gasket within the seal.
  • the container is a bottle this gasket is trapped between the sealing face of the rim of the bottle and the overlying closure.
  • the container is a can in which event the gasket is trapped in the double seam formed in conventional manner by compressing the outer periphery of the container closure around an outwardly extending flange of the side wall and then pressing the flange and the closure periphery against the side wall of the container generally in a single operation.
  • the particles must be crush resistant, that is to say they must have sufficient strength to resist any risk of crushing during the sealing use to which the composition is to be subjected. Thus in a can end sealing composition the beads must have sufficient strength that they will not crush in the seal. In order that they are crush resistant the particles must be formed of a hard metal. Thus a soft metal such as tin is unsatisfactory but hard metals such as stainless steel, nickel alloy or chromium are satisfactory.
  • the particles may have a rough surface or a smooth surface and may have a regular shape or an irregular shape. Preferably however any roughness or irregularity is not too extensive since otherwise this may increase the adhesion of the rubbery polymer to the surface of the particles to such an extent to deminish the advantages that are otherwise obtained. Preferably the particles are substantially smooth.
  • the particle size range of the beads is generally between 1 and 100 microns, preferably 10 to 75 microns.
  • the maximum particle size most preferably is not more than 60 microns.
  • the average particle size is generally from 5 to 100 microns, most preferably 10 to 50 microns, with best results generally being achieved with an average size of 20 to 50 microns.
  • the metal particles may have been given a surface coating of a variety of materials provided the surface coating does not interact with other components in the composition in such a way as to reduce significantly the sealing properties of the composition. Throughout this specification amounts of components of the composition, including amounts of metal particles and other fillers, are expressed as amounts by volume based on the volume of rubbery polymer, unless otherwise specified. For instance 101 particles means 10 volumes particles per 100 volumes rubbery polymer.
  • the amount of the particles in the composition should be at least 1%, since lower amounts tend to give inadequate improvement. Generally the amount is below 1501, and normally below 100%, since greater amounts tend not to give significant further improvement. Generally the amount is at least 31, and normally, at least 5%. Preferably the amount is at least 10%. Generally the amount is up to 50%. Typically the amount may be from 5 to 100%, most preferably 10 to 50%.
  • the filler may consist substantially only of the particles, with the result that the composition may contain no significant amounts of other fillers, although it may include fillers that are present primarily for their pigmentary purposes, for instance titanium dioxide which may be present in amounts of up to 10 or 15%. Good results are also obtained when the filler does include other particulate inorganic material and this is generally preferred.
  • the material other than the particles may be present in an amount of 0 to 150 (based on the volume of rubbery polymer), generally 10 to 100% and preferably 15 to 100%.
  • the composition includes 0.05 to 2 parts, most preferably 0.1 to 1 part, by volume particles per part by volume other inorganic particulate filler.
  • the total volume of filler, including the particles can be similar to that conventionally used in commercial sealing compositions, for instance 10 to 45%, a particular advantage of the invention is that larger amounts of total filler may be used while still obtaining satisfactory sealing properties.
  • the total amount of filler, including the particles is usually at least 20% (by volume based on the volume of rubbery polymer) and can be up to 175%, for instance 50 to 125%. Titanium dioxide or other pigmentary filler
  • fillers that may be used in the invention generally have a particle size of from 1 to 50 microns.
  • the filler should be substantially non-abrasive, so that it does not cause wear to the machinery by which the composition is mixed and lined onto the can or other end.
  • the preferred other filler is kaolin or china clay or zinc oxide but other fillers include colloidal silica and other silicic fillers, synthetic silicate, calcium carbonate or sulphate, aluminium hydroxide, talc, dolomite, barium sulphate, or magnesium oxide or carbonate or silicate. Such fillers may have been surface treated, for instance in conventional manner.
  • some other colouring material for instance a soluble dye, may be included.
  • the composition is formed from a rubbery polymer, that is to say a polymer that, when dried, forms a gasket that is sufficiently flexible and resistant to be capable of serving as a seal. It should have the conventional properties of rubbery polymers, i.e. it should be capable of being subjected to substantial reversible deformation. Rubbery polymers suitable for forming seals are well known. Generally the Mooney viscosity (ML, ) of the rubbery polymer is from 20 to 200, preferably 40 to 160.
  • the rubbery polymer may be a natural polymer, for instance natural rubber, or may be a synthetic polymer Suitable synthetic rubbery polymers include butyl rubber, polychloroprene, butadiene acrylonitrile copolymers, ethylene propylene copolymers, ethylene-propylene-diene terpolymers, styrene isoprene block copolymers, polybutadiene, styrene acrylic copolymers, polyvinylidene chloride, polyvinylidene chloride copolymers, plasticised polyvinyl chloride, polyvinyl chloride copolymers, plasticised polyvinyl propionate or acetate, polyvinyl propionate or acetate copolymers, polyacrylic acid copolymers, polymethylacrylic acid copolymers, acrylic ester copolymers, methacrylic ester copolymers, plasticised polystyrene, vinyl acetate copolymers with for instance eth
  • Compositions based on vulcanisable polymers may include vulcanising agent.
  • the rubbery polymer will be chosen having regard to, for instance, the type of composition that is being used for forming the seal.
  • the preferred polymers are styrene butadiene rubbers having a styrene content of 15 to 60% preferably 18 to 45% by weight.
  • They may have been made by any convenient polymerisation method, and thus may have been made by hot or cold polymerisation techniques.
  • Tackifier resins are generally included in can sealing compositions and they may be included in the compositions used in the invention. However because of the good sealing properties obtained by the use of novel filler satisfactory results can often be obtained without a tackifier resin in the invention. Instead of using a tackifier resin a liquid plasticiser, such as white oil or other hydrocarbon oil, that softens the polymer may be used in amount of for instance 1 to 60%, preferably 5 to 40%.
  • a liquid plasticiser such as white oil or other hydrocarbon oil
  • tackifier resin is included.
  • Suitable materials are well known and are generally selected from synthetic hydrocarbon or petroleum resins, polyterpene, resins, phenolic resin modified with natural resins such as rosin or terpene, xylene formaldehyde resin and modified products thereof, and esterified rosins or other rosin type resins such as rosin, hydrogenated rosin, or hardened rosin.
  • the amount of tackifier is generally at least 10% (by volume of rubbery polymer) but less than 250% and preferably less than 200%. Generally the amount is at least 15%.
  • the compositions may include minor amounts, e.g.
  • viscosity increasing agents for instance ammonium alginate, bentonite or gum karaya or high molecular weight polyacrylic acid
  • bactericides for instance ammonium alginate, bentonite or gum karaya or high molecular weight polyacrylic acid
  • corrosion inhibitors for instance ammonium alginate, bentonite or gum karaya or high molecular weight polyacrylic acid
  • surfactants for instance phenolic or amino anti-oxidants
  • anti-oxidants for instance phenolic or amino anti-oxidants
  • pH adjusters for instance ammonia, primary amine, sodium hydroxide or sodium carbonate
  • the composition preferably is liquid at room temperature and thus preferably includes a liquid medium that serves as a carrier for the rubbery polymer and the filler.
  • the amount of the liquid medium will be chosen having regard to the maximum total solids concentration obtainable in the final composition consistent with solubility or dispersibility of the polymer in the liquid medium, ease in preparing the composition, storage stability of the composition, and application of the composition to the can end using high speed automatic lining equipment.
  • the amount of liquid medium is such as to yield a composition having a solids content of from 20% to 85% by weight.
  • the liquid medium is aqueous.
  • the aqueous composition will generally contain at least one stabiliser for stabilising the dispersion, This stabiliser may be selected from any of the materials conventionally used for stabilising aqueous sealing compositions based on filler and rubbery polymer.
  • Such stabilisers include styrene maleic anhydride or other styrene copolymers, methyl cellulose, polyacrylamide, ethoxylated condensates, polyvinyl pyrrolidone ammonium oleate, and casein.
  • Such stabilisers may be used in admixture, for instance with other materials.
  • the aqueous composition is preferably a latex obtained by dispersing the specified filler and tackifier (if present) into a latex of the chosen rubbery polymer, for instance as formed by emulsion polymerisation.
  • the composition may be made simply by mixing into the chosen latex (optionally after dilution) the tackifying resin, the selected filler or fillers, and any other additives, all in conventional manner.
  • the total solids content of the composition is generally from 20 to 85% by weight, preferably 30 to 80%.
  • the aqueous composition may be a dispersion obtained by dispersing solid rubbery polymer and filler into the aqueous medium.
  • the aqueous dispersion may be made by milling the solid rubber with filler and other optional additives, including also generally any tackifying resin, using an internal mixer, for instance a Banbury mixer, so as to form a rubber stock. This rubber stock is then dispersed in water in conventional manner, for instance using a
  • the Z-blade type of mixer may be added to the dispersion to alter its consistency.
  • additional components for instance thickening agent and more water, may be added to the dispersion to alter its consistency.
  • some may be added to the dispersion.
  • the rubber may be milled with some of the additives and then dispersed in water and other major additives introduced at this stage.
  • the novel filler of the invention may be added to the aqueous dispersion obtained by dispersing solid rubber and optionally some of the filler.
  • compositions of the invention can be organic, in which the liquid medium comprises organic solvent in which some or all of the rubbery polymer will dissolve, any remaining polymer going into dispersion.
  • Suitable organic liquids which may be employed in preparing organic compositions include aliphatic and aromatic hydrocarbons, for example 3-methylheptane, hexane, heptane, xylene and toluene; chlorinated hydrocarbons, such as dichloropentane; ketones; ethers, ether-alcohols and mixtures of these and other volatile organic liquids which together form media as known in the art for the selected elastomers.
  • the organic compositions are generally made by blending the solid rubber with filler and optional additives such as anti-oxidants in an internal mixer, for instance a Banbury mixer.
  • the solid rubber stock thus obtained is comminuted and dissolved in the chosen solvent or solvent mixture in conventional manner. If tackifying resin is to be introduced it may be added to the solvent or it may be blended into the solid rubber stock.
  • the composition may be an organosol of the rubbery polymer, filler, plasticiser, organic solvent and other optional additives.
  • the composition may be a melt consisting of the rubbery polymer and filler, and other optional additives.
  • the novel filler of the invention, and optionally other filler may be mixed into the polymer while it is soft and the mass then fully melted before application to the closure.
  • an equivalent volume of other filler such as kaolin
  • Metal particles also have the advantage that they can have inert surface characteristics and so can avoid some of the handling and other difficulties that may be encountered with other fillers. For instance fillers such as calcium carbonate can lead to a risk of coagulation of a polymer latex into which such a filler is incorporated. Accordingly when such fillers are used it is necessary to take particular precautions to prevent coagulation of any latex or dispersion that is present.
  • the most consistently satisfactory sealing properties and the greatest tendency for a significant improvement in sealing properties is obtainable in the invention when the metal particles are included in aqueous compositions, and especially in latex compositions, and so these are preferred.
  • the composition is lined into can closures (often termed can ends) and dried in conventional manner, the amount of the composition being such as to give the dry film volume generally recommended for the particular size.
  • Cans having a soldered side seam are then filled with a hot liquid nutrient, typically at a temperature of 97°C, leaving a small headspace.
  • the test closures are double seamed onto these filled cans whilst simultaneously injecting steam into the headspace.
  • the closed cans are then sterilised, typically at 121oC for 50 minutes, and after sterilisation are immediately cooled in water containing gas-producing, non-pathogenic micro-organisms capable of growth in the aforementioned nutrient.
  • the cans After cooling and whilst still wet with the cooling water, the cans are subjected to a controlled deformation at the junction of the side seam and the double seam of the test closure. After incubation for six days at an elevated temperature optimum for the growth of the micro-organisms, followed by one day at ambient temperature, the cans are examined visually and the number of swollen cans recorded. The retained vacuum in the remaining cans is measured. Cans having a low retained vacuum and the swollen cans are considered to have reached this condition through failure of the seal in the test closure. The swollen and low vacuum cans are termed failures and the "biological seal" value is the failure rate expressed as the number of such cans per thousand tested. Because of the procedures used the number of failed cans per thousand in this biological seal test is of course very much greater than that which would occur with commercially packed cans sealed with these compositions.
  • the composition is lined into can closures and dried, in conventional manner, the amount of the composition being such as to give a dry film volume approximately 20% greater than that generally recommended with the particular closure size.
  • Cans are filled with water at typically 70oC to leave no headspace and test closures are double seamed onto these filled cans.
  • the closed cans are then sterilised typically at 130°C for one hour and allowed to cool to room temperature before examination.
  • the number of protrusions of compound from the double seam along the outside wall of the can body at the test closure is counted, typically on a sample of 10 cans for each composition. Large protrusions are counted as appropriate multiples of the typical, more commonly occurring, small protrusions.
  • the average number of protrusions per can is recorded as the value for "extrusion". This value should be as low as possible, preferably below 10 under the conditions of the test. However, because of the extreme conditions of the test, greater values than this are commercially tolerable.
  • each composition is made by mixing together a latex of a rubbery polymer and containing minor amounts of conventional additives known to those skilled in the art, stabiliser, filler, titanium dioxide pigment, and tackifier resin.
  • the composition is lined onto the can closure, dried, and tested in the described manner.
  • the amount of tackifier resin is 22%, the amount of stabiliser is 4.2% and the amount of titanium dioxide is 3.2%, all based on the volume of rubbery polymer in the latex.
  • the amount of filler is given in the examples by volume based on the rubbery polymer. When the filler is kaolin the total solids content of the composition is about 60% by volume.
  • the filler consists of metal particles (if present) and the stated inorganic particulate material (if present) which generally has a particle size of 1 to 50 microns although titanium dioxide may have a particle size of down to 0.1 microns.
  • the latex is a styrene butadiene latex having a solids content of 66 to 69% by weight and containing 31 to 36% bound styrene and which has been polymerised cold (at 5oC) using fatty acid soaps.
  • the polymer in the latex has a Mooney value (as defined above) of 100 to 130.
  • Mooney value as defined above
  • the tackifier resin is a polymer of mixed
  • the stabiliser is a styrene-maleic anhydride copolymer. Similar results are obtainable with other tackifiers and stabilisers.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Sealing Material Composition (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Des particules metalliques sont comprises en tant que partie ou en tant que totalite de l'agent de remplissage dans une composition d'etancheite servant au montage etanches des extremites d'un recipient et cette composition comprend un polymere caoutchouteux tel qu'un copolymere de styrene butadiene, et facultativement aussi une resine de collage.
PCT/GB1982/000036 1981-02-14 1982-02-12 Compositions d'etancheite Ceased WO1982002721A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8104684 1981-02-14
GB8104684810214 1981-02-14

Publications (1)

Publication Number Publication Date
WO1982002721A1 true WO1982002721A1 (fr) 1982-08-19

Family

ID=10519719

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1982/000036 Ceased WO1982002721A1 (fr) 1981-02-14 1982-02-12 Compositions d'etancheite

Country Status (5)

Country Link
EP (1) EP0072810A1 (fr)
JP (1) JPS57190068A (fr)
CA (1) CA1179799A (fr)
GB (1) GB2105360B (fr)
WO (1) WO1982002721A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004003577A1 (de) 2004-01-23 2005-09-15 Volkswagen Ag Leuchtenanordnung für ein Fahrzeug
WO2013096360A1 (fr) 2011-12-20 2013-06-27 W. R. Grace & Co.-Conn. Composition de scellement pour récipient
US20160185936A1 (en) * 2012-12-20 2016-06-30 W.R.Grace & Co.- Conn. Container Sealant Composition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59215379A (ja) * 1983-05-23 1984-12-05 Nippon Pillar Packing Co Ltd ガスケツト

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2024359A1 (fr) * 1968-11-27 1970-08-28 British Petroleum Co
US3649438A (en) * 1967-10-03 1972-03-14 Polymer Corp Non-curing thermosensitive sealant tape
DE2461875A1 (de) * 1973-12-29 1975-07-03 Nitto Electric Ind Co Verfahren zum ausfuellen von vertiefungen in oberflaechen
FR2343795A1 (fr) * 1976-03-12 1977-10-07 Southland Corp Composition pour le scellement de fermetures d'extremites de boites metalliques et procede pour la fermeture etanche de boites metalliques
EP0010230A1 (fr) * 1978-10-20 1980-04-30 Klaus Prof. Dr. Heckmann Composition de caoutchouc ayant une résistance améliorée au vieillissement et procédé pour sa préparation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3649438A (en) * 1967-10-03 1972-03-14 Polymer Corp Non-curing thermosensitive sealant tape
FR2024359A1 (fr) * 1968-11-27 1970-08-28 British Petroleum Co
DE2461875A1 (de) * 1973-12-29 1975-07-03 Nitto Electric Ind Co Verfahren zum ausfuellen von vertiefungen in oberflaechen
FR2343795A1 (fr) * 1976-03-12 1977-10-07 Southland Corp Composition pour le scellement de fermetures d'extremites de boites metalliques et procede pour la fermeture etanche de boites metalliques
EP0010230A1 (fr) * 1978-10-20 1980-04-30 Klaus Prof. Dr. Heckmann Composition de caoutchouc ayant une résistance améliorée au vieillissement et procédé pour sa préparation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004003577A1 (de) 2004-01-23 2005-09-15 Volkswagen Ag Leuchtenanordnung für ein Fahrzeug
WO2013096360A1 (fr) 2011-12-20 2013-06-27 W. R. Grace & Co.-Conn. Composition de scellement pour récipient
US20150027087A1 (en) * 2011-12-20 2015-01-29 Qi Sun Container Sealant Composition
US20160185936A1 (en) * 2012-12-20 2016-06-30 W.R.Grace & Co.- Conn. Container Sealant Composition
US11421097B2 (en) 2012-12-20 2022-08-23 Henkel Ag & Co. Kgaa Container sealant composition

Also Published As

Publication number Publication date
EP0072810A1 (fr) 1983-03-02
GB2105360A (en) 1983-03-23
CA1179799A (fr) 1984-12-18
GB2105360B (en) 1985-01-30
JPS57190068A (en) 1982-11-22

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