US3695477A - Plastisols and gaskets - Google Patents

Plastisols and gaskets Download PDF

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Publication number
US3695477A
US3695477A US38491A US3695477DA US3695477A US 3695477 A US3695477 A US 3695477A US 38491 A US38491 A US 38491A US 3695477D A US3695477D A US 3695477DA US 3695477 A US3695477 A US 3695477A
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United States
Prior art keywords
plastisols
plastisol
parts
weight
block copolymer
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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.)
Expired - Lifetime
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US38491A
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English (en)
Inventor
Robert P Edmonston
John W Lefforge
George C Keller
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WR Grace and Co
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WR Grace and Co
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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
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08L27/06—Homopolymers or copolymers of vinyl chloride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
    • 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
    • C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09K2200/0635—Halogen-containing polymers, e.g. PVC
    • 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
    • C09K2200/0642—Copolymers containing at least three different monomers

Definitions

  • ABSTRACT Plastisols preferably of polyvinyl chloride, having a high yield value and low high shear viscosities are obtained by thickening conventional plastisol preparations with about 1 to 40 parts of certain block copolymers of the A-B-A type in which B is an elastomeric polymer core and A stands for a thermoplastic polymerized alkenyl aromatic compound.
  • resilient gaskets can be manufactured from these improved materials.
  • an air-tight pressure crown seal is applied on the orifice of the container, for instance a bottle, to retain the carbonation of the contents and to protect the beverage against contamination.
  • Crowns for such bottles are made of metal having uniform ductility, gage and even temper and are lined with a sealing gasket which may consist of cork, polyethylene, fluxed plastisols or other plastic materials. It is with fluxed plastisol linings or gaskets of this general type that the present invention is concerned.
  • plastisols comprise a dispersion of finely divided thermoplastic resin particles in a liquid nonvolatile plasticizer in which the resin is insoluble or only very slightly soluble at room temperature. At elevated temperatures, the resin becomes substantially completely solvated by the plasticizer, yielding a homogeneous solution which transforms itself into a rubbery thermoplastic mass upon cooling.
  • other ingredients may enter the plastisol compositions to accomplish conventional purposes.
  • the compositions may contain fillers, pigments, stabilizers, wetting agents and thickeners.
  • a gas may be dispersed in the plastisol or a gas-evolving agent, Le, a blowing agent, may be incorporated which will decompose at the fluxing temperature of the composition.
  • Plastisols are widely used in the manufacture of sealing gaskets for crown closures, where the gasket comprises an over-all liner coextensive with the inside surface of the closure panel.
  • a measured quantity of plastisol is deposited in an inverted closure shell and the closure is rotated at high speed to cause the deposit to spread over the inner surface of the closure panel.
  • the deposit is then heated at a temperature and for a period of time sufficient to completely flux the composition.
  • the lined crown closure thus obtained is placed over the orifice of the bottle and the skirt of the crown is crimped around the locking ring of the bottle to form a seal.
  • the operations and manipulations that the plastisols must undergo in the procedures just described and in other similar sealing applications require that the liquid compositions involved possess certain characteristic rheological properties.
  • the compositions must be fluid enough at high shear rates to permit easy disposition through a nozzle and rapid distribution over the inner surface of the closure when the spin lining technique is employed. Yet, they must possess a viscosity suffi ciently high so that the gasket material remain in position until it is solidified by heat treatment.
  • This type of property is conventionally imparted to plastisols by incorporating into them a small quantity of a finely divided material, generally of siliceous nature.
  • the block copolymers that-are added to plastisols according to the present invention are thermoplastic elastomers composed of polymerized alkenyl substituted aromatic segments attached to the ends of an elastomeric polymerized hydrocarbon chain core.
  • Usable hydrocarbon monomers for forming the core preferably contain four to eight carbon atoms. This includes butadiene, isoprene, pentadiene-l,3 and 2,3- dimethylbutadiene.
  • the elastome'ric core material may also consist of saturated ethylene-propylene copolymers.
  • the alkenyl aromatic hydrocarbon monomers used to form the rest of the block copolymer molecule are preferably of the monovinyl substituted type such as styrene, methylstyrene, vinyl toluene, vinyl naphthalene and the like. More than one monomer may be employed for each section of the block copolymer.
  • the structure of the block copolymers being described may be represented by the formula A-B-A in which B is the elastomeric core while A stands for the aromatic alkene polymer segments. While, obviously such copolymers may possess a gradation of properties ranging from those of relatively homogeneous polymerized aromatic vinyl compoundsto those of relatively homogeneous elastomers, the polymers of particular interest here possess a thermoplastic seg ment content of about 10 to 50 percent by weight, an average elastomeric core molecular weight of about 10,000 to 200,000, and an average thermoplastic segment molecular weight of 2,000 to 30,000.
  • the preferred copolymers within the class just described are styrene-butadiene block copolymers containing from about 25 to 30 percent by weight polymerized styrene and having an average overall molecular weight of between about 60,000 and 160,000.
  • the selected copolymer is dissolved in a conventional liquid plasticizer and the solution is incorporated into the plastisol by mixing. Between about 1 and 40 parts by weight of block copolymer per hundred parts of plastisol resin will yield the desired results.
  • the plasticizers that may be employed to dissolve the block copolymer as well as to form the plastisol may be dialkyl phthalates, such as dioctyl phthalate, butyl decyl phthalate and octyl decyl phthalate; alkyl phthalyl alkyl glycollates, such as butyl phthalyl butyl glycollate and methyl phthalyl ethyl glycollate; and dialkyl esters of alkane dicarboxylic acids, such as dioctyl and dibutyl sebacates, dioctyl azelate and diisobutyl adipate.
  • dialkyl phthalates such as dioctyl phthalate, butyl decyl phthalate and octyl decyl phthalate
  • alkyl phthalyl alkyl glycollates such as butyl phthalyl butyl glycollate and methyl phthalyl
  • Secondary plasticizers that may be incorporated in the plastisol include trialkyl and triaryl phosphates, acetyl trialkyl citrates, alkyl esters of high fatty acids, epoxy derivatives and polymeric polyester plasticizers, such as glycol sebacate polyesters. If desired, mixtures of plasticizers may be employed including one or more primary plasticizers and blends of primary and secondary plasticizers.
  • a block copolymer preflux is formed by heating with agitation at 250 to 280F, one part by weight of a block copolymer of styrene and butadiene containing 25 percent bound styrene and having an average overall molecular weight of about 120,000, with 4 parts dioctylphthalate.
  • a conventional polyvinyl chloride (PVC) plastisol is prepared from the following ingredients:
  • a wax-plasticizer blend is formed by melting the wax in a few parts of the plasticizer at a temperature of approximately 130F.
  • the hot wax blend is mixed with about half the plasticizer, the mixture stirred and allowed to cool to about 1 F.
  • the eicosane, the stabilizer, the azo compound and the resin are added with stirring.
  • the remaining plasticizer is also added and the resulting composition stirred until a homogeneous mixture results.
  • the preflux is then blended in to obtain a product having a 60 rpm viscosity of 14,000 centipoises and a 6 rpm viscosity of 45,000 cps as measured on a Brookfield viscosimeter (model LVF-SX) at 1 10F with a No. 3 spindle.
  • EXAMPLE 2 A plastisol is prepared as in Example 1 except that it contains 3 parts of fumed silica, a conventional thickener. The SBR block copolymer preflux is omitted.
  • the plastisol thus obtained has a 6 rpm viscosity of 60,000 cps and a 60 rpm viscosity of 20,000 cps.
  • Example 1 and 2 The plastisols of Example 1 and 2 were applied to bottle crowns and fluxed in the conventional manner. The crowns were then affixed to bottles filled with simulated soft drink pack and the packages obtained were subjected to an abuse test.
  • EXAMPLE 3 Another illustrative composition can be prepared in the conventional manner from the following ingredients:
  • a fluxed plastisol with greatly decreased compressive modulus and only moderately increased shear strength, thus particularly suited for sealing and capping without any decrease in blow-off pressure, is prepared by incorporating 25 parts per 100 parts resin by weight of a styrene-butadiene block copolymer such as Kraton*(*Registered trademark, Shell Chemical Co.) 1102 which has a Brookfield viscosity of about 1000 cp at room temperature for a 25 percent concentration by weight in toluene.
  • a 50 percent by weight solution of the block copolymer in the plasticizer is prepared by prolonged stirring and heating, for instance at 280F, and this solution is added to a plastisol which has otherwise been prepared in the conventional manner.
  • Parts by Weight Solutions or suspensions of the various ingredient in DOP are first prepared at the solids concentration indicated and the resulting mixtures are combined in the proportions indicated in the total column of the above table.
  • the block copolymer solution is added last to a thorough mixture of all the other components and it is mixed in until a uniform product is obtained.
  • the net amount of plasticizer used is tabulated in the next column and adds up to 425 parts by weight for a final ratio of 85 parts per 100 parts resin.
  • a similar preparation can be made without the 125 parts styrene-butadiene block copolymer.
  • a silica aerogel, 45 parts by weight is used instead; all other component quantities and ratios are maintained unchanged including the DOP to resin ratio.
  • the block copolymer-containing structures have been found to possess an average second blow-off pressure 17 psi higher than their silica-containing analogs over the range of 32 to 212F.
  • the closing force required for the block copolymer plastisol is only 50 to percent of that needed with the conventional silica preparations.
  • exposure of fluxed gaskets to 50 percent aqueous solution of ethyl alcohol at F results in a loss of only 8 percent of the plasticizer when the block copolymer is present while 18 percent of the plasticizer is extracted with silica present.
  • the use of block copolymers results in increased shear and tensile modulus while providing relatively lower durometer values.
  • the plastisol compositions that can benefit from the incorporation of block copolymers of the styrene-butadiene type as described in this invention are those of vinyl chloride homopolymers as well as copolymers containing up to 20 percent of vinyl acetate. Although such polymers are preferred, other acid-resistant thermoplastic resins may be used, including polyvinyl acetate, polyvinyl butyrate, polyvinyl alcohol, polyvinylidene chloride, and so on. These materials, as well as the other modifying components of the plastisols such as blowing agents, fillers, stabilizers, pigments and dispersing agents are well known to the art and are listed in numerous publications including, for example, U. S. Pat. No. 3,447,710. No need exists therefore for re-numerating all the possible elements that can be combined by the man skilled in the art to yield compositions that can be improved in the manner disclosed by the present invention.
  • a container closure comprising a flowed-in gasket consisting of a fluxed layer of a plastisol of a resin selected from the group consisting of homopolymers and copolymers of vinyl chloride containing up to 20 percent of vinyl acetate, containing, for each 100 parts by weight of the resin, from about 1 to 40 parts of a block copolymer having an A-B-A structure in which B represents an elastomeric core of polymerized diene units selected from the class consisting of conjugated diene hydrocarbon compounds having four to eight carbon atoms and elastomeric copolymers of ethylene with propylene, said core having an average molecular weight within the range of 10,000 to 200,000, and A represents a thermoplastic segment of a polymerized alkenyl aromatic compound of average molecular weight within the range of about 2,000 to 30,000, wherein the total polymerized alkenyl aromatic compound content constitutes from about 10 to 50 percent by weight of the block copolymermolecule.
  • the container closure of claim 1 wherein the plastisol contains about 5 to 25 parts by weight of a copolymer of styrene and butadiene having average over-all molecular weight of about 60,000 to 160,000 and a copolymerized styrene content within the range of 25 to 30 percent of the weight of the molecule.

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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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Sealing Material Composition (AREA)
US38491A 1970-05-18 1970-05-18 Plastisols and gaskets Expired - Lifetime US3695477A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US3849170A 1970-05-18 1970-05-18

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US (1) US3695477A (enExample)
AU (1) AU2897471A (enExample)
BE (1) BE767331A (enExample)
BR (1) BR7103002D0 (enExample)
CA (1) CA953842A (enExample)
DE (1) DE2124375A1 (enExample)
FR (1) FR2091755A5 (enExample)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3852096A (en) * 1972-02-25 1974-12-03 Exxon Research Engineering Co Process for fabricating an article from a multiphase copolymer composition
US3925280A (en) * 1972-02-25 1975-12-09 Exxon Research Engineering Co Fabrication multiphase plastics from liquid suspension
US4020966A (en) * 1975-03-28 1977-05-03 W. R. Grace & Co. Plastisol composition and container closure gasket made therefrom
US4042556A (en) * 1974-05-23 1977-08-16 Central Glass Co., Ltd. Process for the production of hard vinyl chloride foams
US4085186A (en) * 1975-12-05 1978-04-18 Cpl Corporation Process for producing flow-in closure sealing gaskets from hot melt compositions
US4096204A (en) * 1976-06-07 1978-06-20 Shell Oil Company Halogenated thermoplastic/block copolymer blend
US4143185A (en) * 1972-02-25 1979-03-06 Exxon Research & Engineering Co. Fabrication of coatings from thermoplastic ionomers
US4208315A (en) * 1979-02-01 1980-06-17 Shell Oil Company Footwear composition of a blend of ethylene-vinyl acetate copolymer, poly(vinyl chloride) and a block copolymer
US4226943A (en) * 1978-11-21 1980-10-07 Otsuka Kagaku Yakuhin Kabushiki Kaisha Foamable composition of vinyl chloride polymers and method of producing open cell sheet
US4228245A (en) * 1979-07-02 1980-10-14 Monsanto Company Foam rubber polyblend
US4278718A (en) * 1980-01-11 1981-07-14 W. R. Grace & Co. Sealing compositions for minimizing soluble iron migration
US4485192A (en) * 1982-10-12 1984-11-27 W. R. Grace & Co. Plastisol sealing gaskets puffed with hollow discrete spheres
US4968514A (en) * 1984-12-11 1990-11-06 Forbes Polytech, Inc. Beer bottle with fully reacted thermoplastic polyurethane crown capliner
US5137164A (en) * 1987-03-05 1992-08-11 Owens-Illinois Closure Inc. Closure assembly using epoxidized natural oil in a low fusing plastisol
US5187203A (en) * 1991-10-23 1993-02-16 Armstrong World Industries, Inc. Non-corrosive elastomeric foam for insulating copper tubes
WO1996039338A1 (en) * 1995-06-06 1996-12-12 Multisorb Technologies, Inc. An oxygen absorbing container cap liner
US5776993A (en) * 1996-03-12 1998-07-07 Korea Institute Of Footwear & Leather Technology Thermoplastic PVC foam composition
US5839593A (en) * 1995-06-06 1998-11-24 Multiform Desiccants, Inc. Oxygen absorbing container cap liner
US5900455A (en) * 1992-06-05 1999-05-04 Shell Oil Company Elastosols, process for the preparation thereof, process for the use of such elastosols and products derived from them

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58206752A (ja) * 1982-05-28 1983-12-02 テルモ株式会社 医療用器具の接合構造

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3005796A (en) * 1958-05-05 1961-10-24 Dow Chemical Co Blend of polyvinyl chloride and butadiene-styrene copolymers and method of making same
US3429951A (en) * 1965-09-07 1969-02-25 Phillips Petroleum Co Reaction of peroxides with blends of polystyrene and rubbery block copolymer
US3441530A (en) * 1965-01-27 1969-04-29 Shell Oil Co Block copolymer powders
US3459831A (en) * 1965-09-24 1969-08-05 Shell Oil Co Block copolymer-polyethylene films

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3005796A (en) * 1958-05-05 1961-10-24 Dow Chemical Co Blend of polyvinyl chloride and butadiene-styrene copolymers and method of making same
US3441530A (en) * 1965-01-27 1969-04-29 Shell Oil Co Block copolymer powders
US3429951A (en) * 1965-09-07 1969-02-25 Phillips Petroleum Co Reaction of peroxides with blends of polystyrene and rubbery block copolymer
US3459831A (en) * 1965-09-24 1969-08-05 Shell Oil Co Block copolymer-polyethylene films

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3852096A (en) * 1972-02-25 1974-12-03 Exxon Research Engineering Co Process for fabricating an article from a multiphase copolymer composition
US3925280A (en) * 1972-02-25 1975-12-09 Exxon Research Engineering Co Fabrication multiphase plastics from liquid suspension
US4143185A (en) * 1972-02-25 1979-03-06 Exxon Research & Engineering Co. Fabrication of coatings from thermoplastic ionomers
US4042556A (en) * 1974-05-23 1977-08-16 Central Glass Co., Ltd. Process for the production of hard vinyl chloride foams
US4020966A (en) * 1975-03-28 1977-05-03 W. R. Grace & Co. Plastisol composition and container closure gasket made therefrom
US4085186A (en) * 1975-12-05 1978-04-18 Cpl Corporation Process for producing flow-in closure sealing gaskets from hot melt compositions
US4096204A (en) * 1976-06-07 1978-06-20 Shell Oil Company Halogenated thermoplastic/block copolymer blend
US4226943A (en) * 1978-11-21 1980-10-07 Otsuka Kagaku Yakuhin Kabushiki Kaisha Foamable composition of vinyl chloride polymers and method of producing open cell sheet
US4208315A (en) * 1979-02-01 1980-06-17 Shell Oil Company Footwear composition of a blend of ethylene-vinyl acetate copolymer, poly(vinyl chloride) and a block copolymer
US4228245A (en) * 1979-07-02 1980-10-14 Monsanto Company Foam rubber polyblend
US4278718A (en) * 1980-01-11 1981-07-14 W. R. Grace & Co. Sealing compositions for minimizing soluble iron migration
US4485192A (en) * 1982-10-12 1984-11-27 W. R. Grace & Co. Plastisol sealing gaskets puffed with hollow discrete spheres
US4968514A (en) * 1984-12-11 1990-11-06 Forbes Polytech, Inc. Beer bottle with fully reacted thermoplastic polyurethane crown capliner
US5137164A (en) * 1987-03-05 1992-08-11 Owens-Illinois Closure Inc. Closure assembly using epoxidized natural oil in a low fusing plastisol
US5187203A (en) * 1991-10-23 1993-02-16 Armstrong World Industries, Inc. Non-corrosive elastomeric foam for insulating copper tubes
US5900455A (en) * 1992-06-05 1999-05-04 Shell Oil Company Elastosols, process for the preparation thereof, process for the use of such elastosols and products derived from them
WO1996039338A1 (en) * 1995-06-06 1996-12-12 Multisorb Technologies, Inc. An oxygen absorbing container cap liner
US5839593A (en) * 1995-06-06 1998-11-24 Multiform Desiccants, Inc. Oxygen absorbing container cap liner
AU718600B2 (en) * 1995-06-06 2000-04-20 Multisorb Technologies, Inc. An oxygen absorbing container cap liner
US5776993A (en) * 1996-03-12 1998-07-07 Korea Institute Of Footwear & Leather Technology Thermoplastic PVC foam composition

Also Published As

Publication number Publication date
CA953842A (en) 1974-08-27
DE2124375A1 (de) 1971-12-02
BR7103002D0 (pt) 1973-04-05
AU2897471A (en) 1972-11-23
BE767331A (fr) 1971-11-18
FR2091755A5 (enExample) 1972-01-14

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