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US20030181584A1 - Elastomeric articles prepared from controlled distribution block copolymers - Google Patents

Elastomeric articles prepared from controlled distribution block copolymers Download PDF

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Publication number
US20030181584A1
US20030181584A1 US10/209,285 US20928502A US2003181584A1 US 20030181584 A1 US20030181584 A1 US 20030181584A1 US 20928502 A US20928502 A US 20928502A US 2003181584 A1 US2003181584 A1 US 2003181584A1
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United States
Prior art keywords
block
weight
article according
elastomeric article
polymer
Prior art date
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Abandoned
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US10/209,285
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English (en)
Inventor
Dale Handlin
Carl Willis
Margaret Clawson
Hendrik Groot
Keith Eiden
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Kraton Polymers US LLC
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Kraton Polymers US LLC
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 Kraton Polymers US LLC filed Critical Kraton Polymers US LLC
Priority to US10/209,285 priority Critical patent/US20030181584A1/en
Priority to US10/359,907 priority patent/US7267855B2/en
Priority to US10/359,953 priority patent/US7847022B2/en
Priority to EP20030707247 priority patent/EP1474459B1/fr
Priority to DE60330119T priority patent/DE60330119D1/de
Priority to CN038074826A priority patent/CN1643015B/zh
Priority to EP20030737512 priority patent/EP1483328B1/fr
Priority to AU2003208667A priority patent/AU2003208667A1/en
Priority to CN038074605A priority patent/CN1643058B/zh
Priority to DE2003616262 priority patent/DE60316262T2/de
Priority to TW92102528A priority patent/TWI256969B/zh
Priority to EP20030707250 priority patent/EP1474495B1/fr
Priority to DE2003606493 priority patent/DE60306493T2/de
Priority to PCT/NL2003/000098 priority patent/WO2003066769A1/fr
Priority to AT03707250T priority patent/ATE331775T1/de
Priority to TW92102541A priority patent/TWI300781B/zh
Priority to AT03737512T priority patent/ATE373045T1/de
Priority to CNB038074478A priority patent/CN1311044C/zh
Priority to AU2003210069A priority patent/AU2003210069A1/en
Priority to PCT/NL2003/000094 priority patent/WO2003066697A1/fr
Priority to AU2003208664A priority patent/AU2003208664A1/en
Priority to TW92102586A priority patent/TWI300791B/zh
Priority to PCT/NL2003/000096 priority patent/WO2003066731A1/fr
Publication of US20030181584A1 publication Critical patent/US20030181584A1/en
Assigned to UBS AG, STAMFORD BRANCH reassignment UBS AG, STAMFORD BRANCH SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KRATON POLYMERS U.S. LLC
Abandoned legal-status Critical Current

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    • 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
    • C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J153/02—Vinyl aromatic monomers and conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F287/00—Macromolecular compounds obtained by polymerising monomers on to block polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
    • C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
    • C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • 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
    • 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
    • C08L53/025—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 modified
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
    • 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
    • C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D153/02—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
    • 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
    • C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D153/02—Vinyl aromatic monomers and conjugated dienes
    • C09D153/025—Vinyl aromatic monomers and conjugated dienes modified
    • 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
    • C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J153/02—Vinyl aromatic monomers and conjugated dienes
    • C09J153/025—Vinyl aromatic monomers and conjugated dienes modified
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C08L23/12—Polypropene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—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 an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/02—Homopolymers or copolymers of hydrocarbons
    • C08L25/04—Homopolymers or copolymers of styrene
    • C08L25/06—Polystyrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/24—Graft or block copolymers according to groups C08L51/00, C08L53/00 or C08L55/02; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/249921—Web or sheet containing structurally defined element or component
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31931—Polyene monomer-containing

Definitions

  • This invention relates to elastomeric articles prepared from novel anionic block copolymers of mono alkenyl arenes and conjugated dienes, and to blends of such block copolymers with other polymers.
  • the invention also relates to formed articles and methods for forming articles from such novel block copolymers.
  • a novel composition comprising at least one hydrogenated block copolymer having a controlled distribution block of a monoalkenyl arene and conjugated diene, and optionally including another polymer, has superior properties for many applications.
  • these compositions can be used in various forming processes, and that they also have a number of advantages in processing.
  • the broad aspect of the present invention is an elastomeric article comprising at least one hydrogenated block copolymer and, optionally, at least one other polymer selected from the group consisting of olefin polymers, styrene polymers, tackifying resins and engineering thermoplastic resins, wherein said hydrogenated block copolymer has the general configuration: A-B, A-B-A, or (A-B) n X; where n is an integer from 2 to about 30, and X is coupling agent residue and wherein (a.) prior to hydrogenation each A block is a mono alkenyl arene homopolymer block and each B block is a controlled distribution copolymer block of at least one conjugated diene and at least one mono alkenyl arene; (b.) subsequent to hydrogenation about 0-10% of the arene double bonds have been reduced, and at least about 90% of the conjugated diene double bonds have been reduced; (c.) each A block having an average
  • the elastomeric article can be formed in a wide variety of processes, including injection molding, compression molding, over molding, dipping, extrusion, roto molding, slush molding, fiber spinning, blow molding, polymer modification, cast film making, blown film making and foaming.
  • the hydrogenated controlled distribution polymer of the present invention may be functionalized in a variety of ways, including reaction with maleic acid or anhydride.
  • Such functionalized polymers have additional polarity that makes them particularly useful where adhesion to other polar polymers is important, such as in over molding applications.
  • the elastomeric articles of the present invention have a number of surprising properties. These properties include, for example, the unusual stress-strain response, which shows that a composition of the present invention exhibits a stiffer rubbery response to strain, therefore requiring more stress to extend the same length. This is an extremely useful property that allows the use of less material to achieve the same force in a given product. Elastic properties are also modified, exhibiting increasing modulus with increasing elongation, and there is a reduced occurrence of the rubbery plateau region where large increases in elongation are required to procure an increase in stress. Another surprising property is reduced coefficient of friction while retaining elastomeric properties. This is important for applications where a soft material is desired without a high friction surface. Still another surprising property is increased tear strength.
  • the controlled distribution copolymers of the present invention offer additional advantages in their ability to be easily processed using equipment generally designed for processing thermoplastic polystyrene, which is one of the most widely known and used alkenyl arene polymers.
  • Melt processing can be accomplished via extrusion or injection molding using either single screw or twin screw techniques that are common to the thermoplastics industry. Solution or spin casting techniques can also be used as appropriate.
  • a particularly interesting application is in over molding where a composition containing the controlled distribution block copolymer and optionally other thermoplastic polymers and process aides are injection molded onto a substrate of a more rigid polymer to impart a softer feel or different frictional characteristics.
  • the polymers of the present invention provide improved adhesion to polar polymers. Adhesion to very polar materials such as polyamides or polyurethanes may be further improved by functionalizing the polymer of the present invention, for example with maleic anhydride.
  • the elastomeric article can be processed into the form of a film, sheet, multi layer laminate, coating, band, strip, profile, molding, foam, tape, fabric, thread, filament, ribbon, fiber, plurality of fibers, or fibrous web.
  • thermoplastic films which retain the processability of styrenic block copolymers but exhibit a higher “elastic power” similar to spandex polyurethanes.
  • the controlled distribution copolymers of the present invention can meet these performance expectations.
  • the resultant films show significant improvements in puncture resistance and strength, and reduced viscosity, when compared with common styrene/ethylene-butylene block copolymers.
  • the same controlled distribution styrene/butadiene (25/75 wt/wt) copolymer can also be formulated in a film compound with oil and polystyrene, wherein it exhibits higher strength and improved energy recovery and transparency in comparison with a control formulation based on a styrene/ethylene-butylene/styrene block copolymer.
  • Molding applications formulated using oil and polypropylene have a reduced viscosity and coefficient of friction, and may be used in applications such as cap seals. It should also be possible to produce such cap seals without using undesirable slip agents.
  • the copolymers of the present invention can be compounded with other components not adversely affecting the copolymer properties.
  • Exemplary materials that could be used as additional components would include, without limitation, pigments, antioxidants, stabilizers, surfactants, waxes, and flow promoters.
  • the polymers of the present invention are useful in a wide variety of applications including, for example, molded and extruded goods such as toys, grips, handles, shoe soles, tubing, sporting goods, sealants, gaskets, and oil gels.
  • the compositions also find use as rubber toughening agents for polyolefins, polyvinyl chloride, polystyrene, polyamide, polyurethane, polyester, polycarbonate and epoxy resins.
  • the polymers of the present invention are also useful in alloys and blends, and as compatibilizers for a variety of polymers and other materials. Improved elasticity when compared with conventional styrenic block copolymers makes these copolymers particularly useful for adhesives, including both pressure-sensitive and hot-melt adhesives.
  • the key component of the present invention is the novel block copolymer containing monoalkenyl arene end blocks and a unique midblock of a monoalkenyl arene and a conjugated diene.
  • the combination of (1) a unique order for the monomer addition and (2) the use of diethyl ether or other ethers as a component of the solvent results in a certain marked uniformity of the distribution of the two monomers (herein termed a “controlled distribution” polymerization, i.e., a polymerization resulting in a “controlled distribution” structure), and also results in the presence of certain mono alkenyl arene rich regions and certain conjugated diene rich regions in the polymer block.
  • controlled distribution is defined as referring to a molecular structure lacking well-defined blocks of either monomer, with “runs” of any given single monomer attaining a preferred maximum number average of about 20 units, as shown by either the presence of only a single Tg, intermediate between the Tg's of either monomer alone, when analyzed using differential scanning calorimetry (“DSC”) (thermal) methods or via mechanical methods, or as shown via proton nuclear magnetic resonance (“H-NMR”) methods.
  • DSC differential scanning calorimetry
  • H-NMR proton nuclear magnetic resonance
  • This controlled distribution structure is very important in maintaining the rubbery properties of the polymer with a single, narrow Tg, because the controlled distribution structure ensures that there is virtually no phase separation of the two monomers, i.e., in contrast with block copolymers in which the monomers actually remain as separate “microphases”, with distinct Tg's, but are actually chemically bonded together which produces much more plastic physical properties.
  • the presence of the arene monomer in the rubber segment allows preferential interactions that improve tensile and tear strength as well as adhesion to styrene containing polymers.
  • the controlled distribution structure assures that only one Tg is present and that, therefore, the thermal performance of the resulting copolymer is predictable and, in fact, predeterminable.
  • a copolymer having such a controlled distribution structure when a copolymer having such a controlled distribution structure is then used as one block in a di-block, tri-block or multi-block copolymer, it provides the properties of a rubbery block with the adhesion characteristics of a more polar block. Modification of certain other properties is also achievable.
  • the subject copolymer block also has three distinct regions—conjugated diene rich regions on the end of the block and adjacent to the A blocks and a mono alkenyl arene rich region not adjacent to the A block and near the middle or center of the block.
  • a mono alkenyl arene/conjugated diene controlled distribution copolymer block wherein the proportion of mono alkenyl arene units increases gradually to a maximum near the middle or center of the block and then decreases gradually until the polymer block is fully polymerized.
  • the B block will have terminal regions rich in conjugated diene units, and a center region that is rich in mono alkenyl arene units.
  • the block copolymer When the block copolymer is prepared via a coupling route, it will have a structure (A-B) n X. In that case each B block will have at least one region adjacent to the A block that is rich in conjugated diene units. The other end not adjacent to the A block may or may not be rich in conjugated diene units. The remainder of the block will be therefore rich in mono alkenyl arene units.
  • Another important aspect of the present invention is to control the microstructure or vinyl content of the conjugated diene in the controlled distribution copolymer block.
  • the term “vinyl content” refers to the fact that a conjugated diene is polymerized via 1,2-addition (in the case of butadiene—it would be 3,4-addition in the case of isoprene). Although a pure “vinyl” group is formed only in the case of 1,2-addition polymerization of 1,3-butadiene, the effects of 3,4-addition polymerization of isoprene (and similar addition for other conjugated dienes) on the final properties of the block copolymer will be similar.
  • vinyl refers to the presence of a pendant vinyl group on the polymer chain.
  • butadiene it is preferred that about 20 to about 80 mol percent of the condensed butadiene units in the copolymer block have 1,2 vinyl configuration.
  • the randomization agent serves two purposes—it creates the controlled distribution of the mono alkenyl arene and conjugated diene, and also controls the microstructure of the conjugated diene. Suitable ratios of randomization agent to lithium are disclosed and taught in U.S. Pat. Re No. 27,145.
  • the alkenyl arene can be selected from styrene, alpha-methylstyrene, para-methylstyrene, vinylnaphthalene, and para-butyl styrene, including mixtures thereof.
  • styrene is most preferred and is commercially available, and relatively inexpensive, from a variety of manufacturers.
  • the conjugated dienes for use herein are 1,3-butadiene and substituted butadienes such as isoprene, piperylene, 2,3-dimethyl-1,3-butadiene, and 1-phenyl-1,3-butadiene, or mixtures thereof. Of these, 1,3-butadiene is most preferred.
  • the controlled distribution polymer block has diene rich region(s) adjacent to the A block and an arene rich region not adjacent to the A block, and typically near the center of the block.
  • the region adjacent to the A block comprises the first 15 to 25% of the block and comprises the diene rich region(s), with the remainder considered to be arene rich.
  • the term “diene rich” means that the region has a measurably higher ratio of diene to arene than the arene rich region. Another way to express this is the proportion of mono alkenyl arene units increases gradually along the polymer chain to a maximum near the middle or center of the block (if we are describing an ABA structure) and then decreases gradually until the polymer block is fully polymerized.
  • the weight ratio of conjugated diene to mono alkenyl arene is between about 5:1 and about 1:2, preferably between about 3:1 and about 1:1.
  • a particular feature of the present invention is that the resultant copolymer is relatively uniform in its distribution of the two monomers within a polymer chain, thus offering the improvements in Tg and property modification suggested by the identity of the starting monomers.
  • a proton (hydrogen) nuclear magnetic resonance (H-NMR) procedure may preferably be used to assay for this advantageous controlled distribution, using techniques known to those skilled in the art.
  • a DSC method may be used as an assay, determining the controlled structure of the polymerization by confirming the presence of a desired single Tg as is characteristic of a controlled distribution copolymer.
  • the potential for blockiness can also be inferred from measurement of the UV-visible absorbance in a wavelength range suitable for the detection of polystyrillithium end groups during the polymerization of the B block. A sharp and substantial increase in this value is indicative of a substantial increase in polystyrillithium chain ends. In this process, this will only occur if the conjugated diene concentration drops below the critical level to maintain controlled distribution polymerization. Any styrene monomer that is present at this point will add in a blocky fashion.
  • the term “styrene blockiness” is defined to be the proportion of S units in the polymer having two S nearest neighbors on the polymer chain.
  • Polymer-Bd-S-(S) n -S-Bd-Polymer where n greater than zero is defined to be blocky styrene. For example, if n equals 8 in the example above, then the blockiness index would be 80%.
  • thermoplastic block copolymer is defined as a block copolymer having at least a first block of a mono alkenyl arene, such as styrene and a second block of a controlled distribution copolymer of diene and mono alkenyl arene.
  • the method to prepare this thermoplastic block copolymer is via any of the methods generally known for block polymerizations.
  • the present invention includes as an embodiment a thermoplastic copolymer composition, which may be either a di-block, tri-block copolymer or multi-block composition.
  • one block is the alkenyl arene-based homopolymer block and polymerized therewith is a second block of a controlled distribution copolymer of diene and alkenyl arene.
  • the tri-block composition it comprises, as end-blocks the glassy alkenyl arene-based homopolymer and as a mid-block the controlled distribution copolymer of diene and alkenyl arene.
  • the controlled distribution diene/alkenyl arene copolymer can be herein designated as “B” and the alkenyl arene-based homopolymer designated as “A”.
  • the A-B-A, tri-block compositions can be made by either sequential polymerization or coupling.
  • the sequential solution polymerization technique the mono alkenyl arene is first introduced to produce the relatively hard aromatic block, followed by introduction of the controlled distribution diene/alkenyl arene mixture to form the mid block, and then followed by introduction of the mono alkenyl arene to form the terminal block.
  • the blocks can be structured to form a radial (branched) polymer, (A-B) n X, or both types of structures can be combined in a mixture.
  • Some A-B diblock polymer can be present but preferably at least about 70 weight percent of the block copolymer is A-B-A or radial (or otherwise branched so as to have 2 or more terminal resinous blocks per molecule) so as to impart strength.
  • desired block weights are 3,000 to about 60,000 for the mono alkenyl arene A block, and 30,000 to about 300,000 for the controlled distribution conjugated diene/mono alkenyl arene B block. Preferred ranges are 5000 to 45,000 for the A block and 50,000 to about 250,000 for the B block.
  • the triblock which may be a sequential ABA or coupled (AB) 2 X block copolymer
  • the A blocks should be 3,000 to about 60,000, preferably 5000 to about 45,000
  • the B block for the sequential block should be about 30,000 to about 300,000, and the B blocks (two) for the coupled polymer half that amount.
  • the total average molecular weight for the triblock copolymer should be from about 40,000 to about 400,000, and for the radial copolymer from about 60,000 to about 600,000. These molecular weights are most accurately determined by light scattering measurements.
  • thermoplastic elastomeric di-block and tri-block polymers of the present invention including one or more controlled distribution diene/alkenyl arene copolymer blocks and one or more mono alkenyl arene blocks, is that they have at least two Tg's, the lower being the combined Tg of the controlled distribution copolymer block which is an intermediate of its constituent monomers' Tg's.
  • Tg is preferably at least about ⁇ 60 degrees C., more preferably from about ⁇ 40 degrees C. to about zero degrees C., and most preferably from about ⁇ 40 degrees C. to about ⁇ 10 degrees C.
  • the second Tg that of the mono alkenyl arene “glassy” block, is preferably more than about 80 degrees C. , more preferably from about 80 degrees C. to about 105 degrees C.
  • the presence of the two Tg's, illustrative of the microphase separation of the blocks, contributes to the notable elasticity and strength of the material in a wide variety of applications, and its ease of processing and desirable melt-flow characteristics.
  • the block copolymer is selectively hydrogenated. Hydrogenation can be carried out via any of the several hydrogenation or selective hydrogenation processes known in the prior art. For example, such hydrogenation has been accomplished using methods such as those taught in, for example, U.S. Pat. Nos. 3,494,942; 3,634,594; 3,670,054; 3,700,633; and Re. No. 27,145. Hydrogenation can be carried out under such conditions that at least about 90 percent of the conjugated diene double bonds have been reduced, and between zero and 10 percent of the arene double bonds have been reduced. Preferred ranges are at least about 95 percent of the conjugated diene double bonds reduced, and more preferably about 98 percent of the conjugated diene double bonds are reduced. Alternatively, it is possible to hydrogenate the polymer such that aromatic unsaturation is also reduced beyond the 10 percent level mentioned above. In that case, the double bonds of both the conjugated diene and arene may be reduced by 90 percent or more.
  • the block copolymer of the present invention may be functionalized in a number of ways.
  • One way is by treatment with an unsaturated monomer having one or more functional groups or their derivatives, such as carboxylic acid groups and their salts, anhydrides, esters, imide groups, amide groups, and acid chlorides.
  • the preferred monomers to be grafted onto the block copolymers are maleic anhydride, maleic acid, fumaric acid, and their derivatives.
  • a further description of functionalizing such block copolymers can be found in Gergen et al, U.S. Pat. No. 4,578,429 and in U.S. Pat. No. 5,506,299.
  • the selectively hydrogenated block copolymer of the present invention may be functionalized by grafting silicon or boron containing compounds to the polymer as taught in U.S. Pat. No. 4,882,384.
  • the block copolymer of the present invention may be contacted with an alkoxy-silane compound to form silane-modified block copolymer.
  • the block copolymer of the present invention may be functionalized by grafting at least one ethylene oxide molecule to the polymer as taught in U.S. Pat. No. 4,898,914, or by reacting the polymer with carbon dioxide as taught in U.S. pat. No. 4,970,265.
  • block copolymers of the present invention may be metallated as taught in U.S. Pat. Nos. 5,206,300 and 5,276,101, wherein the polymer is contacted with an alkali metal alkyl, such as a lithium alkyl.
  • the block copolymers of the present invention may be functionalized by grafting sulfonic groups to the polymer as taught in U.S. Pat. No. 5,516,831.
  • One of the surprising compositions of the present invention is the combination of the hydrogenated block copolymer and a polymer extending oil. While in the absence of oil, these polymers exhibit a stiffer elastomeric behavior than a traditional triblock polymer, in the presence of oil, they exhibit a softer elastomeric behavior.
  • Especially preferred are the types of oil that are compatible with the elastomeric segment of the block copolymer. While oils of higher aromatics content are satisfactory, those petroleum-based white oils having low volatility and less than 50% aromatic content are preferred. The oils should additionally have low volatility, preferable having an initial boiling point above about 500° F.
  • the amount of oil employed varies from about 0 to about 300 parts by weight per hundred parts by weight rubber, or block copolymer, preferably about 20 to about 150 parts by weight.
  • the block copolymers of the present invention may be blended with a large variety of other polymers, including olefin polymers, styrene polymers, tackifying resins, and engineering thermoplastic resins.
  • Olefin polymers include, for example, ethylene homopolymers, ethylene/alpha-olefin copolymers, propylene homopolymers, propylene/alpha-olefin copolymers, high impact polypropylene, butylene homopolymers, butylene/alpha olefin copolymers, and other alpha olefin copolymers or interpolymers.
  • Representative polyolefins include, for example, but are not limited to, substantially linear ethylene polymers, homogeneously branched linear ethylene polymers, heterogeneously branched linear ethylene polymers, including linear low density polyethylene (LLDPE), ultra or very low density polyethylene (ULDPE or VLDPE), medium density polyethylene (MDPE), high density polyethylene (HDPE) and high pressure low density polyethylene (LDPE).
  • LLDPE linear low density polyethylene
  • ULDPE or VLDPE ultra or very low density polyethylene
  • MDPE medium density polyethylene
  • HDPE high density polyethylene
  • LDPE high pressure low density polyethylene
  • ESA ethylene/acrylic acid
  • EMA ethylene/methacrylic acid
  • EVA ethylene/vinyl acetate
  • EVA ethylene/vinyl alcohol
  • EVOH ethylene/cyclic olefin copolymers
  • polypropylene homopolymers and copolymers propylene/styrene copolymers
  • ethylene/propylene copolymers polybutylene
  • ethylene carbon monoxide interpolymers for example, ethylene/carbon monoxide (ECO) copolymer, ethylene/acrylic acid/carbon monoxide terpolymer and the like.
  • Still other polymers included hereunder are polyvinyl chloride (PVC) and blends of PVC with other materials.
  • Styrene polymers include, for example, crystal polystyrene, high impact polystyrene, medium impact polystyrene, styrene/acrylonitrile copolymers, styrene/acrylonitrile/butadiene (ABS) polymers, syndiotactic polystyrene and styrene/olefin interpolymers.
  • Representative styrene/olefin interpolymers are substantially random ethylene/styrene interpolymers, preferably containing at least 20, more preferably equal to or greater than 25 weight percent interpolymerized styrene monomer.
  • thermoplastic resin encompasses the various polymers found in the classes listed in Table A below, and further defined in U.S. Pat. No. 4,107,131, the disclosure of which is hereby incorporated by reference.
  • TABLE A 1. Thermoplastic Polyester 2. Thermoplastic Polyurethane 3. Poly(aryl ether) and Poly(aryl sulfone) 4. Polycarbonate 5. Acetal resin 6. Polyamide 7. Halogenated thermoplastic 8. Nitrile barrier resin 9. Poly(methyl methacrylate)
  • Tackifying resins include polystyrene block compatible resins and midblock compatible resins.
  • the polystyrene block compatible resin may be selected from the group of coumarone-indene resin, polyindene resin, poly(methyl indene) resin, polystyrene resin, vinyltoluene-alphamethylstyrene resin, alphamethylstyrene resin and polyphenylene ether, in particular poly(2,6-dimethyl-1,4-phenylene ether).
  • Such resins are e.g. sold under the trademarks “HERCURES”, “ENDEX”, “KRISTALEX”, “NEVCHEM” and “PICCOTEX”.
  • Resins compatible with the hydrogenated (mid) block may be selected from the group consisting of compatible Cs hydrocarbon resins, hydrogenated C 5 hydrocarbon resins, styrenated C 5 resins, C 5 /C 9 resins, styrenated terpene resins, fully hydrogenated or partially hydrogenated Cg hydrocarbon resins, rosins esters, rosins derivatives and mixtures thereof. These resins are e.g. sold under the trademarks “REGALITE”, “REGALREZ”, “ESCOREZ” and “ARKON”. The resin employed will typically have a viscosity at 350° F., of no more than 300 centipoise.
  • polymer blends of the present invention may be compounded further with other polymers, oils, fillers, reinforcements, antioxidants, stabilizers, fire retardants, antiblocking agents, lubricants and other rubber and plastic compounding ingredients without departing from the scope of this invention.
  • a reinforcement may be defined simply as the material that is added to a resinous matrix to improve the strength of the polymer. Most of these reinforcing materials are inorganic or organic products of high molecular weight. Various examples include glass fibers, asbestos, boron fibers, carbon and graphite fibers, whiskers, quartz and silica fibers, ceramic fibers, metal fibers, natural organic fibers, and synthetic organic fibers. Especially preferred are reinforced polymer blends of the instant invention containing about 2 to about 80 percent by weight glass fibers, based on the total weight of the resulting reinforced blend. Coupling agents, such as various silanes, may be employed in the preparation of the reinforced blends.
  • the polymer of the present invention may be used in a large number of applications, either as a neat polymer or in a compound.
  • the following various end uses and/or processes are meant to be illustrative, and not limiting to the present invention:
  • Various controlled distribution block copolymers of the present invention were prepared according to the process disclosed in copending patent application Serial No. 60/355,210 referenced above. All polymers were selectively hydrogenated linear ABA block copolymers where the A blocks were polystyrene blocks and the B block prior to hydrogenation was a styrene butadiene controlled distribution block having terminal regions that are rich in butadiene units and a center region that was rich in styrene units. The various polymers are shown in Table 1 below. These polymers were then used in the various applications described in the other Examples.
  • Step I MW is the molecular weight of the first A block
  • Step II MW is the molecular weight of the AB blocks
  • Step III MW is the molecular weight of the ABA blocks.
  • the polymers were hydrogenated such that greater than about 95% of the diene double bonds have been reduced.
  • the increased recoverable energy and decreased hysteresis set is desirable for improved elasticity of a film.
  • the advantage of polymers 14 and 15 over G11652 shows in the increased isotropic behavior seen in the Elmendorf Tear data. Isotropic tear is advantageous in film applications where straight tear along a seam is necessary, such as food wrap or wrapping for sterile surgical kits.
  • the modulus and hysteresis values for the comparison example 4-1 vary by almost a factor of two between the machine direction, MD, and transverse direction, TD. This indicates a high degree of orientation during film casting resulting in film with highly anistropic properties and dimensional instability.
  • comparison examples 4-2 and 4-3 show a much smaller difference in Modulus, recoverable energy and permanent set at all elongations between the MD and TD directions.
  • the values of recoverable energy and permanent set in the MD for examples 4-2 and 4-3 are surprisingly low, indicating a much more elastic film than a traditional SEBS triblock copolymer.
  • Examples 5-2 through 5-4 are transparent with excellent hysteresis recovery and low permanent set.
  • the higher styrene content of 2901 TE produces opaque compounds (examples 5-8 through 5-13) that still retain high strength and elongation across the range.
  • Examples 5-2 through 5-6 have the unexpected benefit of having higher tensile strength than the two polymers of which they are composed.
  • compositions based on polymers #9 and 11 are more isotropic than the comparison polymer while maintaining a good balance of properties. They can also be blended with a variety of engineering thermoplastics to yield a good balance of isotropic properties.
  • Polymers 3, 4 and 5 show isotropic behavior for mechanical properties, but G 1651 does not. Polymer 5 molecular weight is less than G 1651 by 50,000, yet exhibits the same tensile and elongation properties. Modulus for polymers 3,4 and 5 are slightly higher than that of G 1651, indicating that the compound is slightly stiffer. Coefficient of friction shows that increasing the amount of styrene in the midblock lowers the surface friction of the molded part.
  • the first set of compounds (numbers 1 to 6) were prepared in the brabender mixing head on small scale. Following that larger amounts of the control formulation containing G-1730 and one other controlled distribution copolymer compound (compound #7 and 8) were compounded on a twin screw extruder. The pellets were then transformed into film on a cast film line. The properties of those films were measured in the machine (MD) and transverse (TD) directions.
  • MD machine
  • TD transverse
  • the films made form the present invention surprisingly have much greater tear strength than the control films.
  • TABLE 11A Compounds: 1 2 3 4 5 6 Polymer G-1730 #2 #3 G-1730 #2 #3 Polymer 68% 68% 68% 84.80% 84.80% 84.80% Regalrez 1126 20% 20% 20% PE NA601 11.80% 11.80% 11.80% 15% 15% 15% AO 330 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20% 0.20%
  • Example #9 This example is similar to Example #6, in that one controlled distribution block copolymer (#9) was compared against a selectively hydrogenated SBS block copolymer (KRATON G 1654) in a compound with extending oil and polypropylene homopolymer. The results are shown in Table 12. As shown in Table 12, the composition with Polymer #9 has much improved melt flows compared to compositions made with G-1654. Surprisingly, the compression set of the two compounds are nearly the same. This means that the compound made with Polymer #9 can be much more easily molded than the compound containing G-1654 while retaining approximately the same properties.
  • KRATON G 1654 selectively hydrogenated SBS block copolymer

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US10/209,285 US20030181584A1 (en) 2002-02-07 2002-07-31 Elastomeric articles prepared from controlled distribution block copolymers
US10/359,907 US7267855B2 (en) 2002-02-07 2003-02-06 Articles prepared from hydrogenated controlled distribution block copolymers
US10/359,953 US7847022B2 (en) 2002-02-07 2003-02-06 Articles prepared from controlled distribution block copolymers
EP20030707247 EP1474459B1 (fr) 2002-02-07 2003-02-07 Articles obtenus a partir de copolymeres sequences hydrogenes a distribution commandee
DE60330119T DE60330119D1 (de) 2002-02-07 2003-02-07 Gegenstände aus hydrierten blockcopolymeren mit kontrollierter verteilung
CN038074826A CN1643015B (zh) 2002-02-07 2003-02-07 由氢化的控制分布嵌段共聚物制备的制品
EP20030737512 EP1483328B1 (fr) 2002-02-07 2003-02-07 Articles prepares a partir de copolymeres sequences a distribution commandee
AU2003208667A AU2003208667A1 (en) 2002-02-07 2003-02-07 Solvent-free, hot melt adhesive composition comprising a controlled distribution block copolymer
CN038074605A CN1643058B (zh) 2002-02-07 2003-02-07 从受控分布嵌段共聚物制备的制品
DE2003616262 DE60316262T2 (de) 2002-02-07 2003-02-07 Gegenstände aus blockcopolymeren mit kontrollierter verteilung
TW92102528A TWI256969B (en) 2002-02-07 2003-02-07 Solvent-free, hot melt adhesive composition comprising a controlled distribution block copolymer
EP20030707250 EP1474495B1 (fr) 2002-02-07 2003-02-07 Composition adhesive thermofusible sans solvant comportant un copolymere bloc a distribution controlee
DE2003606493 DE60306493T2 (de) 2002-02-07 2003-02-07 Lösungsmittelfreie heissschmelzklebstoffzusammensetzung, die blockcopolymeren mit kontrollierter verteilung enthält
PCT/NL2003/000098 WO2003066769A1 (fr) 2002-02-07 2003-02-07 Composition adhesive thermofusible sans solvant comportant un copolymere bloc a distribution controlee
AT03707250T ATE331775T1 (de) 2002-02-07 2003-02-07 Lösungsmittelfreie heissschmelzklebstoffzusammensetzung, die blockcopolymeren mit kontrollierter verteilung enthält
TW92102541A TWI300781B (en) 2002-02-07 2003-02-07 Articles prepared from hydrogenated controlled distribution block copolymers
AT03737512T ATE373045T1 (de) 2002-02-07 2003-02-07 Gegenstände aus blockcopolymeren mit kontrollierter verteilung
CNB038074478A CN1311044C (zh) 2002-02-07 2003-02-07 包括控制分布嵌段共聚物的无溶剂热熔粘合剂组合物
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WO2003066731A1 (fr) 2003-08-14
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US7267855B2 (en) 2007-09-11
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US7847022B2 (en) 2010-12-07
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