Classifications

• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B60—VEHICLES IN GENERAL
  • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
  • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
  • B60C1/0016—Compositions of the tread
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
  • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
  • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
  • C08G63/46—Polyesters chemically modified by esterification
  • C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0016—Plasticisers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/05—Alcohols; Metal alcoholates
  • C08K5/053—Polyhydroxylic alcohols
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L21/00—Compositions of unspecified rubbers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
  • C08L67/08—Polyesters modified with higher fatty oils or their acids, or with resins or resin acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
  • C08L9/06—Copolymers with styrene
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
  • C08L93/04—Rosin
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
  • C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
  • C09F1/04—Chemical modification, e.g. esterification
• • 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
  • C09J193/00—Adhesives based on natural resins; Adhesives based on derivatives thereof
  • C09J193/04—Rosin

Definitions

• Rosin esters including rosin esters derived from polyhydric alcohols, have been known for more than 50 years. See, for example, U.S. Patent No. 1,820,265 to Bent, et al. Rosin esters are typically formed by the reaction of rosin, which is primarily a mixture of isomeric C 20 tricyclic mono-carboxylic acids known as rosin acids, with alcohols such as glycerol or pentaerythritol.
• an oligoester composition which is an esterification reaction product of one or more rosins, one or more monocarboxylic acids, one or more polyhydric alcohols, and optionally one or more polycarboxylic acids, wherein the composition has a weight average molecular weight of from 500 g/mol to 8,000 g/mol and a Tg of between -80°C and 100°C.
• PSA pressure sensitive adhesive
• a pressure sensitive adhesive comprising a polymer and an oligoester, wherein the adhesive exhibits a loop tack adhesion value on stainless steel of at least 25 Newton/25 mm, a 180° peel adhesion on stainless steel after 20 minutes of at least 20 Newton/25 mm, a shear adhesion time of at least 3000 minutes, and a SAFT failure temperature of at least 55°C.
• oligoesters and oligoester compositions may comprise, consist of, or consist essentially of the oligoesters disclosed herein.
• the oligoester composition comprises from 1 weight percent (wt.%) to 100 wt.% of one or more oligoesters of the type disclosed herein based on the total weight of the composition, alternatively from 10 wt.% to 100 wt.%, alternatively from 20 wt.% to 80 wt.%, alternatively from 30 wt.% to 70 wt.%.
• the oligoester compositions described herein may be derived from one or more rosins.
• Rosin also called colophony or Greek pitch (Pix grteca)
• Rosin is a solid hydrocarbon secretion of plants, typically of conifers such as pines (e.g., Pinus palustris and Pinus caribaea).
• Rosin may include a mixture of rosin acids, with the precise composition of the rosin varying depending in part on the plant species. Rosin acids are C20 fused-ring monocarboxylic acids with a nucleus of three fused six-carbon rings containing double bonds that vary in number and location.
• the oligoester may be derived from a rosin having a low PAN number.
• the rosin as obtained by hydrolysis from the oligoester may have a PAN number, as determined according to the method described in ASTM D5974-00 (2010), of equal to or less than 25, alternatively equal to or less than 15, or alternatively equal to or less than 5.
• the rosin as obtained by hydrolysis from the oligoester may comprise from equal to or greater than 30 wt.% dehydroabietic acid, alternatively from 30 wt.% to 60 wt.% , or alternatively from 40 wt.% to 55 wt.% based on the total weight of the rosin.
• the one or more polycarboxylic acids may comprise any suitable polycarboxylic acids.
• the one or more polycarboxylic acids may comprise a dicarboxylic acid.
• the one or more polycarboxylic acids may comprise a tricarboxylic acid.
• the one or more polycarboxylic acids may comprise a tetracarboxylic acid.
• the one or more polycarboxylic acids comprise from 2 to 54 carbon atoms (e.g., from 4-35 carbon atoms, from 6-12 carbon atoms).
• the oligoester composition may have a weight average molecular weight (MW), as determined using gel permeation chromatography (GPC) as described in ASTM D5296-05, from 500 g/mol to 8000 g/mol, alternatively from 700 g/mol to 8000 g/mol, alternatively from 1000 g/mol to 5000 g/mol, or alternatively from 1100 g/mol to 3000 g/mol. In certain aspects, less than 35 wt.%, alternatively less than 20 wt.%, or alternatively less than 13 wt.% by weight of the oligoester composition has a molecular weight of less than 1,000 g/mol, as determined by GPC.
• MW weight average molecular weight
• Exemplary (meth) acrylate monomers include, but are not limited to, methyl acrylate, methyl (meth)acrylate, ethyl acrylate, ethyl (meth)acrylate, butyl acrylate, butyl (meth)acrylate, isobutyl (meth) acrylate, n- hexyl (meth)acrylate, ethylhexyl (meth)acrylate, n-heptyl (meth)acrylate, ethyl (meth) acrylate, 2- methylheptyl (meth) acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, n-nonyl (meth) acrylate, isononyl (meth)acrylate, n-decyl (meth)acrylate, isodecyl (meth) acrylate, dodecyl (meth)acrylate, lau
• the polymer is poly(ethylene-co- vinyl acetate) (EVA).
• EVA is a copolymer derived from ethylene and vinyl acetate. EVA is widely used in a variety of applications, including as a copolymer in hot-melt adhesives, in road marking and pavement marking applications, in biomedical applications (e.g., as a matrix for controlled drug delivery), as an additive in plastic films, and as a foam in a variety of consumer products.
• the EVA copolymer may be grafted with suitable olefinic monomers, such as butadiene, to obtain copolymers having the particular chemical and physical properties required for a particular application. See, for example, U.S. Patent Nos. 3,959,410 to DiRossi and 5,036,129 to Atwell, et al.
• the polymer may be present in the polymeric compositions in varying amounts, depending upon the desired properties of the composition.
• the polymer comprises in between 5 wt.% and 95 wt.%, alternatively between 10 wt.% and 90 wt.%, alternatively between 20 wt.% and 80 wt.%, or alternatively between 30 wt.% and 70 wt.% by weight of the composition.
• the polymeric composition may be an adhesive formulation (e.g., hot-melt adhesive formulation, a pressure sensitive adhesive (PSA), or a water-based adhesive), an ink formulation, a coating formulation, a textile formulation, a plasticized polymer formulation (e.g., a plastic), a rubber formulation (e.g., a tire or tire tread), a sealant formulation, an asphalt formulation, a roof coating formulation, a bitumen formulation, or a pavement marking formulation (e.g., a thermoplastic road marking formulation).
• PSA pressure sensitive adhesive
• water-based adhesive e.g., a water-based adhesive
• the temperature at which the maximum loss tangent (tan5) peak value occurs may be determined by DMA and provides an estimation of Tg. It may make sense for comparative purposes to adjust the temperature at which the maximum loss tangent (tan5) peak occurs for two different adhesive blends to the same temperature value by adjusting the blend ratio of their components as an enabler for meaningful property comparisons.
• meaningful properties may be tack, peel and shear resistance, including the shear adhesion failure temperature (SAFT) value. It is known that it may be difficult to simultaneously achieve high tack, peel and shear performances in an adhesive pressure sensitive adhesive formulation. There exists still a commercial need for pressure sensitive adhesives which provide an increased shear performance or higher SAFT temperature while maintaining their tack and peel performance levels.
• Representative synthetic rubber polymers are the homopolymerization products of butadiene and its homologues and derivatives, for example, methylbutadiene, dimethylbutadiene and pentadiene, as well as copolymers such as those formed from butadiene or its homologues or derivatives with other unsaturated monomers.
• the polymeric compositions provided herein exhibit less than a
• Plasticizers may make an important contribution to improve the performance in a variety of industrial applications wherein polymers, plastics or other macromolecular chemical entities, or mixtures or blends thereof, are applied such as in adhesives, including water-based adhesives applications and adhesive tapes, coatings, roofing, road pavement, asphalt, bitumen and road marking formulations, films, textiles, automotive, paints, flooring, sealants, polymer emulsions, conveyor belts, gaskets, hoses, and pharmaceutical applications.
• adhesives including water-based adhesives applications and adhesive tapes, coatings, roofing, road pavement, asphalt, bitumen and road marking formulations, films, textiles, automotive, paints, flooring, sealants, polymer emulsions, conveyor belts, gaskets, hoses, and pharmaceutical applications.
• the composition may comprise a second plasticizer comprising phthalate ester, azelate ester, 1,2-cyclohexane dicarboxylate ester, trimellitate ester, succinate ester, glutarate ester, adipate ester, sebacate ester, citrate ester, ester, terephthalate ester, epoxidized fatty ester, benzoate ester, a phosphate ester, or a combination of any two or more thereof.
• a second plasticizer comprising phthalate ester, azelate ester, 1,2-cyclohexane dicarboxylate ester, trimellitate ester, succinate ester, glutarate ester, adipate ester, sebacate ester, citrate ester, ester, terephthalate ester, epoxidized fatty ester, benzoate ester, a phosphate ester, or a combination of any two or more thereof.
• the oligoester compositions described herein may also be prepared by an interesterification process, which is mechanistically related to esterification and transesterification.
• Interesterification may be carried out by blending different esters and then rearranging the carboxylic acid moieties over the applied polyhydric alcohol backbones in the presence of a catalyst, for example an esterification catalyst.
• Interesterifications are equilibrium reactions.
• a rosin ester may be reacted with a triglyceride ester, such as rapeseed oil.
• alkyl groups include straight chain and branched alkyl groups having from 1 to about 40 carbon atoms. As employed herein, “alkyl groups” include cycloalkyl groups as defined below. Alkyl groups may be substituted or unsubstituted.
• Representative substituted cycloalkyl groups may be mono- substituted or substituted more than once, such as, but not limited to: 2,2-; 2,3-; 2,4-; 2,5-; or 2,6- disubstituted cyclohexyl groups or mono-, di-, or trisubstituted norbornyl or cycloheptyl groups.
• Glass transition temperature (Tg) values of the oligoesters were determined by means of Differential Scanning Calorimetry (DSC): Equipment description: TA Instruments Q2000, based on Tzero principle, combined with the TA Refrigerated Cooling System 90. Cup description: Tzero Aluminum Hermetic with pierced lid. Applied gas and flow rate: N 2 , 50 ml/min. Temperature program description:
• Peel adhesion tests (FTM 1, Peel adhesion (180°) at 300 mm per minute), loop tack tests (FTM 9, Loop' tack measurement) and Resistance to shear (FTM 8, Resistance to shear from a standard surface) were conducted according to the test procedures as described in the Finat Technical Handbook, Test Methods, 9th edition, FINAT, The Hague, The Netherlands, May 2014. An RK K Control Coater (RK PrintCoat Instruments Ltd) was used.
• the turbidity detection system of the CHEMOTRONIC equipment is based on light transmission.
• turbidity is detected by the absorption due to suspended particles in the liquid and may be associated to a cloud point and qualitatively to a degree of incompatibility.
• the degree of light transmission through a molten hot-melt adhesive sample versus temperature was measured across a temperature range of 20°C to 230°C. The resulting relationship is represented as a graphical representation.
• the light transmission is given as % transmitted light and the temperature is provided as °C.
• Example 17 The procedure of Example 17 was repeated, except that a higher top temperature of
• reaction mixture (160.0 g, acid value 169 mg KOH/g), pentaerythritol (38.922 g), ROSINOXTM (0.327 g), IRGANOXTM 1425 (0.801 g and SYLFATTM 2LT (160.07 g).
• the reaction mixture was heated at 285°C instead of 275 °C for 8 hours. Reaction yield: 295.2 g.
• Oligoester 24 (50 g) was placed in ajar (118 mL) and heated at 40 °C in an oven for
• the loss modulus (G) values are shown in logarithmic scale (ranging from 102 to 109) and expressed in Pascal units according to the left vertical axis numerical values as a function of the temperature (in °C). As shown in Figures 1 and 2, adhesive formulations prepared using oligoesters exhibit similar dynamic mechanical properties to adhesive formulations prepared using conventional liquid rosin esters. Pressure Sensitive Adhesive Formulations
• the oligoester of Example 24 exhibited a more stable viscosity upon aging than 54 the alkyd-like material of Example 54.
• the oligoester of Example 24 exhibited a lower initial viscosity than the alkyd-like material of Example 54.
• compositions and methods of the appended claims are not limited in scope by the specific compositions and methods described herein, which are intended as illustrations of a few aspects of the claims. Any compositions and methods that are functionally equivalent are intended to fall within the scope of the claims. Various modifications of the compositions and methods in addition to those shown and described herein are intended to fall within the scope of the appended claims. Further, while only certain representative compositions and method steps disclosed herein are specifically described, other combinations of the compositions and method steps also are intended to fall within the scope of the appended claims, even if not specifically recited. Thus, a combination of steps, elements, components, or constituents may be explicitly mentioned herein or less, however, other combinations of steps, elements, components, and constituents are included, even though not explicitly stated.
• a fifth aspect which is the oligoester composition of any preceding aspect, wherein the composition is derived from no polycarboxylic acids.
• a sixth aspect which is the oligoester composition of any preceding aspect, wherein the composition is derived from 15% to 90% by weight one or more monocarboxylic acids, or from at least 20% by weight one or more monocarboxylic acids, or from 25% to 85% by weight one or more monocarboxylic acids, or from 35% to 85% by weight one or more monocarboxylic acids, or from 40% to 80% by weight one or more monocarboxylic acids.
• a seventh aspect which is the oligoester composition of any preceding aspect, wherein the one or more monocarboxylic acids comprise at least six carbon atoms.
• An eighth aspect which is the oligoester composition of any preceding aspect, wherein the one or more monocarboxylic acids comprise a fatty acid.
• a tenth aspect which is the oligoester composition of any preceding aspect, wherein the one or more monocarboxylic acids are selected from the group consisting of oleic acid, linoleic acid, alpha-linolenic acid, palmitic acid, stearic acid, and combinations thereof.
• An eleventh aspect which is the oligoester composition of any preceding aspect, wherein the one or more monocarboxylic acids comprise a tall oil fatty acid.
• a twelfth aspect which is the oligoester composition of any preceding aspect wherein the one or more monocarboxylic acids have an iodine number of less than 115 mg/g, or less than 80 mg/g as determined according to the method described in ASTM D5768-02 (2014).
• a fourteenth aspect which is the oligoester composition of any preceding aspect, wherein the one or more polyhydric alcohols have an average hydroxyl functionality of from two to ten.
• a fifteenth aspect which is the oligoester composition of any preceding aspect, wherein the one or more polyhydric alcohols comprise from 2 to 30 carbon atoms or from 2 to 16 carbon atoms.
• An eighteenth aspect which is the oligoester composition of any preceding aspect, wherein the one or more polyhydric alcohols comprise a polyol that comprises a first hydroxyl group separated from a second hydroxyl group by at least three carbon atoms or at least six carbon atoms.
• a nineteenth aspect which is the oligoester composition of any preceding aspect, wherein the one or more polyhydric alcohols comprise a polyol wherein each hydroxyl group of the polyol is separated from the other hydroxyl group of the polyol by at least three carbon atoms or at least six carbon atoms.
• a twenty-second aspect which is the oligoester composition of any preceding aspect, wherein the one or more polyhydric alcohols are selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, neopentylglycol, trimethylene glycol, glycerol, trimethylolpropane, trimethylolethane, pentaerythritol, pentaerythritol technical grade, dipentaerythritol, tripentaerythritol, 1,4-cyclohexanediol, poly glycerol, poly glycerol technical grade, polyglycerol- 3, polyglycerol-4, cyclohexane- l,4-dimethanol, tricyclo[5.2.1.0(2.6)]decane-4,8-dimethanol, hydrogenated bisphenol A, (4,4'-Isopropyl, poly
• a twenty-fifth aspect which is the oligoester composition of any preceding aspect, wherein the rosin as obtained by hydrolysis from the oligoester has a PAN number of less than 15, or less than 10, or less than 5, as determined according to the method described in ASTM D5974-00 (2010).
• a twenty-sixth aspect which is the oligoester composition of any preceding aspect, wherein the rosin comprises at least 35% by weight, or at least 45% by weight dehydroabietic acid, based on the total weight of the rosin as obtained by hydrolysis from the oligoester.
• a twenty-seventh aspect which is the oligoester composition of any preceding aspect, wherein the ratio of the weight of one or more polycarboxylic acids to the weight of the rosin and the one or more monocarboxylic acids is less than 1 :20, or less than 1:30, or less than 1 :50, or less than 1 :100.
• a twenty-eighth aspect which is the oligoester composition of any preceding aspect, wherein the ratio of the weight of the rosin to the weight of the one or more monocarboxylic acids ranges from 60:40 to 10:85.
• a thirtieth aspect which is the oligoester composition of any preceding aspect, wherein the oligoester composition is derived from; 15% to 75% by weight rosin; from 36% to 80% by weight one or more monocarboxylic acids; from 9% to 35% by weight one or more polyhydric alcohols; and from 0% to less than 4% by weight one or more polycarboxylic acids.
• a thirty-first aspect which is the oligoester composition of any preceding aspect, wherein the oligoester composition is derived from: 30% to 75% by weight rosin; from 25% to 60% by weight one or more monocarboxylic acids; from 5% to 18% by weight one or more polyhydric alcohols; and from 0% to less than 4% by weight one or more polycarboxylic acids.
• a thirty-second aspect which is the oligoester composition of any preceding aspect, wherein the composition exhibits an oxidative-induction onset time at 110°C of at least 30 minutes, or of at least 40 minutes, as measured using the methods specified in ASTM D5483- 05(2010).
• a thirty-third aspect which is the oligoester composition of any preceding aspect, wherein the composition has a neat Gardner color of 7 or less or 6 or less.
• a thirty-fifth aspect which is the oligoester composition of any preceding aspect, wherein the composition has a weight average molecular weight of at least 500 g/mol, or from 1,000 g/mol to 8,000 g/mol, or from 1,000 g/mol to 5,000 g/mol.
• a thirty-sixth aspect which is the oligoester composition of any preceding aspect, wherein less than 35 percent by weight or less than 20 percent by weight of the oligoester composition has a molecular weight of less than 1,000 g/mol.
• a thirty- seventh aspect which is the oligoester composition of any preceding aspect, wherein less than 10 percent or less than 5 percent by weight of the oligoester composition has a molecular weight of less than 1,000 g/mol.
• a thirty-eigth aspect which is the oligoester composition of any preceding aspect, wherein less than 10 percent or less than 4 percent or less than 2 percent by weight of the oligoester composition has a molecular weight of less than 500 g/mol.
• a thirty-ninth aspect which is the oligoester composition of any preceding aspect, wherein the oligoester composition has an acid value less than 12 mg KOH/gram, or less than 6 mg KOH/gram.
• a fortieth aspect which is the oligoester composition of any preceding aspect, wherein the oligoester composition has a hydroxyl number of less than 30 mg KOH/gram, or less than 20 mg KOH/gram, or less than 12 mg KOH/gram, or less than 6 mg KOH/gram, or than 3 mg KOH/gram.
• a forty-second aspect which is the oligoester composition of the forty-first aspect wherein the composition has a Tg of less than -30°C.
• a forty-fifth aspect which is an oligoester composition of any preceding aspect, wherein enterprise-to-emulsity increase after 16 hours thermal aging at 120°C is less than 8,000 Centipoise or less than 2,500 Centipoise, or less than 1,300 Centipoise at 60°C.
• a forty-seventh aspect which is an oligoester composition derived from one or more rosins one or more monocarboxylic acids; one or more polyhydric alcohols; and less than Q% by weight one or more polycarboxylic acids, where Q is defined by the formula below wherein ⁇ denotes the mathematical summation of the product of X and Y for each of the one or more polycarboxylic acids; X is the carboxylic acid functionality of the polycarboxylic acid, and is an integer ranging from 2 to 4; and Y is the polycarboxylic acid weight fraction of the polycarboxylic acid, and ranges from 0 to 1 with the sum of the weight fractions for the one or more polycarboxylic acids equals 1 ; wherein the oligoester composition has a softening point of 85°C or less; and wherein the oligoester composition has a hydroxyl value of 30 mg KOH/g or less.
• a sixtieth aspect which is the polymeric composition of any of the fifty-third through fifty-ninth aspects further comprising a wax, or an antioxidant, or combinations thereof.
• a sixty-fourth aspect which is the polymeric composition of any of the fifty-third through sixty-third aspects wherein the composition is a pressure sensitive adhesive (PSA).
• PSA pressure sensitive adhesive
• a sixty-fifth aspect which is the polymeric composition of the sixty-fourth aspect, wherein the PSA comprises (a) from 20% by weight to 60% by weight, based on the total weight of the PSA, of a polymer; and (b)from 5% by weight to 50% by weight, based on the total weight of the PSA, of the oligoester composition, wherein the oligoester composition has a glass transition temperature of less than 0°C.
• a seventieth aspect which is the polymeric composition of the sixty-fifth aspect wherein the dispersion comprises particles having a median particle size of from 5 nm to 5000 nm or from 5 nm to 1500 nm, or 5 nm to 500 nm as determined by scanning electron microscopy.
• a seventy-second aspect which is the polymeric composition of the fifty-third aspect wherein the polymer is selected from the group consisting of acrylonitrile-butadiene- styrene, an acrylic polymer, an acrylate copolymer, bromobutyl rubber, butyl terpolymer, cellulose acetate, cellulose butyrate, cellulose propionate, cellulose nitrate, chlorinated polyvinylchloride, polyvinylchloride, chlorosulphonated polyethylene, cyanoacrylates, styrenic block copolymer consisting of polystyrene blocks and rubber blocks wherein the rubber blocks consist of polybutadiene, polyisoprene or hydrogenated versions thereof (SEBS and SEPS triblock copolymers), caprolactone-styrene diblock copolymers, urethane acrylic copolymer, urethanes, polyolefins, ethylene-propylene-diene
• a seventy-third aspect which is the polymeric composition of the fifty-fourth aspect wherein the composition comprise (a) from 20-60% by weight of a polyolefin, and (b) from 20-50% by weight of the oligoester of any preceding claim.
• An eightieth aspect which is the method of any of the seventy-seventh through seventy-ninth aspects wherein the mixture has a stoichiometric molar ratio of total hydroxyl functionality to total carboxyl functionality of 1.20 or less or 1.12 or less or 1.06 or less or 0.94 or less, or from 1.00 to 1.15.
• a eighty-fourth aspect which is method of any of the eighty-first through eighty- third aspects wherein esterifying step (a) comprises contacting the mixture and the one or more polyhydric alcohols with an esterification catalyst wherein the esterification catalyst comprises calcium-bis(((3,5-bis(l,l-dimethylethyl)-4-hydroxyphenyl)methyl)-ethylphosphonate) or wherein esterifying step (a) comprises contacting the mixture and the one or more polyhydric alcohols in the absence of an esterification catalyst.
• a ninety-first aspect which is the composition of any of the eighty-eighth through ninetieth aspects wherein the oligoester composition is present in an amount of from 1 to 80 parts by weight, or 2 to 75 parts by weight, or 5 to 70 parts by weight, or 35 to 75 parts by weight, or 55 to 75 parts by weight based on 100 parts by weight of the rubber polymer.
• An ninety-second aspect which is the composition of any of the eighty-eighth through ninety-first aspects wherein the tire tread composition exhibits improved wet grip as evidenced by an increased tan5 at 0°C or exhibits improved wet grip as evidenced by at least a 10% increase in tan5 at 0°C, or exhibits improved wet grip as evidenced by at least a 15% increase in tan5 at 0°C relative to the same composition wherein the oligoester composition is replaced by treated distillate aromatic extract (TDAE).
• TDAE treated distillate aromatic extract
• a ninety-fifth aspect which is the oligoester of any of the ninety-third through ninety-fourth aspects wherein the oligoester is derived from 30% to 75% by weight rosin; from 25% to 60% by weight one or more monocarboxylic acids; from 5% to 18% by weight one or more polyhydric alcohols; and from 0% to less than 4% by weight one or more polycarboxylic acids.
• a hundreth aspect which is a tire tread composition comprising a rubber polymer, a filler, and an oligoester.
• a hundred and first aspect which is a tire tread composition comprising a rubber polymer, a filler, and an oligoester, wherein the tire tread composition exhibits improved wet grip as evidenced by an increased tan5 at 0°C relative to the same composition wherein the oligoester is replaced by treated distillate aromatic extract (TDAE).
• TDAE treated distillate aromatic extract
• a hundred and third aspect which is the composition of any of the hundred and first through hundred and second aspects wherein the oligoester is present in an amount of from 1 to 80 parts by weight, based on 100 parts by weight of the rubber polymer.
• a hundred and fourth aspect which is the composition of any of the hundred and first through hundred and third aspects wherein the oligoester is present in an amount of from 2 to 75 parts by weight, or of from 5 to 70 parts by weight, or of from 35 to 75 parts by weight, or of from 55 to 75 parts by weight, based on 100 parts by weight of the rubber polymer.
• a hundred and fifth aspect which is the composition of any of the hundred and first through hundred and fourth aspects wherein the tire tread composition exhibits improved wet grip as evidenced by at least a 10% increase in tan5 at 0°C, or exhibits improved wet grip as evidenced by at least a 15% increase in tan5 at 0°C relative to the same composition wherein the oligoester composition is replaced by treated distillate aromatic extract (TDAE).
• TDAE treated distillate aromatic extract

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Polymers & Plastics (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Mechanical Engineering (AREA)
• Adhesives Or Adhesive Processes (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Polyesters Or Polycarbonates (AREA)

Priority Applications (4)

Applications Claiming Priority (2)

Publications (1)

Family

ID=59225834

Family Applications (1)

Country Status (7)

Cited By (3)

Families Citing this family (21)

Citations (28)

Family Cites Families (23)

• 2016
  • 2016-12-30 JP JP2018553851A patent/JP6942723B2/ja active Active
  • 2016-12-30 EP EP16882785.5A patent/EP3397709B1/en active Active
  • 2016-12-30 KR KR1020187022193A patent/KR102786287B1/ko active Active
  • 2016-12-30 US US15/396,258 patent/US10435586B2/en active Active
  • 2016-12-30 CN CN201680080118.7A patent/CN108699395B/zh active Active
  • 2016-12-30 WO PCT/US2016/069594 patent/WO2017117576A1/en not_active Ceased
• 2017
  • 2017-01-03 TW TW106100049A patent/TWI751132B/zh active

Patent Citations (28)

Non-Patent Citations (5)

Also Published As

Similar Documents

Legal Events