[go: up one dir, main page]

WO2025217010A1 - Adhésifs et procédés pour leur fabrication et leur utilisation - Google Patents

Adhésifs et procédés pour leur fabrication et leur utilisation

Info

Publication number
WO2025217010A1
WO2025217010A1 PCT/US2025/023371 US2025023371W WO2025217010A1 WO 2025217010 A1 WO2025217010 A1 WO 2025217010A1 US 2025023371 W US2025023371 W US 2025023371W WO 2025217010 A1 WO2025217010 A1 WO 2025217010A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyester
adhesive
acid
residues
sorbitan
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/023371
Other languages
English (en)
Inventor
Jason John Locklin
Branson W. Ritchie
Evan Michael White
Ethan Jacob Stinchcomb
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Georgia
University of Georgia Research Foundation Inc UGARF
Original Assignee
University of Georgia
University of Georgia Research Foundation Inc UGARF
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 University of Georgia, University of Georgia Research Foundation Inc UGARF filed Critical University of Georgia
Publication of WO2025217010A1 publication Critical patent/WO2025217010A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy 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
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • 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
    • C08G63/16—Dicarboxylic acids and dihydroxy 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
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/672—Dicarboxylic acids and dihydroxy compounds
    • 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
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • C09J167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/334—Applications of adhesives in processes or use of adhesives in the form of films or foils as a label
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2467/00—Presence of polyester

Definitions

  • the adhesive would include all the mechanical and physical properties of adhesives currently used but would break down rapidly and with minimal environmental impact upon disposal.
  • the polyester described herein is compostable, and the adhesives described herein have widespread commercial applicability as a compostable alternative to current non- biodegradable adhesives.
  • the polyesters described herein are suitable for use in a wide variety of adhesives, such as, for example, pressure sensitive adhesives, including compostable pressure sensitive adhesives.
  • the polyester disclosed herein provides both adhesion and tack, allowing pressure sensitive adhesives to be formulated without adding a separate tackifier.
  • FIG.1 provides an exemplary synthetic scheme for producing a polyester described herein.
  • FIG. 2 shows the respirometry analysis of a home compostable adhesive described herein.
  • FIG. 8 shows the respirometry analysis of a home compostable adhesive described herein.
  • FIG. 3 shows the rheological analysis (frequency sweep) of a home compostable pressure sensitive adhesive described herein.
  • FIG.4 shows the loop tack testing of a home compostable pressure sensitive adhesive described herein.
  • the drawings illustrate only example embodiments and are therefore not to be considered limiting of the scope described herein, as other equally effective embodiments are within the scope and spirit of this disclosure.
  • the elements and features shown in the drawings are not necessarily drawn to scale, emphasis instead being placed upon clearly illustrating the principles of the embodiments. Additionally, certain dimensions may be exaggerated to help visually convey certain principles.
  • similar reference numerals between figures designate like or corresponding, but not necessarily the same, elements.
  • each of the terms “by”, “comprising,” “comprises”, “comprised of,” “including,” “includes,” “included,” “involving,” “involves,” “involved,” “having,” and “such as” are used in their open, non-limiting sense and may be used interchangeably.
  • the term “comprising” is intended to include examples and aspects encompassed by the terms “consisting essentially of” and “consisting of.”
  • the term “consisting essentially of” is intended to include examples encompassed by the term “consisting of. [20]
  • the singular forms “a,” “an” and “the” include plural referents unless the context clearly dictates otherwise.
  • a pharmaceutically acceptable carrier includes, but is not limited to, mixtures or combinations of two or more such carriers, and the like.
  • ratios, concentrations, amounts, and other numerical data can be expressed herein in a range format. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint. It is also understood that there are a number of values disclosed herein, and that each value is also herein disclosed as “about” that particular value in addition to the value itself. For example, if the value “10” is disclosed, then “about 10” is also disclosed. Ranges can be expressed herein as from “about” one particular value, and/or to “about” another particular value.
  • a further aspect includes from the one particular value and/or to the other particular value.
  • ranges excluding either or both of those included limits are also included in the disclosure, e.g. the phrase “x to y” includes the range from ‘x’ to ‘y’ as well as the range greater than ‘x’ and less than ‘y’.
  • the range can also be expressed as an upper limit, e.g.
  • ‘about x, y, z, or less’ and should be interpreted to include the specific ranges of ‘about x’, ‘about y’, and ‘about z’ as well as the ranges of ‘less than x’, less than y’, and ‘less than z’.
  • the phrase ‘about x, y, z, or greater’ should be interpreted to include the specific ranges of ‘about x’, ‘about y’, and ‘about z’ as well as the ranges of ‘greater than x’, greater than y’, and ‘greater than z’.
  • a numerical range of “about 0.1% to 5%” should be interpreted to include not only the explicitly recited values of about 0.1% to about 5%, but also include individual values (e.g., about 1%, about 2%, about 3%, and about 4%) and the sub-ranges (e.g., about 0.5% to about 1.1%; about 5% to about 2.4%; about 0.5% to about 3.2%, and about 0.5% to about 4.4%, and other possible sub-ranges) within the indicated range.
  • the terms “about,” “approximate,” “at or about,” and “substantially” mean that the amount or value in question can be the exact value or a value that provides equivalent results or effects as recited in the claims or taught herein.
  • compositions disclosed herein have certain functions. Disclosed herein are certain structural requirements for performing the disclosed functions, and it is understood that there are a variety of structures that can perform the same function that are related to the disclosed structures, and that these structures will typically achieve the same result.
  • a “residue” of a chemical species refers to the moiety that is the resulting product of the chemical species in a particular reaction scheme or subsequent formulation or chemical product, regardless of whether the moiety is actually obtained from the chemical species.
  • a residue of 1,3-propanediol in a polyester refers to one or more -OCH 2 CH 2 CH 2 O- units in the polyester, regardless of whether 1,3-propanediol was used to prepare the polyester.
  • a glutaric acid residue in a polyester refers to one or T
  • the term “aliphatic” or “aliphatic group,” as used herein, denotes a hydrocarbon moiety that may be straight-chain (i.e., unbranched), branched, or cyclic (including fused, bridging, and spirofused polycyclic) and may be completely saturated or may contain one or more units of unsaturation, but which is not aromatic. Unless otherwise specified, aliphatic groups contain 1-20 carbon atoms.
  • Aliphatic groups include, but are not limited to, linear or branched, alkyl, alkenyl, and alkynyl groups, and hybrids thereof such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl or (cycloalkyl)alkenyl.
  • home compostable refers to a material that that satisfies the requirements under AS 5810 / EN 17427 or TÜV AUSTRIA OK Compost Home standards.
  • “ocean compostable” refers to a material that that satisfies the requirements under ASTM D6691 / ISO 22403:2020 or TÜV AUSTRIA OK Biodegradable MARINE .
  • “soil compostable” refers to a material that that satisfies the requirements under ASTM D5988 / ISO 17556 of TÜV AUSTRIA OK Biodegradable SOIL.
  • pressure sensitive adhesive or PSA refers to a nonreactive adhesive that forms a bond when pressure is applied to bond the adhesive with a surface. No solvent, water, or heat is needed to activate the adhesive. Adhesives and Methods for Making and Using the Same [35] Described herein are adhesives composed of a polyester. By varying the components used to produce the polyester, the mechanical and physical properties of the polyester can be modified such that the adhesive is compostable.
  • the adhesives described herein have widespread commercial applicability as a compostable (e.g., home, soil, ocean) alternative (e.g., home, soil, ocean) to current non-biodegradable adhesives such as, for example, pressure sensitive adhesives.
  • the polyesters described herein have a low glass transition temperature, which makes them suitable as adhesives, including compostable adhesives. In one aspect, the polyester has a glass transition temperature of less than about 25 o C as determined by differential scanning calorimetry.
  • the polyester has a glass transition temperature of - 80 o C to less than about 25 o C as determined by differential scanning calorimetry, or -80 o C, - 70 o C, -60 o C, -50 o C, -40 o C, -30 o C, -20 o C, -10 o C, 0 o C, 10 o C, 20 o C, or less than 25 o C, where any value can be a lower and upper endpoint of a range (e.g., -20 o C to 20 o C).
  • the polyesters described herein are amorphous, which also makes them suitable as adhesives, including compostable adhesives.
  • the polyester has a crystallinity T
  • the polyester is the reaction product between one or mor diols and one or more dicarboxylic acids.
  • the selection and amount of each diol and dicarboxylic acid can vary such the final polyester has a glass transition temperature of less than 25 o C and a crystallinity of less than 10%.
  • the polyester is the reaction product of a diol comprising one or more C3 to C20 aliphatic diols and one or more C3 to C20 aliphatic dicarboxylic acids, where the polyester comprises a plurality of residues of a diol comprising one or more C3 to C20 aliphatic diols and one or more C3 to C20 aliphatic dicarboxylic acids.
  • the diol includes 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and any combination thereof.
  • the dicarboxylic acid includes succinic acid, adipic acid, pimelic acid, suberic acid, glutaric acid, and any combination thereof.
  • the polyesters described herein are produced with at least two different carboxylic acids.
  • the first dicarboxylic acid is selected from the group consisting of succinic acid, adipic acid, pimelic acid, suberic acid, and any combination thereof and the second carboxylic acid is glutaric acid.
  • the first carboxylic acid is succinic acid. In another aspect, the first carboxylic acid is glutaric acid and adipic acid. In another aspect, the first carboxylic acid is succinic acid and pimelic acid. In another aspect, the first carboxylic acid is succinic acid, adipic acid, and pimelic acid.
  • the polyester includes (a) a plurality of residues of a diol selected from the group consisting of 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and any combination thereof; (b) a plurality of residues of a first dicarboxylic acid selected from the group consisting of succinic acid, adipic acid, pimelic acid, suberic acid, and any combination thereof; and (c) plurality of residues of a second dicarboxylic comprising glutaric acid.
  • the diol is 1,4-butanediol.
  • the diol is 1,3-propanediol. In another aspect, the diol is 1,4-butanediol and 1,3-propanediol. In one aspect, when the diol is 1,4-butanediol and 1,3-propanediol, the molar ratio of the 1,4-butanediol to 1,3-propanediol is from 4:1 to 7:1.
  • H Docket: 222105-2320 is 4:1, 4.5:1, 5:1, 5.5:1, 6:1, 6.5:1, or 7:1, where any value can be a lower and upper endpoint of a range (e.g., 5:1 to 6:1).
  • modifying the relative amount of 1,4-butanediol to 1,3-propanediol can impact the rheological and thermal transitions of the polyester.
  • the diol component is 100% 1,4- butanediol.
  • the diol component is 1,4-butanediol and 1,3-propanediol, where the molar ratio of the 1,4-butanediol to 1,3-propanediol is from 5:1 to 6:1.
  • the molar ratio of the first dicarboxylic acid to the second dicarboxylic acid is from 1:1 to 1:5.
  • the molar ratio of the first dicarboxylic acid to the second dicarboxylic acid is 1:1, 1:1.5, 1:2, 1:2.5, 1:3, 1:3.5, 1:4, 1:4.5, or 1:5, where any value can be a lower and upper endpoint of a range (e.g., :1:2 to :1:3).
  • the molar ratio of the sum of the first dicarboxylic acid and the second dicarboxylic acid to the diol is from 1:10 to 1:1.
  • the molar ratio of the sum of the first dicarboxylic acid and the second dicarboxylic acid to the diol is from 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, or 1:1, where any value can be a lower and upper endpoint of a range (e.g., 1:5 to 1:3).
  • the molar percentage of hydroxyl groups present in the diol component is greater than the molar percentage of carboxylic acid groups present in the first and second dicarboxylic acids.
  • the molar percentage of hydroxyl groups present in the diol component is up to 5% greater than the molar percentage of carboxylic acid groups present in the first and second dicarboxylic acids. In another aspect, the molar percentage of hydroxyl groups present in the diol component is greater than 0%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, or up to 10% greater than the molar percentage of carboxylic acid groups present in the first and second dicarboxylic acids, where any value can be a lower and upper endpoint of a range (e.g., 1% to 5%). [47] In another aspect, the polyester is the reaction product between one or more hydroxyl carboxylic acid compounds.
  • a hydroxyl carboxylic acid compound is a compound that possess at least one hydroxyl group and at least one carboxylic acid group.
  • the hydroxyl carboxylic acid compound is an omega hydroxy acid.
  • the hydroxyl carboxylic acid compound comprises lactic acid, glycolic acid, 3-hydroxypropionic acid, caproic acid, and any combination thereof.
  • the hydroxyl carboxylic acid compound can also be a precursor compound such as a lactone, wherein the lactone ring opens to produce the hydroxyl carboxylic acid compound
  • the lactone is a C3 to C8 aliphatic lactone.
  • the lactone includes lactide, caprolactone, butyrolactone, or any combination thereof.
  • the polyesters described herein also include a sugar component.
  • the sugar component performs as a crosslinker, and is chemically incorporated in the polyester.
  • the sugar content can be used to modify the rheological and adhesive properties of the polyester.
  • a lower sugar content can decrease the viscous properties of the polyester and decreases the elastic properties of the polyester.
  • a lower sugar content results in a polyester with higher instant tack when measuring loop tack and 90 peel while having an increase in cohesive vs adhesive failure.
  • the sugar has at least two hydroxyl groups per sugar molecule. In another aspect, the sugar has 2, 3, or 4 hydroxyl groups per sugar molecule. In another aspect, the sugar is present in an amount greater than 0 mole percent to 15 mole percent hydroxyl content. The total hydroxyl content is the sum of the mole percent of hydroxyl groups derived from the diol plus the mole percent hydroxyl groups derived from the sugar.
  • the sugar is present in an amount of 25% based on hydroxyl content.
  • the sugar is present in the polyester in an amount of a greater than 0 mole percent to 15 mole percent hydroxyl content, or greater than 0%, 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, or 15%, where any value can be a lower and upper endpoint of a range (e.g., 7% to 11%).
  • the sugar when the adhesive is a pressure sensitive adhesive, the sugar is present in the polyester in an amount of 4 mole percent to 8 mole percent hydroxyl content, preferably 5 mole percent to 7 mole percent hydroxyl content.
  • the sugar can be a monosaccharide (e.g., sucrose, fructose, galactose, xylose, mannose), disaccharide (e.g., sucrose), or oligosaccharide having at least two hydroxyl groups present in the sugar molecule.
  • the sugar is sorbitan or a derivative thereof. Sorbitan has four hydroxyl groups where one or two of the hydroxyl groups can be substituted with a functional group.
  • one or two hydroxyl groups are substituted with an alkyl substituted carboxyl group.
  • sorbitan can be reacted with one or two moles of a saturated or unsaturated fatty acid to produce a sorbitan derivative useful in producing the polyesters described herein.
  • the fatty acid is a C10- T
  • the sugar is sorbitan monooleate, sorbitan monolaurate, sorbitan monostearate, or sorbitan monopalmitate.
  • the polyesters described herein can be produced by mixing the diol and the dicarboxylic acid with the optional sugar followed by heating the mixture for a sufficient time to ensure the reaction is complete.
  • the polyesters described herein can be produced by mixing one or more hydroxyl dicarboxylic acid compounds with the optional sugar followed by heating the mixture for a sufficient time to ensure the reaction is complete.
  • the reaction is conducted at a temperature of from about 100 o C to about 200 o C for 0.1 hours to about 5 hours.
  • the Examples provide non-limiting procedures for making the polyesters described herein.
  • the adhesives described herein consists essentially of or consists of the polyesters described herein.
  • the adhesive can consists essentially of or consist of the polyester without additional components such as, for example, a tackifier, a solvent (e.g., organic solvents or water), or additional polymers typically used to prepare adhesives.
  • the polyesters described herein can be used in combination with one or more additional components to produce home compostable adhesives with desired physical and mechanical properties.
  • one or more additives can be combined with the polyesters described herein to modify the rheological, processing, and adhesive properties of the adhesive.
  • the adhesive includes up to 50 weight percent of one or more additives.
  • the adhesive includes greater than 0 weight percent and up to 50 weight percent of one or more additives, or greater than 0 weight percent, 5 weight percent, 10 weight percent, 15 weight percent, 20 weight percent, 25 weight percent, 30 weight percent, 35 weight percent, 40 weight percent, 45 weight percent, or up to 50 weight percent, where any value can be a lower and upper endpoint of a range (e.g., 10 weight percent to 30 weight percent).
  • the additive does not mineralize below 25°C during home composting.
  • the additive includes a UV absorber, an antioxidant, a viscosity modifier, a thixotropic agent, a hardener, a wax, a tackifier, a plasticizer, or any combination thereof.
  • a ultraviolet absorber is used to improve light resistance of the adhesives described herein.
  • useful UVAs include those described above in conjunction with multilayer film substrates (for example, those available from Ciba Specialty Chemicals Corporation under the trade designations "TINUVIN 328", “TINUVIN 326", “TINUVIN 783", “TINUVIN 770", “TINUVIN 479", “TINUVIN 928”, and “TINUVIN 1577”).
  • the antioxidant prevents oxidative degradation of the adhesives described herein. Examples of the antioxidant include a phenolic antioxidant, a phosphorus antioxidant, a T
  • a phenolic antioxidant is preferred.
  • the phenolic antioxidant include monocyclic phenol compounds such as 2,6-di-tert-butyl-p-cresol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-dicyclohexyl-4-methylphenol, 2,6-diisopropyl-4-ethylphenol, 2,6-di-tert-amyl-4-methylphenol, 2,6-di-tert-octyl-4-n- propylphenol, 2,6-dicyclohexyl-4-n-octylphenol, 2-isopropyl-4-methyl-6-tert-butylphenol, 2- tert-butyl-4-ethyl-6-tert-octylphenol, 2-isobutyl-4-ethyl-6-tert-hexylphenol, 2-cyclohexyl-4-n- butyl-6-isopropylphenol,
  • Examples of the phosphorus antioxidant include trioctyl phosphite, trilauryl phosphite, tristridecyl phosphite, trisisodecyl phosphite, phenyl diisooctyl phosphite, phenyl diisodecyl phosphite, phenyl di(tridecyl)phosphite, diphenyl isooctyl phosphite, diphenyl isodecyl phosphite, diphenyl tridecyl phosphite, triphenyl phosphite, tris(nonylphenyl)phosphite, tris(2,4-di-tert-butylphenyl)phosphite, tris(butoxyethyl)phosphite, tetratridecyl-4,4′- butylid
  • Dialkyl thiodipropionates and polyhydric alcohol esters of alkylthiopropionic acid are preferably used as sulfur antioxidants.
  • Dialkyl thiodipropionates having an alkyl group of 6 to 20 carbon atoms are preferably used in the present invention.
  • Polyhydric alcohol esters of alkylthiopropionic acid preferably have an alkyl group of 4 to 20 carbon atoms.
  • examples of the polyhydric alcohol for forming the polyhydric alcohol esters include glycerol, trimethylolethane, trimethylolpropane, pentaerythritol, and trishydroxyethyl isocyanurate.
  • dialkyl thiodipropionates examples include dilauryl thiodipropionate, dimyristyl thiodipropionate and distearyl thiodipropionate.
  • polyhydric alcohol esters of alkylthiopropionic acid include glycerol tributylthiopropionate, glycerol trioctylthiopropionate, glycerol trilaurylthiopropionate, glycerol tristearylthiopropionate, trimethylolethane tributylthiopropionate, trimethylolethane trioctylthiopropionate, trimethylolethane trilaurylthiopropionate, trimethylolethane tristearylthiopropionate, pentaerythritol tetrabutylthiopropionate, pentaerythritoltetraoctylthiopropionate, pentaerythrito
  • amine antioxidant examples include bis(2,2,6,6-tetramethyl-4- piperidyl)sebacate, polycondensates of dimethyl succinate and 1-(2-hydroxyethyl)-4-hydroxy- 2,2,6,6-tetramethylpiperidineethanol, N,N′,N′′,N′′′-tetrakis(4,6-bis(butyl-(N-methyl-2,2,6,6- tetramethylpiperidine-4-yl)amino)-triazine-2-yl)-4,7-diazadecane-1,10-diamine, polycondensates of dibutylamine-1,3,5-triazine-N,N′-bis(2,2,6,6-tetramethyl-4-piperdyl)-1,6- hexamethylenediamine and N-(2,2,6,6-tetramethyl-4-piperidyl)butylamine, poly[ ⁇ 6-1,1,3,3- tetramethylbutyl)a
  • Viscosity modifiers are additives that can alter the flow properties of the adhesives described herein.
  • examples of viscosity modifiers include, but are not limited to, natural gums, cellulosics (e.g., hydroxyethyl cellulose, methylcellulose, methyl hydroxypropylmethyl cellulose, sodium carboxymethyl cellulose), alkali-soluble and alkali swellable emulsions (ASE), hydrophobically modified alkali swellable emulsions (HASE), hydrophobically modified ethoxylated urethanes (HEUR), castor oil derivatives, polyamides, calcium sulfonate derivatives, modified polyurea, organoclays and minerals, and polysiloxanes.
  • natural gums e.g., hydroxyethyl cellulose, methylcellulose, methyl hydroxypropylmethyl cellulose, sodium carboxymethyl cellulose
  • ASE alkali-soluble and alkali swellable emulsions
  • thixotropic agents and thickeners include, but are not limited to, compounds such as diethylene glycol, monoalkyl ether, butanone oxime, methyl ethyl ketone oxime, nonylphenol, phenol and cresol; caprolactam, diisopropylamine, 1,2,4-triazole and 3, Examples include amine-containing compounds such as 5-dimethylpyrazole; and aliphatic- containing compounds such as dialkyl malonates.
  • plasticizers include, but are not limited to, dioctyl phthalate or dibutyl phthalate, partially hydrogenated terpenes commercially available as “HB-40”, trioctyl phosphate, epoxy plasticizers, toluene sulfamides, chloroparaffins, adipic acid esters, castor oil, toluene, alkyl phthalates such as alkyl naphthalene, tributyl citrate, acetyl tri-n-butyl citrate (ATBC), polymethylmethacrylate, polydimethyisiloxane, and hexadimethylsilazane.
  • HB-40 partially hydrogenated terpenes
  • trioctyl phosphate epoxy plasticizers
  • toluene sulfamides chloroparaffins
  • adipic acid esters castor oil
  • alkyl phthalates such as alkyl naphthalene, tributyl cit
  • suitable plasticizers include, but are not limited to, a fatty acid ester or a phosphate ester having 8 to 30 carbon atoms.
  • fatty acid esters having 8 to 30 carbon atoms include esters of mono- or polybasic acids having 6 to 18 carbon atoms and branched alcohols having 18 or less carbon atoms, unsaturated fatty acids or branching acids having 14 to 18 carbon atoms and tetravalent acids.
  • H Docket: 222105-2320 the ester of a mono- or poly-acid having 6 to 18 carbons and a branched alcohol having 18 or less carbon include, for example, isostearyl laurate, isopropyl myristate, isocetyl myristate, Octyldodecyl myristate, isostearyl palmitate, isocetyl stearate, octyldodecyl oleate, diisostearyl adipate, diisosuccinate Cetyl ester, triolenylidene trimellitate, and triisocetyl trimellitate.
  • the following compounds are exemplified as the unsaturated fatty acid having 14 to 18 carbon atoms or an ester of a branched acid and an alcohol having a tetravalent or lower value, and the unsaturated fatty acid having 14 to 18 carbon atoms and a branching acid and an alcohol having a tetravalent or less are exemplified below.
  • unsaturated fatty acids or branched acids having 14 to 18 carbon atoms include myristic oleic acid, oleic acid, linoleic acid, hypolinolenic acid, isopalmitic acid, and isostearic acid.
  • Examples of the alcohol having a tetravalent or lower value include ethylene glycol, propylene glycol, glycerin, trimethylolpropane, pentaerythritol, and sorbitan.
  • Examples of the ester of a mono- or poly- acid having 6 to 18 carbon atoms and a polyalkylene glycol include dihexyl acid polyethylene glycol, di-2-ethylhexyl acid polyethylene glycol, and dilauric acid polyethylene. Ethylene glycol, polyethylene glycol dioleate, and diethylene glycol methyl ether adipic acid.
  • fatty acid esters obtained by epoxidizing unsaturated sites with peroxide and the like include epoxidized fats such as epoxidized soybean oil, epoxidized linseed oil, and epoxidized cottonseed oil, and unsaturated unsaturated carbons of 8 to 18.
  • epoxidized fats such as epoxidized soybean oil, epoxidized linseed oil, and epoxidized cottonseed oil
  • the phosphoric acid ester include phosphorous acid or phosphoric acid, and an ester compound with a linear or branched alcohol having 2 to 18 carbon atoms.
  • tackifiers include, but are not limited to, terpene resins such as polyterpenes (e.g., ⁇ -pinene resins, ⁇ -pinene resins, and limonene resins) and aromatic- modified polyterpene resins (e,g, phenol-modified polyterpene resins), kumaraninden resins, and petroleum resins such as C5 hydrocarbon resins, C9 hydrocarbon resins, C5 / C9 hydrocarbon resins, and dicyclopentadiene resins.
  • terpene resins such as polyterpenes (e.g., ⁇ -pinene resins, ⁇ -pinene resins, and limonene resins) and aromatic- modified polyterpene resins (e,g, phenol-modified polyterpene resins), kumaraninden resins, and petroleum resins such as C5 hydrocarbon resins, C9 hydrocarbon resins, C5 / C9 hydrocarbon resins, and di
  • These raw materials include aliphatic hydrocarbons (mainly a mixture of trans-1,3-pentadiene, cis-1,3-pentadiene, 2- methyl-2-butene, dicyclopentadiene, cyclopentadiene, and cyclopentene, and the like.
  • aliphatic hydrocarbons mainly a mixture of trans-1,3-pentadiene, cis-1,3-pentadiene, 2- methyl-2-butene, dicyclopentadiene, cyclopentadiene, and cyclopentene, and the like.
  • aromatic hydrocarbons mainly a mixture of vinyltoluene, dicyclopentadiene, inden, methylstyrene, styrene, and methylindene.
  • C9 monomer with presence or a mixture thereof.
  • the tackifier derived from the C5 monomer is called a C5 hydrocarbon resin
  • the tackifier derived from the C9 monomer is called a C9 hydrocarbon resin.
  • H Docket: 222105-2320 are derived from a mixture of C5 and C9 monomers, or from a blend of a C5- hydrocarbon tackifier and a C9-hydrocarbon tackifier. These tackifiers are sometimes referred to as C5 / C9 hydrocarbon tackifiers. Any of these resins can be partially or completely hydrogenated to improve their color, their thermal stability, or their process compatibility.
  • suitable hardeners include, but are not limited to, an isocyanate hardener, an epoxy hardener, a melamine hardener, a carbodiimide hardener, an oxazoline hardener, an aziridine hardener, and the like.
  • suitable waxes include, but are not limited to palm, soy, canola, areca, beeswax and other vegetable and animal waxes, with a preference for carnauba palm waxes.
  • the adhesives described herein are pressure sensitive adhesives.
  • the adhesives described herein do not harden in response to evaporation of a solvent, or upon reaction with UV radiation, or due to a chemical reaction, or due to cooling. Instead, the adhesive may form a bond when light pressure is applied to marry the adhesive to an adherend. Without being bound by theory, it is believed that the bond forms because the adhesive is soft enough to flow or wet the adherend, but hard enough to resist flow when stress is applied to the bond. Once the adhesive and adherend are in proximity to one another, molecular interactions such as van der Waals forces may also contribute to the bond strength. [70] In another aspect, the adhesives described herein do not require that the surface of the adherent include an adhesive.
  • the adhesive when the adhesive is placed in proximity with the surface of the adherend, the surface of the adherend is free of the adhesive.
  • the adhesives described herein may be permanent or removable.
  • the adhesive is removable if removal of the adhesive from the adherend does not result in removal of material forming the surface of the adherend.
  • removing the substrate may remove a large proportion or substantially all of the adhesive from the surface of the adherend.
  • the adhesive may be repositionable, meaning that, after being bonded once to an adherend, it retains sufficient tack to be re-adhered to the same adherent in a different position or to a different adherend.
  • the adhesives described herein can be applied to numerous substrates and articles using techniques known in the art.
  • the adhesives described herein can be applied to labels. Labels are used in numerous applications, and the adhesives described herein provide an environmentally-favorable alternative.
  • the label is a produce label that is applied to raw fruit and vegetables.
  • the label with the adhesive described herein can be used to apply to food packages such as for meat, poultry, fish, and T
  • the adhesives described herein can be applied to the label using techniques known in the art including spraying or rolling the adhesive to at least one surface of the label.
  • the label can be applied to an automotive component.
  • the label can be applied to the windshield of a car, truck, boat, airplane and the like.
  • the adhesives described herein can be used to manufacture a tape.
  • the tape is a pressure-sensitive tape.
  • the tape can be manufactured and used independently or, in the alternative, the tape can be a component of another article.
  • the tape is a component of a diaper for children and adults.
  • the adhesives described herein can be used to produce sticky notes and other paper products where it is desirable to apply an adhesive such as, for example, a pressure sensitive adhesive.
  • the adhesives described herein can be used to produce cold seal packages where it is desirable to apply an adhesive where it is undesirable to apply heat or minimal heat (e.g., 25 o C to 35 o C).
  • cold seal packaging is useful in packaging protein bars and other food products where it is undesirable to apply heat.
  • the adhesive described herein can be used to mark or label a package such as, for example, a food storage package.
  • the method comprises applying an adhesive label to at least one surface of the package, wherein the adhesive label has at least one surface coated with an adhesive described herein.
  • the method comprises (a) applying an adhesive described herein to at least one surface of the package and (b) applying a label to the adhesive on the at least one surface of the package.
  • Aspect 1 An adhesive comprising a polyester, wherein the polyester has a glass transition temperature of less than 25 o C and a crystallinity of less than 10%.
  • Aspect 2. The adhesive of Aspect 1, wherein the polyester comprises a plurality of residues of a diol comprising one or more C3 to C20 aliphatic diols and one or more C3 to C20 aliphatic dicarboxylic acids.
  • Aspect 1 The adhesive of Aspect 1, wherein the polyester comprises a plurality of residues of a hydroxyl carboxylic acid compound.
  • Aspect 4. The adhesive of Aspect 3, wherein the hydroxyl carboxylic acid compound comprises an omega hydroxy acid.
  • Aspect 5 The adhesive of Aspect 3, wherein the hydroxyl carboxylic acid compound comprises lactic acid, glycolic acid, 3-hydroxypropionic acid, caproic acid, and any combination thereof. T
  • Aspect 1 The adhesive of Aspect 1, wherein the polyester comprises a plurality of residues of a lactone.
  • Aspect 7. The adhesive of Aspect 6, wherein the lactone is a C3 to C8 aliphatic lactone.
  • Aspect 6 wherein the lactone comprises lactide, caprolactone, butyrolactone, or any combination thereof.
  • Aspect 9 The adhesive of Aspect 1, wherein the polyester comprises a plurality of residues of a diol selected from the group consisting of 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and any combination thereof; and a plurality of residues of a dicarboxylic acid selected from the group consisting of succinic acid, adipic acid, pimelic acid, suberic acid, glutaric acid, and any combination thereof.
  • Aspect 10 Aspect 10.
  • the adhesive of Aspect 1 wherein the polyester comprises a plurality of residues of a diol selected from the group consisting of 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and any combination thereof; a plurality of residues of a first dicarboxylic acid selected from the group consisting of succinic acid, adipic acid, pimelic acid, suberic acid, and any combination thereof; and a plurality of residues of a second dicarboxylic comprising glutaric acid.
  • Aspect 11 The adhesive of Aspect 9 or 10, wherein the diol is 1,4-butanediol.
  • Aspect 12 The adhesive of Aspect 9 or 10, wherein the diol is a combination of 1,3- propanediol and 1,4-butanediol.
  • Aspect 13 The adhesive of Aspect 12, wherein the molar ratio of the 1,4-butanediol to 1,3-propanediol is from 4:1 to 7:1.
  • Aspect 14 The adhesive of any one of Aspects 10-13, wherein the molar ratio of the first dicarboxylic acid to the second dicarboxylic acid is from 1:1 to 1:5.
  • Aspect 15 The adhesive of any one of Aspects 10-14, wherein the second dicarboxylic acid consists of glutaric acid. [93] Aspect 16.
  • Aspect 17 The adhesive of any one of Aspects 9-15, wherein the polyester further comprises a plurality of residues of a sugar.
  • Aspect 18 The adhesive of any one of Aspects 1-17, wherein the polyester further comprises a plurality of residues of a sugar. T
  • Aspect 21 The adhesive of any one of Aspects 17-19, wherein the sugar is a sorbitan or a fatty acid derivative thereof.
  • Aspect 21 The adhesive of any one of Aspects 17-20, wherein the sugar is sorbitan monooleate, sorbitan monolaurate, sorbitan monostearate, sorbitan monopalmitate, sorbitan, fructose, mannose, xylose, or any combination thereof.
  • Aspect 22 The adhesive of Aspect 1, wherein polyester comprises a plurality of residues of 1,4-butanediol, a plurality of residues of glutaric acid, and a plurality of residues of succinic acid.
  • Aspect 23 The adhesive of Aspect 1, wherein polyester comprises a plurality of residues of 1,4-butanediol, a plurality of residues of glutaric acid, and a plurality of residues of succinic acid.
  • polyester further comprises a plurality of residues of 1,3-propanediol.
  • Aspect 24 The adhesive of Aspect 22 or 23, wherein polyester further comprises a plurality of residues of sugar, wherein the sugar is a fatty acid derivative of sorbitan.
  • Aspect 25 The adhesive of Aspect 24, wherein the sugar is sorbitan monooleate, sorbitan monolaurate, sorbitan monostearate, sorbitan monopalmitate, sorbitan, fructose, mannose, xylose, or any combination thereof.
  • Aspect 26 Aspect 26.
  • Aspect 27 The adhesive of Aspect 1, wherein the polyester comprises a plurality of residues of 1,4-butanediol and 1,3-propanediol, succinic acid, glutaric acid, and sorbitan monooleate.
  • Aspect 29 The adhesive of any one of Aspects 1-27, wherein the polyester has a glass transition temperature of about -80 o C to less than 25 o C.
  • Aspect 29 The adhesive of any one of Aspects 1-28, wherein the polyester has a crystallinity of about 1% to less than 5%.
  • Aspect 30 The adhesive of any one of Aspects 1-29, wherein the polyester is compostable. T
  • Aspect 32 The adhesive of any one of Aspects 1-29, wherein the polyester is ocean compostable. [110] Aspect 33.
  • Aspect 34 The adhesive of any one of Aspects 1-33, wherein the adhesive is a pressure sensitive adhesive.
  • Aspect 35 The adhesive of any one of Aspects 1-34, wherein the polyester is from about 50 weight percent to about 100 weight percent of the adhesive.
  • Aspect 36 The adhesive of any one of Aspects 1-35, wherein the adhesive further comprises a UV absorber, an antioxidant, a viscosity modifier, a thixotropic agent, a hardener, a wax, a tackifier, a plasticizer, or any combination thereof.
  • Aspect 37 Aspect 37.
  • Aspect 40 A label comprising the adhesive of any one of Aspects 1-39.
  • Aspect 41 The label of Aspect 40, wherein the label comprises a produce label, a food packaging label, an automotive component sticker.
  • Aspect 42 A package comprising a label adhered to the package with the adhesive of any one of Aspects 1-39.
  • Aspect 43 The package of Aspect 42, wherein the package stores food.
  • Aspect 44 A tape comprising the adhesive of any one of Aspects 1-39.
  • Aspect 45 The tape of Aspect 44, wherein the tape is a component of a diaper.
  • Aspect 46 A sticky note comprising the adhesive of any one of Aspects 1-39.
  • Aspect 47 A cold seal package comprising the adhesive of any one of Aspects 1-39.
  • Aspect 48. A polyester having a glass transition temperature of less than 25 o C and a crystallinity of less than 10%. [126] Aspect 49.
  • the polyester of Aspect 48 wherein the polyester comprises a plurality of residues of a diol comprising one or more C3 to C20 aliphatic diols and one or more C3 to C20 aliphatic dicarboxylic acids. T
  • the polyester of Aspect 48 wherein the polyester comprises a plurality of residues of a hydroxyl carboxylic acid compound.
  • Aspect 51 The polyester of Aspect 50, wherein the hydroxyl carboxylic acid compound comprises an omega hydroxy acid.
  • Aspect 52 wherein the hydroxyl carboxylic acid compound comprises an omega hydroxy acid.
  • the polyester of Aspect 50 wherein the hydroxyl carboxylic acid compound comprises lactic acid, glycolic acid, 3-hydroxypropionic acid, caproic acid, and any combination thereof.
  • Aspect 53 The polyester of Aspect 48, wherein the polyester comprises a plurality of residues of a lactone.
  • Aspect 54 The polyester of Aspect 53, wherein the lactone is a C3 to C8 aliphatic lactone.
  • Aspect 55 The polyester of Aspect 53, wherein the lactone comprises lactide, caprolactone, butyrolactone, or any combination thereof.
  • the polyester of Aspect 48 wherein the polyester comprises a plurality of residues of a diol selected from the group consisting of 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and any combination thereof; and a plurality of residues of a dicarboxylic acid selected from the group consisting of succinic acid, adipic acid, pimelic acid, suberic acid, glutaric acid, and any combination thereof.
  • a diol selected from the group consisting of 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and any combination thereof
  • a dicarboxylic acid selected from the group consisting of succinic acid, adipic acid, pimelic acid, suberic acid, glutaric acid, and any combination thereof.
  • the polyester of Aspect 48 wherein the polyester comprises a plurality of residues of a diol selected from the group consisting of 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and any combination thereof; a plurality of residues of a first dicarboxylic acid selected from the group consisting of succinic acid, adipic acid, pimelic acid, suberic acid, and any combination thereof; and a plurality of residues of a second dicarboxylic comprising glutaric acid. [135] Aspect 58.
  • Aspect 56 or 57 wherein the diol is 1,4-butanediol.
  • Aspect 59 The polyester of Aspect 56 or 57, wherein the diol is a combination of 1,3- propanediol and 1,4-butanediol.
  • Aspect 60 The polyester of Aspect 49, wherein the molar ratio of the 1,4-butanediol to 1,3-propanediol is from 4:1 to 7:1.
  • Aspect 61 The polyester of any one of Aspects 57-60, wherein the molar ratio of the first dicarboxylic acid to the second dicarboxylic acid is from 1:1 to 1:5.
  • Aspect 62 The polyester of any one of Aspects 57-60, wherein the molar ratio of the first dicarboxylic acid to the second dicarboxylic acid is from 1:1 to 1:5.
  • Aspect 63 The polyester of any one of Aspects 57-61, wherein the second dicarboxylic acid consists of glutaric acid. T
  • Aspect 65 wherein the sugar is present in an amount of a greater than 0 mole percent to 15 mole percent hydroxyl content.
  • Aspect 67 The polyester of any one of Aspects 64-66, wherein the sugar is a sorbitan or a fatty acid derivative thereof.
  • Aspect 68 The polyester of any one of Aspects 64-67, wherein the sugar is sorbitan monooleate, sorbitan monolaurate, sorbitan monostearate, sorbitan monopalmitate, sorbitan, fructose, mannose, xylose, or any combination thereof.
  • Aspect 69 Aspect 69.
  • polyester of Aspect 48 wherein polyester comprises a plurality of residues of 1,4-butanediol, a plurality of residues of glutaric acid, and a plurality of residues of succinic acid.
  • Aspect 70 The polyester of Aspect 69, wherein polyester further comprises a plurality of residues of 1,3-propanediol.
  • Aspect 71 The polyester of Aspect 69 or 70, wherein polyester further comprises a plurality of residues of sugar, wherein the sugar is a fatty acid derivative of sorbitan.
  • the polyester of Aspect 71 wherein the sugar is sorbitan monooleate, sorbitan monolaurate, sorbitan monostearate, sorbitan monopalmitate, sorbitan, fructose, mannose, xylose, or any combination thereof.
  • Aspect 73 The polyester of Aspect 48, wherein the polyester comprises a plurality of residues of 1,4-butanediol and 1,3-propanediol, succinic acid, glutaric acid, and sorbitan monooleate.
  • the polyester of Aspect 48 wherein the polyester comprises a plurality of residues of 1,4-butanediol and 1,3-propanediol, succinic acid, glutaric acid, and sorbitan monooleate, wherein the molar ratio of the 1,4-butanediol to 1,3-propanediol is from 4:1 to 7:1; the molar ratio of the first dicarboxylic acid to the second dicarboxylic acid is from 1:1 to 1:5 and the molar ratio of the sum of the first dicarboxylic acid and the second dicarboxylic acid to the diol is from 1:10 to 1:1.
  • H Docket: 222105-2320 [152] Aspect 75 Aspect 75.
  • Aspect 76 The polyester of any one of Aspects 48-74, wherein the polyester has a glass transition temperature of about -80 o C to less than 25 o C.
  • Aspect 76 The polyester of any one of Aspects 48-75, wherein the polyester has a crystallinity of about 1% to less than 5%.
  • Aspect 77 The polyester of any one of Aspects 48-76, wherein the polyester comprising the reaction product of one or more diols and one or more dicarboxylic acids, wherein the polyester has a glass transition temperature of less than 25 o C and a crystallinity of less than 10%.
  • Aspect 78 The polyester of any one of Aspects 48-76, wherein the polyester comprising the reaction product of one or more diols and one or more dicarboxylic acids, wherein the polyester has a glass transition temperature of less than 25 o C and a crystallinity of less than 10%.
  • a method for making an adhesive label comprising applying the adhesive of any one of Aspects 1-39 to at least one surface of the label.
  • Aspect 80. A method for labeling a package, the method comprising applying an adhesive label to at least one surface of the package, wherein the adhesive label has at least one surface coated with the adhesive of any one of Aspects 1-39.
  • Aspect 81. A method for labeling a package, the method comprising (a) applying an adhesive of any one of Aspects 1-39 to at least one surface of the package and (b) applying a label to the adhesive on the at least one surface of the package.
  • Aspect 82 The method of Aspect 80 or 81, wherein the package is for storing food.
  • EXAMPLES [160] Now having described the embodiments of the disclosure, in general, the examples describe some additional embodiments. While embodiments of the present disclosure are described in connection with the example and the corresponding text and figures, there is no intent to limit embodiments of the disclosure to these descriptions. On the contrary, the intent is to cover all alternatives, modifications, and equivalents included within the spirit and scope of embodiments of the present disclosure.
  • a lewis acid transesterification catalyst is added, preferably zirconium n-butoxide (other catalysts may be used).
  • a vacuum is then slowly applied to the reaction and the temperature is increased to 210 o C. The reaction is allowed to continue until the determined rheological properties are achieved (4-12 hrs).
  • Differential Scanning Calorimetry [164] Approximately 10mg of material is weighed into an aluminum sample pan and analyzed. The sample was then heated at 10 o C/min to 120 o C. The sample was then cooled to -60 o C at 10C/min and then held isothermally for 30 minutes. The sample was then heated to 120C at 10C/min.
  • the thermal transitions including melting point and glass transition temperature was determined from the second heating curve. Differential scanning calorimetry is completed to determine the thermal properties of the adhesive including melting temperature, degree of crystallinity, and glass transition temperature.
  • Adhesive Testing [166] Each adhesive sample was laminated to a face film and silicone release liner using a hot melt blade coater with an application temperature between 350F and 400F. The thickness of the adhesive film applied was varied based upon application demand. [167] 90 Peel and Loop Tack Testing [168] 90 peel was determined using ASTMD6862-11 and loop tack testing was determined by ASTM6195-03. [169] Rheological Properties [170] Rheological properties of the pressure sensitive adhesive are measured on parallel plate rheometer.
  • respiration of the inoculum generated between 50 and 150 milligrams of CO 2 per day per 1 gram of volatile solids over ten days at 58°C.
  • the resulting inoculum was sieved to less than 10 mm and used for experiments at 21 ⁇ 1°C.
  • the inoculum was found to have an ash content of less than 70%, a pH between 7.0 and 8.2, and a water content between 45% and 50% at the time of pre-testing.
  • the inoculum was analyzed for the concentrations of various metals through total acid digestion. Polymer and compositions were examined at 21 ⁇ 1°C until both the samples and cellulose control mineralized completely (>90% and with a plateau in absolute biodegradation).
  • the crosslinked polyester is produced through polycondensation and transesterification reactions.
  • the monomers employed include a specific ratio of succinic acid, glutaric acid, 1,3 propanediol and 1,4 butanediol. Altering the monomer concentration alters the thermal and mechanical properties of the resulting polymer. For example, increasing the succinic acid concentration increases the crystallinity of the polymer leading to poor adhesive properties while also reducing the overall compostability of the polymer. Increasing or decreasing the 1,3 propanediol content alters the melting temperature of the polymer resulting in crystallization within the adhesive application temperature range (0 o C – 45 o C) leading to unwanted debonding from target substrates.
  • FIG.1 provides a synthetic scheme for producing a copolyester useful herein.
  • the crosslinked polyester was deliberately synthesized to meet the demand for a home compostable PSA.
  • the standard for home compostability is not defined within the ASTM standards in the USA, but is outlined in AS 5810/EN 17427. Following the standard conditions, respirometry analysis was conducted during which the mineralization of all organic carbon within the polymeric material into CO 2 can be measured in a controlled environment.
  • the home composting measurements were conducted in locally sourced compost at a controlled temperature of 21 o C. To meet the home compostable standard, over 90% of the total organic T
  • the viscoelastic properties of a polymer directly relate to the materials ability to function as an adhesive. It has been shown that a material with a storage modulus less than 0.3 MPa at 1Hz has the appropriate elastic and viscous properties to be a pressure sensitive adhesive. The polymeric system we formulated meets this baseline (FIG.3).
  • the adhesive properties of the polymeric material developed was measured following the ASTM D6195 standard for loop tack testing.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention concerne des adhésifs composés d'un polyester. Selon un aspect, le polyester décrit dans la description est compostable et les adhésifs décrits dans la description présentent une applicabilité commerciale largement répandue en tant qu'alternative compostable aux adhésifs non biodégradables actuels. Les polyesters décrits dans la description sont appropriés pour être utilisés dans divers adhésifs, tels que, par exemple, des adhésifs sensibles à la pression, comprenant des adhésifs sensibles à la pression compostables. Selon un aspect, le polyester divulgué dans la description fournit à la fois une adhérence et une pégosité, permettant à des adhésifs sensibles à la pression d'être formulés sans ajout d'agent poisseux séparé.
PCT/US2025/023371 2024-04-08 2025-04-07 Adhésifs et procédés pour leur fabrication et leur utilisation Pending WO2025217010A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202463575913P 2024-04-08 2024-04-08
US63/575,913 2024-04-08

Publications (1)

Publication Number Publication Date
WO2025217010A1 true WO2025217010A1 (fr) 2025-10-16

Family

ID=97350794

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2025/023371 Pending WO2025217010A1 (fr) 2024-04-08 2025-04-07 Adhésifs et procédés pour leur fabrication et leur utilisation

Country Status (1)

Country Link
WO (1) WO2025217010A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050171250A1 (en) * 2004-01-30 2005-08-04 Hayes Richard A. Aliphatic-aromatic polyesters, and articles made therefrom
US20080142023A1 (en) * 2006-12-11 2008-06-19 3M Innovative Properties Company Biocompatible antimicrobial compositions
US20100330315A1 (en) * 2008-02-14 2010-12-30 Bostik Sa Projet hot melt compostable
US20160280847A1 (en) * 2013-11-18 2016-09-29 Tesa Se Novel Polyester Suitable for Producing Carrier Materials for Adhesive Tapes
US20180171071A1 (en) * 2005-04-22 2018-06-21 Mitsubishi Chemical Corporation Biomass-resource-derived polyester and production process thereof
US20230065649A1 (en) * 2021-08-12 2023-03-02 Eastman Chemical Company Articles with recycle content having enduring physical properties comparable to virgin
US20230167225A1 (en) * 2020-04-27 2023-06-01 The Regents Of The University Of California Degradable bio-based polymers
US12146080B1 (en) * 2024-04-08 2024-11-19 University Of Georgia Research Foundation, Inc. Home compostable adhesives and methods for making and using the same

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050171250A1 (en) * 2004-01-30 2005-08-04 Hayes Richard A. Aliphatic-aromatic polyesters, and articles made therefrom
US20180171071A1 (en) * 2005-04-22 2018-06-21 Mitsubishi Chemical Corporation Biomass-resource-derived polyester and production process thereof
US20080142023A1 (en) * 2006-12-11 2008-06-19 3M Innovative Properties Company Biocompatible antimicrobial compositions
US20100330315A1 (en) * 2008-02-14 2010-12-30 Bostik Sa Projet hot melt compostable
US20160280847A1 (en) * 2013-11-18 2016-09-29 Tesa Se Novel Polyester Suitable for Producing Carrier Materials for Adhesive Tapes
US20230167225A1 (en) * 2020-04-27 2023-06-01 The Regents Of The University Of California Degradable bio-based polymers
US20230065649A1 (en) * 2021-08-12 2023-03-02 Eastman Chemical Company Articles with recycle content having enduring physical properties comparable to virgin
US12146080B1 (en) * 2024-04-08 2024-11-19 University Of Georgia Research Foundation, Inc. Home compostable adhesives and methods for making and using the same

Similar Documents

Publication Publication Date Title
US20250313734A1 (en) Home compostable adhesives and methods for making and using the same
AU689130B2 (en) Biodegradable/compostable hot melt adhesives comprising polyester of lactic acid
CN106574036B (zh) 聚酯聚氨酯
EP2311896B1 (fr) Polyesters, compositions de polyesters, compositions adhésives, couches adhésives et feuilles adhésives
US8962136B2 (en) Pressure-sensitive adhesive sheet for surface protection
EP2826833B1 (fr) Composition adhésive et feuille adhésive
EP2492326B1 (fr) Feuille adhésive sensible à la pression de type à retrait par durcissement par rayonnement
CN102597151B (zh) 粘合剂组合物
US20120208955A1 (en) Double-sided pressure-sensitive adhesive sheet
EP1928969B1 (fr) Adhesifs thermofusibles a base de polyester-amide
US20170362478A1 (en) Biodegradable pressure-sensitive adhesive
EP2826832B1 (fr) Composition adhésive et feuille adhésive
US20100016543A1 (en) Crystalline copolyesters having high solubility in non-halogenated solvents, and their use
US10626309B2 (en) Biodegradable, pressure-sensitive adhesive based on polyester-polyurethane
CN106459694A (zh) 用于保护表面的胶带
EP2492327A1 (fr) Ruban adhésif sensible à la pression pour masquage
JP2016098323A (ja) 接着剤、及び該接着層を有する多層フィルム
EP3089868B1 (fr) Films compostables et étiquettes compostables
JP2013203946A (ja) ポリエステル樹脂およびそれを含むドライラミネート用接着剤
KR101433809B1 (ko) 용제형 접착제용 생분해성 폴리에스테르 조성물, 폴리에스테르 수지, 이를 포함하는 용제형 접착제, 및 이의 제조 방법
WO2025217010A1 (fr) Adhésifs et procédés pour leur fabrication et leur utilisation
KR20250166134A (ko) 점착제, 점착제의 제조 방법 및 점착 시트
EP4386061A1 (fr) Adhésif sensible à la pression à base de polyhydroxyalcanoate
EP4466322B1 (fr) Adhésif thermofusible, procédé de préparation et utilisations de celui-ci
EP4497797A1 (fr) Composition adhésive sensible à la pression à base de polyester, adhésif sensible à la pression à base de polyester, feuille adhésive sensible à la pression, film décoratif, film pour élément électronique et objet moulé décoratif

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 25786667

Country of ref document: EP

Kind code of ref document: A1