WO2024012694A1 - Composés aromatiques et polymères fabriqués à partir de ceux-ci - Google Patents

Composés aromatiques et polymères fabriqués à partir de ceux-ci Download PDF

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Publication number
WO2024012694A1
WO2024012694A1 PCT/EP2022/069887 EP2022069887W WO2024012694A1 WO 2024012694 A1 WO2024012694 A1 WO 2024012694A1 EP 2022069887 W EP2022069887 W EP 2022069887W WO 2024012694 A1 WO2024012694 A1 WO 2024012694A1
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WIPO (PCT)
Prior art keywords
compound
component
polymer
formula
group
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PCT/EP2022/069887
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English (en)
Inventor
Ryan MONDSCHEIN
Joel POLLINO
Kermit S. Kwan
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Solvay Specialty Polymers Usa, Llc
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Priority to PCT/EP2022/069887 priority Critical patent/WO2024012694A1/fr
Publication of WO2024012694A1 publication Critical patent/WO2024012694A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F122/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F122/04—Anhydrides, e.g. cyclic anhydrides
    • C08F122/06—Maleic anhydride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate

Definitions

  • This application is a provisional application.
  • the present disclosure relates to new aromatic monomers suitable for use in the production of useful polymers.
  • Such monomer compounds comprise versatile functionality that enable the synthesis of useful polymers in various forms and by multiple processing techniques.
  • the reaction of these new molecules with various difunctional comonomers can produce thermoplastic-like linear or branched polymers while homopolymerization or polymerization with multifunctional comonomers can produced crosslinked thermoset structures.
  • thermoplastic and thermoset materials find applications in many industries, including the aviation, automotive, and marine industries. Such materials also find applications in the areas of health, medicine, and biotechnology, which is a rapidly developing domain based largely on known materials but moving to designed and engineered polymers, as well as information and communications, which is an emerging field for polymers significantly based on their electronic properties.
  • Articles and parts comprising polymeric materials are made by a variety of manufacturing processes, including, for example, extrusion, injection molding, thermoforming, liquid resin casting, additive manufacturing, such as 3D printing, and the like.
  • manufacturing processes including, for example, extrusion, injection molding, thermoforming, liquid resin casting, additive manufacturing, such as 3D printing, and the like.
  • challenges in the manufacturing of polymeric articles and parts For example, one such challenge is that the nature of the polymeric material and the process used to manufacture articles and parts from it must be considered, as heating causes expansion, and the following cooling process can cause shrinkage and warping. These phenomena can affect the strength and integrity of the final product.
  • Such features must also be balanced with the properties required for the product being made, such as mechanical and electrical properties, to name a few.
  • the present disclosure relates to a compound represented by formula I: wherein
  • Ar is a C10-C14 arylene group
  • A1 and A2 are each, independently, -(CH2)n-, wherein each occurrence of n is an integer from 1 to 12, and
  • R’ and R are each, independently, a moiety selected from the group consisting of acrylate, methacrylate, maleimide, acrylamide, and vinyl sulfone; with the proviso that when Ar is a biphenylene group and R’ and R” are each acrylate or methacrylate, n is an integer from 5 to 12.
  • the present disclosure relates to a process for producing the compound described herein, the process comprising: reacting a compound represented by formula II: wherein Ar is a C10-C14 arylene group; with a compound represented by formula III:
  • HO-A2-R (IV), wherein A1 and A2 are each, independently, -(CH2)n-, wherein each occurrence of n is an integer from 1 to 12, and
  • R’ and R are each, independently, a moiety selected from the group consisting of acrylate, methacrylate, maleimide, acrylamide, and vinyl sulfone; with the proviso that when Ar is a biphenylene group and R’ and R” are each acrylate or methacrylate, n is an integer from 5 to 12.
  • the present disclosure relates to a polymer comprising a repeating unit derived from the compound described herein or derived from the compound produced by the process described herein.
  • the present disclosure relates to a process for producing a polymer described herein, the process comprising reacting the compound described herein or the compound produced by the process described herein with a compound comprising one or more, typically two or more, thiol or amine groups, with a compound comprising one or more acrylate or methacrylate groups, with a compound comprising one or more vinyl ether groups, or with a compound comprising one or more maleimide groups.
  • the present disclosure relates to an article comprising the polymer described herein or polymer produced according to a process described herein.
  • the terms “a”, “an”, or “the” means “one or more” or “at least one” and may be used interchangeably, unless otherwise stated.
  • the term “comprises” includes “consists essentially of” and “consists of.”
  • the term “comprising” includes “consisting essentially of” and “consisting of.”
  • the term “about” or “approximately” means an acceptable error for a particular value as determined by one of ordinary skill in the art, which depends in part on how the value is measured or determined.
  • the term “about” or “approximately” means within 1 , 2, 3, or 4 standard deviations. In certain embodiments, the term “about” or “approximately” means within 50%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0.05% of a given value or range. Also, it should be understood that any numerical range recited herein is intended to include all sub-ranges subsumed therein.
  • a range of “1 to 10” is intended to include all sub-ranges between and including the recited minimum value of 1 and the recited maximum value of 10; that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10. Because the disclosed numerical ranges are continuous, they include every value between the minimum and maximum values. Unless expressly indicated otherwise, the various numerical ranges specified in this application are approximations.
  • (Cx-Cy) or “Cx-Cy” in reference to an organic group, wherein x and y are each integers, means that the group may contain from x carbon atoms to y carbon atoms per group.
  • aryl means cyclic, coplanar 5- or 6-membered organic group having a delocalized, conjugated IT system, with a number of IT electrons that is equal to 4n+2, where n is 0 or a positive integer, including compounds where each of the ring members is a carbon atom, such as benzene or biphenyl, compounds where one or more of the ring members is a heteroatom, typically selected from oxygen, nitrogen and sulfur atoms, such as furan, pyridine, imidazole, and thiophene, and fused ring systems, such as naphthalene, anthracene, and phenanthrene, wherein one or more of the ring carbons may be substituted with one or more organic groups, typically selected from alkyl, alkoxyl, hydroxyalkyl, cycloalkyl, alkoxyalkyl, haloalkyl, aryl, alkaryl, and aralkyl.
  • radicals described herein may be bivalent, i.e. , two hydrogen atoms may be replaced by chemical bonds. Such groups are often modified by an “-ene” ending herein.
  • alkylene means an alkyl radical with an additional hydrogen replaced by a chemical bond.
  • arylene means an aryl radical with an additional hydrogen replaced by a chemical bond.
  • aromatic means that the organic compound that comprises one or more one aryl moieties, which may each optionally be interrupted by one or more heteroatoms, typically selected from oxygen, nitrogen, and sulfur heteroatoms, and one or more of the carbon atoms of one or more one aryl moieties may optionally be substituted with one or more organic groups, typically selected from alkyl, alkoxyl, hydroxyalkyl, cycloalkyl, alkoxyalkyl, haloalkyl, aryl, alkaryl, and aralkyl.
  • Any substituent or radical described herein may optionally be substituted at one or more carbon atoms with one or more, same or different, substituents described herein.
  • an aryl group may be further substituted with another aryl group or an alkyl group.
  • Any substituent or radical described herein may also optionally be substituted at one or more carbon atoms with one or more substituents selected from the group consisting of halogen, such as, for example, F, Cl, Br, and I; nitro (NO2), cyano (CN), and hydroxy (OH).
  • the present disclosure relates to a compound represented by formula I: wherein
  • Ar is a C10-C14 arylene group
  • A1 and A2 are each, independently, -(CH2)n-, wherein each occurrence of n is an integer from 1 to 12, and
  • R’ and R are each, independently, a moiety selected from the group consisting of acrylate, methacrylate, maleimide, acrylamide, and vinyl sulfone; with the proviso that when Ar is a biphenylene group and R’ and R” are each acrylate or methacrylate, n is an integer from 5 to 12.
  • Ar is a C10-C14 arylene group.
  • Suitable C10-C14 arylene groups include, but are not limited to, those derived from benzene, biphenyl, naphthalene, anthracene, and phenanthrene.
  • the two bonds connecting the carbonyl carbons to Ar are not limited and may be on the same ring or on different rings.
  • Ar is selected from the group consisting of: a
  • Ar is selected from the group consisting of:
  • Ai and A2 provide alkylene functionalities that act as flexible spacers in polymers made from the compound of formula I.
  • A1 and A2 are each, independently, -(CH2)n-, wherein each occurrence of n is an integer from 1 to 12.
  • A1 and A2 are unsubstituted.
  • A1 and A2 are identical and n is an integer from 2 to 4. In one embodiment, A1 and A2 are unsubstituted, identical, and n is an integer from 2 to 4.
  • R’ and R provide the reactive functionality required for producing polymers from the compound of formula I.
  • Suitable reactive moieties are moieties comprising an alkene adjacent to a carbonyl or sulfone group.
  • R’ and R are each, independently, a moiety selected from the group consisting of acrylate, methacrylate, maleimide, acrylamide, and vinyl sulfone.
  • R’ and R are each, independently, wherein Ri, R2, R3, R4, Rs, Re, R7, Rs, R9, R10, R11, and R12 are each, independently, H or CH3.
  • R’ and R” are each
  • Ri is H or CH3, typically H, and R2 and R3 are each H.
  • the present disclosure relates to a process for producing the compound described herein, the process comprising: reacting a compound represented by formula II: wherein Ar is a C10-C14 arylene group; with a compound represented by formula III:
  • HO-A2-R (IV), wherein A1 and A2 are each, independently, -(CH2)n-, wherein each occurrence of n is an integer from 1 to 12, and
  • R’ and R are each, independently, a moiety selected from the group consisting of acrylate, methacrylate, maleimide, acrylamide, and vinyl sulfone; with the proviso that when Ar is a biphenylene group and R’ and R” are each acrylate or methacrylate, n is an integer from 5 to 12.
  • the compound represented by formula II is an aromatic diacid in which Ar is a C10- C14 arylene group. Suitable C10-C14 arylene groups are those already described hereinabove. Such groups include, but are not limited to, those derived from benzene, biphenyl, naphthalene, anthracene, and phenanthrene.
  • the two bonds connecting the carbonyl carbons to Ar are not limited and may be on the same ring or on different rings.
  • Ar of the compound of formula II is selected from the group consisting of:
  • Ar of the compound of formula II is selected from the group consisting of:
  • HO-A2-R (IV).
  • Ai of the compound of formula III and A2 of the compound of formula IV provide alkylene functionalities that act as flexible spacers in the polymers produced from the compound made.
  • A1 and A2 are each, independently, -(CH2)n-, wherein each occurrence of n is an integer from 1 to 12.
  • A1 of the compound of formula III and A2 of the compound of formula IV are unsubstituted.
  • A1 of the compound of formula III and A2 of the compound of formula IV are identical and n is an integer from 2 to 4.
  • R’ of the compound of formula III and R” of the compound of formula IV provide the reactive functionality required for producing polymers from the compound made by this process.
  • Suitable reactive moieties are moieties already described hereinabove, i.e. , moieties comprising an alkene adjacent to a carbonyl or sulfone group.
  • R’ of the compound of formula III and R” of the compound of formula IV are each, independently, a moiety selected from the group consisting of acrylate, methacrylate, maleimide, acrylamide, and vinyl sulfone.
  • R’ of the compound of formula III and R” of the compound of formula IV are each, independently,
  • R1, R2, R3, R4, Rs, Re, R7, Rs, R9, R10, R11, and R12 are each, independently, H or CH3.
  • R’ of the compound of formula III and R” of the compound of formula IV are each
  • Ri is H or CH3, typically H, and R2 and R3 are each H.
  • A1 and A2 may be identical and R’ and R” may be identical.
  • the compound of formula III and the compound of formula IV are identical.
  • the compound of formula II is reacted with one reagent.
  • the compounds of formula II, III, and IV may be obtained from commercial sources or synthesized according to published methods.
  • the reaction between the compound of formula II with the compound of formula III and/or the compound of formula IV is an apparent transesterification reaction in which ester linkages are formed between the compound of formula II and the compound of formula III and/or the compound of formula IV.
  • Such reactions are known and may be conducted by to those of ordinary skill in the art according to known methods.
  • the carboxylic acid groups of the compound of formula III are first converted into acyl chloride groups, for example, using thionyl chloride.
  • the resulting compound is then reacted with the compound of formula III and/or the compound of formula IV.
  • the present disclosure relates to a polymer comprising a repeating unit derived from the compound described hereinabove or derived from the compound produced by the process described hereinabove.
  • the polymer comprises 1 to 100 %, typically 20 to 95 %, more typically 50 to 90 %, still more typically 65 to 80 %, by weight of the repeating unit derived from the compound described hereinabove or derived from the compound produced by the process described hereinabove.
  • the polymer may be a thermoplastic or thermoplastic-like linear or branched polymer. In some cases, the polymer may be a thermoset or thermoset-like polymer, typically with crosslinked structure. In an embodiment, the polymer is a liquid crystalline polymer. As used herein, a liquid crystalline polymer, or “LCP”, refers to a type of thermoplastic polymer that exhibits properties between highly ordered solid crystalline materials and amorphous disordered liquids over a well-defined temperature range.
  • the present disclosure relates to a process for producing a polymer described hereinabove, the process comprising reacting the compound described hereinabove or the compound produced by the process described hereinabove, typically a compound of formula I, with a compound comprising one or more, typically two or more, thiol or amine groups, with a compound comprising one or more acrylate or methacrylate groups, with a compound comprising one or more vinyl ether groups, or with a compound comprising one or more maleimide groups.
  • the compound described hereinabove or the compound produced by the process described hereinabove is reacted with a compound comprising one or more, typically two or more, thiol or amine groups, typically thiol groups, to produce the polymer.
  • the compound of formula I is reacted with a compound comprising two or more thiol groups to produce the polymer.
  • the polymerization reaction may be carried out according to methods known to those of ordinary skill in the art.
  • the present disclosure relates to an article comprising the polymer described hereinabove or polymer produced according to the process described hereinabove.
  • the article may be produced according to any method known to those of ordinary skill in the art, typically from the polymer or compositions comprising the polymer described herein.
  • Exemplary methods for manufacturing the article include, but are not limited, injection molding, extrusion, compression molding, thermoforming, such as sheet thermoforming, vacuum forming, pressure forming, trapped sheet forming, steam pressure forming; liquid resin casting, transfer molding, and additive manufacturing, such as 3D printing.
  • the polymer or compositions comprising the polymer used to produce the articles described herein may further comprise optional materials, such as fibers, fillers, colorants, additives, and the like, that impart beneficial properties to the final article.
  • Fibers may serve as reinforcing media and include, but are not limited to, carbon fiber, synthetic polymeric fibers, silicate fibers, such as aluminum silicate fibers, metal oxide fibers, such as alumina fibers, titania fibers, and magnesia fibers, wollastonite, rock wool fibers, silicon carbide fibers, etc.
  • Exemplary polymeric fibers include fibers formed from high temperature engineering polymers such as, for example, poly(benzothiazole), poly(benzimidazole), polyarylates, poly(benzoxazole), polyaryl ethers and the like, and may include mixtures comprising two or more such fibers.
  • Other optional materials include glass, calcium silicate, silica, clays, such as kaolin, talc, chalk, mica, potassium titanate, and other mineral fillers; colorants, including pigments such as carbon black, titanium dioxide, zinc oxide, iron oxide, cadmium red, iron blue; and other additives such as alumina trihydrate, sodium aluminum carbonate, barium ferrite, etc.
  • the polymer or compositions comprising the polymer may further include additional additives commonly employed by those of ordinary skill in the art, such as thermal stabilizers, ultraviolet light stabilizers, oxidative stabilizers, plasticizers, lubricants, and mold release agents, such as polytetrafluoroethylene (PTFE) powder, and the like.
  • additional additives commonly employed by those of ordinary skill in the art, such as thermal stabilizers, ultraviolet light stabilizers, oxidative stabilizers, plasticizers, lubricants, and mold release agents, such as polytetrafluoroethylene (PTFE) powder, and the like.
  • PTFE polytetrafluoroethylene
  • the article is:
  • an extruded article such as a film, fiber, sheet stock, rod stock, tubing or profile ;
  • valve component or a related part thereof such as a seal ring ;
  • an aerospace electrical or electronic connector component or housing ⁇ a friction and wear component such as a bushing, a bearing or a thrust washer,
  • a glide ring a tappet, a gear, an electronically driven pad, a control valve, a pump component, a bushing or a check ball of a brake system ;
  • a pump component a gear, or a sensor of an emission system ;
  • Example 1 Synthesis of a compound of formula I (NDA-HEA). 2,6-naphthalenedicarboxylic acid (NDA) (1 eq.) and thionyl chloride (10 eq.) were added to a oven dried 3-neck round-bottomed flask equipped with a gas adapter and condenser. The exit flow of the reaction setup was connected to an acid trap filled with a basic solution/base pellets. 5 drops of dimethylformamide (DMF) were added. The system was purged with N2 gas then refluxed for 5 h. The flask was then removed from heat and allowed to cool. The reaction flask was then equipped with a short-path distillation and the remaining thionyl chloride was distilled off.
  • NDA 2,6-naphthalenedicarboxylic acid
  • thionyl chloride 10 eq.
  • a solution of hydroxyethylacrylate (HEA) (2.1 eq.), triethylamine (TEA) (2.1 eq.) in 2-methyl-tetrahydrofuran (2-Me-THF) (20 wt %) was prepared in an addition funnel and chilled. After distillation was completed, the resulting product was dissolved in 2-Me-THF with a few drops of TEA. The system was then chilled down to 0 °C in an ice bath and purged again with N2 gas. The prepared solution of HEA and TEA in 2-Me-THF was then added drop-wise, ensuring the temperature did not exceed 4 °C. When the addition finished, the reaction mixture was stirred at room temperature for 16 h.
  • HEA hydroxyethylacrylate
  • TEA triethylamine
  • NDA-HBA was made according to the procedure of Example 1 , except that 4- hydroxybutyl acrylate (HBA) was used instead of HEA.
  • BB-HEA was made according to the procedure of Example 1 , except that 4,4’biphenyldicarboxylic acid (4,4’BB) was used instead of NDA and dichloromethane (DCM) was used in place of 2-Me-THF.
  • 4,4’biphenyldicarboxylic acid (4,4’BB) was used instead of NDA and dichloromethane (DCM) was used in place of 2-Me-THF.
  • DCM dichloromethane
  • BB-HBA was made according to the procedure of Example 1 , except that 4,4’BB was used instead of NDA, HBA was used instead of HEA, and DCM was used in place of 2-Me-THF.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Indole Compounds (AREA)

Abstract

La présente invention concerne de nouveaux composés monomères aromatiques de formule (I), y compris l'utilisation de tels monomères dans la production de polymères utiles. De tels composés monomères contiennent un noyau aromatique, un espaceur souple et une fonctionnalité réactive. Les nouveaux composés monomères de l'invention permettent la synthèse de polymères utiles sous diverses formes et selon de multiples techniques de traitement.
PCT/EP2022/069887 2022-07-15 2022-07-15 Composés aromatiques et polymères fabriqués à partir de ceux-ci WO2024012694A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140375943A1 (en) * 2013-06-25 2014-12-25 Merck Patent Gmbh Polymerizable compounds and the use thereof in liquid-crystal displays
US20150275026A1 (en) * 2012-10-29 2015-10-01 Ariste Medical, Inc. Polymer coating compositions and coated products
CN105542795A (zh) * 2016-02-25 2016-05-04 江苏和成新材料有限公司 手性可聚合液晶组合物及其应用
JP2017145220A (ja) * 2016-02-18 2017-08-24 株式会社トクヤマデンタル 重合性単量体の製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150275026A1 (en) * 2012-10-29 2015-10-01 Ariste Medical, Inc. Polymer coating compositions and coated products
US20140375943A1 (en) * 2013-06-25 2014-12-25 Merck Patent Gmbh Polymerizable compounds and the use thereof in liquid-crystal displays
JP2017145220A (ja) * 2016-02-18 2017-08-24 株式会社トクヤマデンタル 重合性単量体の製造方法
CN105542795A (zh) * 2016-02-25 2016-05-04 江苏和成新材料有限公司 手性可聚合液晶组合物及其应用

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