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WO2010011924A2 - Monomères dérivés de l’alpha- ou du bêta-amino-e-caprolactame et polymères fabriqués avec ces monomères - Google Patents

Monomères dérivés de l’alpha- ou du bêta-amino-e-caprolactame et polymères fabriqués avec ces monomères Download PDF

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Publication number
WO2010011924A2
WO2010011924A2 PCT/US2009/051689 US2009051689W WO2010011924A2 WO 2010011924 A2 WO2010011924 A2 WO 2010011924A2 US 2009051689 W US2009051689 W US 2009051689W WO 2010011924 A2 WO2010011924 A2 WO 2010011924A2
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WIPO (PCT)
Prior art keywords
caprolactam
polymer
monomer
amino
amido
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Ceased
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PCT/US2009/051689
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English (en)
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WO2010011924A3 (fr
Inventor
Douglas A. Wicks
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Draths Corp
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Draths Corp
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Publication of WO2010011924A3 publication Critical patent/WO2010011924A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
    • C08G69/14—Lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D223/12—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
    • C08G69/14—Lactams
    • C08G69/16—Preparatory processes
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
    • C08G69/14—Lactams
    • C08G69/22—Beta-lactams
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides

Definitions

  • Polyamides form a class of polymers which have been used for many years for numerous applications. Polyamides may be used alone or in combination with processing auxiliaries, polymeric alloying components, or mineral reinforcing materials (e.g. fillers or glass fibers) to produce materials with desirable properties. Polyamides are used in large quantities for the manufacture of fibers, plastics molded parts, films, and in technical applications such as hot- melt adhesives and auxiliary agents, (see, Vieweg, Muller; Kunststoff-Handbuch, Vol. Vl, pages 11 et seq. Carl-Hanser Verlag, Kunststoff, 1966).
  • polyamides have been produced from chemical feedstocks that are derived from oil.
  • industrially useful chemicals such as polyamides
  • renewable resources One such renewable starting material is biomass. It has been reported by Frost that biomass can be converted to ⁇ -amino- ⁇ -caprolactam by a combination of fermentation and chemical processes (see, U.S. Patent Publication No. 2007/149777). The resulting ⁇ -amino- ⁇ -caprolactam can serve as the basis for synthesizing industrially useful chemicals through appropriate chemical reaction and/or modification.
  • the invention relates to monomers that are derived from ⁇ - and ⁇ -amino- ⁇ -caprolactam and to polymers (homopolymers and copolymers) prepared from these monomers.
  • the ⁇ -amino- ⁇ -caprolactam or ⁇ -amino- ⁇ -caprolactam is manufactured from a renewable starting material, for example, biomass (see, U.S. Patent Publication No. 2007/149777 (Frost)).
  • the invention relates to polyamide polymers that are prepared by the polymerization of ⁇ -amido- ⁇ -caprolactam monomer, ⁇ -amido- ⁇ -caprolactam monomer, or a mixture thereof.
  • the monomers have the structures shown in Structure I and the polyamide polymers of the invention have the structure as shown in Structure II.
  • R 3 is — H or -NH R 1 ; w ith the proviso that, on adjacent carbon
  • R 3 is — H and one R 3 is -NH Ri ; and where R 1 is an alkyl group, an aryl group, or an aralkyl group.
  • R 1 is an alkyl group, an aryl group, or an aralkyl group.
  • the alkyl group, aryl group, or aralkyl group contain about 1 to about 21 carbon atoms.
  • the polyamide is a poly( ⁇ -amido- ⁇ -caprolactam) polymer having the structure
  • the polyamide is a poly( ⁇ -amido- ⁇ -caprolactam) polymers having the structure
  • the polyamide polymers of the invention expand the physical property space of known polyamides.
  • the R 1 group may be varied in order to affect the glass transition temperature (Tg), crystallinity, modulus, and hydrophobicity of the polyamide polymer, for example, as compared to Nylon 6 which is prepared from the polymerization of ⁇ -caprolactam.
  • the ⁇ -amido- ⁇ -caprolactam monomers of the invention are prepared by first preparing ⁇ -amino- ⁇ -caprolactam as shown in reaction scheme 1 , followed by conversion of ⁇ -amino- ⁇ -caprolactam to ⁇ -amido- ⁇ -caprolactam as shown in reaction scheme 2.
  • ⁇ -amido- ⁇ -caprolactam monomers of the invention are prepared by first preparing ⁇ -amino- ⁇ -caprolactam as shown in Reaction V, followed by conversion of ⁇ -amino- ⁇ -caprolactam to ⁇ -amido- ⁇ -caprolactam as shown in Reaction 2'.
  • biomass can be used as the starting material.
  • Step 1 the biomass is first converted into lysine or ⁇ -lysine by a fermentation process. This is followed by the conversion of lysine or ⁇ -lysine into ⁇ -amino- ⁇ -caprolactam or ⁇ -amino- ⁇ - caprolactam, respectively (Reaction 1 ).
  • the conversion of biomass to ⁇ -amido- ⁇ - caprolactam is described, for example, in U.S. Patent Publication No. 2007/149777 (Frost).
  • the conversion of biomass to ⁇ -lysine is described, for example, in WO 07/101867 (Zelder et al.).
  • reaction 2 the conversion of ⁇ -amino- ⁇ -caprolactam into ⁇ -amido- ⁇ -caprolactam is accomplished by reacting one equivalent of ⁇ -amino- ⁇ -caprolactam with one equivalent of carboxylic acid, with the concurrent loss of water. This reaction may be performed with an excess of the acid component followed by removal of any unreacted starting material. An example of this reaction is shown in reaction scheme Ill- ⁇ .
  • R 1 is as described hereinabove.
  • the ⁇ -amino- ⁇ -caprolactam can then be converted into ⁇ -amido- ⁇ -caprolactam
  • reaction 2 the conversion of ⁇ -amino- ⁇ -caprolactam into ⁇ - amido- ⁇ -caprolactam is accomplished by reacting one equivalent of ⁇ -amino- ⁇ -caprolactam with one equivalent of carboxylic acid, with the concurrent loss of water. This reaction may be performed with an excess of the acid component followed by removal of any unreacted starting material. An example of this reaction is shown in reaction scheme Ill- ⁇ . where Ri is as described hereinabove.
  • the ⁇ - or ⁇ -amido- ⁇ - caprolactam monomer is prepared by reacting an acid chloride or an acid anhydride in the presence of a mild base to scavenge the evolved acid.
  • Examples of useful carboxylic acids for preparing the ⁇ - or ⁇ -amido- ⁇ -caprolactam monomer are those containing about 2 to about 22 carbon atoms.
  • Representative examples include acetic acid, propionic acid, butyric acid, isobutyric, octanoic acid and its isomers, decanoic acid, dodecanoic acid, stearic acid, oleic acid, palmitic acid, myristic acid, arachidic acid, behenic acid, lignoceric acid, benzoic acid, napthoic acid, and mixtures thereof.
  • Preferred examples include acetic acid and C 16 to C 22 fatty acids.
  • the poly( ⁇ -amido- ⁇ -caprolactam) polymers of the invention are prepared by a ring opening polymerization of an ⁇ -amido- ⁇ -caprolactam monomer.
  • ring opening polymerization techniques include hydrolytic polymerization (i.e., hydrolytic polycondensation polymerization) and anionic ring-opening polymerization.
  • Hydrolytic polymerization is most commonly used for the preparation of polyamides from lactams (e.g., polyamide 6 from ⁇ -caprolactam).
  • Anionic ring opening polymerization of a lactam to form a polyamide is particularly useful in the preparation of reaction injection molding (i.e., RIM) polyamides due to the short time required for the reaction, which makes it possible for the lactam to be polymerized in the mold.
  • Examples of useful polymerization techniques include those reported in U.S. Patent No. 3,018,273 (describes a process for the anionic polymerization of caprolactam using an organomagnesium compound as the catalyst and an N-N diacyl compound as activator.); British Patent No. 1 ,067,153 (describes a process for preparing nylon block copolymers by polymerizing caprolactam in the presence of various kinds of activators. In the example, the use of an isocyanate-terminated polypropylene glycol as activator and of a potassium compound as catalyst is described).
  • the ⁇ -amido- ⁇ -caprolactam monomers are copolymerized with one or more lactam monomers to produce a copolymer.
  • the copolymer may be a random or block copolymer.
  • Suitable lactams for use in the polymerization include those containing about 5 to about 13 ring members, for example, pyrrolidone, ⁇ -caprolactam, oenantholactam, caprylic lactam or lauric lactam, used either separately or as mixtures, ⁇ - caprolactam and lauric lactam being preferred, ⁇ -caprolactam is particularly preferred.
  • the starting monomer composition may be varied along with the chain terminating agent type and composition in order to provide a polymer having the desired properties and molecular weight.
  • chain terminating agents such as monofunctional carboxylic acids or amines (e.g., acetic acid, hexanoic acid, benzoic acid, stearic acid, hexylamine or cyclohexylamine) may be used in typical quantities during the hydrolytic polycondensation.
  • monomers containing reactive groups may be included for various after-treatments (e.g. amino groups or sulphonate groups for improving the dye absorption of fibers with acid or basic dyes) that may be desired.
  • the ⁇ -amido- ⁇ -caprolactam monomers may be used as a low level (e.g., about 0.1 to 2.0 %wt.) additive to existing caprolactam hydrolytic polymerization processes.
  • the invention relates to ⁇ - and ⁇ -phthalimido- ⁇ -caprolactam monomers and to homopolymers and copolymers made therefrom.
  • the ⁇ -phthalimido- ⁇ -caprolactam monomers are prepared by the reaction of ⁇ -amino- ⁇ -caprolactam with phthalic anhydride according to reaction scheme IV- ⁇ .
  • the invention relates to ⁇ -phthalimido- ⁇ -caprolactam monomers and to homopolymers and copolymers made therefrom.
  • the ⁇ -phthalimido- ⁇ -caprolactam monomers are prepared by the reaction of ⁇ -amino- ⁇ -caprolactam with phthalic anhydride according to reaction scheme IV- ⁇ .
  • Mixtures of the ⁇ - and ⁇ -phthalimido- ⁇ -caprolactam monomers may also be used to prepare copolymers.
  • the ⁇ - and ⁇ -phthalimido- ⁇ -caprolactam monomers are useful in the preparation of polyamide polymers and copolymers via melt polymerization, hydrolytic melt polymerization, and anionic ring opening polymerization. These techniques may also be used to form copolymers using the ⁇ - and ⁇ -phthalimido- ⁇ -caprolactam monomers of the invention along with other lactam monomers. Copolymers may also be prepared by copolymerization of the ⁇ -and ⁇ -phthalimido- ⁇ -caprolactam monomers of the invention with diamines and dicarboxylic acids. Polyamide polymers prepared using the ⁇ - and ⁇ -phthalimido- ⁇ -caprolactam monomers of the invention are useful in the manufacture of fibers and in engineering thermoplastic resins.
  • the invention relates to ⁇ - and ⁇ -succinimido- ⁇ -caprolactam monomers and to homopolymers and copolymers made from the monomers.
  • the ⁇ -succinimido- ⁇ -caprolactam monomers are prepared by the reaction of ⁇ -amino- ⁇ -caprolactam with succinic acid or succinic anhydride.
  • the reaction of ⁇ -amino- ⁇ -caprolactam with succinic anhydride is shown in reaction scheme V- ⁇ .
  • the ⁇ -succinimido- ⁇ -caprolactam monomers are prepared by the reaction of ⁇ -amino- ⁇ -caprolactam with succinic acid or succinic anhydride.
  • the reaction of ⁇ -amino- ⁇ -caprolactam with succinic anhydride is shown in reaction scheme V- ⁇ .
  • Polyamide polymers prepared using the ⁇ - and ⁇ -succinimido- ⁇ -caprolactam monomers of the invention are useful in the manufacture of fibers and in engineering thermoplastic resins.
  • the invention provides ⁇ - and ⁇ -(meth)acrylamido- ⁇ - caprolactam monomers and to homopolymers and copolymers that are prepared therefrom.
  • the ⁇ -(meth)acrylamido- ⁇ -caprolactam monomers may be represented by Structure Vl- ⁇ or Structure Vl- ⁇ .
  • R 2 is hydrogen or an alkyl group.
  • the ⁇ -(meth)acrylamido- ⁇ -caprolactam monomers of the invention are prepared by reacting ⁇ -amino- ⁇ -caprolactam with (meth)acrylic acid (e.g., acrylic acid, methacrylic acid, or a mixture thereof) under conditions that are typical for amidation reactions.
  • (meth)acrylic acid e.g., acrylic acid, methacrylic acid, or a mixture thereof
  • An example of this reaction is shown in Scheme Vll- ⁇ .
  • R 2 is hydrogen or an alkyl group (e.g., methyl, ethyl, propyl, and the like).
  • the ⁇ -(meth)acrylamido- ⁇ -caprolactam monomers of the invention are prepared by reacting ⁇ -amino- ⁇ -caprolactam with (meth)acrylic acid (e.g., acrylic acid, methacrylic acid, or a mixture thereof) under conditions that are typical for amidation reactions.
  • (meth)acrylic acid e.g., acrylic acid, methacrylic acid, or a mixture thereof
  • An example of this reaction is shown in Scheme Vll- ⁇ .
  • F ⁇ is hydrogen or an alkyl group (e.g., methyl, ethyl, propyl, and the like).
  • the ⁇ - and ⁇ -(meth)acrylamido- ⁇ -caprolactam of the invention may be used as monomers for the preparation of free radically curable polymers.
  • Representative examples include acrylic/vinyl polymers and homopolymers and copolymers containing one or more ⁇ - or ⁇ -(meth)acrylamido- ⁇ -caprolactam monomers of the invention.
  • (meth)acrylamido- ⁇ -caprolactam momomers of the invention include coatings, adhesives, and sealants (i.e., CAS applications).
  • the monomers of the invention may be used to modify the glass transition temperature (T 9 ) of free radically curable polymers.
  • the monomers of the invention may also be useful to improve adhesion to polar and/or metallic substrates through hydrogen bonding and ion complexation. It is also expected that the high H-bonding characteristics of the monomers may add H-bonding crosslinking sites to coatings formed using the monomers.
  • the reversible H-bonding crosslinks may impart desirable properties to the resulting polymer including, for example, excellent abrasion resistance. All publications and patents mentioned herein are hereby incorporated by reference.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Polyamides (AREA)

Abstract

L’invention concerne des monomères dérivés du α- et du β-amino-ε-caprolactame et des polymères (par exemple homopolymères et copolymères) préparés à partir de ces monomères. Dans plusieurs modes de réalisation, le α-amino-ε-caprolactame ou le β-amino-ε-caprolactame est fabriqué à partir d’une matière première renouvelable, par exemple la biomasse. Dans un aspect, l’invention concerne des polymères de polyamide préparés par polymérisation de le α-amido-ε-caprolactame, du β-amido-ε-caprolactame, ou d’un mélange des deux. Dans certains modes de réalisation, les monomères ont les structures présentées en structure I et les polymères de polyamide de l’invention ont la structure présentée en structure II.
PCT/US2009/051689 2008-07-24 2009-07-24 Monomères dérivés de l’alpha- ou du bêta-amino-e-caprolactame et polymères fabriqués avec ces monomères Ceased WO2010011924A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13583008P 2008-07-24 2008-07-24
US61/135,830 2008-07-24

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WO2010011924A2 true WO2010011924A2 (fr) 2010-01-28
WO2010011924A3 WO2010011924A3 (fr) 2010-07-01

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120142887A1 (en) * 2010-12-03 2012-06-07 Basf Se Crosslinked polyamides
WO2012072548A3 (fr) * 2010-12-03 2012-08-30 Basf Se Polyamides à réticulation transversale
CN104558588A (zh) * 2013-10-22 2015-04-29 中国石油化工股份有限公司 一种尼龙聚合物及其制备方法
CN107973878A (zh) * 2016-10-25 2018-05-01 中国石油化工股份有限公司 一种共聚物及其制备方法和应用以及共混材料
CN109721695A (zh) * 2017-10-27 2019-05-07 中国石油化工股份有限公司 嵌段共聚物及其制备方法和应用以及尼龙/pps共混材料
US10513515B2 (en) 2017-08-25 2019-12-24 Biotheryx, Inc. Ether compounds and uses thereof
US11236103B2 (en) 2018-07-27 2022-02-01 Biotheryx, Inc. Bifunctional compounds
US11897930B2 (en) 2020-04-28 2024-02-13 Anwita Biosciences, Inc. Interleukin-2 polypeptides and fusion proteins thereof, and their pharmaceutical compositions and therapeutic applications

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3651023A (en) * 1968-07-02 1972-03-21 Stamicarbon Preparation of polyamides with special properties
US4297477A (en) * 1979-01-05 1981-10-27 Toray Industries, Incorporated Polyamide having --NH--(CH2)4 --CH(NRR')--CO--units
CN101006051B (zh) * 2004-06-10 2014-09-10 密歇根州州立大学托管理事会 由赖氨酸合成己内酰胺

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120142887A1 (en) * 2010-12-03 2012-06-07 Basf Se Crosslinked polyamides
WO2012072548A3 (fr) * 2010-12-03 2012-08-30 Basf Se Polyamides à réticulation transversale
CN103249761A (zh) * 2010-12-03 2013-08-14 巴斯夫欧洲公司 交联聚酰胺的方法
JP2013544314A (ja) * 2010-12-03 2013-12-12 ビーエーエスエフ ソシエタス・ヨーロピア 架橋ポリアミド
CN103249761B (zh) * 2010-12-03 2016-08-10 巴斯夫欧洲公司 交联聚酰胺的方法
CN104558588A (zh) * 2013-10-22 2015-04-29 中国石油化工股份有限公司 一种尼龙聚合物及其制备方法
CN107973878A (zh) * 2016-10-25 2018-05-01 中国石油化工股份有限公司 一种共聚物及其制备方法和应用以及共混材料
US10513515B2 (en) 2017-08-25 2019-12-24 Biotheryx, Inc. Ether compounds and uses thereof
US10927104B2 (en) 2017-08-25 2021-02-23 Biotheryx, Inc. Ether compounds and uses thereof
CN109721695A (zh) * 2017-10-27 2019-05-07 中国石油化工股份有限公司 嵌段共聚物及其制备方法和应用以及尼龙/pps共混材料
CN109721695B (zh) * 2017-10-27 2021-03-16 中国石油化工股份有限公司 嵌段共聚物及其制备方法和应用以及尼龙/pps共混材料
US11236103B2 (en) 2018-07-27 2022-02-01 Biotheryx, Inc. Bifunctional compounds
US11897930B2 (en) 2020-04-28 2024-02-13 Anwita Biosciences, Inc. Interleukin-2 polypeptides and fusion proteins thereof, and their pharmaceutical compositions and therapeutic applications

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