WO2019049862A1 - Dérivé de polylysine - Google Patents

Dérivé de polylysine Download PDF

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Publication number
WO2019049862A1
WO2019049862A1 PCT/JP2018/032749 JP2018032749W WO2019049862A1 WO 2019049862 A1 WO2019049862 A1 WO 2019049862A1 JP 2018032749 W JP2018032749 W JP 2018032749W WO 2019049862 A1 WO2019049862 A1 WO 2019049862A1
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Prior art keywords
group
substituent
ether bond
general formula
polylysine
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PCT/JP2018/032749
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English (en)
Japanese (ja)
Inventor
直哉 佐藤
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味の素株式会社
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Priority to JP2019540967A priority Critical patent/JP7196850B2/ja
Publication of WO2019049862A1 publication Critical patent/WO2019049862A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • 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
    • 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
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers

Definitions

  • the present invention relates to polylysine derivatives. Furthermore, the present invention relates to a dispersant, treated particles, a particle-containing composition, and a cosmetic comprising the polylysine derivative.
  • Color filters used to manufacture liquid crystal color displays, imaging devices and the like are manufactured using dispersion pigments.
  • a dispersed pigment is prepared, for example, using a pigment dispersant described in Patent Document 1.
  • the pigment dispersant described in Patent Document 1 is limited in its composition to cosmetics in consideration of the influence of the skin and the like. Therefore, development of new dispersants is required from the viewpoint of enabling application to a wide range of applications.
  • An object of the present invention is to provide a novel polylysine derivative.
  • the present invention includes the following contents.
  • a polylysine derivative having a polyester in a side chain [2] The polylysine derivative according to [1], which has a weight average molecular weight of 5,000 to 1,000,000.
  • a 1 represents a group represented by the following General Formula (2), General Formula (3), General Formula (4), or General Formula (5).
  • each of the a 1 R 1 s independently represents an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or a substituent R 2 represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or a substituent.
  • R ′ is an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, it may have a substituent Even if it has an alkyl group having an ether bond or a substituent Represents an alkenyl group having a good ether bond, and a represents an integer of 2 to 100.
  • a R 1 s may be the same as or different from each other.
  • R 1 s each independently have an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or a substituent.
  • R 2 represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, and a substituent A substituted or unsubstituted aryl group, an alkyl group having an ether bond which may have a substituent, an alkenyl group having an ether bond which may have a substituent, or -CO-R ' Group
  • R ′ is an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, it may have a substituent Alkyl group having an ether bond, or having a substituent
  • R 3 represents an alkenyl group having an optional ether bond
  • b R 3 s independently represent an alkylene group which may have a substituent, an
  • the b R 1 s and R 3 s may be the same or different.
  • [6] The polylysine derivative according to any one of [1] to [5], which has an amine value of 0 mg KOH / g to 220 mg KOH / g.
  • a dispersant comprising the polylysine derivative according to any one of [1] to [9].
  • a treated particle obtained by treating the particle with the dispersant described in [10].
  • a particle-containing composition comprising the polylysine derivative according to any one of [1] to [9], and a particle.
  • a cosmetic comprising the particle-containing composition according to [12].
  • a novel polylysine derivative that can be used as a dispersant; a dispersant, treated particles, a particle-containing composition, and a cosmetic comprising the polylysine derivative.
  • the polylysine derivative of the present invention the dispersant containing the polylysine derivative, the treated particles, the particle-containing composition, and the cosmetic will be described in detail.
  • the term “optionally having a substituent” attached immediately before a compound or group means that a hydrogen atom of the compound or group is substituted with a substituent, unless otherwise specified. It means both when there is nothing and when some or all of the hydrogen atoms of the compound or group are substituted with a substituent.
  • C r to C s (where r and s are positive integers and r ⁇ s) is an organic group described immediately after this term unless otherwise noted. Represents that the number of carbon atoms of r is s.
  • C 1 to C 10 alkyl group indicates an alkyl group having 1 to 10 carbon atoms
  • C 1 to C 10 alkyl ester indicates an ester with an alkyl group having 1 to 10 carbon atoms. .
  • an alkylene group is a generic term for linear, branched or cyclic alkylene groups unless otherwise specified.
  • the cyclic alkylene group may be either monocyclic or polycyclic. The same applies to other functional groups.
  • the polylysine derivative has a polyester (polyester moiety) in the side chain.
  • the polylysine site which is the main chain of the polylysine derivative may be either ⁇ -lysine-derived or ⁇ -lysine-derived, or may be a mixture.
  • the constituent unit of the polylysine site may be either L-form or D-form, and may be a racemate.
  • the polyester moiety possessed in the side chain of the polylysine derivative is not particularly limited as long as it is a polyester chain, for example, a polyester chain derived from 12-hydroxystearic acid, a polyester chain derived from ⁇ -caprolactone chain, and a polyester chain combining these Can be mentioned.
  • the polylysine derivative may be, for example, a copolymer of a structural unit of polyester in side chain and a structural unit of amino group in side chain.
  • the polylysine derivative preferably has a structural unit represented by the following general formula (1).
  • a 1 represents a group represented by the following General Formula (2), General Formula (3), General Formula (4), or General Formula (5).
  • I is 0 or 4 J represents 4 when i represents 0 and 0 when i represents 4)
  • each of the a 1 R 1 s independently represents an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or a substituent R 2 represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or a substituent.
  • R ′ is an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, it may have a substituent Even if it has an alkyl group having an ether bond or a substituent Represents an alkenyl group having a good ether bond, and a represents an integer of 2 to 100.
  • a R 1 s may be the same as or different from each other.
  • R 1 s each independently have an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or a substituent.
  • R 2 represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, and a substituent A substituted or unsubstituted aryl group, an alkyl group having an ether bond which may have a substituent, an alkenyl group having an ether bond which may have a substituent, or -CO-R ' Group
  • R ′ is an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, it may have a substituent Alkyl group having an ether bond, or having a substituent
  • R 3 represents an alkenyl group having an optional ether bond
  • b R 3 s independently represent an alkylene group which may have a substituent, an
  • a 1 represents a group represented by General Formula (2), General Formula (3), General Formula (4), or General Formula (5).
  • the plurality of A 1 is preferably a combination of the general formula (2) and the general formula (3), or a combination of the general formula (3) and the general formula (4).
  • i 0 or 4
  • j 4 when i represents 0, and 0 when i represents 4.
  • i 4
  • j 0.
  • the polylysine derivative preferably has at least two structural units represented by the general formula (1) in one molecule.
  • the constituent units may be the same constituent unit or may be different constituent units.
  • the same structural unit is a structural unit in which all groups represented by each A 1 in structural units represented by two or more general formulas (1) are the same, and different structural units are each represented by each A 1 Groups are different structural units.
  • R 1 independently has an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or a substituent And an alkylene group having an ether bond.
  • the alkylene group which may have a substituent is preferably an alkylene group having 10 or more carbon atoms, more preferably an alkylene group having 13 or more carbon atoms, and further preferably an alkylene group having 15 or more carbon atoms. preferable. Further, an alkylene group having 30 or less carbon atoms is preferable, an alkylene group having 28 or less carbon atoms is more preferable, and an alkylene group having 25 or less carbon atoms is further preferable.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • the alkylene group may be linear, branched or cyclic, but a linear or branched alkylene group is preferable, and a branched alkylene group is more preferable.
  • alkylene group examples include decylene group, undecylene group, dodecylene group, tridecylene group, tetradecylene group, pentadecylene group, decahydronaphthalylene group, 1-hexyl undecylene group and the like, and undecylene group, 1-hexyl Undecylene is preferred.
  • the alkenylene group which may have a substituent is preferably an alkenylene group having 10 or more carbon atoms, more preferably an alkenylene group having 13 or more carbon atoms, and further preferably an alkenylene group having 15 or more carbon atoms. preferable. Further, an alkenylene group having 30 or less carbon atoms is preferable, an alkenylene group having 28 or less carbon atoms is more preferable, and an alkenylene group having 25 or less carbon atoms is further preferable.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • the alkenylene group may be linear, branched or cyclic, but a linear or branched alkenylene group is preferred. Examples of such an alkenylene group include decenylene group, undecenylene group, dodecenylene group, tridecenylene group, tetradecenylene group, pentadecenylene group and the like.
  • Examples of the alkylene group having an ether bond which may have a substituent include an oxyalkylene group, an alkyleneoxy group, an oxyalkyleneoxy group, an alkyleneoxyalkylene group, and an alkyleneoxyalkylene oxyalkylene group.
  • an alkylene group having an ether bond which may have a substituent an alkylene group having an ether bond having 10 or more carbon atoms is preferable, and an alkylene group having an ether bond having 13 or more carbon atoms is more preferable.
  • an alkylene group having an ether bond of 15 or more carbon atoms is more preferable.
  • the alkylene group which has a C30 or less ether bond is preferable, The alkylene group which has a C28 or less ether bond is more preferable, The alkylene group which has a C25 or less ether bond is further more preferable preferable.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • the alkylene group having an ether bond may be linear, branched or cyclic, but is preferably linear or branched.
  • alkylene group having such an ether bond for example, oxydecylene group, oxyundecylene group, oxidodecylene group, oxytridecylene group, oxytetradecylene group, oxypentadecylene group, oxycyclopropylene group, oxycycloene group
  • alkylene group having such an ether bond for example, oxydecylene group, oxyundecylene group, oxidodecylene group, oxytridecylene group, oxytetradecylene group, oxypentadecylene group, oxycyclopropylene group, oxycycloene group
  • alkylene group having such an ether bond for example, oxydecylene group, oxyundecylene group, oxidodecylene group, oxytridecylene group, oxytetradecylene group, oxypentadecylene group, oxycyclopropylene group, oxy
  • At least one of R 1 has the number of carbon atoms which may have a substituent, from the viewpoint of the solubility in the lipophilic material used in cosmetics etc. and the improvement of the dispersant characteristics.
  • Alkylene having 10 to 30 alkylene group, alkenyl group having 10 to 30 carbon atoms which may have a substituent, or ether bond having 10 to 30 carbon atoms which may have a substituent Preferably represents a group, and represents an alkylene group having 10 to 30 carbon atoms which may have a substituent, or a branched alkylene group having 10 to 30 carbon atoms which may have a substituent. Is more preferred.
  • the alkylene group which R 1 represents, an alkenylene group, and the alkylene group which has an ether bond may have a substituent.
  • the substituent is not particularly limited, and examples thereof include a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group and a monovalent heterocyclic ring.
  • alkylidene groups amino groups, silyl groups, acyl groups, acyloxy groups, carboxy groups, sulfo groups, sulfo groups, cyano groups, nitro groups, hydroxy groups, mercapto groups, oxo groups and the like.
  • halogen atom used as a substituent, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned.
  • the alkyl group used as a substituent may be linear or branched.
  • the number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 14, further preferably 1 to 12, and still more preferably 1 to 6.
  • As the alkyl group for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group And decyl, with hexyl being preferred.
  • the alkyl group used as a substituent may further have a substituent ("secondary substituent").
  • alkyl group which has such a secondary substituent the alkyl group substituted by the halogen atom is mentioned, for example, Specifically, trifluoromethyl group, trichloromethyl group, tetrafluoroethyl group, tetrachloroethyl group etc. Can be mentioned.
  • the number of carbon atoms of the cycloalkyl group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and still more preferably 3 to 6.
  • Examples of the cycloalkyl group include cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group.
  • the alkoxy group used as a substituent may be linear or branched.
  • the number of carbon atoms of the alkoxy group is preferably 1 to 20, more preferably 1 to 12, and still more preferably 1 to 6.
  • the alkoxy group for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, The octyloxy group, the nonyloxy group, and the decyloxy group are mentioned.
  • the carbon atom number of the cycloalkyloxy group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and still more preferably 3 to 6.
  • Examples of the cycloalkyloxy group include cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group and cyclohexyloxy group.
  • the aryl group used as a substituent is a group obtained by removing one hydrogen atom on an aromatic ring from an aromatic hydrocarbon.
  • the number of carbon atoms of the aryl group used as a substituent is preferably 6 to 24, more preferably 6 to 18, still more preferably 6 to 14, and still more preferably 6 to 10.
  • Examples of the aryl group include phenyl group, naphthyl group and anthracenyl group.
  • the carbon atom number of the aryloxy group used as a substituent is preferably 6 to 24, more preferably 6 to 18, still more preferably 6 to 14, and still more preferably 6 to 10.
  • Examples of the aryloxy group used as a substituent include phenoxy group, 1-naphthyloxy group, and 2-naphthyloxy group.
  • the number of carbon atoms of the arylalkyl group used as a substituent is preferably 7 to 25, more preferably 7 to 19, still more preferably 7 to 15, and still more preferably 7 to 11.
  • Examples of the arylalkyl group include phenyl-C 1 -C 12 alkyl group, naphthyl-C 1 -C 12 alkyl group, and anthracenyl-C 1 -C 12 alkyl group.
  • the number of carbon atoms of the arylalkoxy group used as a substituent is preferably 7 to 25, more preferably 7 to 19, still more preferably 7 to 15, and still more preferably 7 to 11.
  • Examples of the arylalkoxy group include phenyl-C 1 -C 12 alkoxy group and naphthyl -C 1 -C 12 alkoxy group.
  • the monovalent heterocyclic group used as a substituent refers to a group in which one hydrogen atom has been removed from the heterocyclic ring of the heterocyclic compound.
  • the number of carbon atoms of the monovalent heterocyclic group is preferably 3 to 21, more preferably 3 to 15, and still more preferably 3 to 9.
  • the monovalent heterocyclic group also includes a monovalent aromatic heterocyclic group (heteroaryl group).
  • Examples of the monovalent heterocyclic ring include thienyl group, pyrrolyl group, furanyl group, furyl group, pyridyl group, pyridazinyl group, pyrimidyl group, pyrazinyl group, triazinyl group, pyrrolidinyl group, piperidyl group, quinolyl group, and isoquinolyl group. Can be mentioned.
  • the alkylidene group used as a substituent means the group which removed two hydrogen atoms from the same carbon atom of alkane.
  • the number of carbon atoms of the alkylidene group is preferably 1 to 20, more preferably 1 to 14, more preferably 1 to 12, still more preferably 1 to 6, and particularly preferably 1 to 3.
  • alkylidene group examples include methylidene group, ethylidene group, propylidene group, isopropylidene group, butylidene group, sec-butylidene group, isobutylidene group, tert-butylidene group, pentylidene group, hexylidene group, heptylidene group, octylidene group, nonylidene Groups, and decylidene groups.
  • the alkyl group represented by R may be linear or branched.
  • a phenyl group, a naphthyl group, and an anthracenyl group are mentioned, for example.
  • the number of carbon atoms of the acyl group is preferably 2 to 20, more preferably 2 to 13, and still more preferably 2 to 7.
  • Examples of the acyl group include acetyl group, propionyl group, butyryl group, isobutyryl group, pivaloyl group and benzoyl group.
  • the alkyl group represented by R may be linear or branched.
  • a phenyl group, a naphthyl group, and an anthracenyl group are mentioned, for example.
  • the carbon atom number of the acyloxy group is preferably 2 to 20, more preferably 2 to 13, and still more preferably 2 to 7.
  • Examples of the acyloxy group include acetoxy group, propionyloxy group, butyryloxy group, isobutyryloxy group, pivaloyloxy group, and benzoyloxy group.
  • the above-mentioned substituent may further have a substituent (hereinafter sometimes referred to as "secondary substituent").
  • secondary substituent the same as the above-mentioned substituent may be used unless otherwise specified.
  • R 2 has a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, and a substituent Group which may be substituted, an alkyl group having an ether bond which may have a substituent, an alkenyl group having an ether bond which may have a substituent, or a group represented by -CO-R ' R ′ is an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, an ether bond which may have a substituent Or an alkenyl group having an ether bond which may have a substituent.
  • an alkyl group having 1 to 30 carbon atoms is preferable, an alkyl group having 1 to 20 carbon atoms is more preferable, and an alkyl having 1 to 10 carbon atoms is preferable
  • the group is more preferably an alkyl group having 1 to 6 carbon atoms.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • the alkyl group may be linear, branched or cyclic, but a linear or branched alkyl group is preferred.
  • alkyl group for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, Nonyl group, decyl group and the like can be mentioned.
  • the alkenyl group which may have a substituent is preferably an alkenyl having 2 to 30 carbon atoms, more preferably an alkenyl group having 2 to 20 carbon atoms, and further preferably an alkenyl group having 2 to 10 carbon atoms. preferable.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • the alkenyl group may be linear, branched or cyclic, but a linear or branched alkenyl group is preferred.
  • alkenyl groups examples include ethenyl group, propenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group and the like.
  • the aryl group which may have a substituent is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and an aryl group having 6 to 10 carbon atoms Is more preferred.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • a phenyl group, a naphthyl group, an anthracenyl group etc. are mentioned, for example, A phenyl group is preferable.
  • Examples of the alkyl group having an ether bond which may have a substituent include an alkyleneoxyalkyl group and an alkyleneoxyalkyleneoxyalkyl group.
  • an alkyl group having an ether bond which may have a substituent an alkyl group having an ether bond having 2 to 30 carbon atoms is preferable, and an alkyl group having an ether bond having 2 to 20 carbon atoms is more preferable.
  • alkyl groups having an ether bond of 2 to 10 carbon atoms are more preferable.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • the alkyl group may be linear, branched or cyclic, but a linear or branched alkyl group is preferred.
  • alkylene group having such an ether bond a methyleneoxymethyl group, a methyleneoxyethyl group, a methyleneoxypropyl group, a methyleneoxybutyl group, a methyleneoxypentyl group, a methyleneoxyhexyl group, a methyleneoxyheptyl group, a methyleneoxy group Octyl group, methylene oxynonyl group, methylene oxydecyl group, methylene oxyundecyl group, methylene oxy dodecyl group, methylene oxy tridecyl group, methylene oxy tetradecyl group, methylene oxy pentadecyl group, methylene oxy cyclopropyl group, methylene oxy Cyclobutyl, methyleneoxycyclopentyl, methyleneoxycyclohexyl, methyleneoxydecahydronaphthalyl, methyleneoxynorborn
  • Examples of the alkenyl group having an ether bond which may have a substituent include an alkenylene oxyalkenyl group, an alkenylene oxyalkenylene alkenyl group and the like.
  • an alkenyl group having an ether bond which may have a substituent an alkenyl group having 3 to 30 carbon atoms is preferable, and an alkenyl group having an ether bond having 3 to 20 carbon atoms is more preferable.
  • An alkenyl group having an ether bond of 3 to 10 carbon atoms is more preferable.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • the alkenyl group may be linear, branched or cyclic, but a linear or branched alkenyl group is preferred.
  • alkenyl group having such an ether bond for example, ethenylene oxyethenyl group, ethenylene oxypropenyl group, ethenylene oxybutenyl group, ethenylene oxyhexenyl group, ethenylene oxyheptenyl group, ethenylene oxy Octenyl group, ethenylene oxydecenyl group etc. are mentioned.
  • R ′ in the group represented by —CO—R ′ is an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or an aryl which may have a substituent A group, an alkyl group having an ether bond which may have a substituent, or an alkenyl group having an ether bond which may have a substituent.
  • the group represented by -CO-R ' is preferably a carbonylalkyl group or a benzoyl group.
  • R 2 is a hydrogen atom or a carbon atom having 2 to 2 carbon atoms which may have a substituent, from the viewpoint of improving the solubility in a lipophilic material used in cosmetics and the like and the dispersant characteristics.
  • R 2 represents an alkyl group of 30 or an alkenyl group having 2 to 30 carbon atoms which may have a substituent, and more preferably a hydrogen atom.
  • A represents an integer of 2 to 100, preferably an integer of 3 to 50, more preferably an integer of 4 to 40, and still more preferably an integer of 5 to 30.
  • the alkyl group represented by R 2 may have a substituent.
  • the substituent is the same as the substituent which the alkylene group represented by R 1 may have.
  • the alkyl group, the alkenyl group, the aryl group, the alkyl group having an ether bond, and the alkenyl group having an ether bond represented by R ′ may have a substituent.
  • the substituent is the same as the substituent which the alkylene group represented by R 1 may have.
  • R 1 independently has an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or a substituent It also represents an alkylene group having a good ether linkage.
  • the alkylene group which may have a substituent, the alkenylene group which may have a substituent, and the alkylene group having an ether bond which may have a substituent, which R 1 represents, have a formula (2
  • R 2 is a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or a substituent
  • alkyl group which may have a substituent an alkenyl group which may have a substituent, an aryl group which may have a substituent, and a substituent which R 2 represents.
  • R 3 independently represents an alkylene group which may have a substituent or an alkylene group having an ether bond which may have a substituent.
  • the alkylene group which may have a substituent is preferably an alkylene group having 1 or more carbon atoms, more preferably an alkylene group having 2 or more carbon atoms, and further preferably an alkylene group having 3 or more carbon atoms.
  • an alkylene group having 4 or more carbon atoms is particularly preferable.
  • an alkylene group having 30 or less carbon atoms is preferable, an alkylene group having 20 or less carbon atoms is more preferable, an alkylene group having 15 or less carbon atoms is further preferable, and an alkylene group having 10 or less carbon atoms is Particularly preferred.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • the alkylene group may be linear, branched or cyclic, but a linear or branched alkylene group is preferable, and a linear alkylene group is more preferable.
  • an alkylene group for example, ethylene group, propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, undecylene group, undecylene group, dodecylene group, tridecylene group, tetradecylene group, pentadecylene Groups, decahydronaphthanylene group, 1-hexyl undecylene group, etc. are mentioned, and pentylene group, undecylene group, 1-hexyl undecylene group is preferable.
  • Examples of the alkylene group having an ether bond which may have a substituent include an oxyalkylene group, an alkyleneoxy group, an oxyalkyleneoxy group, an alkyleneoxyalkylene group, and an alkyleneoxyalkylene oxyalkylene group.
  • an alkylene group having an ether bond which may have a substituent an alkylene group having 2 or more carbon atoms is preferable, and an alkylene group having an ether bond having 3 or more carbon atoms is more preferable.
  • an alkylene group having 4 or more carbon atoms and having an ether bond is more preferable.
  • an alkylene group having an ether bond having 20 or less carbon atoms is preferable, an alkylene group having an ether bond having 15 or less carbon atoms is more preferable, and an alkylene group having an ether bond having 10 or less carbon atoms is further preferable.
  • the number of carbon atoms includes the number of carbon atoms of a substituent.
  • the alkylene group may be linear, branched or cyclic, but a linear or branched alkylene group is preferred.
  • alkylene group having such an ether bond for example, oxyethylene group, oxypropylene group, oxybutylene group, oxypentylene group, oxyhexylene group, oxyheptylene group, oxyoctylene group, oxynonylene group, oxydecylene group, Oxyundecylene group, Oxidodecylene group, Oxytridecylene group, Oxytetradecylene group, Oxypentadecylene group, Oxycyclopropylene group, Oxycyclobutylene group, Oxycyclopentylene group, Oxycyclohexylene group, Oxydecahydro group A naphthanylene group, an oxy norbornan ylene group, an oxy adamantanylene group etc. are mentioned.
  • R 3 at least one of C 2-30 carbon atoms which may have a substituent, from the viewpoint of improving the solubility in lipophilic materials used in cosmetics etc. and the dispersant properties It is preferable to represent an alkylene group, and more preferable to represent a linear alkylene group having 2 to 30 carbon atoms which may have a substituent.
  • B represents an integer of 1 to 100, preferably an integer of 1 to 50, more preferably an integer of 2 to 40, and still more preferably an integer of 3 to 30.
  • the structural unit represented by the general formula (1) is preferably a structural unit represented by the following general formula (1-1).
  • a 1 represents a group represented by General Formula (2), General Formula (3), General Formula (4), or General Formula (5).
  • a 1 in the general formula (1-1) is the same as A 1 in the general formula (1), and preferred ranges are also the same.
  • the polylysine derivative preferably has a structural unit represented by the following general formula (6).
  • the structural unit represented by the general formula (6) may correspond to, among the structural units contained in polylysine as a precursor of the polylysine derivative, those not bonded to the polyester chain. (In the general formula (6), m represents 0 or 4, n represents 4 when m represents 0, and 0 when m represents 4.)
  • m 0 or 4
  • n 4 when m represents 0, and 0 when m represents 4.
  • m preferably represents 4 and n preferably represents 0.
  • the polylysine derivative preferably has a structural unit represented by General Formula (6) together with the structural unit represented by General Formula (1).
  • the mass ratio of the structural unit represented by General Formula (1) to the structural unit represented by General Formula (6) As the mass of the structural unit represented by 1) / the mass of the structural unit represented by the general formula (6), it is said that the solubility in the lipophilic material used in cosmetics etc., and the improvement of the dispersant characteristics From the viewpoint, 1/19 or more is preferable, 1/9 or more is more preferable, and 1 ⁇ 4 or more is more preferable. By setting the mass ratio within such a range, the effects of excellent solubility and dispersibility are exhibited.
  • the side chain mass / main chain mass of the polylysine derivative is preferably 1 or more, more preferably 2 or more, and further preferably from the viewpoint of the solubility in a lipophilic material used in cosmetics etc. and the improvement of dispersant characteristics. Is 3 or more.
  • the upper limit is preferably 100 or less, more preferably 70 or less, and still more preferably 40 or less.
  • the side chain mass / main chain mass of the polylysine derivative can be measured according to the description of ⁇ side chain mass / main chain mass of polylysine derivative> described later.
  • the amine value of the polylysine derivative is preferably 0 mg KOH / g or more, more preferably 3 mg KOH / g or more, still more preferably from the viewpoint of the solubility in lipophilic materials used in cosmetics etc. and the improvement of dispersant characteristics. It is 5 mg KOH / g or more.
  • the upper limit is preferably 220 mg KOH / g or less, more preferably 160 mg KOH / g or less, and still more preferably 100 mg KOH / g or less.
  • the amine value of the polylysine derivative can be measured according to the description of ⁇ Measurement of amine value of polylysine derivative> described later.
  • the acid value of the polylysine derivative is preferably 0 mg KOH / g or more, more preferably 2 mg KOH / g or more, still more preferably from the viewpoint of the solubility in a lipophilic material used in cosmetics etc. and the improvement of dispersant characteristics. It is 4 mg KOH / g or more.
  • the upper limit is preferably 100 mg KOH / g or less, more preferably 70 mg KOH / g or less, and still more preferably 40 mg KOH / g or less.
  • the acid value of the polylysine derivative can be measured according to the description of ⁇ Measurement of acid value of polylysine derivative> described later.
  • the weight average molecular weight of the polylysine derivative is preferably 5000 or more, more preferably 10000 or more, and still more preferably 20000 or more, from the viewpoint of the solubility in a lipophilic material used in cosmetics etc. and the improvement of dispersant characteristics. is there.
  • the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less, and further preferably 100,000 or less.
  • the weight average molecular weight can be measured by gel permeation chromatography (GPC).
  • the method for producing the polylysine derivative is not particularly limited, and can be produced according to various methods. As a preferred embodiment, it can be produced by reacting polylysine with a polyester.
  • Lysine constituting polylysine may be L-form or D-form, and polylysine includes poly-L-lysine linked to L-lysine and poly-D-lysine linked to D-lysine .
  • polylysine includes ⁇ -polylysine in which a carboxyl group is peptide-bonded to an ⁇ -amino group of lysine, and ⁇ -polylysine in which an ⁇ -amino group of lysine and a carboxyl group are peptide-bonded.
  • polylysine can also be used.
  • polylysine can be obtained by appropriately using known methods such as (1) a method of chemically synthesizing or (2) a method of synthesizing by an enzymatic reaction.
  • polylysine can be synthesized or semi-synthesized using a peptide synthesizer.
  • polylysine is obtained by peptide solid phase synthesis.
  • the polylysine thus synthesized can be usually purified by, for example, ion exchange chromatography, reverse phase high performance liquid chromatography, affinity chromatography and the like.
  • Examples of the method of synthesis by an enzymatic reaction include the methods described in WO 2004/011653. That is, a lysine or dipeptide obtained by esterifying or amidifying the carboxyl terminus of one lysine or dipeptide, and a lysine in which the amino group is free (for example, a carboxyl-protected lysine) in the presence of a peptide-forming enzyme
  • the reaction is carried out in the following manner and the resulting polylysine is purified by purification.
  • a peptide-forming enzyme for example, a culture of a microorganism (for example, an actinomycete) having an ability to generate a peptide, a microbial cell separated from the culture, a treated product of the microbial cell, or a peptide derived from the microorganism An enzyme is mentioned.
  • a microorganism for example, an actinomycete
  • the weight-average molecular weight of polylysine varies depending on the number of linked lysines, but is preferably 650 to 300,000 and more preferably 1,000 to 70000.
  • the number average molecular weight of polylysine is preferably 150 to 100,000, and more preferably 600 to 20,000.
  • the adsorptive power to the pigment is improved to improve the pigment dispersibility, and when the number average molecular weight is 100,000 or less, aggregation of the pigments can be suppressed and the pigment dispersibility is improved.
  • polylysine can be used.
  • examples of commercially available products of polylysine include ⁇ -poly-lysine ( ⁇ -polylysine, weight average molecular weight 3600 to 4300) manufactured by Foodchem International Corporation.
  • Polylysine may be purified from polylysine hydrochloride.
  • hydrochloric acid may be removed by an ion exchange resin such as OH-type strongly basic anion exchange resin.
  • polymerized at random are mentioned.
  • R 1 is each independently an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or an ether which may have a substituent
  • R 2 represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, or an aryl group which may have a substituent.
  • an alkyl group having an ether bond which may have a substituent an alkenyl group having an ether bond which may have a substituent, or a group represented by —CO—R ′ (R ′ is a substituted group
  • R ′ is a substituted group
  • an a represents an integer of 2 to 100.
  • the plurality of R 1 s may be the same as or different from each other.
  • R 1 is each independently an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or an ether bond which may have a substituent
  • R 2 represents a hydrogen atom, an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, An alkyl group having an ether bond which may have a substituent, an alkenyl group having an ether bond which may have a substituent, or a group represented by —CO—R ′ (wherein R ′ represents a substituent An alkyl group which may have, an alkenyl group which may have a substituent, an aryl group which may have a substituent, an alkyl group having an ether bond which may have a substituent, or Ether bond optionally having a substituent
  • R 3 represents an alkylene group which may independently have a substituent or an alkylene group having an ether bond which
  • R 1, R 2 and a in the general formula (I), general formula (2) and the general formula (3) is the same as R 1 and a of, and preferred ranges are also the same.
  • R 1, R 2, R 3 and b in the general formula (II), formula (4) and general formula (5) is the same as R 1, R 3 and b, and preferred ranges are also the same .
  • the polyesters represented by the general formula (I) and the general formula (II) are represented by the hydroxy acids represented by the following general formula (III) and / or the general formula (IV), and / or the following general formula (V) Can be prepared from the lactones. Moreover, you may mix the compound represented by the following general formula (VI) to the reaction system for manufacturing polyester as needed.
  • R 1 has an alkylene group which may have a substituent, an alkenylene group which may have a substituent, or an ether bond which may have a substituent Represents an alkylene group.
  • R 3 represents an alkylene group which may have a substituent or an alkylene group having an ether bond which may have a substituent.
  • R 2 represents an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or a substituent An alkyl group having an ether bond which may have, an alkenyl group having an ether bond which may have a substituent, or a group represented by —CO—R ′ (R ′ has a substituent Alkyl group which may be substituted, alkenyl group which may have a substituent, aryl group which may have a substituent, alkyl group having an ether bond which may have a substituent, or a substituent Represents an alkenyl group having an ether bond which may be possessed). )
  • R 1 in the general formula (III) is the same as R 1 in ⁇ (II), and preferred ranges are also the same.
  • R 3 in the general formula (IV) and the general formula (V) is the same as R 3 in formula (II), and preferred ranges are also the same.
  • R 2 in the general formula (VI) is the same as R 2 in ⁇ (II), and preferred ranges are also the same.
  • the polyesters represented by the general formula (I) and the general formula (II) are represented by the hydroxy acids represented by the general formula (III) and / or the general formula (IV), and / or the general formula (V) It can be obtained by heating a mixture of lactones. Moreover, you may add and heat the compound, the polymerization catalyst, or the polymerization initiator represented by General formula (VI) to the reaction system for manufacturing polyester as needed.
  • the heating temperature and heating time can be appropriately adjusted depending on the type of hydroxy acid and the like, and can be, for example, 0.5 to 48 hours at 50 to 300 ° C.
  • hydroxy acids represented by the general formula (III) and the general formula (IV) include glycolic acid, ricinoleic acid, ricinolenic acid, a mixture of 9 and 10-hydroxystearic acid, 12-hydroxystearic acid, castor oil fatty acid And hydrogenated castor oil fatty acid, lactic acid and the like, with 12-hydroxystearic acid being preferred.
  • lactones represented by the general formula (V) include ⁇ -caprolactone, ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -methyl- ⁇ -valerolactone, 4-methylcaprolactone, Examples thereof include methyl caprolactone and the like, and ⁇ -caprolactone is preferable.
  • Examples of the compound represented by the general formula (VI) include water, methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, phenol and the like.
  • tetramethyl ammonium chloride for example, tetrabutyl ammonium chloride, tetramethyl ammonium bromide, tetrabutyl ammonium bromide tetramethyl ammonium iodo, tetrabutyl ammonium iodo, benzyl trimethyl ammonium chloride, benzyl trimethyl ammonium bromide, benzyl trimethyl ammonium iodo
  • Quaternary ammonium salts such as tetramethylphosphonium chloride, tetrabutylphosphonium chloride, tetramethylphosphonium bromide, tetrabutylphosphonium bromide, tetramethylphosphonium iodo, tetrabutyl phosphonium iodo, benzyltrimethylphosphonium chloride, benzyltrimethylphosphonium bromide, benzyltrimethylphosphonium bromide, benz
  • polymerization initiator examples include ketone peroxides such as methyl ethyl ketone, diacyl peroxides such as benzoyl peroxide; peroxy dicarbonates such as diisopropyl peroxy dicarbonate; 1, 1-bis (t-butylperoxyloxy) A) Peroxyketals such as cyclohexane; hydroperoxides such as t-butyl hydroperoxide; peroxy esters such as t-butyl peroxypivalate; acetic acid, propionic acid, caprylic acid, nonanoic acid, capric acid, Aliphatic monocarboxylic acids such as octylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isononanoic acid, arachic acid; aromatic monocarboxylic acids such as benzoic acid and p-butyl benzoic acid; Retril, hydrogen peroxide, ferrous salt etc It can gel. Furthermore, ket
  • the calculated molecular weight of the polyester used in the method for producing a polylysine derivative is preferably from 300 to 20,000, and more preferably from 1,000 to 10,000, from the viewpoint of pigment dispersion performance.
  • the molecular weight of the polyester can be calculated from the acid number of the polyester. In order to obtain a polyester of such molecular weight, it is necessary to set the molar ratio of the polymerization initiator, the hydroxy acid as the raw material, and the lactone, and observe the acid value of the reaction product on the way to find an appropriate reaction time. It is made possible.
  • the calculated molecular weight of the polyester can be measured according to the description of ⁇ Calculated molecular weight of polyester> described later.
  • the acid value of the polyester used in the method for producing a polylysine derivative is preferably 3 to 190 mg KOH / g, and more preferably 6 to 60 mg KOH, from the viewpoint of the solubility in lipophilic materials used in cosmetics and the like and the improvement of dispersant properties. / G is more preferable.
  • the acid value of the polyester can be measured according to the description of ⁇ Measurement of acid value of polyester> described later.
  • polyester is reacted with polylysine.
  • the reaction charge can be appropriately set so that the side chain mass / main chain mass of the polylysine and the polyester falls within the above-mentioned range.
  • the reaction temperature is preferably 50 ° C. or more, more preferably 70 ° C. or more, still more preferably 90 ° C. or more.
  • the upper limit is preferably 200 ° C. or less, more preferably 180 ° C. or less, and further preferably 160 ° C. or less.
  • the reaction time for reacting polyester with polylysine is preferably 1 hour or more, more preferably 2 hours or more, and still more preferably 3 hours or more.
  • the upper limit is preferably 48 hours or less, more preferably 24 hours or less, and further preferably 10 hours or less.
  • a solvent may be used from the viewpoint of gently advancing the reaction.
  • the solvent include toluene and the like.
  • a catalyst and / or a polymerization initiator may be added from the viewpoint of facilitating the reaction.
  • the catalyst include ferric chloride and the like.
  • a polymerization initiator the thing similar to the polymerization initiator used when obtaining polyester represented by General formula (I) can be used.
  • the dispersant contains a polylysine derivative.
  • Polylysine derivatives are useful as dispersants for pigments (pigment dispersants) because they have the property of dispersing pigments well in resins and organic solvents.
  • a polylysine derivative is also excellent in the dispersibility of carbon particles, so it can also be used as a sludge dispersant for lubricating oil.
  • Lubricating oils for internal combustion engines for example, gasoline engines, diesel engines, gas engines
  • drive system lubricating oils for example, gear oils for automobiles etc., hydraulic oils, automatic transmission oils, all-purpose transmission oils, power steering oils, etc.
  • various problems are caused to the internal combustion engine and the drive system site such as increase of dirt and wear of the lubrication site by generating sludge and increase of power loss.
  • the polylysine derivative as a sludge dispersant to the lubricating oil, it is possible to suppress the growth of sludge and maintain the performance as a lubricating oil for a long time.
  • the polylysine derivative can be used as a dispersant for pigments and the like contained in cosmetics such as cosmetics because it has less influence on human skin.
  • the treated particles are those obtained by treating the particles with the above-mentioned dispersant.
  • Examples of the treated particles include treated inorganic particles, treated organic particles, and the like.
  • the particles are not particularly limited as long as they are inorganic particles or organic particles.
  • the inorganic particles for example, titanium oxide, iron oxide, cadmium sulfide, calcium carbonate, barium carbonate, barium sulfate, clay, talc, yellow lead, carbon black, cadmium yellow, cadmium red, red iron oxide, iron black, zinc flower, Inorganic pigments such as bitumen and ultramarine are listed.
  • organic particles examples include pyrrole type such as diketopyrrolopyrrole, monoazo type, diazo type, azo lake type, condensed azo type, chelate azo type, chelate azo type, indigo type, thioindigo type, anthraquinone type, dianthlaquinonyl type and benzimidazo.
  • pyrrole type such as diketopyrrolopyrrole, monoazo type, diazo type, azo lake type, condensed azo type, chelate azo type, chelate azo type, indigo type, thioindigo type, anthraquinone type, dianthlaquinonyl type and benzimidazo.
  • Ron system pyranthrone system, phthalocyanine system, halogenated phthalocyanine system, flavanthrone system, quinacridone system, dioxazine system, indanthrone system, isoindolinone system, isoindoline system, quinophthalone system, perylene system, perinone system, acid dye system And organic pigments such as basic dyes, azines, daylight fluorescents, nitrosos and nitros.
  • the inorganic particles in addition to the above-mentioned pigments, for example, silica, alumina, barium titanate, calcium phosphate, calcium hydrogen phosphate, magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, dolomite, calcined dolomite, Fire extinguishing dolomite, hydrotalcite, silicon dioxide, glass particles, silicon nitride, aluminum nitride, boron nitride, iron nitride, ferrite, strontium ferrite, barium ferrite, carbon particles, carbon nanotubes, fullerene, graphene, magnetic substance (such as samarium cobalt, And neodymium iron boron, praseodymium cobalt, samarium iron nitrogen, etc.) and diamond particles.
  • organic particles in addition to the above-mentioned pigments, for example, poly (meth) acrylate, polyester, polystyrene, silicone, polyamide, polyvinyl chloride, ABS, polyphenylene sulfide, polyamide imide, polyether sulfone, epoxy resin Etc. may be mentioned.
  • the (meth) acrylic acid ester includes particles of acrylic acid ester and methacrylic acid ester.
  • the average particle diameter of the particles is preferably 10 nm or more, more preferably 30 nm or more, and still more preferably 50 nm or more.
  • the upper limit is preferably 1000 ⁇ m or less, more preferably 100 ⁇ m or less, and further preferably 10 ⁇ m or less.
  • the average particle size of the particles can be measured, for example, by a laser diffraction method or a dynamic light scattering method.
  • the method of processing and dispersing particles with a dispersing agent is, for example, a method of processing using a Henschel mixer, bead mill, ball mill, planetary mixer, paint shaker, atomizer colloid mill, banbury mixer, etc., dry method, wet method, integral blend Law etc. are mentioned.
  • the surface of the particles may be treated with a dispersing agent first, and then it may be blended with a solvent, resin, rubber or the like, and the dispersing agent may be added when the particles are blended with a solvent, resin or rubber, etc. Good.
  • the solvent may be removed to take out particles whose surface has been treated with a dispersant.
  • solvents capable of dissolving a dispersant can be used, and examples thereof include aromatics such as toluene and xylene, aliphatic hydrocarbons such as n-hexane, n-heptane and isoparaffin, MIBK Examples thereof include ketones such as (methyl isobutyl ketone) and MEK (methyl ethyl ketone), and esters such as ethyl acetate and butyl acetate.
  • dispersion may be performed while forming particles in a solution in which the dispersant is dissolved by a suspension method by high-speed stirring or the like, a suspension polymerization method, or the like.
  • the dispersant is preferably contained in an amount of 1 to 200% by mass (in terms of polylysine derivative) based on the particles.
  • the particle-containing composition comprises the polylysine derivative of the present invention, and particles.
  • the particle-containing composition include pigment dispersions, inorganic particle dispersions, organic particle dispersions, pigment-containing polymer compositions, inorganic particle-containing polymer compositions, organic particle-containing polymer compositions, and the like.
  • the polymer includes resin, rubber and the like.
  • the particle-containing composition may contain additives such as a resin, rubber, an organic solvent, a stabilizer, an antioxidant, a plasticizer, a UV absorber, and a dispersing aid to the extent that the effects of the present invention are not impaired.
  • the particles in the particle-containing composition may be particles treated with a dispersant or particles not treated with a dispersant. As the particles, those similar to the particles described in ⁇ treated particles> can be used.
  • the resin examples include alkyd resin, polyester resin, (meth) acrylic resin, epoxy resin, polyurethane resin, silicone resin, fluorine resin, melamine resin, benzoguanamine resin, urea resin, polyamide resin, phenol resin, vinyl chloride, polyethylene resin And styrene resins, acid group-containing resins, and copolymers thereof (eg, benzyl methacrylate / methacrylic acid copolymer, styrene / stearyl methacrylate / acrylic acid copolymer), etc., but not limited thereto. .
  • the (meth) acrylic resin includes acrylic resin and methacrylic resin.
  • the rubber for example, natural rubber, synthetic rubber, isoprene rubber, butadiene rubber, styrene butadiene rubber, chloroprene rubber, nitrile rubber, polyisobutylene, ethylene propylene rubber, chlorosulfonated polyethylene, acrylic rubber, fluororubber, epichlorohydrin
  • rubber urethane rubber, silicone rubber etc. are mentioned, it is not limited to these.
  • organic solvent examples include hydrocarbon solvents such as toluene, xylene, high-boiling petroleum hydrocarbon, n-hexane, cyclohexane, n-heptane, etc .; halogenated hydrocarbon solvents such as methylene chloride, chloroform and dichloroethane; dioxane, Ketone solvents such as tetrahydrofuran, methyl isobutyl ketone, cyclohexanone and isophorone; ester solvents such as ethyl acetate, butyl acetate, ethylene glycol monoethyl ether acetate and 2-methoxypropyl acetate; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, Ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether What alkylene glycol
  • the particle-containing composition can be directly prepared by kneading with the dispersant, particles, polymer, organic solvent and the like of the present invention.
  • the dispersant, particles, polymer, organic solvent and the like of the present invention after being in the form of so-called particle dispersion base, it is possible to use a polymer, an organic solvent and the like to make a particle-containing composition.
  • the particle dispersion base and the particle-containing composition are prepared by dispersing the necessary component materials using a rotation / revolution mixer, a roll mill, a ball mill, a sand ground mill, a paint shaker, a kneader, a dissolver, an ultrasonic dispersion machine, etc. May be In this case, the treated particles may be kneaded with the polymer, or an integral blending method in which the dispersant, the pigment and the polymer are simultaneously kneaded may be used.
  • the particle dispersion base and the particle-containing composition can be used as a paint or printing ink by further adding a binder polymer (resin or rubber) or another polymer, and can be used as a paint or printing ink as it is.
  • a binder polymer resin or rubber
  • the dispersant is preferably contained in an amount of 1 to 200% by mass (in terms of polylysine derivative) based on the pigment.
  • the particle-containing composition can also be used as a coating film or a film-like composition.
  • the application of the particle-containing composition is not particularly limited, and can be used for resin or rubber products containing the above-mentioned particles, for example, cosmetics (cosmetics), paints, ink compositions, liquid developers, anti-blocking agents Coating materials (colored coatings, conductive coatings, antistatic coatings etc.), ceramic slurries, conductive additives such as battery electrodes, dry toners for copying, liquid toners for copying, ceramic molded bodies, bonded magnets, copying machines, etc. Rubber magnets, magnetic tapes, color plastic molded articles used for household goods and building materials, sealing agents used for construction, etc.
  • cosmetics cosmetics
  • paints ink compositions
  • liquid developers liquid developers
  • anti-blocking agents Coating materials colored coatings, conductive coatings, antistatic coatings etc.
  • ceramic slurries such as battery electrodes, dry toners for copying, liquid toners for copying, ceramic molded bodies, bonded magnets, copying machines, etc.
  • the cosmetic include basic cosmetics such as creams, emulsions, lotions, and cosmetic solutions, soaps, hair washes, body shampoos, shampoos, rinses, hair tonics, hair care products such as hair setting agents, foundations, eyeliners, mascaras And make-up cosmetics such as lipstick, and mouth products such as mouthwash and toothpaste.
  • the cosmetic preferably contains an additive such as a stabilizer, an antioxidant, a plasticizer, a UV absorber, and a dispersing aid to the extent that the effect of the present invention is not impaired.
  • the polylysine derivative has little influence on the skin of the human body, and the particle-containing composition can be used as a cosmetic because of its high particle dispersibility.
  • the content of the particle-containing composition contained in the cosmetic is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, still more preferably 0.5% by mass with respect to the entire components contained in the cosmetic. It is mass% or more.
  • the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less, and still more preferably 30% by mass or less.
  • the paint include colored paint, conductive paint, antistatic paint and the like.
  • Specific examples of the ink composition include printing ink, conductive ink and the like.
  • the paint or ink composition preferably contains additives such as a stabilizer, an antioxidant, a plasticizer, a UV absorber, and a dispersion aid to the extent that the effects of the present invention are not impaired.
  • the liquid developer is a suspension of toner particles in a dielectric liquid and can be used in the electrophoretic development method.
  • the liquid developer is prepared by mixing functional particles, carbon black, organic pigments, inorganic pigments, etc. with resins that impart chargeability and fixability, adding a polylysine derivative, and suspending in a dielectric liquid, etc. It can be produced by particleizing and forming a particle-containing composition containing a polylysine derivative. In addition, it is preferable to use a dispersant, a charge control agent, a stabilizer and the like in combination as necessary. Since the liquid developer uses the particle-containing composition containing the polylysine derivative, the liquid developer exhibits excellent particle dispersibility and electrophoresis, and the particles in the liquid developer migrate smoothly without aggregation.
  • the average particle diameter of the toner particles is preferably 20 ⁇ m or less, more preferably 15 ⁇ m or less, and still more preferably 10 ⁇ m or less, 5 ⁇ m or less, or 3 ⁇ m or less.
  • the lower limit is preferably 0.01 ⁇ m or more, more preferably 0.05 ⁇ m or more, and still more preferably 0.1 ⁇ m or more.
  • the average particle size can be measured, for example, using a digital microscope.
  • the antiblocking agent is used to impart unevenness to the film by kneading or coating the film, and to suppress adhesion between the films (antiblocking). Since the particle-containing composition has high particle dispersibility, high antiblocking properties can be obtained even with a small amount, and appearance defects due to particle aggregation can be suppressed.
  • the acid value of the polyester is obtained by adding a polyester solution prepared by dissolving 0.5 g of polyester in 40 mL of a xylene (ortho, meta, para mixture) / ethanol mixed solution (1/1 mass ratio), potassium hydroxide ethanol solution ( It titrated with 0.1 mol / L), and measured by reading the color change point by a phenolphthalein digit.
  • Synthesis Example 1 Synthesis of Polyester PES-1 100 parts of 12-hydroxystearic acid (trade name: 12-hydro acid (manufactured by Kokura Synthetic Industry Co., Ltd.)) in a reaction flask equipped with a thermometer, a stirrer, a nitrogen inlet, a reflux condenser, a water separator, and a vacuum outlet After charging, the reaction was performed at 150 ° C. for 3 hours under a nitrogen atmosphere, and then heated at 200 ° C. for 2 hours under reduced pressure. Then, it was cooled to room temperature to obtain a reaction product (referred to as “polyester PES-1”). The acid value of polyester PES-1 was 50.0 mg KOH / g, and the calculated molecular weight was 1120.
  • Synthesis Example 2 Synthesis of Polyester PES-2
  • 12hydroxystearic acid trade name: 12-hydro acid (manufactured by Kokura Synthetic Industry Co., Ltd.)
  • polyhydro acid manufactured by Kokura Synthetic Industry Co., Ltd.
  • the acid value of polyester PES-2 was 32.0 mg KOH / g, and the calculated molecular weight was 1750.
  • Synthesis Example 3 Synthesis of Polyester PES-3
  • 10 parts of 12-hydroxystearic acid, 35 parts of ⁇ -caprolactone (manufactured by Junsei Chemical Co., Ltd.) and 0.1 parts of tetrabutyltitanate are charged, and it is applied for 2 hours to 160 ° C. under a nitrogen stream. After heating at 160 ° C. for 4 hours, heating was carried out until the residual amount of ⁇ -caprolactone was 1% or less. It was then cooled to room temperature to obtain polyester PES-3.
  • the acid value of polyester PES-3 was 41.5 mg KOH / g, and the calculated molecular weight was 1352.
  • Synthesis Example 4 Synthesis of Polyester PES-4
  • 10 parts of 12-hydroxystearic acid, 190 parts of ⁇ -caprolactone (manufactured by Junsei Chemical Co., Ltd.) and 0.1 parts of tetrabutyltitanate are charged, and it is applied for 2 hours to 160 ° C. under nitrogen stream. After heating at 160 ° C. for 4 hours, heating was carried out until the residual amount of ⁇ -caprolactone was 1% or less. It was then cooled to room temperature to obtain polyester PES-4.
  • the acid value of polyester PES-4 was 8.5 mg KOH / g, and the calculated molecular weight was 6580.
  • Example 1 PLIS-1 (manufactured by Foodchem International Corporation, ⁇ -poly-lysine ( ⁇ -polylysine), weight average molecular weight 3600 to 4300) was treated with HH-type strong base anion exchange resin SA10AOH (manufactured by Mitsubishi Chemical Corporation) and purified An aqueous solution of 25% ⁇ -polylysine was obtained.
  • Example 2 to 16 In Example 1, as shown in the following table, the type and amount of polyester were changed to different polyesters. Polylysine derivatives 2 to 16 were obtained in the same manner as in Example 1 except for the above matters.
  • the resulting pigment dispersion is diluted 1000 times with light liquid paraffin, the average particle size is measured by the dynamic light scattering method using Zetasizer Nano ZSP (manufactured by Malvern Instruments Ltd), and the dispersibility is based on the following criteria: It evaluated by. :: Average particle diameter after dispersion is less than 200 nm ⁇ : Average particle diameter after dispersion is 200 nm or more and less than 400 nm ⁇ : Average particle diameter after dispersion is 400 nm or more and less than 600 nm
  • the obtained pigment dispersion is diluted 1000 times with light liquid paraffin, the average particle diameter is measured by the dynamic light scattering method using Zetasizer Nano ZSP (manufactured by Malvern Instruments Ltd), and the dispersibility is based on the following criteria. evaluated. :: Average particle diameter after dispersion is less than 200 nm ⁇ : Average particle diameter after dispersion is 200 nm or more and less than 400 nm ⁇ : Average particle diameter after dispersion is 400 nm or more and less than 600 nm

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  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)
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  • Polyesters Or Polycarbonates (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)

Abstract

L'invention concerne : un nouveau dérivé de polylysine ; et un dispersant, des particules traitées, une composition contenant des particules et un produit cosmétique qui contient le dérivé de polylysine. La présente invention porte sur : un dérivé de polylysine présentant un polyester dans une chaîne latérale ; et un dispersant, des particules traitées, une composition contenant des particules et un produit cosmétique qui contient le dérivé de polylysine.
PCT/JP2018/032749 2017-09-05 2018-09-04 Dérivé de polylysine WO2019049862A1 (fr)

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JPH07109339A (ja) * 1993-08-20 1995-04-25 Nippon Paint Co Ltd 生分解性樹脂組成物及び防汚塗料組成物
JPH0770311A (ja) * 1993-09-06 1995-03-14 Yamanouchi Pharmaceut Co Ltd ポリ−ε−置換−Ｌ−リジンのＤ−ガラクトピラノシル−グルコン酸誘導体
JP2000511189A (ja) * 1996-05-24 2000-08-29 マサチューセッツ インスティテュート オブ テクノロジー 肺への薬物送達のための空気力学的に軽い粒子
JP2001525357A (ja) * 1997-12-12 2001-12-11 サミアン・コーポレーション 遺伝子輸送のための生物分解性の混合重合体ミセル
JP2004507600A (ja) * 2000-08-30 2004-03-11 コーネル　リサーチ　ファンデイション　インコーポレイテッド エラストマー機能性の生分解性コポリエステルアミドおよびコポリエステルウレタン
JP2009520040A (ja) * 2005-12-19 2009-05-21 ファーマイン コーポレーション 治療薬の送達のための疎水性コアの担体組成物、及び同担体組成物の作製法及び使用法
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JP2013524940A (ja) * 2010-04-19 2013-06-20 アボット カーディオヴァスキュラー システムズ インコーポレイテッド 乳酸のポリマーを含む移植可能なデバイスのためのコーティング及びそれを製造する方法
CN105418944A (zh) * 2015-12-11 2016-03-23 中国科学院长春应用化学研究所 一种微珠及其制备方法和应用
JP2017203143A (ja) * 2016-05-13 2017-11-16 味の素株式会社 ポリアリルアミン誘導体

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