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ES247862A1 - New monomeric, polymerisable, ultra-violet light-screening esters and amides, their polymerisation and use - Google Patents

New monomeric, polymerisable, ultra-violet light-screening esters and amides, their polymerisation and use

Info

Publication number
ES247862A1
ES247862A1 ES0247862A ES247862A ES247862A1 ES 247862 A1 ES247862 A1 ES 247862A1 ES 0247862 A ES0247862 A ES 0247862A ES 247862 A ES247862 A ES 247862A ES 247862 A1 ES247862 A1 ES 247862A1
Authority
ES
Spain
Prior art keywords
ester
ultra
acids
group
polymerizable
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
ES0247862A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG, Ciba AG filed Critical Ciba Geigy AG
Publication of ES247862A1 publication Critical patent/ES247862A1/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/20—Esters containing oxygen in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/22—Esters containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/36—Amides or imides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having amino or quaternary ammonium groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/08—After-treatment with organic compounds macromolecular

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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)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Ultra-violet light-screening polymers are obtained by the polymerization of a monomeric U.V.-absorbing ester or amide which has been prepared by reacting an acid halide of a polymerizable aliphatic mono- or dicarboxylic acid with a U.V.-absorbing compound containing at least one benzene ring and a grouping attached thereto which together form a conjugated system the said compound containing at least one hydroxyl or amino group capable of reacting with an acid halide without losing its U.V.-absorbing properties said compound, and said monomeric ester or amide, having a molecular extinction coefficient (measured in ethanol) of at least 10,000 in the range 240-400 mm . Specified polymerizable acids for the preparation of the monomers are acrylic, crotonic, methacrylic, chloroacrylic, itaconic, fumaric and maleic acids specified U.V.-absorbing hydroxy- and amino-compounds are those of the formul <FORM:0898065/IV (a)/1> where R8 is a benzene, diphenyl or pyridine residue <FORM:0898065/IV (a)/2> where A is an aliphatic hydrocarbon radical R9-R10-NH2, where R9 is a benzthiazole, benzoxazole or benzimidazole residue bound in 2-position to R10, which is a benzene residue bound in 4-position to the amino group A-O-COR10NH2, where A is an alkyl group and R10 is a benzene residue bound in 1-position to the -OCO- group and in 4-position to the amino group and 7-aminocoumarins (see Group IV(b)). The monomers may be homopolymerized or copolymerized, in bulk, in organic solution or in emulsion. Suitable monomers for copolymerization contain the group CH2=C<, such as vinyl esters of organic acids (e.g. the acetate, formate, butyrate or benzoate) vinyl alkyl ketones vinyl halides such as vinyl and vinylidene chloride styrene and substituted styrenes acrylic acid esters acrylonitrile acrylamide substituted amides of acrylic, methacrylic, chloroacrylic, maleic and fumaric acids olefines, such as isobutylene, butadiene 2-chlorobutadiene heterocyclic compounds such as N-vinylcarbazole, N-vinylimidazole, vinylpyrrolidone and vinylpyridine unsaturated ethers such as vinyl and isobutylvinyl ethers acids such as acrylic and methacrylic acids. One or more such polymerizable compounds may be used to prepare copolymers with the U.V.-absorbing ester or amide. The polymers are used for impregnating or coating, e.g. coating wood surfaces, paper, textiles and laminates. Specifications 880,549 and 893,236 are referred to.ALSO:The invention comprises monomeric polymerizable ultra-violet light-screening esters or amides which retain their light-screening properties on polymerization, and which have been obtained by reacting an acid halide of a polymerizable aliphatic mono- or dicarboxylic acid with an ultra-violet light-absorbing compound containing at least one benzene ring and a grouping attached thereto which together form a conjugated system, the said compound containing at least one hydroxyl or amino group capable of reacting with an acid halide without losing its ultra-violet light-screening properties said compound, and also the ester or amide derived therefrom by reaction with the polymerizable acid halide, having a molecular extinction coefficient (measured in ethanol) of at least 10,000 in the range 240-400 mm . Specified polymerizable acids are acrylic, crotonic, methacrylic, chloroacrylic, itaconic, fumaric and maleic acids. Specified types of ultra-violet screening hydroxy-and amino-compounds are those of the formulae <FORM:0898065/IV (b)/1> where R8 is a benzene, diphenyl or pyridine residue <FORM:0898065/IV (b)/2> where A is an aliphatic hydrocarbon residue R9-R10-NH2, where R9 is a benzthiazole, benzoxazole or benzimidazole residue bound in 2-position to R10 and R10 is a benzene residue bound in 4-position to the amino group A-O-CO-R10-NH2, where A is an alkyl group and R10 is a benzene residue bound in 1-position to the -OCO-group and in 4-position to the amino group and 7-aminocoumarins. Examples prepare the compounds of the formulae <FORM:0898065/IV (b)/3> Specifications 880,549 and 893,236 are referred to.ALSO:Textiles are protected against ultra-violet light by treatment with a polymerisable u.v.-absorbing ester or amide (see Group IV (b)) or with a homopolymer or copolymer thereof (see Group IV (a) or dyed textiles can be similarly protected by a screen of such a polymer. In Examples (33) a polyamide fabric is treated with the ester <FORM:0898065/IV (c)/1> in ethanol in the presence of a reaction product from octadecyl alcohol and ethylene oxide (34) as in (33) in the presence of formic acid also (35) polyamide fibre yarn is similarly treated (36) wool gaberdine dyed with a commercial acid wool dye is protected against u.v-light by an acetylcellulose film containing the ester <FORM:0898065/IV (c)/2> (38) bleached jute is coated with an emulsion obtained by polymerising the ester <FORM:0898065/IV (c)/3> and dried (41) a polyamide fabric dyed with the dyestuff <FORM:0898065/IV (c)/4> is coated with the emulsion used in (38) and dried (42) wool serge dyed with the above dyestuff is protected against u.v. light by a glass plate coated with the emulsion used in (38). Specifications 880,549 and 893,236 are referred to.
ES0247862A 1958-03-13 1959-03-12 New monomeric, polymerisable, ultra-violet light-screening esters and amides, their polymerisation and use Expired ES247862A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH5702458A CH376899A (en) 1958-03-13 1958-03-13 Process for the production of new polymerizable carboxylic acid esters

Publications (1)

Publication Number Publication Date
ES247862A1 true ES247862A1 (en) 1959-10-16

Family

ID=4520867

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0247862A Expired ES247862A1 (en) 1958-03-13 1959-03-12 New monomeric, polymerisable, ultra-violet light-screening esters and amides, their polymerisation and use

Country Status (8)

Country Link
BE (1) BE576615A (en)
CH (2) CH376899A (en)
DE (1) DE1420282B2 (en)
ES (1) ES247862A1 (en)
FR (1) FR1229803A (en)
GB (1) GB898065A (en)
NL (2) NL237021A (en)
SE (1) SE314352B (en)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3344127A (en) * 1964-07-30 1967-09-26 Monsanto Co Dyeable polymers of acrylonitrile with p-acrylamidobenzoic acids or salts thereof
EA027642B1 (en) * 2012-08-27 2017-08-31 ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи Stabilized aqueous water clarifier composition and methods of use thereof
EP2878606B1 (en) 2013-11-29 2015-08-05 ICAP-SIRA S.p.A. UV-curable composition and pressure sensitive adhesive having breathability derived therefrom, as well as method for manufacturing the same
US10150832B2 (en) 2013-12-06 2018-12-11 Lg Chem, Ltd. Block copolymer
JP6521974B2 (en) 2013-12-06 2019-05-29 エルジー・ケム・リミテッド Block copolymer
EP3078695B1 (en) 2013-12-06 2020-11-04 LG Chem, Ltd. Block copolymer
CN105873969B (en) 2013-12-06 2018-09-04 株式会社Lg化学 Block copolymer
WO2015084132A1 (en) 2013-12-06 2015-06-11 주식회사 엘지화학 Block copolymer
EP3078654B1 (en) 2013-12-06 2021-07-07 LG Chem, Ltd. Monomer and block copolymer
US10239980B2 (en) 2013-12-06 2019-03-26 Lg Chem, Ltd. Block copolymer
CN105960422B (en) 2013-12-06 2019-01-18 株式会社Lg化学 Block copolymer
WO2015084128A1 (en) 2013-12-06 2015-06-11 주식회사 엘지화학 Block copolymer
CN105934454B (en) 2013-12-06 2019-01-18 株式会社Lg化学 Block copolymer
JP6483693B2 (en) 2013-12-06 2019-03-13 エルジー・ケム・リミテッド Block copolymer
WO2015084123A1 (en) 2013-12-06 2015-06-11 주식회사 엘지화학 Block copolymer
CN105899557B (en) 2013-12-06 2018-10-26 株式会社Lg化学 Block copolymer
CN105934455B (en) 2013-12-06 2019-01-18 株式会社Lg化学 Block copolymer
WO2016053007A1 (en) 2014-09-30 2016-04-07 주식회사 엘지화학 Method for producing patterned substrate
WO2016053001A1 (en) 2014-09-30 2016-04-07 주식회사 엘지화학 Block copolymer
WO2016053014A1 (en) 2014-09-30 2016-04-07 주식회사 엘지화학 Method for producing patterned substrate
JP6524220B2 (en) 2014-09-30 2019-06-05 エルジー・ケム・リミテッド Block copolymer
CN107075053B (en) 2014-09-30 2019-05-21 株式会社Lg化学 Block copolymer
EP3214102B1 (en) 2014-09-30 2022-01-05 LG Chem, Ltd. Block copolymer
US10703897B2 (en) 2014-09-30 2020-07-07 Lg Chem, Ltd. Block copolymer
WO2016053010A1 (en) 2014-09-30 2016-04-07 주식회사 엘지화학 Block copolymer
JP6532941B2 (en) 2014-09-30 2019-06-19 エルジー・ケム・リミテッド Block copolymer
CN107075028B (en) 2014-09-30 2020-04-03 株式会社Lg化学 Block copolymer
CN111825798B (en) * 2020-07-27 2022-06-28 东来涂料技术（上海）股份有限公司 Preparation method of high-molecular ultraviolet light absorber

Also Published As

Publication number Publication date
CH383001A (en) 1964-10-15
SE314352B (en) 1969-09-08
NL112461C (en)
DE1420282B2 (en) 1971-10-28
NL237021A (en)
DE1420282A1 (en) 1968-10-17
GB898065A (en) 1962-06-06
FR1229803A (en) 1960-09-09
BE576615A (en)
CH376899A (en) 1964-04-30

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