EP3055339A1 - (méth)acrylates d'uréthane polyfonctionnels à base de produits de monoaddition de diisocyanates pauvres en monomères - Google Patents

(méth)acrylates d'uréthane polyfonctionnels à base de produits de monoaddition de diisocyanates pauvres en monomères

Info

Publication number
EP3055339A1
EP3055339A1 EP14777320.4A EP14777320A EP3055339A1 EP 3055339 A1 EP3055339 A1 EP 3055339A1 EP 14777320 A EP14777320 A EP 14777320A EP 3055339 A1 EP3055339 A1 EP 3055339A1
Authority
EP
European Patent Office
Prior art keywords
diisocyanate
meth
urethane
hexahydro
acrylates
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.)
Withdrawn
Application number
EP14777320.4A
Other languages
German (de)
English (en)
Inventor
Emmanouil Spyrou
Holger Loesch
Marion EWALD
Laura RAMON-GIMENEZ
Andrea THESING
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.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
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 Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP3055339A1 publication Critical patent/EP3055339A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1808—Catalysts containing secondary or tertiary amines or salts thereof having alkylene polyamine groups
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
    • C08G18/4269—Lactones
    • C08G18/4277—Caprolactone and/or substituted caprolactone
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4829—Polyethers containing at least three hydroxy groups
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
    • C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
    • C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes

Definitions

  • the invention relates to polyfunctional urethane (meth) acrylates from monomer poor
  • polymerizable resins usually consist of hydroxyl-containing resins, diisocyanates and compounds containing both an alcohol group and an activated double bond, eg. B. hydroxyethyl acrylate (HEA).
  • HOA hydroxyethyl acrylate
  • Urethane (meth) acrylates are characterized in the cured coating by an excellent balance between hardness and flexibility.
  • urethane acrylates A major disadvantage of such urethane acrylates is their high viscosity, especially if they are based on higher functionality alcohols (functionality> 3). Due to the high viscosity, the application in radically polymerizable coating systems,
  • the object of the present invention was to find higher-functionality urethane (meth) acrylates which have at least 30% lower viscosity than conventional products. Both the intrinsic viscosity and the viscosity in solution are important.
  • the object has been achieved by the use of monomer-poor adducts of diisocyanates and compounds containing both an alcohol group and an activated double bond in the urethane (meth) acrylate preparation.
  • Tg glass transition points
  • these Tg can range from temperatures well below 0 ° C to well over 100 ° C (eg for powder coating applications). If one tries to modify such a hydroxy-functional resin in a radiation-curable resin, for. As by the reaction with diisocyanates and HEA, the viscosity of the final product depends primarily on the Tg of the starting resin. But if you try based on one certain OH resin to achieve the lowest possible viscosity, the inventive method offers significant advantages over the prior art.
  • the invention relates to urethane (meth) acrylates, from the reaction product of
  • component B) at least one resin component having at least three OH groups per molecule; wherein on each OH group of component B) 0.2 to 1, 1 NCO equivalents of component A) is omitted.
  • Alcohol group as well as an activated double bond contained have already been described in EP 2 367 864 and in EP 1 179 555. They are usually prepared so that an excess of diisocyanate with a compound containing both an alcohol group and an activated double bond, for. As hydroxyethyl, completely at temperatures between 40 - 80 ° C is reacted. Thereafter, the excess diisocyanate is separated by distillation, usually in a thin-layer or a short-path evaporator. Frequently, special inhibitors must be used for this purpose and, in addition, special distillation conditions must be maintained so that the residue does not polymerize.
  • isocyanates a1) are aliphatic, cycloaliphatic and araliphatic, d. H.
  • aryl-substituted aliphatic diisocyanates as used, for example, in Houben-Weyl, Methods of Organic Chemistry, Volume 14/2, pages 61-70 and in the article by W. Siefken,
  • TMDI Trimethyl-1,6-hexamethylene diisocyanate
  • TMDI 2,4,4-trimethyl-1,6-hexamethylene diisocyanate
  • TMDI 1,9-diisocyanato-5-methylnonane
  • 1,8-diisocyanato-2,4 dimethyloctane 1,1-dodecane diisocyanate
  • ⁇ , ⁇ '-diisocyanatodipropyl ether cyclobutene-1,3-diisocyanate
  • cyclohexane-1,3-diisocyanate cyclohexane-1,4-diisocyanate
  • the enumerated diisocyanates can be used alone or in any desired mixtures.
  • Aliphatic and cycloaliphatic diisocyanates are particularly preferably used, selected from IPDI, HDI, TMDI, and H 12 MDI (pure H 12 MDI isomers or their
  • Suitable preferred reactive olefinic compounds a2) are all compounds which carry both at least one methacrylate or acrylate function or vinyl ether group, as well as exactly one hydroxyl group.
  • Other ingredients may include aliphatic,
  • Hydroxyhexyl Of course, mixtures can also be used. Hydroxyethyl acrylate is particularly preferably used.
  • reaction of polyisocyanates with reactive olefinic compounds involves the reaction of the free NCO groups with hydroxyl groups and has become common
  • organometallic compounds such as. Dibutyltin dilaurate (DBTL)
  • DBTL Dibutyltin dilaurate
  • the NCO / OH ratio is 2: 1 to 40: 1, preferably 2: 1 to 9.8: 1 and more preferably 3: 1 to 8: 1. This corresponds to a reaction of 1 to 20 mol, preferably 1 to 4.9 mol, more preferably 1 to 5 mol of diisocyanate A), with 1 mol of a reactive olefinic compound a2).
  • the content of free diisocyanate of less than 5 wt .-%, preferably less than 1 wt .-% and particularly preferably less than 0.5 wt .-%, on.
  • Compounds containing both an alcohol group and an activated double bond have a content of free diisocyanate of less than 5 wt .-%, preferably less than 1 wt .-% and particularly preferably less than 0.5 wt .-%, on.
  • Monoadducts a content of free NCO of 10.4 - 16.4 wt .-% to.
  • Suitable resin components having at least three OH groups per molecule B) are polyesters, polycaprolactones, polyethers, poly (meth) acrylates, polycarbonates and polyurethanes, and also monomeric polyols having an OH functionality> 3 and an OH number from 5 to 2000 mg KOH / gram and an average molecular weight of 92 to 30,000 g / mol. Preference is given to using polyols having an OH number of 30 to 200 mg KOH / gram and an average molecular weight of 840 to 5600 g / mol. Particularly preferred polyols are polyesters and / or polyethers.
  • the amount of resin component B) containing OH groups is selected so that 0.2 to 1.1 NCO equivalents of component A) are eliminated for each OH group of component B).
  • the invention also provides a process for the preparation of
  • component A) involves the reaction of the free NCO groups with hydroxyl groups and has been described frequently
  • Reaction can take place either with solvent, but also preferably without solvent. It is usually carried out in a temperature range between 40 and 80 ° C and can be advantageously by conventional catalysts known in urethane, such.
  • Suitable reaction units are all customary apparatus, boilers, static mixers, extruders, etc., preferably
  • the viscosity in substance is measured at a suitable temperature between RT and 100 ° C according to DIN EN ISO 3219.
  • the viscosity in solution is in a suitable
  • Solvents e.g. B. in a reactive diluent, measured at 23 ° C according to DIN EN ISO 3219.
  • Suitable reactive diluents are all common liquid components which carry at least one polymerizable group, for. Acrylates, methacrylates, vinyl ethers, etc. Examples of such reactive diluents are hexanediol diacrylate,
  • the invention also provides the use of the urethane acrylates described in radiation-curing formulations of all kinds.
  • the mixture is then saturated with dry air and the unreacted diisocyanate by short path distillation (KDL 4, UIC GmbH, Alzenau -Hoerstein) with 200 g / h at 150 ° C and 2 mbar separated, with a steady influx of dry air in countercurrent passed through the apparatus.
  • KDL 4 UIC GmbH, Alzenau -Hoerstein
  • the product has an NCO content of 12.0 wt .-% and a monomer content of 0.3 wt .-%.
  • the solvent is completely removed in vacuo.
  • the viscosity at 100 ° C is 57 Pas.
  • the viscosity 30% in HDDA is 0.07 Pas.
  • trifunctional polyols is significantly lower when low-monomer IPDI-HEA is used, it is now shown that the viscosity of difunctional polyols is about the same.

Abstract

L'invention concerne des (méth)acrylates d'uréthane polyfonctionnels à base de produits de monoaddition de diisocyanates pauvres en monomères.
EP14777320.4A 2013-10-08 2014-09-30 (méth)acrylates d'uréthane polyfonctionnels à base de produits de monoaddition de diisocyanates pauvres en monomères Withdrawn EP3055339A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE201310220239 DE102013220239A1 (de) 2013-10-08 2013-10-08 Polyfunktionelle Urethan(meth)acrylate aus Monomer armen Diisocyanat-Monoaddukten
PCT/EP2014/070853 WO2015052038A1 (fr) 2013-10-08 2014-09-30 (méth)acrylates d'uréthane polyfonctionnels à base de produits de monoaddition de diisocyanates pauvres en monomères

Publications (1)

Publication Number Publication Date
EP3055339A1 true EP3055339A1 (fr) 2016-08-17

Family

ID=51628130

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14777320.4A Withdrawn EP3055339A1 (fr) 2013-10-08 2014-09-30 (méth)acrylates d'uréthane polyfonctionnels à base de produits de monoaddition de diisocyanates pauvres en monomères

Country Status (8)

Country Link
US (1) US20160251472A1 (fr)
EP (1) EP3055339A1 (fr)
JP (1) JP2016540063A (fr)
KR (1) KR20160068854A (fr)
CN (1) CN105745241A (fr)
DE (1) DE102013220239A1 (fr)
TW (1) TW201529684A (fr)
WO (1) WO2015052038A1 (fr)

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KR20180129977A (ko) 2013-07-30 2018-12-05 메르크 파텐트 게엠베하 전자 소자용 물질
EP3263616B8 (fr) 2016-06-27 2020-01-15 Evonik Operations GmbH Moyens de revêtement fonctionnalisés par un alkoxysilane et contenant un allophanate
WO2018087158A1 (fr) * 2016-11-11 2018-05-17 Evonik Degussa Gmbh Polyesters réticulables par irradiation et leur utilisation
EP3489268A1 (fr) * 2017-11-23 2019-05-29 Allnex Belgium, S.A. Composition durcissable par rayonnement
EP3656798A1 (fr) * 2018-11-23 2020-05-27 Evonik Operations GmbH Prépolymères nco peu visqueux à faible taux de monomères résiduels
FR3090641B1 (fr) * 2018-12-19 2022-02-11 Bostik Sa Composition (méth)acrylique comprenant un polyuréthane modifié
CN110343231B (zh) * 2019-06-19 2022-03-08 黎明化工研究设计院有限责任公司 一种单官能度聚氨酯丙烯酸单体及其制备方法
CN113462344A (zh) * 2021-06-04 2021-10-01 武汉海翎化学工业有限公司 一种高黏度热固化型聚氨酯胶粘剂及其制备方法
CN114835889A (zh) * 2022-05-13 2022-08-02 深圳市百利合新材料发展有限公司 超支化聚合物分子结构、制备方法以及基于超支化聚合物的光刻胶

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KR20160068854A (ko) 2016-06-15
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CN105745241A (zh) 2016-07-06
WO2015052038A1 (fr) 2015-04-16
JP2016540063A (ja) 2016-12-22
DE102013220239A1 (de) 2015-04-23

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