WO2012123403A1 - Système résine époxy permettant un contrôle visuel de l'état de prise - Google Patents

Système résine époxy permettant un contrôle visuel de l'état de prise Download PDF

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Publication number
WO2012123403A1
WO2012123403A1 PCT/EP2012/054255 EP2012054255W WO2012123403A1 WO 2012123403 A1 WO2012123403 A1 WO 2012123403A1 EP 2012054255 W EP2012054255 W EP 2012054255W WO 2012123403 A1 WO2012123403 A1 WO 2012123403A1
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WO
WIPO (PCT)
Prior art keywords
epoxy resin
resin system
epoxy
group
dye
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.)
Ceased
Application number
PCT/EP2012/054255
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German (de)
English (en)
Inventor
Andreas LÜHRING
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.)
Fraunhofer-Gesellschaft zur Förderung der Angewandten Forschung eV
Original Assignee
Fraunhofer-Gesellschaft zur Förderung der Angewandten Forschung eV
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 Fraunhofer-Gesellschaft zur Förderung der Angewandten Forschung eV filed Critical Fraunhofer-Gesellschaft zur Förderung der Angewandten Forschung eV
Publication of WO2012123403A1 publication Critical patent/WO2012123403A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • C09B67/0009—Coated particulate pigments or dyes with organic coatings containing organic acid derivatives
    • C09B67/001—Coated particulate pigments or dyes with organic coatings containing organic acid derivatives containing resinic acid derivatives
    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins

Definitions

  • the present invention relates to an epoxy resin system which includes a dye which indicates the course or the end point of the curing of the epoxy resin as the epoxy resin system is cured by color change.
  • the invention further relates to components which are coated with an epoxy resin system according to the invention and also describes the use of the epoxy resin system as a thermally curable adhesive.
  • a method is defined for indicating the course or end point of the curing reaction of an epoxy resin system.
  • the present invention describes the use of a reacting with an epoxy resin system with color change dye as an indicator for the course or, the end point of the curing of an epoxy resin system,
  • One-component epoxy adhesives consist in most cases of an epoxy resin and a curing agent which is reacted at temperatures well above the storage temperature of the adhesive. At the storage temperature of the adhesive, the hardener reacts only very slowly. The storage stability of such adhesives is limited. The curing state of the adhesive Stoffes can often only be determined with elaborate analytical methods.
  • thermosetting adhesive which is based on an epoxy resin.
  • This adhesive composition includes an anhydride curing agent and a dye that forms a reversible complex with the anhydride curing agent. The dye changes its color as soon as the anhydride hardener is used up.
  • an epoxy resin composition which is based on aliphatic and cycloaliphatic amines as a curing agent.
  • This composition may include a dye.
  • an indication of the curing process is not mentioned in this patent application.
  • thermosetting epoxy resin system which comprises the following constituents: a) at least one epoxy resin,
  • At least one curing agent or accelerator for the epoxy resin selected from the group consisting of imidazole derivatives, aziridine derivatives, triazine derivatives, imidazoline derivatives, o-tolylbiguanide, cyclic amidines, substituted guanidines, dicyandiamide, aromatic amines, room temperature solid polyamines and / or mixtures thereof, wherein the at least one curing agent or accelerator for the epoxy resin to at least 0.2 wt., Based on the total epoxy resin system is included, as well as
  • an epoxy resin adhesive containing a dye which changes color with the progress of curing of the adhesive By using an epoxy resin adhesive containing a dye which changes color with the progress of curing of the adhesive, a visualization of the progress of the curing, the curing state and the further processability can be made visually.
  • precoated adhesives are solid adhesives, so that an overlay is not even recognizable by increasing solidification.
  • Components which include a precoated epoxy resin, which preferably forms a solid layer, are e.g. Adhesive bolts and other fasteners or reinforcing sheets to be fastened by gluing.
  • dyes which can react with the epoxy resin with color change ie have a reactivity to epoxy resins, the reaction with the epoxy resins causes the color change. It has been found that dyes which have, for example, amino groups, such as Sudan Red 7b,
  • Dyes present as the ammonium or sulfonic acid salt are generally not or only sparingly soluble in organic systems. Thus, when using the ionic dye Ponceau BS (Acid Red 66) no
  • Ponceau BS (Acid Red 66)
  • Particularly preferred dyes are nonionic dyes which have an -OH functionality, ie hydroxyl group-containing dyes.
  • Epoxy resin system according to claim 1 characterized in that
  • the at least one epoxy resin to 20. to 99 parts by weight, preferably 40 to 95 wt .-%, particularly preferably 50 to 60 wt .-%, based on the total epoxy resin, and / or b) the at least one Hardener or accelerator for the epoxy resin to at least 0.2 to 30 wt .-%, preferably 2 to 10 wt .-%, particularly preferably 3 to 6 wt .-%, based on the total epoxy resin system,
  • the at least one dye is selected from the group consisting of at least one -OH functionality having azo dyes, Triphenylmethanfarbstoffen, anthraquinone dyes, xanthenfarbstoffen, phthalein dyes and / or mixtures thereof.
  • Particularly preferred azo dyes are selected from the group consisting of 1-phenylazo-naphthalene-2-ol ⁇ Sudan * I), 1- (2,4-dimethyl-phenylazo) -naphthalen-2-ol (Sudan * II), l - (4-phenylazo-phenylazo) -naphthalene-2-ol (Sudan * III), 1- (2-methyl-4-o-tolylazo-phenylazo) -naphthalen-2-ol (Sudan * IV), 1- [ 4- (3-methylphenylazo) -3-methylphenylazo] naphthalen-2-ol (Sudan * Red B), 1- (2-methoxy-phenylazo) -naphthalen-2-ol (Sudan * Red G), 4-phenylazo resorcinol (Sudan * Orange G), 4 - [[4- (phenylazo) -l-naphthalenyl] azo] phenol (
  • Preferred representatives of the triphenylmethane dyes are selected from the group consisting of 4- [bis (4-hydroxyphenyl) methylene] -2,5-cyclohexadienone (aurin), phenolphthalein, thymolphthalein and / or mixtures thereof.
  • anthraquinone dyes are selected from the group consisting of 1,2-dihydroxyanthraquinone ⁇ alizarin), 1,2,3-trihydroxyanthraquinone
  • Alizarin R 1,2,4-trihydroxyanthraquinone (purpurin), 1,2,5,8-tetrahydroxyanthraquinone (alizarin Bordeaux, quinalizarin) and / or mixtures thereof.
  • the at least one of dye based on the total weight of components a) and b), from 0.001 to 0.5 wt .-%, preferably from 0.005 to 0.25 wt .-%, particularly before ⁇ Trains t from 0.01 to 0.05 wt .-%.
  • Particularly preferred hardeners are imidazole hardeners, ie hardeners based on imidazole derivatives.
  • imidazole derivatives are selected from the group consisting of 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, l Benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2 -phenylimidazole, 1-cyanoethyl-2-undecylimidazolium-trimellitate, 1-cyanoethyl-2-phenylimidazolium-trimellitate, 2,4-diamino-6- [2'-di
  • aromatic amines are excluded as curing agents, more preferably, the hardener or the epoxy resin system used according to the invention is completely free of primary or secondary aliphatic or cycloaliphatic amines.
  • tertiary amines can be included as catalytically active amines. Imidazoles in general are not expected according to the invention to the amines.
  • the epoxy resin which is used according to the invention, the present invention is not particularly limited, it can be used all common epoxy resins, Preferred representatives are, for example, aliphatic, cycloaliphatic or aromatic epoxy resins. Likewise, bi-, tri- or polyfunctional epoxy resins can be used.
  • Particularly preferred representatives of aliphatic epoxy resins are selected from the group consisting of alkanediol glycidyl ether, in particular butanediol and / or hexanediol diglycidyl ether; 1, 2: 4,5-diepoxy-3,3-dimethylpentane (dimethylpentane dioxide), 2,2'-bioxirane (butadiene diepoxide); Di-, tri- or poly-ethylene glycol diglycidyl ether; Di-, tri- or poly-propylene glycol diglycidyl ethers and / or mixtures thereof.
  • epoxy resins are selected from the group consisting of 3-cyclohexenylmethyl-3-cyclo hexylcarboxylatdiepoxid, 3,4-epoxy cyclo hexane carboxylic acid (3,4-epoxycyclohexyl-methyl ester), 3,4-epoxy 6-methylcyclohexylmethyl-3 ', 4'-epoxy-6-methylcyclohexanecarboxylate, 4-vinyl-1-cyclohexene diepoxide (vinylcyclohexane dioxide), bis (3,4-epoxycyclohexylmethyl) adipate, dicyclopentadiene dioxide , 1,2-epoxy-6- (2,3-epoxypropoxy) hexa-hydro-4,7-methanoindane and / or mixtures thereof.
  • aromatic epoxy resins are in particular selected from the group consisting of bisphenol A epoxy resins, bisphenol F epoxy resins, phenol novolac epoxy resins, cresol novolac epoxy resins, Biphenylepoxidharzen, Biphenolepoxidharzen, 4,4'-biphenyl epoxy resins, Di-vinylbenzene dioxide, 2-glycidylphenyl glycidyl ether, tetraglycidylmethylenedi- aniline and / or mixtures thereof.
  • the epoxy resin system of the present invention may include other additives such as toughening modifiers.
  • the additives are in the case of their presence in a preferred amount of 20 to 99 wt .-% ; preferably from 45 to 95% by weight, preferably from 0.1 to 99% by weight, more preferably from 50 to 60% by weight, based on said epoxy resin system.
  • Particularly suitable toughening modifiers are selected from the group consisting of carboxyl-terminated butadiene-acrylonitrile liquid rubber, amine-terminated butadiene-acrylonitrile liquid rubber, maleic acid-treated polybutadiene or butadiene-styrene copolymer, hydroxyl-functional polybutadiene oligomers, epoxy-terminated urethane prepolymers, and epoxy-terminated polysulfides, epoxidized polybutadiene, core-shell particles (eg Genioperl ® from Wacker), thermoplastic silicone elastomers (eg Geniomer * from Wacker), elastomers, siloxanes, polyethers having functional groups, nanoparticles, and mixtures and / or combinations thereof.
  • core-shell particles eg Genioperl ® from Wacker
  • thermoplastic silicone elastomers eg Geniomer * from Wacker
  • elastomers siloxanes
  • polyethers
  • Hypro CBTN 1300 X8, 1300 X13 or 1300 X15 are Hypro CBTN 1300 X8, 1300 X13 or 1300 X15.
  • the epoxy resin system according to the present invention comprises at least one filler, wherein the at least one filler is preferably selected from the group consisting of calcium carbonate, silica, alumina, aluminum hydroxide, aluminum powder, talc, kaolin, barium sulfate, calcium sulfate Potymer powder, glass bubbles, carbon black, feldspar, mica, quartz and mixtures and / or combinations thereof.
  • the at least one filler is in the case of his
  • accelerators can be contained in epoxy resin systems according to the invention. These accelerators are different from the outset be ⁇ signed curing agents or accelerators for epoxy resins. These accelerators are in the case of its presence in a preferred amount of 0.2 to 10 parts by weight, preferably from 0.5 to 5 wt .-%, particularly preferably from 0.5 to 2 wt .-%, based on the mentioned epoxy resin system included.
  • the adhesive may contain reactive diluents or other raw materials typical in epoxy resin formulations, each in the case of their presence in a preferred amount of 0.1 to 30 wt .-%, preferably from 0.2 to 10 wt .-%, particularly preferably from 0 , 5 to 5 wt .-%, based on said epoxy resin system included.
  • the epoxy resin may be present in all major forms of preparation here, ie as a single component, in which all components use ⁇ ready present in a mixture together, Such a composition only needs to be applied to the application and can be ordered at elevated temperatures, for example at temperatures ranging between room temperature and 200 ° C, are cured.
  • the epoxy resin system as a two-component system, so that at least the epoxy resin and the hardener are present separately from one another. Immediately before application of the epoxy resin system, the individual components of the epoxy resin system are then mixed together.
  • a component coated with an epoxy resin system according to the invention is likewise provided, wherein the component is preferably selected from the group consisting of fastening elements, bolts, grab handles or reinforcing plates.
  • the aforementioned preferred components are merely exemplary in nature. In particular, in the event that epoxy resin and hardener are coordinated so that the
  • Epoxy resin system is fixed at temperature and tack-free, the pre-coated components can be independently prefabricated and sold. For an application, then only heating of the components or the epoxy resin system thereon is necessary to cure the epoxy resin system, e.g. by melting the epoxy resin system with subsequent chemical crosslinking.
  • the use of the epoxy resin system described above is further specified as a thermally curable adhesive.
  • the thermally curable adhesive can, depending on which epoxy resins or
  • Hardeners are used, be designed so that a cure between room temperature and 200 ° C, for example, with melting takes place.
  • the uses of the epoxy resin system are e.g. the bonding of components, in particular fasteners, bolts, handles or reinforcing plates.
  • the present invention relates to a method for indicating the progress and / or the end point of a Auspatirungsre force erfindungsge ⁇ MAESSEN epoxy resin, wherein the epoxy resin provided on the temperature required for curing is heated and a color change is determined, the color change indicating the progress and / or the end of the curing.
  • the epoxy resin system can of course be applied to components to be bonded together.
  • the color reaction serves to determine whether the adhesive is still fresh or already reacted (control of storage stability or pot life)
  • the present invention relates to the use of a dye which reacts with the epoxy resin with color change upon curing of an epoxy resin system, as an indicator of the course and / or the end point of the curing of the epoxy resin.
  • An adhesive (see Table 1) was prepared containing a dye (Sudan IV) with a reactive OH group.
  • the freshly prepared adhesive had a red color.
  • the color changed from red to purple to blue.
  • the change in hue is related to the degree of cure of the adhesive. If the adhesive has not cured yet, it shows a red color. If the adhesive has already partially hardened (significantly higher viscosity), the color changes to purple.
  • the fully cured adhesive shows a blue ⁇ black color.
  • the color change could also be detected in addition to the use of imidazoles as a curing agent and in the use of imidazole adducts as a hardener.
  • the discoloration occurred in all experiments, but to varying degrees.

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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)
  • Epoxy Resins (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne un système résine époxy contenant un colorant qui, lors de la prise du système résine époxy, indique par changement de couleur l'évolution ou le point final de la prise de la résine époxy. L'invention concerne également des composants recouverts d'un système résine époxy selon l'invention et décrit l'utilisation du système résine époxy comme colle thermodurcissable. De plus, la présente invention définit un procédé pour indiquer l'évolution ou le point final de la réaction de prise d'un système résine époxy. En outre, la présente invention décrit l'utilisation d'un colorant qui réagit avec un système résine époxy en changeant de couleur, servant ainsi d'indicateur de l'évolution ou du point final de la prise d'un système résine époxy.
PCT/EP2012/054255 2011-03-11 2012-03-12 Système résine époxy permettant un contrôle visuel de l'état de prise Ceased WO2012123403A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011013645.2 2011-03-11
DE102011013645A DE102011013645A1 (de) 2011-03-11 2011-03-11 Epoxidharzsystem mit visueller Kontrolle des Aushärtezustandes

Publications (1)

Publication Number Publication Date
WO2012123403A1 true WO2012123403A1 (fr) 2012-09-20

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DE (1) DE102011013645A1 (fr)
WO (1) WO2012123403A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105038671A (zh) * 2015-06-12 2015-11-11 东莞翔思电子科技有限公司 一种led铝基板结合剂及使用该结合剂的led铝基板
WO2018008742A1 (fr) * 2016-07-08 2018-01-11 セメダイン株式会社 Composition adhésive de structure dont la couleur change lorsqu'elle est durcie à la chaleur
CN113166604A (zh) * 2018-12-11 2021-07-23 罗曼有限合资公司 可缠绕和冲压的粘合膜
US20220380642A1 (en) * 2019-07-05 2022-12-01 Lohmann Gmbh & Co. Kg Compressible UV-activatable or thermally activatable (semi-) structural adhesive film that changes color after activation and after curing
CN118930814A (zh) * 2024-09-13 2024-11-12 南方电网科学研究院有限责任公司 一种环氧树脂固化指示化合物及制备方法和组合物
US12305083B1 (en) 2022-06-16 2025-05-20 3M Innovative Properties Company Two-part epoxy adhesive with working life color change indicator

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102016223662A1 (de) * 2016-11-29 2018-05-30 Siemens Aktiengesellschaft Vergussmasse, Isolationswerkstoff und Verwendung dazu
TWI876058B (zh) * 2020-06-15 2025-03-11 日商富士軟片股份有限公司 著色組成物、膜、濾色器、固體攝像元件及圖像顯示裝置
CN117362935A (zh) * 2023-10-30 2024-01-09 广东龙宇新材料有限公司 一种添加氮丙啶交联剂的萘酚酚醛环氧组合物及其应用

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB960276A (en) * 1960-03-17 1964-06-10 Shell Int Research Process for mixing curing agents with epoxy resins
US4069191A (en) * 1974-05-30 1978-01-17 Post John F Metal patching composition and method
US5425824A (en) * 1988-05-17 1995-06-20 Alcan International Ltd. Color-changeable adhesive
WO1999038902A1 (fr) * 1998-01-29 1999-08-05 Alpha Metals, Inc. Indicateur colore d'achevement de la polymerisation de matieres thermodurcissables
US20060029810A1 (en) * 2004-08-03 2006-02-09 General Electric Company One part, heat cured pressure sensitive adhesives
EP2210927A1 (fr) * 2007-11-08 2010-07-28 Wuhan Keda Marble Protective Materials CO., LTD. Adhésif sec rouge et vert et son procédé de fabrication
EP2223966A1 (fr) 2009-02-25 2010-09-01 3M Innovative Properties Company Compositions d'époxy adhésives dotées d'une grande résistance mécanique sur une large plage de températures

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4001417A1 (de) * 1990-01-19 1991-07-25 Beiersdorf Ag Zaehelastifizierter, zweikomponentiger epoxidharzklebstoff
WO2005030853A1 (fr) * 2003-09-30 2005-04-07 Nuplex Industries Limited Compositions epoxy et procedes de detection de durcissement
DE102007043559B4 (de) * 2007-09-13 2012-05-31 Carl Zeiss Vision Gmbh Verwendung eines lichthärtenden thermoplastischen Epoxidharzklebstoffs zum Blocken oder Kleben von optischen Bauelementen

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB960276A (en) * 1960-03-17 1964-06-10 Shell Int Research Process for mixing curing agents with epoxy resins
US4069191A (en) * 1974-05-30 1978-01-17 Post John F Metal patching composition and method
US5425824A (en) * 1988-05-17 1995-06-20 Alcan International Ltd. Color-changeable adhesive
WO1999038902A1 (fr) * 1998-01-29 1999-08-05 Alpha Metals, Inc. Indicateur colore d'achevement de la polymerisation de matieres thermodurcissables
US6017983A (en) 1998-01-29 2000-01-25 Alpha Metals, Inc. Color indicator for completion of polymerization for thermosets
US20060029810A1 (en) * 2004-08-03 2006-02-09 General Electric Company One part, heat cured pressure sensitive adhesives
EP2210927A1 (fr) * 2007-11-08 2010-07-28 Wuhan Keda Marble Protective Materials CO., LTD. Adhésif sec rouge et vert et son procédé de fabrication
EP2223966A1 (fr) 2009-02-25 2010-09-01 3M Innovative Properties Company Compositions d'époxy adhésives dotées d'une grande résistance mécanique sur une large plage de températures

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105038671A (zh) * 2015-06-12 2015-11-11 东莞翔思电子科技有限公司 一种led铝基板结合剂及使用该结合剂的led铝基板
WO2018008742A1 (fr) * 2016-07-08 2018-01-11 セメダイン株式会社 Composition adhésive de structure dont la couleur change lorsqu'elle est durcie à la chaleur
JPWO2018008742A1 (ja) * 2016-07-08 2019-05-23 セメダイン株式会社 加熱硬化により色が変化する構造用接着剤組成物
CN113166604A (zh) * 2018-12-11 2021-07-23 罗曼有限合资公司 可缠绕和冲压的粘合膜
US20220380642A1 (en) * 2019-07-05 2022-12-01 Lohmann Gmbh & Co. Kg Compressible UV-activatable or thermally activatable (semi-) structural adhesive film that changes color after activation and after curing
US12305083B1 (en) 2022-06-16 2025-05-20 3M Innovative Properties Company Two-part epoxy adhesive with working life color change indicator
CN118930814A (zh) * 2024-09-13 2024-11-12 南方电网科学研究院有限责任公司 一种环氧树脂固化指示化合物及制备方法和组合物
CN118930814B (zh) * 2024-09-13 2025-10-28 南方电网科学研究院有限责任公司 一种环氧树脂固化指示化合物及制备方法和组合物

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