WO2017109620A1 - Composant de résine époxy pour composition adhésive - Google Patents

Composant de résine époxy pour composition adhésive Download PDF

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Publication number
WO2017109620A1
WO2017109620A1 PCT/IB2016/057420 IB2016057420W WO2017109620A1 WO 2017109620 A1 WO2017109620 A1 WO 2017109620A1 IB 2016057420 W IB2016057420 W IB 2016057420W WO 2017109620 A1 WO2017109620 A1 WO 2017109620A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxy resin
resin component
range
adhesive composition
wollastonite
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/IB2016/057420
Other languages
English (en)
Inventor
Abhijit Som
Amit Dixit
Chularat Iamsamai
Kitibodee SUPATTARASAKDA
Pradip Kumar Dubey
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.)
Aditya Birla Chemicals Thailand Ltd
Original Assignee
Aditya Birla Chemicals Thailand Ltd
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 Aditya Birla Chemicals Thailand Ltd filed Critical Aditya Birla Chemicals Thailand Ltd
Publication of WO2017109620A1 publication Critical patent/WO2017109620A1/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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/22—Expanded, porous or hollow particles
    • C08K7/24—Expanded, porous or hollow particles inorganic
    • C08K7/26—Silicon- containing compounds
    • 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 disclosure relates to epoxy resin components for adhesive composi- tions. Specifically, the present disclosure relates to low density epoxy resin components having desired rheological properties and suitable for use in structural adhesives.
  • Structural adhesives find application in various industries such as automobile, wind mill, aerospace to produce a load-bearing joint.
  • Structural adhesives or in general any adhesive composition comprises of any of the following elements: adhesive base, diluents, hardener/curatives, fillers, solvents and carriers.
  • Adhesive base is the key ingredient of the adhesive composition which forms bonds between itself in the presence of a suitable hardener or curative.
  • Fillers are added to modify or enhance the properties of the adhesive base such as: to improve the rheological properties such as viscosity, sag resistance and reduction in shrinkage upon curing. Fillers may also be added to increase the cured strength, impart or enhance electrical or thermal conductivity, increase the bulk etc.
  • An epoxy resin component for an adhesive composition comprises of an epoxy resin premix; and a filler composition comprising cenospheres and wollastonite in a w/w (weight / weight) ratio in a range of 1:0.01 - 1:5.
  • An adhesive composition comprising said epoxy resin component and a hardener component is also disclosed.
  • the present disclosure relates to an epoxy resin component for an adhesive composition.
  • an epoxy resin component for an adhesive composition.
  • the present disclosure relates to a low density epoxy resin component suitable for use in structural adhesives.
  • Said epoxy resin component comprises of an epoxy resin premix; and a filler composition comprising cenospheres and wollastonite in a w/w ratio in a range of 1:0.01 - 1:5.
  • the adhesive composition comprises about 65-75 % w/w of an epoxy resin component, and about 25-35% w/w of a hardener component.
  • the epoxy resin component comprises of an epoxy resin premix and a filler composition comprising cenospheres and wollastonite in a w/w ratio in a range of 1:0.01- 1:5.
  • the epoxy resin component disclosed herein has a lower density but similar or improved rheological properties as compared to conventional epoxy resin components.
  • Conventional epoxy resin component in context of the present disclosure refers to an epoxy resin component having the same ingredients as that used in the epoxy resin component of the present disclosure, except the filler composition.
  • the conventional epoxy resin component includes conventional fillers such as milled glass fibres.
  • conventional adhesive composition refers to an adhesive composition comprising a conventional epoxy resin component.
  • cenospheres and wollastonite in the given ratio provides a syn- ergistic effect of maintaining the rheological properties such as viscosity, thixotropic index in the desired range while reducing the density of the epoxy resin component and hence the cured adhesive composition.
  • the present inventors observed that when cenospheres and wollastonite are used individually, the rheological properties such as viscosity and thixotropic index of the epoxy resin component increase beyond the desired range making the epoxy resin component unsuitable for use as a structural adhesive.
  • an epoxy resin component having a viscosity in a range of 300-700 Pa.S at 25°C, a thixotropic index in a range of 3-5 can be obtained, while achieving a reduction in weight / density by 5-15 % .
  • the density of the resultant adhesive composition is 8-10% lower than that of the conventional adhe- sive composition.
  • Low density adhesive compositions aid in reducing the overall weight of the structure to which it is applied such as a windmill blade, thereby increasing its efficiency. Additionally, it may also lead to an improvement in other properties of the adhesive composition, such as sagging, peel strength and shrinkage.
  • Cenospheres used in the filler composition are lightweight, inert, hollow spheres made of one or more of Si0 2 ,Al 2 0 3 ,CaO, K 2 0, Fe 2 0 3 , Ti0 2 , MgO, NA 2 0 and filled with an inert air or gas such as carbon dioxide and nitrogen.
  • Said cenospheres have a particle size in a range of 75- 300 ⁇ .
  • cenospheres have the particle size in the range of 100-150 ⁇ .
  • said cenospheres have a bulk density in a range of 300-600 Kg/m 3 .
  • said cenospheres have the bulk density in the range of 400-500 Kg/m 3 .
  • Said cenospheres may be manufactured by any known method or may be obtained from commercial sources. For example, cenospheres sold by Cenosphere India Pvt. Ltd. under the trade name CILTM 500 may be used.
  • Wollastonite used in the filler composition is a naturally occurring calcium silicate having formula Ca 3 Si 3 09 and a needle-like shape.
  • Said wollastonite has a particle size in a range of 75-300 ⁇ .
  • the particle size is in the range of 100-200 ⁇ .
  • said wollastonite has an aspect ratio in a range of 5: 1 to 30: 1.
  • wollastonite has an aspect ratio in the range of 10: 1-20: 1.
  • said wollastonite has a bulk density in a range of 200-500 Kg/m 3 .
  • said wollastonite has the bulk density in a range of 300-400 Kg/m 3 .
  • Wollaston- ite may be manufactured by any known method or obtained from commercial sources.
  • wollastonite sold by Wolkem India Ltd. under the trade name "KEMOLIT 3 ⁇ 4 " may be used.
  • wollastonite is in surface modified form. The surface modification may be achieved with known silanes by any known method.
  • Commercially available surface modified wollastonite may also be used.
  • surface modified wollastonite sold by Wolkem India Ltd. under the trade name "FIL- LEX ® " may be used.
  • the filler composition comprises cenospheres and wollastonite in a w/w ratio in a range of 1:0.01-1:5. In accordance with a preferred embodiment, the filler composition comprises cenospheres and wollastonite in a w/w ratio in a range of 1: 1 to 1:3.
  • the filler composition is present in the epoxy resin component in an amount in a range of 10-30 % w/w of said epoxy resin component. In accordance with a preferred embodiment, the filler composition is present in the epoxy resin component in an amount in a range of 15-25 % w/w of said epoxy resin component.
  • the epoxy resin premix comprises of at least one epoxy resin, at least one diluent and fumed silica.
  • the epoxy resin may be a polyglycidyl ether of a polyhydric alcohol such as 1,4-butanediol or 1,3 -propanediol or, preferably, a polyglycidyl ether of a polyhydric phenol, for example a bisphenol such as bis(4- hydroxyphenyl)methane (bisphenol F) or 2,2-bis-(4-hydroxyphenyl)propane (bisphenol A) or a novolak formed from formaldehyde and a phenol such as phenol itself or a cresol, or a mixture of two or more such polyglycidyl ethers.
  • a bisphenol such as bis(4- hydroxyphenyl)methane (bisphenol F) or 2,2-bis-(4-hydroxyphenyl)propane (bisphenol A)
  • bisphenol bis(4- hydroxyphenyl)methane
  • bisphenol A 2,2-bis-(4-hydroxyphenyl)propane
  • said epoxy resin is selected from a group consisting of bisphenol A diglycidyl ether and bisphenol F diglycidyl ether.
  • a combination of two or more epoxy resins may also be used.
  • Such epoxy resins may be prepared using known methods or may be obtained from commercial sources.
  • the epoxy resin forms at least 60-80%, and preferably 65-75% of the epoxy resin component.
  • the diluent is a reactive diluent which participates in a chemical reaction with at least one other ingredient of the adhesive composition upon curing.
  • the reactive diluent may be selected from a group consisting of epoxy families like di ols, mono ols, novolacs and epoxy urethane hybrids.
  • the diluent is a non-reactive diluent.
  • the non-reactive diluent may be selected from a group consisting of Benzyl alcohol, Furfurylalcohol, Nonyl phenol, Dibutyl phthalate and hydrocarbon resins such as Necirez -products, Epodil-L, Pine-oil.
  • the diluents which could modify certain properties of the epoxy resin component or the adhesive composition may also be used. Also, a combination of two or more diluents may be used.
  • the diluent is added in an amount in a range of 0-20% w/ w of said epoxy resin component. The amount of diluent may vary in accordance with the application.
  • aforesaid fumed silica may be hydrophilic or hydrophobic. Fumed silica is added in an amount in a range of 0.01-10% w/ w of said epoxy resin component. Fumed silica assists in improving thixotropy and anti- setting properties. Fumed silica used in the present disclosure may be selected from fumed silica known in the art; or may be obtained from commercial sources. In accordance with an embodiment, a color may be additionally included in the epoxy resin premix.
  • Said epoxy resin premix may be prepared by any known method.
  • the epoxy resin premix is prepared by mixing the epoxy resin and the reactive diluents in a reactor, followed by the addition of fumed silica.
  • the epoxy resin premix may be obtained from commercial sources.
  • an intermediate of Epotec® YD1535 G a commercially available epoxy resin component from Aditya Birla Chemi- cals, Thailand may be used.
  • the intermediate comprises of bisphenol A based diglycidyl ether, bisphenol F based diglycidyl ether and reactive diluents and is referred to as Epotec® YD1535G premix.
  • the hardener component comprises of at least one hardener and fumed silica. Any known hardener may be used. Any two or more hardeners may also be used depending on the application.
  • the hardener may be selected from a group consisting of polyetheramine, cycloaliphatic amines having an amino or aminoalkyl group attached to the ring, such as 3-aminomethyl- 3,5,5-trimethylcyclohexylamine (isophoronediamine), an amino polyamide, tetraethylene- pentamine having N-(2-aminoethyl)-N'- ⁇ 2- ⁇ (2-aminoethyl)amino ⁇ ethyl ⁇ -l,2- ethanediamine, 2, 4-(2-aminoethyl)-N-(2-aminoethyl)-N'- ⁇ 2- ⁇ (2- aminoethyl) amino ⁇ ethyl ⁇ - 1 ,2-ethanediamine,2,2,
  • the hardener is a mixture of polyetheramine, isophoronediamine(IPDA) and aminopoly amide.
  • IPDA isophoronediamine
  • the hardener is a mixture of IPDA, polyetheramine , polyamide and an aliphatic amine.
  • the hardeners suitable for the presently disclosed hardener component may be prepared by any known method or obtained from commercial sources.
  • fumed silica used in the hardener component may be hydrophilic or hydrophobic. Fumed silica is added in an amount in the range of 0.1 -10 % w/ w of said hardener component. Said fumed silica may be selected from fumed silica known in the art; or may be obtained from commercial sources.
  • the hardener component may further comprise of conventional filler such as milled glass fibres.
  • a color may be additionally included in the hardener component.
  • the hardener component may be prepared by any known method.
  • the hardener component is prepared by mixing one or more harden- ers followed by addition of fumed silica.
  • the hardener component may be obtained from commercial sources.
  • Epotec® TH7257G commercially available from Aditya Birla Chemicals, Thailand
  • an intermediate of Epotec® TH7257G (or Epotec® TH7257G without the fillers) may be used as the hardener component. This intermediate is referred to as Epotec® TH7257G premix.
  • the hardener component may be mixed with the epoxy resin component in a quantity depending on formulation stoichiometry.
  • the hardener component is added in an amount in a range of 25-35 % w/w of the total weight of the adhesive composition.
  • the epoxy resin component and the hardener component are added in a w/w ratio in a range of 100: 40 to 100:50.
  • the epoxy resin component and the hardener component are mixed in a w/w ratio of 100:45.
  • the adhesive composition may further comprise optional additives.
  • Optional additives may include but are not limited to other resins, stabilizers, plasticizers, catalyst de-activators, dyes, pigments, thixotropic agents, photo initiators, latent catalysts, inhibitors, surfactants, solvents, fluidity control agents, diluents that aid processing, adhesion promoters, flexibilizers, toughening agents, fire retardants, and mixtures thereof.
  • any known method may be used to mix the epoxy resin component, the hardener component and any optional additive.
  • the mixing is carried out in planetary mixer/ stirrer.
  • the adhesive composition of the present disclosure can be applied to a surface of metal, plastic, fiberglass, or another material that the adhesive composition can bond to.
  • the adhesive composition may be applied to one or between one or more surfaces and then cured. Any known method of applying the adhesive composition may be used. These include, for example, static mixer, rolling coating, and the like.
  • the curing of the adhesive composition may be carried out by heating. For heat curing, the adhesive composition is subjected to heating at a predetermined temperature for a predetermined period of time. The temperature and time required for curing would depend on the epoxy resins and the hardeners used in the adhesive composition.
  • Such an epoxy resin component for an adhesive composition comprising an epoxy resin premix; and a filler composition comprising ceno- spheres and wollastonite in a w/w ratio in a range of 1:0.01-1:5.
  • Such an epoxy resin component wherein the filler composition comprises ceno- spheres and wollastonite in a w/w ratio in a range of 1: 1 to 1:3.
  • Such an epoxy resin component wherein the filler composition is present in an amount in a range of 10-30 % w/w of said epoxy resin component.
  • Such an epoxy resin component wherein the filler composition is present in an amount in a range of 15-25 % w/w of said epoxy resin component.
  • Such an epoxy resin component wherein cenospheres have a particle size in a range of 100-150 ⁇ .
  • Such an epoxy resin component wherein wollastonite has an aspect ratio in a range of 10: 1- 20: 1.
  • Such an epoxy resin component wherein wollastonite is in surface modified form.
  • Such an epoxy resin component having a viscosity in a range of about 300-700 Pa.S at 25°C.
  • Such an epoxy resin component having a thixotropic index in a range of about 3-5.
  • Such an adhesive composition comprising about 65-75 % w/w of said epoxy resin component; and about 25-35 % w/w of a hardener component.
  • Example 1 Preparation of the adhesive composition in accordance with the present disclosure.
  • the epoxy resin component was prepared using 71.1 parts by weight of epoxy resin premix (Epotec® YD1535G premix) to which 8.2 parts by weight of cenosphere (CIL150), 15.4 parts by weight of wollastonite (KEMOLIT ® KSV-51) and 5.3 parts by weight of fumed silica were added and mixed in a blender at room temperature.
  • the epoxy resin component and the hardener component were mixed at 25°C in a ratio of 100:43.2 (w/w) to obtain the adhesive composition.
  • the adhesive composition was shaped to be a desired specimen, and was cured in the oven at specific conditions to determine the properties thereof. Weight reduction, sagging, viscosity were measured using conventional methods. Peel strength was measured by Standard IS011339. Tensile lap shear and fracture toughness were determined by Standard DINEN1465 and IS013586 respectively.
  • Example 2 Preparation of the adhesive composition in accordance with present disclosure (Hardener contains milled glass fibres (MGF)).
  • the epoxy resin component was prepared using 71.1 parts by weight of epoxy resin premix (Epotec® YD1535G premix) to which 8.2 parts by weight of cenosphere (CIL150), 15.4 parts by weight of wollastonite (KEMOLIT ® KSV-51) and 5.3 parts by weight of fumed silica were added and mixed in a blender at room temperature.
  • the hardener component was prepared by mixing Epotec® TH7257G and milled glass fibers. The epoxy resin component and the hardener component were mixed at 25 °C in a ratio of 100:45 (w/w) to obtain the adhesive composition.
  • the adhesive composition was shaped to be a desired specimen, and was cured in the oven at specific condition for each testing methods (specified in Example 1).
  • Comparative Example 1 The properties of the epoxy resin component and the adhesive composition prepared in Examples 1 and 2 were compared with that of a conventional adhesive composition (S I).
  • the composition of conventional adhesive composition (S I) is provided in Table 3.
  • the method illustrated in Example 1 was used to prepare the conventional adhesive composition.
  • Fracture toughness 60°Cxl.5h + 70°Cx7h
  • Comparative Example 2 Various samples of adhesive compositions comprising solely cenospheres (CI, C2)/ wollastonite (Wl, W2) were also prepared. The properties of these adhesive compositions were compared with that of the conventional adhesive composition (S I). The composition and the properties of said samples vis-a-vis the conventional adhesive composition have been tabulated in Table 5. Table 5
  • the adhesive composition comprising the filler composition of the present disclosure may be used to bond relatively large structures including but not limited to, aerodynamic wings, wind turbine blades, and automobile components.
  • the filler composition formed by cenospheres and wollastonite employed is cheap and easy to manufacture.
  • An unexpected synergy between cenospheres and wollastonite, employed in accordance with the present disclosure contributes to or provides a number of improvements in the adhesive composition, such as: viscosity and thixotropic index are in desirable range, the overall weight reduces, shrinkage and peel strength improves.
  • Weight reduction, particularly in windmill application plays an important role in reducing the weight of the blade and thereby improving the efficiency of windmill. Similar effect can be observed when the adhesive composition of the present disclosure is applied to other applications.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne un composant de résine époxy pour une composition adhésive. Ledit composant de résine époxy comprend un prémélange de résine époxy ; et une composition de charge comprenant des cénosphères et de la wollastonite selon un rapport p/p (poids/poids) dans une plage allant de 1:0,01 à 1:5.
PCT/IB2016/057420 2015-12-22 2016-12-08 Composant de résine époxy pour composition adhésive Ceased WO2017109620A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN4221DE2015 2015-12-22
IN4221/DEL/2015 2015-12-22

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WO2017109620A1 true WO2017109620A1 (fr) 2017-06-29

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210388179A1 (en) * 2018-11-27 2021-12-16 Nisshinbo Holdings Inc. Resin composition for acoustic matching layer
CN119039916A (zh) * 2024-09-24 2024-11-29 广东晨宝复合材料股份有限公司 一种耐黄变石英石胶水树脂及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0488949A2 (fr) * 1990-11-29 1992-06-03 Ciba-Geigy Ag Adhésif à haute performance à base de résine époxyde
EP0736556A2 (fr) * 1995-04-04 1996-10-09 Ciba-Geigy Ag Composition de résin époxy durcissable contenant de la wollastonite
WO2003078163A1 (fr) * 2002-03-15 2003-09-25 Henkel Kommanditgesellchaft Auf Aktien Adhesif epoxyde dote d'une meilleure resistance aux chocs
US20080251202A1 (en) * 2007-04-11 2008-10-16 Eagle Glenn G Heat-resistant structural epoxy resins
WO2009094295A1 (fr) * 2008-01-22 2009-07-30 Dow Global Technologies Inc. Adhésifs structuraux en résine époxy contenant des agents de durcissement élastomères allongés par polyphénol à fonctionnalité époxyde

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0488949A2 (fr) * 1990-11-29 1992-06-03 Ciba-Geigy Ag Adhésif à haute performance à base de résine époxyde
EP0736556A2 (fr) * 1995-04-04 1996-10-09 Ciba-Geigy Ag Composition de résin époxy durcissable contenant de la wollastonite
WO2003078163A1 (fr) * 2002-03-15 2003-09-25 Henkel Kommanditgesellchaft Auf Aktien Adhesif epoxyde dote d'une meilleure resistance aux chocs
US20080251202A1 (en) * 2007-04-11 2008-10-16 Eagle Glenn G Heat-resistant structural epoxy resins
WO2009094295A1 (fr) * 2008-01-22 2009-07-30 Dow Global Technologies Inc. Adhésifs structuraux en résine époxy contenant des agents de durcissement élastomères allongés par polyphénol à fonctionnalité époxyde

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20210388179A1 (en) * 2018-11-27 2021-12-16 Nisshinbo Holdings Inc. Resin composition for acoustic matching layer
US12012501B2 (en) * 2018-11-27 2024-06-18 Nisshinbo Holdings Inc. Resin composition for acoustic matching layer
CN119039916A (zh) * 2024-09-24 2024-11-29 广东晨宝复合材料股份有限公司 一种耐黄变石英石胶水树脂及其制备方法

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