WO1995020612A1 - Epoxy resin hardener, epoxy resin composition, and epoxy resin hardening process - Google Patents
Epoxy resin hardener, epoxy resin composition, and epoxy resin hardening process Download PDFInfo
- Publication number
- WO1995020612A1 WO1995020612A1 PCT/EP1995/000305 EP9500305W WO9520612A1 WO 1995020612 A1 WO1995020612 A1 WO 1995020612A1 EP 9500305 W EP9500305 W EP 9500305W WO 9520612 A1 WO9520612 A1 WO 9520612A1
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- WO
- WIPO (PCT)
- Prior art keywords
- epoxy resin
- substituted
- groups
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- unsubstituted
- Prior art date
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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
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08L61/14—Modified phenol-aldehyde condensates
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4223—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aromatic
-
- 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
Definitions
- the present invention relates to an epoxy resin hardener, an epoxy resin composition and an epoxy resin hardening process, which are all designed to give a cured product having outstanding moisture resistance.
- Epoxy resins are used in a broad range of applications, such as adhesion, casting, potting, lamination, moulding and coating, in view of their good handling properties and curing characteristics.
- hardeners are known, which hardeners are used in combination with the epoxy resins to give cured products .
- the properties of the cured products may vary very much, depending on the hardener used. Therefore appropriate hardeners are selected for specific fields or purposes.
- an acid anhydride hardener results in a lower amount of hydroxyl groups but there is an adverse effect on moisture resistance, because after the reaction with an epoxy resin an ester linkage is formed which is poor in moisture resistance.
- a hardener of polymerization catalyst does not form hydroxyl groups but it aggravates moisture resistance because of its mgn reactivity.
- the inventors carried out a series of experiments on hardeners which do not have an adverse effect on the moisture resistance of the cured products and which give rise to as few groups as possible which aggravate the moisture resistance of the cured products.
- the object is achieved by using as the hardener an aromatic ester having a carboxylic ester linkage in the molecule which connects the aromatic rings directly to each other.
- the carboxylic ester linkage reacts with epoxy groups to cure the epoxy resin without giving rise to hydroxyl groups and the like which aggravate the moisture resistance of cured products.
- the present invention is embodied in an epoxy resin hardener having in the molecule on average two or more functional groups which may react with epoxy groups, in which on average one or more functional groups are aromatic ester groups derived from aromatic carboxylic acids and hydroxy-aromatic compounds, the ester groups directly connecting the aromatic rings of the acid and the hydroxy compound to each other.
- the present invention is also embodied in an epoxy resin composition and an epoxy resin hardening process, the former containing and the latter using the epoxy resin hardener defined above.
- the epoxy resin hardener is an aromatic ester which has a carboxylic ester linkage which connects the aromatic rings directly to each other (here below referred to briefly as "a direct ester linkage between aromatic rings”) . It s this linkage that is involved in the curing reaction mechanism of epoxy resins. The reaction is explained by the following formula (2) with reference to an instance in which the direct ester linkage between aromatic rings is the phenyl benzoate linkage.
- the hardener (whose main skeleton is connected to the aromatic ring adjacent to the oxygen atom) yields a cured product in which the hardener is connected to the epoxy resin through the carbon-carbon linkage and ether linkage, which do not impair moisture resistance. Moreover, the hardener does not result in the formation of hydroxyl groups which lower the moisture resistance, unlike the conventional phenol- based or amine-based hardener. It follows, therefore, that the hardener yields a cured product having outstanding moisture resistance.
- the direct ester linkage between aromatic rings in the present invention cannot be replaced by any other ester in which one side or both sides of the ester linkage are not aromatic rings, that is, an aromatic ring and an aliphatic chain are connected directly to each other by an ester linkage, or aliphatic chains are connected directly to each other by an ester linkage.
- Such an ester when used as an epoxy resin hardener, does not react with the epoxy group at all, or its reaction rate is too slow to be of practical use even though it undergoes reaction.
- the present invention specifies as the epoxy resin hardener an aromatic ester having on average one or more direct ester linkages between aromatic rings in the molecule and also having on average two or more functional groups, which react with epoxy groups, including said direct ester linkage between aromatic rings.
- This aromatic ester should preferably be one which does not have other functional groups, which react with epoxy groups, than the direct ester linkage between aromatic rings, so that the cured product has the desired moisture resistance. If the aromatic ester does contain other functional groups, their number should be limited such that the number of the ester linkages accounts for more than 50%, preferably more than 70%, of the total number of functional groups.
- the epoxy resin hardener may be substituted by groups or atoms on its aromatic rings.
- the aromatic ester has substituted groups such as phenolic hydroxy groups, primary or secondary ammo groups, carboxylic groups, acid anhydride groups and mercapto groups, such groups will work as functional groups to react with epoxy groups.
- the number of such functional groups is preferably less than 50% of the total number of functional groups; otherwise, they have an adverse effect on the moisture resistance of the cured product.
- the epoxy resin hardener includes various kinds of compounds prepared by various methods.
- Typical aromatic esters are obtainable by, and are suitably prepared by esterifying more than 50r of phenolic hydroxyl groups of a polyhydric phenol with benzoic acid or naphthoic ac d, said polyhydric phenol optionally being substituted by groups and/or atoms on the aromatic ring, said benzoic acid optionally being substituted by groups and/or atoms on the benzene ring, and said naphthoic acid optionally being substituted by groups and/or atoms on the naphthalene ring.
- polyhydric phenol having optionally substituted groups and/or atoms on the aromatic ring examples include bisphenol A, bisphenol F, resorcm, hydroquinone, dihydroxynaphthalene, biphenol, tetramethylbiphenol, tetrabromobisphenol A, phenol novolak resin, cresol novolak resin, bisphenol A novolak resin, dicyclopentadiene phenolic resin, terpene phenolic resin, phenol aralkyl resin, naphthalene novolak resin, brominated phenolnovolak resin, and polyhydric phenolic resin (which is a product of condensation reaction of a phenolic compound and an aldehyde such as hydroxybenzaldehyde, crotonaldehyde, and glyoxal) . Esterification of the polyhydric phenol (to produce a benzoate or naphthoate) may be accomplished in several ways. Typically, it employs an esterifying agent
- A represents a benzene ring or naphthalene ring
- R ⁇ represents a hydroxyl group, alkoxyl group, substituted or unsubstituted phenoxy group, substituted or unsubstituted naphthoxy group, substituted or unsubstituted benzoate group, substituted or unsubstituted naphthoate group, or halogen atom
- R 2 represents a c l-10 al yl group, especially a C ⁇ .. ⁇ alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted aralkyl group, an alkoxyl group or a halogen atom, especially a clorine or bromine atom, with two or more of R 2 being the same or different
- m is 0 or an integer of 1 to 5.
- the epoxy resin hardener of the present invention is obtainable by, and may suitably be prepared by esterifying more than 50% of the
- the esterification may be carried out in different ways under varied conditions depending on the kind and combination of the polyhydric phenol and esterifying agent used. Typically, it is carried out by mixing the two components in the presence or absence of an organic solvent in the presence of a catalyst at 0 to 150 °C for 1 to 10 hours. The reaction product is freed of the unreacted esterifying agent, solvent, and by-products. Thus there is obtained the desired aromatic ester.
- the catalyst examples include amines such as trimethylamine, triethyla ine, benzyldimethyla ine, and pyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; metal alcoholates such as potassium t-butoxide and sodium ethoxide; alkali metal compounds such as butyl lithium and biphenyl sodium; and acidic catalysts such as hydrochloric aci ⁇ , sulfu ⁇ c acid, oxalic acid, fluoroacetic acid, toluenesulfonic acid, acidic organic acid salts, fluoroboric acid, heteropolyacids, polyphosphoric acid, and activated clay.
- amines such as trimethylamine, triethyla ine, benzyldimethyla ine, and pyridine
- alkali metal hydroxides such as sodium hydroxide and potassium hydroxide
- metal alcoholates such as potassium t-butoxide and sodium ethoxide
- the solvent examples include ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; aromatic hydrocarbons such as benzene, toluene, and xylene; ethers such as dioxane and ethylene glycol dimethyl ether; and aprotic polar solvents such as dimethylsulfoxide and dimethylformamide, which are all inert organic solvents.
- ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone
- aromatic hydrocarbons such as benzene, toluene, and xylene
- ethers such as dioxane and ethylene glycol dimethyl ether
- aprotic polar solvents such as dimethylsulfoxide and dimethylformamide, which are all inert organic solvents.
- aromatic ester which is the epoxy resin hardener of the present invention, is a compound or a mixture of compounds .
- the above-mentioned reaction should preferably be carried out such a manner that the rate of esterification (or the rate of benzoate or naphthoate) is higher than 50%, preferably higher than 70%. If the rate of esterification is lower than specified above, large amounts of phenolic hydroxyl groups remain unreacted. They react with epoxy groups to contribute to the hardening of epoxy resins but, upon reaction with epoxy groups, they form hydroxyl groups which have an adverse effect on the moisture resistance of the cured product.
- the above-mentioned epoxy resin hardener may be incorporated, as an essential component, into an epoxy resin to give the epoxy resm composition of the present invention.
- an epoxy resin there are no restrictions on the epoxy resin.
- the epoxy resin include those which are produced from a phenolic compound and an epihalohydrin, those which are produced from an amine and an epihalohydrin, and those which are produced from a carboxylic acid and an epihalohydrin.
- the phenolic compound includes bisphenol A, bisphenol F, bisphenol AD, hydroquinone, resorcm, methylresorcm, biphenol, tetramethyl- biphenol, dihydroxynaphthalene, phenol novolak resm, cresol novolak resm, bisphenol A novolak resm, dicyclopentadiene phenolic resin, terpene phenolic resm, phenol aralkyl resm, and naphthol novolak resm.
- the phenolic compound further includes polyhydric phenolic resins which are formed by the condensation reaction of a phenolic compound and an aldehyde such as hydroxybenzaldehyde, croton- aldehyde, and glyoxal.
- the amme includes diammophenyl-methane, aminophenol, and xylenediamme.
- the carboxylic acid includes meth- ylhexahydroxyphthal c acid and di er acid.
- the epoxy resm composition of the present invention may be incorporated with an optional epoxy resin hardener in addition to the epoxy resm hardener of the present invention.
- the optional hardener examples include phenolic resins, polyhydric phenol resins, acid anhydrides, and amines.
- Phenolic resins include phenol novolak resin, cresol novolak resm, bisphenol A novolak resin, dicyclopentadienephenolic resm, phenolaralkyl resin, terpenephenolic resm, and naphthol novolak resm.
- Polyhydric phenolic resins include those which are produced by the condensation reaction of a phenolic compound and an aldehyde such as hydroxybenzaldehyde, crotonaldehyde, and glyoxal.
- Acid anhydrides include methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, pyromellitic anhydride, and nadic methyl anhydride.
- Amines include diethylenet ⁇ amine, sophoronediamme, diam ophenyl- methane, diammodiphenylsulfone, and dicyandiamide.
- the optional epoxy resm hardener should preferably be used in an amount less than 100 parts by weight for 100 parts by weight of the epoxy resin hardener of the present invention. It reduces the effect of the present invention if it is used in an excess amount.
- the epoxy resin hardener should be used in such an amount that it contains 0.5 to 2.0 moles of groups, preferably 0.7 to 1.2 moles of groups, which react with 1 mole of epoxy groups in all the epoxy resm components.
- the epoxy resin composition of the present invention may be incorporated with a variety of additives, such as cure accelerator, filler, coupling agent, flame retardant, plasticizer, solvent, reactive diluent, and pigment, according to need.
- additives such as cure accelerator, filler, coupling agent, flame retardant, plasticizer, solvent, reactive diluent, and pigment, according to need.
- Examples of the cure accelerator include lmidazoles such as 2- methylimidazole and 2-ethyl-4-methyl ⁇ m ⁇ dazole; amines such as 2,4,6- tris (dimethylaminomethyl)phenol, benzylmethylamine, DBU, and DCMU, and organic phosphorus compounds such as tributylphosphine, t ⁇ - phenylphosphine, and tn (d ⁇ methoxyphenyl)phosph ⁇ ne.
- lmidazoles such as 2- methylimidazole and 2-ethyl-4-methyl ⁇ m ⁇ dazole
- amines such as 2,4,6- tris (dimethylaminomethyl)phenol, benzylmethylamine, DBU, and DCMU
- organic phosphorus compounds such as tributylphosphine, t ⁇ - phenylphosphine, and tn (d ⁇ methoxyphenyl)phosph ⁇ ne.
- the filler examples include fused silica, crystalline silica, glass powder, alumina, and calcium carbonate.
- examples of the flame retardant include antimony trioxide and phosphoric acid.
- the epoxy resm composition may be rendered flame retardant by partly replacing the epoxy resin by a brommated epoxy res .
- the invention also relates to products applied with the cured epoxy res compositions according to the present invention and to products obtained by curing the before mentioned epoxy resin composition.
- the epoxy resm composition of the present invention yields a cured product having good moisture resistance, which is therefore advantageously used in the fields of adhesion, casting, potting, moulding, lamination, coating, and the like.
- Epoxy resin compositions were prepared according to the formulation shown in Table 2 from any of resin I (bisphenol A type epoxy resin) , resin II (o-cresolnovolak type epoxy resin) , and resin III (epoxy resin derived from tetramethylbiphenol), any of the epoxy resin hardeners obtained in Examples 1 to 3, hardener I (phenol novolak resin hardener) , and hardener II (methyltetrahydrophthalic anhydride hardener) , and a cure accelerator (2-methylimidazole) .
- the resulting epoxy resin composition was defoamed and casted into a mould. Upon curing at 180 °C for 8 hours, there were obtained test pieces. They were tested for moisture absorption and glass transition point. The results are shown in Table 2. It is noted that the test pieces in Examples 4 to 8 are much lower in moisture absorption than those in Comparative Examples 1 and 2.
- Epoxy resin hardener Example Example Example Example Hardene composi ⁇ Hardene (parts by weight) 1 2 3 1 1 r l * 4 tion r ll *5
- Cure accelerator (2- 1 1 1 1 1 1 1 1 1 methylimidazole) (parts by weight)
- Resin I bisphenol A type epoxy resin ("Epikote 828" having an epoxy equivalent of 186, from Yuka Shell Epoxy K.K.)
- Resin II o-cresol novolak type epoxy resin ("Epikote 180H65” having an epoxy equivalent of 201, from Yuka Shell Epoxy K.K.)
- Resin III epoxy resin derived from tetramethylbiphenol
- Hardener I phenol novolak resin, having a hydroxyl equivalent of 103 g/eq. and a softening point of 85 °C, a product of Gunei
- Hardener II methyltetrahydrophthalic anhydride *6 measured after immersion in water at 100 °C for 100 hours. *7 obtained from the transition point of the thermal expansion curve of TMA.
- the epoxy resin hardeners, the epoxy resin compositions, and epoxy resin curing process described above result in cured products having good moisture resistance. Therefore, they can be used advantageously in a broad range of applications including adhesion, casting, potting, lamination, moulding, and coating.
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95907626A EP0741752A1 (en) | 1994-01-28 | 1995-01-26 | Epoxy resin hardener, epoxy resin composition, and epoxy resin hardening process |
AU15770/95A AU1577095A (en) | 1994-01-28 | 1995-01-26 | Epoxy resin hardener, epoxy resin composition, and epoxy resin hardening process |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2495994 | 1994-01-28 | ||
JP6/24959 | 1994-01-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995020612A1 true WO1995020612A1 (en) | 1995-08-03 |
Family
ID=12152523
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/000305 WO1995020612A1 (en) | 1994-01-28 | 1995-01-26 | Epoxy resin hardener, epoxy resin composition, and epoxy resin hardening process |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0741752A1 (en) |
CN (1) | CN1168681A (en) |
AU (1) | AU1577095A (en) |
CA (1) | CA2182088A1 (en) |
MY (1) | MY130504A (en) |
WO (1) | WO1995020612A1 (en) |
ZA (1) | ZA95620B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6469109B2 (en) | 1994-08-30 | 2002-10-22 | Sumitomo Chemical Company, Limited | Aryl ester compound, its production process, epoxy resin composition using said compound, and copper-clad laminate using the epoxy resin composition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101815355B1 (en) | 2014-12-16 | 2018-01-04 | 주식회사 엘지화학 | Pressure sensitive adhsive composition |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6253327A (en) * | 1985-08-31 | 1987-03-09 | Res Dev Corp Of Japan | Curable composition |
EP0504108A2 (en) * | 1991-03-11 | 1992-09-16 | Ciba-Geigy Ag | Aromatic trisanhydrides |
JPH07121898A (en) * | 1993-10-27 | 1995-05-12 | Olympus Optical Co Ltd | Optical head |
-
1995
- 1995-01-13 MY MYPI95000082A patent/MY130504A/en unknown
- 1995-01-26 AU AU15770/95A patent/AU1577095A/en not_active Abandoned
- 1995-01-26 CA CA002182088A patent/CA2182088A1/en not_active Abandoned
- 1995-01-26 WO PCT/EP1995/000305 patent/WO1995020612A1/en not_active Application Discontinuation
- 1995-01-26 CN CN95191402A patent/CN1168681A/en active Pending
- 1995-01-26 ZA ZA95620A patent/ZA95620B/en unknown
- 1995-01-26 EP EP95907626A patent/EP0741752A1/en not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6253327A (en) * | 1985-08-31 | 1987-03-09 | Res Dev Corp Of Japan | Curable composition |
EP0504108A2 (en) * | 1991-03-11 | 1992-09-16 | Ciba-Geigy Ag | Aromatic trisanhydrides |
JPH07121898A (en) * | 1993-10-27 | 1995-05-12 | Olympus Optical Co Ltd | Optical head |
Non-Patent Citations (2)
Title |
---|
CHEMICAL ABSTRACTS, vol. 76, no. 14, 3 April 1972, Columbus, Ohio, US; abstract no. 73018, "Poly(ether esters)." page 16; * |
DATABASE WPI Derwent World Patents Index; AN 87-105465 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6469109B2 (en) | 1994-08-30 | 2002-10-22 | Sumitomo Chemical Company, Limited | Aryl ester compound, its production process, epoxy resin composition using said compound, and copper-clad laminate using the epoxy resin composition |
Also Published As
Publication number | Publication date |
---|---|
EP0741752A1 (en) | 1996-11-13 |
MY130504A (en) | 2007-06-29 |
ZA95620B (en) | 1995-10-05 |
CA2182088A1 (en) | 1995-08-03 |
AU1577095A (en) | 1995-08-15 |
CN1168681A (en) | 1997-12-24 |
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