WO2016029451A1 - Synthèse de novolaque de naphtol - Google Patents

Synthèse de novolaque de naphtol Download PDF

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Publication number
WO2016029451A1
WO2016029451A1 PCT/CN2014/085579 CN2014085579W WO2016029451A1 WO 2016029451 A1 WO2016029451 A1 WO 2016029451A1 CN 2014085579 W CN2014085579 W CN 2014085579W WO 2016029451 A1 WO2016029451 A1 WO 2016029451A1
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WIPO (PCT)
Prior art keywords
curable composition
weight percent
naphthol
accordance
novolac
Prior art date
Application number
PCT/CN2014/085579
Other languages
English (en)
Inventor
Lijing FANG
Guihong LIAO
Hongyu Chen
Chao Zhang
Michael J. Mullins
Original Assignee
Blue Cube Ip Llc
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 Blue Cube Ip Llc filed Critical Blue Cube Ip Llc
Priority to PCT/CN2014/085579 priority Critical patent/WO2016029451A1/fr
Priority to PCT/US2015/046748 priority patent/WO2016033079A1/fr
Priority to TW104128363A priority patent/TW201615678A/zh
Publication of WO2016029451A1 publication Critical patent/WO2016029451A1/fr

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    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
    • C—CHEMISTRY; METALLURGY
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    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
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    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
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Definitions

  • the present invention is related to epoxy resin compositions. More particularly, the present invention is related to halogen- free or substantially halogen-free formulations.
  • Epoxy resins are widely used in coatings, adhesives, printed circuit boards, semiconductor encapsulants, adhesives and aerospace composites thanks to the excellent mechanical strength; chemical, moisture, and corrosion resistance; good thermal, adhesive, and electrical properties.
  • Naphthol novolac (NPN) has been used as an epoxy hardener for electrical laminate applications.
  • NPN has been used as an epoxy hardener for electrical laminate applications.
  • the use of NPN can also greatly improve flame resistance and allows for a reduction in the amount of flame retardant used.
  • NPN has a high production cost and poor prepreg appearance which is attributed to high system viscosity. Therefore, a process to produce NPN that avoids these negative aspects would be desirable.
  • the instant invention is a method for making naphthol novolac comprising, consisting of, or consisting essentially of: contacting a) a naphthol component comprising i) from 1 to 99 weight percent 1 -naphthol; and ii) from 1 to 99 weight percent 2-naphthol; and b) an aldehyde
  • the instant invention is also a curable composition
  • a curable composition comprising, consisting of, or consisting essentially of: a) an epoxy resin; and b) a hardener component comprising i) an oligomeric compound comprising a phosphorus composition which is the reaction product of an etherified resole with 9, 10-dihydro-9-oxa- 10-phosphaphenanthrene- 10-oxide, and ii) a naphthol novolac prepared by the above method.
  • the instant invention is a method for making a naphthol novolac.
  • the instant invention is a method comprising, consisting of, or consisting essentially of contacting a) a naphthol component comprising i) from 1 to 99 weight percent 1 -naphthol; and ii) from 1 to 99 weight percent 2 -naphthol; and b) an aldehyde in a reaction zone under reaction conditions to form the naphthol novolac.
  • the reaction conditions can include a reaction temperature in the range of from 80°C to 160°C and a reaction time in the range of from 3 to
  • a naphthol component is contacted with paraformaldehyde to form naphthol novolac.
  • An example of the reaction scheme is depicted in Formula 1, below.
  • the naphthol novolac product is depicted as modified naphthol novolac (m-NPN).
  • paraformaldehyde can be used as the aldehyde.
  • aldehydes that can be used include, but are not limited to formaldehyde, aliphatic aldehydes, and aromatic aldehydes.
  • the naphthol component can be added to a solvent before contact with the aldehyde.
  • Any suitable solvent can be used such as, for example, toluene and xylene.
  • the reaction conditions include a reaction temperature in the range of from 80°C to 160°C. All individual ranges and subranges from 80°C to 160°C are included herein and disclosed herein, for example, the reaction temperature can be from a lower limit of 80°C, 90°C, 105°C, or 118°C to an upper limit of 90°C, 122°C, 135°C, 144°C, 153°C, or 160°C.
  • the reaction conditions also include a reaction time in the range of from 3 to 72 hours. All individual ranges and subranges from 3 hours to 72 hours are included herein and disclosed herein, for example, the reaction time can be from a lower limit of 3 hours, 6.5 hours, 8 hours, or 10 hours to an upper limit of 18 hours, 22 hours, 24 hours, 36 hours, 48 hours, and 72 hours.
  • the instant invention is a curable composition.
  • the instant invention is a curable composition comprising, consisting of, or consisting essentially of a) an epoxy resin; and b) a hardener component comprising i) an oligomeric compound comprising a phosphorus composition which is the reaction product of an etherified resole with 9,10- dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, and ii) a naphthol novolac prepared by the above method.
  • the curable composition can further include optionally a filler.
  • the curable composition can further include optionally a catalyst.
  • the curable composition comprises an epoxy resin and a hardener, as described in further details hereinbelow.
  • the curable composition may further include one or more fillers.
  • the curable composition may comprise 10 to 80 percent by weight of one or more fillers. All individual values and subranges from 10 to 80 weight percent are included herein and disclosed herein, for example, the weight percent of filler can be from a lower limit of 10, 12, 15, 20, or 25 weight percent to an upper limit of 62, 65, 70, 75, or 80 weight percent.
  • curable composition may comprise 15 to 75 percent by weight of one or more fillers; or in the alternative, curable composition may comprise 20 to 70 percent by weight of one or more fillers.
  • Such fillers include, but are not limited to natural silica, fused silica, alumina, hydrated alumina, and combinations thereof.
  • the curable composition may further include one or more catalysts.
  • the curable composition may comprise 0.01 to 50 percent by weight of one or more catalysts. All individual values and subranges from 0.01 to 50 weight percent are included herein and disclosed herein, for example, the weight percent of catalyst can be from a lower limit of 0.01, 0.03, 0.05, 0.07, or 1 weight percent to an upper limit of 2, 6, 10, 15, or 50 weight percent.
  • curable composition may comprise 0.05 to 10 percent by weight of one or more catalysts; or in the alternative, curable composition may comprise 0.05 to 2 percent by weight of one or more catalysts.
  • catalysts include, but are not limited to 2-methyl imidazole (2MI), 2-phenyl imidazole (2PI), 2-ethyl-4-methyl imidazole (2E4MI), l-benzyl-2- phenylimidazole (1B2PZ), boric acid, triphenylphosphine (TPP), tetraphenylphosphonium- tetraphenylborate (TPP-k) and combinations thereof.
  • the curable composition may further include one or more tougheners.
  • the curable composition may comprise 0.01 to 70 percent by weight of one or more tougheners. All individual values and subranges from 0.01 to 70 weight percent are included herein and disclosed herein, for example, the weight percent of toughener can be from a lower limit of
  • curable composition may comprise 1 to 50 percent by weight of one or more tougheners; or in the alternative, curable composition may comprise 2 to 30 percent by weight of one or more tougheners.
  • tougheners include, but are not limited to core shell rubbers.
  • a core shell rubber is a polymer comprising a rubber particle core formed by a polymer comprising an elastomeric or rubbery polymer as a main ingredient and a shell layer formed by a polymer graft polymerized on the core. The shell layer partially or entirely covers the surface of the rubber particle core by graft polymerizing a monomer to the core.
  • the rubber particle core is constituted from acrylic or methacrylic acid ester monomers or diene
  • the toughening agent may be selected from commercially available products; for example, Paraloid EXL 2650A, EXL 2655, EXL2691 A, each available from The Dow Chemical Company, or Kane Ace® MX series from Kaneka Corporation, such as MX 120, MX 125, MX 130, MX 136, MX 551, or METABLEN SX-006 available from Mitsubishi Rayon.
  • the curable composition comprises a) an epoxy resin; and b) a hardener component comprising i) an oligomeric compound comprising a phosphorus composition which is the reaction product of an etherified resole with 9, 10-dihydro-9-oxa- 10-phosphaphenanthrene- 10-oxide, and ii) napthol novolac.
  • the curable composition may comprise 10 to 90 percent by weight of one or more epoxy resins. All individual values and subranges from 10 to 90 weight percent are included herein and disclosed herein, for example, the weight percent of epoxy resin can be from a lower limit of 12, 17, 20, 30, or 35 weight percent to an upper limit of 55, 70, 86, 90, or 98 weight percent.
  • curable composition may comprise 20 to 98 percent by weight of one or more epoxy resins or in the alternative, curable composition may comprise 30 to 90 percent by weight of one or more epoxy resins.
  • the epoxy resin is a multifunctional epoxy which has more than two epoxy functionalities.
  • Such epoxy resins include, but are not limited to epoxy resins obtained by glycidifying the condensation product of a phenol or a napthol with an aldehyde, such as napthol novolac epoxies, epoxy resins obtained by glycidifying the co-condensation product of napthol, phenol, and formaldehyde, bisphenol-A novolac epoxies, bisphenol-F novolac epoxies and combinations thereof.
  • the present invention curable composition includes at least one epoxy resin.
  • the epoxy resin may be saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or
  • the epoxy resin may also be monomeric or polymeric.
  • the epoxy resins used in embodiments disclosed herein for component (a) of the present invention, may vary and include conventional and commercially available epoxy resins, which may be used alone or in combinations of two or more. In choosing epoxy resins for compositions disclosed herein, consideration should not only be given to properties of the final product, but also to viscosity and other properties that may influence the processing of the resin composition.
  • epoxy compounds include, but are not limited to epoxies based on reaction products of polyfunctional alcohols, phenols, cycloaliphatic carboxylic acids, aromatic amines, or aminophenols with epichlorohydrin.
  • a few non-limiting embodiments include, for example, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, resorcinol diglycidyl ether, and triglycidyl ethers of para-aminophenols.
  • Other suitable epoxy resins known to the skilled worker include reaction products of epichlorohydrin with o-cresol and, respectively, phenol novolacs.
  • Further epoxy resins include epoxides of divinylbenzene or divinylnaphthalene. It is also possible to use a mixture of two or more epoxy resins.
  • the epoxy resins useful in the present invention may be selected from commercially available products; for example, D.E.R®. 331, D.E.R. 332, D.E.R. 383, D.E.R. 334, D.E.N. 431, D.E.N. 438, D.E.R. 736, or D.E.R. 732 epoxy resins available from The Dow Chemical Company or Syna 21 cycloaliphatic epoxy resin from Synasia.
  • the curable composition may comprise 1 to 90 percent by weight of naphthol novolacs prepared by the method mentioned above (afterwards referred to as 'modified naphthol novolac' or 'm-NPN'). All individual values and subranges from 1 to 90 weight percent are included herein and disclosed herein, for example, the weight percent of m-NPN can be from a lower limit of 1, 1.2, 1.5, 12, or 20 weight percent to an upper limit of 45, 50, 54, 60, or 70 weight percent.
  • curable composition may comprise 1 to 60 percent by weight of one or more m-NPNs or in the alternative, curable composition may comprise 1 to 50 percent by weight of one or more m-NPNs.
  • the curable composition may comprise 1 to 80 percent by weight of one or more oligomeric compounds comprising a phosphorus composition which is the reaction product of an etherified resole with 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO). All individual values and subranges from 1 to 80 weight percent are included herein and disclosed herein, for example, the weight percent of DOPO compound can be from a lower limit of 1.5, 2, 3, 5, or 10 weight percent to an upper limit of 20, 40, 55, 60, or 70 weight percent.
  • curable composition may comprise 2 to 60 percent by weight of one or more DOPO compound or in the alternative, curable composition may comprise 5 to 40 percent by weight of one or more DOPO compound.
  • the DOPO-containing compound is an oligomeric composition comprising a phosphorus-containing compound which is the reaction product of an etherified resole with 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide ( ⁇ -DOP').
  • ⁇ -DOP' 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
  • the curable composition can contain a solvent.
  • Solvents can be used to solubilize the epoxy and hardener component or to adjust the viscosity of the final varnish.
  • solvents include, but are not limited to methanol, acetone, n-butanol, methyl ethyl ketone (MEK), cyclohexanone, benzene, toluene, xylene, dimethylformamide (DMF), ethyl alcohol (EtOH), propylene glycol methyl ether (PM), propylene glycol methyl ether acetate (DOWANOLTM PMA) and mixtures thereof.
  • solvents include, but are not limited to methanol, acetone, n-butanol, methyl ethyl ketone (MEK), cyclohexanone, benzene, toluene, xylene, dimethylformamide (DMF), ethyl alcohol (EtOH), propylene glycol
  • the curable composition can be produced by any suitable process known to those skilled in the art.
  • solutions of the epoxy component, phosphorus- containing compound, and polymeric anhydride are mixed together. Any other desired component, such as the optional components described above, are then added to the mixture.
  • Embodiments of the present disclosure provide prepregs that includes a reinforcement component and the curable composition, as discussed herein.
  • the prepreg can be obtained by a process that includes impregnating a matrix component into the reinforcement component.
  • the matrix component surrounds and/or supports the reinforcement component.
  • the disclosed curable compositions can be used for the matrix component.
  • the component and the reinforcement component of the prepreg provide a synergism.
  • This synergism provides that the prepregs and/or products obtained by curing the prepregs have mechanical and/or physical properties that are unattainable with only the individual components.
  • the prepregs can be used to make electrical laminates for printed circuit boards.
  • the reinforcement component can be a fiber.
  • fibers include, but are not limited to, glass, aramid, carbon, polyester, polyethylene, quartz, metal, ceramic, biomass, and combinations thereof.
  • the fibers can be coated.
  • An example of a fiber coating includes, but is not limited to, boron.
  • glass fibers include, but are not limited to, A-glass fibers, E-glass fibers, C-glass fibers, R-glass fibers, S-glass fibers, T-glass fibers, and combinations thereof.
  • Aramids are organic polymers, examples of which include, but are not limited to, Kevlar®, Twaron®, and combinations thereof.
  • carbon fibers include, but are not limited to, those fibers formed from polyacrylonitrile, pitch, rayon, cellulose, and combinations thereof.
  • metal fibers include, but are not limited to, stainless steel, chromium, nickel, platinum, titanium, copper, aluminum, beryllium, tungsten, and combinations thereof.
  • ceramic fibers include, but are not limited to, those fibers formed from
  • biomass fibers include, but are not limited to, those fibers formed from wood, non-wood, and combinations thereof.
  • the reinforcement component can be a fabric.
  • the fabric can be formed from the fiber, as discussed herein. Examples of fabrics include, but are not limited to, stitched fabrics, woven fabrics, and combinations thereof.
  • the fabric can be unidirectional, multiaxial, and combinations thereof.
  • the reinforcement component can be a combination of the fiber and the fabric.
  • the prepreg is obtainable by impregnating the matrix component into the
  • Impregnating the matrix component into the reinforcement component may be accomplished by a variety of processes.
  • the prepreg can be formed by contacting the reinforcement component and the matrix component via rolling, dipping, spraying, or other such procedures.
  • the solvent can be removed via volatilization.
  • the prepreg matrix component can be cured, e.g. partially cured. This volatilization of the solvent and/or the partial curing can be referred to as B-staging.
  • the B-staged product can be referred to as the prepreg.
  • B-staging can occur via an exposure to a temperature of 60 °C to 250 °C; for example B-staging can occur via an exposure to a temperature from 65 °C to 240 °C , or 70 °C to 230 °C.
  • B-staging can occur for a period of time of 1 minute (min) to 60 min; for example B-staging can occur for a period of time from, 2 min to 50 min, or 5 min to 40 min.
  • the B-staging can occur at another temperature and/or another period of time.
  • One or more of the prepregs may be cured (e.g. more fully cured) to obtain a cured product.
  • the prepregs can be layered and/or formed into a shape before being cured further.
  • layers of the prepreg can be alternated with layers of a conductive material.
  • An example of the conductive material includes, but is not limited to, copper foil.
  • the prepreg layers can then be exposed to conditions so that the matrix component becomes more fully cured.
  • One example of a process for obtaining the more fully cured product is pressing.
  • One or more prepregs may be placed into a press where it subjected to a curing force for a predetermined curing time interval to obtain the more fully cured product.
  • the press has a curing temperature in the curing temperature ranges stated above.
  • the press has a curing temperature that is ramped from a lower curing temperature to a higher curing temperature over a ramp time interval.
  • the one or more prepregs can be subjected to a curing force via the press.
  • the curing force may have a value that is 10 kilopascals (kPa) to 350 kPa; for example the curing force may have a value that is 20 kPa to 300 kPa, or 30 kPa to 275 kPa.
  • the predetermined curing time interval may have a value that is 5 s to 500 s; for example the predetermined curing time interval may have a value that is 25 s to 540 s, or 45 s to 520 s.
  • the process may be repeated to further cure the prepreg and obtain the cured product.
  • the prepregs can be used to make composites, electrical laminates, and coatings.
  • Printed circuit boards prepared from the electrical laminates can be used for a variety of applications. In an embodiment, the printed circuit boards are used in smartphones and tablets. In various embodiments, the electrical laminates have a copper peel strength in the range of from 4 lb/in to 12 lb/in.
  • Table 2 shows the GPC results of naphthol novolac compositions prepared under different conditions.
  • Comparative Example A was prepared using the Comparative Synthesis and Comparative Example B was prepared using the Inventive Synthesis.
  • Examples 1-4 were all prepared using the Inventive Synthesis.
  • the molecular weight of m-NPN could be controlled by the reaction time and the molar ratio of 1 -naphthol and 2-naphthol. Since 2- naphthol tended to dimerize in the reaction with formaldehyde, increasing the ratio of 2- naphthol in the starting material resulted in the decrease of molecular weight of the product. Shortening the reaction time also resulted in a naphthol novolac composition having a lower molecular weight.
  • DENTM ('DEN') 438 (XZ 92748): phenol novolac type epoxy, from The Dow Chemical Company; DOP-BN (XZ 92741), hardener containing phosphorus, from The Dow Chemical Company;
  • Naphthol Novolac NPN
  • Modified Naphthol Novolac m-NPN
  • 2MI curing catalyst (10% in methanol), from Sigma-Aldrich.
  • NPN/m-NPN 152 0.7600 0.0050 60% 1.2667
  • the above ingredients were mixed according to the above formulation and shaken to form a uniform solution.
  • the catalyst was then added to the varnish, and gel time of the varnish was tested on a hot plate maintained at 171 °C.
  • the gelled material was recovered from the hot plate surface and post-cured in an oven at 200°C for 3 hours.
  • the glass transition temperature (T g ) of the cured material was measured by DSC.
  • DSC Differential scanning calorimetry
  • DSC experiments were carried out using a DSC-Q2000 instrument under a flowing nitrogen atmosphere (50 ml/min). About 10 mg cured resin was used in the examination. A dynamic temperature scan from 40°C to 280°C was applied at a heating rate of 10°C/min. Two scans were obtained using the same ramp rate.
  • DMTA Dynamic Mechanic Thermal Analysis
  • the glass transition temperature (T g ) of the laminate was also measured by dynamic mechanic thermal analysis (DMTA).
  • DMTA dynamic mechanic thermal analysis
  • Formulations having different multifunctional epoxy resins were tested for thermal properties.
  • the multifunctional epoxy resins were screened in small amounts (ca. total 3.0 g of varnish).
  • DOP-BN was also added to the formulations to adjust the phosphorous content to a certain level for flame retardant (FR) properties.
  • FR flame retardant
  • Laminate based on Example 10 was prepared.
  • the detailed varnish formulation is listed in Table 6.
  • the polymer ingredients were mixed to form a uniform 60% solution in cyclohexanone. The above mixture was shaken for 1 hour.
  • the varnish was then painted on glass fiber sheets (Hexcel 7628) and partially cured at 171°C in a ventilated oven for a suitable time (generally, about 3 minutes) to make prepregs. Finally, 8 pieces of prepregs were hot pressed at 200 °C for one hour to make a hand-painted laminate, the laminate was post cured at 200°C for another two hours.

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  • Health & Medical Sciences (AREA)
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Abstract

L'invention concerne un procédé de production de novolaque de naphtol, qui comprend, consiste à, ou consiste essentiellement à: mettre en contact dans une zone de réaction a) un constituant naphtol comprenant i) 1 à 99 pour cent en poids de 1-naphtol, et ii) 1 à 99 pour cent en poids de 2-naphtol; et b) un aldéhyde, dans des conditions de réaction, pour former la novolaque de naphtol. L'invention concerne également une composition durcissable qui comprend, est constitué ou est constitué essentiellement de: a) une résine époxyde; et b) un constituant durcisseur comprenant: i) une composition oligomère comprenant un composé phosphoré qui est le produit de réaction d'un résol étherifié avec 9,10-dihydro-9-oxa-10-phosphaphénanthrène-10-oxyde, et ii) une novolaque de naphtol préparé par le procédé ci-dessus. La composition durcissable peut être utilisée pour préparer des préimprégnés et des stratifiés électriques.
PCT/CN2014/085579 2014-08-29 2014-08-29 Synthèse de novolaque de naphtol WO2016029451A1 (fr)

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