Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • 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
  • C08G59/20—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 epoxy compounds used
  • C08G59/22—Di-epoxy compounds
  • C08G59/24—Di-epoxy compounds carbocyclic
  • C08G59/245—Di-epoxy compounds carbocyclic aromatic
• • 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
  • C08G59/20—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 epoxy compounds used
  • C08G59/32—Epoxy compounds containing three or more epoxy groups
  • C08G59/3218—Carbocyclic compounds
• • 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
  • 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

• This invention relates to adhesives and more specifically to a curable adhesive that contains protected phenolics, small molecules, oligomers, and polymers.
• Phenolic-epoxy adhesives have been known for over 50 years and were one of the first high temperature adhesives to become commercialized. Once cured, the material retains its adhesive properties over a large range of temperatures, has high shear strengths, and is resistant to weathering, oil, solvents, and moisture.
• the adhesive is available commercially as either a 1-part adhesive or 2-part adhesive and is available in several forms, such as pastes, solvent solutions, and supported films. Of the three forms, the adhesive film generally provides better adhesive strength
• both phenolic and epoxy are combined by the manufacturer and is available to the consumer as a single component.
• the adhesive suffers from a shortened useable lifetime, also known as shelf-life, at room temperature because the highly reactive phenolic immediately initiates the cure chemistry of the epoxy once it is added. This effect is even more pronounced at temperatures above room temperature, where the useable lifetime of the adhesive can be reduced to minutes.
• shelf life is so short that films must be stored under refrigerated conditions before use, as described by Petrie in "Epoxy Adhesive Formulations", McGraw- Hill publishers, 2006.
• the manufacturer of a 1-part adhesive and can also experience a reduced time to manufacture the adhesive because the phenolic quickly begins to cause an increase in solution viscosity as it starts to react with the epoxy, and, if care is not taken, the viscosity will continue to increase until a point is reached at which the processability is severely compromised.
• Phenolics are also reactive toward benzoxazines and have been used to decrease the polymerization temperature, as demonstrated in US 6,207,786, of Ishida et al., where the polymerization temperature was lowered from 190 0 C to 145 0 C after the addition of phenol.
• the phenolic in this case functions as a polymerization initiator, or curative, for benzoxazine, in a similar manner as phenols initiate the cross-link chemistry of epoxies.
• alkyl isocyante is a gaseous compound that is harmful and detrimental to human health, in addition to performing as a low molecular weight contaminate that is free to migrate and cause a decrease in the performance of the adhesive.
• the advantage of a reactive epoxy as a byproduct is that is becomes incorporated into the adhesive matrix during the curing process and it would therefore not cause a decrease in Tg nor adversely affect the performance of the adhesive
• the mixtures described above would have benefit in composites, molding compounds, adhesives and coatings, particularly for electronic applications, which include, but are not limited to underfill materials, electronic packaging, encapsulation, die attach adhesives, conductive adhesives, lead free solders, anisotropic conducting films (ACFs) and non- conductive adhesive films (NCFs). Said compositions would find benefit in electronic displays, circuit boards, flip chip, and other semiconductor devices.
• One desirable composition consists of from 0.1 to 90 weight percent of a protected phenolic and 0.1 to 90 weight percent of an epoxy.
• the composition can be used with 0.1 to 40 weight percent of a deblocking agent to facilitate the release of the phenolic.
• the composition can contain one or more of 0.1 to 20 weight percent of fillers, 0.1 to 20 weight percent of adhesion promoters, 0.1 to 20 weight percent of silane coupling agents, 0.1 to 20 weight percent pigments, 0.1 to 20 weight percent dyes, and 0.1 to 20 weight percent electrically conducting particles.
• Another desirable composition consists of from 0.1 to 90 weight percent of a protected phenolic and 0.1 to 90 weight percent of a benzoxazine.
• the composition can be used with 0.1 to 40 weight percent of a deblocking agent to facilitate the release of the phenolic.
• the composition can contain one or more of 0.1 to 20 weight percent of fillers, 0.1 to 20 weight percent of adhesion promoters, 0.1 to 20 weight percent of silane coupling agents, 0.1 to 20 weight percent pigments, 0.1 to 20 weight percent dyes, and 0.1 to 20 weight percent electrically conducting particles.
• Yet another desirable composition consists of from 0.1 to 90 weight percent of a protected phenolic, 0.1 to 90 weight percent of a epoxy, and 0.1 to 90 weight percent of a benzoxazine.
• the composition can be used with 0.1 to 40 weight percent of a deblocking agent, to facilitate the release of the phenolic.
• the composition can contain one or more of 0.1 to 20 weight percent of fillers, 0.1 to 20 weight percent of adhesion promoters, 0.1 to 20 weight percent of silane coupling agents, 0.1 to 20 weight percent pigments, 0.1 to 20 weight percent dyes, and 0.1 to 20 weight percent electrically conducting particles.
• FIG. 1 depicts an example of an aryl glycidyl carbonate
• FIG. 2 depicts a glycidyl carbonate functional group
• FIG. 3 depicts possible chemical structures for the aryl glycidyl carbonates shown in FIG. 1;
• FIG. 4 depicts Scheme 1 for deprotection of a protected phenol
• FIG. 5 depicts Scheme 2 for pyrolysis of aryl alkyl carbamates
• FIG. 6 depicts the chemical structure of oxirane moieties
• FIG. 7 depicts an example of the synthesis of a simple benzoxazine
• FIG. 8A and 8B depict possible chemical structures for benzoxazines
• FIG. 9 depicts Example 1 regarding a protected phenolic
• FIG. 10 depicts Example 2 regarding a protected phenolic
• FIG. 11 depicts Example 3 regarding a protected phenolic
• FIG. 12 depicts Examples 4a and 4b regarding a protected phenolic
• FIG. 13 depicts Examples 5a and 5b regarding a protected phenolic
• FIG. 14 depicts Example 6 regarding a protected phenolic
• FIG. 15 depicts Example 7 regarding a protected phenolic
• FIG. 16 depicts Example 8 regarding a protected phenolic
• FIG. 17 depicts Example 9 regarding a benzoxazine
• FIG. 18 depicts Example 10 regarding a benzoxazine
• FIG. 19 depicts Example 11 regarding a benzoxazine
• FIG. 20 depicts Example 12 regarding a benzoxazine
• FIG. 21 depicts Example 13 regarding a benzoxazine
• FIG. 22 depicts Example 14 regarding a benzoxazine
• FIG. 23 depicts Example 15 regarding a benzoxazine
• FIG. 24 depicts Example 16 regarding epoxies.
• the protected phenolics described herein refer to any phenolic compound that has been converted to an aryl glycidyl carbonate as shown in FIG. 1.
• the protected phenol can contain one or more glycidyl carbonate functional groups, where the glycidyl carbonate is defined according to FIG. 2.
• the aryl glycidyl carbonate shown in FIG. 1 includes, but is not limited to, the chemical structures shown in FIG. 3, where G 1 is one or more glycidyl carbonate groups shown in FIG. 2; G 2 , G 3 , G 4 , G 5 , G 6 are H and one or more glycidyl carbonate groups shown in FIG.
• R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are one or more H, F, Cl, Br, I, CH 3 , alkane, alkene, alkyne, any structure shown in FIG 6, OR 13 , OAr 1 , CO 2 R 13 , CO 2 Ar 1 , C(O)NHR 13 , C(O)NHAr 1 , C(O)NR 13 R 14 , C(O)NAr 1 Ar 2 , OC(O)R 13 , OC(O)Ar 1 , NHC(O)R 13 NHC(O)Ar 1 , NR 13 C(O)R 14 , NAr 1 C(O)R 13 , NAr 1 C(O)Ar 2 , SR 13 , SAr 1 , where R 13 and R 14 are CH 3 , alkane, alkene, alkyne; Ar 1 and Ar 2 are any aromatic chemical moiety or any heterocyclic chemical moiety; R 7 , R 8 ,
• one or more of the sp 2 -hybridized carbon atoms of the chemical structures shown in FIG. 3 can be replaced with N, P, or combinations thereof.
• FIG. 4 depicts Scheme 1, where the deprotection of the glycidyl carbonate is caused by the addition of a deblocking agent B and where the deblocking agent reacts either directly or indirectly with the oxirane thereby releasing the phenolic (19), in addition to oxirane (20), and carbon dioxide, (21). This could be accomplished by various theories.
• the deblocking agent can be a catalyst or curing agent of the type used to accelerate the cure rate of epoxy-based adhesives, such as alkyl amines, aromatic amines, imidazoles, triazoles, triazines, melamines, other classes of heterocyclic amines, amine-containing siloxanes, amine-epoxy adducts, imidiazole-epoxy adducts, mercaptans, alkoxides, hydroxides, or combinations thereof.
• boron halides, aluminum halides, titanium halides, and other Lewis acids could be added to assist with the ring- opening of the oxirane and thereby initiate the release of the phenolic.
• the deblocking agent can also be a latent catalyst, as described in US
• the protected phenolics described above can also perform as a source for the controlled release of phenolics.
• the phenols thus released may consequently be used as for examples, developers or inhibitors for applications including, but are not limited to, development of silver halides for imaging applications, inhibition of radical polymerization or redox reactions, and antioxidation.
• the deblocking agent can be added all at once or metered at a rate that is commensurate to accommodate the release rate of the phenolic as desired by the end-user.
• Substituting the Ar-O of the carbonate as depicted in FIG. 4 (Scheme 1) with Ar-S, Ar-NH, Ar-NAr, or Ar-NR would also be useful as sources for the controlled release of aryl mercaptans and aryl amines.
• FIG. 5 depicts Scheme 2, where, in addition to aryl glycidyl carbonates, another source for the controlled release of phenolics can result from the thermal decomposition of aryl alkyl carbamates as described by US 4,123,450 of Weber and WO 87/05600 of Chan.
• the alkyl isocyante is a gaseous compound that is harmful and detrimental to human health.
• the only byproducts for the release of the phenolics using aryl glycidyl carbonates (Scheme 1) is CO 2 and an epoxy, where said epoxy is considerably less volatile and less toxic than the corresponding alkyl isocyanate and has the additional advantage of becoming incorporated into the adhesive, composite matrix, or coating.
• the epoxies described herein refer to the chemical structures of FIG. 3, where G 1 is one or more of the chemical structures shown in FIG. 6; G 2 , G 3 , G 4 , G 5 , G 6 are H and one or more of the chemical structures shown in FIG.
• R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are one or more H, F, Cl, Br, I, CH 3 , alkane, alkene, alkyne, OR 13 , OAr 1 , CO 2 R 13 , CO 2 Ar 1 , C(O)NHR 13 , C(O)NHAr 1 , C(O)NR 13 R 14 , C(O)NAr 1 Ar 2 , OC(O)R 13 , OC(O)Ar 1 , NHC(O)R NHC(O)Ar, NR 13 C(O)R 14 , NAr 1 C(O)R 13 , NAr 1 C(O)Ar 2 , SR 13 , SAr 1 , where R 13 and R 14 are CH3, alkane, alkene, alkyne, Ar 1 and Ar 2 are any aromatic chemical moiety or any heterocyclic chemical moiety; R 7 , R 8 , R 9 , R 10 , R 11 ,
• Benzoxazines are heterocyclic compounds that when polymerized exhibit good heat resistance, low water absorption, little outgassing, low dielectric constants, and exhibit little shrinking, which is what makes them attractive for electronic applications.
• the polymerization can be initiated cationically through the use of catalysts as described in US 6,899,960 and US 7,179,684 of Shi et al. and US 6,225,440 of Ishida.
• Benzoxazines are also known to undergo thermally initiated polymerizations at high temperatures (150 to 300 0 C). We have found unexpectedly that this temperature can be reduced when a benzoxazine is heated in the presence of a protected phenolic, as shown in Table 4 (below).
• Benzoxazines are synthesized from phenols using the Mannich reaction, with at least one position ortho to the phenolic hydroxyl is unsubstituted, as described in GB 694,480 of Lane, US 5,543,516 of Ishida, and US 6,743,852 of Dershem.
• a representation of a simple benzoxazine (Bl) is shown in FIG. 7.
• the benzoxazines for one embodiment of the invention have one or more benzoxazine moieties attached at two adjacent sp 2 -hybridized carbon atoms of an aromatic compound.
• the benzoxazines can include, but are not limited to, the chemical structures of FIGs.
• Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , and Ar 6 are benzene, toluene, or any aromatic compound
• R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , F 8 , R 9 , R 10 , R 11 , and R 12 are one or more H, CH 3 , any alkane, alkene, or alkyne
• X and Y are N-H, N-R, where R is any alkane, N-Ar, where Ar is benzene, toluene, or any aromatic compounds, S, or O
• h is an integer 1 or 2
• g, i, j, k, 1 are integers 0, 1, or 2
• n is an integer greater than or equal to 0
• m is an integer greater than or equal to 1.
• the fillers can include, but are not limited to glass fibers, cellulose fibers, wood or bamboo chips, silica, alumina, talcs (magnesium silicate), barites (barium sulfate), clays (aluminum silicate), calcium carbonate, boron nitride, silicone nitride, aluminum nitride, and titanium dioxide.
• Coupling agents may be used to improve the wet adhesion and performances in high humidity environment.
• Useful coupling agents for the present invention include, but are not limited to, glycidoxypropyltimethoxysilane, glycidoxypropyltiethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropyltrimethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane, acryloxypropyltriethoxysilane, acryloxypropyltrimethoxysilane, and ⁇ -mercaptopropyltrimethoxysilane.
• the coupling agents having amino or oxirane functional groups are preferred for electronics. Titanate or zirconate coupling agents may also be used particularly when fillers having no metal oxide or hydroxide functionality on the surface are employed.
• the electrically or thermally conducting particles can include, but are not limited to, carbon, nano tubes of carbon, graphite, and composites or blends comprising Zn, Al, Sb, Au, Ag, Sn, Fe, Cu, Pb, Ni, and Pt metals or metal oxides, and conductive particles having a polymeric or inorganic core and a metallic shell.
• the workable lifetime of the invention is described as a period of time in which during preparation of the composition, also known as the pot life, the composition is still able to be processed into an adhesive.
• the workable lifetime is further described as a period of time, after the composition has been processed, assembled, and ready for use, it maintains its ability to function as an adhesive.
• the chloroformate Pl was prepared according to US 2,795,572, Muller et al; with the exception that phosgene was replaced with triphosgene. See FIG. 9.
• a three-necked round bottom flask, equipped with a reflux condenser, an addition funnel, and a nitrogen gas inlet is charged with 25.00 g (0.160 mole) of phenyl chloroformate and 70 g of THF.
• the reactor was placed in a 0 0 C bath and purged with nitrogen. After 30 minutes, a solution of 13.00 g (0.175 mole) glycidol, 19.50 g (0.193 mole) triethylamine, and 75 g of anhydrous tetrahydrofuran (THF) was added drop wise over the course of one hour, after which the reaction was allowed to warm to room temperature and allowed to stir overnight under a nitrogen atmosphere.
• THF anhydrous tetrahydrofuran
• the dicarbonate P3 was obtained from 18.10 g (0.0501 mole) of bisphenol-A bis (chloroformate) and 7.17 g (0.0968 mole) of glycidol using the procedure of Example 2 to afford 20.98 g of crude product, which was purified by dissolving the crude material in toluene and extracting with 0.1 N NaOH, followed by 0.1 N HCl, and finally with water and brine. The toluene layer was dried over MgSO 4 , filtered, and evaporated to dryness. See FIG. 11.
• Example 4a synthesis of diglycidyl 4,4'-cyclohexylidenebisphenol dicarbonate (P4).
• the dicarbonate P4 was synthesized from 23.45 g (0.0596 mole) of 4,4'- cyclohexylidenebisphenol bis(chloroformate) and 8.65 g (0.168 mole) glycidol according to the procedure of Example 2 to afford 27.72 of crude material, which was purified according to Example 3. See FIG. 12.
• the temperature of the reaction was reduced to -3 0 C and a solution of 13.42 g (0.0500 mole) 4,4'-cyclohexylidenebisphenol, 10.12 g triethylamine, and 80 mL of anhydrous tetrahydrofuran was added drop-wise over the course of one hour.
• the reaction was allowed to warm to room temperature and allowed to stir under a nitrogen atmosphere overnight.
• reaction is filtered and evaporated to dryness to afford 22.25 g of crude material that was purified by dissolving in toluene and extracted once with 0.1N NaOH, followed by 0.1N HCl, water, and brine. The organic layer was dried over MgSO 4 , filtered, and evaporated to dryness.
• Example 5a synthesis of diglycidyl 4,4'-[9-fluorenylidene]diphenol dicarbonate (P5).
• the dicarbonae P5 was synthesized from 25.67 g (0.0540 mole) 4,4'-(9- fluorenylidene)diphenol bis(chloroformate) and 7.84 g (0.106 mole) of glycidol using the procedure of Example 2 to afford 26.75 g of crude material, which was purified according to Example 3. See FIG. 13.
• Example 5b alternate synthesis of diglycidyl 4,4'-[9- fluorenylidene]diphenol dicarbonate.
• the dicarbonate P5 was also synthesized from 10.52 g (0.0300 mole)
• the tris(carbonate) P6 was synthesized from 13.76 g (0.0449 mole) l,l,l-tris(4-hydroxyphenyl)ethane and 18.40 g (0.135 mole) Pl and afforded 23.15 g of crude material according to the procedure of Example 4b. See FIG. 14.
• the dicarbonate P7 is synthesized from 38.6 g (0.100 mole) of 4,4- dihydroxybiphenyl, 27.32g (0.200 mole) of Pl, and 200 mL of anhydrous THF according to the procedure of Example 4b. See FIG. 15.
• Polyphenol is synthesized from the polymerization of phenol using horseradish peroxidase according to US 5,212,044 of Liang, et al. Using the procedure of Example 4b, the poly(glycidyl carbonate) P8 is synthesized 15.00 g (0.100 mole) of polyphenol, 13.66 g (0.100 mole) of Pl, and 200 mL of anhydrous THF.
• Benzoxazine B3 was synthesized from 13.42 g (0.05 mole) 4,4'- cyclohexylidenebisphenol, 6.00 g (0.2 mole) paraformaldehyde, and 9.31 g (0.1 mole) aniline and afforded 24.0 g (95.5% yield) of a colored solid, using the procedure described in Example 10. See FIG. 19.
• Benzoxazine B4 was synthesized from 17.52 g (0.05 mole) 4,4'-(9- fluorenylidene)diphenol, 6.00 g (0.2 mole) paraformaldehyde), and 9.31 g (0.1 mole) of aniline, using the procedure described in Example 10 and afforded 28.06 g (96.0 % yield) of a colored solid. See FIG. 20.
• Example 13 synthesis of benzoxazine from poly(p-hydroxystyrene) and aniline (B5)
• Polybenzoxazine B5 was synthesized from 6.0 g (0.05 mole) Poly(4- vinylphenol), 3.0 g (0.1 mole) paraformaldehyde, and 4.68 g (0.05 mole) aniline according to the procedure described in Example 10 and afforded 11.4 g, (96.0 % yield) of a colored solid. See FIG. 21.
• Benzoxazine B6 is synthesized from 18.6 g (0.100 mole) of 4,4- dihydroxybiphenyl, 12.00 g (0.400 mole) paraformaldehyde, and 18.62 g (0.200 mole) of aniline according to the procedure of Example 10. See FIG. 22.
• Polybenzoxazine B7 is synthesized from 15.00 g (0.100 mole) of polyphenol, 12.00 g (0.400 mole) paraformaldehyde, and 18.62 g (0.200 mole) of aniline according to the procedure of Example 10. See FIG. 23.
• Example 16 chemical structures of epoxies used in combination with protected phenolics and benzoxazines.
• Example 18 deprotection of protected phenolics in the presence of imidazoles, results from TGA.
• a composition of a one to one molar ratio of P2 and 2-ethyl-4- methylimidazole is heated for two hours at 100 0 C and then evaluated for the release of phenol using the ferric chloride test of Shriner et al, "The Systematic Identification of Organic Compounds"; 6th ed.; Wiley: New York, 1980; pp 348-350. As expected, a purple color was produced indicating formation of an iron complex and the presence of phenol.
• a sample of the aforementioned composition was analyzed by thin layer chromatography using a silica gel stationary phase and eluted withl: l weight ratio of ⁇ o-propyl acetate and hexane. Comparison of the R f value [(distance traveled by the compound)/(distance traveled by the solvent front)] of the mixture relative to phenol also indicated the presence of phenol in the mixture.
• Example 20 Compositions-glycidyl carbonates, benzoxazine, epoxies, and imidazoles
• compositions 1 through 20 are prepared by thoroughly mixing the components according to the molar ratios as shown in Table 3.
• Example 21 Compositions-glycidyl carbonates, benzoxazine, epoxies, and microencapsulated deblocking agent
• compositions 21-26 are prepared by thoroughly mixing the components according to the molar ratios as shown in Table 4.
• the micro-encapsulated deblocking agent that is used is latent hardeners HX-3721 (LHl), HX-3741 (LH2), and HX-3748 (LH 3), respectively, which are obtained from Asahi Kasei Chemicals Corporation.
• compositions of glycidyl carbonates, benzoxazine, epoxies, and imidazoles were prepared by thoroughly mixing of the components of Table 3. They were then loaded into Al DSC pans, loaded into the DSC, and while under a nitrogen atmosphere heated in the temperature range 25 to 325 0 C using a heating ramp of 5 °C/min. The results are shown in Table 4.
• compositions 7 and 8 show the polymerization of benzoxazine is reduced by about 20 0 C in the presence of a protected phenolic.
• the curable compositions described above are provided in cured form and included in manufactured products such as electronic components, electronic displays, circuit boards, flip chips, and semiconductor devices.
• the compositions are provided in uncured or partially cured form to be used in these and other products before they are fully manufactured and assembled.

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