Abrasive tool making process – material – or composition – With synthetic resin
Reexamination Certificate
2003-01-30
2004-08-03
Sergent, Rabon (Department: 1711)
Abrasive tool making process, material, or composition
With synthetic resin
C051S309000, C051S293000, C264S478000, C264S494000, C264S496000, C428S500000, C524S430000, C524S440000, C524S441000, C524S432000, C524S433000, C524S436000, C524S437000, C524S438000, C525S132000, C525S390000, C525S391000, C525S397000, C528S137000, C528S138000, C528S139000, C528S154000, C528S159000, C528S160000, C528S161000
Reexamination Certificate
active
06770107
ABSTRACT:
BACKGROUND OF INVENTION
Abrasive-filled resins are known and employed in the fabrication of abrasive tools such as cutting and grinding wheels. Grinding wheels containing superabrasive materials (e.g., diamond or cubic boron nitride, CBN) in the edge or outer periphery of a circular grinding wheel or grinding cup also are well-known in the fields of sawing, drilling, dressing, grinding, lapping, polishing, and other abrading applications. For these applications, the grit typically is surrounded in a matrix of a metal, such as Ni, Cu, Fe, Co, Sn, W, Ti, or an alloy thereof, or in a resin, such as phenol formaldehyde or other thermosetting polymeric material. By attaching the matrices to a body or other support, tools may be fabricated having the capability to cut through such hard, abrasive materials as concrete, asphalt, masonry, ceramic, brick, granite, marble, and other rock. A typical such wheel is formed from a central metal disk having an aperture or a spindle for spinning the wheel in use. The outer periphery of the wheel, then, has a diamond-containing matrix bonded thereto. For wheels where the diamond is surrounded by a resin, the operator often cures the resin and bonds the resinous segments to the inner wheel by compression molding. Conventional bonding resins are used.
U.S. Pat. No. 5,167,674 describes grinding wheels manufactured from a conventional inner core to which is adhesively bonded a mixture of superabrasive grit, a bis-maleimide-trlazine addition copolymer resin, free-radical initiator, and catalyst. This mixture is compression molded to form a grinding segment annulus.
U.S. Pat. No. 5,314,512 describes injection molding of saw segments from superabrasive particles and a non-porous thermoplastic polymer. The molded saw segments then are affixed to the periphery of a saw blade.
European Patent No. 794,850 B1 describes cutting segments manufactured from superabrasive particles molded with a thermoplastic material wherein the superabrasive particles are oriented in a chosen direction and there is porosity in the molded segments.
U.S. Pat. Nos. 4,054,425 and 4,088,729 describe molding a hub into a phenol-based thermoplastic resin-grinding wheel.
U.S. Pat. No. 3,960,516 describes manufacturing a grinding cup wherein the supporting part is molded as a part of the grinding cup to ensure a secure attachment.
There is a need for curable, abrasive-filled resin compositions that allow fast preparation of cutting and grinding tools having improved wear characteristics.
SUMMARY OF INVENTION
Disclosed herein are several embodiments of a resin composition, its reaction product, a method for its preparation, and articles derived from it.
In one embodiment, a curable resin composition comprises a poly(arylene ether), an acryloyl monomer, an allylic monomer, and an abrasive filler.
In another embodiment, a cured resin composition comprises the reaction product of a poly(arylene ether), an acryloyl monomer, an allylic monomer, and an abrasive filler.
Yet another embodiment is a method of preparing the curable resin composition.
Still other embodiments are articles comprising the cured resin composition and methods for their preparation.
DETAILED DESCRIPTION
A curable resin composition comprises a poly(arylene ether), an acryloyl monomer, an allylic monomer, and an abrasive filler.
The composition may comprise any poly(arylene ether). The term poly(arylene ether) includes polyphenylene ether (PPE) and poly(arylene ether) copolymers; graft copolymers; poly(arylene ether) ether ionomers; and block copolymers of alkenyl aromatic compounds, vinyl aromatic compounds, and poly(arylene ether), and the like; and combinations comprising at least one of the foregoing; and the like. Poly(arylene ether)s are known polymers comprising a plurality of structural units of the formula:
wherein for each structural unit, each Q
1
is independently halogen, primary or secondary C
1
-C
12
alkyl, phenyl, C
1
-C
12
haloalkyl, C
1
-C
12
aminoalkyl, C
1
-C
12
hydrocarbonoxy, or C
2
-C
12
halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms; and each Q
2
is independently hydrogen, halogen, primary or secondary C
1
-C
12
alkyl, phenyl, C
1
-C
12
haloalkyl, C
1
-C
12
aminoalkyl, C
1
-C
12
hydrocarbonoxy, or C
2
-C
12
halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms. Preferably, each Q
1
is independently C
1
-C
12
alkyl or phenyl, especially C
1-4
alkyl, and each Q
2
is independently hydrogen or methyl.
Both homopolymer and copolymer poly(arylene ether)s are included. In one embodiment, the poly(arylene ether) is a homopolyrner comprising 2,6-dimethyl-1,4-phenylene ether units. Suitable copolymers include random copolymers comprising, for example, such units in combination with 2,3,6-trimethyl-1,4-phenylene ether units or copolymers derived from copolymerization of 2,6-dimethylphenol with 2,3,6-trimethylphenol. Also included are poly(arylene ether)s containing moieties prepared by grafting vinyl monomers or polymers such as polystyrenes, as well as coupled poly (arylene ether) in which coupling agents such as low molecular weight polycarbonates, quinones, heterocycles and formals undergo reaction with the hydroxy groups of two poly(arylene ether) chains to produce a higher molecular weight polymer. Poly(arylene ether)s further include combinations of any of the above.
The poly(arylene ether)s are typically prepared by the oxidative coupling of at least one monohydroxyaromatic compound such as 2,6-xylenol or 2,3,6-trimethylphenol. Catalyst systems are generally employed for such coupling; they typically contain at least one heavy metal compound such as a copper, manganese or cobalt compound, usually in combination with various other materials. Suitable methods for the preparation and isolation of poly(arylene ether)s are disclosed in, for example. U.S. Pat. No. 3,219,625 to Blanchard et al., U.S. Pat. No. 3,306,875 to Hay, U.S. Pat. No. 4,028,341 to Hay, U.S. Pat. No. 4,092,294 to Bennett, Jr. et al., U.S. Pat. No. 4,440,923 to Bartmann et al., and U.S. Pat. No. 5,922,815 to Aycock et al.
In one embodiment, the composition comprises a poly(arylene ether) having less than 500 parts per million (ppm) of free hydroxyl groups. In other words, the poly (arylene ether) contains less than 500 micrograms of hydroxyl groups (as —OH) per gram of poly(arylene ether). The poly(arylene ether) preferably comprises less than 300 ppm of free hydroxyl groups, more preferably less than 100 ppm of free hydroxyl groups.
In one embodiment, the composition comprises a capped poly(arylene ether), which is defined herein as a poly(arylene ether) in which at least 50%, preferably at least 75%, more preferably at least 90%, yet more preferably at least 95%, even more preferably at least 99%, of the free hydroxyl groups present in the corresponding uncapped poly(arylene ether) have been removed by reaction with a capping agent.
The capped poly(arylene ether) may be represented by the structure Q-U-K)
Y
wherein Q is the residuum of a monohydric, dihydric, or polyhydric phenol, preferably the residuum of a monohydric or dihydric phenol, more preferably the residuum of a monohydric phenol; y is 1 to 100; J comprises recurring units having the structure
wherein m is 1 to about 200, preferably 2 to about 200, and R
1
-R
4
are each independently hydrogen, halogen, primary or secondary C
1
-C
12
alkyl, C
2
-C
12
alkenyl, C
2
-C
12
alkynyl, C
1
-C
12
aminoalkyl, C
1
-C
12
hydroxyalkyl, phenyl, C
1-C
12
haloalkyl, C
1
-C
12
aminoalkyl, C
1
-C
12
hydrocarbonoxy, C
2
-C
12
halohydrocarbonoxy wherein at least two carbon atoms separate the halogen and oxygen atoms, or the like; and K is a capping group produced by reaction of the phenolic hydroxyl groups on the poly(arylene ether) with a capping reagent. The resulting capping group may be
wherein R
5
is C
1
-C
12
alky; R
6
-R
8
are each independently hydrogen, C
1
-C
12
alkyl, C
2
-C
12
alkenyl, C
6
-C
18
aryl, C
7
-C
18
mixed (alkyl-aryl), C
2
-C
12
alkoxycarbonyl, C
7
-C
18
Guo Hua
Teutsch Erich Otto
Webb Steven William
Yeager Gary William
Zarnoch Kenneth Paul
General Electric Company
McClendon Sanza
Sergent Rabon
LandOfFree
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