Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
2000-07-26
2003-03-11
Metzmaier, Daniel S. (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C524S862000, C525S100000, C525S106000, C525S478000, C525S479000, C523S340000
Reexamination Certificate
active
06531542
ABSTRACT:
CROSS-REFERENCE TO RELATED APPLICATIONS
Not applicable.
STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT
Not applicable.
REFERENCE TO A MICROFICHE APPENDIX
Not applicable.
FIELD OF THE INVENTION
This invention is directed to crosslinked organic particles and suspensions thereof, and to methods for preparing the crosslinked organic particles and their suspensions. More particularly, this invention relates to spherical crosslinked organic particles that are highly dispersible in thermoplastic resins, thermosetting resins, paints, coatings, cosmetics, rubbers, and toners and carriers employed in electrostatic development. The invention additionally relates to very efficient methods for preparing crosslinked organic particles. Crosslinked organic particle suspensions have excellent handling properties and are highly blendable with other components. The invention also relates to very efficient methods for preparing such suspensions.
BACKGROUND OF THE INVENTION
Non-thermally-softenable, solvent-insoluble crosslinked organic particles have an excellent resistance to heat, cold, and weathering, and excellent electrical properties, and are used as blocking inhibitors, cracking inhibitors, flatting agents, tactile sensation improvers, and lubricants for thermoplastic resins, thermosetting resins, paints, coatings, films, cosmetics, rubbers, and toners and carriers employed in electrostatic development. These crosslinked organic particles can be produced by (i) grinding or crushing a crosslinked organic material which produces irregularly shaped crosslinked organic particles; by (ii) producing solvent-insoluble crosslinked organic particles by dispersing a vinyl monomer and a compound bearing a plurality of unsaturated groups in a medium, and then inducing crosslinking by polymerization; and (iii) by dispersing epoxy resin in a medium and then crosslinking it using a curing agent to produce crosslinked organic particles.
However, such crosslinked organic particles suffer from poor dispersibility when blended into thermoplastic resins, thermosetting resins, paints, coatings, cosmetics, rubbers, and toners and carriers employed in electrostatic development.
BRIEF SUMMARY OF THE INVENTION
It is therefore an object of the invention to provide spherical crosslinked organic particles that are highly dispersible in thermoplastic resins, thermosetting resins, paints, coatings, cosmetics, rubbers, and toners and carriers employed in electrostatic development. Another object is to provide highly efficient methods for preparing crosslinked organic particles. An additional object is to provide crosslinked organic particle suspensions that have excellent handling properties and are highly blendable with other components. Yet another object is to provide highly efficient methods for preparing such suspensions.
These and other features of the invention will become apparent from a consideration of the detailed description.
BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING
Not applicable.
DETAILED DESCRIPTION OF THE INVENTION
Crosslinked organic particles according to the invention are spherical. They have an average particle size of 0.1 to 500 &mgr;m and are afforded by an hydrosilylation-induced crosslinking of a fluid composition comprising:
(A) an organic compound that contains at least 2 aliphatically unsaturated bonds in each molecule,
(B) a silicon-containing organic compound that has at least 2 silicon-bonded hydrogen atoms in each molecule, and
(C) a catalyst for the hydrosilylation reaction.
Crosslinked organic particle suspensions of the invention contain water, an emulsifying agent, the crosslinked organic particles, and the particles are dispersed in the water.
One method for preparing the crosslinked organic particles is by emulsifying a fluid composition comprising:
(A) an organic compound that contains at least 2 aliphatically unsaturated bonds in each molecule,
(B) a silicon-containing organic compound that has at least 2 silicon-bonded hydrogen atoms in each molecule, and
(C) a catalyst for the hydrosilylation reaction,
in water using an emulsifying agent, crosslinking the fluid composition by carrying out hydrosilylation, and thereafter removing the water.
Another method for preparing crosslinked organic particles comprises emulsifying a fluid composition of components (A) and (B) in water using an emulsifying agent, thereafter adding component (C), then crosslinking the composition by carrying out hydrosilylation, and finally removing the water.
One method for preparing crosslinked organic particle suspensions according to the invention is by emulsifying a fluid composition comprising:
(A) an organic compound that contains at least 2 aliphatically unsaturated bonds in each molecule,
(B) a silicon-containing organic compound that has at least 2 silicon-bonded hydrogen atoms in each molecule, and
(C) a catalyst for the hydrosilylation reaction,
in water using an emulsifying agent, and crosslinking the fluid composition by carying out hydrosilylation.
Another method for preparing crosslinked organic particle suspensions of the invention is by emulsifying a fluid composition of components (A) and (B) in water using an emulsifying agent, thereafter adding component (C), and then crosslinking the composition by carrying out hydrosilylation.
Crosslinked organic particles according to the invention are spherically-shaped crosslinked organic particles, and they are provided by an hydrosilylation-induced crosslinking of a fluid composition comprising components (A) through (C) described above. These particles should have an average particle size in the range from 0.1 to 500 &mgr;m, and preferably have an average particle size in the range from 0.1 to 200 &mgr;m. It is quite difficult to prepare crosslinked organic particles with an average particle size below the lower limit of the given range. Crosslinked organic particles with an average particle size exceeding the upper limit of the given range exhibit an increasingly impaired dispersibility when blended into organic resins, paints, coatings, and cosmetics.
Organic compound (A) contains at least 2 aliphatically unsaturated bonds in each molecule. The aliphatically unsaturated group in (A) can be a group present in a molecular chain terminal position, or it can be present in a pendant position on the molecular chain. It can be alkenyl such as vinyl, allyl, butenyl, and pentenyl; alkynyl such as ethynyl; or a cyclic unsaturated group such as the norbornene group or dicyclopentadienyl. The aliphatically unsaturated group can also be a group within the molecular chain, in which case it can be an enylene group like vinylene or propenylene. Groups present in a terminal or pendant position on the molecular chain such as vinyl and allyl are preferred for the aliphatically unsaturated group in (A). The state of (A) is not critical, and component (A) can be a solid or a liquid, with a liquid being preferred. When component (A) is a solid, it will be necessary to preliminarily dissolve it in component (B) when such dissolution is possible, or component (A) would have to be dissolved in an organic solvent. While the molecular weight of component (A) is not critical, its average molecular weight is preferably in the range from 50 to 50,000.
Component (A) can be exemplified by dienes such as pentadiene, hexadiene, heptadiene, octadiene, nonadiene, cyclopentadiene, and cyclooctadiene; aromatic dienes such as divinylbenzene; ethers such as diallyl ether, triethylene glycol divinyl ether, cyclohexane dimethanol divinyl ether, and 1,2-divinyl glycol; diene esters such as diallyl isophthalate, diallyl phthalate, diallyl terephthalate, diallyl maleate, and triallyl trimellitate; oligomers from polymerization of any of the preceding; olefin oligomers that contain at least 2 aliphatically unsaturated bond-containing groups in each molecule, produced by polymerization of an olefin such as ethylene, propylene, butene, isobutene, pentene, or hexene; oligomers from polymerization of an alkenyl-functional acrylic monomer such as allyl (meth)acrylat
Kobayashi Kazuo
Morita Yoshitsugu
Tachibana Ryuji
Brown Catherine U.
De Cesare Jim L.
Dow Corning Toray Silicone Company, Ltd.
Metzmaier Daniel S.
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