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
2002-11-05
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...
C525S100000, C525S478000, C528S015000, C528S025000
Reexamination Certificate
active
06476123
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 relates to crosslinked organic particles and suspensions thereof, and to methods for preparing crosslinked organic particles and their suspensions. More particularly, the invention relates to crosslinked organic particles that exhibit a very good affinity for organic oils such as mineral oils and synthetic oils, and that also exhibit suitable affinity for silicone oils. The invention additionally relates to very efficient methods for preparing crosslinked organic particles. Further, the invention relates to crosslinked organic particle suspensions that have excellent handling properties, and which are highly blendable with other components. The invention also relates to very efficient methods for preparing the suspensions.
BACKGROUND OF THE INVENTION
Silicone rubber particles have excellent resistance to heat, cold, and weathering, and have excellent electrical properties. As a consequence, they are useful as impact resistance improvers, flexibilizers, cracking inhibitors, flatting agents, softeners, tactile sensation improvers, oil absorbents, and lubricants for thermoplastic resins, thermosetting resins, paints, coatings, cosmetics, rubbers, and toners and carriers for electrostatic development.
However, while silicone rubber particles have a very good affinity for silicone oils, they suffer from a poor affinity for organic oils such as mineral oils and synthetic oils.
To address such problems, Japanese Laid Open (Kokai or Unexamined) Patent Application Number Hei 9-3408 (3,408/1997) discloses silicone rubber particles that contain C
5
to C
30
alkyl groups bonded to the silicon therein. These silicone rubber particles nevertheless remain a problem because their affinity for organic oils does not reach an acceptable level, yet their affinity for silicone oils is still high.
BRIEF SUMMARY OF THE INVENTION
It is an object of the invention, therefore, to provide crosslinked organic particles that exhibit a very good affinity for organic oils such as mineral oils and synthetic oils, and that also exhibit a suitable affinity for silicone oils.
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 which 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 have an average particle size of 0.1 to 500 &mgr;m, and are provided by the hydrosilylation-induced crosslinking of a fluid composition comprising (A) an organic compound that has at least 2 aliphatically unsaturated bonds in each molecule, (B) an organopolysiloxane that has at least 1 alkenyl group in each molecule, (C) a silicon-containing organic compound that has at least 2 silicon-bonded hydrogen atoms in each molecule, and (D) a catalyst of the hydrosilylation reaction.
Crosslinked organic particle containing suspensions of the invention contain water, an emulsifying agent, crosslinked organic particles, and wherein the particles are dispersed in water.
One method for preparing crosslinked organic particles is to emulsify a fluid composition comprising (A) an organic compound that has at least 2 aliphatically unsaturated bonds in each molecule, (B) an organopolysiloxane that has at least 1 alkenyl group in each molecule, (C) a silicon-containing organic compound that has at least 2 silicon-bonded hydrogen atoms in each molecule, and (D) a catalyst of the hydrosilylation reaction, in water using an emulsifying agent, crosslinking the fluid composition by carrying out an hydrosilylation reaction, and thereafter removing the water.
Another method for preparing crosslinked organic particles is to emulsify a fluid composition comprising components (A), (B), and (C), in water using an emulsifying agent, thereafter adding component (D), then crosslinking the composition by carrying out hydrosilylation, and finally removing water.
One method for preparing suspensions of crosslinked organic particles according to the invention is by emulsifying a fluid composition comprising (A) an organic compound that has at least 2 aliphatically unsaturated bonds in each molecule, (B) an organopolysiloxane that has at least 1 alkenyl group in each molecule, (C) a silicon-containing organic compound that has at least 2 silicon-bonded hydrogen atoms in each molecule, and (D) a catalyst for the hydrosilylation reaction, in water using an emulsifying agent, and crosslinking the fluid composition by carrying out the hydrosilylation reaction.
Another method for preparing suspensions of crosslinked organic particles is by emulsifying a fluid composition comprising components (A), (B), and (C), in water using an emulsifying agent, thereafter adding component (D), and then crosslinking the composition by carrying out hydrosilylation.
Crosslinked organic particles of the invention are crosslinked organic particles provided as a result of an hydrosilylation-induced crosslinking of the fluid composition of components (A) through (D) described above. These particles should have an average particle size in the range from 0.1 to 500 &mgr;m, and preferably they 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. The shape of the crosslinked organic particles can be spherical, spindle-shaped, plate-like, disk-like, or irregular, with a spherical shape being preferred. The crosslinked organic particles can be elastomeric in form such as a soft gel or rubber, or they can be a hard resin. Elastomers such as gels and rubbers are preferred, and rubbers are particularly preferred.
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 in a pendant position on the molecular chain. It can be an alkenyl group such as vinyl, allyl, butenyl, and pentenyl; an alkynyl group such as ethynyl; or a cyclic unsaturated group such as the norbornene group or dicyclopentadienyl. The aliphatically unsaturated group can also be within the molecular chain, in which case, it would constitute an enylene group such as vinylene or propenylene. Groups present in the terminal or pendant position on the molecular chain such as vinyl and allyl are preferred, however.
Component (A) can be a solid or liquid, but liquids are preferred. When component (A) is a solid, it is necessary to preliminarily dissolve it in component (B) or (C), or component (A) can 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-divinylglycol; diene esters such as diallyl isophthalate, diallyl phthalate, diallyl terephthalate, diallyl maleate, and triallyl trimellitate; oligomers from polymerization of any of the former; olefin oligomers containing at least 2 aliphatical
Kobayashi Kazuo
Morita Yoshitsugu
Tachibana Ryuji
De Cesare Jim L.
Dow Corning Toray Silicone Co. Ltd.
Metzmaier Daniel S.
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