41 |
Brominated and epoxidized flame retardants |
US12825591 |
2010-06-29 |
US08569424B2 |
2013-10-29 |
Erin B. Vogel; Shari L. Kram; Daniel J. Murray; Bruce A. King |
Brominated and epoxidized organic compounds are useful flame retardants for polymers such as polystyrene. The organic compounds contain both bromine and oxirane groups, and have molecular weights of at least 1500. The brominated and epoxidized organic compounds can be prepared by sequentially brominating and epoxiding (in either order) a starting compound that contains multiple non-conjugated carbon-carbon double bonds. |
42 |
Process for Brominating Butadiene Polymers Using Mixed Solvents |
US13817447 |
2011-09-19 |
US20130178589A1 |
2013-07-11 |
Bruce A. King; John W. Hull, JR. |
Butadiene polymers are brominated using a quaternary ammonium or quaternary phosphonium tribromide as the brominating agent. The bromination is performed in a solvent mixture than contains at least one polyhalogenated alkane and at least one monohalogenated alkane. The process proceeds easily under mild conditions and allows high conversions to be achieved easily. |
43 |
Process for Recovering Brominated Styrene-Butadiene from a Bromination Reaction Solution |
US13818859 |
2011-09-19 |
US20130178547A1 |
2013-07-11 |
John W. Hull, JR.; Bruce A. King, JR.; Shari L. Kram; Joseph J. Kiefer |
Brominated styrene-butadiene copolymers are recovered from solutions in a halogenated solvent by an anti-solvent precipitation process. The precipitation process is performed by adding the anti-solvent to the brominated styrene-butadiene copolymer solution. By performing the precipitation using this specific order of addition, a denser product is obtained that is easier to dry. The recovered product shows a reduced tendency to act as a nucleating agent when it is used as a flame retardant additive in an extrusion foaming process. |
44 |
Process for brominating unsaturated organic compounds using a quaternary phosphonium tribromide as the brominating agent |
US13057255 |
2009-08-13 |
US08372921B2 |
2013-02-12 |
John W. Hull, Jr. |
Compounds or polymers that contain carbon-carbon unsaturation are brominated using a quaternary phosphonium tribromide as the brominating agent. The bromination process proceeds easily under mild conditions. The process can be highly selective. When the substrate is a butadiene polymer or copolymer, the brominated product tends to have excellent thermal stability. |
45 |
Process for cleaner production of chlorinated rubber without using carbon tetrachloride and water |
US12992807 |
2008-06-24 |
US08268931B2 |
2012-09-18 |
Bolin Tong |
The present invention relates to a green technology to produce chlorinated rubber without using carbon tetrachloride and water by using 1,1,2-trichloroethane as the solvent and iodine as the catalyst. The natural rubber reacts with an excessive amount of gaseous chlorine at 60-100° C. for 3-8 hours and the product is then dried. The method of the present invention complies with the environmental requirements of “The Montreal Protocol on Substances that Deplete the Ozone Layer” by abandoning the usage of CCl4. It also complies with the relevant regulations regarding ship-shell paints. Moreover, it is easy to carry out and is suitable for industrialization. |
46 |
Process for brominating butadieneninyl aromatic copolymers |
US12375679 |
2007-08-14 |
US08202945B2 |
2012-06-19 |
Bruce A. King; David B. Gorman; John W. Hull, Jr.; Daniel J. Murray; Terry L. Gehrman |
Butadiene copolymers are brominated using certain quaternary ammonium tribromides as the brominating agent. The bromination process proceeds easily under mild conditions, and produces a brominated product that has excellent thermal stability. |
47 |
Method for producing modified conjugated diene based (co)polymer, modified conjugated diene based (co)polymer, and rubber composition |
US12532764 |
2008-03-21 |
US08178626B2 |
2012-05-15 |
Masahiro Shibata; Takaomi Matsumoto; Tamotsu Nagaoka; Takuo Sone; Toshihiro Tadaki |
The method for producing a modified conjugated diene based (co)polymer, according to the present invention comprises a step of reacting a conjugated diene based (co)polymer with a metal halide compound to obtain a modified conjugated diene based (co)polymer, the conjugated diene based (co)polymer having a weight-average molecular weight of 150,000 to 2,000,000 and being obtained by bonding, to a polymer having at least a conjugated diene unit, an alkoxysilyl group and an optionally protected primary amino group. The method can satisfactorily produce a conjugated diene based (co)polymer which has a high Mooney viscosity, excellent shape stability and good processability. |
48 |
PROCESS FOR BROMINATING UNSATURATED ORGANIC COMPOUNDS WITH REMOVAL OF QUATERNARY AMMONIUM OR QUATERNARY PHOSPHONIUM MONOCHLORIDES |
US13257999 |
2010-02-02 |
US20120016088A1 |
2012-01-19 |
David B. Gorman; Douglas C. Greminger; Ronald B. Leng |
Unsaturated organic compounds are brominated with a quaternary ammonium tribromide or a quaternary phosphonium tribromide, especially when the bromination is conducted in a chlorinated solvent. A quaternary ammonium or quaternary phosphonium monobromide salt is produced in the reaction, together with some amount of quaternary ammonium or quaternary phosphonium monochloride salt. The monochloride salt is converted to the corresponding quaternary ammonium monobromide salt by reacting it with a source of bromide ions. The monobromide salt is then reacted with bromine to regenerate the quaternary ammonium or phosphonium tribromide, which is recycled into the bromination reaction. This process reduces the amount of chlorine that is incorporated into the brominated product. |
49 |
Process for recovering brominated butadiene polymers from solution |
US12146636 |
2008-06-26 |
US08058389B2 |
2011-11-15 |
Ronald B. Leng; Avani M. Patel; Brian D. Scherzer; Derrick G. Wetters; Douglas C. Greminger |
Brominated polybutadiene polymers are recovered from a bromination reaction solution by forming the solution into droplets, thermally stripping the solvent from the droplets, and then washing the resulting particles. The washed particles are then recovered from the washing liquid. The droplets can be dispersed into a gaseous medium such as air and then transferred into a nonsolvent liquid for washing, or can be formed directly into the nonsolvent liquid. The process forms a particulate polymer material that is easily filterable and has low levels of volatile impurities and inorganic salts. Brominated polybutadiene polymers recovered in this manner are often very thermally stable. |
50 |
PROCESS FOR FORMING AND DEVOLATILIZING BROMINATED POLYBUTADIENE POLYMER PARTICLES |
US13057251 |
2009-08-18 |
US20110143030A1 |
2011-06-16 |
Douglas C. Greminger |
Brominated butadiene polymers are recovered from solution and formed into particles by spraying the solution onto a heated, mechanically agitated bed of seed particles. The droplets contact the seed particles in the bed and form a polymer layer on the outside of the seed particles, thereby enlarging them. The solvent is removed from the droplets after they make contact with seed particles in the bed. The process allows for the simultaneous removal of solvent and formation of somewhat large particles. The process forms at most small amounts of agglomerates and fines. |
51 |
PROCESS FOR BROMINATING BUTADIENE COPOLYMERS BY THE ADDITION OF WATER OR CERTAIN SOLVENTS |
US12866992 |
2009-02-25 |
US20110021715A1 |
2011-01-27 |
David Bruce Gorman |
Butadiene copolymers are brominated using certain quaternary ammonium tribromides as the brominating agent. The bromination process proceeds easily under mild conditions, and produces a brominated product that has excellent thermal stability. A quaternary ammonium monobromide salt is produced as a reaction by-product. A solvent for the monobromide salt is added to the reaction after 25-90% bromination of the aliphatic carbon-carbon double bonds. This provides for significantly shorter reaction times while providing a product with few impurities. |
52 |
METHOD FOR PRODUCING MODIFIED CONJUGATED DIENE BASED (CO)POLYMER, MODIFIED CONJUGATED DIENE BASED (CO)POLYMER, AND RUBBER COMPOSITION |
US12532764 |
2008-03-21 |
US20100152369A1 |
2010-06-17 |
Masahiro Shibata; Takaomi Matsumoto; Tamotsu Nagaoka; Takuo Sone; Toshihiro Tadaki |
The method for producing a modified conjugated diene based (co)polymer, according to the present invention comprises a step of reacting a conjugated diene based (co)polymer with a metal halide compound to obtain a modified conjugated diene based (co)polymer, the conjugated diene based (co)polymer having a weight-average molecular weight of 150,000 to 2,000,000 and being obtained by bonding, to a polymer having at least a conjugated diene unit, an alkoxysilyl group and an optionally protected primary amino group. The method can satisfactorily produce a conjugated diene based (co)polymer which has a high Mooney viscosity, excellent shape stability and good processability. |
53 |
Process for brominating butadiene/vinyl aromatic copolymers |
US12375679 |
2007-08-14 |
US20100004402A1 |
2010-01-07 |
Bruce A. King; David B. Gorman; John W. Hull, JR.; Terry L. Gehman |
Butadiene copolymers are brominated using certain quaternary ammonium tribromides as the brominating agent. The bromination process proceeds easily under mild conditions, and produces a brominated product that has excellent thermal stability. |
54 |
Materials comprising polydienes and hydrophilic polymers and related methods |
US12322205 |
2009-01-30 |
US20090306295A1 |
2009-12-10 |
Jimmy W. Mays; Suxiang Deng; Kenneth A. Mauritz; Mohammad K. Hassan; Samuel P. Gido |
Materials prepared from polydienes, such as poly(cyclohexadiene), and hydrophilic polymers, such as poly(alkylene oxide), are described. Methods of making the materials and their use in fuel cell membranes, batteries, breathable chemical-biological protective materials, and templates for sol-gel polymerization are also provided. The materials can be crosslinked and sulfonated, and can include copolymers and polymer blends. |
55 |
Photocurable acrylated chlorinated rubber coatings |
US08444534 |
1995-05-19 |
US06399673B1 |
2002-06-04 |
Shelby Freland Thames; Zhiqiang Alex He |
The invention relates to acrylated chlorinated rubber, a method for making acrylated chlorinated rubber comprising reacting chlorinated hydroxyrubber and acryloyl chloride with triethylamine as a catalyst, and photocurable rubber coatings comprising acrylated chlorinated rubber. |
56 |
Higher modulus compositions incorporating particulate rubber |
US609520 |
1996-03-01 |
US5693714A |
1997-12-02 |
Bernard D. Bauman; Mark A. Williams; Reza Bagheri |
Rubber particles, to be used as fillers or extenders for various composite polymer systems, are chlorinated by a gas-solid phase reaction with a chlorine-containing gas. A composite polymer containing the chlorinated rubber fillers or extenders exhibits a higher flexural modulus than if prepared using an unchlorinated rubber filler or extender. Chlorination of the rubber particles is carried out by contacting the finely divided rubber particles with a chlorine-containing gas comprising at least about 5 volume percent chlorine. Advantageously, the chlorine can be diluted with air, nitrogen or other essentially inert gases and may contain minor amounts of fluorine. Improved performance is obtained with nitrogen dilution of the chlorine gas over air dilution. Improved polymer composite systems having higher flexural modulus result from the use of the chlorinated rubber particles as fillers instead of unchlorinated rubber particles. |
57 |
Process for direct addition of acid to polymers |
US16552 |
1993-02-11 |
US5369188A |
1994-11-29 |
Young H. Kim |
A process comprising the direct addition of a halogenated carboxylic acid to an olefin-containing compound is disclosed, as well as the resulting adduct and saponified adduct. |
58 |
Halogenated polybutadiene series elastomers, method of producing the
same and rubber compositions for tire containing this elastomer |
US347082 |
1989-05-26 |
US5137981A |
1992-08-11 |
Tomoharu Yamada; Ryota Fujio |
A novel halogenated polybutadiene series elastomer is produced by reacting a polybutadiene series elastomer with a particular active halogen group-containing compound in the presence of a particular organic halogenating agent. The resulting halogenated polybutadiene series elastomer can be subjected to heat-resistant crosslinking with a particular polyvalent amine, and is suitable for the preparation of rubber compositions for tire requiring the heat resistance. |
59 |
Rubber composition for tread in high-speed running tires |
US545090 |
1990-06-28 |
US5132348A |
1992-07-21 |
Tadashi Saito; Joji Yatsunami; Ichiro Wada; Toshiki Takizawa |
A tread rubber composition for high-speed running tires comprises a particular halogenated modified styrene-butadiene copolymer having p-halomethylbenzoyl group as a starting rubber and contains particular amounts of carbon black, process oil and diamine, and has excellent heat resistance and wear resistance. |
60 |
Process for the manufacture of halogenated polymers |
US651621 |
1984-09-17 |
US4548995A |
1985-10-22 |
Ronald C. Kowalski; William M. Davis; Neil F. Newman; Z. Andrew Foroulis; Francis P. Baldwin |
In a process for the continuous halogenation of polymers by contacting polymer and halogenating agent in a continuous flow device in which means are provided for disengaging reaction by-products and unreacted halogenating agent from the reaction mixture, by deforming and disrupting the halogenated polymer surface and injecting an inert gas into the halogenated polymers immediately after reaction thereby neutralizing the product. In a preferred embodiment the process is carried out in an extruder-reactor and an optional, supplementary inert gas scrubbing zone is included. The process is amenable to saturated and unsaturated polymers. |