- Method for synthesizing alkyl (meth) acrylate
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The invention discloses a synthesis method of alkyl (meth) acrylate, and belongs to the field of organic chemical synthesis. The synthesis method of the present invention employs a heterogeneous solid acid catalyst. The polymerization inhibitor and (meth) acrylic acid were put into the reaction kettle and heated to 50 - 90 °C, and an epoxide was introduced into the reaction kettle for reaction. The reaction solution is filtered to remove the homogeneous solid acid catalyst and the rectification to obtain the target product. The synthesis method not only can improve the selectivity of a target product (methyl) acrylic acid alkyl ester, but also can effectively inhibit the generation of high-boiling-point double esters of by-products generated by the addition of bis (methyl) acrylic acid.
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Paragraph 0032-0073; 0115-0134
(2021/12/08)
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- Intermediate substance with acid degradation function, preparation method of same, and polymerizable monomer prepared from intermediate substance
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The invention discloses an intermediate substance with an acid degradation function and a preparation method of same; whereinthe preparation method of the intermediate substance comprises the following steps: dissolving 2-nitrobenzaldehyde in a proper amount of dichloromethane, if the reaction substance is cinnamyl aldehyde, mixing the substance with trimethyl orthoformate without the help of a dichloromethane solvent with hafnium trifluoromethanesulfonate as a catalyst; then under the condition of room temperature, performing magnetic stirring to obtain the target substance in a very short time. According to the invention, the defects of time consumption, energy consumption, solvent consumption and the like caused by adopting p-toluenesulfonic acid as a catalyst for preparing the substance traditionally are avoided, and the prepared substance has an acid degradation function. Corresponding 2-nitrobenzaldehyde or cinnamyl aldehyde can be obtained through acid degradation, and in addition, the intermediate substance provides convenience for subsequent preparation of polymerizable monomers with an acid degradation function.
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Paragraph 0062; 0065
(2021/11/27)
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- Acrylate monomer having hydrophilic end group and a method for preparing the same
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More particularly, the present invention relates to an acrylate monomer having a high-purity hydrophilic terminal group which does not contain unreacted 1 water or undesirable by-products, and a method for producing the acrylate monomer. These acrylate monomers are substantially free of polymerization inhibitors. Chemical Formula 1. In Chemical Formula 1, R. 1 Chem. R. 2 Chem. R. 3 May be H, or linear, branched or cyclic C, independently of each other. 1 -C12 alkyl group. R4 Is linear, branched or cyclic C. 1 -C12 alkyl Or C1 -C12 It is alkoxy group, wherein alkyl group carbon atoms can be unsubstituted or substituted with oxygen atoms, n Is an integer selected from 1 and 10.
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Paragraph 0116-0118
(2021/11/02)
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- Technology for preparing high-purity 2-hydroxyethyl acrylate
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The invention discloses a technology for preparing high-purity 2-hydroxyethyl acrylate and relates to the field of 2-hydroxyethyl acrylate preparation technologies. The technology has the advantages that a rectification process is added during purification, a polymerization inhibitor is supplemented through spraying during phase transformation in the rectification process, and the vacuum degree and the operating temperature of a tower top are controlled to eradicate flash polymerization of the 2-hydroxyethyl acrylate in a rectifying tower, so that operation stability is achieved, polymerization can be prevented effectively, the product quality is improved, and the purity of the 2-hydroxyethyl acrylate is enhanced.
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Paragraph 0030; 0031
(2017/07/01)
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- A method for synthesis of hea
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The invention discloses a synthesis method of hydroxyethyl acrylate, which comprises the following steps of: adding acrylic acid into a reaction kettle, and then adding into a magnetic zeolite molecular sieve; stirring uniformly, and then adding epoxypropane; heating the reaction kettle to 60-65 DEG C, and reacting for 2-3 hours; and distilling to obtain the hydroxyethyl acrylate. According to the synthesis method disclosed by the invention, by adopting the magnetic zeolite molecular sieve as a catalyst, a polymerization inhibitor is not required, thus the separation and purification of products are facilitated; and moreover, the yield of the hydroxyethyl acrylate can exceed 97%, the catalyst can be recycled, and the synthesis cost is reduced.
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Paragraph 0018; 0019
(2017/03/08)
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- Preparation technique of high-purity hydroxyethyl acrylate
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The invention provides a preparation technique of high-purity hydroxyethyl acrylate. A rectification process is added in a purification process; a polymerization inhibitor is replenished through a spraying way in a phase transformation process of the rectification process; meanwhile, the vacuum degree and the working temperature of a tower top are controlled; the flash polymerization, in a rectifying tower, of hydroxyethyl acrylate is avoided, so as to achieve the purposes of being stable in operation, being capable of effectively preventing polymerization and improving product quality, thereby improving the purity of a hydroxyethyl acrylate product.
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Paragraph 0028-0031; 0035; 0038; 0041; 0044
(2018/02/04)
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- HYDROXYALKYL (METH)ACRYLATE AND METHOD FOR PRODUCING SAME
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The objective of the present invention is to provide a highly stable hydroxyalkyl (meth)acrylate. The hydroxyalkyl (meth) acrylate according to the present invention is characterized in that a contained amount of dialkylene glycol is not more than 0.05 mass%.
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Paragraph 0100; 0101; 0102; 0103
(2015/04/15)
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- HYDROXYALKYL ACRYLATE AND METHOD FOR PRODUCING SAME
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The hydroxyalkyl acrylate according to the present invention is characterized in that a content amount of an ester generated from acrylic acid dimer and an alkylene oxide is not more than 0.10 mass%. The method for producing a hydroxyalkyl acrylate according to the present invention is characterized in comprising the step of reacting acrylic acid with an alkylene oxide in the presence of a catalyst, wherein a content amount of acrylic acid dimer in the raw material acrylic acid is not more than 3.00 mass%.
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Paragraph 0120-0123
(2015/08/06)
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- New monomers for fullerene-containing polymers
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By reaction of 2-(acryloyloxyethyl) and (undecen-10-en-1-yl) methylmalonates with fullerene C60 in the system toluene-CBr 4-DBU, and also by reaction of 2-(2,2-dichloroacetoxy)ethyl acrylate with C60 in the system toluene-DBU the corresponding products of fullerene monocyclopropanation were synthesized.
- Torosyan,Biglova, Yu. N.,Mikheev,Gimalova,Mustafin,Miftakhov
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p. 179 - 182
(2014/04/17)
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- Antifouling and biodegradable poly(N-hydroxyethyl acrylamide) (polyHEAA)-based nanogels
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We synthesize and characterize two types of poly(N-hydroxyethyl acrylamide) (polyHEAA)-based nanogels: antifouling poly(2-(methacryloyloxy) ethyl trimethyl ammonium-g-N-hydroxyethyl acrylamide) (polyTM-g-HEAA) by a new two-step polymerization method of inverse microemulsion ATRP and surface-initiated atom transfer radical polymerization (SI-ATRP), and pH-responsive biodegradable polyHEAA nanogels by the inverse microemulsion free radical polymerization method. PolyTM-g-HEAA nanogels with a core-shell structure by grafting antifouling polyHEAA onto the cationic polyTM core are tested for their antifouling property and stability in fetal bovine serum (FBS) and nanogels-induced cell toxicity. Results show that with the antifouling protection of polyHEAA, polyTM-g-HEAA nanogels significantly improve their long-term stability in FBS up to 7 days by preventing nonspecific protein adsorption, and they also improve cell viability to ~94% and exhibit almost neglectable cell toxicity. Further, polyHEAA nanogels cross-linked with acid-liable ethylidenebis(oxy-2,1-ethanediyl) ester (EOE) are synthesized, which exhibit both biodegradation and control-release of encapsulated rhodamine 6G (R6G) at acid conditions. Conjugation of transferrin ligands onto R6G-loaded polyHEAA nanogels further enhances cellular uptake efficiency and intracellular drug release for targeting drug delivery. This work demonstrates that polyHEAA-based nanogels with easy synthesis, excellent antifouling property and stability, biodegradability, low toxicity, and pH-responsive intracellular drug release are highly promising for targeted drug delivery systems for biomedical applications. The Royal Society of Chemistry 2013.
- Zhao, Chao,Patel, Kunal,Aichinger, Lindsay Marie,Liu, Zhaoqian,Hu, Rundong,Chen, Hong,Li, Xiaosi,Li, Lingyan,Zhang, Ge,Chang, Yung,Zheng, Jie
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p. 19991 - 20000
(2013/11/06)
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- Single cyclized molecule structures from RAFT homopolymerization of multi-vinyl monomers
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We explore a kinetically controlled strategy to suppress the gelation in the homopolymerization of multi-vinyl monomers (MVMs) via RAFT polymerization. We report the generation of 3D single cyclized polymer structures from the RAFT process, which significantly contradicts the classic F-S theory. This approach enables synthesis of a new generation of nanosize macromolecular architectures. The Royal Society of Chemistry 2012.
- Zheng, Yu,Newland, Ben,Tai, Hongyun,Pandit, Abhay,Wang, Wenxin
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body text
p. 3085 - 3087
(2012/04/17)
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- Incorporation and controlled release of silyl ether prodrugs from PRINT nanoparticles
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Asymmetric bifunctional silyl ether (ABS) prodrugs of chemotherapeutics were synthesized and incorporated within 200 nm × 200 nm particles. ABS prodrugs of gemcitabine were selected as model compounds because of the difficulty to encapsulate a water-soluble drug within a hydrogel. The resulting drug delivery systems were degraded under acidic conditions and were found to release only the parent or active drug. Furthermore, changing the steric bulk of the alkyl substituents on the silicon atom could regulate the rate of drug release and, therefore, the intracellular toxicity of the gemcitabine-loaded particles. This yielded a family of novel nanoparticles that could be tuned to release drug over the course of hours, days, or months.
- Parrott, Matthew C.,Finniss, Mathew,Luft, J. Chris,Pandya, Ashish,Gullapalli, Anuradha,Napier, Mary E.,Desimone, Joseph M.
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supporting information; experimental part
p. 7978 - 7982
(2012/06/18)
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- Hydroxy functional acrylate and methacrylate monomers prepared via lipase-catalyzed transacylation reactions
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Candida antarctica lipase B (CAL-B, Novozyme 435) catalyzes the transacylation of methyl acrylate and methyl methacrylate with diols and triols in 2-methyl-2-butanol at 50 °C. Under the experimental conditions, up to 70 mol% of the acyl donor methyl acrylate was converted. Methyl methacrylate is the less efficient acyl donor (up to 60 mol%) due to the higher sterical hindrance in the enzymatic transacylation. Under the reaction conditions high yields of the mono-acylated products are obtained, which contain minor amounts of bis(meth)acrylates. In addition it was observed that Novozyme 435 catalyzes regioselectively the acylation of the primary hydroxyl groups. In comparison with the chemical catalyzed route no selectivity was observed for unsubstituted diols. For substituted diols more mono-acylated product was formed in the lipase-catalyzed reaction than in the chemical catalyzed reaction.
- Popescu, Dragos,Hoogenboom, Richard,Keul, Helmut,Moeller, Martin
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experimental part
p. 80 - 89
(2010/08/20)
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- Process for the production of hydroxyalkyl (meth)acrylates
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The present invention relates to a process for producing high purity hydroxyalkyl (meth)acrylates. Specifically, the present invention relates to an improved process which can commercially and advantageously yield high purity hydroxyalkyl (meth)acrylates from (meth)acrylic acid and alkylene oxides.
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Page/Page column 2-3
(2009/09/05)
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- A process for the production of hydroxyalkyl (meth)acrylates
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The present invention relates to a process for producing high purity hydroxyalkyl (meth)acrylates. Specifically, the present invention relates to an improved process which can commercially and advantageously yield high purity hydroxyalkyl (meth)acrylates from (meth)acrylic acid and alkylene oxides.
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Page/Page column 3-4
(2008/12/07)
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- PROCESSES FOR PRODUCING HYDROXYALKYL (METH)ACRYLATE
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Processes for producing a hydroxyalkyl (meth)acrylate which comprise reacting (meth)acrylic acid with an alkylene oxide in the presence of a catalyst. A first process is characterized in that the amount of the acid ingredient is kept, on calculation, at 0.010 or more in terms of molar ratio to the catalyst present in the liquid reaction mixture and that the liquid reaction mixture from which the hydroxyalkyl (meth)acrylate has been distilled off is used in the subsequent reaction. A second process is characterized in that a dialkylene glycol mono(meth)acrylate is supplied to the reaction system to cause the dialkylene glycol mono(meth)acrylate to coexist in the liquid reaction mixture.
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Page/Page column 24--27; 34-37
(2008/06/13)
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- Process for preserving resin catalyst for addition reaction of alkylene oxide and utilization of this process
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The present invention provides a process and its utilization in a process comprising the step of carrying out an addition reaction of an alkylene oxide to an addition-receiving substance in the presence of a resin catalyst, thereby producing the addition reaction product, when the resin catalyst as used for the reaction is persevered so as to recycle it after it is recovered, the unreacted alkylene oxide remaining in the resin catalyst can be prevented from polymerizing and solidifying during the preservation, and the resin catalyst accordingly can be preserved stably for a long time. The resin catalyst as recovered after it is used for the reaction may be preserved under any of the following conditions: 1) at a low temperature of not higher than 40° C.; 2) in the presence of a carboxylic acid; 3) in the presence of a liquid having an alkylene oxide concentration of not more than 2 weight %; and 4) in the coexistence of a carboxylic acid and a liquid having an alkylene oxide concentration of not more than 2 weight %. The present catalyst is recycled for the above addition reaction.
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Page/Page column 12-15
(2008/06/13)
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- METHOD FOR THE PRODUCTION OF HYDROXYALKYL CARBONIC ACID ESTERS
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The invention relates to a heterogeneously catalyzed method for producing hydroxyalkyl carbonic acid esters from carbonic acids and alkylene oxides and the use thereof.
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Page/Page column 19
(2008/06/13)
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- Production process for hydroxyalkyl (meth) acrylate
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There is disclosed a novel production process for a hydroxyalkyl (meth)acrylate in which: the diffusion of harmful substances due to disposal of catalysts can be reduced; and also the amount of the catalyst as used can be greatly saved in the entire production process. This production process comprises the step of carrying out a reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the production process being characterized by further comprising the step of recovering the catalyst as has been used for the reaction.
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- Production process for hydroxyalkyl (meth)acrylate
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The present invention provides a novel production process for a hydroxyalkyl (meth)acrylate, in which it is possible that: in a batch reaction system, the amount of the hydroxyalkyl (meth)acrylate (which is the objective product) as produced is kept nearly on the same level as conventional and further, at the same time, there is suppressed the side production of the alkylene oxide's diaddition product (dialkylene glycol mono(meth)acrylate) that lowers the purity of the product to thus give a bad influence upon its quality. The present invention production process comprises the step of carrying out a batch reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the production process being characterized by arranging that the reaction should be initiated in a state of a catalyst concentration of more than 1, wherein the catalyst concentration is defined as the amount of the catalyst as used relative to the integrated amount of the (meth)acrylic acid as supplied and is assumed to be 1 in terms of the amount of the entire catalyst to be used relative to the amount of the entire (meth)acrylic acid to be supplied.
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- Process for the conversion of aldehydes to esters
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A process for the conversion of aldehydes to esters, specifically acrolein or methacrolein to methyl acrylate or methyl methacrylate, respectively. Essentially in the absence of water, an aldehyde is contacted with an oxidizing agent to form an intermediate and then the intermediate is contacted with a diol or an alcohol to form an ester or diester. Preferably, the oxidizing agent is also a chlorinating agent. Specifically, acrolein or methacrolein is contacted with an oxidizing/chlorinating agent, such as t-butyl hypochlorite, and the chlorinated compound is contacted with an alcohol, such as methanol, to form methyl acrylate or methyl methacrylate, respectively. Generally, the order of addition is for the oxidizing agent to be added to the aldehyde, specifically for t-butyl hypochlorite to be added to acrolein or methacrolein, and for the diol or alcohol to be added to the intermediate, specifically for the methanol to be added to the reaction product of acrolein or methacrolein and t-butyl hypochlorite. The process of the present invention can be carried out in the absence or in the presence of solvent. Generally, better methyl acrylate or methyl methacrylate yields are obtained at lower reaction temperatures.
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Page/Page column 3-4
(2010/01/31)
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- Process for the preparation of hydroxyalkyl(meth)acrylate
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The present invention provides: a high-quality hydroxyalkyl (meth)acrylate of which the alkylene glycol di(meth)acrylate content and the acid component content are both low; and its novel production process. The hydroxyalkyl (meth)acrylate, which has a content, in terms of an alkylene glycol di(meth)acrylate as an impurity, of not more than 0.1 weight % and an acid component content of not more than 0.1 weight %, is obtained by a process comprising the step of carrying out a batch reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the process making an adjustment as to charging of both raw materials in such a manner that, for, of a time as needed for supplying both raw materials, a supplying time of not less than 40 % of a total supplying time when the raw materials as supplied have a temperature of not lower than 40 °C, the molar ratio of the integrated amount of the alkylene oxide to the integrated amount of the (meth)acrylic acid that have been added to a reactor by then can be more than 1.0.
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- Reshapable hair styling rinse composition comprising (meth)acrylic copolymers
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A reshapable hair styling composition comprising, optionally in a cosmetically acceptable vehicle, at least one (meth)acrylic copolymer, wherein the at least one (meth)acrylic copolymer comprises: (a) units derived from at least one monomer chosen from butyl (meth)acrylate monomers, (b) units derived from at least one monomer chosen from hydroxy alkyl (meth)acrylate monomers, and (c) optional units derived from at least one co-polymerizable monomer other than said (a) and (b) monomers, wherein said composition provides a reshapable effect and is a rinse composition.
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- Reshapable hair styling non-rinse composition comprising (meth)acrylic copolymers
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A reshapable hair styling composition comprising, optionally in a cosmetically acceptable vehicle, at least one (meth)acrylic copolymer, wherein the at least one (meth)acrylic copolymer comprises: (a) units derived from at least one monomer chosen from butyl (meth)acrylate monomers, (b) units derived from at least one monomer chosen from hydroxy alkyl (meth)acrylate monomers, and (c) optional units derived from at least one co-polymerizable monomer other than said (a) and (b) monomers, wherein said composition provides a reshapable effect and is a non-rinse composition.
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- Process for producing hydroxyalkyl (METH) acrylates
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In a process for producing hydroxyalkyl (meth)acrylates by the reaction of (meth)acrylic acid with an alkylene oxide, a thermally and chemically stable anion exchange resin is used as a catalyst, which resin contains a repeating unit represented by the following formula (1) as a component: wherein A is a straight chain alkylene group having 3 to 8 carbon atoms, each of R1, R2, and R3is a hydrocarbon group or an alkanol group having 1 to 4 carbon atoms, which may be substituted with a hydroxyl group, X?is a counter ion coordinated with an ammonium group, where the substituent A with the ammonium group may be substituted at any position of a benzene ring, and the benzene ring may be substituted with an alkyl group or a halogen atom. The process can economically efficiently produce hydroxyalkyl (meth)acrylates without disadvantages such as deterioration in properties of a distillation residue.
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Page column 8
(2008/06/13)
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- The 'Baylis - Hillman reaction' mechanism and applications revisited
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It is shown that reaction of aryl, benzyl, alkyl and functionalised alkyl acrylic esters with benzaldehyde, in the presence of 1,4-diazabicyclo[2.2.2] octane, strongly depends upon the electronic and steric effects of the ester part. This influence is also observed in condensation of furfuraldehyde. Moreover, for the first time, it is shown that the overall condensation is equilibrated.
- Fort, Yves,Berthe, Marie Christine,Caubere, Paul
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p. 6371 - 6384
(2007/10/02)
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- High solids acrylic coating systems
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High solids acrylic coating compositions are formulated by using as a reactive diluent, a low molecular weight hydroxyl-containing acrylic polymer. These polymers are prepared at about 15°-20° C. with anionic initiator concentrations greater than about 5 mole percent.
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- FIBROUS POLYMERIC COMPOSITES IMMOBILIZING GLUCOSE OXIDASE
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Fibrous polymeric composites immobilizing glucose oxidase have been prepared by the radiation polymerization of various glass-forming monomers at low temperatures.The radiation polymerization of the monomer solution containing the enzymes and fibrous material was studied as a function of the irradiation temperature, at which the polymerization rate and enzyme activity had optimum values.The nature of the monomer, monomer concentration and the thickness of the polymer matrix on the fibrous material was shown to affect the enzyme activity of the composites.
- Kumakura, M.,Kojima, T.,Kaetsu, I.
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- 4-Hydroxyphenylthio substituted stabilizers for polymers
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The title compounds correspond to the formula STR1 where n is 1 and are characterized in that at least one of A, X or Y contains a group of formula STR2 these compounds being useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.
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- Chromium salt catalysts
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This patent describes the catalytic promotion of the reaction of oxirane-containing compounds with carboxylic acid compounds at high, ambient, and low temperature. Specifically, this patent describes the method of reacting oxirane-containing compounds with carboxyl-containing compounds, preferably at temperatures at or around ambient, in the presence of active chromium III tricarboxylate salts which have unoccupied coordination sites. More specifically this patent describes the preparation of catalytically active chromium III-tricarboxylates from normally catalytically inactive chromium III tri-carboxylate hydrates. These compounds are powerful catalysts for the reactions of oxirane compounds with both organic carboxylic acids and cyclic primary imides.
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