cas 1025-15-6, 1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione

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Selective and Efficient Syntheses of Perhydro-1,3,5-triazine-2,4,6-triones and Carbodiimides from Isocyanates Using ZP(MeNCH2CH2)3N Catalysts
With concentrations as low as 0.0033 mol percent ZP(MeNCH2CH2)3N (Z = lone pair, 1) isocyanates are catalytically trimerized to perhydro-1,3,5-triazine-2,4,6-triones (isocyanurates) at room temperature.This reaction proceeds readily in the presence or absence of solvent, and the catalyst can be recycled at least six times without detectable degradation.Though not as potent a catalyst as 1, the molecule in which Z = NPh (3) also facilitates this reaction, and evidence is adduced that the catalytically active species is the adduct 3*ArNCO (6).In contrast, Ch=P(MeNCH2CH2)3N (Ch = O, 4; Ch = S, 5) selectively catalyze the transformation of isocyanates to carbodiimides and do so more efficiently than their acyclic analogues O=P(NMe2)3 and (MeO)2P(S)Ph, respectively.The crystal structure of 4 is reported for the first time, and details of the crystal structure of I reported earlier by us in preliminary form are presented.Both structures support the hypothesis that P-Nax transannulation plays a lead role in the catalytic activities of 1 and 3 - 5.
Tang, Jiansheng,Mohan, Thyagarajan,Verkade, John G.
p. 4931 - 4938
(1994)
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Organocatalytic, rapid and facile cyclotrimerization of isocyanates using tetrabutylammonium phthalimide-N-oxyl and tetraethylammonium 2-(carbamoyl)benzoate under solvent-free conditions
Tetrabutylammonium phthalimide-N-oxyl and tetraethylammonium 2-(carbamoyl)benzoate were found to be effective and easily accessible organocatalysts for selective cylotrimerization of aryl and alkyl isocyanates under mild reaction conditions. The reaction proceeds smoothly using very low catalyst loadings of these metal-free organocatalysts (0.025 and 0.25 mol%, respectively) under solvent-free conditions at room temperature within a very short reaction time.
Dekamin, Mohammad G.,Varmira, Kambiz,Farahmand, Mehdi,Sagheb-Asl, Solmaz,Karimi, Zahra
p. 226 - 230
(2010)
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Amine-linked N-heterocyclic carbenes: The importance of an pendant free-amine auxiliary in assisting the catalytic reaction
We have successfully expanded the library of amino-NHCs with varying substituents on the amine group, leading to insight about the instability of NHCs arising from the intermolecular interaction of the dangling amine side-arm. However, the pendant amine plays an important role with respect to the catalytic process, resuscitating the catalytic activity of unsaturated NHC's through a synergistic effect invoked by the secondary amine. This proof of concept allows us to expand the spectrum of catalysis to C-C, as well as C-B bond formation. Copyright
Li, Chia-Yi,Kuo, Yi-Yin,Tsai, Jie-Hong,Yap, Glenn P. A.,Ong, Tiow-Gan
p. 1520 - 1524
(2011)
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Preparation process of triallyl isocyanurate (by machine translation)
The preparation process is characterized in that allyl alcohol is used as a raw material, allyl alcohol and p-toluenesulfonyl chloride are prepared into allyl tosylate through an acid binding agent; and the prepared allyl tosylate is reacted with sodium cyanate, a phase transfer catalyst and a polar solvent to obtain triallyl isocyanurate. To the preparation method, allyl alcohol is adopted as the raw material, atmospheric pollution is reduced, the reaction rate is higher, the yield of triallyl isocyanurate is improved, the environment is protected, and the energy-saving and consumption-reducing effect is remarkable. (by machine translation)
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Paragraph 0010; 0013-0030

(2020/07/02)

Highly efficient cyclotrimerization of isocyanates using N-heterocyclic olefins under bulk conditions
With a catalyst loading as low as 0.005%, high to excellent yields of isocyanurates could be achieved from N-heterocyclic olefin mediated organocatalytic cyclotrimerization of a wide range of isocyanates under bulk conditions. Experimental details coupled with structural characterization of the key intermediates led to comprehensive mechanistic studies of cyclotrimerization.
Li, Chengkai,Zhao, Wuchao,He, Jianghua,Zhang, Yuetao
supporting information
p. 12563 - 12566
(2019/10/28)

Aluminium-catalysed isocyanate trimerization, enhanced by exploiting a dynamic coordination sphere
Main-group metals are inherently labile, hindering their use in catalysis. We exploit this lability in the synthesis of isocyanurates. For the first time we report a highly active catalyst that trimerizes alkyl, allyl and aryl isocyanates, and di-isocyanates, with low catalyst loadings under mild conditions, using a hemi-labile aluminium-pyridyl-bis(iminophenolate) complex.
Bahili, Mohammed A.,Stokes, Emily C.,Amesbury, Robert C.,Ould, Darren M. C.,Christo, Bashar,Horne, Rhian J.,Kariuki, Benson M.,Stewart, Jack A.,Taylor, Rebekah L.,Williams, P. Andrew,Jones, Matthew D.,Harris, Kenneth D. M.,Ward, Benjamin D.
supporting information
p. 7679 - 7682
(2019/07/08)

Method for synthesizing highly pure cross-linking agent triallyl isocyanurate
The invention discloses a method for synthesizing highly pure cross-linking agent triallyl isocyanurate. The highly pure triallyl isocyanurate is synthesized from bromopropene, cyanuric acid, a phasetransfer catalyst and a composite catalyst in a polar organic solvent, produced tail gas hydrogen bromide is fully absorbed by circulating water of asecondary graphite parallel flow falling film absorption tower, and is used into prepare certain-concentration hydrobromic acid for sale; the above synthesis reaction is carried out in the organic medium instead of a strong alkaline aqueous solution,so generation of a large amount of wastewater containing organic matters and salts is avoided, and treatment and processing of high-concentration wastewater and waste residues are avoided; and the finally obtained reaction solution is desolvated to obtain the highly pure TAIC with a content of 99.0% or above.
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Paragraph 0028-0030

(2019/01/05)

Production of [...]
A method for producing alkenyl isocyanurate by reacting cyanuric acid or isocyanuric acid with an unsaturated alcohol while in the presence of a palladium-loaded-activated-carbon catalyst. (Unsaturated alcohol example) R1-5: H, C1-20 alkyl, C6-20 aryl, C6-20 heterocyclic hydrocarbon; n: 1-4 (2-propen-1-ol, 3-buten-1-ol, 4-penten-1-ol, 5-hexen-1-ol, 2-buten-1-ol, 3-penten-2-ol, 2-methyl-2-propen-1-ol, and the like). (Example of palladium-loaded-activated-carbon catalyst) A zero-valent metal palladium, a bivalent palladium compound, or a catalyst obtained by loading activated carbon with these mixtures.
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Paragraph 0019; 0021; 0023-0025; 0030; 0033; 0036

(2018/12/12)

Photosensitive resin composition for color filter and uses thereof
The present invention relates to a photosensitive resin composition for a color filter and uses thereof. The photosensitive resin composition includes an alkali-soluble resin (A), a compound (B) containing an ethylenically unsaturated group, a photoinitiator (C), a pigment (D) and an organic solvent (E). The photosensitive resin composition according to the present invention can improve linearity of pattern with high finesse and developing-resistance of the color filter.
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(2017/03/08)

MANUFACTURING METHOD OF ISOCYANURATE COMPOUND
PROBLEM TO BE SOLVED: To provide a method using a raw material with low toxicity, capable of easily controlling a reaction even with mass production equipment, and manufacturing an isocyanurate compound selectively at high yield while maintaining safety. SOLUTION: By heating a triisocyanurate compound, a carboxylic acid compound, a metallic salt and a solvent with oxygen concentration of a reaction tank inner gas phase of less than 0.4 vol.%, a raw material with low toxicity is used and a reaction even with mass production equipment can be easily controlled and an isocyanurate compound can be manufactured selectively at high yield while maintaining safety. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
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Paragraph 0040

(2017/04/27)

Preparation technology of triene allyl isocyanuric acid cross-linking agent and technological equipment thereof
The invention discloses a preparation technology of a triene allyl isocyanuric acid cross-linking agent and technological equipment thereof.The triene allyl isocyanuric acid cross-linking agent is prepared from sodium cyanate and chloropropene.In the preparation process of the triene allyl isocyanuric acid cross-linking agent, dimethyl sulfoxide is adopted as a solvent, sodium hydrogen sulfate is adopted as a catalyst, a reaction kettle and a dimethyl sulfoxide receiver are included, the dimethyl sulfoxide receiver comprises a receiving tank, a recycling pipeline is arranged between the receiving tank and the reaction kettle, and a plurality of spoilers are arranged inside the recycling pipeline.The preparation technology of the triene allyl isocyanuric acid cross-linking agent and the technological equipment are matched, so that the preparation purity of the triene allyl isocyanuric acid cross-linking agent is remarkably improved compared with the prior art.
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Paragraph 0028

(2016/12/16)

The crosslinking agent and sealing material
PROBLEM TO BE SOLVED: To specify corrosion causative substances in impurities of triallyl isocyanurate and to provide a crosslinking agent and an encapsulation material containing triallyl isocyanurate having less content of the causative substance as an active ingredient.SOLUTION: There are provided a crosslinking agent and an encapsulation material containing triallyl isocyanurate containing an organic chlorine compound represented by the chemical formula (I) with a content of 500 ppm or less as an active ingredient (I), where a bond with a wave line represents a cis type or a trans type, or a mixture of the cis type and the trans type with a specific percentage.
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Paragraph 0032; 0033

(2017/06/20)

METHOD FOR PRODUCING EPOXY COMPOUND
There is provided a method for producing an epoxy compound having an epoxy ring bonded to a triazinetrione ring via a long chain alkylene group, an olefin compound having a specific structure is used to efficiently obtain an epoxy compound of which an olefin moiety is epoxidized in high yield. A method for producing an epoxy compound of Formula (2): comprising reacting a triolefin compound of the following Formula (1): (In the above-mentioned Formulae, R1 to R9 are each independently a hydrogen atom or a methyl group; and n1 to n3 are each independently an integer of 1 to 4) with hydrogen peroxide, a nitrile compound, and an alkaline substance in a solvent. The nitrile compound is an aliphatic nitrile compound or an aromatic nitrile compound. The alkaline substance is phosphate, carbonate, or an alkaline metal hydroxide.
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Paragraph 0068

(2015/09/23)

ISOCYANURATE EPOXY COMPOUND HAVING ALKOXYSILYL GROUP, METHOD OF PREPARING SAME, COMPOSITION INCLUDING SAME, CURED PRODUCT OF THE COMPOSITION, AND USE OF THE COMPOSITION
The present invention relates to an alkoxysilyl-based isocyanurate epoxy compound, a method of preparing same, a composition including same, a cured product of the composition and a use of the composition. A complex including the compound illustrates good heat resistance, particularly, a low coefficient of thermal expansion (CTE), and a high glass transition temperature or Tg. A cured product of the composition illustrates flame retardancy and does not use a separate silane coupling agent. According to the present invention, an isocyanurate epoxy compound including an alkoxysilyl group and an epoxy group at a core; a method of preparing the epoxy compound prepared by epoxidation and alkoxysilylation of a starting material; an epoxy composition including the epoxy compound; and a cured product of the epoxy composition and a use of the epoxy composition, are provided. In the complex of the composition including the novel alkoxysilyl-based isocyanurate epoxy compound according to the present invention, chemical bonding efficiency may be improved when making a chemical bond between the alkoxysilyl group in the epoxy compound and a filler and when forming an epoxy complex through a chemical bond between alkoxysilyl groups in the epoxy compound having the alkoxysilyl group. Therefore, good heat resistance, that is, a low CTE and a high glass transition temperature or Tg may be shown. In addition, the cured product of the composition including the epoxy compound according to the present invention may show good flame retardancy.
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Paragraph 0211

(2014/09/29)

ISOCYANURATE EPOXY COMPOUND HAVING ALKOXYSILYL GROUP, METHOD OF PREPARING SAME, COMPOSITION INCLUDING SAME, CURED PRODUCT OF THE COMPOSITION, AND USE OF THE COMPOSITION
Disclosed are an alkoxysilylated isocyanurate epoxy compound, a composite of which exhibiting low CTE and high glass transition temperature or Tg-less and/or a cured product of which exhibiting good flame retardant property, a method of preparing the same, a composition including the same, a cured product formed of the composition, and a use of the composition. An isocyanurate epoxy compound having an alkoxysilyl group and an epoxy group in a core; a method of manufacturing the epoxy compound by the epoxidation and alkoxysilylation of a starting material; an epoxy composition including the epoxy compound; and a cured product and a use thereof, are provided. A composite of the epoxy composition has improved bonding efficiency between alkoxysilyl group and filler and between alkoxysilyl groups, and has good heat resistance, low CTE, and high glass transition temperature or Tg-less. A cured product formed of the epoxy composition has good flame retardant property.
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(2014/10/29)

TRIALLYLISOCYANURATE, TRIALLYLCYANURATE, AND PROCESS FOR PRODUCTION OF TRIALLYLISOCYANURATE
The present invention provides triallyl isocyanurate comprising a less amount of corrosive substances by identifying the corrosive substances among impurities included in the triallyl isocyanurate. Triallyl isocyanurate of the present invention comprises an organic chlorine compound represented by the following general formula (I) in an amount of not more than 100 ppm: wherein R1 and R2 are respectively a chlorine atom or an allyoxy group with the proviso that at least one of R1 and R2 is a chlorine atom.
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Page/Page column 7

(2012/04/17)

TRIALLYLISOCYANURATE AND PROCESS FOR PRODUCTION THEREOF
The present invention provides triallyl isocyanurate comprising a less amount of corrosive substances by identifying the corrosive substances among impurities included in the triallyl isocyanurate. Triallyl isocyanurate of the present invention comprises an organic chlorine compound represented by the following chemical formula (I) in an amount of not more than 500 ppm: wherein a bond expressed by a wavy line indicates that the organic chlorine compound is a cis-type compound, a trans-type compound or a mixture comprising the cis-type and trans-type compounds at an optional ratio.
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Page/Page column 6

(2012/04/17)

Cyclodimerization and cyclotrimerization of isocyanates promoted by one praseodymium benzenethiolate complex [Pr(SPh)3(THF)3]
The cyclotrimerization of aryl isocyanates and the cyclodimerization of alkyl isocyanates initiated by one praseodymium benzenethiolate complex [Pr(SPh)3(THF)3] were investigated. Comparative runs with [Pr(SPh)3(THF)3] and its precursor Pr[(Me 3Si)2N]3 showed that the former has the advantages of a higher selectivity toward isocyanates, easy preparation, low catalyst loading, high conversion as well as mild reaction conditions.
Wang, He-Ming,Li, Hong-Xi,Yu, Xiang-Yang,Ren, Zhi-Gang,Lang, Jian-Ping
scheme or table
p. 1530 - 1535
(2011/04/15)

PROCESS FOR PREPARING TRIALLYL ISOCYANURATE (TAIC)
The invention is directed to an improved, reliably performable process for preparing triallyl isocyanurate (TAIC) by Cu2+-catalysed rearrangement of triallyl cyanurate (TAC) at least 90° C. According to the invention, TAC and, if required, also a Cu2+ catalyst and solvent are fed continuously to a start reaction mixture after onset of the initially inhibited isomerization reaction, the isomerization is performed at from 90 to 160° C. and an amount of reaction mixture equivalent to the amount of reactant is drawn off continuously and sent to the workup. Preference is given to effecting the isomerization in TAIC as the reaction medium.
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Page/Page column 4

(2009/12/27)

The oxidation of hexahydrotriazines
N-Alkyl-2,4-dioxohexahydro-1,3,5-triazines oxidize readily with oxygen to the corresponding cyanuric acid derivates. The oxidation of 1,3,5-trimethyl-2,4- dioxohexahydro-1,3,5-triazine resulted in a stable form of hydroperoxide. During the oxidation of 1,3,5-trimethyl- 6-phenyl-2,4-dioxohexahydro-1,3,5-triazine this hydroperoxide could not be identified, however, the result was the stable reaction product bis-[6-phenyl-1,3,5-trimethyl-2,4-dioxohexahydro-1,3,5-triazin] peroxide. Springer-Verlag 2006.
Dorninger, Roland,Klepp, Kurt,Rametsteiner, Reinhard,Schiffer, Rudolf,Schmidt, Harald,Schwarzinger, Clemens
p. 185 - 190
(2007/10/03)

N-heterocyclic carbenes as highly efficient catalysts for the cyclotrimerization of isocyanates
(Chemical Equation Presented) A series of N-heterocyclic carbenes (NHCs) were evaluated as potential catalysts for the cyclotrimerization of isocyanates to afford isocyanurates. 1,3-Bis-(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2- ylidene (SIPr) was found to be a highly efficient catalyst for the cyclotrimerization of a variety of isocyanates.
Duong, Hung A.,Cross, Michael J.,Louie, Janis
p. 4679 - 4681
(2007/10/03)

Synthesis of isomelamines and isocyanurates and their biological evaluation
The reaction of cyanogen bromide (1) with primary amines (2a-p), including arylmethylamines (21-p), gave the corresponding cyanamides (3a- p). Trimerization of 3a-p gave 1,3,5-trisubstituted 2,4,6-triiminohexahydro- 1,3,5-triazines (isomelamines) (4a-p), which were treated with hydrochloric acid to give the corresponding 1,3,5-trisubstituted 2,4,6-trioxohexahydro- 1,3,5-triazines (isocyanurates) (5a-c, f) and 1,3,5-trisubstituted 2-imino- 4,6-dioxohexahydro-1,3,5- triazines (5b'-e'). Biological evaluation of 4a- p, 5a-c, f, and 5b'-e' was carried out, and some of these compounds showed bronchodilator and positive inotropic activities.
Niwa, Ryuji,Kamada, Hitoshi,Shitara, Eiki,Horiuchi, Jiro,Kibushi, Nobuyuki,Kato, Tetsuzo
p. 2314 - 2317
(2007/10/03)

Application of the study of reactivity of alkaline salts of isocyanuric acid to the synthesis of mono and trisubstituted isocyanurates
Reactivity of alkaline salts of isocyanuric acid has been studied. It has been established that the nucleophilic substitution is not selective because of the protonic exchanges between salts and substituted derivatives. The synthesis of mono or trisubstituted derivative is due to secondary reactions and to solvent effects. With this study, it has been possible to settle a method to prepare mono and trisubstituted derivatives of isocyanuric acid.
Chiron-Charrier,Caubere
p. 2659 - 2672
(2007/10/02)

INTER- AND INTRAMOLECULAR REARRANGEMENTS OF CYANURIC ACID TRIALLYL ESTERS
It is shown that the catalytic and thermal rearrangements of cyanuric acid triallyl esters to isocyanuric acid esters proceed via inter- and intramolecular mechanisms.Cross-reaction products are formed when the reaction is carried out with a mixture of homologs, while the reaction in the presence of a hydroxy-containing compound gives its allyl ether and diallyl isocyanurate.
Likhterov, V. R.,Klenovich, S. V.,Etlis, V. S.,Tsareva, L. A.,Pomerantseva, E. G.,Shmuilovich, S. M.
p. 308 - 311
(2007/10/02)