947-19-3 - Names and IdentifiersName1-hydroxycyclohexyl phenyl ketoneSynonymsHCPKUI802UV-184IHT
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| Name | 1-hydroxycyclohexyl phenyl ketone |
| Synonyms | HCPK UI802 UV-184 IHT-PI184 IHT-PI 184 Irgacure 184 PHOTOCURE-184 Photoinitiator 184 Photoinitiator-184 1-Benzoylcyclohexanol Phenyl 1-hydroxycyclohexyl ketone 1-hydroxycyclohexyl phenyl ketone 1-Hydroxy Cyclohexyl Phenyl Ketone l-Hydroxy-Cyclohexyl-Phenyl-Ketone 1-Hydroxy cyclohexyle phenyl ketone 1-Hydroxy-1-cyclohexyl phenyl ketone (1-hydroxycyclohexyl)phenyl-methanon Phenyl(1-hydroxycyclohexyl)methanone (1-Hydroxycyclohexyl)-phenylmethanone (1-hydroxycyclohexyl)phenyl-Methanone (1-hydroxycyclohexyl)(phenyl)methanone 1-(1-Hydroxy)cyclohexyl-1-phenyl ketone bis[2-(1-hydroxycyclohexyl)phenyl]methanone |
| CAS | 947-19-3 |
| EINECS | 213-426-9 |
| InChI | InChI=1/C25H30O3/c26-23(19-11-3-5-13-21(19)24(27)15-7-1-8-16-24)20-12-4-6-14-22(20)25(28)17-9-2-10-18-25/h3-6,11-14,27-28H,1-2,7-10,15-18H2 |
| InChIKey | QNODIIQQMGDSEF-UHFFFAOYSA-N |
| Molecular Formula | C13H16O2 |
| Molar Mass | 204.26 |
| Density | 1,17 g/cm3 |
| Melting Point | 47-50°C(lit.) |
| Boling Point | 175°C15mm Hg(lit.) |
| Flash Point | >150°C |
| Water Solubility | Slightly soluble in water (1108 mg/L at 25°C). Soluble in acetone, butyl acetate, methanol and toluene. |
| Solubility | Acetonitrile (Slightly), Chloroform (Slightly) |
| Vapor Presure | 0.02Pa at 20℃ |
| Appearance | White crystal |
| Color | White to Off-White Low-Melting |
| BRN | 2330973 |
| pKa | 13.23±0.20(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Refractive Index | 1.5170 (estimate) |
| MDL | MFCD00059561 |
| Physical and Chemical Properties | White crystal. Melting point 55-57 ℃. |
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36 - Irritating to the eyes |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | - |
| TSCA | Yes |
| HS Code | 29144000 |
| LogP | 2.81 at 25℃ |
| Introduction | 1-hydroxycyclohexyl Phenyl Ketone (184) is a new type of high efficiency photoinitiator introduced by Swiss company in Ciba-Geigy, product Code for Irg acure 184, melting point 47~49 ℃. It is an efficient, yellowing-resistant free radical (I)-type solid photoinitiator, with the advantages of long storage time, high initiation efficiency, wide UV absorption range, it is mainly used in combination with mono-or multi-functional vinyl monomers and Oligomers for UV curing of unsaturated prepolymers (e. G. Acrylate), and is especially suitable for coatings and inks with high requirements for yellowing. |
| physical properties | 64% appearance white crystal melting point 44 - 48 ℃ flash point> 150 ℃ boiling point 175 ℃ absorption wavelength 244, 280,330 nm content ≥ 99% |
| Application | 1-hydroxycyclohexylphenyl ketone is an efficient free-radical non-yellowing photoinitiator, it is also one of the most commonly used initiators for UV curing systems. Because of its good non-yellowing denaturation, it can be used for UV polymerization of mono-functional or multi-functional polymerization of acrylate monomers and oligomers, and can also be used in varnishes, plastic coatings, wood coatings, adhesives, lithographic printing ink, screen printing ink, flexo printing ink, electronic products, the cured coating even if exposed to sunlight for a long time, because of its photolysis without benzyl group, the degree of yellowing is very small, it is therefore particularly useful in coatings and inks that require a high degree of yellowing. Its photolysis products include benzaldehyde and cyclohexanone, which have a certain odor after film formation. Application in the surface curing system and TPO with the use of good results, the recommended dosage of 2-5w/w. The yellowing of the acrylic/polyurethane system in outdoor use can be effectively reduced by adding other additives. |
| preparation | 1) acylation: add cyclohexylcarboxylic acid into the reaction kettle, raise the temperature to 35±2 ℃, add phosphorus trichloride, after keeping the temperature at 60±2 ° C. For at least 4 hours, the inorganic layer is removed to obtain cyclohexanoyl chloride; Wherein the weight ratio of the raw material cyclohexylformic acid to phosphorus trichloride is 1.8-2.2:1;2) friedel-Crafts reaction: the benzene and the catalyst aluminum trichloride are added to the reaction kettle, cooled to 5-10 ℃, and then add the cyclohexanoyl chloride, benzene, the weight ratio of aluminum trichloride to cyclohexanoyl chloride is 9:2.9-3.1:3.16-3.36, and the temperature is 15±2 ° C. For at least 2.5 hours to obtain the complex sum of cyclohexylphenyl ketone and aluminum trichloride; 3) hydrolysis reaction: the appropriate amount of the mass concentration of 1.5-2.5% of dilute hydrochloric acid into the complex, Mixing the layers, separating the water layer containing aluminum trichloride, then adding appropriate amount of water washing acid, until the end of pH>5, and finally removing the unreacted raw material benzene by distillation to obtain cyclohexyl Phenyl Ketone; 4) chlorination reaction: add cyclohexyl Phenyl Ketone to the chlorination kettle, raise the temperature to 60±2 ℃, then inject chlorine gas, and the reaction is finished to obtain 1-chlorocyclohexyl Phenyl Ketone; 5) alkaline hydrolysis reaction: 1:0.95-1.10 add 1-chlorocyclohexylphenylketone to liquid base, stir until the reaction is finished, then add toluene to extract, separate the aqueous phase, dissolves, and recover toluene, obtaining a crude product of 1-hydroxycyclohexylbenzophenone; 6) refining: placing the crude product of 1-hydroxycyclohexylbenzophenone in a rectification kettle, rectifying the product under reduced pressure by a Roots pump, and collecting fractions; put the product from the distillation into the crystallization kettle, Then petroleum ether is dissolved and recrystallized, and then centrifugal separation is carried out, and the solvent petroleum ether is distilled out of the distillation mother liquor for reuse, and the finished product 1-hydroxycyclohexylbenzophenone is obtained after drying the wet product. |
| Use | for paper, wood, UV-curing of acrylic varnish coatings on metal and plastic surfaces used as efficient UV-curable initiator and non-yellowing photoinitiator UV-curable coatings and inks |
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