TWI293296B - Novel trioxepan compounds - Google Patents

Description

1293296 A7 B7 V. INSTRUCTIONS (1) The present invention relates to two novel trioxocyclic compounds or substituted 1,2,4-dioxolone. Organic peroxides have long been known for many uses. One such known compound can be found, for example, Kirk & 〇thmer, s Encycl〇pedia 〇f

Chem·Tech·, 3rd Ed, Vol. 17, p. 57, is a trioxane of the formula (8).

W0 98/50354 proposes the use of this compound and four related trioxyheptacyclic compounds (including the product of formula (Y)) in combination with a cross-linking agent.

八一〇 ch3 ch3 Λ · 3 (7) solid content acrylic

-Methylhexyl and 3,6,9 diethylethyl-3,6,9-tri are insufficient for use in, for example, controlled decomposition of polypropylene and/or high solids ester polymerization. Maybe it’s because of j. Substantially 4 peroxides must be surprisingly good - good properties, can be used as peroxidation in these processes, t-butylperoxy-2,5-dimethylhexane and 3

1293296 A7 B7 V. INSTRUCTIONS (3) Direct use without purification.

Paste 1-5 and Comparative Example AH In these examples, the peroxide (if used) is dissolved in dioxane (about 5% by weight solution) and with PP to introduce 0.005 wt% or 0.01 wt% active oxygen ( Mix the amount by weight of the polypropylene, please refer to the attached table below. Also, 1% by weight of Irganox 81010 stabilizer was added to the weight of the PP. This mixture was placed in a cabinet and allowed to stand overnight at room temperature to remove the dichloromethane. The resulting mixture was introduced into Haake Rheocord® system 40 using a Plasticolor 2000 single screw pump (Model 15/22 with a Rheomex 8 TW100 intensive mixing screw). To maintain low oxygen conditions, nitrogen was introduced into the feed hopper (2.5 L/min). ) and surround the Rheocord mold (9 liters / minute). During the extrusion process, the screw speed is set to 50 rpm and the temperature is set at 190/250/250/25 0 °C (condition 1) or 160/225/225/225 ° C (Condition 2) The resulting strip was cooled in a water bath and granulated by an Automatik® ASG5 granulator. The granules were dried overnight at 60 ° C before analysis. In a conventional manner, 8.3 butyl 1 〇 1238 (230°) was used. (:/2.16 kg) Analysis of the MFI of the polymer. The following results were obtained: -6- This paper scale applies to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 1293296 A7 B7 V. Description of invention (4) Example Peroxidation Active Oxygen Compressor Conditional Torque in Material PP (Nm) MFI (g/10 min) 1 Formula I 0.005% 1 16 82 2 Formula I 0.010% 1 13 215 3 Formula I 0.010% 2 25 292 4 Formula II 0.005% 2 29 112 5 Formula II 0.010% 2 25 265 A No 0 1 24 3 B No 0 2 23 3 C Formula X 0.010% 2 26 228 D Formula Υ 0.010% 1 32 14 E Trigonox® 101 0.005% 1 34 30 F Trigonox® 101 0.010% 2 32 71 G Trigonox® 301 0.010% 1 18 84 Η Trigonox® 301 0.010% 2 28 84 This display Compounds I and II are very effective in controlling PP decomposition (especially in terms of PP with high MFI). Poor effect of product X may be partially related to its volatility. Real ^ (column 6 to 8 spear comparison {column I彳Port J In these examples, a glass reactor having a jacket diameter of 60 mm and a height of 80 mm and equipped with a turbine agitator, a retorting condenser and an injection port was used, and acrylate was polymerized in a solvent. Solvent (40 g) was added to In the reactor, the temperature was adjusted so that the half-life of the peroxide used in the experiment was 15 minutes at this temperature. The polymerization temperature was as high as 126 ° C (inclusive), using butyl acetate as the solvent. For 126 °C up to 165 °C (inclusive), use Solvesso8100, while Exxate8700 is used for polymerization temperatures from 165-200 °C. The use of nitrogen gives polymerization conditions free of oxygen. This paper scale applies to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 1293296 V Description of invention (5 A7 B7

Monomer (40 grams of butyl acrylate, 28 grams of hydroxyethyl methacrylate, 2 grams of styrene, 10 grams of methacrylate and 2 grams of methacrylate) and 30 milliequivalents (relative to each oxime bond per molecule) The compound, which is 3 〇亳 mol, is a 005 亳 molar relative to a compound with two 00 bonds per molecule, and so on. The initiator is introduced to the anti-staghorn using a Watson Marlow pump for 4 hours. in. Thereafter, the polymerization was further carried out for one hour at the same temperature. ^ The resulting polymer was analyzed in a conventional manner. Using polystyrene as a standard, the molecular weight was determined by ΗΡ-SEC. The solid content of the obtained resin (solid) was determined by gravimetric analysis. · About 1 gram of the resin was accurately weighed, and the sample was dissolved in about 1 gram of benzene, and air-cooled in a furnace at M125t: dried for 4 hours. After the sample is cooled, the weight of the remaining material is divided by the original sample weight and the resulting value is the solid amount. The viscosity was measured at 25 ° C using a Brookfield viscometer. The reference product "cyclic-MIAKP" was prepared using the procedure for composition v in WO 96/03397, but isoamyl ketone was used here instead of isobutyl ketone. The product was diluted and contained 67.3% by weight of peroxide. Use another reference

Trigonox® 301 (cyclic MEK peroxide, a 41% solution in odorless mineral spirits) available from Akzo Nobel. These compounds are considered as representative examples of novel high solid content acrylate polymerization initiators. The trioxyheptacyclic compound according to the present invention is a technically pure form having a peroxide content of more than 95% by weight. The results obtained are as follows: 1293296 A7 B7 V. Description of invention (6) Example Peroxide polymerization temperature Solid (%) Mw Μη D 6 Formula I 180 69.9 4,500 1,750 2.5 7 Formula I 200 70.0 2,400 1,300 1.8 8 Formula II 165 69.2 5,700 2,750 2.0 I Ring-MIAKP 180 70.8 6,000 1,900 3.1 J Trigonox® 301 200 71.3 2,900 1,500 2.0 These results show that the trioxane compound according to the present invention is very acrylate resin which has a low molecular weight and a high solid content and a narrow molecular weight distribution. An effective initiator. _-9- This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm)

Claims (1)

Patent Application No. I293|9622492 A8 B8 C8 Replacement of Chinese Patent Application (November 1993) D8 VI. Scope of Application 1. A compound of the following formula 2. - a compound of the formula 3. A composition for decomposing polypropylene and producing a polyacrylate comprising at least one compound as claimed in claim 1 or 2 and a diluent. This paper scale applies to the Chinese National Standard (CNS) A4 specification (210 X 297 mm)