A slip agent, its preparation method and use

Abstract

The application discloses a slip agent, a preparation method and application thereof, and a structure formula of the slip agent is shown as the following formula I. The slip agent is sprayed on a polyolefin elastomer (POE) surface, can make a friction coefficient small (lower than 0.2), can prevent POE particles from being adhered, and can make the POE particles be stored at high temperature for more than 30 days without being adhered.

Description

Technical Field

[0001] This invention belongs to the field of polymer material preparation technology, specifically relating to a slip agent, its preparation method, and its application. Background Technology

[0002] Polyolefin elastomer (POE) particles have low melting points and are prone to sticking together, easily leading to bridging in storage bins. Therefore, a slip agent needs to be sprayed onto the POE surface to prevent sticking. In existing technologies, adding slip agents can prevent material sticking during processing, storage, or use. Commonly used slip agents include silicone oil, calcium stearate, oleamide, erucamide, stearamide, inorganic slip agents, and ethylene bis-stearamide (EBS) derivatives. However, these slip agents tend to migrate from the interior of the film to the surface, forming an oil film or white powder over time, increasing haze and affecting the film's transparency and appearance. Furthermore, the migration rate of the slip agent is significantly affected by temperature; high temperatures accelerate migration, leading to instability in the film's surface friction coefficient. Summary of the Invention

[0003] To address the aforementioned technical problems, the present invention provides a slip agent as shown in Formula I:

[0004]

[0005] In Equation 1, R1 is selected from C 5-25 Alkyl or C 5-25 Alkenyl;

[0006] R2 is selected from C 6-30 Aliphatic alkyl groups and C 6-30 Aliphatic alkenyl groups;

[0007] R3 is selected from C 6-30 Aliphatic alkyl groups and C 6-30 Aliphatic alkenyl groups.

[0008] According to an embodiment of the present invention, R1 is selected from C. 5-12 Alkyl or C 5-12 Alkenyl groups. For example, R1 can be pentyl, hexyl, heptyl, 1-methyl-hexyl, octyl, 1-methyl-octyl, nonyl, etc.

[0009] According to an embodiment of the present invention, R2 is selected from C. 6-12 Aliphatic alkyl groups and C 6-12 Aliphatic alkenyl chains. For example, R2 can be hexyl, heptyl, 1-methyl-hexyl, octyl, 1-methyl-octyl, nonyl, etc.

[0010] According to an embodiment of the present invention, R3 is selected from C. 6-12 Aliphatic alkyl groups and C 6-12Aliphatic alkenyl groups. For example, R2 can be hexyl, heptyl, 1-methyl-hexyl, octyl, 1-methyl-octyl, nonyl, etc.

[0011] The present invention also provides a method for preparing the above-mentioned slip agent, the method comprising:

[0012] The slip agent is obtained by mixing and reacting the carboxylic acid ester compound shown in Formula II, the secondary amine compound shown in Formula III, and a catalyst in an organic solvent;

[0013]

[0014] In Formula II, R is selected from hydrocarbon groups with 1 to 4 carbon atoms; R1, R2, and R3 have the meanings described above.

[0015] According to an embodiment of the present invention, the molar ratio of the carboxylic acid ester compound to the secondary amine compound is 0.5:1 to 2:1, preferably 0.75:1 to 1.25:1, and even more preferably 0.95:1 to 1.05:1.

[0016] According to an embodiment of the present invention, the reaction temperature is 10–200°C, preferably 20–160°C.

[0017] According to an embodiment of the present invention, the reaction time is 0.5 to 24 hours, preferably 1 to 12 hours.

[0018] According to an embodiment of the present invention, the organic solvent is selected from at least one of acetonitrile, methanol, ethanol, etc. In the present invention, the content of the organic solvent is not particularly limited, as long as it is sufficient to completely or partially dissolve all raw materials.

[0019] According to an embodiment of the invention, the catalyst is, for example, sodium hydroxide or potassium carbonate.

[0020] According to an embodiment of the present invention, the molar ratio of the catalyst to the secondary amine compound is 0.01 to 0.5:1, preferably 0.1 to 0.5:1.

[0021] The present invention also provides the application of the above-mentioned slip agent in reducing the viscosity of polyolefin elastomers.

[0022] In the production process of POE, the slip agent of the present invention can be added to the POE melt in the form of a solution (a suitable solvent is known to those skilled in the art) or in the form of a pure substance, and then flash evaporated before being fed into an extruder for granulation; or the slip agent of the present invention can be mixed with POE granules and then granulated by an extruder; or the slip agent of the present invention can be sprayed onto POE granules in the form of a solution (a suitable solvent is known to those skilled in the art).

[0023] The beneficial effects of this invention are:

[0024] The inventors unexpectedly discovered that spraying the slip agent of the present invention onto the surface of polyolefin elastomer (POE) can reduce the coefficient of friction (below 0.2) and prevent POE particles from sticking together, allowing POE particles to remain intact for more than 30 days at high temperatures without sticking together.

[0025] The slip agent of this invention has excellent compatibility as a filler in polyolefin elastomers (POE) and does not precipitate. Detailed Implementation

[0026] The technical solution of the present invention will be further described in detail below with reference to specific embodiments. It should be understood that the following embodiments are merely illustrative and explanatory of the present invention, and should not be construed as limiting the scope of protection of the present invention. All technologies implemented based on the above content of the present invention are covered within the scope of protection intended by the present invention.

[0027] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods.

[0028] Example 1

[0029] 9.9 mmol (1.428 g) of methyl 1-methyl-heptanoate (i.e., in Formula II, R1 is 1-methyl-hexyl) [after dehydration and purification, water content <50 ppm] was placed in a flask. 60 mL of acetonitrile and 9.1 mmol (1.157 g) of dioctylamine were then added to the flask. The temperature of the reaction mixture was controlled at 60 °C, and the mixture was stirred for 20 min. Then, 0.2 mmol (0.008 g) of sodium hydroxide was added, and the temperature was raised to 130 °C for 8 h. The crude product was obtained, and after further distillation, the product lubricant (in Formula I, R1 is 1-methyl-hexyl, and R2 and R3 are both octyl) was obtained, with a yield of 96%.

[0030] Example 2

[0031] 9.9 mmol (1.705 g) of methyl nonanoate (i.e., R1 is octyl in Formula II) [after dehydration and purification, with water content <50 ppm] was placed in a flask. 60 mL of acetonitrile and 9.9 mmol (1.835 g) of dihexylamine were then added to the flask. The temperature of the reaction mixture was controlled at 60 °C, and the mixture was stirred for 20 min. Then, 0.2 mmol (0.008 g) of sodium hydroxide was added, and the temperature was raised to 140 °C for 9 h. The crude product was obtained, and after further distillation, the product slip agent (R1 is octyl in Formula I, and R2 and R3 are both hexyl) was obtained, with a yield of 97%.

[0032] Comparative Example 1

[0033] The difference between Comparative Example 1 and Example 1 is that Comparative Example 1 uses 9.1 mmol octylamine (1.32 g) instead of 9.1 mmol dioctylamine (1.157 g).

[0034] Test Example 1

[0035] 0.1 parts of the slip agent prepared in Examples 1-2 and Comparative Example 1 were respectively mixed with POE (POE obtained by copolymerization of ethylene and 1-butene, melt index 5 g / 10 min, density 0.865 g / cm³). 3 100 parts of antioxidant (1010) and 0.5 parts of zinc stearate were mixed in a high-speed mixer. After being mixed evenly, the mixture was discharged and extruded into granules on a twin-screw extruder. The extrusion process parameters were: temperature 220℃.

[0036] Friction coefficient test: GB / T10006-1998 (ASTM D1894).

[0037] The prepared particles were stored at 35°C to test their high-temperature stability.

[0038] The test results are shown in Table 1 below.

[0039] Table 1

[0040]

[0041] Test Example 2

[0042] Dissolve 0.1 parts of the slip agent prepared in Examples 1-2 and Comparative Example 1 in toluene to obtain a slip agent solution.

[0043] POE was produced from ethylene and 1-butene (POE had a melt index of 5 g / 10 min and a density of 0.865 g / cm³). 3 During the process, a toluene solution of antioxidant (1010) (0.5 parts of antioxidant (1010) content), a toluene solution of zinc stearate (0.5 parts of zinc stearate) and the above-mentioned slip agent solution are added to 100 parts of POE melt discharged from the reactor. After flash evaporation and devolveing, the melt is extruded and granulated in an extruder. The extrusion process parameters are: temperature 220℃.

[0044] The test results are shown in Table 2 below.

[0045] Table 2

[0046]

[0047] The embodiments of the present invention have been described above by way of example. However, the scope of protection of the present invention is not limited to the above embodiments. Any modifications, equivalent substitutions, improvements, etc., made by those skilled in the art within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. A slip agent as shown in Formula I, In Equation 1, R1 is selected from C 5-25 Alkyl or C 5-25 Alkenyl; R2 is selected from C 6-30 Aliphatic alkyl groups and C 6-30 Aliphatic alkenyl groups; R3 is selected from C 6-30 Aliphatic alkyl groups and C 6-30 Aliphatic alkenyl groups.

2. The method for preparing the slip agent according to claim 1, characterized in that, The method includes: The slip agent is obtained by mixing and reacting the carboxylic acid ester compound shown in Formula II, the secondary amine compound shown in Formula III, and a catalyst in an organic solvent; In Formula II, R is selected from hydrocarbon groups with 1 to 4 carbon atoms; R1, R2, and R3 have the meanings described above.

3. The method according to claim 2, characterized in that, The molar ratio of the carboxylic acid ester compound to the secondary amine compound is 0.5:1 to 2:

1.

4. The method according to claim 2, characterized in that, The reaction temperature is 10–200°C.

5. The method according to claim 2, characterized in that, The reaction time is 0.5 to 24 hours.

6. The method according to claim 2, characterized in that, The organic solvent is selected from at least one of acetonitrile, methanol, and ethanol.

7. The method according to claim 2, characterized in that, The catalyst is sodium hydroxide or potassium carbonate.

8. The method according to claim 2, characterized in that, The molar ratio of the catalyst to the secondary amine compound is 0.01 to 0.5:

1.

9. The application of the slip agent according to claim 1 in reducing the viscosity of polyolefin elastomers.

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