KR20180110793A - Dispersant for rubber composition and rubber composition comprising the same - Google Patents

Abstract

The present invention relates to a novel dispersant for a rubber composition which uniformly disperses a silica-based reinforcing agent contained in the rubber composition with respect to rubber, thereby excellently expressing the mechanical properties of the rubber composition. The present invention also relates to the rubber composition comprising the dispersant. The dispersant for a rubber composition contains a specific compound represented by chemical formula 1.

Description

DISPERSANT FOR RUBBER COMPOSITION AND RUBBER COMPOSITION COMPRISING THE SAME [0002]

The present invention relates to a novel dispersant for a rubber composition capable of uniformly dispersing a silica-based reinforcing agent contained in a rubber composition to rubber, and exhibiting excellent mechanical properties of the rubber composition, and a rubber composition containing the same.

BACKGROUND ART Various rubber compositions have been used in the past to manufacture rubber products contained in various daily necessities such as shoe soles. Such a rubber composition generally contains a silica-based reinforcing agent together with a rubber component in order to improve various mechanical properties such as tensile strength, tear strength or abrasion resistance.

However, the silica-based reinforcing agent has poor compatibility and interactivity with the rubber component showing non-polarity, and has a strong cohesive force between the silica-based reinforcing agents. Therefore, it is difficult to uniformly disperse the silica-based reinforcing agent in the rubber, and it is not only difficult to sufficiently attain the effect of improving the mechanical properties, but also disadvantageously disadvantageously occurs during processing such as crosslinking and vulcanization of the rubber composition.

In order to improve the dispersibility of the silica-based reinforcing agent to rubber, a dispersant containing a fatty acid salt of a metal ion belonging to heavy metals has been typically used. However, these heavy metals are regulatory components that are likely to cause toxicity in the ecosystem, and the reduction of such components is continuously required.

Thereby, a novel dispersant for rubber compositions which can uniformly disperse the silica-based reinforcing agent contained in the rubber composition in the rubber, without containing such a heavy metal component, and can excellently express the mechanical properties of the rubber composition Development is constantly being requested.

Accordingly, the present invention provides a novel organic dispersant for rubber compositions capable of uniformly dispersing a silica-based reinforcing agent contained in a rubber composition in a rubber composition without containing a heavy metal component and exhibiting excellent mechanical properties of the rubber composition .

Further, the present invention is to provide a rubber composition containing the above-mentioned dispersant and exhibiting excellent mechanical properties.

Accordingly, the present invention provides a dispersant for a rubber composition comprising a compound represented by the following Formula 1:

[Chemical Formula 1]

이고, R은 수소, 탄소수 10 내지 30의 알킬기, 비닐기 또는 탄소수 10 내지 30의 알케닐기이고, 점선은 이중 결합이 있거나 없을 수 있음을 나타내고, m은 1 내지 3 의 정수이고, X is -OR1, -NHR1 or -N (R1) ₂ , Y is -OR2, -NHR2 or -N (R2) ₂ , R1 and R2 are each independently the same or different R3 is hydrogen, an alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms, A hydroxyalkyl group or

, R is hydrogen, an alkyl group having 10 to 30 carbon atoms, a vinyl group or an alkenyl group having 10 to 30 carbon atoms, a dotted line indicates that there may be a double bond or absent, m is an integer of 1 to 3,

And at least one of R1 and R2 is hydrogen when X and Y are different from each other, -OR1 and -OR2.

The present invention also relates to a rubber composition comprising: rubber; Silica-based reinforcing agents; And a rubber composition comprising the dispersant.

Hereinafter, a dispersant for a rubber composition and a rubber composition containing the same according to a specific embodiment of the present invention will be described in more detail.

According to one embodiment of the invention, there is provided a dispersant for a rubber composition comprising a compound of the formula:

[Chemical Formula 1]

이고, R은 수소, 탄소수 10 내지 30의 알킬기, 비닐기 또는 탄소수 10 내지 30의 알케닐기이고, 점선은 이중 결합이 있거나 없을 수 있음을 나타내고, m은 1 내지 3 의 정수이고, X is -OR1, -NHR1 or -N (R1) ₂ , Y is -OR2, -NHR2 or -N (R2) ₂ , R1 and R2 are each independently the same or different R3 is hydrogen, an alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms, A hydroxyalkyl group or

, R is hydrogen, an alkyl group having 10 to 30 carbon atoms, a vinyl group or an alkenyl group having 10 to 30 carbon atoms, a dotted line indicates that there may be a double bond or absent, m is an integer of 1 to 3,

And at least one of R1 and R2 is hydrogen when X and Y are different from each other, -OR1 and -OR2.

The inventors of the present invention have found through experiments such as the following examples that the silica-based reinforcing agent can be uniformly dispersed and mixed in the rubber composition without the heavy metal component, .

This is because the compound of the formula (1) has a non-polar functional group such as a hydrocarbon-based functional group having a relatively long chain length (for example, an alkyl group or an alkenyl group having 5 or more carbon atoms or more) and a polar functional group such as a carboxylic acid group, Is included in the molecule. That is, it appears that the non-polar functional groups can be miscible and interact with the rubber component, and the silica-based reinforcing agent can be effectively incorporated and dispersed into the rubber as the polar functional groups are mixed and interacted with the silica-based reinforcing agent.

Therefore, when the dispersant of one embodiment is used, the silica-based reinforcing agent can be uniformly dispersed in the rubber to exert excellent mechanical properties such as tensile strength, tear strength, modulus and elongation of the rubber composition, So that the workability can be kept excellent.

Therefore, by using the dispersant of one embodiment, various rubber compositions and rubber molded articles which can be suitably used for producing rubber for various household goods such as shoe soles can be produced.

On the other hand, in the dispersant of the embodiment described above, the alkenyl group having 10 to 30 carbon atoms in Formula 1 may be an allyl group represented by -CH2-CH = CH-R4 (wherein R4 is an alkyl group having 7 to 27 carbon atoms) . As a result, not only the silica-based reinforcing agent can be more effectively dispersed, but also the crosslinking time of the rubber composition can be further shortened by facilitating the crosslinking of the rubber composition, and the mechanical properties such as tear strength and abrasion resistance of the rubber composition Can be improved.

In addition, the compound of formula (1) described above may be such that X and Y are the same functional group, X and Y are different from each other, and at least one of X and Y is -OH (that is, at least one of R 1 and R 2 is hydrogen) . In particular, when X and Y are different from each other, -OR1 and -OR2, at least one of R1 and R2 is necessarily hydrogen.

In a more specific example, when X and Y are the same functional group, X and Y may be -OH, or -OH may be bonded to the terminal. In this case, R is preferably an alkyl group having 10 to 30 carbon atoms or an alkenyl group having 10 to 30 carbon atoms.

When X and Y are different from each other and at least one of X and Y is -OH (at least one of R 1 and R 2 is hydrogen), the remaining X or Y contains an alkyl group having 5 or more carbon atoms, or R has a carbon number of 10 More preferably an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 10 to 30 carbon atoms.

As a result, the compound of Formula 1 can more effectively disperse the silica-based reinforcing agent to the rubber.

Meanwhile, the most specific examples of the compound of formula (1) described above can be represented by the following formulas, but the scope of the compound of formula (1) is not limited to the following:

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The compound of formula (1) is typically an acid anhydride of a succinic anhydride or a maleic anhydride having the functional group R and an alcohol corresponding to X and Y, for example, X- (O) H or Y- (O ) H in the presence of a base. However, the reaction conditions in this production method are specifically described in the following examples, and the reaction conditions between the acid anhydride and the alcohol can be customized, so that a further explanation thereof will be omitted.

The above-mentioned compound of the formula (1) is contained in a rubber composition containing a rubber and a silica-based reinforcing agent, and can be used for uniformly mixing and dispersing a silica-based reinforcing agent to rubber.

According to another embodiment of the invention, there is provided a rubber composition comprising the dispersant of one embodiment described above. Such rubber compositions include, for example, rubber; Silica-based reinforcing agents; And dispersants of one embodiment described above.

Such a rubber composition includes the above-mentioned dispersant, and it is possible to provide a rubber composition having excellent mechanical properties such as excellent workability of short crosslinking time and high tear strength, tensile strength, elongation, modulus and abrasion resistance without containing or containing a heavy metal component in a very small content Physical properties can be shown.

In the rubber compositions of other embodiments described above, the rubber may comprise at least one of natural rubber and synthetic rubber. Specific examples of the synthetic rubber include halogen-modified or unmodified isobutylene isoprene rubber or butadiene rubber. However, it is not particularly limited and may include any synthetic rubber previously known.

In addition to the above-mentioned components, the rubber composition may also contain a crosslinking agent (vulcanizing agent) such as a process oil such as carbon black, a silane coupling agent and paraffin oil, a tackifier, fatty acids such as stearic acid, sulfur, Or an additive such as a crosslinking accelerator such as a mercaptobenzothiazole. In addition, various additives previously known to be included in the rubber composition can be included without limitation.

The rubber composition described above can be formed into a first composition state by blending rubber, a silica-based reinforcing agent, and a dispersant of the above-described embodiment with optional additives such as carbon black, silane coupling agent, process oil, tackifier and fatty acid Then, a cross-linking agent (vulcanizing agent), a cross-linking assistant, a cross-linking accelerator and the like are further added to such a carbon master batch, and crosslinking and vulcanization proceed while heating under pressure. The rubber composition may refer to any state ranging from the primary composition state described above to the final rubber molded article form.

In the meantime, the method and conditions for the compounding of the rubber composition, the addition of various components for crosslinking, and the crosslinking (vulcanization) process are the same as those of general rubber compositions and molded articles, .

The rubber compositions of the other embodiments described above may include a dispersant of one embodiment, and may exhibit excellent processability and excellent mechanical properties, with or without a very small amount of heavy metal component. Therefore, such a rubber composition can be used very favorably for producing rubber for various household goods such as shoe soles.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a novel organic dispersant for a rubber composition which can uniformly disperse a silica-based reinforcing agent contained in a rubber composition, without containing a heavy metal component, May be provided.

By using such an organic dispersant, various rubber molded articles which can exhibit excellent mechanical properties and workability (short crosslinking time and the like) and can be suitably used for rubbers for various household goods such as shoe soles can be produced and provided.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, these embodiments may be modified into various other forms, and the scope of the invention is not construed as being limited to the embodiments described below.

Example 1: Preparation of dispersant for rubber composition

Octadecylsuccinic anhydride and 2-ethylhexanol were placed in a 3-neck round flask at an equivalence ratio (1: 1) and reacted at 180 ° C for 4 hours. The unreacted 2-Ethylhexanol was then removed using a Vacuum Oven to produce an orange liquid. (Yield 62%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 9H), 1.2-1.4 (m, 38H), 1.5 (t, 4H), 2.4 (m, 1H), 2.7-2.9 (m, 3H) , ≪ / RTI > 4.0 (m, 2H).

Example 2: Preparation of dispersant for rubber composition

Octadecylsuccinic anhydride and stearyl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 120 ° C for 4 hours. Thereafter, unreacted stearyl alcohol was removed using Vacuum Oven to yield a white solid material. (Yield: 71%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.2-1.4 (m, 56H), 1.5 (m, 2H), 1.6-1.7 (m, 4H), 2.4 (m, 1H) , 2.7 (m, 1 H), 2.9 (m, 1 H), 4.1 (t, 2 H).

Example 3: Preparation of dispersant for rubber composition

Octadecylsuccinic anhydride and Lauryl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 150 ° C for 5 hours. Thereafter, the unreacted Lauryl alcohol was removed using Vacuum Oven to produce a slightly yellow liquid. (93% yield)

¹ H NMR (600 MHz, CDCl ₃ ):? 0.9 (t, 9H), 1.2-1.4 (m, 46H) , ≪ / RTI > 4.0 (m, 2H).

Example 4: Preparation of dispersant for rubber composition

Octadecylsuccinic anhydride and tridecyl alcohol were placed in a 3-neck round flask at an equivalence ratio (1: 1) and reacted at 120 ° C for 6 hours. Thereafter, the unreacted tridecyl alcohol was removed using Vacuum Oven to produce a slightly yellow solid material. (Yield: 92%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 9H), 1.2-1.4 (m, 44H), 1.5 (t, 4H), 2.4 (m, 1H), 2.7-2.9 (m, 3H) , ≪ / RTI > 4.0 (m, 2H).

Example 5: Preparation of dispersant for rubber composition

Dodecylsuccinic anhydride and 2-ethylhexanol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 120 ° C for 6 hours. The unreacted 2-Ethylhexanol was then removed using Vacuum Oven to produce a yellow liquid. (Yield: 91%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 9H), 1.2-1.4 (m, 26H), 1.5-1.6 (m, 4H), 1.6-1.7 (m, 1H), 2.4 (m, 1H), 2.7 (m, 1H), 2.8 (m, 1H), 4.0 (m, 2H).

Example 6: Preparation of dispersant for rubber composition

Dodecylsuccinic anhydride and Lauryl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 150 ° C for 5 hours. The unreacted 2-Ethylhexanol was then removed using Vacuum Oven to produce a yellow liquid. (93% yield)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 9H), 1.1-1.3 (m, 38H), 1.5 (m, 2H), 1.6-1.7 (m, 2H), 2.3 (m, 1H) , 2.6 (m, 1 H), 2.7 (m, 1 H), 4.0 (t, 2 H).

Example 7: Preparation of dispersant for rubber composition

Dodecylsuccinic anhydride and tridecyl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 120 ° C for 5 hours. Then, when the unreacted tridecyl alcohol was removed using Vacuum Oven, a yellow liquid substance was produced. (Yield: 91%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 9H), 1.1-1.3 (m, 38H), 1.5 (m, 2H), 1.6-1.7 (m, 2H), 2.3 (m, 1H) , 2.6 (m, 1 H), 2.7 (m, 1 H), 4.0 (t, 2 H).

Example 8: Preparation of dispersant for rubber composition

Hexadecylsuccinic anhydride and 2-ethylhexanol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 120 ° C for 5 hours. The unreacted 2-Ethylhexanol was then removed using Vacuum Oven to produce a yellow liquid. (Yield: 94%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 9H), 1.1-1.3 (m, 34H), 1.4 (m, 4H), 1.5-1.7 (m, 1H), 2.3 (m, 1H) , 2.5 (m, 1 H), 2.7 (m, 1 H), 3.9 (m, 2 H).

Example 9: Preparation of dispersant for rubber composition

Hexadecylsuccinic anhydride and Lauryl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 150 ° C for 5 hours. The unreacted 2-Ethylhexanol was then removed using Vacuum Oven to produce a yellow liquid. (93% yield)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.1-1.4 (m, 46H), 1.55 (m, 2H), 1.6-1.75 (m, 2H), 2.4 (m, 1H) , 2.7 (m, 1 H), 2.8 (m, 1 H), 4.1 (m, 2 H).

Example 10: Preparation of dispersant for rubber composition

Hexadecylsuccinic anhydride and tridecyl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 120 ° C for 5 hours. Then, when the unreacted tridecyl alcohol was removed using Vacuum Oven, a yellow liquid substance was produced. (Yield 95%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.1-1.4 (m, 48H), 1.55 (m, 2H), 1.6-1.75 (m, 2H), 2.4 (m, 1H) , 2.7 (m, 1 H), 2.8 (m, 1 H), 4.1 (m, 2 H).

Example 11: Preparation of dispersant for rubber composition

Hexadecenylsuccinic anhydride and 2-ethylhexanol were placed in a 3-neck round flask at an equivalence ratio (1: 1) and reacted at 180 ° C for 6 hours. The unreacted 2-Ethylhexanol was then removed using a Vacuum Oven to produce an orange liquid. (Yield 95%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 9H), 1.2-1.45 (m, 30H), 1.5 (m, 2H), 1.9 (m, 2H), 2.2 (m, 1H), 2.3 1H), 2.5 (m, 1H), 2.6-2.7 (m, 1H), 3.9 (m, 2H), 5.2 (m,

Example 12: Preparation of dispersant for rubber composition

Hexadecenylsuccinic anhydride and Lauryl alcohol were placed in a 3-neck round flask at an equivalence ratio (1: 1) and reacted at 180 ° C for 6 hours. Thereafter, the unreacted Lauryl alcohol was removed using a Vacuum Oven to form an orange liquid substance. (Yield 95%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 6H), 1.2-1.45 (m, 40H), 1.5 (m, 2H), 1.9 (m, 2H), 2.2 (m, 1H), 2.3 1H), 2.5 (m, 1H), 2.6-2.7 (m, 1H), 2.8 (m, 1H), 4.0 (m, 2H), 5.2 (m,

Example 13: Preparation of dispersant for rubber composition

Hexadecenylsuccinic anhydride and tridecyl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 180 ° C for 6 hours. Thereafter, the unreacted tridecyl alcohol was removed using Vacuum Oven to form an orange liquid substance. (93% yield)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 6H), 1.2-1.4 (m, 42H), 1.5 (m, 2H), 1.9 (m, 2H), 2.2 (m, 1H), 2.3 1H), 2.5 (m, 1H), 2.6-2.7 (m, 1H), 2.9 (m, 1H), 3.9 (m, 2H), 5.3 (m,

Example 14: Preparation of dispersant for rubber composition

Octadecenylsuccinic anhydride and 2-Ethylhexanol were placed in a 3-neck round flask at an equivalence ratio (1: 1) and reacted at 180 ° C for 6 hours. The unreacted 2-Ethylhexanol was then removed using a Vacuum Oven to produce an orange liquid. (Yield 95%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 9H), 1.2-1.4 (m, 34H), 1.5 (m, 2H), 1.9 (m, 2H), 2.2 (m, 1H), 2.3 1H), 2.5 (m, 1H), 2.6-2.7 (m, 1H), 2.9 (m, 1H), 3.9 (m, 2H), 5.3 (m,

Example 15: Preparation of dispersant for rubber composition

Octadecenylsuccinic anhydride and Lauryl alcohol were placed in a 3-neck round flask at an equivalence ratio (1: 1) and reacted at 180 ° C for 6 hours. Thereafter, the unreacted Lauryl alcohol was removed using a Vacuum Oven to form an orange liquid substance. (Yield: 96%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 6H), 1.2-1.4 (m, 44H), 1.5 (m, 2H), 1.9 (m, 2H), 2.2 (m, 1H), 2.3 1H), 2.5 (m, 1H), 2.6-2.7 (m, 1H), 2.9 (m, 1H), 3.9 (m, 2H), 5.3 (m,

Example 16: Preparation of dispersant for rubber composition

Octadecenylsuccinic anhydride and tridecyl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 160 ° C for 6 hours. Thereafter, the unreacted tridecyl alcohol was removed using Vacuum Oven to form an orange liquid substance. (Yield: 96%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 6H), 1.2-1.45 (m, 46H), 1.5 (m, 2H), 1.9 (m, 2H), 2.2 (m, 1H), 2.3 1H), 2.5 (m, 1H), 2.6-2.7 (m, 1H), 2.9 (m, 1H), 3.9 (m, 2H), 5.3 (m,

Example 17: Preparation of dispersant for rubber composition

(2-Dodecen-1-yl) succinic anhydride and 2-ethylhexanol were added to a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 180 ° C for 6 hours. The unreacted 2-Ethylhexanol was then removed using a Vacuum Oven to produce an orange liquid. (93% yield)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 9H), 1.2-1.4 (m, 20H), 1.5 (m, 2H), 2.0 (m, 2H), 2.2 (m, 1H), 2.3 1H), 2.55 (m, 1H), 2.65-2.8 (m, 1H), 2.9 (m, 1H), 4.0 (m, 2H), 5.3 (m,

Example 18: Preparation of dispersant for rubber composition

(2-Dodecen-1-yl) succinic anhydride and Lauryl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 180 ° C for 6 hours. Thereafter, the unreacted Lauryl alcohol was removed using a Vacuum Oven to form an orange liquid substance. (Yield: 96%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.2-1.4 (m, 30H), 1.5 (m, 2H), 2.0 (m, 2H), 2.2 (m, 1H), 2.3 1H), 2.55 (m, 1H), 2.65-2.8 (m, 1H), 2.9 (m, 1H), 4.0 (m, 2H), 5.3 (m,

Example 19: Preparation of dispersant for rubber composition

(2-Dodecen-1-yl) succinic anhydride and tridecyl alcohol were placed in a 3-neck round flask at an equivalent ratio (1: 1) and reacted at 160 ° C for 6 hours. Thereafter, the unreacted tridecyl alcohol was removed using Vacuum Oven to form an orange liquid substance. (Yield: 94%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.2-1.4 (m, 30H), 1.5 (m, 2H), 2.0 (m, 2H), 2.2 (m, 1H), 2.3 1H), 2.55 (m, 1H), 2.65-2.8 (m, 1H), 2.9 (m, 1H), 4.0 (m, 2H), 5.3 (m,

Example 20: Preparation of dispersant for rubber composition

Add 5.06 eq of monoethanolamine to the round flask and drop 1 eq of octadecylsuccinic anhydride at 150 ° C for 1 hour. After that, the reaction is continued for 9 hours, and unreacted monoethanolamine is removed by Evaporator and Vacuum Oven to produce brown solid product. (Yield 89%)

^{1 H NMR (600 MHz, DMSO} ): δ 0.9 (t, 3H), 1.1-1.4 (m, 34H), 2.3 (m, 1H), 2.4 (m, 1H), 2.6 (m, 1H), 3.3 ( t, 2H), 3.4 (t, 2H), 3.6 (m, 4H), 7.8 (t, 2H).

Example 21: Preparation of dispersant for rubber composition

Add 5.06 eq of monoethanolamine to the round flask and drop 1 eq of Dodecylsuccinic anhydride at 150 ° C for 1 hour. The reaction is then continued for 9 hours and unreacted monoethanolamine is removed with an evaporator and vacuum oven to produce a yellow solid product. (Yield: 92%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.1-1.4 (m, 20H), 1.5 (m, 2H), 2.3 (m, 1H), 2.4 (m, 1H), 2.6 (m, 1H), 3.3 (t, 2H), 3.4 (t, 2H), 3.6 (m, 4H), 7.7 (t, 2H).

Example 22: Preparation of dispersant for rubber composition

Monoethanolamine is added to the round flask at 5.06 eq and then 1 eq of hexadecylsuccinic anhydride is added dropwise at 150 ° C for 1 hour. The reaction is then continued for 9 hours and unreacted monoethanolamine is removed with an evaporator and vacuum oven to produce a yellow solid product. (Yield: 94%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.1-1.4 (m, 28H), 1.5 (m, 2H), 2.3 (m, 1H), 2.4 (m, 1H), 2.6 (m, 1H), 3.3 (t, 2H), 3.4 (t, 2H), 3.6 (m, 4H), 7.6 (s, 2H).

Example 23: Preparation of dispersant for rubber composition

Monoethanolamine was added to the round flask at 5.06 eq and then 1 eq of octadecylsuccinic anhydride was dropped at 150 ° C for 1 hour. The reaction is then continued for 9 hours and unreacted monoethanolamine is removed with an evaporator and vacuum oven to produce a yellow solid product. (Yield 98%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.1-1.3 (m, 26H), 2.2 (m, 1H), 2.4 (m, 1H), 2.6 (m, 1H), 2.7 (m, 1 H), 5.4 (m, 1H), 6.7 (m, 2H), 3.7 (m, d, 2H).

Example 24: Preparation of dispersant for rubber composition

Add 0.16 eq of diethanolamine to the round flask and drop 1 eq of hexadecenylsuccinic anhydride for 1 h at 150 ° C. After that, it is reacted for 9 hours and unreacted Diethanolamine is removed by Evaporator and Vacuum Oven to produce black liquid product. (Yield: 94%)

¹ H NMR (600 MHz, CDCl ₃ ):? 0.8 (t, 3H), 1.2-1.3 (m, 24H), 1.9 (m, 9H), 3.6 (m, 12H), 5.2-5.6 (s, 2H).

Example 25: Preparation of dispersant for rubber composition

Add 5.06 eq of diethanolamine to the round flask and drop 1 eq of (2-Dodecen-1-yl) succinic anhydride at 150 ° C for 1 hour. The reaction is then continued for 9 hours and unreacted diethanolamine is removed with an evaporator and vacuum oven to produce a black solid product. (Yield 89%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2-1.3 (m, 28H), 1.9 (m, 2H), 2.3 (m, 1H), 2.6 (m, 1H), 3.4 (m, 9H), 3.6 (m, 12H), 5.2-5.6 (s, 2H).

Example 26: Preparation of dispersant for rubber composition

Add 5.06 eq of diethanolamine to the round flask and drop 1 eq of octadecenylsuccinic anhydride at 150 ° C for 1 hour. The reaction is then continued for 9 hours, and unreacted diethanolamine is removed with an evaporator and vacuum oven to produce a brown solid product. (Yield 85%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2-1.4 (m, 14H), 2.1 (m, 1H), 2.2 (m, 2H), 2.3 (m, 2H), 2.6 (m, 1H), 2.7 (m, 1H), 3.4 (m, 8H), 3.6 (m, 12H), 5.2-5.6 (s, 2H).

Example 27: Preparation of dispersant for rubber composition

Add 5.06 eq of monoethanolamine to the round flask and drop 1 eq of maleic anhydride for 1 hour at 150 ° C. The reaction is then continued for 9 hours, and unreacted Monoethanolamine is removed by Evaporator and Vacuum Oven to yield a brown solid product. (Yield: 84%)

¹ H NMR (600 MHz, CDCl ₃ ):? 3.1 (m, 4H), 3.4 (m, 6H), 6.8 (s, 2H), 8.0 (dm, 2H).

Example 28: Preparation of dispersant for rubber composition

Add monoethanolamine to the round flask at 5.06 eq and drop 1 eq of succinic anhydride at 150 ℃ for 1 hour. The reaction is then continued for 9 hours, and unreacted Monoethanolamine is removed by Evaporator and Vacuum Oven to yield a brown solid product. (Yield 89%)

¹ H NMR (600 MHz, CDCl ₃ ):? 2.3 (s, 4H), 3.1 (m, 4H), 3.4 (m, 6H), 7.8 (t, 2H).

Example 29: Preparation of dispersant for rubber composition

Octadecylsuccinic anhydride and ethylene glycol were added to the flask at a ratio of 2: 1 and reacted at 130 ° C for 6 hours under a nitrogen stream. Unreacted Ethylene glycol is removed by vacuum oven to produce white solid material. (93% yield)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.2-1.4 (m, 64H), 1.5 (m, 2H), 1.6 (m, 2H), 2.-2.65 (m, 2H ), 2.7-2.85 (m, 2H), 2.9 (m, 2H), 4.2-4.5 (m, 4H).

Example 30: Preparation of dispersant for rubber composition

Hexadecylsuccinic anhydride and ethylene glycol were added to the round flask at a ratio of 2: 1 and reacted at 130 ° C for 6 hours under a nitrogen stream. Unreacted Ethylene glycol is removed by vacuum oven to produce white solid material. (Yield: 91%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.2-1.4 (m, 40H), 1.5 (m, 2H), 1.6 (m, 2H), 2.-2.65 (m, 2H ), 2.7-2.85 (m, 2H), 2.9 (m, 2H), 4.2-4.4 (m, 4H).

Example 31: Preparation of dispersant for rubber composition

Dodecylsuccinic anhydride and ethylene glycol were added to the flask at a ratio of 2: 1 and reacted at 130 ° C for 6 hours under a nitrogen stream. Unreacted Ethylene glycol is removed by vacuum oven to produce white solid material. (Yield: 87%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.2-1.4 (m, 56H), 1.5 (m, 2H), 1.6 (m, 2H), 2.5-2.65 (m, 2H) , 2.7-2.85 (m, 2H), 2.9 (m, 2H), 4.1-4.3 (m, 4H).

Example 32: Preparation of dispersant for rubber composition

Hexadecenylsuccinic anhydride and ethylene glycol were added to the round flask at a ratio of 2: 1 and reacted at 130 ° C for 6 hours under a nitrogen stream. Unreacted Ethylene glycol is removed by vacuum oven to produce white solid material. (Yield: 91%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.2-1.4 (m, 48H), 2.0 (m, 4H), 2.25 (m, 1H), 2.4 (m, 1H), 2.5 (m, 1H), 2.7 (m, 1H), 2.9 (m, 2H), 4.3 (m, 4H), 5.3 (m, 2H), 5.5 (m, 2H).

Example 33: Preparation of dispersant for rubber composition

(2-Dodecen-1-yl) succinic anhydride and ethylene glycol were added to the flask at a ratio of 2: 1 and reacted at 130 ° C for 6 hours under a nitrogen stream. Unreacted Ethylene glycol is removed by vacuum oven to produce white solid material. (Yield: 91%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 6H), 1.2-1.4 (m, 28H), 2.0 (m, 2H), 2.2 (m, 4H), 2.4 (m, 2H), 2.5 (m, 2H), 2.6 (m, 2H), 2.8 (m, 2H), 4.3 (m, 4H), 5.3 (m, 2H), 5.5 (m, 2H).

Example 34: Preparation of dispersant for rubber composition

(2-Dodecen-1-yl) succinic anhydride and diethylene glycol are added to the flask at a ratio of 2: 1 and reacted at 130 ° C for 6 hours under a nitrogen stream. Removal of unreacted diethylene glycol using Vacuum Oven produces a white solid material. (Yield: 94%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 6H), 1.1-1.3 (m, 28H), 1.9 (m, 2H), 2.1 (m, 4H), 2.3 (m, 2H), 2.5 (m, 2H), 2.6 (m, 2H), 2.7-2.9 (m, 2H), 3.5 (t, 4H), 4.1-4.3 ).

Example 35: Preparation of dispersant for rubber composition

Succinic anhydride and ethylene glycol were added to the round flask at a ratio of 2: 1 and reacted at 130 ° C for 6 hours under a nitrogen stream. Unreacted Ethylene glycol is removed by vacuum oven to produce white solid material. (93% yield)

¹ H NMR (600 MHz, CDCl ₃ ):? 2.45 (m, 4H), 2.55 (m, 4H), 4.2 (s, 4H).

Example 36: Preparation of dispersant for rubber composition

Succinic anhydride and diethylene glycol are added to the round flask at a ratio of 2: 1 and reacted at 130 ° C for 6 hours under a nitrogen stream. Removal of unreacted diethylene glycol using Vacuum Oven produces a white solid material. (Yield: 94%)

^{1 H NMR (600 MHz, CDCl} 3): δ 2.7 (m, 8H), 3.7 (t, 4H), 4.3 (t, 4H).

Example 37: Preparation of dispersant for rubber composition

Maleic anhydride and ethylene glycol were added to the round flask at a ratio of 2: 1 and reacted at 130 ° C for 6 hours under a nitrogen stream. Unreacted Ethylene glycol is removed by vacuum oven to produce white solid material. (Yield: 90%)

^{1 H NMR (600 MHz, CDCl} 3): δ 3.7 (m, 4H), 4.3 (m, 4H), 6.2 (m, 4H).

Example 38: Preparation of dispersant for rubber composition

(2-Dodecen-1-yl) succinic anhydride and ethylene glycol monomethyl ether were added in a ratio of 1: 1 and reacted at 130 ° C for 3 hours in a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow liquid material is produced. (Yield 90%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 3H), 1.2-1.4 (m, 14H), 2.0 (t, 2H), 2.3 (m, 1H), 2.4 (m, 1H), 2.5 2H), 5.3 (m, 1H), 5.5 (m, 1H), 2.8 (m, m, 1H).

Example 39: Preparation of dispersant for rubber composition

Hexadecenylsuccinic anhydride and ethylene glycol monomethyl ether were added to the flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. Removal of unreacted material using an evaporator produces a yellow semi solid material. (Yield 91%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 3H), 1.2-1.4 (m, 24H), 2.0 (t, 2H), 2.4 (m, 1H), 2.6 (m, 1H), 3.0 (m, 1H), 3.4 (s, 3H), 3.6 (t, 2H), 4.3 (m, 2H), 5.3 (m,

Example 40: Preparation of dispersant for rubber composition

Octadecenylsuccinic anhydride and ethylene glycol monomethyl ether were added to the flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow solid material is produced. (Yield 92%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 3H), 1.2-1.4 (m, 28H), 2.0 (t, 2H), 2.5 (m, 1H), 2.7 (m, 1H), 3.0 (m, 1H), 3.4 (s, 3H), 3.6 (t, 2H), 4.3 (m, 2H), 5.3 (m,

Example 41: Preparation of dispersant for rubber composition

Dodecylsuccinic anhydride and ethylene glycol monomethyl ether were added to the flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow solid material is produced. (Yield 90%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 3H), 1.2-1.4 (m, 20H), 1.5 (t, 1H), 1.7 (m, 1H), 2.5 (m, 1H), 2.8 (m, 1H), 2.9 (m, 1H), 3.4 (s, 3H), 3.6 (t, 2H), 4.3 (m, 2H).

Example 42: Preparation of dispersant for rubber composition

Hexadecylsuccinic anhydride and ethylene glycol monomethyl ether were added to the flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow solid material is produced. (Yield 89%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 3H), 1.2-1.4 (m, 28H), 1.5 (t, 1H), 1.7 (m, 1H), 2.4 (m, 1H), 2.7 (m, 1H), 2.9 (m, 1H), 3.4 (s, 3H), 3.6 (t, 2H), 4.3 (m, 2H).

Example 43: Preparation of dispersant for rubber composition

Octadecylsuccinic anhydride and ethylene glycol monomethyl ether were added to the flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow solid material is produced. (Yield 91%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2-1.4 (m, 32H), 1.5 (m, 1H), 1.7 (m, 1H), 2.4 (m, 1H), 2.7 (m, 1H), 2.8 (m, 1H), 3.3 (s, 3H), 3.6 (t, 2H), 4.2 (m, 2H).

Example 44: Preparation of dispersant for rubber composition

(2-Dodecen-1-yl) succinic anhydride and diethylene glycol monomethyl ether in a ratio of 1: 1, and reacted at 130 ° C for 3 hours in a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow liquid material is produced. (Yield 89%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2-1.4 (m, 14H), 1.9 (m, 2H), 2.2 (m, 1H), 2.4 (m, 1H), 2.6 (m, 1H), 2.9 (m, 1H), 3.3 (s, 3H), 3.5-3.7 (m, 10H), 4.2 (m, 2H), 5.3 (m,

Example 45: Preparation of dispersant for rubber composition

Hexadecenylsuccinic anhydride and diethylene glycol monomethyl ether were added to the round flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. Removal of unreacted material using an evaporator produces a yellow semi solid material. (Yield 91%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2-1.4 (m, 24H), 2.0 (t, 2H), 2.4 (m, 1H), 2.6 (m, 1H), 3.0 (m, 1H), 3.4 (s, 3H), 3.5-3.7 (m, 10H), 4.3 (m, 2H), 5.3 (m,

Example 46: Preparation of dispersant for rubber composition

Octadecenylsuccinic anhydride and diethylene glycol monomethyl ether were added to the round flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow solid material is produced. (Yield 91%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2-1.4 (m, 28H), 2.0 (t, 2H), 2.4 (m, 1H), 2.6 (m, 1H), 3.0 (m, 1H), 3.4 (s, 3H), 3.5-3.7 (m, 10H), 4.3 (m, 2H), 5.3 (m,

Example 47: Preparation of dispersant for rubber composition

Dodecylsuccinic anhydride and diethylene glycol monomethyl ether were added to the flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow solid material is produced. (Yield 88%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 3H), 1.2-1.4 (m, 20H), 1.5 (t, 1H), 1.7 (m, 1H), 2.5 (m, 1H), 2.8 (m, 1H), 2.9 (m, 1H), 3.4 (s, 3H), 3.5-3.7 (m, 10H), 4.3 (m, 2H).

Example 48: Preparation of dispersant for rubber composition

Hexadecylsuccinic anhydride and diethylene glycol monomethyl ether were added to the flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow solid material is produced. (Yield 89%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.9 (t, 3H), 1.2-1.4 (m, 28H), 1.5 (t, 1H), 1.7 (m, 1H), 2.4 (m, 1H), 2.7 (m, 1H), 2.9 (m, 1H), 3.4 (s, 3H), 3.5-3.7 (m, 10H), 4.3 (m, 2H).

Example 49: Preparation of dispersant for rubber composition

Octadecylsuccinic anhydride and diethylene glycol monomethyl ether are added to the round flask at a ratio of 1: 1 and reacted at 130 ° C for 3 hours under a nitrogen stream. When the unreacted material is removed using an evaporator, a yellow solid material is produced. (Yield 93%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2-1.4 (m, 32H), 1.5 (m, 1H), 1.7 (m, 1H), 2.4 (m, 1H), 2.7 (m, 1H), 2.8 (m, 1H), 3.3 (s, 3H), 3.5-3.7 (m, 10H), 4.2 (m, 2H).

Example 50: Preparation of dispersant for rubber composition

Maleic anhydride (MA) and hexadecanol are added to the round flask at a ratio of 1: 1 and reacted at 80 ° C for 1 hour. Heptane is then added to the Mixture and stirred at 80 ° C for 15 minutes. Thereafter, the mixture was stirred at room temperature for 3 hours, cooled to 15 ° C and stirred for 15 minutes. Then a white solid is formed and a filter is produced. (Yield: 86%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2-1.4 (m, 26H), 1.6 (m, 2H), 4.2 (t, 2H), 6.3 (d, 1H), 6.4 (d, 1 H).

Example 51: Preparation of dispersant for rubber composition

Maleic anhydride (MA) and octadecanol were added to the round flask at a ratio of 1: 1 and reacted at 80 ° C for 1 hour. Heptane is then added to the Mixture and stirred at 80 ° C for 15 minutes. Thereafter, the mixture was stirred at room temperature for 3 hours, cooled to 15 ° C and stirred for 15 minutes. Then a white solid is formed and a filter is produced. (Yield 85%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.1-1.3 (m, 30H), 1.7 (m, 2H), 4.2 (t, 2H), 6.3 (d, 1H), 6.4 (d, 1 H).

Example 52: Preparation of dispersant for rubber composition

Succinic anhydride (SA) and dodecylamine are mixed in a ratio of 1.1: 1 in a round flask and dissolved in methylene chloride (MC). After that, triethylamine is added at 1.82 times at room temperature. The mixture was stirred for 3 hours, concentrated using an evaporator, and recrystallized from acetone to yield a white solid. (Yield: 87%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2 (m, 18H), 1.4 (m, 2H), 2.4 (t, 2H), 2.6 (t, 2H), 3.2 (t , ≪ / RTI > 2H), 5.8 (s, 1H).

Example 53: Preparation of dispersant for rubber composition

Add succinic anhydride (SA) and hexadecylamine to the round flask at a ratio of 1.1: 1 and dissolve in methylene chloride (MC). After that, triethylamine is added at 1.82 times at room temperature. The mixture was stirred for 3 hours, concentrated using an evaporator, and recrystallized from acetone to yield a white solid. (Yield: 90%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2 (m, 26H), 1.4 (m, 2H), 2.2 (t, 2H), 2.4 (t, 2H), 3.0 (t , ≪ / RTI > 2H), 7.8 (s, 1H).

Example 54: Preparation of dispersant for rubber composition

Succinic anhydride (SA) and octadecylamine are added to the round flask at a ratio of 1.1: 1 and dissolved in methylene chloride (MC). After that, triethylamine is added at 1.82 times at room temperature. The mixture was stirred for 3 hours, concentrated using an evaporator, and recrystallized from acetone to yield a white solid. (Yield: 86%)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.2-1.4 (m, 32H), 2.3 (t, 2H), 2.4 (t, 2H), 3.0 (t, 2H), 7.8 (s, 1 H).

Example 55: Preparation of dispersant for rubber composition

Maleic anhydride (MA, 1 eq) is dissolved in MC in a round flask and Dodecylamine (1 eq) dissolved in MC is slowly added dropwise in ice. After completion of dropwise addition, the mixture is stirred for 20 minutes. Then, it is filtered using ICE MC to produce white matter. (97% yield)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.1-1.3 (m, 18H), 1.5 (t, 2H), 3.3 (t, 2H), 6.2 (d, 1H), 6.4 (d, 1 H), 7.6 (s, 1 H).

Example 56: Preparation of dispersant for rubber composition

Maleic anhydride (MA, 1 eq) is dissolved in MC in a round flask and Hexadecylamine (1 eq) dissolved in MC is slowly added dropwise in iced state. After completion of dropwise addition, the mixture is stirred for 20 minutes. Then, it is filtered using ICE MC to produce white matter. (97% yield)

^{1 H NMR (600 MHz, CDCl} 3): δ 0.8 (t, 3H), 1.1-1.3 (m, 26H), 1.5 (t, 2H), 3.3 (t, 2H), 6.2 (d, 1H), 6.3 (d, 1 H), 6.8 (s, 1 H).

Example 57: Preparation of dispersant for rubber composition

Maleic anhydride (MA, 1 eq) is dissolved in MC in a round flask and then octadecylamine (1 eq) dissolved in MC is slowly added dropwise in ice. After completion of dropwise addition, the mixture is stirred for 20 minutes. Then, it is filtered using ICE MC to produce white matter. (Yield: 96%)

Example 58: Preparation of dispersant for rubber composition

Ethylene glycol monomethyl ether is added to succinic anhydride in a ratio of 1: 1 and reacted for 4 hours under a nitrogen stream at 130 ° C. Removal of unreacted material using evaporator generates yellow material. (Yield: 75%)

^{1 H NMR (600 MHz, CDCl} 3): δ 2.7 (m, 4H), 3.4 (s, 3H), 3.6 (t, 2H), 4.3 (t, 2H).

Example 59: Preparation of dispersant for rubber composition

Diethylene glycol monomethyl ether is added to succinic anhydride in a ratio of 1: 1 and reacted for 4 hours under a nitrogen stream at 130 ° C. Removal of unreacted material using evaporator generates yellow material. (Yield: 76%)

^{1 H NMR (600 MHz, CDCl} 3): δ 2.7 (s, 4H), 3.4 (s, 3H), 3.6 (t, 2H), 3.65 (t, 2H), 3.7 (t, 2H), 4.3 (m , 2H).

Example 60: Preparation of dispersant for rubber composition

Diethylene glycol monomethyl ether was added to maleic anhydride in a ratio of 1: 1 and reacted for 4 hours under a nitrogen stream at 130 ° C. Removal of unreacted material using evaporator generates yellow material. (Yield: 78%)

^{1 H NMR (600 MHz, CDCl} 3): δ 3.3 (m, 3H), 3.5 (m, 2H), 3.6 (m, 2H), 3.7 (m, 2H), 4.3 (m, 2H), 6.1 (m , ≪ / RTI > 1H), 6.2 (m, 1H).

Example 61: Preparation of dispersant for rubber composition

Ethylene glycol monomethyl ether was added to maleic anhydride in a ratio of 1: 1 and reacted for 4 hours under a nitrogen stream at 130 ° C. Removal of unreacted material using evaporator generates yellow material. (Yield: 74%)

^{1 H NMR (600 MHz, CDCl} 3): δ 3.3 (d, 3H), 3.6 (t, 2H), 4.3 (m, 2H), 6.2 (m, 2H).

Example 62: Preparation of dispersant for rubber composition

Succinic anhydride (20.01 g, 0.2 mol) and dodecanol (37.27 g, 0.2 mol) were refluxed in 100 ml of toluene for 7 hours. When the reaction was completed, 100 ml of water and 100 ml of dichloromethane were added to separate the organic layer, and the aqueous layer was washed twice with 100 ml of dichloromethane. The combined organic layers were dried over magnesium sulfate and the organic solvent was evaporated. As a result, a white solid was obtained. (Yield: 96%)

_{^{1 H-NMR (CDCl 3)}} : δ 0.81 (t, 3H), 1.25 (m, 18H), 1.55 (m, 2H), 2.54 (m, 2H), 2.61 (m, 2H), 4.01 (m, 2H )

Example 63: Preparation of dispersant for rubber composition

Succinic anhydride (20.01 g, 0.2 mole) and hexadecanol (48.49 g, 0.2 mole) were refluxed in 100 ml of toluene for 7 hours. When the reaction is completed and cooled to room temperature, a solid is produced. 100 ml of water and 100 ml of dichloromethane are added to dissolve the solid. The organic layer is separated and the water layer is washed twice with 100 ml of dichloromethane. The combined organic layers were dried over magnesium sulfate and the organic solvent was evaporated. As a result, a white solid was obtained. (Yield 95%)

_{^{1 H-NMR (CDCl 3)}} : δ 0.90 (t, 3H), 1.33 (m, 26H), 1.64 (m, 2H), 2.65 (m, 2H), 2.71 (m, 2H), 4.11 (m, 2H )

Example 64: Preparation of dispersant for rubber composition

Succinic anhydride (20.01 g, 0.2 mole) and octadecanol (54.10 g, 0.2 mole) were refluxed in 100 ml of toluene for 7 hours. When the reaction is completed and cooled to room temperature, a solid is produced. 100 ml of water and 100 ml of dichloromethane are added to dissolve the solid. The organic layer is separated and the water layer is washed twice with 100 ml of dichloromethane. The combined organic layers were dried over magnesium sulfate and the organic solvent was evaporated. As a result, a white solid was obtained. (Yield: 91%)

_{^{1 H-NMR (CDCl 3)}} : δ 0.91 (t, 3H), 1.34 (m, 30H), 1.64 (m, 2H), 2.64 (m, 2H), 2.71 (m, 2H), 4.11 (m, 2H )

Example 65: Preparation of dispersant for rubber composition

Maleic anhydride (24.6 g, 0.25 mol) and dodecanol (46.59 g, 0.25 mol) were heated to 80 ^° C while being slowly dissolved for 1 hour. 75 ml of heptane was added and the mixture was heated at 80 ^° C for 15 minutes. The mixture was stirred at room temperature for 5 hours, and then crystallized in a refrigerator to obtain a white solid. (Yield 60%).

_{^{1 H-NMR (CDCl 3)}} : δ 0.90 (t, 3H), 1.35 (m, 18H), 1.74 (m, 2H), 4.30 (t, 2H), 6.40 (d, 2H), 6.48 (d, 2H )

Comparative Example 1:

Comparative Example 1 was a commercially available dispersant (trade name: SDA-21G; zinc content: 8.3 wt%) containing a zinc component.

Production Example: Production of rubber composition (rubber molded article)

Each component of CMB (Carbon Black Masterbatch) shown in the following Table 1 was formulated using a DJ-05 Kneader manufactured by Public Precision Co., Ltd. Subsequently, the CMB was dispersed and sheet-formed using a roll of DJ-6 * 14 manufactured by Public Precision Co., Ltd.

Then, each component of the FMB (final masterbatch) shown in Table 1 below was further mixed and crosslinked (vulcanized) by pressurization and heat treatment while using a KD HP 152 press machine manufactured by Kukdong Machinery Co., Ltd. to produce a rubber molded article (specimen).

The kneader temperature, the mixing time at the kneader, and the running conditions such as rolls are as shown in Table 1 below, and the pressurized heat treatment conditions are summarized in the respective curing conditions shown in Table 2 below.

division division Ingredients content
(Parts by weight) Kneader temperature Mixing time role CMB Synthetic rubber
Isobutylene isoprene rubber (IIR) 25.00 Setting:
80 ℃ 0'00 " Triangle
(7/7) Bromo isobutylene isoprene rubber (Br-IIR) 25.00 Butadiene rubber (BR) 30.00 Natural rubber Standard rubber (SVR-3L) 20.00 Silica Zeosil 175GR 58.00 3'00 " Carbon black N220 0.50 Process oil Paraffin oil (P # 2) 5.00 Tackifier 11.00 7'00 " Silane coupling agent Bis-3-triethoxysilylpropyl-tetra-sulfide (Si-69) 4.00 fatty acid Stearic acid 1.00 11'00 " Antioxidant 1.00 Dispersant Comparative Example 1, Examples 13, 14, 23, 39, or 41 2.00 Sum 182.50 Dump: 15'00 " FMB CMB 182.50 Setting: 60 ℃ 0'00 " Triangle
(5/5) Crosslinking auxiliary Zinc oxide (ZnO) 5.00 1'30 " Crosslinking accelerator Mercaptobenzothiazole 0.70 Dibenzothiazole disulfide (DM) 1.25 Tetramethylthiuram monosulfide (TS) 0.13 Cross-linking agent Insoluble sulfur (IS) 2.50 Sum 192.08 Dump: 5'00 "

Test Example : Evaluation of physical properties of rubber composition (rubber molding)

The physical properties of the rubber composition obtained in the above Production Examples were evaluated by the following methods.

1. Mooney viscosity and scorch time (T ₅ ): Mooney viscometer (DMV-200C) manufactured by Daegu Engineering Co., Ltd.

2. Rheological properties (T ₉₀ , Tmax, Tmin): Measured according to ASTM 2240-93 using a Rheometer (DRM-100) manufactured by DAIKYE ENGINEERING CO., LTD.

3. Hardness: Measured according to KS M-6518, using a Shore A (Black Asker) from Asuka.

4. Mechanical Properties (Tensile Strength, Modulus, Elongation, Tear Strength): Measured according to KS M-6518 using a tensile compression tester (DUT-500CM)

5. Abrasion resistance: NBS Abrasion tester (WL210N) manufactured by Weed Lab Co., Ltd. was used and measured according to KS M 6625.

The results of the physical property evaluation are summarized in Table 2 below.

Dispersant T ₅ T ₉₀ Rheological properties Hardness Seal
burglar Modulus
(100%) Elongation Tear
burglar Abrasion resistance T _max T _min ΔMH Minutes: seconds Minutes: seconds lb-in A type kgf / cm ² kgf / cm ² % kgf / cm NBS,% Primary test Measuring conditions:
155 ^o C, 12 min Crosslinking conditions: 155 ℃, 8min, 150kgf / cm 2 Comparative Example 1 01:52 07:08 31.9 13.0 18.9 61 114.37 19.39 534.55 46.91 145.78 Example 13 01:46 07:27 31.9 13.8 18.1 63 111.62 24.59 466.70 46.80 145.61 Example 14 01:52 07:41 31.2 13.4 17.8 60 106.48 20.16 554.53 46.27 153.33 Example 23 01:55 07:11 31.8 12.8 19.0 63 117.78 24.01 488.53 45.81 145.35 Secondary test Measuring conditions:
155 ^o C, 12 min Crosslinking conditions: 155 ℃, 8min, 150kgf / cm 2 Comparative Example 1 01:56 06:54 33.2 16.1 17.1 64 124.10 23.98 596.13 62.15 205.76 Example 39 02:02 06:49 33.1 16.1 17.0 66 135.32 19.01 725.20 63.33 233.33 Example 41 02:05 06:30 34.2 15.9 18.3 63 135.09 20.80 639.03 62.33 231.48

Referring to Table 2 above, it was confirmed that the rubber composition obtained by using the dispersant of the examples exhibited mechanical properties equal to or higher than those of Comparative Example without the use of the dispersant of Comparative Example containing a heavy metal component.

Claims (9)

Dispersant for rubber composition comprising a compound of formula
[Chemical Formula 1]

In Formula 1,
X is a ₂ -OR1, -NHR1, or -N (R1),
Y is -OR2, -NHR2, or -N (R2) ₂ ,
R 1 and R 2 are each independently selected from the group consisting of hydrogen, an alkyl group having 5 to 30 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, or - (CH ₂ -CH ₂ -O) m -R 3,
R3 is hydrogen, an alkyl group having 1 to 5 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, or

ego,
R is hydrogen, an alkyl group having 10 to 30 carbon atoms, a vinyl group or an alkenyl group having 10 to 30 carbon atoms,
The dotted line indicates that there may or may not be a double bond, m is an integer of 1 to 3,
And at least one of R1 and R2 is hydrogen when X and Y are different from each other, -OR1 and -OR2.
The method of claim 1, wherein the alkenyl group of the carbon number of 10 to 30 group is -CH ₂ -CH = CH-R4 dispersants for rubber compositions represented by (R4 is an alkyl group having 7 to 27).
The compound of claim 1, wherein X and Y are the same or different,
X and Y are different from each other, and at least one of X and Y is -OH.
2. The rubber composition according to claim 1, wherein the compound of formula (1) is selected from the group consisting of:

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The dispersant for rubber composition according to claim 1, wherein the silica-based reinforcing agent contained in the rubber composition is dispersed.
Rubber; Silica-based reinforcing agents; And a dispersant according to claim 1.
7. The rubber composition according to claim 6, wherein the rubber comprises at least one of natural rubber and synthetic rubber.
The rubber composition according to claim 6, further comprising at least one additive selected from the group consisting of carbon black, a silane coupling agent, a process oil, a tackifier, a fatty acid, a crosslinking agent, a crosslinking assistant and a crosslinking accelerator.
 The rubber composition according to claim 6, which is used for producing a rubber for shoe sole.