CN112063100A - Modified resin liquid and preparation method thereof - Google Patents
Modified resin liquid and preparation method thereof Download PDFInfo
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- CN112063100A CN112063100A CN202010963247.9A CN202010963247A CN112063100A CN 112063100 A CN112063100 A CN 112063100A CN 202010963247 A CN202010963247 A CN 202010963247A CN 112063100 A CN112063100 A CN 112063100A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C08L57/02—Copolymers of mineral oil hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/06—Waxes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
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Abstract
The invention discloses a modified resin liquid and a preparation method thereof, wherein the preparation method of the modified resin liquid comprises the following steps: (1) dissolving the resin R in the dissolved oil 01, and fully melting and dispersing; (2) adding a catalyst L and continuously stirring uniformly; (3) adding a modifier B, and modifying under heating and stirring; (4) and after the modification is finished, adding an acid-base regulator, and regulating the reaction liquid to be neutral to obtain the modified resin liquid. The polycyclic aromatic hydrocarbon content of the modified resin liquid provided by the invention is very low, the modified resin liquid can be directly used for blending with raw oil to prepare rubber oil, and the prepared rubber oil has good compatibility with rubber while the polycyclic aromatic hydrocarbon content meets European Union standards; the method has the advantages of rich used raw materials, simple process, low cost and convenient industrial popularization.
Description
Technical Field
The invention belongs to the technical field of rubber industry, relates to processing of rubber oil, and particularly relates to a modified resin liquid for preparing rubber oil by blending and a preparation method thereof.
Background
The rubber oil is a processing aid used in the production process of rubber products, can obviously improve the processing performance of rubber, and the performance of the rubber oil directly influences the quality of the rubber products. In the past, domestic rubber oil is mainly unrefined or low-refined mineral oil, and is mostly a byproduct high aromatic hydrocarbon extract oil of an oil refinery, and is mainly used for tire production. Aromatic oil has good compatibility with rubber and can endow tires with excellent performances such as good wet skid resistance and the like, and is widely applied to oil-filled rubber and tire enterprises at home and abroad, but along with the deep research on the toxicity of developed countries at home and abroad, the aromatic oil contains carcinogenic polycyclic aromatic hydrocarbon (PCA), so that the problem of harm to human bodies and the environment is accepted by the public. According to the release of international authority: a significant number of lung cancer patients in the world are caused by inhalation of automobile tire powder. PCA not only has toxic and carcinogenic effects, but also easily discolors rubber products and affects the quality of the rubber products. Therefore, the eu environmental regulations stipulate that, since 1/2010, all rubber extender oils entering the eu market must fully meet the eu 2005/69/EC standard, i.e. the rubber oil has a polycyclic aromatic content of less than 3, 8 specific aromatic contents of less than 10mg/kg, and a benzopyrene content of less than lmg/kg. Furthermore, according to REACH regulations, the total PAHs content in the tyre should be less than 0.1 of the mass of the tyre. At present, aromatic hydrocarbon-based rubber filling oil meeting the specification of European Union 2005/69/EC is basically monopolized by German Hansheng company and is expensive, so that the production and application of aromatic hydrocarbon-based rubber oil substitutes attract extensive attention in the industry.
At present, the preparation method of the environment-friendly rubber oil mainly comprises two schemes of solvent refining and hydrotreating. Solvent refining is a technology for removing harmful or non-ideal components in oil materials by utilizing the selective dissolving capacity of a solvent, for example, CN200910088932.5 and CN201010228871.0 are used for obtaining environment-friendly rubber oil by the method; although the solvent refining can ensure the content of aromatic hydrocarbon, the solvent refining needs to be carried out for many times to remove the polycyclic aromatic hydrocarbon in the rubber oil, so that the product yield is lower; in addition, multiple steps of mixing, extracting, steam stripping, flash evaporation and the like are required for refining, so that the processing cost is high; the hydrotreating refers to the catalytic hydrogenation to convert non-ideal components into ideal components or micromolecular hydrocarbons to achieve the purpose of removing, and in addition, the olefin and the dialkene are subjected to hydrogenation saturation, the aromatic hydrocarbon is subjected to partial hydrogenation saturation, and the quality of the oil product is improved. But the hydrotreating process results in a large loss of aromatic hydrocarbon content, and poor compatibility between rubber oil and rubber. Therefore, in order to ensure that the rubber oil has a certain aromatic hydrocarbon content, the hydrogenation treatment and the solvent refining are combined to produce the environment-friendly rubber oil, but the treatment procedure is complicated, the cost is high, and the finished product still contains 8 Polycyclic Aromatic Hydrocarbons (PAHs).
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide the modified resin liquid which can be used for preparing the rubber oil by blending, the polycyclic aromatic hydrocarbon content of the modified resin liquid is very low, the modified resin liquid can be directly used for preparing the rubber oil by blending with raw oil, and the prepared rubber oil has good compatibility with rubber while the polycyclic aromatic hydrocarbon content meets the European Union standard; the invention also aims to provide a preparation method of the modified resin liquid, which has the advantages of abundant raw materials, simple process, low cost and convenient industrial popularization.
The invention is realized by the following technical scheme:
a preparation method of modified resin liquid comprises the following steps:
(1) dissolving the resin R in the dissolved oil 01, and fully melting and dispersing;
(2) adding a catalyst L and continuously stirring uniformly;
(3) adding a modifier B, and modifying under heating and stirring;
(4) and after the modification is finished, adding an acid-base regulator, and regulating the reaction liquid to be neutral to obtain the modified resin liquid.
The invention further improves the scheme as follows:
further, the resin R is a low molecular weight polymer petroleum resin or a natural resin.
The resin R is one or more of C9 resin, C5 resin, dicyclopentadiene resin and monomer thereof, alpha-methyl styrene homopolymerization resin or monomer, copolymer resin based on alpha-methyl styrene as a main chain, terpene resin, pinene resin, asphalt or conpa resin.
Further, the dissolved oil 01 is one or a mixture of two or more of aromatic hydrocarbon-based oil, naphthenic oil, and paraffinic oil.
Further, detecting the content of benzo (a) pyrene in the dissolved oil 01 by polycyclic aromatic hydrocarbon to be 0-50 ppm; the total content of PAHs in benzo (a) pyrene, benzo (e) pyrene, benzo (a) anthracene, chrysene, benzo (b) fluoranthene, benzo (j) fluoranthene, benzo (k) fluoranthene and dibenzo (a, h) anthracene 8 is 0-1000 ppm.
Further, the catalyst L is AlCl3、FeCl3、H2SO4、H3PO4、BF3、BF3One or more of a complex and HF.
Further, the modifier B is one or a mixture of more than two of phenol, cardanol, m-cresol, bornylene, ethylidene norbornene, dicyclopentadiene, coumarone resin, hexamethoxy melamine resin, furfural, divinylbenzene, p-benzhydrol or paraformaldehyde.
Further, the mass ratio of the resin R, the dissolved oil 01, the modifier B and the catalyst L is 30-50: 20-70: 1-5: 0.1-0.8, and the acid-base regulator is one or the mixture of more than two of hexamethylene diamine, ethylene diamine or triethylamine.
Further, the melting temperature is 100-120 ℃, the modification temperature is 100-120 ℃, and the modification time is 2-4 h.
The invention further improves the scheme as follows:
a modified resin liquid is prepared by the preparation method.
The invention has the beneficial effects that:
the modified resin liquid prepared by the invention has the benzo (a) pyrene content lower than 3 ppm; benzo (a) pyrene, benzo (e) pyrene, benzo (a) anthracene, chrysene, benzo (b) fluoranthene, benzo (j) fluoranthene, benzo (k) fluoranthene, dibenzo (a, h) anthracene 8 item PAHs content is less than 30 ppm.
In the preparation method of the modified resin liquid, the modifier is utilized to promote the conversion of 8 kinds of high carcinogenic polycyclic aromatic hydrocarbons in the presence of the catalyst, so that the polycyclic aromatic hydrocarbons are subjected to alkylation or condensation reaction, and the content of 8 PAHs in the modified resin liquid is reduced.
The invention has simple production process and low cost, is convenient for industrialized popularization and simultaneously improves the operation safety; the used raw materials are convenient to recover, and the environmental pollution is reduced; the used raw materials have rich resources and low price.
Detailed Description
Example 1
1. In a four-neck flask, 800g C9 resin is dissolved in 400g of naphthenic oil KN4006, and the resin is melted at the temperature of 100 ℃ and 120 ℃;
2. 4.8g AlCl is added into the reaction system3Catalyst, after stirring for half an hour;
3. adding 40g of phenol, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. adding hexamethylene diamine into the reaction liquid, and adjusting the reaction liquid to be neutral to obtain the modified resin liquid.
Example 2
1. In a four-neck flask, 600g of asphalt resin is dissolved in 400g of naphthenic oil KN4006, and the mixture is melted at the temperature of 100 ℃ and 120 ℃;
2. adding 4g of boron trifluoride diethyl etherate catalyst into the reaction system, and stirring for half an hour;
3. adding 40g of phenol and 40g of coumarone resin, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. adding ethylenediamine into the reaction liquid, and adjusting the reaction liquid to be neutral to obtain the modified resin liquid.
Example 3
1. In a four-neck flask, 400g of asphalt resin is dissolved in 400g of naphthenic oil KN4010, and the melting is kept at the temperature of 100 ℃ and 120 ℃;
2. 4g of p-toluenesulfonic acid catalyst is added into the reaction system, and the mixture is stirred for half an hour;
3. adding 60g of cardanol, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. and adding triethylamine into the reaction solution, and adjusting the reaction solution to be neutral to obtain the modified resin solution.
Example 4
1. In a four-neck flask, 400g C5 resin is dissolved in 400g of naphthenic oil KN4006, and the resin is melted at the temperature of 100 ℃ and 120 ℃;
2. 3g of FeCl was added to the reaction system3Catalyst, after stirring for half an hour;
3. adding 40g of m-cresol, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. adding hexamethylene diamine into the reaction liquid, and adjusting the reaction liquid to be neutral to obtain the modified resin liquid.
Example 5
1. In a four-neck flask, 700g of asphalt resin is dissolved in 300g of aromatic oil, and the melting is maintained at the temperature of 100 ℃ and 120 ℃;
2. 1.6g of H was added to the reaction system2SO4Catalyst, after stirring for half an hour;
3. adding 40g of bornylene, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. adding hexamethylene diamine into the reaction liquid, and adjusting the reaction liquid to be neutral to obtain the modified resin liquid.
Example 6
1. 300g of dicyclopentadiene resin and 300g C9 resin are dissolved in 400g of naphthenic oil 4010 in a four-neck flask, and the solution is melted at the temperature of 100 ℃ and 120 ℃;
2. 4g of H was added to the reaction system3PO4Catalyst, after stirring for half an hour;
3. adding 40g of phenol and 40g of dicyclopentadiene, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. adding ethylenediamine into the reaction liquid, and adjusting the reaction liquid to be neutral to obtain the modified resin liquid.
Example 7
1. In a four-neck flask, 400g of dicyclopentadiene resin and 100g of asphalt resin are dissolved in 200 g of aromatic hydrocarbon-based oil, and the mixture is melted at the temperature of 100 ℃ and 120 ℃;
2. adding 4g of boron trifluoride diethyl etherate catalyst into the reaction system, and stirring for half an hour;
3. adding 80g of p-diphenylmethanol, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. and adding triethylamine into the reaction solution, and adjusting the reaction solution to be neutral to obtain the modified resin solution.
Example 8
1. 300g of dicyclopentadiene resin and 300g C9 resin were dissolved in 400g of naphthenic oil KN4010 in a four-necked flask, and melted at 100 ℃ and 120 ℃;
2. adding 4g of HF catalyst into the reaction system, and stirring for half an hour;
3. adding 40g of phenol and 40g of coumarone resin, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. adding hexamethylene diamine into the reaction liquid, and adjusting the reaction liquid to be neutral to obtain the modified resin liquid.
Example 9
1. In a four-neck flask, 400g of conpa resin was dissolved in 400g of paraffinic oil and was melted at 100 ℃ and 120 ℃;
2. 4g of p-toluenesulfonic acid catalyst is added into the reaction system, and the mixture is stirred for half an hour;
3. adding 40g of phenol and 20g of hexamethoxy melamine resin, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. adding hexamethylene diamine into the reaction liquid, and adjusting the reaction liquid to be neutral to obtain the modified resin liquid.
Example 10
1. In a four-neck flask, 400g of asphalt resin is dissolved in 400g of paraffin-based oil, and the melting is maintained at 100 ℃ and 120 ℃;
2. 4g of p-toluenesulfonic acid catalyst is added into the reaction system, and the mixture is stirred for half an hour;
3. adding 40g of phenol and 20g of terephthalyl alcohol, keeping the system temperature at 100 ℃ and 120 ℃, and continuously stirring for 1-3 h;
4. adding hexamethylene diamine into the reaction liquid, and adjusting the reaction liquid to be neutral to obtain the modified resin liquid.
Performance detection
1. The modified resin liquids obtained in examples 1 to 10 were subjected to property measurement, and the results are shown in Table 1.
TABLE 1 Properties of modified resin solutions obtained in examples 1 to 10
As can be seen from table 1, the crosslinking method employed in the present invention can effectively convert the polycyclic aromatic hydrocarbon present in the resin, and furthermore, the resin and the solvent have wide sources and are convenient to produce. The used resin has an unsaturated bond, the modifier has a specific functional group, and the modifier has the unsaturated bond with a special environment, so an aromatic ring-alkylating reagent system can be established in the modified resin liquid, the polycyclic aromatic hydrocarbon has good electrophilic reaction activity, and electrophilic substitution reaction and even crosslinking effect are generated between the catalytic action of an acidic catalyst and the alkylating reagent (such as the unsaturated bond in the resin, the specific functional group in the modifier, and the like) in the system, so that polycyclic aromatic hydrocarbon conversion is realized, the polycyclic aromatic hydrocarbon is fixed on the molecular weight of the resin in a chemical bonding manner, the free polycyclic aromatic hydrocarbon is reduced, and the purpose of reducing the harm of the polycyclic aromatic hydrocarbon is achieved.
2. The modified resin liquids obtained in examples 1 to 10 were blended with the base oils in the proportions shown in Table 2 to prepare rubber oils, and the obtained rubber oils were subjected to the tests for the properties thereof, and the results are shown in Table 3.
TABLE 2 compounding ratio of the rubber oils prepared
TABLE 3 results of testing the properties of the rubber oils
As can be seen from Table 3, the modified resin liquid of the present invention can be directly blended with various raw oils to prepare rubber oil, and the content of polycyclic aromatic hydrocarbon in the prepared rubber oil meets European Union standards, and simultaneously, different raw oils can be selected according to different requirements, thereby flexibly adjusting and controlling parameters such as component carbon type, viscosity, etc. of the rubber oil.
Claims (10)
1. The preparation method of the modified resin liquid is characterized by comprising the following steps:
(1) dissolving the resin R in the dissolved oil 01, and fully melting and dispersing;
(2) adding a catalyst L and continuously stirring uniformly;
(3) adding a modifier B, and modifying under heating and stirring;
(4) and after the modification is finished, adding an acid-base regulator, and regulating the reaction liquid to be neutral to obtain the modified resin liquid.
2. The method according to claim 1, wherein the modified resin liquid is prepared by: the resin R is low molecular weight polymer petroleum resin or natural resin.
3. The method according to claim 2, wherein the modified resin liquid is prepared by: the resin R is one or a mixture of more than two of C9 resin, C5 resin, dicyclopentadiene resin and monomers thereof, alpha-methyl styrene homopolymerization resin or monomers, copolymerization resin based on alpha-methyl styrene as a main chain, terpene resin, pinene resin, asphalt or conpa resin.
4. The method according to claim 1, wherein the modified resin liquid is prepared by: the dissolved oil 01 is one or a mixture of two or more of aromatic hydrocarbon base oil, naphthenic oil and paraffin base oil.
5. The method according to claim 4, wherein the modified resin liquid is prepared by: detecting the content of benzo (a) pyrene in the dissolved oil 01 by polycyclic aromatic hydrocarbon to be 0-50 ppm; the total content of PAHs in benzo (a) pyrene, benzo (e) pyrene, benzo (a) anthracene, chrysene, benzo (b) fluoranthene, benzo (j) fluoranthene, benzo (k) fluoranthene and dibenzo (a, h) anthracene 8 is 0-1000 ppm.
6. The method according to claim 1, wherein the modified resin liquid is prepared by: the catalyst L is AlCl3、FeCl3、H2SO4、H3PO4、BF3、BF3One or more of a complex and HF.
7. The method according to claim 1, wherein the modified resin liquid is prepared by: the modifier B is one or more of phenol, cardanol, m-cresol, bornene, ethylidene norbornene, dicyclopentadiene, coumarone resin, hexamethoxy melamine resin, divinylbenzene, p-benzhydrol or paraformaldehyde.
8. The method according to claim 1, wherein the modified resin liquid is prepared by: the mass ratio of the resin R, the dissolved oil 01, the modifier B and the catalyst L is 30-50: 20-70: 1-5: 0.1-0.8.
9. The method according to claim 1, wherein the modified resin liquid is prepared by: the melting temperature is 100-120 ℃, the modification time is 2-4 h, and the acid-base regulator is one or a mixture of more than two of hexamethylene diamine, ethylene diamine or triethylamine.
10. A modified resin liquid, which is produced by the production method according to any one of claims 1 to 10.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113651905A (en) * | 2021-08-31 | 2021-11-16 | 江苏麒祥高新材料有限公司 | Low-heat-generation functional resin and preparation method and application thereof |
| WO2022052436A1 (en) * | 2020-09-14 | 2022-03-17 | 江苏麒祥高新材料有限公司 | Environmentally friendly rubber oil preparation method, and prepared environmentally friendly rubber oil |
| CN114702611A (en) * | 2022-05-18 | 2022-07-05 | 江苏麒祥高新材料有限公司 | Anti-slippery resin and preparation method and application thereof |
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| WO2022052436A1 (en) * | 2020-09-14 | 2022-03-17 | 江苏麒祥高新材料有限公司 | Environmentally friendly rubber oil preparation method, and prepared environmentally friendly rubber oil |
| CN113651905A (en) * | 2021-08-31 | 2021-11-16 | 江苏麒祥高新材料有限公司 | Low-heat-generation functional resin and preparation method and application thereof |
| CN114702611A (en) * | 2022-05-18 | 2022-07-05 | 江苏麒祥高新材料有限公司 | Anti-slippery resin and preparation method and application thereof |
| CN114702611B (en) * | 2022-05-18 | 2024-01-02 | 江苏麒祥高新材料有限公司 | Anti-wet-skid resin and preparation method and application thereof |
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