A rosin-based cationic surfactant and its preparation method and application

By preparing quaternary ammonium salt of propylene pimarate as a rosin-based cationic surfactant, the problems of emulsification and viscosity increase of rosin polyol ester in water-based products were solved, and stable emulsification and viscosity increase effects were achieved, making it suitable for fields such as adhesives and coatings.

CN118221535BActive Publication Date: 2025-09-16GUANGZHOU YINGKE NEW MATERIALS CO LTD
View PDF 0 Cites 0 Cited by

Patent Information

Application Number
CN202410320832.5
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-03-20
Publication Date
2025-09-16
Estimated Expiration
2044-03-20

AI Technical Summary

Technical Problem

Existing technologies make it difficult to effectively emulsify rosin polyol esters in water-based products, and traditional methods affect their viscosity-increasing properties or do not meet environmental protection requirements.

Method used

Acrylopimaric acid quaternary ammonium salt is used as a rosin-based cationic surfactant, which is prepared through esterification and ring-opening reaction. The quaternary ammonium cation and the phenanthrene ring structure of rosin are combined to achieve the emulsification and viscosity-increasing effect on rosin polyol ester.

Benefits of technology

The stable emulsification of rosin polyol ester in water-based products is achieved, while the tackifying performance is improved and antibacterial properties are possessed, making it suitable for applications such as adhesives and coatings.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN118221535B_ABST
    Figure CN118221535B_ABST
Patent Text Reader

Abstract

The present invention belongs to the field of surfactant technology, and in particular to a rosin-based cationic surfactant and its preparation method and application. The rosin-based cationic surfactant is mainly composed of propylene pimarate ester quaternary ammonium salt, and the preparation method of the surfactant comprises the following steps: S1, propylene pimaric acid and triethylene glycol or diethylene glycol undergo esterification reaction to prepare propylene pimarate; S2, the propylene pimarate described in step S1 is reacted with 2,3-epoxypropyltrimethylammonium chloride to obtain a rosin-based cationic surfactant. The rosin-based cationic surfactant of the present invention has excellent emulsifying properties for rosin polyol esters, can provide a good tackifying effect, and also exhibits good antibacterial properties, so that the rosin-based cationic surfactant of the present invention has a wider application prospect in related fields such as adhesives and coatings.
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

[0001] The invention belongs to the technical field of surfactants, and in particular relates to a rosin-based cationic surfactant and a preparation method and application thereof. Background Art

[0002] Rosin-based cationic surfactants are novel surfactants derived from modified versions of traditional cationic surfactants. Using rosin as the primary raw material, these surfactants, through a specific chemical reaction, form a complex that exhibits both cationic and rosin-like properties. These surfactants exhibit a variety of functionalities, including antistatic properties, moderate antimicrobial activity, and excellent thickening and emulsification properties. They are widely used in a variety of fields, including adhesives, paints, asphalt, and rubber.

[0003] Rosin resin is a compound synthesized through a series of chemical reactions involving conjugated double bonds and carboxyl groups in the rosin molecule. In these reactions, rosin combines with polyols (such as glycerol and pentaerythritol) to produce products such as rosin glycerol ester and rosin pentaerythritol ester. Furthermore, derivatives such as maleic acid resin can be obtained by reacting modified rosin with glycerol. These rosin resin derivatives play an important role in industries such as adhesives, coatings, and inks, and are commonly used as tackifying resins or binders.

[0004] However, due to its unique ring structure, rosin resin has a large steric hindrance and is difficult to emulsify. Even if emulsified, it easily forms aggregates and has poor stability, which limits its direct application in water-based products. To overcome this shortcoming, Shang Shibin et al. studied the effects of factors such as the type, dosage, addition method, and operating conditions of emulsifiers and emulsifiers on emulsion properties in "Preparation of Low Softening Point Rosin Resin Emulsion" (Forest Products Chemistry and Industry, 2009, 29). Lin Yun et al. studied the emulsification conditions of rosin resin in "Emulsification of Rosin Resin and Composite Stability of Natural Rubber Latex" (Polymer Materials Science and Engineering, 1996, 12), examined the stability of rosin resin emulsions, and found that the dosage of casein, gelatin, and KOH had an impact on emulsion stability. Rao Xiaoping et al. studied the synthesis, characterization and properties of rosin ester hydroxypropyl quaternary ammonium surfactants by reacting dehydroabietic acid, propylene pimaric acid and maleopimaric acid with 2,3-epoxypropyltrimethylammonium chloride respectively, and studied the critical micelle concentration, surface tension, emulsification performance, foaming performance and antibacterial performance.

[0005] Existing technologies include emulsifying rosin resin into an aqueous dispersion or preparing a rosin resin aqueous solution by adding hydrophilic groups and using solvents to assist dissolution. However, these methods have limitations. For example, emulsifiers negatively impact the tackifying properties of rosin resin, and the emulsion produced by solvent-assisted emulsification may contain residual organic solvents. Furthermore, the use of organic solvents does not meet environmental standards.

[0006] To address these issues, the present invention provides a surfactant that not only serves as an emulsifier for rosin polyol esters but also exhibits a viscosity-enhancing effect, without affecting the viscosity-enhancing properties of the rosin polyol esters. This surfactant is designed to enable the effective application of rosin polyol esters in water-based products while meeting both environmental and performance requirements. Summary of the Invention

[0007] Terms and Claims of the Present Invention:

[0008] 1. The articles "a", "an" and "the" include plural referents unless expressly limited to one or more referents in other ways.

[0009] 2. Numerical ranges: Unless expressly stated otherwise, all ranges or ratios disclosed herein are to be understood to include any and all subranges or subratios contained therein. For example, a range or ratio stated as 1 to 30 is to be considered inclusive of any and all subranges or subratios, integers, decimals, or subranges or subratios comprised therein, including the minimum value of 1 and the maximum value of 30.

[0010] To address the technical problem in the prior art that emulsifiers in aqueous dispersions of rosin polyol esters affect the tackifying properties of the rosin polyol esters, the present invention provides a rosin-based cationic surfactant, a preparation method, and applications thereof. The rosin-based cationic surfactant provided by the present invention exhibits excellent emulsifying properties for rosin polyol esters and provides a good tackifying effect.

[0011] To achieve the above object, the present invention adopts the following technical solutions:

[0012] The invention provides a rosin-based cationic surfactant, which is mainly composed of acrylopimarate quaternary ammonium salt.

[0013] Furthermore, the quaternary ammonium salt of propylene pimarate is quaternary ammonium salt of triethylene glycol propylene pimarate or quaternary ammonium salt of diethylene glycol propylene pimarate. The structural formula of the quaternary ammonium salt of triethylene glycol propylene pimarate is shown in Formula I, and the structural formula of the quaternary ammonium salt of diethylene glycol propylene pimarate is shown in Formula II:

[0014]

[0015]

[0016] Furthermore, the acid value of the rosin-based cationic surfactant is 0.5-2 mg / g.

[0017] The present invention also provides a method for preparing the rosin-based cationic surfactant, comprising the following steps:

[0018] S1, esterifying propylene pimaric acid with triethylene glycol or diethylene glycol to prepare propylene pimaric acid ester;

[0019] S2. Reacting the propylene pimarate described in step S1 with 2,3-epoxypropyltrimethylammonium chloride to obtain a rosin-based cationic surfactant.

[0020] Furthermore, the purity of the acrylpimaric acid in step S1 is ≥96%.

[0021] Acrylopimaric acid is obtained by the addition reaction of rosin and acrylic acid followed by purification. If the purity is not 100%, it will contain a certain proportion of rosin acid.

[0022] Furthermore, the molar ratio of acrylpimaric acid to triethylene glycol or diethylene glycol in step S1 is 1:0.5-2, and the molar number of acrylpimaric acid in step S1 is calculated based on the purity of acrylpimaric acid.

[0023] Furthermore, the esterification reaction in step S1 is carried out at a temperature of 160-180° C. and for a time of 10-20 h.

[0024] Furthermore, the propylene pimarate described in step S1 comprises propylene pimaric acid triethylene glycol monoester or propylene pimaric acid diethylene glycol monoester, and rosin acid.

[0025] Furthermore, the molar ratio of propylene pimarate to 2,3-epoxypropyltrimethylammonium chloride in step S2 is 1:1.

[0026] Furthermore, the molar number of propylene pimarate in step S2 is the sum of the molar number of triethylene glycol propylene pimarate and the molar number of rosin acid, or the sum of the molar number of diethylene glycol propylene pimarate and the molar number of rosin acid.

[0027] Furthermore, the solvent for the reaction in step S2 is anhydrous ethanol.

[0028] Furthermore, the reaction in step S2 is heated to reflux, and a ring-opening reaction is carried out for 3-6 hours, and the solvent is removed to obtain a rosin-based cationic surfactant.

[0029] The present invention also provides the use of the rosin-based cationic surfactant in emulsifying rosin polyol ester.

[0030] Furthermore, when the rosin-based cationic surfactant is used as an emulsifier, the amount of the rosin-based cationic surfactant used is 5-35 wt % of the solid mass in the rosin polyol ester emulsion.

[0031] Furthermore, the amount of the rosin-based cationic surfactant used is 10-30 wt % of the solid mass in the rosin polyol ester emulsion.

[0032] Furthermore, the amount of the rosin-based cationic surfactant used is 15-25 wt % of the solid mass in the rosin polyol ester emulsion.

[0033] The present invention also provides an emulsifier comprising the rosin-based cationic surfactant.

[0034] The present invention also provides the use of the rosin-based cationic surfactant in improving the tackifying performance of rosin polyol ester.

[0035] The present invention also provides a pressure-sensitive adhesive, which utilizes the rosin-based cationic surfactant to improve its tackifying performance.

[0036] Compared with the prior art, the present invention has the following beneficial effects:

[0037] The rosin-based cationic surfactant provided by the present invention has excellent emulsifying properties for rosin resin and can provide good viscosity-increasing effect.

[0038] The rosin-based cationic surfactant of the present invention exhibits excellent emulsification properties for rosin resins, such as rosin glycerol ester and rosin pentaerythritol ester. This is due to the presence of both quaternary ammonium cations and rosin phenanthrene rings in its molecular structure. This unique structure imparts both hydrophilic and lipophilic properties to the rosin-based cationic surfactant, enabling it to effectively emulsify and disperse rosin resins.

[0039] When used as an emulsifier, the rosin-based cationic surfactant of the present invention not only does not interfere with the tackifying properties of rosin polyol esters, but actually further enhances their viscosity. This is due to the inclusion of triethylene glycol or diethylene glycol in the molecular structure of the rosin-based cationic surfactant, which provides good compatibility with the rosin polyol esters, which are inherently nonionic surfactants, without affecting the tackifying effect during application. This makes the rosin-based cationic surfactant have broad application potential in adhesives, coatings, and other related fields.

[0040] The rosin-based cationic surfactant of the present invention also exhibits good antibacterial properties, which is mainly attributed to the quaternary ammonium cations in its molecules. This property enables the rosin-based cationic surfactant to play an important role in the antibacterial effect of rosin resin emulsions. BRIEF DESCRIPTION OF THE DRAWINGS

[0041] Figure 1 These are pictures of the emulsions prepared in Application Examples 1-5 of the present invention. DETAILED DESCRIPTION

[0042] The technical solutions of the present invention are further illustrated below through specific examples, but the protection scope of the present invention is not limited to these examples.

[0043] It is worth noting that, unless otherwise specified, the raw materials and auxiliary agents used in the present invention are all industrial-grade products obtained through common commercial channels, and their sources are not specifically limited.

[0044] Example 1

[0045] The preparation method of rosin-based cationic surfactant comprises the following steps:

[0046] S1. In a four-necked flask equipped with a stirrer, a water separator, a thermometer, and a nitrogen inlet tube, under nitrogen protection, 100 g (0.257 mol) of propylene pimaric acid and 38.6 g (0.257 mol) of triethylene glycol were weighed and added to the four-necked flask. The mixture was heated to 170° C. for esterification for 16 hours to obtain propylene pimaric acid ester as a light yellow viscous substance with an acid value of 115.8 mg / g.

[0047] S2. Weigh 100 g (0.201 mol) of propylene pimarate obtained in step S1 and 30.5 g (0.201 mol) of 2,3-epoxypropyltrimethylammonium chloride and add them into a four-necked flask. Add 200 mL of anhydrous ethanol and heat to reflux to carry out a ring-opening reaction for 4.5 hours. After the reaction, distill the solvent off using a rotary evaporator to obtain a rosin-based cationic surfactant as an amber viscous substance with an acid value of 0.9 mg / g.

[0048] The propylene pimarate described in step S1 is composed of triethylene glycol monopropylene pimarate and rosin acid.

[0049] Acrylopimaric acid indicators: purity 96.1%, acid value 296.4mg / g.

[0050] Example 2

[0051] The preparation method of rosin-based cationic surfactant comprises the following steps:

[0052] S1. In a four-necked flask equipped with a stirrer, a water separator, a thermometer, and a nitrogen inlet tube, under nitrogen protection, 100 g (0.257 mol) of propylene pimaric acid and 38.6 g (0.257 mol) of triethylene glycol were weighed and added to the four-necked flask. The mixture was heated to 160° C. for esterification reaction for 20 hours to obtain propylene pimaric acid ester as a light yellow viscous substance with an acid value of 116 mg / g.

[0053] S2. Weigh 100 g (0.201 mol) of propylene pimarate obtained in step S1 and 30.5 g (0.201 mol) of 2,3-epoxypropyltrimethylammonium chloride into a four-necked flask, add 200 mL of anhydrous ethanol, and heat to reflux to carry out a ring-opening reaction for 6 hours. After the reaction, distill the solvent off using a rotary evaporator to obtain a rosin-based cationic surfactant as an amber viscous substance with an acid value of 0.7 mg / g.

[0054] The propylene pimarate described in step S1 is composed of triethylene glycol monopropylene pimarate and rosin acid.

[0055] Acrylopimaric acid indicators: purity 96.1%, acid value 296.4mg / g.

[0056] Example 3

[0057] The preparation method of rosin-based cationic surfactant comprises the following steps:

[0058] S1. In a four-necked flask equipped with a stirrer, a water separator, a thermometer, and a nitrogen inlet tube, under nitrogen protection, 100 g (0.257 mol) of propylene pimaric acid and 38.6 g (0.257 mol) of triethylene glycol were weighed and added to the four-necked flask. The mixture was heated to 180° C. for esterification reaction for 10 hours to obtain propylene pimaric acid ester as a light yellow viscous substance with an acid value of 116.1 mg / g.

[0059] S2. Weigh 100 g (0.201 mol) of propylene pimarate obtained in step S1 and 30.5 g (0.201 mol) of 2,3-epoxypropyltrimethylammonium chloride into a four-necked flask, add 200 mL of anhydrous ethanol, and heat to reflux to carry out a ring-opening reaction for 3 hours. After the reaction, remove the solvent by distillation using a rotary evaporator to obtain a rosin-based cationic surfactant as an amber viscous substance with an acid value of 1.9 mg / g.

[0060] The propylene pimarate described in step S1 is composed of triethylene glycol monopropylene pimarate and rosin acid.

[0061] Acrylopimaric acid indicators: purity 96.1%, acid value 296.4mg / g.

[0062] Example 4

[0063] The preparation method of rosin-based cationic surfactant comprises the following steps:

[0064] S1. In a four-necked flask equipped with a stirrer, a water separator, a thermometer, and a nitrogen inlet tube, under nitrogen protection, 100 g (0.257 mol) of propylene pimaric acid and 27.3 g (0.257 mol) of diethylene glycol were weighed and added to the four-necked flask. The mixture was heated to 170° C. for esterification for 16 hours to obtain propylene pimaric acid ester as a light yellow viscous substance with an acid value of 126.2 mg / g.

[0065] S2. Weigh 100 g (0.22 mol) of propylene pimarate obtained in step S1 and 33.4 g (0.22 mol) of 2,3-epoxypropyltrimethylammonium chloride and add them into a four-necked flask. Add 200 mL of anhydrous ethanol and heat to reflux to carry out a ring-opening reaction for 4.5 hours. After the reaction, distill the solvent off using a rotary evaporator to obtain a rosin-based cationic surfactant as an amber viscous substance with an acid value of 0.8 mg / g.

[0066] The propylene pimarate described in step S1 is composed of diethylene glycol propylene pimarate and rosin acid.

[0067] Acrylopimaric acid indicators: purity 96.1%, acid value 296.4mg / g.

[0068] Example 5

[0069] The preparation method of rosin-based cationic surfactant comprises the following steps:

[0070] S1. In a four-necked flask equipped with a stirrer, a water separator, a thermometer, and a nitrogen inlet tube, under nitrogen protection, 100 g (0.257 mol) of propylene pimaric acid and 27.3 g (0.257 mol) of diethylene glycol were weighed and added to the four-necked flask. The mixture was heated to 160° C. for esterification reaction for 20 hours to obtain propylene pimaric acid ester as a light yellow viscous substance with an acid value of 126.1 mg / g.

[0071] S2. Weigh 100 g (0.22 mol) of propylene pimarate obtained in step S1 and 33.4 g (0.22 mol) of 2,3-epoxypropyltrimethylammonium chloride and add them into a four-necked flask. Add 200 mL of anhydrous ethanol and heat to reflux to carry out a ring-opening reaction for 3 hours. After the reaction, distill the solvent off using a rotary evaporator to obtain a rosin-based cationic surfactant as an amber viscous substance with an acid value of 1.5 mg / g.

[0072] The propylene pimarate described in step S1 is composed of diethylene glycol propylene pimarate and rosin acid.

[0073] Acrylopimaric acid indicators: purity 96.1%, acid value 296.4mg / g.

[0074] Comparative Example 1

[0075] The selected acrylpimaric acid has the following indicators: purity 90%, acid value 288.1 mg / g.

[0076] The preparation method of rosin-based cationic surfactant comprises the following steps:

[0077] S1. In a four-necked flask equipped with a stirrer, a water separator, a thermometer, and a nitrogen inlet tube, under nitrogen protection, 100 g (0.24 mol) of propylene pimaric acid and 36.0 g (0.24 mol) of triethylene glycol were weighed and added to the four-necked flask. The mixture was heated to 170° C. for esterification for 16 hours to obtain propylene pimaric acid ester as a light yellow viscous substance with an acid value of 126.6 mg / g.

[0078] S2. Weigh 100 g (0.207 mol) of propylene pimarate obtained in step S1 and 31.4 g (0.207 mol) of 2,3-epoxypropyltrimethylammonium chloride into a four-necked flask, add 200 mL of anhydrous ethanol, and heat to reflux to carry out a ring-opening reaction for 4.5 hours. After the reaction, distill off the solvent using a rotary evaporator to obtain a rosin-based cationic surfactant as an amber viscous substance with an acid value of 1 mg / g.

[0079] The propylene pimarate described in step S1 is composed of diethylene glycol propylene pimarate and rosin acid.

[0080] Comparative Example 2

[0081] The difference between this comparative example and Example 1 is that the molar ratio of propylene pimarate to 2,3-epoxypropyltrimethylammonium chloride in step S2 is different. Specifically, "30.5 g (0.201 mol) of 2,3-epoxypropyltrimethylammonium chloride" in Example 1 is replaced with "27.4 g (0.181 mol) of 2,3-epoxypropyltrimethylammonium chloride". The acid value of the obtained rosin-based cationic surfactant is 10.3 mg / g.

[0082] Comparative Example 3

[0083] The difference between this comparative example and Example 1 is that the temperature of the esterification reaction in step S1 is 190° C., the acid value of the obtained propylene pimarate is 88.5 mg / g, and the acid value of the rosin-based cationic surfactant is 0.1 mg / g.

[0084] Comparative Example 4

[0085] In this comparative example, propylene pimaric acid was directly reacted with 2,3-epoxypropyltrimethylammonium chloride to prepare a rosin-based cationic surfactant, and triethylene glycol was omitted.

[0086] The preparation method of rosin-based cationic surfactant comprises the following steps:

[0087] S1. In a three-necked flask equipped with a stirring device, a water separator and a thermometer, 100 g (0.257 mol) of propylene pimaric acid and 93.6 g (0.617 mol) of 2,3-epoxypropyltrimethylammonium chloride were weighed and added to the three-necked flask. 200 mL of anhydrous ethanol was added and the mixture was heated to reflux for 4.5 hours. After the reaction was completed, the solvent was distilled off using a rotary evaporator to obtain a rosin-based cationic surfactant.

[0088] Acrylopimaric acid indicators: purity 96.1%, acid value 296.4mg / g.

[0089] To verify the emulsifying effect of the rosin-based cationic surfactant of the present invention, the emulsifying effect was evaluated by emulsifying rosin glycerol ester, rosin pentaerythritol ester, or a mixture thereof. The rosin pentaerythritol ester used commercially available 146 resin with an acid value of 29 mg / g and a softening point of 98°C; the rosin glycerol ester used commercially available 138 resin with an acid value of 7 mg / g and a softening point of 88°C.

[0090] Application Example 1

[0091] Weigh 100 g of 146 resin and 18 g of the rosin-based cationic surfactant prepared in Example 1, add them to an emulsifying kettle with adjustable speed, heat to 100-150° C. and stir to mix, then cool to 75-95° C. and slowly add 100 g of 80-90° C. deionized water dropwise with stirring at 120 rpm. After phase inversion is observed, quickly add the remaining deionized water, stir at 300 rpm for 10 minutes, then cool to 60° C. and add water to adjust the solid content to 50%.

[0092] Application Example 2

[0093] Weigh 100 g of 146 resin and 20 g of the rosin-based cationic surfactant prepared in Example 4, add them to an emulsifying kettle with adjustable speed, heat to 100-150° C. and stir to mix, then cool to 75-95° C. and slowly add 100 g of 80-90° C. deionized water dropwise with stirring at 120 rpm. After phase inversion is observed, quickly add the remaining deionized water, stir at 300 rpm for 10 minutes, then cool to 60° C. and add water to adjust the solid content to 50%.

[0094] Application Example 3

[0095] Weigh 50 g of resin 138, 50 g of resin 146, and 25 g of the rosin-based cationic surfactant prepared in Example 4, add them to an emulsifying kettle with adjustable speed, heat to 100-150° C. and stir to mix, then cool to 75-95° C. and slowly add 100 g of deionized water at 80-90° C. dropwise with stirring at 120 rpm. After phase inversion is observed, quickly add the remaining deionized water, stir at 300 rpm for 10 minutes, then cool to 60° C. and add water to adjust the solid content to 50%.

[0096] Application Example 4

[0097] Replace "20 g of the rosin-based cationic surfactant prepared in Example 1" in Application Example 1 with "33 g of the rosin-based cationic surfactant prepared in Example 1".

[0098] Application Example 5

[0099] Change “weigh 50 g of 138 resin and 50 g of 146 resin” in Application Example 3 to “weigh 100 g of 138 resin”.

[0100] The emulsions prepared in the above application examples 1-5 are shown in the following pictures: Figure 1 As shown, it is a milky white liquid. Microscopic determination shows that the emulsion particle size is 200-500 nanometers. Under room temperature conditions, it is stable within 6 months without precipitation or stratification.

[0101] Effect performance test

[0102] Determination of the viscosity-increasing properties of a rosin-based cationic surfactant

[0103] Since rosin polyol esters cannot be emulsified directly, the present invention evaluates the tackifying effect of the rosin-based cationic surfactant of the present invention by measuring the mechanical properties of hot melt pressure-sensitive adhesives prepared from rosin pentaerythritol ester 146 or rosin pentaerythritol esters containing different proportions of rosin-based cationic surfactants.

[0104] The mass ratio of rosin pentaerythritol ester and rosin-based cationic surfactant is shown in Table 1 below. The data in Table 1 represent the weight percentage of the corresponding substances in the tackifying resin.

[0105] Table 1

[0106]

[0107]

[0108] Hot melt pressure-sensitive adhesive is composed of the following raw materials: elastomer SBS: 30g, tackifying resin: 50g, naphthenic oil 4010: 19g, antioxidant D: 1g.

[0109] Hot melt pressure sensitive adhesive test sample preparation:

[0110] Add tackifying resin, naphthenic oil 4010 and antioxidant D to a four-necked flask equipped with a stirrer and a thermometer, heat and introduce nitrogen protection, start stirring after the tackifying resin melts (stirring speed 30-60r / min), stir all the components evenly, then raise the temperature to 150-170℃, add thermoplastic elastomer SBS in batches until the SBS is completely melted, vacuum to remove white bubbles, and stop heating and stirring when the system becomes a uniform, transparent, viscous liquid. Put it into the coater while it is hot to prepare a hot melt pressure-sensitive adhesive test sample.

[0111] Hot melt pressure sensitive adhesive index determination method:

[0112] Softening point: Determined by the ring and ball method in accordance with GB / T 15332-1994.

[0113] Initial adhesion: measured according to Finat FTM-9 Loop tack standard using an intelligent electronic tensile testing machine.

[0114] 180° peel strength: measured according to GB / T 2792-1998 standard using an intelligent electronic tensile testing machine.

[0115] Adhesion: measured according to GB / T 4851-1998 standard using an adhesion tester.

[0116] Glass transition temperature: measured using a Physica MCR 101 rheometer.

[0117] The test results of hot melt pressure sensitive adhesive are shown in Table 2.

[0118] Table 2

[0119]

[0120]

[0121] As can be seen from Table 2, the hot melt pressure-sensitive adhesives 2#-6# prepared with the tackifying resin BF containing the rosin-based cationic surfactant of the present invention have significantly improved initial adhesive force and 180° peel strength compared with the hot melt pressure-sensitive adhesive 1# prepared with A, and the application temperature width is increased, that is, the difference between the softening point and the glass transition temperature Tg is increased; the hot melt pressure-sensitive adhesives 7#-9# prepared with the tackifying resin GI have reduced 180° peel strength and holding force compared with the hot melt pressure-sensitive adhesive 1# prepared with the tackifying resin A; the hot melt pressure-sensitive adhesive 10# prepared with the tackifying resin J has significantly reduced initial adhesive force compared with the hot melt pressure-sensitive adhesive 1# prepared with the tackifying resin A; the hot melt pressure-sensitive adhesive 11# prepared with the tackifying resin K has reduced various indicators compared with the hot melt pressure-sensitive adhesive 1# prepared with the tackifying resin A.

[0122] The rosin-based cationic surfactant of the present invention, when used as an emulsifier, does not affect the tackifying performance of the rosin polyol ester, but can further enhance the tackifying performance of the rosin polyol ester, showing a wider application potential in related fields such as adhesives and coatings.

[0123] Finally, it should be noted that the above content is only used to illustrate the technical solution of the present invention, rather than to limit the scope of protection of the present invention. Simple modifications or equivalent substitutions of the technical solution of the present invention by ordinary technicians in this field do not deviate from the essence and scope of the technical solution of the present invention.

Claims

1. A rosin-based cationic surfactant, characterized in that The main component is quaternary ammonium salt of propylene pimarate; The quaternary ammonium salt of propylene pimarate is quaternary ammonium salt of triethylene glycol propylene pimarate or quaternary ammonium salt of diethylene glycol propylene pimarate. The structural formula of the quaternary ammonium salt of triethylene glycol propylene pimarate is shown in Formula I, and the structural formula of the quaternary ammonium salt of diethylene glycol propylene pimarate is shown in Formula II: , 。 2. The rosin-based cationic surfactant according to claim 1, wherein The acid value of the rosin-based cationic surfactant is 0.5-2 mg / g.

3. The method for preparing the rosin-based cationic surfactant according to any one of claims 1 to 2, characterized in that: The following steps are involved: S1, esterifying propylene pimaric acid with triethylene glycol or diethylene glycol to prepare propylene pimaric acid ester; S2. Reacting the propylene pimarate described in step S1 with 2,3-epoxypropyltrimethylammonium chloride to obtain a rosin-based cationic surfactant.

4. The preparation method according to claim 3, characterized in that The purity of the acrylopimaric acid in step S1 is ≥96%; The molar ratio of acrylpimaric acid to triethylene glycol or diethylene glycol in step S1 is 1:0.5-2, and the molar number of acrylpimaric acid is calculated based on the purity of acrylpimaric acid; The esterification reaction in step S1 is carried out at a temperature of 160-180° C. and for 10-20 hours; The molar ratio of propylene pimarate to 2,3-epoxypropyltrimethylammonium chloride in step S2 is 1:1; The solvent for the reaction in step S2 is anhydrous ethanol; The reaction in step S2 is heated to reflux, and a ring-opening reaction is carried out for 3-6 hours, and the solvent is removed to obtain a rosin-based cationic surfactant.

5. Use of the rosin-based cationic surfactant according to any one of claims 1 to 2 or the rosin-based cationic surfactant prepared by the preparation method according to any one of claims 3 to 4 in emulsifying rosin polyol ester.

6. Use of the rosin-based cationic surfactant according to any one of claims 1 to 2 or the rosin-based cationic surfactant prepared by the preparation method according to any one of claims 3 to 4 in improving the tackifying performance of rosin polyol ester.

7. The use according to claim 5, characterized in that When the rosin-based cationic surfactant is used as an emulsifier, the amount of the rosin-based cationic surfactant used is 5-35 wt % of the solid mass in the rosin polyol ester emulsion.

8. An emulsifier, characterized in that The invention relates to a rosin-based cationic surfactant comprising the rosin-based cationic surfactant according to any one of claims 1 to 2 or the rosin-based cationic surfactant prepared by the preparation method according to any one of claims 3 to 4.

9. A pressure-sensitive adhesive, characterized in that: The rosin-based cationic surfactant described in any one of claims 1 to 2 or the rosin-based cationic surfactant prepared by the preparation method described in any one of claims 3 to 4 has improved tackifying performance.