Pitch control agent and pitch control method

Abstract

To provide a pitch control agent and a pitch control method for suppression of pitch formation and preventing pitch-caused paper tackiness.SOLUTION: A pitch control agent of the present invention is characterized by involving a compound represented by the general formula (1) below (R1 is an alkyl group with a carbon number of 8-16, R2 is a hydroxyalkyl group with a carbon number of 2-4, Xm- is a phosphate ion, a nitrate ion, or a sulfate ion, and m is 1-3).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a pitch control agent and a pitch control method. [Background technology]

[0002] During the waste paper recycling process, pitch is generated from natural resin components derived from wood, resin components contained in gum and cellophane tape, back glue, ink, and coating chemicals attached to the waste paper, and various additives used in the pulping and papermaking processes, such as antifoaming agents, sizing agents, paper strength agents, retention aids, fixing agents, softeners, and density reducers. This pitch adheres to the paper or to papermaking equipment such as aging towers, thickeners, rolls, and dryers, and can fall off and re-adhere to the paper, causing adhesion between the equipment and the paper, leading to paper breaks and other problems during the papermaking process, reducing productivity and workability. In particular, adhesive resin components can cause problems when they adhere between the equipment and the paper during the coating process.

[0003] To solve the above problems, a commonly known method is to add a pitch control agent in each step of waste paper recycling and paper manufacturing to prevent pitch generation.

[0004] For example, Patent Document 1 discloses a pitch anti-adhesion agent containing a condensate of dicyandiamide and polyalkylene polyamine, and a cationic surfactant, wherein the cationic surfactant is at least one cationic surfactant selected from the group consisting of alkyl dimethyl benzyl ammonium chloride, alkyl trimethyl ammonium chloride, and alkyl dimethyl ethyl ammonium ethyl sulfate.

[0005] Patent Document 2 discloses a pitch control agent containing a cationic surfactant, a cationic polymer compound, and a phosphonic acid, in which the cationic surfactant is benzyldimethylalkylammonium chloride having an alkyl group having 10 to 20 carbon atoms.

[0006] Patent Document 3 discloses specific quaternary ammonium salt-type cationic surfactants having an alkyleneoxy group or a hydroxyalkyl group, such as lauryl dimethyl hydroxyethyl paratoluene.

[0007] However, these compositions still have the problem of insufficient pitch control effect. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Japanese Patent Application Publication No. 8-337988 [Patent Document 2] Japanese Patent Application Laid-Open No. 2003-268696 [Patent Document 3] Japanese Patent Application Publication No. 2019-39113 [Patent Document 4] Japanese Patent Application Laid-Open No. 2001-271290 [Patent Document 5] U.S. Patent No. 3,619,351 Summary of the Invention [Problem to be solved by the invention]

[0009] The present invention has been made in view of the problems associated with the above-mentioned conventional techniques, and an object of the present invention is to provide a pitch control agent and a pitch control method that suppress the generation of pitch and prevent paper from becoming sticky due to pitch. [Means for solving the problem]

[0010] The present inventors have found that such problems can be solved by using a quaternary ammonium salt compound having a specific structure, and have completed the present invention.

[0011] That is, the pitch control agent of the present invention is characterized by containing a compound represented by the following general formula (1):

[0012] [ka]

[0013] In formula (1), R 1 is an alkyl group having 8 to 16 carbon atoms, and R 2 , R 3 is a methyl group, and R 4 is a hydroxyalkyl group having 2 to 4 carbon atoms, and X m- is a phosphate ion, a nitrate ion, or a sulfate ion, and m is 1 to 3.

[0014] The pitch control method of the present invention is characterized by adding the compound represented by the above general formula (1) in the pulp or paper manufacturing process. [Effects of the Invention]

[0015] It is effective in suppressing the generation of acrylic ester pitch derived from delivery slips and stickers during the waste paper recycling process, and rubber pitch derived from packing tape, and in preventing the stickiness of paper caused by pitch. DETAILED DESCRIPTION OF THE INVENTION

[0016] Before describing the embodiments of the present invention, a comparison with the prior art will be described.

[0017] The pitch control agent of the present invention is characterized by containing a compound represented by the following general formula (1), wherein R 1 is an alkyl group having 8 to 16 carbon atoms, and R 2 , R 3 is a methyl group, and R 4 is a hydroxyalkyl group having 2 to 4 carbon atoms, and X m- is a phosphate ion, a nitrate ion, or a sulfate ion, and m is 1 to 3.

[0018] [ka]

[0019] Patent Document 3 discloses salts of a broader range of quaternary ammonium salt cations than those of formula (1) above with counter anions as pitch control agents. While these quaternary ammonium salt cations include the quaternary ammonium salt cations of formula (1) above, the counter anions are not limited, and paratoluenesulfonate ions, chloride ions, and methyl sulfate ions are listed in the examples. However, there is no mention or suggestion of the anions of formula (1) above. As will be described later, the pitch control agent of the present invention not only has a greater effect in suppressing pitch generation than the examples of the pitch control agent disclosed in Patent Document 3, but also has a significant effect of reducing the adhesiveness of residual pitch, which is not disclosed or suggested in Patent Document 3.

[0020] Patent Document 4 discloses methyl-alkyl(C8-18)-di-polyoxyethyleneammonium chloride (a chloride salt of a quaternary ammonium) as a pitch control agent, but the combination of this cation and anion is different from any of the cations and anions of the above formula (1).

[0021] Patent Document 5 discloses a salt of a quaternary ammonium salt-type cation and a counter anion, which is a generic concept of the above formula (1), as a pitch control agent, and in particular discloses the methyl sulfate salt of methyltriethanolammonium ion as a suitable pitch control agent. However, this is a different compound from the compound of the above formula (1). Furthermore, the pitch control agent of the present invention has a significant effect of reducing the adhesion of residual pitch, which is not disclosed or suggested in Patent Document 5.

[0022] Next, the compound represented by general formula (1) will be described.

[0023] [ka]

[0024] In formula (1), R 1 is an alkyl group having 8 to 16 carbon atoms, and R 2 , R 3 is a methyl group, and R 4 is a hydroxyalkyl group having 2 to 4 carbon atoms, and X m- is a phosphate ion, a nitrate ion, or a sulfate ion, and m is 1 to 3.

[0025] R 1 From the viewpoint of pitch control performance, an alkyl group having 12 to 14 carbon atoms is preferred. m- From the viewpoint of suppressing rubber-based pitch derived from gummed tape, nitrate ions and sulfate ions are preferred, and from the viewpoint of suppressing acrylic ester-based pitch, phosphate ions are preferred, with nitrate ions being more preferred.

[0026] From the viewpoint of transport efficiency, the content of the compound represented by general formula (1) in the pitch control agent is preferably 1% by mass or more and 100% by mass or less, more preferably 5% by mass or more and 80% by mass or less, and even more preferably 10% by mass or more and 60% by mass or less.

[0027] The compound represented by general formula (1) may be used as a pitch control agent as it is, or may be dissolved, emulsified, or dispersed in water or an organic solvent and used as a pitch control agent. The type of organic solvent is not particularly limited, but examples include lower alcohols having 1 to 6 carbon atoms such as methanol, ethanol, and propanol; alkylene oxide adducts of the lower alcohols; glycols such as ethylene glycol, diethylene glycol, and propylene glycol; and 3-methyl-3-methoxybutanol.

[0028] Next, the pitch control method will be explained.

[0029] One embodiment of the pitch control method of the present invention is characterized by adding the pitch control agent of the present invention in the process of producing pulp or paper.

[0030] Another embodiment of the pitch control method of the present invention is characterized in that the pitch control agent of the present invention is sprayed onto a part of a manufacturing machine that comes into contact with raw materials for paper production during a pulp or paper manufacturing process.

[0031] The pulp or paper manufacturing process and the types of pulp and paper that are the target of the pitch control agent of the present invention are not particularly limited, and for example, the pulp also includes unwashed crude pulp after wood has been cooked.

[0032] Specifically, the pitch control agent of the present invention is used in processes for producing paper using wood pulp or recycled pulp from waste paper.

[0033] First, a method of adding the pitch control agent of the present invention to the paper manufacturing process, which is one embodiment of the pitch control method of the present invention, will be described.

[0034] The location where the pitch control agent of the present invention is added is not particularly limited, but the optimal location varies depending on the paper production, the type of raw material, etc. In the case of producing pulp from recycled paper, examples include adding the agent before or during the disintegration process using a disintegrator or fiber flow drum, before a high-concentration treatment process in which mechanical shear force is applied using a kneader or disperser, or before flotation. On the other hand, in paper production, examples include adding the agent to a mixing chest, machine chest, seed box, etc. used in the process of mixing pulp and chemicals, or to a white water pit (or Sabor, etc.) after papermaking.

[0035] <Amount of pitch control agent used in the present invention> The amount of the pitch control agent used in the present invention is, from the viewpoints of pitch control effect and cost, 0.0005% by mass to 5% by mass of the compound represented by general formula (1) relative to the dry weight of the pulp to be treated, preferably 0.001% by mass to 1% by mass, and more preferably 0.005% by mass to 0.5% by mass.

[0036] Next, a method of spraying the pitch control agent of the present invention onto a manufacturing machine that comes into contact with raw materials for paper production during the paper manufacturing process, which is another embodiment of the pitch control method of the present invention, will be described.

[0037] Examples of spraying equipment include concentrators, washer meshes, etc. in the production of pulp from recycled paper, and papermaking felts, papermaking wires, papermaking rolls, processing rolls, etc. in the production of paper. In these production equipment, the pitch control agent is sprayed at least on the parts that come into contact with the raw materials for paper production.

[0038] The method of spraying the production equipment is not particularly limited, but examples include a washing water shower line, an atomizing spray device, etc. The spraying can be performed continuously during operation or when the operation is stopped.

[0039] In the case of spraying, the amount of the pitch control agent of the present invention used is not particularly limited, and depends on the size, structure, and degree of dirt of the manufacturing equipment that comes into contact with the raw materials for paper production. From the standpoints of pitch control effect and cost, the concentration of the pitch control agent used is preferably from 0.0005% by mass to 5% by mass, more preferably from 0.001% by mass to 5% by mass, and even more preferably from 0.001% by mass to 1% by mass, as the concentration of the compound represented by general formula (1).

[0040] In addition, when using the pitch control agent of the present invention, an acid or alkali agent, a nonionic surfactant, an anionic surfactant, a cationic surfactant other than the compound of general formula (1), an amphoteric surfactant, a higher fatty acid, a mineral oil, an organic solvent, a natural solvent such as orange oil, or the like may be added.

[0041] The present invention will be described in detail below with reference to examples, but the present invention is not limited to the following description. [Example]

[0042] The test method is as follows.

[0043] <Raw materials used> General formula (1) compound The compounds E1 to E8 of the general formula (1) and the quaternary ammonium salt compounds e1 to e22 used in the comparative examples were prepared by synthesis using the known methods shown below.

[0044] [Table 1]

[0045] (E1 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and nitric acid was added to neutralize the mixture. After replacing the atmosphere in the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was then aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (E1).

[0046] (E2 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and phosphoric acid was added to neutralize the mixture. After replacing the atmosphere in the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was then aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (E2).

[0047] (E3 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and the same amount of distilled water by weight, and sulfuric acid was added to neutralize it. After replacing the atmosphere in the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was then aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (E3).

[0048] (E4 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and nitric acid was added to neutralize the mixture. After replacing the atmosphere in the autoclave with nitrogen, 1.5 molar equivalents of propylene oxide were blown in at 85-95°C to cause the reaction. The mixture was then aged for 12 hours to allow the quaternization reaction to proceed, yielding compound (E4).

[0049] (E5 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of decyldimethylamine and an equal weight amount of distilled water, and nitric acid was added to neutralize the mixture. After replacing the atmosphere in the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was then aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (E5).

[0050] (E6 synthesis method) One molar equivalent of tetradecyldimethylamine and an equal weight amount of distilled water were charged into a pressure-resistant reaction vessel (autoclave), and nitric acid was added to neutralize the mixture. After replacing the atmosphere in the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was then aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (E6).

[0051] (E7 synthesis method) One molar equivalent of octyldimethylamine and an equal weight amount of distilled water were charged into a pressure-resistant reaction vessel (autoclave), and nitric acid was added to neutralize the mixture. After replacing the atmosphere in the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was then aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (E7).

[0052] (E8 synthesis method) One molar equivalent of hexadecyldimethylamine and an equal weight amount of distilled water were charged into a pressure-resistant reaction vessel (autoclave), and nitric acid was added to neutralize the mixture. After replacing the atmosphere in the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was then aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (E8).

[0053] [Table 2]

[0054] (e1 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and hydrochloric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e1).

[0055] (How to synthesize e2) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and hydroiodic acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e2).

[0056] (How to synthesize e3) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and boric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e3).

[0057] (How to synthesize e4) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and hydrobromic acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e4).

[0058] (e5 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal amount of distilled water by weight, and phosphorous acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e5).

[0059] (e6 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and hypophosphorous acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e6).

[0060] (e7 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and thioglycolic acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e7).

[0061] (e8 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal amount of distilled water by weight, and citric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e8).

[0062] (e9 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal amount of distilled water by weight, and acetic acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e9).

[0063] (How to synthesize e10) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and p-toluenesulfonic acid monohydrate was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e10).

[0064] (How to synthesize e11) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldimethylamine and an equal weight amount of distilled water, and benzenesulfonic acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e11).

[0065] (E12 synthesis method) One molar equivalent of octadecyldiethanolamine and an equal weight amount of distilled water were charged into a pressure-resistant reaction vessel (autoclave), and nitric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e12).

[0066] (E13 synthesis method) One molar equivalent of octadecyldiethylamine and an equal weight amount of distilled water were charged into a pressure-resistant reaction vessel (autoclave), and nitric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e13).

[0067] (E14 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of tributylamine and an equal weight amount of distilled water, and sulfuric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e14).

[0068] (e15 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldiethanolamine and an equal weight amount of distilled water, and nitric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of propylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 12 hours to allow the quaternization reaction to proceed, yielding compound (e15).

[0069] (e16 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldiethanolamine and the same amount of distilled water by weight. After replacing the autoclave with nitrogen, 1.1 molar equivalents of methyl chloride were blown in at 50-60°C to cause the reaction. The mixture was aged for 12 hours to allow the quaternization reaction to proceed, yielding compound (e16).

[0070] (e17 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of triethanolamine and an equal weight amount of distilled water, and sulfuric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 12 hours to allow the quaternization reaction to proceed, yielding compound (e17).

[0071] (e18 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of diethyl-2-(2'-hydroxyethoxy)ethylamine and an equal weight amount of distilled water, and sulfuric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e18).

[0072] (e19 synthesis method) One molar equivalent of octadecyldimethylamine and an equal weight amount of distilled water were charged into a pressure-resistant reaction vessel (autoclave), and nitric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e19).

[0073] (e20 synthesis method) One molar equivalent of hexyldimethylamine and an equal weight amount of distilled water were charged into a pressure-resistant reaction vessel (autoclave), and nitric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e20).

[0074] (e21 synthesis method) A pressure-resistant reaction vessel (autoclave) was charged with 1 molar equivalent of dodecyldiethanolamine and an equal weight amount of distilled water, and nitric acid was added and mixed to neutralize. After replacing the autoclave with nitrogen, 1.5 molar equivalents of ethylene oxide were blown in at 85-95°C to cause the reaction. The mixture was aged for 4 hours to allow the quaternization reaction to proceed, yielding compound (e21).

[0075] (e22 synthesis method) One molar equivalent of triethanolamine was placed in a four-neck flask equipped with a reflux condenser and heated to 85 to 95° C. 1.1 molar equivalents of dimethyl sulfate was added dropwise to the mixture while stirring, and the mixture was aged for 3 hours to obtain compound (e22).

[0076] <Nonionic surfactants> Stearyl alcohol {(PO)12 / [(EO)30 / (PO)12 random adduct]} block adduct (hereinafter referred to as compound (D)) <Preparation and Evaluation of Pitch Control Agent Composition> <Method for creating test papers for testing pitch control performance on delivery slips> [Example 1] A JIS standard disintegrator was charged with 120 g of a paper mixture of recycled flyers and delivery slips (using an acrylic ester resin as an adhesive) (a mixture of 95% recycled flyers and 5% or less delivery slips), 1.0% by mass of sodium hydroxide (relative to the mixed paper), 0.3% by mass of compound E1 of general formula (1) (relative to the mixed paper), 0.05% by mass of compound (D) (relative to the mixed paper), and water to a concentration of 20% by mass of the mixed paper, and the mixture was disintegrated at 50°C for 60 minutes to obtain disintegrated pulp. The disintegrated pulp was then passed through a circular paper machine according to JISP-8209 to obtain a 150 g / m2 pulp. 2 The handsheet was sandwiched between filter paper for dehydration. It was then pressed and dried in a drum dryer at 105°C for 5 minutes to obtain test paper T1 (before the filter paper was removed) after macerating and washing. The test paper T1 from which the filter paper had been removed was designated test paper T2.

[0077] [Examples 2 to 9, Comparative Examples 1 to 24] Test papers T1 and T2 were obtained after disintegration and washing according to the method of Example 1, except that the amount of compound E1 of general formula (1) in the mixed paper was changed or it was changed to the compound shown in Table 5.

[0078] <Method for creating test paper for testing pitch control performance of kraft tape> [Example 1] In a JIS standard disintegrator, 120 g of paper (a mixture of 95% by mass of recycled flyer paper and 5% or less by mass of Kraft tape) mixed with recycled flyer paper and Kraft tape (using a rubber-based resin as an adhesive) was added, and 0.3% by mass (relative to the mixed paper) of compound E1 of general formula (1) was added. Water was added so that the concentration of the mixed paper became 20% by mass, and the mixture was disintegrated at a temperature of 40°C for 60 minutes to obtain disintegrated pulp. The disintegrated pulp was sieved through a 24-mesh sieve to remove undisintegrated Kraft tape, and washed pulp was obtained. The washed pulp was then sieved in a circular paper machine according to JISP-8209 to obtain a pulp with a basis weight of 150 g / m 2 The handsheet was sandwiched between filter paper for dehydration. It was then pressed and dried in a drum dryer at 105°C for 5 minutes to obtain test paper T1 (before the filter paper was removed) after macerating and washing. The test paper T1 from which the filter paper had been removed was designated test paper T2.

[0079] [Examples 2 to 9, Comparative Examples 1 to 24] Test papers T1 and T2 were obtained after disintegration and washing according to the method of Example 1, except that the amount of compound E1 of general formula (1) in the mixed paper was changed or it was changed to the compound shown in Table 5.

[0080] <Evaluation method> <Measurement of the pitch remaining area ratio on test paper T2> Images of two arbitrary locations (5 cm x 5 cm) on the test paper T2 were captured using a scanner, and the images were analyzed using analysis software to measure the area ratio of black spots caused by remaining pitch.

[0081] Evaluation item: Dirt area ratio Scanner: Seiko Epson GT-X830 Analysis software: Image pro plus manufactured by Nippon Rover Co., Ltd.

[0082] [Table 3]

[0083] In the evaluation criteria, if the pitch remaining area rate on the paper surface is 1 to 3, it is sufficiently small and there is no practical problem, but if it is 4, there is a risk that the paper will stick to itself or to the manufacturing machine, causing problems in manufacturing. Therefore, a rating of 1 to 3 was considered pass, and 4 was considered fail.

[0084] <Evaluation of residual pitch adhesion> (Test method for peel strength between handsheet and filter paper using test paper T1) The test paper T1 after defibration and washing, prepared according to the method for preparing test paper for pitch control performance testing on kraft tape and the method for preparing test paper for pitch control performance testing on delivery slips, was cut to 65 x 50 mm, and the filter paper was peeled off about 15 mm from the edge of the long side (65 mm), the peeled part was clamped with the gripping tool of the testing machine and peeled off at a peeling rate of 50 mm per minute, and the strongest load measured during the peeling was taken as the peel strength. A higher peel strength was evaluated as having higher adhesiveness.

[0085] Peel strength measuring device: JSV-H1000 manufactured by Japan Measurement Systems Co., Ltd.

[0086] [Table 4]

[0087] In the evaluation criteria, if the residual pitch was rated 1 to 3, the adhesiveness was sufficiently small that it would not pose a practical problem, but if it was rated 4, there was a risk that the paper would stick to itself or to the manufacturing machine, causing problems in manufacturing. Therefore, a rating of 1 to 3 was deemed pass, and a rating of 4 was deemed fail.

[0088] [Table 5]

[0089] [Table 6]

[0090] As shown in Tables 5 and 6, when the pitch control agents of Examples 1 to 9 of recycled paper are used in the pulp manufacturing process using recycled paper that is a mixture of flyer waste paper, kraft tape, and delivery slips, the amount of remaining pitch in the recycled waste paper (pitch remaining area ratio on the paper surface) is kept small in both the kraft tape and the delivery slips, and the adhesiveness is also kept small, which is thought to prevent adhesion problems between paper and manufacturing machines and between papers due to pitch in the recycled paper manufacturing process.

[0091] For example, Comparative Example 24 does not contain any pitch control agent, but in the examples, the amount of residual pitch is incomparably smaller than Comparative Example 24, and the adhesiveness is also clearly smaller.

[0092] Generally, it is thought that the greater the amount of remaining pitch, the greater the adhesiveness, and the smaller the amount of remaining pitch, the lower the adhesiveness. However, when comparing the Examples and Comparative Examples, even though the amount of remaining pitch is the same, the Examples have lower adhesiveness. For example, in Example 1 and Comparative Example 2, the pitch area ratio (amount of remaining pitch) is the same for both the craft tape and the delivery slip, but the adhesiveness of Example 1 is significantly lower, and the pitch control agent of the present invention has the effect of reducing adhesiveness itself.

[0093] In the examples of Patent Document 3, chloride ions are primarily used as the anion. Patent Document 4 also uses chloride ions as the anion. Comparative Example 1 (e1) shown in Table 5 of the present application is a pitch control agent in which the anion of Example 1 (E1) is changed to chloride ions. However, the amount of residual pitch is smaller in Example 1 (especially about 1 / 3 in the case of craft tape), and the adhesiveness is clearly lower in Example 1, whereas Comparative Example 1 does not reach a practical level. Furthermore, when comparing Comparative Example 2, in which the amount of e1 added is 3.3 times that of Comparative Example 1, with Example 2, in which the amount of E1 added is 1 / 6 that of Example 1, the adhesiveness is lower in Example 2, despite a 20-fold difference in the amounts added.

[0094] Furthermore, Comparative Examples 3 to 12 (e2 to e11) are pitch control agents using various anions different from the anions of the present invention, but all of them have inferior pitch suppression effects compared to the Examples. Comparative Example 11 is the substance described as Example 1 in Patent Document 3, and is the substance with the highest pitch suppression effect in Patent Document 3, but its adhesion is inferior to any of Examples 1 to 9 of the present application.

[0095] Comparative Example 20 (e19) is R 1 has 18 carbon atoms, and R 1Compared with Example 9 (E8) in which the carbon number is 16, Comparative Example 20 has poor adhesion and does not reach a practical level. In Comparative Example 13 (e12), two methyl groups of Comparative Example 20 are changed to ethyleneoxy groups, and in Comparative Example 14 (e13), two methyl groups of Comparative Example 20 are changed to ethyl groups, and both of them also have poor adhesion and do not reach a practical level.

[0096] Comparative Example 21 (e20) is R 1 has 6 carbon atoms, and R 1 Compared with Example 8 (E7) in which the number of carbon atoms is 8, Comparative Example 21 has poor adhesion and does not reach a practical level.

[0097] Comparative Example 23 (e22) is a pitch control agent disclosed as the best mode in Patent Document 5, but compared with Examples 1 to 9, it is significantly inferior in both the amount of remaining pitch and the adhesiveness.

[0098] As a result of the above, the use of the compound of general formula (1) of the present invention shows a tendency to suppress pitch generation compared to conventional pitch control agents, and furthermore, by suppressing the stickiness of the pitch, it is possible to suppress problems in the papermaking process, such as paper breakage, and problems in the processing process.

[0099] (Other embodiments) The above-described embodiments are merely examples of the present invention, and the present invention is not limited to these examples. These examples may be combined with well-known, commonly used, or publicly known technologies, or may be partially replaced. Modified inventions that would be easily conceived by a person skilled in the art are also included in the present invention.

Claims

1. A pitch control agent for suppressing pitch in rubber systems, characterized by containing a compound represented by general formula (1) 【Chemistry 1】 In formula (1), R １ is an alkyl group having 10 to 14 carbon atoms, and R ２ , R ３ is a methyl group, and R ４ is a hydroxyalkyl group having 2 to 4 carbon atoms, and X ｍ－ is a nitrate ion or a sulfate ion, and m is 1 to 3.

2. A method for controlling pitch, comprising adding a compound represented by general formula (1) according to claim 1 to a pulp or paper manufacturing process.

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