WO2019054730A2 - Procédé de production d'un agent de traitement de surface aqueux, et agent de traitement de surface aqueux ainsi obtenu - Google Patents

Procédé de production d'un agent de traitement de surface aqueux, et agent de traitement de surface aqueux ainsi obtenu Download PDF

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Publication number
WO2019054730A2
WO2019054730A2 PCT/KR2018/010646 KR2018010646W WO2019054730A2 WO 2019054730 A2 WO2019054730 A2 WO 2019054730A2 KR 2018010646 W KR2018010646 W KR 2018010646W WO 2019054730 A2 WO2019054730 A2 WO 2019054730A2
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Prior art keywords
surface treatment
weight
treatment agent
subject
group
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PCT/KR2018/010646
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English (en)
Korean (ko)
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WO2019054730A3 (fr
WO2019054730A9 (fr
Inventor
민철희
정용배
이인혁
Original Assignee
주식회사 엘지하우시스
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Priority claimed from KR1020170156793A external-priority patent/KR102202657B1/ko
Application filed by 주식회사 엘지하우시스 filed Critical 주식회사 엘지하우시스
Priority to CN201880057135.8A priority Critical patent/CN111065775A/zh
Priority to US16/641,935 priority patent/US11739476B2/en
Publication of WO2019054730A2 publication Critical patent/WO2019054730A2/fr
Publication of WO2019054730A3 publication Critical patent/WO2019054730A3/fr
Publication of WO2019054730A9 publication Critical patent/WO2019054730A9/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60N—SEATS SPECIALLY ADAPTED FOR VEHICLES; VEHICLE PASSENGER ACCOMMODATION NOT OTHERWISE PROVIDED FOR
    • B60N2/00—Seats specially adapted for vehicles; Arrangement or mounting of seats in vehicles
    • B60N2/58—Seat coverings
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
    • D06N3/04—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06N3/06—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds with polyvinylchloride or its copolymerisation products

Definitions

  • the present invention relates to a process for producing an aqueous surface treatment agent and an aqueous surface treatment agent prepared therefrom, and more particularly to an aqueous surface treatment agent for forming a surface treatment layer of artificial leather used for an automotive seat cover,
  • the present invention relates to a method for producing an aqueous surface treatment agent which does not cause development and an aqueous surface treatment agent prepared therefrom.
  • the conventional artificial leather comprises a laminated structure including a back layer, a foam layer, a skin layer, and a surface treatment layer from the bottom.
  • the surface treatment layer is formed by coating the surface of the skin layer with a surface treatment agent.
  • a surface treatment agent When the surface treatment layer is formed using a conventional oily surface treatment agent, the surface treatment layer may have an unpleasant odor due to volatile organic chemicals (VOCs)
  • VOCs volatile organic chemicals
  • Patent Document 1 KR 10-1995-0018350 A (Publication date: July 22, 1995)
  • the present invention has been made in view of the above problems, and it is an object of the present invention to provide a method for producing an aqueous surface treatment agent which does not cause whitening on the surface of artificial leather.
  • step (c) adding the mixture of step (a) to the mixture of step (b) and stirring the mixture; And a method for producing the aqueous surface treatment agent.
  • the present invention also provides an aqueous surface treatment agent prepared from the method for producing the aqueous surface treatment agent.
  • the aqueous surface treatment agent prepared from the aqueous surface treatment agent preparation method of the present invention has the effect of preventing whitening on the surface of artificial leather.
  • the aqueous surface treatment agent prepared from the aqueous surface treatment agent of the present invention has an excellent antifouling property as compared with the conventional oily surface treatment agent, but also significantly reduces the amount of VOCs generated and has an excellent coating property.
  • FIG. 1 is a photograph showing the degree of liquid penetration when measuring the surface tension of a surface treatment layer formed using an oil-based surface treatment agent.
  • FIG. 2 is a photograph showing the degree of liquid penetration when measuring the surface tension of the surface treatment layer formed using the aqueous surface treatment agent according to the present invention.
  • step (c) adding the mixture of step (a) to the mixture of step (b) and stirring the mixture; To a method for producing an aqueous surface treatment agent.
  • the step (a) may be a step of adding the curing agent (B) to the aqueous solvent (C) followed by stirring at 20 to 30 ° C or 23 to 26 ° C for 40 minutes to 5 hours or for 1 to 3 hours. If the stirring is performed for less than the time, the aqueous solvent (C) and the curing agent (B) are not sufficiently stirred, and then the unreacted curing agent (B) So that the surface bridging density and workability are lowered and whitening phenomenon occurs on the surface of the artificial leather. Therefore, it is necessary to sufficiently stir for the above time.
  • the whitening phenomenon refers to a white dot defect of a white dot appearing in the middle of the surface of the artificial leather after application of the aqueous surface treatment agent.
  • the aqueous solvent (C) may be water or an alcohol or a mixture of water and an alcohol.
  • the alcohol may be at least one selected from the group consisting of alcohols such as methanol, ethanol, propanol, butanol, and the like. Due to the alcohol, stability of the reaction during mixing of the components constituting the aqueous surface- And the stability of the treating agent is ensured.
  • aqueous solvent (C) Due to the aqueous solvent (C), it is possible to form an interpenetrating polymer network intertwined with the curing agent not participating in the three-dimensional crosslinking reaction of the subject (A), and volatile organic compounds It is possible to reduce the generation of odorous substances depending on the VOCs.
  • the aqueous solvent (C) may be contained in an amount of 1-25 parts by weight, 5-20 parts by weight, or 10-20 parts by weight based on 100 parts by weight of the subject (A).
  • the curing agent (B) added to the aqueous solvent (C) in the step (a) may contain at least one functional group selected from the group consisting of an aziridine group, an isocyanate group, and a carbodiimide group per molecule .
  • the compound having an aziridine group refers to a compound containing a heterocyclic tricyclic ring composed of two carbon atoms and one nitrogen atom, and includes 3- (3-methoxyphenyl) -3- (trifluoromethyl) 3- (3-methoxyphenyl) -3-trifluoromethyl) -diaziridine); 3- (trifluoromethyl) -3-phenyldiaziridine (3- (trifluoromethyl) -3-phenyldiaziridine); Propane-2,2-diyldi zenzene-4,1-diyl diaziridine-1-carboxylate; 1,1 '- (butylphosphoryl) diaziridine; 1,1' - (butylphosphoryl) diaziridine; Oxydiethane-2,1-diyldiaziridine-1-carboxylate; oxydiethane-1, < / RTI > 3,3
  • the isocyanate group-containing compound is, for example, selected from the group consisting of toluene diisocyanate, diphenylmethane diisocyanate, modified diphenylmethane diisocyanate, naphthalene diisocyanate, phenylene diisocyanate, hexamethylene diisocyanate, lysine isocyanate, cyclohexane diisocyanate, -Isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate, isophorone diisocyanate, methylenediphenyl isocyanate, xylene diisocyanate, tetramethyl xylene diisocyanate, norbornene diisocyanate, triphenyl methane triisocyanate, poly Phenylpolymethylene polyisocyanate, polyisocyanate containing carbodiimide group, polyisocyanate containing allophanate group, poly
  • the compound having the carbodiimide group may be a polycarbodiimide.
  • the curing agent (B) may be contained in an amount of 1-25 parts by weight, 5-20 parts by weight, or 10-20 parts by weight based on 100 parts by weight of the subject (A). If it is contained in the above range, it is uncured and physical properties such as light resistance, heat resistance, scratch resistance, abrasion resistance, solvent resistance and hydrolysis resistance are lowered, The ductility is deteriorated, so that the mixing can be carried out within the above range.
  • the step (b) may be a step of stirring the subject (A), the silicone compound (D) and additives at 20-30 ° C or 23-26 ° C.
  • the subject (A) is as follows.
  • the subject (A) contained in the aqueous surface treatment agent of the present invention is a polyurethane having at least one functional group selected from the group consisting of a carboxylic acid group, a hydroxyl group, an amino group, and a combination thereof per molecule dispersed in an aqueous solvent (A-1).
  • a method for producing a polyurethane having a carboxylic acid group in the polyurethane for example, a method in which a compound having a carboxylic acid group is used as a raw material in the urethane formation reaction can be mentioned.
  • the compound having a carboxylic acid group used as a raw material of the polyurethane include 2,2'-dimethylolpropionic acid, 2,2'-dimethylolbutanoic acid, 2,2'-dimethylolbutyric acid, 2,2'-dimethyl And allpentanoic acid.
  • Examples of the method for producing a polyurethane having a hydroxy group in the polyurethane include a method of reacting an excessive amount of a polyol and / or a glycol with a polyisocyanate to obtain a polyurethane having a hydroxy group at the terminal.
  • Examples of the compound having a hydroxy group used as a raw material of the polyurethane include polyester polyol, polyether polyol, polycarbonate polyol, polyacetal polyol, polyacrylate polyol, polyester amide polyol, polythioether polyol, polybutadiene , And the like.
  • an amino alcohol such as 2-aminoethanol, 2-aminoethylethanolamine or diethanolamine, aminophenol or the like is reacted with a urethane prepolymer at the terminal of the isocyanate group To obtain a polyurethane having an amine group.
  • the polyurethane may preferably be a polycarbonate-based polyurethane which uses the polycarbonate polyol having excellent heat resistance and light resistance as a raw material.
  • the polyurethane content in the subject (A-1) may be 5-30% by weight, or 10-25% by weight.
  • the polyurethane content in the subject (A-1) is less than the above-mentioned range, the touch feeling, scratch resistance, light resistance, heat resistance, abrasion resistance and solvent resistance are lowered. If the polyurethane content exceeds the above range, whitening phenomenon and appearance unevenness And may be included within the above range.
  • the subject (A) may be an acrylic-modified polyurethane further containing acrylate in the main chain dispersed in an aqueous solvent (A-2).
  • the acrylic-modified urethane content in the subject (A-2) may be 1-10% by weight, or 2-8% by weight.
  • the content of the acryl-modified urethane in the subject (A-2) is less than the above range, the stain resistance and touch feeling slip, and when the content exceeds the above range, the ductility is lowered and the touch feeling is dry, .
  • the above-mentioned subject (A-2) may further include a siloxane for facilitating water dispersion of the acrylic-modified polyurethane and improving the antifouling effect.
  • the siloxane contains one or more methyl groups, thereby securing an antifouling effect, and securing excellent compatibility with an acryl-modified polyurethane and excellent hardness.
  • the siloxane may be included in the subject (A-2) in an amount of 0.01 to 2% by weight, or 0.05 to 1.5% by weight. If the amount is less than the above range, the antifouling effect is lowered. If the amount exceeds the above range, the siloxane is transferred to the surface and the surface of the artificial leather becomes excessively glossy. When the surface of the artificial leather is rubbed by hand, It may be within the content range.
  • subject A of the present invention may be a mixture of subject A-1 and subject A-2.
  • the subject matter (A-1) and the subject matter (A-2) may be mixed at a weight ratio of 1: 9-4: 6 or 2: 8-3: 7.
  • the subject A-1 is less than the above range, the surface texture of the artificial leather is not smooth, and when the subject A-1 exceeds the above range, the antifouling effect is lowered.
  • the silicone compound (D) may be in the form of a liquid in which the polysiloxane is dispersed in water or may be a polysiloxane in the form of beads, but may be in the form of a liquid .
  • the content of the polysiloxane in the liquid silicone compound may be 5-30 wt%, or 10-20 wt%.
  • the silicone compound may be contained in an amount of 1-15 parts by weight, 1-10 parts by weight, or 5-7 parts by weight based on 100 parts by weight of the main component (A).
  • the Squeak index is a numerical value of the noise generated in the friction between the artificial leather and the human body, that is, the occupant.
  • the artificial leather specimen is superimposed on the artificial leather specimen by using a universal testing machine, And the force deviation (DELTA F) and the average force (Fa) required to pull at a speed of 100 mm / min are measured, and the Squeak index can be calculated by DELTA F / Fa.
  • the Squeak index satisfies the above-mentioned range of less than 0.15 or not more than 0.14, so that the noise is small and the touch feeling is smooth.
  • the Squeak index may be within the above range because noise is strong and the stick slip characteristic, which is a friction phenomenon accompanying vibration, is strong.
  • the dynamic friction coefficient ( ⁇ ) is a slip property when an object moves while sliding on another object.
  • the artificial leather specimen is stacked on top of each other by using a universal material tester and pressed at a weight of 4.5 kg (W) min to measure the average force (Fa) required to pull the friction coefficient to Fa / W can be measured.
  • the coefficient of dynamic friction may be 0.2-0.5 or 0.25-0.5. If it is less than the above range, the slippery property can not be maintained and the seizure feeling is not good. If the above range is exceeded, the Squeak index increases due to the friction between the artificial leather and the passenger.
  • the additive may be a defoaming agent or a leveling agent.
  • the antifoaming agent may be selected from a silicone resin, a surfactant, a paraffin wax or a mineral oil to prevent a large number of air bubbles from being generated due to the high viscosity of the aqueous surface treating agent as compared with the oil surface treatment agent. Do not.
  • the antifoaming agent may be included in an amount of 0.1-0.5 parts by weight based on 100 parts by weight of the subject (A). When the amount is less than the above range, a large number of bubbles are generated when coating the aqueous surface treatment agent, resulting in deterioration in workability. When the amount exceeds the above range, the defoaming agent falls within the above range.
  • the leveling agent is added so that the surface coating can be made uniform, and may be selected from silicone resin or acrylic resin, but is not limited thereto.
  • the leveling agent may be included in an amount of 1 to 5 parts by weight based on 100 parts by weight of the main component (A). If the amount is less than the above range, the surface coating may not be uniform during the coating of the aqueous surface treatment agent, and when it exceeds the above range, the physical properties may be deteriorated.
  • one or more other additives selected from the group consisting of urethane beads, acrylic beads and fluorine-containing wax may be further mixed.
  • the antifouling effect can be realized by hydrophobicity, and the surface tension of the aqueous surface treatment agent can be reduced to further impart slipperiness.
  • the other additives may be contained in the aqueous surface treatment agent in an amount of 1-10% by weight, or 2-5% by weight. By including the other additives within the above range, it is possible to reduce the occurrence of problems of dyes and dyes of other materials in the aqueous surface treatment agent, and the effect of surface energy reduction can be easily realized.
  • the aqueous surface treatment agent may further include at least one selected from the group consisting of a surfactant, a cosolvent, a modifier, a quencher, a gloss enhancer, a thickener and a quencher, And is not particularly limited.
  • the step (c) may include stirring the mixture of step (a) and the mixture of step (b) at 20-30 ° C or at 23-26 ° C for 0.2-1 hours, or for 0.3-0.8 hours .
  • the present invention also relates to an aqueous surface treatment agent prepared from the method for producing the aqueous surface treatment agent.
  • the viscosity of the aqueous surface treatment agent prepared by the above-described method may be 150-700 cps or 200-600 cps at 25 ° C. If it is less than the above range, the texture of the artificial leather is not smooth and relatively stiff, The coating efficiency is lowered, and when it exceeds the above range, gravure coating is not possible, so that it can have a viscosity within the above range.
  • the viscosity of the aqueous surface treatment agent is higher than that of the conventional oily surface treatment agent, and the coating of the upper part of the skin layer is effected with high viscosity.
  • the aqueous surface treatment agent prepared by the above-described method can be applied on the artificial leather substrate and dried at 110-150 ° C or 130-150 ° C for 80-120 seconds to evaporate the aqueous solvent to form a synthetic leather surface have.
  • the drying time is less than the above temperature and time range, the aqueous solvent remains not evaporated. As a result, the surface of the artificial leather is whitened due to the uncured state, and the surface properties of the artificial leather are deteriorated. May be lowered to cause discoloration of the aqueous surface treatment agent, so that drying may be performed within the above temperature and time range.
  • the aqueous surface treatment agent prepared by the above-mentioned production method can be obtained by mixing a curing agent (B) to the aqueous solvent (C), stirring it sufficiently and then mixing with the subject (A)
  • the surface hardening effect of the surface treatment layer and the surface crosslinking density can be increased while the surface tension can be lowered because the hardening agent not participating in the dimensional crosslinking reaction can form an intertwined interpenetrating polymer network.
  • the aqueous surface treatment agent prepared from the aqueous surface treatment agent of the present invention has an excellent antifouling property as compared with the conventional oily surface treatment agent, and has an effect of significantly reducing the amount of VOCs generated.
  • the surface of artificial leather coated with the aqueous surface treatment agent produced by the above-described production method has an effect of preventing whitening.
  • Example 2 The same composition and manufacturing method as in Example 1, except that a polycarbonate-based polyurethane resin containing 60% by weight of water, 7% by weight of acryl-modified urethane and 0.15% by weight of siloxane was used as a subject in the step (b) To prepare an aqueous surface treatment agent.
  • Example 2 The same composition and manufacturing process as in Example 1 were used, except that the polycarbonate-based polyurethane resin in which the subject of Example 1 and the subject of Example 2 were mixed at a weight ratio of 2: 8 was used as the subject in the step (b) To prepare an aqueous surface treatment agent.
  • An oil-based surface treatment agent containing 95% by weight of urethane acrylate as a subject and 5% by weight of methylenedicyclohexyl diisocyanate as a curing agent was prepared.
  • An aqueous surface treating agent was prepared in the same manner as in Example 1, except that the curing agent was added to the aqueous solvent in the step (a) and stirred at 25 ° C for 0.5 hour.
  • An aqueous surface treatment agent was prepared in the same manner as in Example 1, except that 30 parts by weight of a curing agent was added to 20 parts by weight of the aqueous solvent in the step (a).
  • An aqueous surface treatment agent was prepared in the same manner as in Example 1, except that an aqueous solvent was added to the curing agent in the step (a).
  • aqueous surface treatment agent was prepared in the same manner as in Example 1, except that in step (a), the base and the curing agent were first stirred and then an aqueous solvent was added to the mixture.
  • the surface treatment agents of Examples 1-3, Comparative Example 1 and Reference Example 1-4 prepared in 1 above were coated on a substrate and dried at 140 ° C for 90 seconds to prepare a specimen including a surface treatment layer on the substrate Respectively.
  • a specimen including the surface treatment layer was prepared in the same manner as in Example 1, except that the aqueous surface treatment agent prepared in Example 1 was coated on the substrate and dried at 100 ° C.
  • the specimen prepared in the above 2 was mounted on a universal wear tester (Toyoseiki), a piece of Cotton Soil Test Cloth was placed on the specimen, and a constant load of 0.9 kg was applied.
  • the contaminated specimen is placed on the opening of the colorimeter and a green filter is mounted to measure the reflection value of the uncontaminated portion of the specimen.
  • the average value (%) of staining was calculated by measuring the reflection value (%) at the intermediate polished portion between the center and the outer edge of the stained portion.
  • VOCs volatile organic compounds
  • the amount of volatile organic compounds (VOCs) generated was prepared as described above, and the specimen was placed in a desiccator, which was a 4-liter glass container, and was sealed and heated in an oven for 2 hours. Thereafter, the sample was allowed to stand in a laboratory at 25 ° C for 1 hour, and the lid of the desiccator was opened for about 3 cm to 4 cm. Volatile organic compounds (VOCs) emitted from the specimen were collected and the amount of the generated volatile organic compounds (VOCs) was measured by a measuring instrument.
  • VOCs volatile organic compounds
  • the surface cross-link density is determined by measuring the amount of cross-linked urethane that does not dissolve in boiling xylene or decahydronaphthalene.
  • the specimen is weighed up to 1 mg with a chemical balance (m1), and then placed on a mesh or metal plate with a hole. Subsequently, the container is placed in boiling xylene or decahydronaphthalene, and left for 6-8 hours.
  • the container with the residue is removed from the boiling solvent, cooled to room temperature, and dried, and the residual amount (m2) is weighed to 1 mg.
  • Viscosity was measured using a Brookfield viscometer.
  • the temperature of the surface treatment agent is brought to 25 ° C., and the surface treatment agent is placed in a 600 mm or more wide cylindrical container. Then, a spindle No. 64 is placed in the center of the surface treatment agent vessel.
  • the panel was composed of three or more persons and the odor was directly evaluated.
  • Table 1 shows the odor according to the direct sensory evaluation. It is divided into 6 steps from 1 to 6, It shows that it is flying badly.
  • Odor too Smell / expression of odor One No odor. 2 Almost undetectable odor. 3 The smell is weakly detected and does not disintegrate. 4 The odor is easily detected and somewhat disgusting. 5 Strong smell and disgust. 6 Stimulating and intense smell.
  • the whitening phenomenon visually confirmed the presence or absence of white dots on the synthetic leather surface (surface treatment layer).
  • the aqueous surface treatment agents of Examples 1 to 3 prepared by the aqueous surface treatment agent preparation method of the present invention had antifouling properties as compared with Comparative Example 1 in which the oily surface treatment agent was applied, It can be confirmed that the amount of VOCs generated is remarkably reduced, the odor is not disintegrated, and the coating on the upper part of the substrate is good with high viscosity.
  • an aqueous solvent in Reference Example 1 in which the aqueous solvent and the curing agent are not sufficiently stirred, an aqueous solvent In Reference Example 3, in which Reference Example 4 in which the base and the curing agent were stirred first, whitening occurred and the surface cross-link density was lowered.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Aviation & Aerospace Engineering (AREA)
  • Transportation (AREA)
  • Mechanical Engineering (AREA)
  • Paints Or Removers (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)

Abstract

La présente invention concerne un procédé de production d'un agent de traitement de surface aqueux, et un agent de traitement de surface aqueux ainsi obtenu et, plus particulièrement, un procédé de production d'un agent de traitement de surface aqueux, et un agent de traitement de surface aqueux ainsi obtenu, où l'agent de traitement de surface aqueux est utilisé pour former une couche de traitement de surface de cuir artificiel pour revêtements de sièges de véhicules, caractérisée en ce qu'un phénomène de blanchiment ne se produit pas sur la surface dudit cuir artificiel.
PCT/KR2018/010646 2017-09-14 2018-09-11 Procédé de production d'un agent de traitement de surface aqueux, et agent de traitement de surface aqueux ainsi obtenu WO2019054730A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201880057135.8A CN111065775A (zh) 2017-09-14 2018-09-11 水性表面处理剂的制备方法以及由此制备的水性表面处理剂
US16/641,935 US11739476B2 (en) 2017-09-14 2018-09-11 Method of preparing water-based surface treatment agent and water-based surface treatment agent prepared using the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2017-0117553 2017-09-14
KR20170117553 2017-09-14
KR1020170156793A KR102202657B1 (ko) 2017-09-14 2017-11-22 수성 표면처리제 제조방법 및 이로부터 제조된 수성 표면처리제
KR10-2017-0156793 2017-11-22

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WO2019054730A2 true WO2019054730A2 (fr) 2019-03-21
WO2019054730A3 WO2019054730A3 (fr) 2019-05-09
WO2019054730A9 WO2019054730A9 (fr) 2019-06-27

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DE4413562A1 (de) * 1994-04-19 1995-10-26 Herberts Gmbh Wäßrige Dispersion von Siloxanbrücken enthaltenden Polyurethanen, deren Herstellung und Verwendung in Überzugsmitteln
KR100649432B1 (ko) * 2005-02-23 2006-11-27 조광페인트주식회사 수분산성 자외선 경화형 폴리우레탄 아크릴레이트수지의 제조방법 및 그 도료 조성물
KR20120126814A (ko) * 2011-05-13 2012-11-21 주식회사 화승티엔씨 고무 표면 처리용 수성 도료의 조성물
KR101470611B1 (ko) * 2014-04-02 2014-12-15 (주)인코켐 실리콘계 고무 표면 처리용 도료 조성물 및 그 제조방법
KR20150117313A (ko) * 2014-04-09 2015-10-20 수산고분자 주식회사 아크릴 변성 폴리우레탄 수분산 조성물, 및 이의 용도

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