KR20140072371A - Flame-retardant polyester composition and manufacturing method thereof - Google Patents
Flame-retardant polyester composition and manufacturing method thereof Download PDFInfo
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- KR20140072371A KR20140072371A KR1020120139083A KR20120139083A KR20140072371A KR 20140072371 A KR20140072371 A KR 20140072371A KR 1020120139083 A KR1020120139083 A KR 1020120139083A KR 20120139083 A KR20120139083 A KR 20120139083A KR 20140072371 A KR20140072371 A KR 20140072371A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
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Abstract
Description
The present invention relates to a flame retardant polyester composition and a method for producing the flame retardant polyester composition. More particularly, the present invention relates to a flame retardant polyester composition including a non-halogen flame retardant and having high flame retardancy.
In general, polyester is excellent in mechanical and thermal properties, moldability and chemical resistance, and is applied not only to automobiles, electric and electronic devices, office equipment, but also to a wide range of fields such as fibers and films. In particular, polyethylene terephthalate resin has been widely used as various composite materials for automobiles, electric and electronic parts and the like because of its excellent economy, heat resistance, chemical resistance, electrical characteristics, mechanical strength and molding processability, and its usage is increasing.
However, since polyester has a burning property, it has a great risk of fire when used in molded articles such as fiber, electric and electronic products, and can prevent the combustion effect when a fire occurs in order to prevent a large fire accident Flame retardancy is required. Accordingly, development has been made to impart flame retardancy to the polyester resin by various methods.
Conventionally, flame retardancy has been imparted by a method in which an organic halogen flame retardant or an auxiliary flame retardant is separately added to a polyester resin. However, the halogen-based flame retardant containing chlorine or bromine has problems such as corrosion of the processing equipment by the hydrogen halide and decomposition of the resin. In addition, toxic gases caused by a large amount of halogenated compounds generated during a fire caused damage to people and property. In addition, when a resin composition containing an organic halogen flame retardant or a flame retardant aid is actually applied, the metal which is in contact with the molded article is corroded to hinder the action of the component. For example, the contact metal of an electrical contact part is easily contaminated and causes a change in electrical resistance value.
On the other hand, some European countries have proposed regulations on the use of flame retardants such as polybrominated biphenyl (PBB) and polybrominated biphenylether (PBDE) in order to prevent dioxin from burning and incineration. And there has been an attempt to strictly restrict the use of a part of harmful metals and brominated flame retardants and antimony compounds according to the evaluation of environmental stability in automobiles and electric and electronic parts. With such a movement, it is urgently required to develop a technique for a non-halogen flame retardant.
As a study on such a non-halogen flame retardant polyester resin, there has been disclosed a composition in which a thermoplastic polyester resin is added, an inorganic and an inorganic filler are used together, or a phosphoric acid and a phosphoric acid ester are used together. However, In order to obtain a desired level of flame retardancy, a large amount of a flame retardant is required. In particular, a flame retardant containing a phosphorus generates phosphine gas even by a small amount of water contact during processing due to deterioration in high temperature stability. Due to the red coloration, there are restrictions on the implementation of product colors.
Further, a flame retardant composition in which an organophosphorus flame retardant and a cyanuric acid adduct are added to a thermoplastic polyester resin and a glass fiber and an inorganic filler are used and a halogen-free flame retardant composition is disclosed. In this case, a large amount of a phosphorus flame retardant is used And the viscosity of the resin composition is increased and the mechanical strength of the molded article is lowered. In addition, the use of a large amount of a flame retardant has a disadvantage of causing an excessive increase in cost, a decrease in physical properties, a decrease in heat resistance, and a decrease in electrical characteristics.
SUMMARY OF THE INVENTION The present invention has been conceived to solve the above-mentioned problems, and an object of the present invention is to provide a flame retardant composition which is environmentally friendly, including a halogen-free flame retardant and has improved flame retardancy, And a flame retardant polyester composition excellent in heat resistance. Further, it is intended to provide a flame retardant polyester composition which is excellent in spinnability and is suitable for producing polyester fibers.
In order to solve the above-described problems,
Wherein the flame retardant comprises a phosphorus-based flame retardant and a nitrogen-containing flame retardant, the mixing weight ratio of the phosphorus flame retardant and the nitrogen-containing flame retardant is 9: 1 to 6: 4, And 15 to 20% by weight of the flame retardant polyester composition.
According to a preferred embodiment of the present invention, the phosphorus flame retardant is selected from the group consisting of phosphate, phosphonate, phosphinate, phosphine oxide, and phosphazene And may include any one or more selected.
According to another preferred embodiment of the present invention, the nitrogen-containing flame retardant is selected from the group consisting of melamine, melamine cyanurate, triphenylisocyanurate, melamine phosphate, melamine pyrophosphate, ammonium polyphosphate, alkylamine phosphate and piperidine acid polyphosphate , And the like.
According to another preferred embodiment of the present invention, the polyester may have an intrinsic viscosity (IV) of 0.6 to 0.8 dl / g.
According to another preferred embodiment of the present invention, the flame retardant polyester composition is a flame retardant polyester composition which is a silicone flame retardant, a lubricant, an antioxidant, a light stabilizer, a hydrolysis stabilizer, a release agent, a pigment, an antistatic agent, And may further comprise at least one additive selected from the group consisting of a mineral filler, a crosslinking agent, an antibacterial agent, a processing aid, a metal deactivator, a suppressing agent, a fluorine antistatic agent, an antiwear friction agent, and a coupling agent.
Further, the present invention provides a fiber produced using the above-mentioned flame retardant polyester composition.
The present invention also provides a process for producing a flame retardant polyester composition for producing a flame retardant polyester composition by polymerizing a polycarboxylic acid and a polyhydric alcohol in the presence of a flame retardant.
According to a preferred embodiment of the present invention, the flame retardant may be prepared by mixing a flame retarder powder having an average particle size of 0.03 to 0.8 μm with a polyhydric alcohol to form a slurry with a viscosity of 0.01 to 0.1 g / cm 3 .s.
According to another preferred embodiment of the present invention, the flame retardant comprises 5 to 20% by weight of the total composition, the flame retardant includes a phosphorus-based flame retardant and a nitrogen-containing flame retardant, and the mixing weight ratio of the phosphorus- 9: 1 to 6: 4.
According to another preferred embodiment of the present invention, the flame retardant polyester composition may have a residual amount of inorganic material of 15 to 20% by weight when heated up to 900 캜.
According to another preferred embodiment of the present invention, the phosphorus-based flame retardant is selected from the group consisting of phosphate, phosphonate, phosphinate, phosphine oxide, and phosphazene And the like.
According to another preferred embodiment of the present invention, the nitrogen-containing flame retardant is selected from the group consisting of melamine, melamine cyanurate, triphenylisocyanurate, melamine phosphate, melamine pyrophosphate, ammonium polyphosphate, alkylamine phosphate and poly Phosphate, and the like.
The flame retardant polyester composition of the present invention is environmentally friendly including a non-halogen flame retardant and has excellent flame retardancy and excellent strength and heat resistance while reducing the content of the flame retardant and improving the formation of carbide. In addition, it has excellent processability, formability and mechanical properties, and is suitable for manufacturing various molded articles such as automobiles, electric / electronic parts, office equipment, etc., and is excellent in radioactivity and can be usefully used for producing flame retardant polyester fiber.
Hereinafter, the present invention will be described in more detail.
As described above, a conventional polyester composition containing a halogen-based flame retardant has a problem that it generates toxic halogen gas during a fire and corrodes the metal in contact with the molded article, thereby hindering the operation of the component. Further, in the case of a conventional polyester composition containing a non-halogen flame retardant, a large amount of a flame retardant is required in order to obtain a desired level of flame retardancy, resulting in an increase in the viscosity of the resin composition and a decrease in mechanical strength of the molded article. And heat resistance is decreased.
In the present invention, the flame retardant comprises 5 to 20% by weight of the flame retardant, and the phosphorus-containing flame retardant and the nitrogen-containing flame retardant are mixed in a weight ratio of 9: 1 to 6: 4, The present invention has been made to solve the above-mentioned problems by providing a flame retardant polyester composition having a residual amount of an inorganic substance of 15 to 20% by weight upon heating. Accordingly, it is possible to provide a flame retardant polyester composition which is environmentally friendly including a non-halogen flame retardant, has an improved flame retardant performance while reducing the content of the flame retardant, and has excellent strength and heat resistance. In addition, it has excellent processability, moldability, and mechanical properties, and is excellent in radioactivity and can be usefully used for producing flame retardant polyester fibers.
The polyester used in the composition of the present invention can be synthesized by polymerizing at least one aromatic, aliphatic or alicyclic polycarboxylic acid compound and at least one aliphatic or alicyclic polyhydric alcohol. Preferably, the aromatic polycarboxylic acid is composed of 6 to 20 carbon atoms, and the aliphatic or alicyclic polycarboxylic acid is composed of 3 to 20 carbon atoms. Aliphatic or cycloaliphatic polyhydric alcohols comprise from 2 to 20 carbon atoms. More preferably, polyethylene terephthalate, polypropylene terephthalate or polybutylene terephthalate may be used alone or in combination, and most preferably polyethylene terephthalate. In consideration of the processability and mechanical properties of the polyester, the intrinsic viscosity (IV) of the polyester is preferably 0.6 to 0.8 dl / g.
The method of producing a polyester by using a polycarboxylic acid and a polyhydric alcohol can be generally carried out in two stages of an esterification reaction and a polycondensation reaction, and a usual method known in the art can be used.
Examples of the polyvalent carboxylic acid compound that can be used in the present invention include terephthalic acid, isophthalic acid, 1,4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, succinic acid, glutaric acid, adipic acid, Naphthalene dicarboxylic acid, 4,4'-biphenyldicarboxylic acid, or 4,4'-biphenyl dicarboxylic acid. - dibenzyl dicarboxylic acid, and the like, but not limited thereto, and preferable polyvalent carboxylic acid compounds may be terephthalic acid, isophthalic acid, or a mixture thereof.
Examples of the polyhydric alcohol include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,2- , 2-, 1,3-, or 1,4-cyclohexanedimethanol, neopentyl glycol, or 2,2,4,4-tetramethyl-1,3-cyclobutanediol, but are not limited thereto, Preferred polyhydric alcohols may be ethylene glycol, cyclohexanedimethanol or mixtures thereof.
In the flame retardant polyester composition of the present invention, the polyvalent carboxylic acid and the polyhydric alcohol are polymerized in the presence of a flame retardant to prepare a flame retardant polyester composition.
The flame retardant polyester composition is prepared by adding a flame retardant during the step of polymerizing the polycarboxylic acid and the polyhydric alcohol, thereby improving the dispersibility of the flame retardant and enhancing the formation of carbide to improve flame retardancy. Therefore, the flame retardant polyester composition of the present invention can satisfy the residual amount of the inorganic material in the range of 15 to 20% by weight when heated up to 900 캜.
The increase in the residual amount of the inorganic material means that the Char forming property is excellent, and the excellent Char forming property means that the condensed phase flame retardant function is excellent.
Phosphorous flame retardants exhibit flame retardant functionality in a gas phase and a condensed phase. The gas phase acts to inactivate the active radicals in the gaseous state, such as halogen flame retardants, while the condensed phase, Char is formed to form a nonflammable layer on the surface to physically block the heat transfer into the polymer resin and the supply of fuel to the combustion region. The nitrogen-containing flame retardant agent is a phosphorus-based flame retardant which forms carbonic acid-phosphoric acid amide, promotes dehydrogenation reaction and dehydration reaction, promotes carbonization, and improves flame retardancy.
The flame retardant polyester composition of the present invention can impart uniform flame retardancy by mixing the phosphorus flame retardant and the nitrogen-containing flame retardant in a mixing weight ratio of 9: 1 to 6: 4 by introducing the flame retardant into the polyester polymerization process to improve dispersibility , The Char forming property is improved and the residual amount of the inorganic material is increased. When heating up to 900 ° C, the residual amount of inorganic material can be satisfied by 15 to 20% by weight.
If the residual amount of the inorganic material is less than 15% by weight when heated up to 900 캜, flame retardancy is insufficient. If it exceeds 20% by weight, foreign substances may be generated in the filter during spinning, and the pack pressure may increase.
A mixture of a flame retardant powder having an average particle size of 0.03 to 0.8μm and a polyhydric alcohol to the improvement of flame retardant dispersed in the slurry in an amount of 0.01 to 0.1g / cm 3 .s viscosity screen can be added during the polyester polymerization process. As described above, the flame retardant is mixed with polyhydric alcohol and made into a slurry, and when added during the polyester polymerization process, the dispersibility is remarkably improved, the flame retardancy can be remarkably improved, the radioactivity is also excellent, and flame retardant polyester fiber can be produced . When the viscosity of the slurry containing the flame retardant added during the polyester polymerization process is less than 0.01 g / cm 3 .s, there is a disadvantage that the amount of the byproducts which adversely affects the fiber strength and dyeing property is increased sharply , And when it exceeds 0.1 g / cm 3 .s, the dispersibility is remarkably lowered and aggregates may be generated.
In addition, the flame retardant contained in the flame retardant polyester composition of the present invention includes a phosphorus-based flame retardant and a nitrogen-containing flame retardant that are not halogen-based flame retardants in order to impart environment-friendly flame retardancy.
The phosphorus flame retardant may be a phosphorus, a phosphonate, a phosphinate, a phosphine oxide, or a phosphazene, either alone or in combination. Preferably, triphenyl phosphate (TPP), trixylenyl phosphate (TXP), tricresyl phosphate (TCP) and the like can be mainly used. (RDP), phenyl diresorcinyl phosphate, cresyl diphenyl phosphate, xylenyldiphenyl phosphate, phenyldiglycidyl phosphate, and the like. Phenyl di (isopropylphenyl) phosphate) and the like can be used.
The nitrogen-containing flame retardant is a compound having a triazine structure, such as melamine, melamine cyanurate or triphenylisocyanurate, and melamine phosphate as a nitrogen-phosphorus-containing flame retardant. Melamine pyrophosphate, ammonium polyphosphate, alkylamine phosphate, and piperazine acid polyphosphate. These may be used singly or in combination.
The phosphorus flame retardant and the nitrogen-containing flame retardant are contained in a mixing weight ratio of 9: 1 to 6: 4, and the total content of the flame retardant in the total polyester composition is 5 to 20 wt%.
When the content of the flame retardant is less than 5% by weight, the effect of increasing the flame retardancy is insufficient. When the content exceeds 20% by weight, the heat resistance is lowered, the viscosity of the composition is increased, and the radioactivity is lowered. The flame retardant of the present invention comprises a phosphorus-based flame retardant and a nitrogen-containing flame retardant, and the flame retardant of the present invention can exhibit excellent flame retardancy without using a large amount of flame retardant by incorporating it in a mixing weight ratio of 9: 1 to 6: 4. Accordingly, when heated up to 900 DEG C, the residual amount of the inorganic material may be in the range of 15 to 20 wt%. Further, the flame retardant polyester fiber can be produced because of its excellent radiation property, and excellent mechanical strength can be satisfied while having excellent flame retardancy. When the phosphorus flame retardant and the nitrogen-containing flame retardant are out of the above-mentioned mixing weight ratio, the residual amount of the inorganic material is reduced to less than 15% by weight, the flame retardancy is deteriorated and a large amount of flame retardant must be contained in order to achieve the aimed flame retardancy. There is a drawback that the radioactivity is lowered due to the increase of the pack pressure and the problem of color tone due to pyrolysis occurs in the radiopolymerization.
The flame retardant polyester composition as described above may contain a silicone-based flame retardant, a lubricant, an antioxidant, a light stabilizer, a hydrolysis stabilizer, a releasing agent, a pigment, an antistatic agent, a conductivity imparting agent, an EMI shielding agent, It may further include at least one additive selected from the group consisting of a filler, a crosslinking agent, an antibacterial agent, a processing aid, a metal deactivator, a suppressing agent, a fluorine antistatic agent, an antiwear friction agent, and a coupling agent.
Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples should not be construed as limiting the scope of the present invention, and should be construed to facilitate understanding of the present invention.
≪ Examples 1 to 6 >
A phosphorus flame retardant having an average particle diameter of 0.04 μm and a nitrogen-containing flame retarder powder were mixed with ethylene glycol at a weight ratio shown in Table 1 and slurried.
Terephthalic acid and ethylene glycol were added in a molar ratio of 1: 1.2, and a flame retardant was mixed into ethylene glycol to prepare a slurry, and a flame retardant was added. 400 ppm of lithium acetate was added as an esterification catalyst, and the temperature in the reactor was elevated from room temperature to 120 캜 over 30 minutes, and the temperature was raised to 250 캜 for 120 minutes while stirring. Subsequently, 300 ppm of phosphoric acid as a heat stabilizer and 300 ppm of antimony trioxide as a catalyst were added, and the pressure in the tube was gradually reduced to 0.5 mmHg over 40 minutes, and the reaction was carried out for 180 minutes while the temperature in the tube was raised to 280 ° C Stirring was stopped and made into pellets. The flame retardant polyester compositions of Examples 1 to 6 were prepared by drying and then molding by injection molding.
(g / cm 3 .s)
Weight ratio
≪ Examples 7 to 12 >
The procedure of Example 1 was repeated except that the compositions of Examples 1 to 6 were extruded and the flame-retardant polyester fibers were prepared by spinning without injection molding.
Specifically, the flame-retardant polyester compositions of Examples 1 to 6 were subjected to spinning at a stretch ratio of 3 times under conditions of a resin discharge amount of 33 g / min, a blending speed of 2,500 mpm, and a spinning temperature of 275 캜 to a melt emitter equipped with a 24-
≪ Comparative Example 1 &
Except that the phosphorus flame retardant and the nitrogen-containing flame retardant were not included.
≪ Comparative Examples 2 to 4 >
Except that the weight ratio of the phosphorus flame retardant and the nitrogen-containing flame retardant, and the content of the flame retarder were each as shown in Table 2.
≪ Comparative Examples 5 to 7 >
Except that the weight ratio of the phosphorus-containing flame retardant and the nitrogen-containing flame retardant and the content of the flame retarder were as shown in Table 2.
(g / cm 3 .s)
Weight ratio
≪ Comparative Examples 8 and 9 &
A flame retardant was produced in the same manner as in Examples 1 and 7, except that the flame retardant was slurried during the polyester polymerization and was not added, but the polyester and the flame retardant were mixed.
<Experimental Example>
1. Mineral residue
In order to measure the residual amount of the inorganic materials, the temperature was increased from room temperature to 750 ° C. under N 2 condition by 10 ° C./min and the temperature was raised by 10 ° C./min under the condition of 750 ° C. to 900 ° C. Air was measured using TA Instruments and DISCOVERY TGA .
2. Evaluation of flammability
In order to evaluate the flame retardancy, it was measured according to KS-M ISO 4589-1 ~ 3 or JIS K7201 A-1. Generally, it can be judged that the flame retardancy is excellent when the LOI index (Limiting Oxygen Index) is 26 or more.
3. Properties of fibers
The properties of the fibers prepared as in Examples 7 to 12 and Comparative Examples 5 to 7 and 9 were evaluated as follows.
1 point: defective (circular, difficult to apply for fabric),
3 points: Good (level to apply circular, fabric)
5 points: Excellent (excellent for circular and fabric application)
4. Radiation workability
In order to evaluate the radiation availability, the radiation workability was determined as follows.
X: Not spinning,?: Five minutes inside,?: Ten minutes inside,?: Good
(weight%)
(weight%)
As can be seen from Tables 3 and 4, Examples 1 to 6 satisfied the remaining amount of inorganic materials of 15 to 20% by weight and were excellent in flame retardancy. Examples 7 to 12, which are flame retardant polyester fibers prepared from the compositions of Examples 1 to 6, are excellent in spinnability, satisfy the balance of inorganic matter of 15 to 20% by weight, have excellent flame retardancy, Was also excellent. Comparative Examples 2 to 4, in which the blending weight ratio of the phosphorus-containing flame retardant and the nitrogen-containing flame retardant, and the total flame retardant content exceeded the range of the present invention, showed that the residual amount of inorganic material did not satisfy the above range, And the comparative examples 5 to 7 prepared by using the same showed a radioactive decline and even if they were radiated, the residual amount of the inorganic material did not satisfy the above range, and the physical properties such as uniformity and productability of the fiber were lowered. Also, Comparative Example 8 in which the flame retardant was slurried during the polyester polymerization and did not slurry, and Comparative Example 8 in which the flame retardant was simply mixed did not satisfy the above range, and Comparative Example 9 in which the fiber was produced using the same also decreased radioactivity, Did not satisfy the above range, and the physical properties of the fibers were decreased.
Claims (12)
The phosphorus flame retardant may include at least one selected from the group consisting of phosphate, phosphonate, phosphinate, phosphine oxide, and phosphazene. By weight of a flame retardant polyester composition.
Wherein the nitrogen containing flame retardant comprises at least one selected from the group consisting of melamine, melamine cyanurate, triphenylisocyanurate, melamine phosphate, melamine pyrophosphate, ammonium polyphosphate, alkylamine phosphate and piperidine acid polyphosphate ≪ / RTI >
The polyester has an intrinsic viscosity (IV) of 0.6 to 0.8 dl / g.
The flame-retardant polyester composition may further comprise at least one selected from the group consisting of a silicone-based flame retardant, a lubricant, an antioxidant, a light stabilizer, a hydrolysis stabilizer, a releasing agent, a pigment, an antistatic agent, a conductivity imparting agent, an EMI shielding agent, Wherein the flame retardant polyester composition further comprises at least one additive selected from the group consisting of an inactivating agent, an opacifying agent, a fluorine-based antistatic agent, an anti-friction wear-resistant agent, and a coupling agent.
The method of producing a flame retardant are flame-retardant polyester composition, characterized in that the slurry to an average particle size of 0.03 to 0.8 μm and a flame retardant powder polyol mixture to 0.01 to 0.1 g / cm 3 .s viscosity of the screen to input.
Wherein the flame retardant comprises 5 to 20% by weight of the total composition, the flame retardant comprises a phosphorus-based flame retardant and a nitrogen-containing flame retardant, and the phosphorus-based flame retardant and the nitrogen-containing flame retardant are mixed in a weight ratio of 9: 1 to 6: By weight based on the total amount of the flame retardant polyester composition.
Wherein the flame retardant polyester composition has an amount of residual inorganic material of 15 to 20% by weight when heated up to 900 캜.
The phosphorus flame retardant may include at least one selected from the group consisting of phosphate, phosphonate, phosphinate, phosphine oxide, and phosphazene. By weight based on the total amount of the flame retardant polyester composition.
Wherein the nitrogen containing flame retardant comprises at least one selected from the group consisting of melamine, melamine cyanurate, triphenylisocyanurate, melamine phosphate, melamine pyrophosphate, ammonium polyphosphate, alkylamine phosphate and piperidine acid polyphosphate ≪ RTI ID = 0.0 > 1, < / RTI >
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102246650B1 (en) * | 2020-11-18 | 2021-04-29 | 박미자 | Method for manufacturing mineral fire retardant comprising multiple function water containing minerals and mineral fire retardant manufactured by the same |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102246650B1 (en) * | 2020-11-18 | 2021-04-29 | 박미자 | Method for manufacturing mineral fire retardant comprising multiple function water containing minerals and mineral fire retardant manufactured by the same |
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