KR20170049263A - Heat-decomposed compound and method for gasification using the same - Google Patents
Heat-decomposed compound and method for gasification using the same Download PDFInfo
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- KR20170049263A KR20170049263A KR1020150150438A KR20150150438A KR20170049263A KR 20170049263 A KR20170049263 A KR 20170049263A KR 1020150150438 A KR1020150150438 A KR 1020150150438A KR 20150150438 A KR20150150438 A KR 20150150438A KR 20170049263 A KR20170049263 A KR 20170049263A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
- C08J9/10—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing nitrogen, the blowing agent being a compound containing a nitrogen-to-nitrogen bond
- C08J9/104—Hydrazines; Hydrazides; Semicarbazides; Semicarbazones; Hydrazones; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
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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
- C08L101/00—Compositions of unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
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Abstract
Disclosed is a heat decomposition compound capable of foaming a resin by pyrolysis and generating nitrogen gas, and a gas generating method using the same. The heat decomposition compound is represented by the following formula.
R is a hydrocarbon group having 1 to 30 carbon atoms and may contain 1 to 5 heteroatoms, R 1 is a hydrogen atom (H), a carbon number 1 to 5 with or without 1 to 5 heteroatoms A hydrocarbon group, a carbonyl group, a sulfonyl group, an amine group or a combination thereof, and n is an integer of 1 or 2.
Description
The present invention relates to a heat decomposition compound and a gas generating method using the same, and more particularly, to a heat decomposition compound capable of foaming a resin by pyrolysis to generate nitrogen gas and a gas generating method using the same.
The blowing agent is a resin additive for blending with a resin to prepare a porous foam. Azodicarbonamide (ADCA) is used as a foaming agent for thermoplastic resins such as polyethylene, polypropylene, ethylene-vinyl acetate copolymer (EVA), polyvinyl chloride, styrene-butadiene rubber, acrylonitrile- , p, p'-oxybis (benzenesulfonyl hydrazide), dinitroso pentamethylene tetramine (DPT), p-toluenesulfonyl hydrazide various organic compound blowing agents such as ptoluenesulfonylhydrazide, benzenesulfonyl hydrazide and tetrazole are known (see Japanese Patent No. 3482416, Korean Patent No. 1285869, US Patent Publication No. 2001-0056131, Japanese Patent Laid-Open No. 2009-197219, etc.).
Among the above blowing agents, azodicarbonamide (ADCA) is a general-purpose product because nitrogen gas is rapidly generated by heating, decomposition products are incombustible, and toxicity is low. However, when a foam is produced using azodicarbonamide, the azodicarbonamide is not completely decomposed and yellowish remnants remain, and the whiteness of the foam is lowered. In addition, when azodicarbonamide is pyrolyzed, toxic gases such as formamide, ammonia, and carbon monoxide, which can cause reproductive toxicity, may be generated.
Accordingly, an object of the present invention is to provide a foaming agent capable of suppressing or reducing the generation of harmful gases such as formamide and ammonia, and a method for foaming a resin using the foaming agent. Another object of the present invention is to provide a heat decomposition compound which is eco-friendly, can avoid the regulation of harmful substances, has a good foaming performance, and a gas generating method using the same.
In order to achieve the above object, the present invention provides a foaming agent represented by the following general formula (1).
[Chemical Formula 1]
Wherein R is a hydrocarbon group having 1 to 30 carbon atoms and may include 1 to 5 hetero atoms, R 1 is a hydrogen atom (H), a carbon number having 1 to 5 hetero atoms A hydrocarbon group, a carbonyl group, a sulfonyl group, an amine group or a combination thereof, and n is an integer of 1 or 2
The heat decomposition compound according to the present invention suppresses or reduces the generation of harmful gases such as formamide and ammonia and is pyrolyzed to generate mainly nitrogen gas. Therefore, it is environmentally friendly and can avoid the regulation of harmful substances, .
BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is an electron micrograph showing the particle morphology of a foaming agent synthesized in an embodiment of the present invention. Fig.
2 and 3 are photographs showing the appearance and the foamed cross section of the foam obtained by foaming the polyvinyl chloride resin using the foaming agent according to one embodiment of the present invention.
4 is a photograph showing a foamed cross section of a foam obtained by foaming a polyvinyl chloride resin using a conventional blowing agent.
Hereinafter, the present invention will be described in detail.
The heat decomposition compound according to the present invention is represented by the following general formula (1).
In the above formula (1), R is a hydrocarbon group having 1 to 30 carbon atoms, and may optionally contain 1 to 5 hetero atoms, and R 1 is a hydrogen atom (H) A hydrocarbon group having 1 to 5 hetero atoms, and represents a carbonyl group, a sulfonyl group, an amine group or a combination thereof, and n is an integer of 1 or 2.
Specifically, R may be an alkyl group having 1 to 20 carbon atoms, an aryl group having 4 to 20 carbon atoms, or a combination thereof (i.e., an alkyl group and an aryl group bonded), may contain 1 to 5 hetero atoms , And the hetero atom is oxygen (O), nitrogen (N), or sulfur (S). R 1 is an iso branched or linear alkyl group having 1 to 20 carbon atoms (specifically 1 to 10 carbon atoms, more specifically 1 to 5 carbon atoms), 2 to 20 carbon atoms (specifically 2 to 10 carbon atoms) An alkynyl group having 2 to 20 carbon atoms (specifically 2 to 10 carbon atoms), an alkynyl group having 3 to 20 carbon atoms (specifically 5 to 10 carbon atoms), a cycloalkyl group having 5 to 30 carbon atoms (specifically 5 to 20 carbon atoms (More specifically, having 5 to 12 carbon atoms), a heterocyclic group having 3 to 20 carbon atoms (specifically 3 to 10 carbon atoms) containing 1 to 3 hetero atoms, an amine group (-NH 2 ) An alkylamine or arylamine group having 1 to 20 carbon atoms (specifically 1 to 10 carbon atoms), an amidine group (-C (-NH 2 ) = NH) and an amino group having 1 to 10 carbon atoms (specifically 1 to 5 carbon atoms) And the like.
More specifically, R may include an oxygen atom as an alkyl group having 1 to 10 carbon atoms (such as a methyl group or an ethyl group), an aryl group having 5 to 12 carbon atoms (such as a phenyl group), or a combination thereof Ether-bonded structures such as ether-bonded structures connected by a bond. R 1 is a carbonyl group (-COR 2 , for example, Formula 1n) to which a carbonyl group (-COR 2 ), a sulfonyl group (-SO 2 R 3 ), a sulfonyl group (-SO 2 R 3 ) group (-COR 2) is bonded a sulfonyl group (-SO 2 R 3) may be, where, R 2 is a hydrocarbon group, an amine group (-NH 2, C 1 -C 10 -NHR 3, -N (R 3 ) 2 ) or a hydrazide group (-NHNH 2 , -NHNH (R 3 ), etc.), and R 3 represents a hydrocarbon group having 1 to 10 carbon atoms.
Generally, when the foaming agent has an alkyl group at the terminal thereof, the longer the chain, the better the mixing with various resins. On the other hand, if the chain of the alkyl group is too long, the molecular weight is greatly increased and the molecular weight is increased, the amount of gas generated per g is reduced. The foaming agent according to the present invention has an excellent mixing property with various resins within the range described above, and can increase the amount of generated gas such as nitrogen, carbon monoxide, carbon dioxide and the like.
Examples of the compounds represented by the formula (1) include the compounds represented by the following formulas (2) to (4).
(2)
In Formula 2, R 4 is an alkyl group having 1 to 30 carbon atoms (specifically 1 to 10 carbon atoms), an aryl group having 4 to 30 carbon atoms (specifically, 6 to 20 carbon atoms), an amidine group (-C (-NH 2 ) NH), an amidine group having 1 to 10 carbon atoms (specifically 1 to 5 carbon atoms) and a carbonyl group (-COR 5 ), R 5 represents an alkyl group or an amine group having 1 to 10 carbon atoms , R and n are the same as in the above formula (1). The foaming agent represented by the above-mentioned formula (2) can be exemplified by the following formulas (1a), (1b), (1c), (1f) to (1i), and (1s) to (1w).
(3)
In the general formula (3), R 6 represents an alkyl group having 1 to 30 carbon atoms (specifically 1 to 10 carbon atoms), an aryl group having 4 to 30 carbon atoms (specifically, 6 to 20 carbon atoms) such as phenyl and alkylaryl groups, And R 3 and R 7 each represent a hydrocarbon group of 1 to 10 carbon atoms, and R and n are the same as defined in the above formula (1), and specifically, an amine group (-NH 2 , -NHR 3 , -N (R 7 ) 2 ) . Examples of the foaming agent represented by the above formula (3) include the following formulas (1d, 1e, 1j, 1k, 1q, 1r).
[Chemical Formula 4]
In Formula 4, R 8 and R 9 are each independently selected from the group consisting of hydrogen and a sulfonyl group (-SO 2 R 10 ), and R 10 is a hydrocarbon group having 1 to 10 carbon atoms (an alkyl group, an aryl group, Combinations thereof, and the like). The foaming agent represented by the above-mentioned formula (4) can be exemplified by the following formula (1), 1m to 1p and the like.
Specific examples of the blowing agent according to the present invention include compounds represented by the following formulas.
(Formula 1a),
(1b),
(Formula 1c),
(1d),
(1e),
(1f),
(Formula 1g), (1h),
(1i), (1j),
(Ik), (Formula l),
(1m), (1n),
(Io), (Formula 1p),
(Formula 1q),
(Formula 1r)
(Formula 1s) (Formula 1t) (Formula 1u) (1v) (Formula 1w)
Unlike ADCA, which is a general purpose blowing agent, by introducing at least one sulfonyl group at the terminal of a hydrazine structure based on nitrogen, the foaming agent of the present invention is capable of forming an amide group capable of generating noxious gases such as formamide and ammonia ), Minimizes the generation of harmful gases, and avoids the regulation of harmful substances at high risk. In addition, the foaming agent of the present invention has a high decomposition temperature and a large amount of decomposition gas to be generated. In addition, since the nitrogen gas generated at the time of foaming is uniformly distributed in the resin, the foaming magnification is large and the closed cell .
The foaming agent according to the present invention can be produced by various conventional organic synthesis methods. Specifically, as shown in the following examples, a sulfonyl group-containing compound (for example, 4,4-oxydibenzenesulfonyl chloride, Mesyl chloride, tosyl sulfonyl chloride, etc.) with a hydrazide group-containing compound (for example, carbazide, semicarbazide, 4,4-oxydibenzenesulfonylhydrazide, etc.). Therefore, since the foaming agent of the present invention can be synthesized by a simple process in one step, it is easy to synthesize and can be produced economically.
The method for foaming a resin according to the present invention includes a step of mixing and heating the foaming agent of the present invention with a resin to be foamed. The foaming agent may be mixed with the resin to be foamed by a conventional resin mixing means such as a stirrer or a press roll. The heating may be carried out using a conventional resin such as an extruder, a press mold or a hot air circulating oven Heating means can be used. The operation conditions of the resin mixing means and the resin heating means can be appropriately operated according to the kind of the resin to be foamed, the type of the foaming agent, the kind of the additive, and the state. Typical operating conditions include the use of the foaming agent in the form of powder And master batch (master batch means that the foaming agent is concentrated and dispersed in the resin at a high concentration, for example, 10 to 55% by weight) The masterbatch may be prepared by mixing in a resin mixing means having a temperature of 90 to 120 캜 for 10 to 30 minutes and heating in a resin heating means having a temperature of 90 to 250 캜. The foamable resin and the foaming agent (in the form of a powder or a master batch) are mixed in a resin mixing means having a temperature of 25 to 120 DEG C for 1 to 30 minutes and heated at 150 to 250 DEG C (specifically, 170 to 230 DEG C ) And a resin heating means having a pressure of 100 to 160 kg / cm 2 (specifically, 100 to 150 kg / cm 2 ) for 20 seconds to 30 minutes. The amount of the blowing agent to be used may vary depending on the type of the resin to be foamed, the type of the blowing agent, the desired degree of foaming, etc. For example, the powdered blowing agent may be used in an amount of 1 to 40 parts by
Examples of the resin to be foamed in which the foaming agent of the present invention is used include polyethylene, polypropylene (PP), polyvinyl chloride (PVC), polycarbonate (PC), polystyrene (PS), polyamide, acetal, styrene butadiene rubber (SBR), an ethylene vinyl acetate copolymer (EVA), an ethylene propylene rubber (EPDM), a thermoplastic elastomer (TPE), a thermoplastic polyurethane (TPU), a thermoplastic rubber Various synthetic or natural resins such as thermoplastic rubber (TPR), ABS resin (acrylonitrile butadiene styrene copolymer), rubber, epoxy resin and acrylic resin may be used. In the foaming step, various additives such as calcium carbonate, zinc oxide, stearic acid, and dicyclohexyl phthalate may be used.
The blowing agent according to the present invention can be applied to engineering plastics such as vehicle seat, tire and roof tec cover, garnish cover device, weather strip, air duct for air conditioner, automobile products such as interior / , Footwear products such as wallpaper, flooring, artificial leather, sneakers and slippers, infant and children's mats, household appliances such as TVs, PCs (personal computers), foam molding products such as sashes, sponges, , Children's products such as toys, synthetic wood, accessory ornaments, and other plastic containers.
Hereinafter, the present invention will be described in more detail by way of examples. The following examples are provided to illustrate the present invention, and the scope of the present invention is not limited by these examples.
[Example 1] Production of blowing agent represented by the formula (1c)
As it is shown in following
[Reaction Scheme 1]
[Example 2] Production of foaming agent represented by the formula (1d)
As shown in Reaction Scheme 2, 100.0 g (0.28 mol, 4,4-oxydibenzenesulfonyl hydrazide) of 4,4-oxydibenzenesulfonyl hydrazide and 95.9 g (0.084 mol, mesyl chloride) of mesyl chloride were placed in a flask, , 100 mL of methylene chloride (MC) was added and stirred. 66.23 g (0.084 mol, pyridine) of pyridine was slowly added at room temperature and stirred for 2 hours. Next, 300 mL of ethanol (EtOH) and water were mixed at a ratio of 2: 1 at 0 ° C, stirred for 30 minutes, and washed with ethanol to synthesize a compound represented by formula (1d).
[Reaction Scheme 2]
[Example 3] Production of foaming agent represented by formula
45.0 g (0.5 mol, Cabazide) of carbazide and 84.0 g (1.0 mol) of NaHCO 3 were placed in a flask, and 225 mL of methanol (MeOH) was added as a solvent and stirred. 114.5 g (1.0 mol, mesyl chloride) of mesyl chloride was slowly added dropwise at room temperature, and then the temperature was raised to 65 캜. After the reaction was carried out for 2 hours, the temperature was lowered to room temperature and washed with methanol (MeOH) to synthesize a compound represented by formula (11).
[Reaction Scheme 3]
[Example 4] Production of blowing agent represented by the formula (1m)
50.0 g (0.55 mol, Cabazide) of carbazide and 46.6 g (0.55 mol) of NaHCO 3 were placed in a flask and 225 mL of methanol (MeOH) was added as a solvent and stirred. 63.5 g (0.55 mol, mesyl chloride) of mesyl chloride was slowly added dropwise at room temperature, and then the temperature was raised to 65 ° C. After the reaction was carried out for 2 hours, the temperature was lowered to room temperature and washed with methanol (MeOH) to synthesize a compound represented by formula (1m).
[Reaction Scheme 4]
[Example 5] Production of blowing agent represented by the formula (1p)
45.0 g (0.5 mol, Cabazide), 190.5 g (1.0 mol, tosyl sulfonyl chloride) and 84.0 g (1.0 mol) of NaHCO 3 were placed in a flask, and ethanol (EtOH) was added and stirred. After the reaction was carried out at 65 ° C for 3 hours, the temperature was lowered to room temperature and washed with ethanol (EtOH) to synthesize a compound represented by formula (1p).
[Reaction Scheme 5]
[Example 6] Production of blowing agent represented by the formula 1r
40.0 g (0.112 mol) of 4,4-oxydibenzenesulfonyl hydrazide and 64.0 g (0.335 mol, tosyl sulfonyl chloride) of tosyl sulfonyl chloride were placed in a flask, and methylene chloride MC) was added and stirred. 26.5 g (0.335 mol) of pyridine was slowly added at room temperature, and the mixture was stirred for 2 hours. Next, 300 mL of ethanol (EtOH) and water were mixed at a ratio of 2: 1 at 0 ° C, stirred for 30 minutes, and washed with ethanol to synthesize a compound represented by formula (1r).
[Reaction Scheme 6]
[Example 7] Production of blowing agent represented by the formula 1q
50.0 g (0.27 mol, tosyl sulfonyl hydrazide) of tosyl sulfonyl hydrazide and 76.8 g (0.40 mol) of tosyl sulfonyl chloride were placed in a flask and 250 mL of methylene chloride (MC) was added as a solvent And stirred. 31.9 g (0.4 mol) of pyridine was slowly added at room temperature, and the mixture was stirred for 2 hours. Next, 300 mL of ethanol (EtOH) and water were mixed at a ratio of 2: 1 at 0 ° C, stirred for 30 minutes, and then washed with ethanol to synthesize a compound represented by formula (1q).
[Reaction Scheme 7]
[Experimental Example 1] Measurement of decomposition temperature and gas volume of the foaming agent
The decomposition temperature (DT) and the gas volume (GV) were measured while 500 mg of each of the foaming agent synthesized in Examples 1 to 7 and the comparative example was heated and decomposed, The results are shown in Table 1 below. 1 shows an electron micrograph showing the particle shape of the foaming agent (formula (1c) synthesized in Example 1). The foaming agent synthesized in Example 1 and polyvinyl chloride (PVC) 100 and 3.5 phr of the foaming agent and ADCA prepared in Examples 1 to 7 were mixed and mixed well for 1 to 2 minutes using an agitator. Then, an oven set at a temperature of 210 to 230 ° C and then foamed in an oven for 1 minute, 14 seconds to 2 minutes and 30 seconds to prepare a polyvinyl chloride foam. An external view of the polyvinyl chloride foam produced and an enlarged photograph of a close cell 2 and 3, respectively. For comparison, a polyvinyl chloride resin was foamed under the same conditions using conventional azodicarbonamide (ADCA), and an enlarged photograph of the foamed cross section of the foamed polyvinyl chloride resin is shown in FIG.
As shown in Table 1 and Figs. 1 to 4, the foaming agent according to the present invention has a similar or superior decomposition temperature and gas volume as the azodicarbonamide (ADCA) used in general use, and has uniform pores Can form a foam, and thus can be usefully used as a foaming agent.
[Experimental Example 2] Foaming performance of foaming agent and measurement of formamide concentration occurring upon foaming
3.5 phr of the blowing agent prepared in Examples 1, 3 and 4 and the ADCA as Comparative Example were added to 100 gr of polyvinyl chloride (PVC) as a resin to be foamed, and the mixture was stirred for 1 to 2 minutes (min ), Followed by foaming in an oven set at a temperature of 210 to 230 ° C for 1 minute and 14 seconds to 2 minutes and 30 seconds to prepare a polyvinyl chloride foam, The foaming magnification of the polyvinyl chloride foam and the concentration of the formed formamide were measured, and the results are shown in Table 2 below. Here, N.D. (not detected) means that the concentration of formamide has occurred in such a small amount that it can not be measured or has not been issued.
(Formula 1c)
(Formula Il)
(1m)
As shown in Table 2, the foaming agent according to the present invention has an advantage that less amount of formamide, which is a harmful substance, is generated or is not generated, as compared with azodicarbonamide.
Claims (13)
[Chemical Formula 1]
Wherein R is a hydrocarbon group having 1 to 30 carbon atoms and may include 1 to 5 hetero atoms, R 1 is a hydrogen atom (H), a carbon number having 1 to 5 hetero atoms A hydrocarbon group, a carbonyl group, a sulfonyl group, an amine group or a combination thereof, and n is an integer of 1 or 2.
(2)
R 4 is an alkyl group having 1 to 30 carbon atoms, an aryl group having 4 to 30 carbon atoms, an amidine group (-C (-NH 2 ) ═NH), an amidine group having 1 to 10 carbon atoms and a carbonyl group (-COR 5) it is selected from the group consisting of, wherein R 5 represents an alkyl group or an amine group of a carbon number of 1 to 10, R and n have the same meaning in the general formula (1).
(3)
In Formula 3, R 6 is selected from the group consisting of an alkyl group having 1 to 30 carbon atoms, an aryl group having 4 to 30 carbon atoms, and an amine group, and R and n are the same as in Formula 1.
[Chemical Formula 4]
In Formula 4, R8 and R9 are each independently selected from the group consisting of hydrogen and a sulfonyl group (-SO 2 R 10), wherein R 10 represents a hydrocarbon group having 1 to 10 carbon atoms.
A foaming agent represented by the following general formula (1)
Wherein the content of the foaming agent relative to 100 parts by weight of the resin is 1 to 40 parts by weight of a blowing agent in the form of a powder or 10 to 80 parts by weight of a blowing agent in a master batch form.
[Chemical Formula 1]
Wherein R is a hydrocarbon group having 1 to 30 carbon atoms and may include 1 to 5 hetero atoms, R 1 is a hydrogen atom (H), a carbon number having 1 to 5 hetero atoms A hydrocarbon group, a carbonyl group, a sulfonyl group, an amine group or a combination thereof, and n is an integer of 1 or 2.
[Chemical Formula 1]
Wherein R is a hydrocarbon group having 1 to 30 carbon atoms and may include 1 to 5 hetero atoms, R 1 is a hydrogen atom (H), a carbon number having 1 to 5 hetero atoms A hydrocarbon group, a carbonyl group, a sulfonyl group, an amine group or a combination thereof, and n is an integer of 1 or 2.
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