KR20160118753A - Manufacturing method of flame retardant compound, flame retardant compound made by the same, and flame retardant composition including the same - Google Patents
Manufacturing method of flame retardant compound, flame retardant compound made by the same, and flame retardant composition including the same Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
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- 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
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- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
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- 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
- C08K5/51—Phosphorus bound to oxygen
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- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08K5/5398—Phosphorus bound to sulfur
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Abstract
The present invention relates to a flame retardant-free flame retardant manufacturing method, a flame retardant resin composition containing the same, and a flame retardant resin composition containing the same. More particularly, And a flame retardant resin composition containing the flame retardant. The present invention also relates to a flame retardant resin composition comprising the same.
Description
The present invention relates to a flame retardant-free flame retardant manufacturing method, a flame retardant resin composition containing the same, and a flame retardant resin composition containing the same. More particularly, And a flame retardant resin composition containing the flame retardant. The present invention also relates to a flame retardant resin composition containing the flame retardant.
Flame retardants are additives for the prevention of fire in electronic and electrical products as well as fibers, building materials, automobiles and furniture. The flame retardant is added to the thermoplastic resin or the thermosetting resin in order to impart flame retardancy to the resin molded article. Currently, as flame retardants, inorganic compounds, organic phosphorus compounds, organic halogen compounds, halogen-containing organic phosphorus compounds and the like are being developed. Among the above-mentioned compounds, the organic halogen compound and the halogen-containing organic phosphorus compound are known to exert excellent flame retarding effect. In particular, halogen flame retardants are recognized as the most excellent and economical flame retardants in the electric and electronic fields.
However, the halogen-containing compound has the problem that hydrogen halide is generated by pyrolysis during resin molding to corrode the mold, causing deterioration of the resin itself, causing coloring, and deteriorating the working environment. In addition, there is also a problem that toxic gases such as hydrogen halide, which are harmful to human bodies, are generated in the case of fire or incineration.
In response to these problems, in recent years, legal regulations on environmental pollution by flame retardants have been gradually strengthened, and phosphorus flame retardants have emerged as substitute flame retardants, and companies have strengthened restrictions on the use of halogen flame retardants, In fact.
However, since the phosphorus flame retardant has a higher unit cost than the halogen flame retardant, it can not be easily used as an additive for a general-purpose resin. In addition, currently used phosphorus flame retardants are poor in hydrolysis resistance and alkali resistance. Alkali Elution During Polyurethane Artificial Leather Production Stages for Automobile Sheets Alkali resistance and hydrolysis resistance are required in the air, but in the case of conventional phosphorus flame retardants, the flame retardancy due to the elution of alkali (Alkali) deteriorates sharply A problem has occurred. Therefore, flame retardants that can be mixed with other flame retardants (halogens and other non-flammable flame retardants) have been marketed in the field to compensate for their weaknesses, but their effects are insufficient.
Therefore, when a phosphorus flame retardant is used in a polyurethane artificial leather manufacturing process applied to an automobile seat cover, a phosphorus flame retardant having poor hydrolysis resistance and alkali resistance in the step of reducing an alkali content after microfiber impregnation of an initial resin composition And the flame retardancy after the process is deteriorated rapidly.
Disclosure of Invention Technical Problem [8] Accordingly, the present invention has been made keeping in mind the above problems occurring in the prior art, and an object of the present invention is to provide a novel flame retardant preparation method and a flame retardant agent produced thereby.
The present invention also aims to provide a flame retardant resin composition comprising the novel flame retardant according to the present invention.
According to an aspect of the present invention,
A first step of preparing a urethane-introduced compound represented by the following formula (1);
A second step of reacting the urethane-introduced compound represented by the formula (1) with the non-supported compound represented by the following formula (2); And
A third step of adding a polymerization reaction end compound represented by the following formula 3 to react; A method for producing a flame retardant compound represented by the following formula (4).
[Chemical Formula 1]
(wherein n is an integer of 3 to 100, Y is O or S, R 1 and R 4 are each selected from the group consisting of an alkyl group or an aryl group, R 2 and R 3 are each a C 1-20 alkyl group, A hydrocarbon group having 1 to 18 carbon atoms)
(2)
(R 5 is any one selected from an alkyl group having 1 to 100 carbon atoms, a carbonate compound, an acrylic compound, an ether compound, an organosilicon compound, an organic fluorine compound, and a glycol compound, or a combination thereof)
(3)
(R < 6 > is a hydrocarbon compound having 1 to 100 carbon atoms)
[Chemical Formula 4]
(wherein n is an integer of 3 to 100, Y is O or S, R 1 and R 4 are each selected from the group consisting of an alkyl group or an aryl group, R 2 and R 3 are each a C 1-20 alkyl group, And R 5 and R 6 are each selected from the group consisting of an alkyl compound having 1 to 100 carbon atoms, a carbonate compound, an acrylic compound, an ether compound, an organosilicon compound, an organic fluorine compound, and a glycol compound Any one or a combination thereof)
In one embodiment, the first step can provide a method for producing a flame retardant compound, which comprises reacting a compound represented by the following formula (5) with a compound represented by the following formula (6).
[Chemical Formula 5]
(wherein n is an integer of 3 to 100, Y is O or S, R 1 is any one selected from the group consisting of an alkyl group or an aryl group, R 2 and R 3 are each a hydrocarbon group having 1 to 18 carbon atoms ≪ / RTI >
[Chemical Formula 6]
(R 4 is any one selected from the group consisting of substituents including an alkyl group or an aryl group)
In one embodiment, the compound represented by Formula 6 is selected from the group consisting of methylene diphenyl diisocyanate (MDI), hexamethylene diisocyanate (HDI), isophoronediisocyanate (IPDI), isophorone diisocyanate Wherein the flame retardant is at least one selected from the group consisting of toluene diisocyanate (TDI).
In one embodiment, in the second step, the compound represented by Formula 1 is added to the compound represented by Formula 1 at intervals of 5 minutes to 100 minutes at one time or a plurality of times at 30 ° C to 60 ° C, Based on the weight of the flame retardant. Preferably, the compound represented by the above formula (2) may be added once to several times at intervals of 5 minutes to 10 minutes.
In one embodiment, in the second step, the compound represented by Formula 1 is reacted with the compound represented by Formula 2, and after 10 minutes to 60 minutes, a polyurethane synthesis catalyst is added thereto, And the reaction is maintained.
In one embodiment, the catalyst is not particularly limited, but includes an organic metal salt selected from the group consisting of Ag, Sn, Al, Ba, and Ti. Specifically, the catalyst is an organometallic salt containing a metal selected from the group consisting of Ag, Sn, Al, Ba, and Ti, and may be Ag-based, Bi-mixed (Bi-V mixed) , DBTDL (Dibutyl tin dilaate), DOTDL (Dioctyltin dilaurate), Al system, Ba system, and Ti system catalyst, or a combination thereof.
In one embodiment, the addition ratio of the compound represented by the formula (2) to the compound represented by the formula (1) is not particularly limited, but the ratio of the compound represented by the formula The addition ratio of the compound represented by the formula (2) and the polymerization reaction termination compound represented by the formula (3) can be appropriately controlled so that all of the isocyanate is reacted. For example, in order to improve the hydrolysis resistance and alkali resistance, it is possible to control the addition amount of the non-expense introduction compound represented by the general formula (2) to a high level.
In one embodiment, the charge and discharge introduction compound represented by Formula 2 may be any one selected from PTMG (polytetramethylene ether glycol), polycarbonate polyol, polyether polyol, and acryl polyol, or a combination thereof. More preferably, one or more selected from fluorinated alkyl groups, acrylic groups, that is, polytetramethylene ether glycol (PTMG), polycarbonate polyol, polyether polyol, and acryl polyol are added to impart water repellency and oil repellency Flame retardant compound as a flame retardant.
In one embodiment, the compound represented by Formula 3 to be added for the termination of the polymerization reaction may be any one selected from PTMG (polytetramethylene ether glycol), polycarbonate polyol, polyether polyol, and acryl polyol, A method for producing a compound can be provided.
In one embodiment, the compound represented by the formula (2) is the same as the compound represented by the formula (3).
In order to achieve the above object, another aspect of the present invention provides a flame retardant compound produced by any one of the above-described production methods and represented by the following formula (4).
[Chemical Formula 4]
(wherein n is an integer of 3 to 100, Y is O or S, R 1 and R 4 are each selected from the group consisting of an alkyl group or an aryl group, R 2 and R 3 are each a C 1-20 alkyl group, And R 5 and R 6 are each selected from the group consisting of a hydrocarbon compound having 1 to 100 carbon atoms, a carbonate compound, an acrylic compound, an ether compound, an organosilicon compound, an organic fluorine compound, and a glycol compound Any one or a combination thereof)
In one embodiment, R 4 may provide a flame retardant compound that is diphenylmethane.
In one embodiment, the R 1 is benzene, R 2 and R 3 may provide a propane flame retardant compound.
According to another aspect of the present invention, there is provided a flame retardant resin composition comprising any one of the flame retardant compounds described above.
In one embodiment, the flame retardant resin composition may comprise a polyurethane.
The flame retardant prepared according to the present invention includes the cost part which is not eluted during the alkali treatment, so that the resin composition containing the flame retardant of the present invention has improved hydrolysis resistance and alkali resistance. In addition, the flame retardant of the present invention may contain a urethane bond to improve compatibility with a resin containing urethane.
It should be understood that the effects of the present invention are not limited to the above effects and include all effects that can be deduced from the detailed description of the present invention or the configuration of the invention described in the claims.
1 is a 1 H-NMR analysis result of the flame retardant prepared in Synthesis Example of the present invention.
2 is a FR-IR analysis result of the flame retardant prepared in the Synthesis Example of the present invention.
Hereinafter, embodiments of the present invention will be described in detail. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
< Example 1> Flame retardant synthesis
< Example 1-1> Flame retardant synthesis
12.5 ml of Disodium phenyl phosphate dihydrate, 2.13 ml of 3-Chloro-1-Propanol, 37.5 ml of ethanol and 0.1 N HCl were added to a 1000 ml single-necked flask and stirred at 250 rpm at 800 rpm for 32 hours .
The solids formed in the one-necked flask were filtered using a filter paper, and the filtered solution was filtered through a rotary vacuum evaporator at 40 ° C. to remove the ethanol. The removed solution was subjected to separate extraction using a 2000 ml separatory funnel with methylene chloride .
The extracted solution was removed with a rotary vacuum evaporator at 40 ° C for 30 minutes. Ethanol and methylene chloride were evaporated at 70 ° C for 60 minutes to produce a flame retardant containing divalent OH groups.
< Experimental Example 1> One H- NMR Measure
1 H-NMR of the flame retardant prepared in Example 1-1 was measured and shown in FIG. A 400
< Experimental Example 2> FT - IR Measure
The FT-IR of the flame retardant prepared in Example 1-1 was measured and shown in FIG. An FT / IR-600 model of Japan Spectroscopy Co., Ltd. was used, and the degree of decomposition was controlled to 4 cm -1 by the purification method using potassium bromide, and the number of times of integration was controlled to 16 times.
< Example 1-2> Urethane group Introduction Flame retardant synthesis
To introduce the urethane group, 400 g of the flame retardant prepared in Example 1-1 was weighed into a 1000 ml glass reaction vessel, and the temperature was raised to 40 캜. Then, 116 g of liquid MDI (methylene diphenyl diisocyanate) was added in 25 minutes of 25% The reaction was carried out in turn. At this time, the reaction temperature was controlled at 45 ° C to 55 ° C.
< Example 1-3> Cost outflow Introduction Flame retardant synthesis
When the reaction of Example 1-2 was completed, 360 g of PTMG (Polytetramethylene glycol) was added in four portions at intervals of 30 minutes while controlling the reaction temperature at 45 ° C to 50 ° C for 30 minutes.
PTMG was added for the fourth time as a compound for introducing non-spent fuel. After 30 minutes, 0.08 g of dibutyl tin dilaulate (DBTDL) containing tin was added to the catalyst. The reaction rate was maintained at 45 ° C to 55 ° C for 2 hours, The reaction was terminated by adding PTMG (Polytetramethylene glycol) as a compound for introduction into the run.
< Example 2> Cost outflow Introduction Flame retardant Resin composition containing
20 parts by mass of the unfrozen flame retardant prepared in Example 1-3 was mixed with 100 parts by mass of a polyurethane wet resin for microfiber impregnation (ISW-543W, JSC), 200 parts by mass of DMF, 2 parts by mass of Surfactant (Goldschmidt) , And 10 parts by mass of a colorant (Black Toner) to prepare a flame retardant-containing resin composition.
Microfiber nonwoven fabric having a polyester / Nylon ratio of 3/7 was immersed in the resin composition thus prepared and coagulated in a coagulation bath (30 ° C, 25% aqueous solution of DMF) for 30 minutes, dried in a drying oven at 110 ° C To prepare a resin composition specimen 1 containing an expansive flame retardant having an area of 102 x 356 mm and a thickness of 13 mm.
< Example 3> Cost outflow Introduction Flame retardant Resin composition containing
The resin composition specimen prepared in Example 3 was immersed in an aqueous 3% NaOH solution at 100 캜 for 30 minutes, subjected to alkali elution, and dried to prepare a resin composition specimen 2.
< Comparative Example 1> Cost outflow Non-introduction Flame retardant Containing resin composition Produce
20 parts by mass of the unfiltered flame retardant prepared in Example 1-1, 200 parts by mass of DMF and 2 parts by mass of a foam stabilizer (Goldschmidt) were added to 100 parts by mass of a polyurethane wet resin for microfiber impregnation (ISW-543W, , And 10 parts by mass of a colorant (Black Toner) were mixed to prepare a resin composition.
The microfine nonwoven fabric having a polyester / Nylon ratio of 3/7 was immersed in the resin composition and coagulated in a coagulation bath (30 ° C, 25% aqueous solution of DMF) for 30 minutes and then dried in a drying oven at 110 ° C, A resin composition specimen 3 containing the introduced flame retardant was prepared.
< Comparative Example 2> Cost outflow Non-introduction Flame retardant Containing resin composition Produce
The resin composition specimen 3 containing the non-expelled flame retardant prepared in Comparative Example 1 was immersed in a 3% NaOH aqueous solution at 100 ° C for 30 minutes, subjected to an alkali elution process, and then dried to prepare a specimen 4.
< Comparative Example 3> Flame retardant Not included Resin composition manufacturing
A resin composition was prepared in the same manner as in Example 3 except that no flame retardant was added, and a specimen 5 was prepared using the resin composition.
< Comparative Example 4> Flame retardant Not included Resin composition manufacturing
The resin composition sample 5 containing no flame retardant prepared in Comparative Example 3 was immersed in an aqueous 3% NaOH solution at 100 ° C for 30 minutes, subjected to an alkali elution process, and dried to prepare Sample 6.
< Experimental Example 3> Measurement of Flame Retardancy of Resin Composition
The flame retardancy of each of the specimens 1 to 6 prepared in Examples 1 and 2 and Comparative Examples 1 to 4 was measured by the following flame retardancy measurement test method.
First, one end and both sides of the specimens prepared in Examples 1 and 2 and Comparative Examples 1 to 4 were fixed to a U-shape holder, and a holder of a horizontally mounted specimen was placed in a cabinet .
The specimen is ignited for 15 seconds so that the 19 mm portion of the flame reaches one end of the specimen and the flame reaches the surface of the specimen and the flame reaches the end of the specimen, The time required to reach 38 mm was measured. If the flame could not reach the 38mm mark, the time until the flame was turned off was measured. When the combustion was not reached to 254 mm from the 38 mm mark, the combustion time and the combustion length to the position where the combustion stopped progress were measured.
Five test specimens of the resin compositions containing the flame retardant prepared in Examples 3 and 4 and Comparative Examples 1 to 4 were prepared and the flame retardancy was evaluated based on the test piece having the maximum combustion length. However, if the difference between the maximum value and the minimum value of the measured value exceeds 40% of the average value, or if the self-extinguishing property is present, the additional test is repeated with five test pieces. To evaluate flame retardancy.
The burning rate was calculated according to the following formula.
B = 60 x (D / T)
(B is the burning rate (mm / min), D is the combustion length (mm), and T is the time (seconds)
- Burning length in mm and combustion time in seconds.
- The average value is included if there is more than 5 self-extinguishing, nonflammable, and 5 measurements from the higher value are averaged.
Within
Ignition
(second)
time
(second)
Length
(Mm)
speed
(Mm /
min
)
- Nonflammable: Non-burning sample even if the flame reaches the specimen for 15 seconds.
- Self-extinguishing property: 38mm If not burned to the marking line or if it is extinguished within 60 seconds at 50mm or less
Self-extinguishing I: Digested within 1 second
Self-extinguishing II: No burning to 38 mm mark or digestion within 60 seconds
● Self-extinguishing III: Digestion within 60 seconds, but burning progresses beyond the 38mm mark
● Fail: if not applicable to self-extinguishing properties I to III
In Table 1, it was confirmed that the test piece of the resin composition containing the flame retardant according to the present invention did not deteriorate the flame retardancy even when the alkali leaching process was carried out. In other words, when the specimens 1 and 2, specimens 3 and 4, and specimens 5 and 6 were compared, the combustion length and the burning rate of specimen 2, specimen 4, and specimen 6, which were subjected to the alkaline elution process, Alkali) elution was not performed, it was confirmed that the burning length and burning rate of specimen 1, specimen 3, and specimen 5 were increased.
In addition, in Table 1, it was confirmed that the flame retardancy lowering property by the leaching process was improved when the non-costed flame retardant prepared in one embodiment of the present invention was used as compared with general phosphorus flame retardant. That is, while the burning length of the specimen 2, which is the resin composition containing the flame retardant combined with the expelled part of the present invention, is about two times longer than the burning length of the specimen 1 before the elution step, It was confirmed that the burning length of the test piece 4, which is a general phosphorus flame retardant prepared in the comparative example, is about five times longer than the burning length of the test piece 3 before the elution process.
Further, referring to Table 1, flame retardancy was improved regardless of the presence or absence of the elution step when the phosphorus-based flame retardant prepared in Example 1 of the present invention as compared with the general phosphorus flame retardant was used. That is, while the burning length of the specimen 1 of the resin composition containing the expelled flame retardant prepared in one embodiment of the present invention is 13 mm, the burning length of the specimen 3, which is the general phosphorus flame retardant produced in the comparative example of the present invention Was 22 mm longer than that.
It will be understood by those skilled in the art that the foregoing description of the present invention is for illustrative purposes only and that those of ordinary skill in the art can readily understand that various changes and modifications may be made without departing from the spirit or essential characteristics of the present invention. will be. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive. For example, each component described as a single entity may be distributed and implemented, and components described as being distributed may also be implemented in a combined form.
The scope of the present invention is defined by the appended claims, and all changes or modifications derived from the meaning and scope of the claims and their equivalents should be construed as being included within the scope of the present invention.
Claims (14)
A second step of reacting the urethane-introduced compound represented by the formula (1) with the non-supported compound represented by the following formula (2); And
A third step of adding a polymerization reaction end compound represented by the following formula 3 to react;
(4). ≪ / RTI >
[Chemical Formula 1]
(wherein n is an integer of 3 to 100, Y is O or S, R 1 and R 4 are each selected from the group consisting of an alkyl group or an aryl group, R 2 and R 3 are each a C 1-20 alkyl group, Lt; / RTI >< RTI ID = 0.0 >
(2)
(R 5 is any one selected from an alkyl compound having 1 to 100 carbon atoms, a carbonate compound, an acrylic compound, an ether compound, an organosilicon compound, an organic fluorine compound, and a glycol compound, or a combination thereof)
(3)
(R < 6 > is a hydrocarbon compound having 1 to 100 carbon atoms)
[Chemical Formula 4]
(wherein n is an integer of 3 to 100, Y is O or S, R 1 and R 4 are each selected from the group consisting of an alkyl group or an aryl group, R 2 and R 3 are each a C 1-20 alkyl group, And R 5 and R 6 are each selected from the group consisting of an alkyl compound having 1 to 100 carbon atoms, a carbonate compound, an acrylic compound, an ether compound, an organosilicon compound, an organic fluorine compound, and a glycol compound Any one or a combination thereof)
In the first step, a compound represented by the following formula (5) and a compound represented by the following formula (6) are reacted.
[Chemical Formula 5]
(wherein n is an integer of 3 to 100, Y is O or S, R 1 is any one selected from the group consisting of an alkyl group or an aryl group, R 2 and R 3 are each a hydrocarbon group having 1 to 18 carbon atoms ≪ / RTI >
[Chemical Formula 6]
(R 4 is any one selected from the group consisting of substituents including an alkyl group or an aryl group)
The compound represented by the formula 6 may be selected from the group consisting of methylene diphenyl diisocyanate (MDI), hexamethylene diisocyanate (HDI), isophoronediisocyanate (IPDI), and toluene diisocyanate (TDI). Toluene diisocyanate). ≪ / RTI >
In the second step, the compound represented by the formula (2) is reacted at 30 ° C to 60 ° C while being fed from one to several times at intervals of 5 minutes to 100 minutes.
In the second step, the compound represented by the formula (1) is reacted with the compound represented by the formula (2), and after 10 to 60 minutes, the catalyst is added to maintain the reaction at 30 to 60 ° C ≪ / RTI >
Wherein the catalyst comprises an organic metal salt selected from the group consisting of Ag, Sn, Al, Ba, and Ti.
Wherein the compound represented by Formula 2 is any one selected from PTMG (polytetramethylene ether glycol), polycarbonate polyol, polyehter polyol, and acryl polyol, or a combination thereof.
Wherein the compound represented by Formula 3 is any one selected from PTMG (polytetramethylene ether glycol), polycarbonate polyol, polyehter polyol, and acryl polyol, or a combination thereof.
Wherein the compound represented by the formula (2) is the same as the compound represented by the formula (3).
[Chemical Formula 4]
(wherein n is an integer of 3 to 100, Y is O or S, R 1 and R 4 are each selected from the group consisting of an alkyl group or an aryl group, R 2 and R 3 are each a C 1-20 alkyl group, And R 5 and R 6 are each selected from the group consisting of a hydrocarbon compound having 1 to 100 carbon atoms, a carbonate compound, an acrylic compound, an ether compound, an organosilicon compound, an organic fluorine compound, and a glycol compound Any one or a combination thereof)
Wherein the flame retardant resin composition comprises urethane.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134802A (en) * | 2017-06-27 | 2019-01-04 | 万华化学集团股份有限公司 | A kind of phosphor-containing halogen-free flame retardant thermoplastic polyurethane elastomer composition and its preparation method and application |
| US20210139783A1 (en) * | 2017-10-10 | 2021-05-13 | International Business Machines Corporation | Flame retardant levulinic acid-based compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE102007056532A1 (en) * | 2007-11-23 | 2009-05-28 | Clariant International Ltd. | Mixtures of phosphorus-containing compounds, a process for their preparation and their use as flame retardants |
| TWI394765B (en) * | 2008-12-12 | 2013-05-01 | Ind Tech Res Inst | Flame-retardant waterborne polyurethane dispersion |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134802A (en) * | 2017-06-27 | 2019-01-04 | 万华化学集团股份有限公司 | A kind of phosphor-containing halogen-free flame retardant thermoplastic polyurethane elastomer composition and its preparation method and application |
| CN109134802B (en) * | 2017-06-27 | 2023-09-19 | 万华化学集团股份有限公司 | Phosphorus-containing halogen-free flame-retardant thermoplastic polyurethane elastomer composition and preparation method and application thereof |
| US20210139783A1 (en) * | 2017-10-10 | 2021-05-13 | International Business Machines Corporation | Flame retardant levulinic acid-based compounds |
| US11884866B2 (en) * | 2017-10-10 | 2024-01-30 | International Business Machines Corporation | Flame retardant levulinic acid-based compounds |
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