KR20140066049A - The phosphate ester for flame retadant and preparations thereof - Google Patents
The phosphate ester for flame retadant and preparations thereof Download PDFInfo
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Abstract
Description
본 발명은 인산 에스테르 난연제 및 그 제조방법에 관한 것으로, 더욱 상세하게는 디아미노테트라올과 포스페이트를 반응시켜 얻어지는 질소를 포함한 인산 에스테르 화합물 난연제에 관한 것이다.More particularly, the present invention relates to a phosphate ester compound flame retardant containing nitrogen obtained by reacting diaminotetraol with phosphate.
종래의 고분자용 난연제는 경제성 및 난연성이 뛰어난 할로겐계 난연제, 특히 브롬계 화합물이 난연증진제인 삼산화안티몬과 함께 대부분의 수지에 효과적으로 사용되어 왔으나 (일본특개소55-30739와 일본특개평8-302102), 브롬계 난연제는 화재 시 유독가스와 강력한 발암물질인 다이옥신(dioxine)을 생성시키는 것으로 알려져 사용이 점차 규제되고 있다. Conventional flame retardants for polymers have been effectively used for most resins in combination with halogen-based flame retardants having excellent economical efficiency and flame retardancy, particularly bromine compounds together with antimony trioxide, which is a flame retardant (JP-A-55-30739 and JP-A-8-302102) , Brominated flame retardants are known to generate toxic gases and dioxin, a potent carcinogen, in fire, and its use is increasingly regulated.
대부분의 고분자 수지는 연소하기 쉬운 성질을 가지고 있어 난연제를 첨가하거나 화학적으로 반응시켜 분자 내에 난연성 원소를 도입하여 난연화를 시키고 있다. 고분자 물질이 물성 향상을 위해 컴퓨터, TV, 전자기기의 부품을 비롯하여 자동차, 건축재료, 차량, 일반섬유의 난연 가공 등 거의 모든 분야에서 사용됨에 따라 화재 발생시 안전을 고려한 난연화에 대한 필요성이 증대되고 있다.Most polymer resins are easy to burn, adding flame retardants or chemically reacting them to introduce flame retardant elements into the molecules to make them flame retardant. In order to improve physical properties, polymer materials are used in almost all fields such as computer, TV, electronic parts, automobile, building material, automobile, general fiber, etc. Therefore, have.
할로겐계 난연제를 대체할 수 있는 난연제로 적극적으로 고려되고 있는 것이 포스페이트류, 포스포네이트류 또는 트라이페닐포스페이트(TPP) 등의 단분자형 유기 인계 화합물이 있으나, 이들은 내열성이 약하여 고분자 재료 성형시 휘발되기 쉽고, 수지로부터 난연제가 쉽게 용출되기 때문에 난연성 저하 및 2차 오염을 발생시킨다는 문제점이 있다. As a flame retardant that can replace halogen-based flame retardants, there are monomolecular organophosphorous compounds such as phosphates, phosphonates or triphenylphosphate (TPP) that are actively considered. However, since they have low heat resistance, And the flame retardant is easily eluted from the resin, so that the flame retardancy is lowered and the secondary contamination is generated.
이러한 문제점을 개선하기 위하여 , 레조시놀, 비스페놀 유도체 등을 이용한 축합형 인계 난연제가 사용 되고 있다. 하지만 상기 축합형 인계 난연제는 내열성, 내가수분해성 및 난연성의 측면에서 종래 할로겐계 난연제에 비해 효과가 현저하게 떨어지며, 스티렌계 수지 등에 사용하기가 어려운 점과 에스테르형 고분자 수지 (PET, PC등)에 첨가할 경우 에스테르 교환 반응으로 인하여 수지물성이 저하되는 문제점을 가지고 있다. In order to solve such problems, condensation type phosphorus flame retardants using resorcinol, bisphenol derivatives and the like have been used. However, in view of heat resistance, hydrolysis resistance and flame retardancy, the condensed phosphorus flame retardant is remarkably less effective than conventional halogen flame retardants, and is difficult to be used for styrene resins and the like, and that ester type polymer resins (PET, PC, etc.) There is a problem that the resin properties are deteriorated due to the transesterification reaction.
난연제의 안정성 및 난연성을 높이는 난연제로서 인-질소 공유결합을 갖게 하는 암모늄 폴리포스페이트, 멜라민 포스페이트 등이 있으나, 난연 성능이 낮아 부가적인 난연 첨가제를 필요로 한다는 문제점이 있다. 비할로겐 난연제의 종류로는 인계, 무기물 옥사이드나 하이드록사이드계, 질소 화합물계, 실리콘계 등이 있다. There are ammonium polyphosphate and melamine phosphate which have a phosphorus-nitrogen covalent bond as a flame retardant for enhancing the stability and flame retardancy of the flame retardant, but the flame retardant performance is low and an additional flame retardant additive is required. Examples of the non-halogen flame retardant include phosphorus, inorganic oxides, hydroxides, nitrogen compounds, and silicones.
일본특허공개공보 소55-30739 Japanese Patent Laid-Open Publication No. 55-30739
일본특허공개공보 평8-302102Japanese Patent Application Laid-Open No. 8-302102
그러나 질소 화합물계나 , 실리콘계도 단독으로는 난연성을 부여하기 어렵고, 아직까지 할로겐 난연제의 성능을 대체할만한 난연제의 개발이 이루어지지 않고 있어 각각의 장단점을 보안한 새로운 난연제의 개발이 필요하다. However, it is difficult to impart flame retardancy to the nitrogen-based or silicon-based flame retardant alone, and development of a flame retardant that can replace the performance of the halogen flame retardant has not yet been developed.
본 발명은 디아미노테트라올와 포스페이트를 반응시켜 얻은 질소를 포함한 하기 식의 인산 에스테르 화합물 난연제 및 이 화합물을 포함하는 난연 조성물에 관한 것이다. The present invention relates to a flame retardant of a phosphoric acid ester compound of the following formula containing nitrogen obtained by reacting a diaminotetraol with a phosphate, and a flame retardant composition comprising the compound.
상기 식에서 화합물은 R1은 에틸렌기, 또는 작용기 없는 것, R2는 페닐기, R3은 작용기가 없거나 메틸기이다.Wherein the compound is R 1 is not an ethylene group, or a functional group, R 2 is a phenyl group , and R 3 is a functional group or a methyl group.
디 아미노 테트라올의 합성 반응식은 아래와 같다.The synthesis formula of diaminotetraol is as follows.
본 발명에 따른 난연 제는 할로겐 원소를 포함하고 있지 않아 환경 친화적이며, 시너지 효과를 낼 수 있는 인과 질소를 동시에 포함하고 있으며 난연성이 뛰어나 우레탄 수지 등의 난연제로 사용될 수 있다.The flame retardant according to the present invention is environmentally friendly since it does not contain a halogen element, and contains phosphorus and nitrogen which can produce a synergistic effect, and is excellent in flame retardancy and can be used as a flame retardant such as urethane resin.
도 1은 본 발명에 의해 합성된 N,N,N',N'-테트라키스(2-히드록시-2-메틸에틸)디아민의 LC-MS이다.
도 2는 본 발명에 의해 합성된 N,N,N',N'-테트라키스(2-히드록시에틸)디아민의 H1-NMR
도 3은 본 발명에 의해 합성된 BAEPP-EO의 FAM-MS 이다.
도 4 내지 도 6은 본 발명에 의해 합성된 인산 에스테르의 H1-NMR 1 is an LC-MS of N, N, N ', N'-tetrakis (2-hydroxy-2-methylethyl) diamine synthesized by the present invention.
FIG. 2 is a graph showing the effect of H 1 -NMR (2-hydroxyethyl) diamine of N, N, N ', N'-tetrakis
Figure 3 is a FAM-MS of BAEPP-EO synthesized by the present invention.
Figs. 4 to 6 are graphs showing the H 1 -NMR of the phosphoric acid ester synthesized by the present invention
이하 , 본 발명을 상세히 설명하기로 한다. Hereinafter, the present invention will be described in detail.
본 발명은 하기 화학식으로 표시되는 다양한 디아미노테트라올과 인산화제를The present invention relates to various diaminotetraols and phosphating agents represented by the following formula
반응시켜 난연제로 사용가능한 인산 에스테르 난연제 제조에 관한 것이다.To produce a phosphoric acid ester flame retardant which can be used as a flame retardant.
더욱 상세하게는 디아미노테트라올과 포스페이트를 반응시켜 얻은 하기 화학식식으로 표시되는 인산에스테르 화합물 및 이를 포함하는 난연제의 제조에 관한 것이다. More particularly, the present invention relates to a phosphoric acid ester compound represented by the following formula obtained by reacting diaminotetraol with a phosphate, and a flame retardant containing the same.
상기 식에서 화합물은 R1은 에틸렌기, 또는 작용기 없는 것, R2는 페닐기, R3은 작용기가 없거나 메틸기이다.Wherein the compound is R 1 is not an ethylene group, or a functional group, R 2 is a phenyl group , and R 3 is a functional group or a methyl group.
난연제가 난연효과를 나타내는 통상적인 방식은 첫 번째로 고체상 저해 방법이 있는 데 이 방식은 난연제가 타르(char)를 형성하여 열이 내부로 전달되는 것을 막는다. 두 번째로는 기상 저해 방법이 있는데 이에 의하면 화학적 구조를 변화시키고 라디칼 연쇄반응을 중지시켜 연소를 방지하게 된다.The usual way in which a flame retardant exhibits a flame retardant effect is, first, a solid phase inhibition method, which prevents the flame retardant from forming a char and transferring heat internally. Secondly, there is a vapor inhibition method which changes the chemical structure and stops the radical chain reaction to prevent combustion.
인계 난연제는 주로 연소할 때 열분해에 의해 폴리메타 인산을 생성하고 이것이 보호 층을 형성하는 경우와 폴리메타 인산이 생성될 때의 탈수작용에 의해서 생성되는 탄소 피막이 산소를 차단하여 연소를 막는 방식으로 난연 효과를 나타내는 것으로 알려져 있다. 본 발명에 따른 인계 난연제 물질은 첨가형으로서 주로 열작용에 의해 난연 효과를 나타내는 화합물이라고 할 수 있다. The phosphorus flame retardant mainly produces polymetaphosphoric acid by pyrolysis when burned, and the carbon film formed by the dehydration action when the protective layer is formed and the polymetaphosphoric acid is generated blocks oxygen to prevent flame retardancy Effect. The phosphorus-based flame retardant substance according to the present invention can be said to be a compound which exhibits a flame retarding effect mainly by the addition of heat, mainly.
이하, 본 발명에 따른 난연성물질을 제조하는 방법을 상세히 설명하기로 한다. Hereinafter, a method for producing the flame-retardant material according to the present invention will be described in detail.
본 발명에서는 먼저, 신규 인-질소계 난연성 물질을 효과적으로 제조하기 위하여 히드라진과 프로필렌 옥시드 또는 에틸렌 옥시드를 반응시켜 디아미노테트라올을 제조하고 연속적으로 다음 반응을 수행하여 원하는 인-질소계 난연성 물질을 제조한다.In the present invention, first, in order to effectively produce a new phosphorus-nitrogen flame retardant, hydrazine is reacted with propylene oxide or ethylene oxide to produce diaminotetraol, and the following reaction is successively carried out to obtain a desired phosphorus-based flame retardant .
디 아미노 테트라올의 합성 반응식은 아래와 같다The synthesis formula of diaminotetraol is as follows
다음으로 디아미노테트라올과 포스페이트를 반응시켜 인산에스테르 화합물을 제조하는데, 포스패이트는 특히 페닐 포스포닉 디클로라이드(phenyl phosphonic dichloride)가 바람직하다.The diaminotetraol is then reacted with a phosphate to produce a phosphoric acid ester compound. The phosphatophile is preferably phenylphosphonic dichloride.
[실시예 및 제조예][Examples and Production Examples]
난연성을 가진 난연제를 제조하기 위해서는 두개 이상의 활성화기를 가진 원료가 필요하다. 주 활성화기로는 포스포네이트(phosphonate)와 히드록시기를 가진 원료를 선택한다.To produce flame retardant flame retardant, a raw material having two or more activators is required. As the main activator, a raw material having a phosphonate and a hydroxyl group is selected.
포스포네이트 중 페닐포스포닉클로라이드를 선택한 것은 반응성이 좋기 때문이다.
The choice of phenylphosphonic chloride in the phosphonate is due to its good reactivity.
실시예1Example 1 : N,N, : N, N, N'N ' ,, N'N ' -- 테트라키스(2-히드록시-2-메틸에틸)디아민Tetrakis (2-hydroxy-2-methylethyl) diamine 제조 Produce
교반기, 온도계를 부착한 250ml 반응기에 상온에서 히드라진 5.01g(0.1mol)와 메탄올 50ml를 넣고 10℃이하를 유지하며 한 시간 동안 프로필렌옥사이드(0.42mol)을 천천히 적가 시킨다. 적가가 끝난 후 약 35∼40℃에서 약 10시간 동안 반응 시킨다. 반응 완료후, 황산 마그네슘을 이용하여 물을 제거하고 용매로 쓰인 메탄올과 반응물질을 제거한다. LC-MS(도 1)와 TLC를 이용하여 구조를 확인하였고, 85%의 수율로 수득하였다. 액체 크로마토그래프에서 1.378분대의 하나의 peak이 관찰되므로 하나의 물질이 존재함을 알 수 있었고, Mass spectrum의 분석을 통하여 N,N,N',N'-테트라키스(2-히드록시-2-메틸에틸)디아민의 M+1 peak인 265.1를 확인 하였다.
In a 250 ml reactor equipped with a stirrer and a thermometer, 5.01 g (0.1 mol) of hydrazine and 50 ml of methanol are added at room temperature, and propylene oxide (0.42 mol) is slowly added dropwise for one hour while maintaining the temperature below 10 ° C. After the dropping, the reaction is carried out at about 35 to 40 DEG C for about 10 hours. After completion of the reaction, water is removed using magnesium sulfate, and the methanol and the reactant used as the solvent are removed. The structure was confirmed using LC-MS (Figure 1) and TLC and was obtained in 85% yield. In the liquid chromatograph, one peak of 1.378 minutes was observed, and it was found that one substance was present. By analyzing the mass spectrum The M + 1 peak of N, N, N ', N'-tetrakis (2-hydroxy-2-methylethyl) diamine was found to be 265.1.
실시예2Example 2 : N,N, : N, N, N'N ' ,, N'N ' -- 테트라키스(2-히드록시에틸)디아민Tetrakis (2-hydroxyethyl) diamine 제조 Produce
교반기, 온도계를 부착한 250ml 반응기에 상온에서 히드라진 5.01g(0.1mol)와 메탄올 50ml를 넣고 10℃이하를 유지 하며 한 시간 동안 에틸렌 옥사이드(0.42mol)을 천천히 적가 시킨다. 적가가 끝난 후 약 35∼40℃에서 약 10시간 동안 반응 시킨다. 반응 완료후, 황산 마그네슘을 이용하여 물을 제거하고 용매로 쓰인 메탄올과 반응물질을 제거한다. H1-NMR을 이용하여 구조를 확인하였고(도 2), 80%의 수율로 수득하였다. δ2.74(m, 8H, Ha), δ3.65(m. 8H, Hb)의 특정피크를 얻었다.
In a 250 ml reactor equipped with a stirrer and a thermometer, 5.01 g (0.1 mol) of hydrazine and 50 ml of methanol are added at room temperature, and ethylene oxide (0.42 mol) is slowly added dropwise for one hour while keeping the temperature below 10 ° C. After the dropping, the reaction is carried out at about 35 to 40 DEG C for about 10 hours. After completion of the reaction, water is removed using magnesium sulfate, and the methanol and the reactant used as the solvent are removed. The structure was confirmed using H 1 -NMR (FIG. 2) and was obtained in a yield of 80%. ? 2.74 (m, 8H, H a ) and? 3.65 (m. 8H, H b ).
실시예3Example 3 : : BAEPPBAEPP -- EOEO 제조Produce
교반기, 온도계, ice-bath를 부착한 500ml 반응기에 무수 염화 메틸렌 100ml와 N,N,N',N'-테트라키스 (2-히드록시에틸) 에틸렌 디아민 0.05mol 11.85g을 넣는다. ice-bath를 이용하여 온도를 0∼10℃를 유지하며 페닐 포스포닉 디클로라이드 0.1몰을 천천히 적가한다. 30분 교반 후 트리에틸아민 0.2mol 20.2g 을 천천히 적가한다. 적가 완료 후 반응온도를 25∼30℃까지 온도를 올린 후 6시간 동안 반응을 시킨다. 황산 마그네슘을 이용하여 물을 제거하고 건조시킨다. FAM-MS(도3)에서 BAEPP-EO의 M+! 피크인 481을 확인하였다. H1-NMR을 도 4에 나타내었다. 1H-NMR(CDCl3 , 300 MHz) 분석을 통하여 δ2.46(m, 4H, Ha), δ2.7(m. 8H, Hb), δ4.1(t, 8H, Hc), δ7.4∼7.8(m, 5H, Hd,He,Hf)의 특정피크를 얻었다.
100 ml of anhydrous methylene chloride and 11.85 g of 0.05 mol of N, N, N ', N'-tetrakis (2-hydroxyethyl) ethylenediamine are placed in a 500 ml reactor equipped with a stirrer, a thermometer and an ice bath. 0.1 mol of phenylphosphonic dichloride is slowly added dropwise while maintaining the temperature at 0 to 10 ° C using an ice-bath. After stirring for 30 minutes, 20.2 g of 0.2 mol of triethylamine is slowly added dropwise. After completion of the addition, the reaction temperature is raised to 25 to 30 ° C, and the reaction is allowed to proceed for 6 hours. Water is removed using magnesium sulfate and dried. In FAM-MS (Fig. 3), M < + > Peak 481 was identified. H 1 -NMR is shown in FIG. 1 H-NMR (CDCl 3, 300 MHz) through the analysis δ2.46 (m, 4H, H a ), δ2.7 (m. 8H, H b), δ4.1 (t, 8H, H c), A specific peak of? 7.4 to 7.8 (m, 5H, H d , H e , H f ) was obtained.
실시예4Example 4 : : BAPPBAPP -- POPO 제조 Produce
교반기, 온도계, ice-bath를 부착한 500ml 반응기에 무수 염화 메틸렌 100ml와 N,N,N',N'-테트라키스(2-히드록시-2-메틸에틸)디아민 0.05mol 25.42g을 넣는다. ice-bath를 이용하여 온도를 0∼10℃를 유지하며 페닐 포스포닉 디클로라이드 0.1mol을 천천히 적가한다. 30분 교반 후 트리에틸아민 0.2mol 20.2g 을 천천히 적가한다. 적가 완료 후 반응온도를 25∼30℃까지 온도를 올린 후 6시간 동안 반응을 시킨다. 황산 마그네슘을 이용하여 물을 제거하고 건조시킨다. H1-NMR을 도 5에 나타내었다. 1H-NMR(CDCl3, 300 MHz) 분석을 통하여 δ1.21(d, 12H, Ha), δ3.63(m. 4H, Hb), δ2.7∼3.0(m, 8H, Hc), δ7.4∼7.8(m, 5H, Hd,He,Hf)의 특정피크를 얻었다.
100 ml of anhydrous methylene chloride and 25.42 g of 0.05 mol of N, N, N ', N'-tetrakis (2-hydroxy-2-methylethyl) diamine are placed in a 500 ml reactor equipped with a stirrer, a thermometer and an ice- 0.1 mol of phenylphosphonic dichloride is slowly added dropwise while maintaining the temperature at 0 to 10 ° C using an ice-bath. After stirring for 30 minutes, 20.2 g of 0.2 mol of triethylamine is slowly added dropwise. After completion of the addition, the reaction temperature is raised to 25 to 30 ° C, and the reaction is allowed to proceed for 6 hours. Water is removed using magnesium sulfate and dried. H 1 -NMR is shown in FIG. 1 H-NMR (CDCl 3, 300 MHz) through the analysis δ1.21 (d, 12H, H a ), δ3.63 (m. 4H, H b), δ2.7~3.0 (m, 8H, H c ) to obtain the specific peak of δ7.4~7.8 (m, 5H, H d, H e, H f).
실시예5Example 5 : : BAPPBAPP -- EOEO 제조 Produce
교반기, 온도계, ice-bath를 부착한 500ml반응기에 무수 염화 메틸렌 100ml와 N,N,N',N'-테트라키스(2-히드록시에틸)디아민 0.05mol 22.62g을 넣는다. ice-bath를 이용하여 온도를 0∼10℃를 유지하며 페닐 포스포닉 디클로라이드 0.1mol을 천천히 적가한다. 30분 교반 후 트리에틸아민 0.2mol 20.2g 을 천천히 적가한다. 적가 완료 후 반응온도를 25∼30℃까지 온도를 올린 후 6시간 동안 반응을 시킨다. 황산 마그네슘을 이용하여 물을 제거하고 건조시킨다. H1-NMR을 도 6에 나타내었다. 1H-NMR(CDCl3 , 300 MHz) 분석을 통하여 δ2.92(m, 8H, Ha), δ4.15(m. 8H, Hb), δ7.4∼7.8(m, 8H, Hc ,Hd,He)의 특정피크를 얻었다.
100 ml of anhydrous methylene chloride and 22.62 g of 0.05 mol of N, N, N ', N'-tetrakis (2-hydroxyethyl) diamine are placed in a 500 ml reactor equipped with a stirrer, a thermometer and an ice- 0.1 mol of phenylphosphonic dichloride is slowly added dropwise while maintaining the temperature at 0 to 10 ° C using an ice-bath. After stirring for 30 minutes, 20.2 g of 0.2 mol of triethylamine is slowly added dropwise. After completion of the addition, the reaction temperature is raised to 25 to 30 ° C, and the reaction is allowed to proceed for 6 hours. Water is removed using magnesium sulfate and dried. H 1 -NMR is shown in FIG. 1 H-NMR (CDCl 3, 300 MHz) through the analysis δ2.92 (m, 8H, H a ), δ4.15 (m. 8H, H b), δ7.4~7.8 (m, 8H, H c , H d , H e ).
실시예Example 6 : 난연성 평가 6: Flammability evaluation
상기 수지 조성물의 난연성 평가를 위해, 상기실시예 및 비교 예에 따라 시편을 제조하고 , UL-94 V시험방법을 이용하여 난연성 평가를 실시하였다. In order to evaluate the flame retardancy of the resin composition, specimens were prepared in accordance with the above-mentioned Examples and Comparative Examples, and the flame retardancy was evaluated using the UL-94 V test method.
제조된 시편에 대한 난연성 평가 시 시험규격은 작은 불꽃(small flame - 50W)을 사용하는 IEC 60695-11-10에 의거하여 불꽃 크기는 20 mm로 조절하고 , 점화 시 버너는 시편의 바닥으로부터 10mm 떨어진 곳에 위치하도록 하였다. 시편을 장치하고 버너로 10초간 불을 붙인 후 버너를 제거하고, 시편에 붙은 불이 꺼지기까지의 시간 t1, 다시 10초간 불을 붙인 후 버너를 제거하고 시편에 붙은 불이 꺼지기까지의 시간 t2, 파이어 글로우 (fire glow)가 없어질 때까지의 시간 t3 등을 측정하였다. The test specimens used for the evaluation of the flame retardancy of the prepared specimens were adjusted to a flame size of 20 mm according to IEC 60695-11-10 using a small flame (50 W), and the burner was placed 10 mm away from the bottom of the specimen Respectively. After the specimen has been set and the burner is turned on for 10 seconds, the burner is removed. The time t1 until the flame on the specimen is turned off is t1, the flame is applied again for 10 seconds and the burner is removed. And the time t3 until the fire glow disappears.
표 1. 제조된 난연제의 난연성 시험 결과Table 1. Flame Retardancy Test Results of the Prepared Flame Retardants
[평가기준][Evaluation standard]
UL 94 V-0의 난연 등급은 시편이 t1 과 t2가 각각 10초 미만일 때, 5 개 시편의 t1 + t2가 50초 미만일 때, 각각의 t2 + t3가 30초 미만일 때이며,The flammability rating of UL 94 V-0 is for specimens with t1 and t2 less than 10 seconds each, t1 + t2 of less than 50 seconds for each of the five specimens, and less than 30 seconds for each t2 + t3,
UL 94 V-1은 t1과 t2가 각각 30초 미만일 때, 5 개 시편의 t1+t2가 250초 미만일 때, 각각의 t2 + t3가 60초 미만이면서, 불똥에 의한 솜발화가 일어나지 않는 경우이며,UL 94 V-1 is when t1 and t2 are less than 30 seconds each, t1 + t2 of less than 250 seconds of 5 specimens, each t2 + t3 is less than 60 seconds, ,
UL 94 V-2는 t1 과 t2가 각각 30초 미만일 때, 5 개 시편의 t1 + t2가 250 초 미만일 때, 각각의 t2 + t3가 60 초 미만이면서, 불똥에 의한 솜발화가 일어나는 경우이다.
UL 94 V-2 is a case where t1 and t2 are less than 30 seconds each, t1 + t2 of less than 250 seconds, and t2 + t3 is less than 60 seconds.
본 발명에 따른 난연 조성물은 할로겐 원소를 포함하고 있지 않아 환경 친화적이며, 내열성이 우수하고 인과 질소를 동시에 포함하고 있으며, 난연성이 뛰어나 각종 고분자 수지의 난연제로 사용될 수 있다.
The flame retardant composition according to the present invention does not contain a halogen element, is environment-friendly, has excellent heat resistance, contains both phosphorus and nitrogen, and is excellent in flame retardancy and can be used as a flame retardant for various polymer resins.
Claims (3)
상기 식에서 화합물은 R1은 에틸렌기, 또는 작용기 없는 것, R2는 페닐기, R3은 작용기가 없거나 메틸기이다.
Of the formula Flame retardant containing phosphoric acid ester compound
Wherein the compound is R 1 is not an ethylene group, or a functional group, R 2 is a phenyl group , and R 3 is a functional group or a methyl group.
A process for producing a phosphoric acid ester compound according to claim 1, which comprises reacting hydrazine with propylene oxide or ethylene oxide to prepare diaminotetraol, and reacting diaminotetraol with a phosphite.
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| KR102609940B1 (en) * | 2023-04-27 | 2023-12-06 | 송현엘앤씨 주식회사 | Paint compositions having function of axial light, fluorescence and flame retardant, and a manufacturing method thereof |
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| WO2012013565A1 (en) | 2010-07-29 | 2012-02-02 | Basf Se | Phosphinic acid hydrazide flame retardant compositions |
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| WO2023277207A1 (en) * | 2021-06-28 | 2023-01-05 | 씨에스아이엠 주식회사 | Method for preparing phosphate propargyl ester compound useful as flame retardant for lithium ion battery |
| KR102609940B1 (en) * | 2023-04-27 | 2023-12-06 | 송현엘앤씨 주식회사 | Paint compositions having function of axial light, fluorescence and flame retardant, and a manufacturing method thereof |
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