KR20100126612A - Flame retardant material using monomer with phosphorous - Google Patents
Flame retardant material using monomer with phosphorous Download PDFInfo
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- KR20100126612A KR20100126612A KR1020090045230A KR20090045230A KR20100126612A KR 20100126612 A KR20100126612 A KR 20100126612A KR 1020090045230 A KR1020090045230 A KR 1020090045230A KR 20090045230 A KR20090045230 A KR 20090045230A KR 20100126612 A KR20100126612 A KR 20100126612A
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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
- C09K21/12—Organic materials containing phosphorus
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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
- C08K5/51—Phosphorus bound to oxygen
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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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
- C08L33/26—Homopolymers or copolymers of acrylamide or methacrylamide
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Abstract
Description
본 발명은 인 함유 모노머를 이용한 난연제에 관한 것으로, 보다 상세하게는 적어도 하나의 인 원자를 포함하는 불포화 모노머로 이루어진 난연 고분자에 아민류를 혼합하여 난연성을 더욱 향상시킨 인 함유 모노머를 이용한 난연제에 관한 것이다.The present invention relates to a flame retardant using a phosphorus-containing monomer, and more particularly to a flame retardant using a phosphorus-containing monomer further improved flame retardancy by mixing amines with a flame retardant polymer consisting of an unsaturated monomer containing at least one phosphorus atom. .
안전에 대한 요구가 증대됨에 따라 가연성을 갖는 대부분의 제품에 난연성을 갖출 것이 요구되고 있다. 가구 제조용 목재, 의복 제조용 섬유, 직물을 비롯하여 광범위한 영역의 제품들이 난연제를 코팅하거나 함침 하는 등의 방법으로 난연 가공되고 있다.As the demand for safety increases, it is required to be flame retardant in most combustible products. A wide range of products, including wood for furniture, textiles for fabrics, and fabrics, are flame retarded by coating or impregnating flame retardants.
그러나, 종래의 난연제의 경우 비용이 과도하거나 환경에 유해한 문제가 있었다. 예를 들어 난연성의 향상을 위해 또는 환전제로 각종 할로겐 소재들을 사용할 경우 환경 오염을 유발하게 된다.However, in the case of the conventional flame retardant there is a problem that the cost is excessive or environmentally harmful. For example, when various halogen materials are used to improve flame retardancy or as a currency exchange agent, environmental pollution is caused.
따라서, 종래의 난연제들에 비해 저렴한 비용으로 생산이 가능하며, 기존 난연제들이 갖는 유독성 문제를 해소할 수 있는 새로운 난연제에 대한 요구가 증대되고 있다.Therefore, the production of low-cost than conventional flame retardants is possible, and there is an increasing demand for a new flame retardant that can solve the toxicity problem of the existing flame retardants.
본 발명은 전술한 바와 같은 문제점을 해결하기 위한 것으로, 적어도 하나의 인 원자를 포함하는 불포화 모노머로 이루어진 난연 고분자에 아민류를 혼합하여 제조비용이 저렴하고 유독성이 없으면서도 난연성이 향상된 인 함유 모노머를 이용한 난연제를 제공하는 것에 목적이 있다. The present invention is to solve the problems as described above, by using a phosphorus-containing monomer with improved flame retardancy while low cost and no toxicity by mixing amines with a flame-retardant polymer consisting of an unsaturated monomer containing at least one phosphorus atom The purpose is to provide a flame retardant.
상기한 목적을 달성하기 위한 본 발명은, 적어도 하나의 인 원자를 포함하는 적어도 하나의 불포화 모노머를 고분자 중합하여 얻어진 폴리머 에멀션에 아민류를 혼합한 것을 특징으로 하는 인 함유 모노머를 이용한 난연제를 제공한다.The present invention for achieving the above object provides a flame retardant using a phosphorus-containing monomer, characterized in that amines are mixed with a polymer emulsion obtained by polymerizing at least one unsaturated monomer containing at least one phosphorus atom.
상기 적어도 하나의 인 원자를 포함하는 불포화 모노머는 포스포네이트(phosphonate) 또는 인산염 모노머를 포함하여 구성될 수 있다.The unsaturated monomer including the at least one phosphorus atom may include a phosphonate or phosphate monomer.
상기 불포화 모노머는 적어도 하나의 아크릴산염 또는 메타크릴산염 그룹을 포함할 수 있다. The unsaturated monomer may comprise at least one acrylate or methacrylate group.
바람직하게는, 상기 불포화 모노머는, 화학식Preferably, the unsaturated monomer is a chemical formula
((R=H 또는 CH3, m=1~4, n=1 또는 2)((R = H or CH3, m = 1-4, n = 1 or 2)
의 구조의 모노머로 이루어질 수 있다. It may be made of a monomer having a structure of.
특히 바람직하게는, 상기 모노머는Especially preferably, the monomer is
또는 화학식Or chemical formula
으로 구성될 수 있다. It may be configured as.
상기 폴리머 에멀션은 적어도 하나의 인 원자를 포함하는 적어도 하나의 불포화 모노머와 적어도 하나의 코모노머를 고분자중합하여 얻어질 수 있다. The polymer emulsion may be obtained by polymerizing at least one unsaturated monomer containing at least one phosphorus atom and at least one comonomer.
상기 폴리머 에멀션은 적어도 하나의 탄소 이중결합으로 구성된 적어도 하나의 불포화 코모노머를 포함하여 구성될 수 있다. The polymer emulsion may comprise at least one unsaturated comonomer composed of at least one carbon double bond.
바람직하게는, 상기 폴리머 에멀션은 상기 불포화 모노머가 적어도 0.0001중량% 이상 포함된다.Preferably, the polymer emulsion contains at least 0.0001% by weight or more of the unsaturated monomer.
또한, 상기 폴리머 에멀션은 코모노머와 불포화모노머가 75:25 내지 87.5:12.5의 중량비로 고분자중합된다. In addition, the polymer emulsion is polymerized in a weight ratio of comonomer and unsaturated monomer in a ratio of 75:25 to 87.5: 12.5.
상기 폴리머 에멀션은 2-(phosphonooxy)ethyl methacrylate 또는 2-(phosphonooxy)ethyl acrylate을 포함하며, 상기 아민류는 mono-, di-, tri-ethanol amine 인 것이 바람직하다. The polymer emulsion includes 2- (phosphonooxy) ethyl methacrylate or 2- (phosphonooxy) ethyl acrylate, and the amines are preferably mono-, di-, tri-ethanol amine.
상기한 바와 같은 본 발명에 의하면, 인 함유 불포화 모노머를 고분자 중합 하여 난연성을 갖는 폴리머 에멀션에 아민류를 첨가하여 난연성을 더욱 향상시킴으로써, 다양한 제품에 적용 가능한 친환경적이면서 비용이 저렴한 난연제를 제공할 수 있는 효과가 있다. According to the present invention as described above, by adding the amines to the polymer emulsion having a flame retardancy by polymerizing the phosphorus-containing unsaturated monomer to further improve the flame retardancy, it is possible to provide an eco-friendly and inexpensive flame retardant applicable to various products There is.
상술한 본 발명의 목적, 특징 및 장점은 다음의 상세한 설명을 통하여 보다 분명해질 것이다. 이하, 본 발명의 바람직한 실시예를 상세히 설명한다.The objects, features and advantages of the present invention described above will become more apparent from the following detailed description. Hereinafter, preferred embodiments of the present invention will be described in detail.
본 발명에 따른 난연제 조성물은 적어도 하나의 인 원자를 포함하는 적어도 하나의 불포화 모노머를 고분자 중합하고, 아민(Amine)류를 첨가하여 난연성을 향상시킨 수용성 고분자이다.The flame retardant composition according to the present invention is a water-soluble polymer that polymerizes at least one unsaturated monomer including at least one phosphorus atom and improves flame retardancy by adding amines.
바람직하게는, 상기한 적어도 하나의 인 원자를 포함하는 적어도 하나의 불포화 모노머는 포스포네이트(phosphonate) 또는 인산염(phosphate) 모노머를 포함하며, 인산염 모노머를 포함하는 것이 더욱 바람직하다.Preferably, the at least one unsaturated monomer comprising at least one phosphorus atom comprises a phosphonate or phosphate monomer, and more preferably comprises a phosphate monomer.
특히 바람직한 모노머는 적어도 하나의 acrylate 그룹을 포함하는 인산염 모너머들이다. acrylate 그룹 중에서도 acrylate 또는 methacrylate 그룹이 바람직하다. Particularly preferred monomers are phosphate monomers comprising at least one acrylate group. Among the acrylate groups, acrylate or methacrylate groups are preferable.
본 발명에서 특히 바람직한 모노머는 mono 및 bis[acryloyloxy(C1-4alkyl)] 인산염 모노머이다.Particularly preferred monomers in the present invention are mono and bis [acryloyloxy (C 1-4 alkyl)] phosphate monomers.
본 발명의 바람직한 실시예에서, 상기 난연제는 적어도 하나의 코모노머와 인 원자를 포함하는 적어도 하나의 불포화 모노머의 고분사중합에 의해 얻어진 폴 리머 에멀션을 포함한다.In a preferred embodiment of the invention, the flame retardant comprises a polymer emulsion obtained by high spray polymerization of at least one comonomer and at least one unsaturated monomer comprising a phosphorus atom.
바람직한 실시예에서, 상기 폴리머 에멀션은 코모노머와 인 원자의 비율이 99.9999:1 부터 0.0001:99.9999인 불포화 단위체의 고분자중합으로 얻어진다. 만족할만한 결과는 55:45 내지 96:4의 중량비에서 얻어지는데, 72:25 내지 87.5:12.5의 중량비가 가장 바람직하다.In a preferred embodiment, the polymer emulsion is obtained by polymer polymerization of unsaturated units in which the ratio of comonomer to phosphorus atom is 99.9999: 1 to 0.0001: 99.9999. Satisfactory results are obtained at a weight ratio of 55:45 to 96: 4, with a weight ratio of 72:25 to 87.5: 12.5 being most preferred.
상기 모노머는 적어도 하나 이상의 불포화 모노머를 포함하는 것이 바람직하며, 상기 폴리머 에멀션은 적어도 하나의 인 원자를 포함하는 두 개의 불포화 모노머를 포함하는 것이 가장 바람직하다. The monomer preferably comprises at least one unsaturated monomer, most preferably the polymer emulsion comprises two unsaturated monomers comprising at least one phosphorus atom.
상기 폴리머 에멀션은 2-(phosphonooxy)ethyl methacrylate 또는 2-(phosphonooxy)ethyl acrylate을 포함하며, 상기 아민류는 mono-, di-, tri-ethanol amine 인 것이 바람직하다.The polymer emulsion includes 2- (phosphonooxy) ethyl methacrylate or 2- (phosphonooxy) ethyl acrylate, and the amines are preferably mono-, di-, tri-ethanol amine.
상기 2-(phosphonooxy)ethyl methacrylate은 아래의 화학식을 갖는다.The 2- (phosphonooxy) ethyl methacrylate has the following formula.
상기 2-(phosphonooxy)ethyl acrylate은 아래의 화학식을 갖는다.2- (phosphonooxy) ethyl acrylate has the following formula.
[실험예][Experimental Example]
(실험1)Experiment 1
2리터 반응기에 교반기, 온도계, 콘덴서와 첨가제 포트를 준비하고 580ml의 증류수와 22.2g의 음이온 유화제(disodium alkyl sulphosucciante)를 준비한다. 반응 온도는 80℃로 질소가스 존재하에 1시간 정도 322RPM으로 교반하며 진행한다.Prepare a stirrer, thermometer, condenser and additive pot in a 2-liter reactor and 580 ml of distilled water and 22.2 g of anionic emulsifier (disodium alkyl sulphosucciante). The reaction temperature is 80 ℃ to proceed with stirring at 322 RPM for about 1 hour in the presence of nitrogen gas.
두 개의 개시 용액 ammonium persulphat (a)4.4%와 (b)1.02%를 증류수에 용해하여 준비한다.Two starting solutions ammonium persulphat (a) 4.4% and (b) 1.02% are prepared by dissolving in distilled water.
분리해서 2-(phosphonooxy)ethyl methacrylate (PM) 200gSeparated 2- (phosphonooxy) ethyl methacrylate (PM) 200g
methyl methacrylate 90g methyl methacrylate 90g
butyl acrylate 70g butyl acrylate 70g
methacrylic acid 5g methacrylic acid 5g
을 포함하는 균일한 모노머 혼합물(c)를 준비한다.Prepare a homogeneous monomer mixture (c) comprising a.
단위체 혼합물 (c) 15ml를 반응기에 투입하고 5분간 교반한 후, 4.4% 개시용액 (a) 3.4ml를 투입하여 5분간 교반한다.15 ml of the unit mixture (c) was added to the reactor and stirred for 5 minutes. Then, 3.4 ml of 4.4% starting solution (a) was added and stirred for 5 minutes.
남은 모노머 혼합물과 개시용액 (b)를 혼합하여 4.5시간 교반한다.The remaining monomer mixture and starting solution (b) are mixed and stirred for 4.5 hours.
이 시점에서 개시용액 (a) 3.4ml를 추가한다.At this point, 3.4 ml of starting solution (a) is added.
이 반응은 1시간 동안 지속된다.This reaction lasts for 1 hour.
반응 종결 후 생성된 물질은 상온에 방치하여 냉각한다.After completion of the reaction, the produced material is left to cool to room temperature.
생성된 물질을 80℃로 건조한다. 건조된 고분자 물질은 발화원에 노출될 때 자기소화의 성질을 갖는다.The resulting material is dried at 80 ° C. The dried polymeric material has the property of self-extinguishing when exposed to an ignition source.
이때의 한계산소지수는 25이다.At this time, the limit oxygen index is 25.
(실험2)Experiment 2
난연 고분자는 실험1에 의해 준비하고, 시약과 수량은 다음과 같다.The flame retardant polymer was prepared by Experiment 1, and the reagents and the quantity were as follows.
초기 충전 740ml의 증류수740ml of initial charge distilled water
22.2g의 음이온 유화제 22.2g anionic emulsifier
개시용액(a) 4.4% ammonium persulphateStarting solution (a) 4.4% ammonium persulphate
개시용액(b) 2% ammonium persulphateStarting solution (b) 2% ammonium persulphate
모노머 혼합물(c) 200g의 2(phosphonooxy)ethyl acrylate (PMH)Monomer mixture (c) 200 g of 2 (phosphonooxy) ethyl acrylate (PMH)
90g의 methyl methacrylate 90g methyl methacrylate
70g의 butyl acrylate 70g butyl acrylate
5g의 methacrylic acid 5 g of methacrylic acid
건조된 고분자는 불꽃에 노출되었을 때 자기 소화의 성질을 갖는다. The dried polymer has the property of self-extinguishing when exposed to a flame.
한계 산소지수는 26이다.The limit oxygen index is 26.
(실험3) 중화실험(Experiment 3) Neutralization Experiment
실험1에서 준비된 난연제와 mono ethanol amine의 중화 생성물Neutralizing products of flame retardants and mono ethanol amine prepared in Experiment 1
실험1 생성물질(PM) 100gExperiment 1 Product (PM) 100g
mono ethanol amine(MEA) 10gmono ethanol amine (MEA) 10g
실험1의 반응 종결 후 아민을 투입하여 반응 생성물을 중화하고 생성된 물질은 실내 온도로 냉각하여 방치한다. 이때의 한계산소지수는 29를 갖는다.After completion of the reaction in Experiment 1, amine was added to neutralize the reaction product, and the resulting material was cooled to room temperature and left to stand. At this time, the limit oxygen index is 29.
(실험4) 중화실험(Experiment 4) Neutralization Experiment
실험1에서 준비된 난연제와 di ethanol amine의 중화 생성물Neutralizing product of flame retardant and di ethanol amine prepared in Experiment 1
실험1 생성물질(PM) 100gExperiment 1 Product (PM) 100g
di ethanol amine(DEA) 17.2gdi ethanol amine (DEA) 17.2 g
실험1의 반응 종결 후 아민을 투입하여 반응 생성물을 중화하고 생성된 물질은 실내 온도로 냉각하여 방치한다. 이때의 한계산소지수는 28을 갖는다.After completion of the reaction in Experiment 1, amine was added to neutralize the reaction product, and the resulting material was cooled to room temperature and left to stand. The limit oxygen index at this time is 28.
(실험5) 중화실험(Experiment 5) Neutralization Experiment
실험1에서 준비된 난연제와 tri ethanol amine의 중화 생성물Neutralizing products of flame retardant and tri ethanol amine prepared in Experiment 1
실험1 생성물질(PM) 100gExperiment 1 Product (PM) 100g
tri ethanol amine(TEA) 24.4gtri ethanol amine (TEA) 24.4 g
실험1의 반응 종결 후 아민을 투입하여 반응 생성물을 중화하고 생성된 물질은 실내 온도로 냉각하여 방치한다. 이때의 한계산소지수는 26을 갖는다.After completion of the reaction in Experiment 1, amine was added to neutralize the reaction product, and the resulting material was cooled to room temperature and left to stand. The limit oxygen index at this time is 26.
(실험6) 중화실험(Experiment 6) Neutralization Experiment
실험2에서 준비된 난연제와 mono ethanol amine의 중화 생성물Neutralizing products of flame retardants and mono ethanol amine prepared in Experiment 2
실험2 생성물질(PMH) 100gExperiment 2 Product (PMH) 100g
mono ethanol amine(MEA) 10gmono ethanol amine (MEA) 10g
실험2의 반응 종결 후 아민을 투입하여 반응 생성물을 중화하고 생성된 물질은 실내 온도로 냉각하여 방치한다. 이때의 한계산소지수는 30을 갖는다.After completion of the reaction in Experiment 2, amine was added to neutralize the reaction product, and the resulting material was allowed to cool to room temperature. At this time, the limit oxygen index is 30.
(실험7) 중화실험(Experiment 7) Neutralization Experiment
실험2에서 준비된 난연제와 di ethanol amine의 중화 생성물Neutralizing product of flame retardant and di ethanol amine prepared in Experiment 2
실험2 생성물질(PMH) 100gExperiment 2 Product (PMH) 100g
di ethanol amine(DEA) 17.2gdi ethanol amine (DEA) 17.2 g
실험2의 반응 종결 후 아민을 투입하여 반응 생성물을 중화하고 생성된 물질은 실내 온도로 냉각하여 방치한다. 이때의 한계산소지수는 29를 갖는다.After completion of the reaction in Experiment 2, amine was added to neutralize the reaction product, and the resulting material was allowed to cool to room temperature. At this time, the limit oxygen index is 29.
(실험8) 중화실험(Experiment 8) Neutralization Experiment
실험2에서 준비된 난연제와 tri ethanol amine의 중화 생성물Neutralizing products of flame retardant and tri ethanol amine prepared in Experiment 2
실험2 생성물질(PMH) 100gExperiment 2 Product (PMH) 100g
tri ethanol amine(TEA) 24.4gtri ethanol amine (TEA) 24.4 g
실험2의 반응 종결 후 아민을 투입하여 반응 생성물을 중화하고 생성된 물질은 실내 온도로 냉각하여 방치한다. 이때의 한계산소지수는 27을 갖는다.After completion of the reaction in Experiment 2, amine was added to neutralize the reaction product, and the resulting material was allowed to cool to room temperature. At this time, the limit oxygen index is 27.
[표 1] 실험1 내지 실험8에 의해 생성된 물질의 LOI(산소한계지수) 측정치Table 1 Measurement of LOI (Oxygen Limit Index) of Substances Produced by Experiments 1-8
상기와 같이 아민의 첨가를 통해 더욱 향상된 난연성을 갖는 난연제를 얻을 수 있다. As described above, a flame retardant having further improved flame retardancy may be obtained through the addition of an amine.
이상에서 설명한 본 발명은 전술한 실시예 및 첨부된 도면에 의해 한정되는 것이 아니고, 본 발명의 기술적 사상을 벗어나지 않는 범위 내에서 여러 가지 치환, 변형 및 변경이 가능함은 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자에게 명백할 것이다.The present invention described above is not limited to the above-described embodiment and the accompanying drawings, and various substitutions, modifications, and changes are possible within the scope without departing from the technical spirit of the present invention. It will be evident to those who have knowledge of.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140296396A1 (en) * | 2011-10-31 | 2014-10-02 | Lubrizol Advanced Materials, Inc. | Non-halogen flame retardant polymers |
| US20150203692A1 (en) * | 2011-10-31 | 2015-07-23 | Lubrizol Advanced Materials, Inc. | Non-halogen flame retardant as coatings for fibrous filter media |
| KR20200037471A (en) | 2018-10-01 | 2020-04-09 | 한국세라믹기술원 | Composite fiber having flame retardancy and manufacturing method of the same |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140296396A1 (en) * | 2011-10-31 | 2014-10-02 | Lubrizol Advanced Materials, Inc. | Non-halogen flame retardant polymers |
| US20150203692A1 (en) * | 2011-10-31 | 2015-07-23 | Lubrizol Advanced Materials, Inc. | Non-halogen flame retardant as coatings for fibrous filter media |
| US9290639B2 (en) * | 2011-10-31 | 2016-03-22 | Lubrizol Advanced Materials, Inc. | Non-halogen flame retardant polymers |
| US9783687B2 (en) | 2011-10-31 | 2017-10-10 | Lubrizol Advanced Materials, Inc. | Non-halogen flame retardant as coatings for fibrous filter media |
| KR20200037471A (en) | 2018-10-01 | 2020-04-09 | 한국세라믹기술원 | Composite fiber having flame retardancy and manufacturing method of the same |
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