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WO2015102373A1 - Mousse polyuréthanne rigide à base de résine phénolique obtenue sans agent durcisseur acide et son procédé de production - Google Patents

Mousse polyuréthanne rigide à base de résine phénolique obtenue sans agent durcisseur acide et son procédé de production Download PDF

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Publication number
WO2015102373A1
WO2015102373A1 PCT/KR2014/013043 KR2014013043W WO2015102373A1 WO 2015102373 A1 WO2015102373 A1 WO 2015102373A1 KR 2014013043 W KR2014013043 W KR 2014013043W WO 2015102373 A1 WO2015102373 A1 WO 2015102373A1
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WO
WIPO (PCT)
Prior art keywords
polyurethane foam
phenolic resin
rigid polyurethane
prepolymer
acid curing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2014/013043
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English (en)
Korean (ko)
Inventor
조좌룡
임지형
김보라
김상범
이주찬
서중석
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Korea Atomic Energy Research Institute KAERI
Industry Academic Cooperation Foundation of Kyonggi University
Original Assignee
Korea Atomic Energy Research Institute KAERI
Industry Academic Cooperation Foundation of Kyonggi University
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Application filed by Korea Atomic Energy Research Institute KAERI, Industry Academic Cooperation Foundation of Kyonggi University filed Critical Korea Atomic Energy Research Institute KAERI
Publication of WO2015102373A1 publication Critical patent/WO2015102373A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/54—Polycondensates of aldehydes
    • C08G18/542—Polycondensates of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0025—Foam properties rigid

Definitions

  • the present invention is that the conventional phenolic foam is thermally stable at high temperature, but the strength is weak and easily broken and poor insulation, and the conventional rigid polyurethane foam has a problem of being rapidly decomposed at 200 °C or more, although excellent thermal insulation and strength
  • phenolic resin-based polyurethane foams can be synthesized to compensate for the shortcomings of the two materials and, unlike previous published studies, foaming without the use of acid hardeners does not cause corrosion of metals. It relates to a rigid polyurethane foam based and a method for producing the same.
  • Polymer materials which are widely used in daily life, take up a large portion of metal materials and inorganic materials such as aircraft, vehicles, trains, building structures and interior materials, and everyday products based on the advantages of excellent processability, light weight, and economic efficiency.
  • metal materials and inorganic materials such as aircraft, vehicles, trains, building structures and interior materials, and everyday products based on the advantages of excellent processability, light weight, and economic efficiency.
  • due to the nature of the polymer material it is weak to low heat and flame, and has a disadvantage of generating a large amount of toxic gas and smoke when reacting.
  • the smoke generated has the disadvantage of losing the visibility and direction of the person, lengthening the exposure time to the toxic gas and consequently losing the evacuation capacity.
  • Insulation materials using halogen or phosphorus flame retardant materials are used in polymer materials.
  • thermal stability is limited because the resin itself is weak and plastic, and the production cost is high when flame retardants are added. The situation is avoiding the use of flame retardant materials.
  • phosphorus compounds are often water-soluble, they are eluted at the time of disposal, causing environmental pollution.
  • Phenolic resins are multifunctional, having a large number of reactive bonds, and are easily carbonized as a whole of the molding material and form a film to block the flame. Therefore, the phenol resin itself has extremely high heat resistance and flame resistance even without adding a flame retardant having a large environmental load. .
  • phenol resin phenol resin
  • phenol resin does not generate harmful gases such as halogen compounds during combustion and excellent thermal safety has been concentrated around the world research on the insulation material using phenol resin.
  • the present inventors studied to solve the thermal stability problem of the polyurethane foam foamed by using the polyether and ester-based resins used in the prior art, and the resin itself reacts with isocyanate to expand the phenol resin having a thermally stable resonance structure with isocyanate.
  • Isocyanate prepolymer was used to confirm the presence / absence and to establish the foaming conditions, and the present invention was completed by checking the physical properties.
  • the present invention has the advantage that the phenolic foam used in the past is stable at high temperature, the mechanical strength is weak and easily broken and poor insulation, acid curing agent corrodes the metal to shorten the life of the equipment and,
  • foaming a polyurethane foam using a phenol resin having a resonance structure ensures high thermal stability, and Not only solves the problems of the prior art by complementing the mechanical strength, which is a disadvantage of the conventional phenolic foams by the secondary bonding and crosslinking between functional groups, but also does not use acid curing agents unlike the phenolic resin-based polyurethane foams studied in the past. It is an object of the present invention to provide a rigid polyurethane foam and a method of manufacturing the same that can solve the problem of corrosion of the metal by the curing agent.
  • the present invention is a phenol resin
  • Isocyanate prepolymer to provide a rigid polyurethane foam based phenol resin foamed without using an acid curing agent, prepared by mixing foamed.
  • 100 parts by weight to 150 parts by weight of the isocyanate prepolymer is added to 100 parts by weight of the phenol resin and stirred at 2500 to 3500 rpm to provide a method for producing a rigid polyurethane foam comprising the step of synthesizing the rigid polyurethane foam.
  • the phenolic resin-based rigid polyurethane foam according to the present invention can solve the problem of corrosion of the prior art by not using an acid curing agent in the phenolic foam, and the phenolic resin having improved thermal stability at high temperature than the conventional polyurethane foam. It has the advantage of being able to provide a base polyurethane foam.
  • 1 is a photograph showing the form of the foam after combustion.
  • thermogravimetric analysis graph of phenolic resin foam according to NCO% of prepolymer is a thermogravimetric analysis graph of phenolic resin foam according to NCO% of prepolymer.
  • Figure 3 is a graph comparing the foam synthesized with a urethane foam synthesized using a polyester polyol and a phenol resin.
  • Conventional rigid polyurethane foam is a material having excellent thermal insulation, chemical resistance and high compressive strength, but there is a problem that it is rapidly decomposed above 200 °C, conventional phenolic foam has a high heat resistance, but the strength is weak and easily broken and hardened when hardened There is a drawback of corroding the product by adding a topic. In order to solve this problem, studies have been made to add isocyanate to a conventional phenolic foam in which a phenol resin and an acid hardener are mixed.
  • the present invention relates to a phenolic resin-based hard polyurethane foam without using an acid hardener
  • the hard polyurethane foam is phenolic resin
  • Isocyanate prepolymer prepared by mixing and foaming.
  • the phenol resin is characterized in that the resol (phenol) type phenol resin.
  • Phenolic resins are thermosetting resins formed by reacting phenols and formaldehydes, which are of Novolac type and Resol type.
  • the novolak type is obtained by reacting under an acidic catalyst. At room temperature, it melts when heated to a solid phase but does not cure. It hardens when a crosslinking agent is added and heated.
  • the resol type is obtained by reacting under an alkaline catalyst and cures when heated. Since a crosslinking agent is unnecessary, the cured resin without ammonia generation can be obtained.
  • Formula 1 below is a general structure of a resol type phenol resin.
  • the isocyanate prepolymer is stirred at 5 to 20 wt% of polyol and 80 to 95 wt% of PMDI (4,4-Diphenylmethane diisocyante) to a temperature of 65 to 75 ° C. when the temperature rise no longer occurs as the reaction proceeds. Under the conditions, it is prepared by heating and stirring for 1.5 to 2.5 hours at 150 to 250 rpm, and the isocyanate prepolymer is characterized in that NCO% is 5 to 30 wt%.
  • the manufacturing process of the phenolic resin-based hard polyurethane foam foamed without using the acid curing agent according to the present invention is stirred 5 to 20wt% of the polyol (Polyol) and 80 to 95wt% of PMDI (4,4-Diphenylmethane diisocyante)
  • PMDI 4,4-Diphenylmethane diisocyante
  • 100 parts by weight to 150 parts by weight of the isocyanate prepolymer with respect to 100 parts by weight of the phenol resin is prepared by stirring at 2500 to 3500rpm to synthesize a rigid polyurethane foam.
  • the isocyanate prepolymer is added to less than 100 parts by weight with respect to 100 parts by weight of the phenol resin, the problem of outflow of unreacted phenol resin occurs, and when the isocyanate prepolymer is administered in excess of 150 parts by weight, polymerization of the isocyanate prepolymer is caused. Since there is a disadvantage in that the heat resistance is lowered, it is preferable that the amount of the isocyanate prepolymer used is limited to 100 parts by weight to 150 parts by weight based on 100 parts by weight of the phenol resin. More preferably, 110 parts by weight is used.
  • the blending ratio for synthesizing the prepolymer is shown in Table 1 below.
  • NCO% 10wt%, 15wt%, 20wt%, 24wt%, 28wt%, 30wt% prepolymer with phenolic resin
  • the foam was mixed with the polyether resin and foamed for comparison with the conventional rigid polyurethane foam.
  • the thermal stability and mechanical properties were compared.
  • Table 2 shows the stirring speed, the stirring time, the stirring ratio of the prepolymer and the polyol, and the presence / absence of foaming.
  • Phenol resin was put in 1L PE cup and 28wt% prepolymer was administered at 110 weight ratio, and the rigid urethane foam produced by stirring the mixture at 3000RPM was designated as P-1, respectively, and 30mm ⁇ 30mm ⁇ 30mm was used to check the compressive strength.
  • the density was measured by cutting the sample, and the compressive strength was measured by ASTM D1621 using a universal testing machine (UTM).
  • Hardness was used by GS-701N of TECLOCK company and the average value was measured by measuring the surface five times. The measured density, hardness and compressive strength are shown in Table 3 below.
  • Phenol resin was placed in a 1 L PE cup, and 24 wt% prepolymer was administered at a weight ratio of 110. The mixture was agitated at 3000 RPM, and the resulting rigid urethane foam was designated as P-2.
  • the density was measured by cutting the sample into 30mm ⁇ 30mm ⁇ 30mm, and the compressive strength was measured by ASTM D1621 using a universal testing machine (UTM).
  • Hardness was used by GS-701N of TECLOCK company and the average value was measured by measuring the surface five times. The measured density, hardness and compressive strength are shown in Table 4 below.
  • Phenol resin was placed in a 1 L PE cup, and a 20 wt% prepolymer was administered at a weight ratio of 110. The mixture was agitated at 3000 RPM, and the resulting rigid urethane foam was designated P-3, respectively.
  • the density was measured by cutting the sample into 30mm ⁇ 30mm ⁇ 30mm, and the compressive strength was measured by ASTM D1621 using a universal testing machine (UTM).
  • Hardness was used by GS-701N of TECLOCK company and the average value was measured by measuring the surface five times. The measured density, hardness and compressive strength are shown in Table 5 below.
  • Phenol resin was placed in a 1 L PE cup and 10 wt% prepolymer was administered at a weight ratio of 110. The mixture was agitated at 3000 RPM, and the resulting rigid urethane foam was designated as P-3.
  • the density was measured by cutting the sample into 30mm ⁇ 30mm ⁇ 30mm, and the compressive strength was measured by ASTM D1621 using a universal testing machine (UTM).
  • Hardness was used by GS-701N of TECLOCK company and the average value was measured by measuring the surface five times. The measured density, hardness and compressive strength are shown in Table 6 below.
  • a liquid prepolymer was prepared using PMDI (4,4-Diphenylmethane diisocyante) and Polyol, and then reacted with phenol resin to synthesize a phenol resin-based rigid polyurethane foam, and then Compared with urethane foam.
  • Polyester polyol was placed in a 1 L PE cup and 28% prepolymer was administered at a weight ratio of 110. The mixture was stirred at 3000 RPM, and the resulting rigid urethane foam was designated as R-1.
  • the density was measured by cutting the sample into 30mm ⁇ 30mm ⁇ 30mm, and the compressive strength was measured by ASTM D1621 using a universal testing machine (UTM).
  • Hardness was used by GS-701N of TECLOCK company and the average value was measured by measuring the surface five times. The measured density, hardness and compressive strength are shown in Table 7 below.
  • the polyester polyol was placed in a 1 L PE cup, and 24% prepolymer was administered at a weight ratio of 110. The mixture was stirred at 3000 RPM, and the resulting rigid urethane foam was designated as R-2.
  • the density was measured by cutting the sample into 30mm ⁇ 30mm ⁇ 30mm, and the compressive strength was measured by ASTM D1621 using a universal testing machine (UTM).
  • Hardness was used by GS-701N of TECLOCK company and the average value was measured by measuring the surface five times. The measured density, hardness and compressive strength are shown in Table 8 below.
  • the polyester polyol was placed in a 1 L PE cup, and 20% prepolymer was administered at a weight ratio of 110.
  • the mixture was agitated at 3000 RPM, and the resulting rigid urethane foam was designated as R-3, respectively.
  • the density was measured by cutting the sample into 30mm ⁇ 30mm ⁇ 30mm, and the compressive strength was measured by ASTM D1621 using a universal testing machine (UTM).
  • Hardness was used by GS-701N of TECLOCK company and the average value was measured by measuring the surface five times. The measured density, hardness and compressive strength are shown in Table 9 below.
  • the internal temperature of the electric furnace was increased by 100 ° C. from 100 ° C. to 800 ° C. and stored for 1 hour to measure the residual amount.
  • the hardness and the compressive strength tend to increase, and the hardness and the compressive strength are not lower than those of the conventional polyurethane foam.
  • the weight loss of the existing polyurethane foam up to 200 °C is low, but the heat resistance of the phenolic resin-based polyurethane foam was much better than 200 °C.
  • the residual amount of polyurethane foam at 800 °C was 0, but the residual amount of the phenol resin-based polyurethane foam reaches about 30%, it can be seen that the heat resistance is very excellent.
  • the hardness and the compressive strength tend to increase, and the hardness and the compressive strength are not lower than those of the conventional polyurethane foam.
  • the cutting was carried out to a size of 50mm ⁇ 20mm ⁇ 5mm, and the distance and time of burning the flame by applying the tip of the specimen for 15 seconds were measured.
  • the combustion time was measured after the heating was completed, and was measured when the flame on the surface of the urethane foam disappeared.
  • the combustion distance was measured after the end of combustion, and the flame used was blue and the flame length was maintained at 50 mm.
  • Table 10 sample Burning time (s) Combustion distance (mm) Deformation P-1 24 or more - ⁇ P-2 23 or more - ⁇ R-1 1.59 10 ⁇ R-2 1.54 0.8 ⁇
  • the combustion time was between 1.2 and 1.9 seconds, and the burning distance was 10mm ⁇ 2mm, which was shorter than the urethane foam using polyester polyol.
  • thermogravimetric analyzer TGA was used to measure the thermal stability of foams using phenolic resins.
  • the difference in the heat resistance according to the content of the measured prepolymer was not large, and it can be seen that the thermal stability of the rigid urethane foam to which the phenolic resin was added is increased compared to the conventional polyurethane foam.
  • 2 is a thermal gravimetric graph of the phenol resin foam according to the NCO% of the prepolymer (Prepolymer).
  • 3 is a graph comparing urethane foams synthesized using a polyester polyol and foams synthesized using a phenol resin.
  • TGA curve analysis of phenolic resin foam showed little difference in heat resistance in NCO%, and the heat resistance at 300 °C ⁇ 600 °C was more stable than phenolic resin than that of polyester polyol. Heat resistance in the range of °C ⁇ 500 °C showed a big difference.
  • Rigid polyurethane foam according to the present invention is excellent in thermal stability at high temperatures than conventional polyurethane foam, and does not use an acid hardener does not cause corrosion is large industrial applicability.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Cette invention concerne une mousse polyuréthanne rigide à base de résine phénolique constituée d'une résine phénolique connue présentant le problème d'être thermiquement stable à température élevée mais se cassant facilement en raison d'une basse résistance mécanique et ayant une propriété d'isolation thermique inférieure et d'une résine polyuréthanne rigide connue présentant le problème d'être douée d'une propriété d'isolation thermique et d'une résistance mécanique remarquables mais se dégradant rapidement à 200°C ou plus, les inconvénients des deux matériaux se complétant ainsi par synthèse d'une mousse polyuréthanne rigide à base de résine phénolique, la mousse selon l'invention étant en outre à l'épreuve de la corrosion par des métaux par la non-utilisation d'agents durcisseurs acides, à la différence des recherches précédemment rapportées.
PCT/KR2014/013043 2014-01-03 2014-12-30 Mousse polyuréthanne rigide à base de résine phénolique obtenue sans agent durcisseur acide et son procédé de production Ceased WO2015102373A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020140000883A KR101578059B1 (ko) 2014-01-03 2014-01-03 산 경화제를 사용하지 않고 발포한 페놀수지 기반의 경질 폴리우레탄 폼 및 이의 제조방법
KR10-2014-0000883 2014-01-03

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Cited By (4)

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CN106478915A (zh) * 2016-10-09 2017-03-08 合肥广能新材料科技有限公司 聚氨酯硬泡外墙保温材料及其制备方法
CN106497020A (zh) * 2016-10-09 2017-03-15 合肥广能新材料科技有限公司 高阻燃的聚氨酯硬泡外墙保温材料及其制备方法
CN106497021A (zh) * 2016-10-09 2017-03-15 合肥广能新材料科技有限公司 聚氨酯硬泡外墙阻燃保温材料及其制备方法
CN106496497A (zh) * 2016-10-09 2017-03-15 合肥广能新材料科技有限公司 玻化微珠聚氨酯泡沫复合材料及其制备方法

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KR101644786B1 (ko) * 2016-01-13 2016-08-12 (주)세타폼 산성 경화제가 포함되지 않은 페놀수지 발포체의 제조방법, 이에 의해 제조되는 페놀수지 발포체, 및 이를 위한 페놀수지 발포체용 조성물
KR102215628B1 (ko) * 2020-10-23 2021-02-16 이현수 드론용 프로펠러의 제조방법

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106478915A (zh) * 2016-10-09 2017-03-08 合肥广能新材料科技有限公司 聚氨酯硬泡外墙保温材料及其制备方法
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CN106497021A (zh) * 2016-10-09 2017-03-15 合肥广能新材料科技有限公司 聚氨酯硬泡外墙阻燃保温材料及其制备方法
CN106496497A (zh) * 2016-10-09 2017-03-15 合肥广能新材料科技有限公司 玻化微珠聚氨酯泡沫复合材料及其制备方法

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KR101578059B1 (ko) 2015-12-17

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