KR20230083485A - Water soluble urethane composition including epoxidized oil and isocyanate - Google Patents
Water soluble urethane composition including epoxidized oil and isocyanate Download PDFInfo
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- KR20230083485A KR20230083485A KR1020210171510A KR20210171510A KR20230083485A KR 20230083485 A KR20230083485 A KR 20230083485A KR 1020210171510 A KR1020210171510 A KR 1020210171510A KR 20210171510 A KR20210171510 A KR 20210171510A KR 20230083485 A KR20230083485 A KR 20230083485A
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- epoxidized
- oil
- urethane composition
- soluble urethane
- water
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 19
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 2
- 229920005862 polyol Polymers 0.000 claims abstract description 15
- 150000003077 polyols Chemical class 0.000 claims abstract description 15
- 229920005989 resin Polymers 0.000 claims abstract description 5
- 239000011347 resin Substances 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 239000003921 oil Substances 0.000 claims description 24
- 235000019198 oils Nutrition 0.000 claims description 24
- -1 isocyanate compound Chemical class 0.000 claims description 14
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 12
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 12
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 12
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 9
- 150000002009 diols Chemical class 0.000 claims description 8
- 239000003549 soybean oil Substances 0.000 claims description 7
- 235000012424 soybean oil Nutrition 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229920001748 polybutylene Polymers 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- 239000004568 cement Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-M 9-cis,12-cis-Octadecadienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O OYHQOLUKZRVURQ-HZJYTTRNSA-M 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 229910052925 anhydrite Inorganic materials 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 238000006735 epoxidation reaction Methods 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 229940049918 linoleate Drugs 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- 229940049964 oleate Drugs 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 239000003784 tall oil Substances 0.000 claims description 2
- 150000004072 triols Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 3
- 230000009257 reactivity Effects 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 229920002396 Polyurea Polymers 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000010276 construction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 2
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 2
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 2
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004078 waterproofing Methods 0.000 description 2
- LFTXYZVMKKPSGD-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC(O)O Chemical compound N=C=O.N=C=O.CCCCCC(O)O LFTXYZVMKKPSGD-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 239000011440 grout Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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
- C08G18/08—Processes
- C08G18/089—Reaction retarding agents
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
본 발명은 에폭시화 오일 및 이소시아네이트를 포함하는 수용성 우레탄 조성물에 관한 것으로, 폴리올 수지(주제)의 반응성은 유지하면서, 이소시아네이트(경화제)와 에폭시화 오일을 반응시켜 입체장애 효과를 통해 반응속도를 느리게 함으로써, 겔 타임(gel time)을 조절하거나 연장할 수 있다.The present invention relates to a water-soluble urethane composition containing an epoxidized oil and an isocyanate, while maintaining the reactivity of a polyol resin (subject), reacting an isocyanate (curing agent) with an epoxidized oil to slow down the reaction rate through a steric hindrance effect , the gel time can be adjusted or extended.
Description
본 발명은 에폭시화 오일 및 이소시아네이트를 포함하는 수용성 우레탄 조성물에 관한 것이다.The present invention relates to a water-soluble urethane composition comprising an epoxidized oil and an isocyanate.
폴리우레아 수지 조성물은 높은 기계적 물성을 보유하고 있기 때문에, 우레탄과 에폭시로 대표되는 유기 방수 재료에 비하여 뛰어난 내구성을 발휘할 수 있다. 기계적, 물리적, 화학적 물성이 매우 우수하고, 특히, 내마모성, 내충격성, 내수성, 내약품성이 우수하며, 시공 시에 도막의 두께를 자유롭게 조절할 수 있고 콘크리트 뿐만 아니라 철판, 알루미늄 등 다양한 피착면에 우수한 접착력을 나타낸다.Since the polyurea resin composition has high mechanical properties, it can exhibit superior durability compared to organic waterproofing materials represented by urethane and epoxy. It has excellent mechanical, physical, and chemical properties, especially excellent abrasion resistance, impact resistance, water resistance, and chemical resistance, and the thickness of the coating film can be freely adjusted during construction. indicates
일반적으로 폴리우레아 수지 조성물은 2액형으로 구성되어 이소시아네이트 프리폴리머와 아민 화합물을 가열, 혼합, 분사하여 도포시키며 경화속도가 매우 빠르다는 특징이 있다. 이러한 특징을 이용하여 고온, 고압 충돌 혼합 스프레이 전용 장비를 이용하여 스프레이 방식으로 건축물의 바탕면에 도막층을 형성하기도 한다.In general, the polyurea resin composition is composed of a two-component type and is characterized in that the isocyanate prepolymer and the amine compound are applied by heating, mixing, and spraying, and the curing speed is very fast. Using these characteristics, a coating layer is sometimes formed on the surface of a building in a spray method using equipment dedicated to high-temperature, high-pressure collision mixing spray.
하지만, 과도하게 빠른 경화 반응에 의하여 미려한 외관을 구현하기 려우며, 빠른 반응성에 따라 현장에서 스프레이 작업시 과도한 분진으로 작업자 및 환경에 유해하며, 재료의 손실이 크고, 시공시 가사 시간을 확보하기 어려우며, 바탕면의 핀홀에 대한 대응이 어려워 도막에 기포 및 들뜸 현상이 발생하여 하자가 발생하게 된다. However, it is difficult to realize a beautiful appearance due to excessively fast curing reaction, and it is harmful to workers and the environment due to excessive dust when spraying in the field according to the rapid reaction, large loss of material, and difficult to secure pot life during construction. , it is difficult to respond to pinholes on the base surface, causing bubbles and floating phenomena to occur in the coating film, resulting in defects.
또한, 빠른 경화 반응에 의해 바탕면에 스프레이 방식으로 도막을 형성한 후 자체적 평활도(self-leveling)가 이루어지지 않고 경화됨에 따라 바탕면에 시공된 폴리우레아 수지 도막에 대한 표면 수평 평활성을 얻을 수 없다는 문제점이 발생하기도 한다.In addition, after forming a coating film by spraying on the base surface by a rapid curing reaction, self-leveling is not achieved and as it hardens, it is impossible to obtain surface horizontal smoothness for the polyurea resin coating film applied to the base surface. Sometimes problems arise.
한국등록특허 제2209772호에 시멘트 광물계 지반 공사용 그라우트 조성물에 관한 기술이 개시되어 있고, 한국등록특허 제2049224호에 겔 타임 제어 가능한 에폭식 접착제에 관한 기술이 개시되어 있으며, 한국등록특허 제2043961호에 경화 반응 시간 조절이 가능한 건축물 방수용 폴리 우레아 수지 조성물에 관한 기술이 개시되어 있으나, 아직까지 본 발명의 에폭시화 오일 및 이소시아네이트를 포함하는 수용성 우레탄 조성물에 대해서 개시된 바 없다.Korean Patent No. 2209772 discloses a technology related to a grout composition for cement mineral ground construction, Korean Patent No. 2049224 discloses a technology related to an epoxy adhesive capable of controlling gel time, and Korean Patent No. 2043961 discloses A technology related to a polyurea resin composition for building waterproofing with an adjustable curing reaction time has been disclosed, but a water-soluble urethane composition containing epoxidized oil and isocyanate of the present invention has not been disclosed yet.
본 발명은 상기와 같은 요구에 의해 도출된 것으로서, 본 발명은 에폭시화 오일 및 이소시아네이트를 포함하는 수용성 우레탄 조성물을 제공하고, 본 발명에 따른 에폭시화 오일과 이소이아네이트가 반응하여 형성된 중간체가 입체적 장애 효과를 나타내 폴리올과의 반응속도를 늦춰 겔 타임(gel time)을 조절할 수 있다는 것을 확인함으로써, 본 발명을 완성하였다.The present invention has been derived from the above needs, and the present invention provides a water-soluble urethane composition containing an epoxidized oil and an isocyanate, and an intermediate formed by reacting the epoxidized oil and isocyanate according to the present invention is a steric hindrance The present invention was completed by confirming that the gel time can be adjusted by slowing down the reaction rate with the polyol by showing the effect.
상기 목적을 달성하기 위하여, 본 발명은 이소시아네이트(isosyanate) 화합물, 인산, 에폭시화 오일 및 폴리올을 포함하는 수용성 우레탄 조성물을 제공한다.In order to achieve the above object, the present invention provides a water-soluble urethane composition comprising an isocyanate compound, phosphoric acid, an epoxidized oil and a polyol.
본 발명은 에폭시화 오일 및 이소시아네이트를 포함하는 수용성 우레탄 조성물에 관한 것으로, 폴리올 수지(주제)의 반응성은 유지하면서, 이소시아네이트(경화제)와 에폭시화 오일을 반응시켜 입체장애 효과를 통해 반응속도를 느리게 함으로써, 겔 타임(gel time)을 조절하거나 연장할 수 있다.The present invention relates to a water-soluble urethane composition containing an epoxidized oil and an isocyanate, while maintaining the reactivity of a polyol resin (subject), reacting an isocyanate (curing agent) with an epoxidized oil to slow down the reaction rate through a steric hindrance effect , the gel time can be adjusted or extended.
본 발명은 이소시아네이트(isosyanate) 화합물, 인산, 에폭시화 오일 및 폴리올을 포함하는 수용성 우레탄 조성물에 관한 것이다.The present invention relates to a water-soluble urethane composition comprising an isosyanate compound, phosphoric acid, an epoxidized oil and a polyol.
상기 이소시아네이트(isosyanate) 화합물은 MDI(Methylene diphenyl diisocyanate); TDI(Toluene diisocyanate); 또는 HDI(Hexamethylene diisocyanate) 및 IPDI(Isophorone diisocyanate) 혼합물;인 것이 바람직하지만 이에 한정하는 것은 아니다. The isocyanate compound is methylene diphenyl diisocyanate (MDI); Toluene diisocyanate (TDI); or a mixture of HDI (Hexamethylene diisocyanate) and IPDI (Isophorone diisocyanate); preferably, but not limited thereto.
상기 에폭시화 오일은 식물성 오일을 에폭시화 반응을 통하여, 일정량의 에폭시기를 도입한 화합물일 수 있다. 상기 에폭시화 오일은 예를 들면, 한 분자 내 3 개의 에스터기가 포함되어 있는 트리글리세라이드 계열의 화합물일 수 있고, 일정량의 에폭시기가 함유되어 있을 수 있다. 구체적으로, 에폭시화 대두유(epoxidized soybean oil), 에폭시화 피마자유(epoxidized castor oil), 에폭시화 아마인유(epoxidized linseed oil), 에폭시화 팜유(epoxidized palm oil), 에폭시화 스테아레이트(epoxidized stearate), 에폭시화 올레이트(epoxidized oleate), 에폭시화 톨유 (epoxidized tall oil) 및 에폭시화 리놀레이트(epoxidized linoleate) 중에서 선택된 하나 이상인 것이고, 더 바람직하게는 에폭시화 메틸올레이트(epoxidized methyl oleate) 또는 에폭시화 메틸리놀레이트(epoxidized methyl linoleate)이지만 이에 제한하는 것은 아니다. The epoxidized oil may be a compound obtained by introducing a certain amount of an epoxy group through an epoxidation reaction of vegetable oil. The epoxidized oil may be, for example, a triglyceride-based compound containing three ester groups in one molecule, and may contain a certain amount of epoxy groups. Specifically, epoxidized soybean oil, epoxidized castor oil, epoxidized linseed oil, epoxidized palm oil, epoxidized stearate, It is at least one selected from epoxidized oleate, epoxidized tall oil and epoxidized linoleate, more preferably epoxidized methyl oleate or epoxidized methyl linoleate (epoxidized methyl linoleate), but is not limited thereto.
상기 에폭시화 오일과 이소시아네이트가 반응하여 형성된 중간체는 입체적으로 장애를 일으켜 폴리올과의 반응속도를 늦추는 것이 특징이다. The intermediate formed by the reaction of the epoxidized oil and isocyanate is characterized by slowing down the reaction rate with the polyol by causing steric hindrance.
상기 에폭시화 오일의 함량은 이소시아네이트(isosyanate) 화합물 100 중량부에 대하여 10~25 중량부의 에폭시화 오일을 포함하는 것이 바람직하지만 이에 한정하지 않으며, 상기 이소시아네이트 화합물 내에 NCO 함량(중량%)에 따라 에폭시화 오일의 함량이 조절될 수 있다. The content of the epoxidized oil preferably includes 10 to 25 parts by weight of epoxidized oil based on 100 parts by weight of the isocyanate compound, but is not limited thereto, and epoxidized according to the NCO content (% by weight) in the isocyanate compound. The content of oil can be adjusted.
상기 폴리올 수지는 수평균분자량 500~10,000인 폴리아크릴릭(polyacrylic) 폴리올, 폴리에테르(polyether) 폴리올, 폴리에스테르(polyester) 폴리올, 폴리부타디엔(polybuthadiene) 디올(diol), 폴리테트라 메틸렌 에테르(polytetra methylene ether) 디올, 폴리프로필렌 옥사이드(polypropylene oxide) 디올, 폴리프로필렌 옥사이드 트리올(triol), 폴리부틸렌 옥사이드(polybutylene oxide) 디올 및 폴리부틸렌 옥사이드 트리올 중에서 선택된 하나 이상인 것이 바람직하지만 이에 한정하지 않는다.The polyol resin is polyacrylic polyol having a number average molecular weight of 500 to 10,000, polyether polyol, polyester polyol, polybutadiene diol, polytetra methylene ether ) diol, polypropylene oxide diol, polypropylene oxide triol, polybutylene oxide diol, and polybutylene oxide triol.
상기 수용성 우레탄 조성물은 에폭시화 오일이 포함되지 않고, 이소시아네이트만 존재하는 경우에 대비하여 겔 타임(gel time)을 연장할 수 있으며, 이소시아네이트의 종류에 따라 겔 타임은 다르게 조절할 수 있다. 예를 들면, MDI의 경우, 에폭시화 오일과의 반응을 통해 20분에서 2시간까지 겔 타임을 연장할 수 있으며, HDI 및 IPDI 혼합물의 경우에는 1시간에서 12시간까지도 겔 타임을 연장할 수 있다. HDI의 경우 에폭시화 오일을 첨가함으로써, 흐름성은 좋아졌으나, 여전히 표면경화가 빠른 특징이 있으므로, HDI와 IPDI를 혼합하여 표면경화시간을 늘려 사용하는 것이 바람직하다. The gel time of the water-soluble urethane composition may be extended in preparation for a case in which epoxidized oil is not included and only isocyanate is present, and the gel time may be adjusted differently depending on the type of isocyanate. For example, in the case of MDI, the gel time can be extended from 20 minutes to 2 hours through reaction with epoxidized oil, and in the case of HDI and IPDI mixtures, the gel time can be extended from 1 hour to 12 hours. . In the case of HDI, flowability is improved by adding epoxidized oil, but surface hardening is still fast, so it is preferable to mix HDI and IPDI to increase surface hardening time.
상기 이소시아네이트(isosyanate) 화합물, 인산, 에폭시화 오일 및 폴리올 이외에, 시멘트, 소포제, 유동성 조절제, 유색안료, 무수석고 및 필러 중에서 선택된 하나 이상을 더 포함할 수 있으며, 이들의 혼합비율은 당업계에서 허용되는 범위에서 얼마든지 조절하여 사용할 수 있다.In addition to the isocyanate compound, phosphoric acid, epoxidized oil, and polyol, one or more selected from among cement, antifoaming agent, flow control agent, colored pigment, anhydrite, and filler may be further included, the mixing ratio of which is acceptable in the art. It can be adjusted and used as much as possible within the range.
이하, 실시예를 이용하여 본 발명을 더욱 상세하게 설명하고자 한다. 이들 실시예는 오로지 본 발명을 보다 구체적으로 설명하기 위한 것으로 본 발명의 범위가 이들에 의해 제한되지 않는다는 것은 당해 기술분야에서 통상의 지식을 가진 자에게 있어 자명한 것이다. Hereinafter, the present invention will be described in more detail using examples. These examples are only for explaining the present invention in more detail, and it is obvious to those skilled in the art that the scope of the present invention is not limited thereto.
실시예 1. 에폭시화 대두유 및 이소시아네이트 혼합에 따른 겔 타임 분석Example 1. Gel time analysis according to mixing epoxidized soybean oil and isocyanate
(1) MDI(Methylene Diphenyl diisocyanate)(1) MDI (Methylene Diphenyl diisocyanate)
표 1에 개시한 에폭시화 대두유(ESBO) 및 이소시아네이트 배합물(실험예 1 및 2)을 제조하기 위하여, 60g의 에폭시화 대두유와 530g의 폴리올 혼합물을 혼합하여 잘 섞은 후, 85%의 인산용액 0.06g을 첨가하였다. 이후, 이소시아네이트 470g을 첨가하고, 1시간 동안 서서히 90℃까지 승온시킨 후, 2시간 동안 유지하였다.In order to prepare the epoxidized soybean oil (ESBO) and isocyanate blends (Experimental Examples 1 and 2) shown in Table 1, 60 g of epoxidized soybean oil and 530 g of a polyol mixture were mixed and mixed well, followed by 0.06 g of 85% phosphoric acid solution. was added. Thereafter, 470 g of isocyanate was added, and the temperature was gradually raised to 90° C. for 1 hour, and then maintained for 2 hours.
조건에 따른 겔 타임을 분석하기 위하여, 상기 제조한 배합물 180g을 취해, 25℃에서 400rpm으로 4분 및 8분동안 교반하고, 흐름성을 확인하였다. In order to analyze the gel time according to the conditions, 180 g of the above-prepared formulation was taken, stirred at 25 ° C. at 400 rpm for 4 minutes and 8 minutes, and the flowability was confirmed.
그 결과 하기 표 1에 개시한 바와 같이 본 발명에 따른 실험예 1 및 2는 흐름성이 양호하였으나, 에폭시화 대두유를 혼합하지 않은 비교예 1 및 2의 경우, 8분 동안 교반한 후의 흐름성이 없는 상태로 굳어져 겔 타임이 매우 빠르다는 것을 확인하였고, 표면 경화시간이 2시간에서 3시간으로 늘어난 것을 확인하였다.As a result, as shown in Table 1 below, Experimental Examples 1 and 2 according to the present invention had good flowability, but in the case of Comparative Examples 1 and 2 in which epoxidized soybean oil was not mixed, the flowability after stirring for 8 minutes was It was confirmed that the gel time was very fast, and the surface hardening time was increased from 2 hours to 3 hours.
(2) HDI(Hexanediol Diisocyanate) 및 IPDI(Isophorone Diisocyanate)(2) HDI (Hexanediol Diisocyanate) and IPDI (Isophorone Diisocyanate)
혼합되는 이소시아네이트 및 에폭시화 대두유의 성분 및 함량비를 제외한 상기와 동일한 방법으로 배합물을 제조한 후, 흐름성에 대한 분석을 실시하였다.After the formulation was prepared in the same manner as above except for the components and content ratios of isocyanate and epoxidized soybean oil to be mixed, flowability was analyzed.
그 결과, 하기 표 2에 개시한 바와 같이 HDI의 경우는 ESBO를 혼합하지 않으면 빨리 경화되어 8분 동안 교반한 후 흐름성이 없는 것으로 나타났다. 하지만, IPDI의 경우는 ESBO를 혼합하지 않더라도 경화시간이 길어 8분 동안 교반한 후에도 흐름성이 양호한 것으로 나타났다. 따라서 IPDI는 겔 타임 조절이 필요하지 않는 것으로 판단하였다.As a result, as shown in Table 2 below, in the case of HDI, when ESBO was not mixed, it was quickly cured, and after stirring for 8 minutes, it was found that there was no flow. However, in the case of IPDI, even if ESBO was not mixed, the hardening time was long, and the flowability was good even after stirring for 8 minutes. Therefore, IPDI judged that gel time adjustment was not necessary.
한편, 표 2의 실험예 3에 개시한 바와 같이, HDI와 ESBO를 혼합하더라도 표면경화시간 조절이 되지 않아, HDI의 경우는 IPDI와 ESBO를 둘 다 혼합하여 사용하였을 때 흐름성 뿐만 아니라 표면 경화 시간을 조절할 수 있는 것으로 판단하였다. On the other hand, as disclosed in Experimental Example 3 of Table 2, even if HDI and ESBO are mixed, the surface hardening time cannot be controlled. In the case of HDI, when both IPDI and ESBO are mixed and used, not only the flowability but also the surface hardening time was judged to be controllable.
Claims (7)
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