KR0142148B1 - Water repellant composition - Google Patents

Water repellant composition

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Publication number
KR0142148B1
KR0142148B1 KR1019940039754A KR19940039754A KR0142148B1 KR 0142148 B1 KR0142148 B1 KR 0142148B1 KR 1019940039754 A KR1019940039754 A KR 1019940039754A KR 19940039754 A KR19940039754 A KR 19940039754A KR 0142148 B1 KR0142148 B1 KR 0142148B1
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South Korea
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water
water repellent
soluble
aminoethyl
repellent composition
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KR1019940039754A
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Korean (ko)
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KR960022927A (en
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정일남
조연선
한준수
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김은영
한국과학기술연구원
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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
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1681—Antifouling coatings characterised by surface structure, e.g. for roughness effect giving superhydrophobic coatings or Lotus effect

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Combustion & Propulsion (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)

Abstract

다음 일반식 (Ⅰ)의 1,1,1-트리메톡시-3-아릴-1-실라부탄을 함유하는 수용성 발수제 조성물, 본 발명의 수용성 발수제 조성물은 1,1,1-트리메톡시-3-아릴-1-실라부탄, 메틸트리메톡시실란 및 N-(2-아미노에틸)-3-아미노프로필트리멕토시실란을 총 조성 물 무게에 대해 2 내지 40%의 범위 내에서 적절한 몰비로 함유한다.The water-soluble water repellent composition containing the following 1,1,1-trimethoxy-3-aryl-1-silabutane of the general formula (I), the water-soluble water repellent composition of the present invention is 1,1,1-trimethoxy-3 -Aryl-1-silabutane, methyltrimethoxysilane and N- (2-aminoethyl) -3-aminopropyltrimethocysilane, in appropriate molar ratios within the range of 2-40% by weight of the total composition do.

(식 중, R은 수소, 플루오로 또는 페녹시기를 나타낸다)(Wherein R represents hydrogen, fluoro or phenoxy group)

Description

다공성 건축용 석재의 표면처리용 수용성 발수제 조성물Water-soluble water repellent composition for surface treatment of porous building stone

본 발명은 다음 일반식 (Ⅰ)의 1,1,1-트리메톡시-3-아릴-1-실라부탄을 함유하는 수용성 발수제 조성물에 관한 것이다. 더욱 구체적으로는, 본 발명은 1,1,1-트리메톡시-3-아릴-1-실라부탄, 메틸트리메톡시실란 및 N-(2-아미노에틸)-3-아미노프로필트리멕토시실란을 적절한 몰비로 함유하는 발수제 조성물에 관한 것이다.The present invention relates to a water-soluble water repellent composition containing 1,1,1-trimethoxy-3-aryl-1-silabutane of the following general formula (I). More specifically, the present invention relates to 1,1,1-trimethoxy-3-aryl-1-silabutane, methyltrimethoxysilane and N- (2-aminoethyl) -3-aminopropyltrimethocysilane It relates to a water repellent composition containing in an appropriate molar ratio.

(식 중, R은 수소, 플루오로 또는 페녹시기이다)Wherein R is hydrogen, fluoro or phenoxy group

발수제는 오늘날 건축재료로서 중요한 부분을 차지하고 있는 콘크리트, 벽돌, 타일등의외부를 물로부터 보호하는 중요한 역할을 한다. 콘크리트, 벽돌, 타이들은 미세한 구멍들을 많이 가지고 있기 때문에 쉽게 수분이 흡수되는 단점을 가지고 있다. 벽면에 흡수된 수분은 단열효과를 저하시키고, 팽창, 수축등으로 인하여 벽면을 갈라지게 하거나 타일과 같은 외장재를 벽면으로부터 떨어뜨릴 뿐 아니라 얼룩을 만들어 외관을 해치고, 내부의 철분을 건축물의 수명을 단축시키기도 한다. 따라서 이러한 문제점을 해결하기 위해 여러가지 방법이 이용되고 있는데, 그 중 하나가 벽면을 발수제로 처리하는 것이다.Water repellents play an important role in protecting the exterior of concrete, bricks and tiles, which are an important part of today's building materials. Concrete, bricks, and ties have the disadvantage of easily absorbing moisture because they have many fine holes. Moisture absorbed on the wall lowers the thermal insulation effect, and not only cracks the wall surface due to expansion and contraction, but also drops the exterior materials such as tiles from the wall, stains the exterior, and reduces the life of the building iron. Sometimes. Therefore, various methods are used to solve this problem, one of which is to treat the wall surface with a water repellent.

종래 발수제로는 기름, 왁스, 비누, 수지, 유기규소 화합물들을 사용하여 이를 붓이나 롤러, 분사등의 방법에 의해 처리하여 왔다. 그러나, 유기규소 화합물이 아닌 유기발수제인 경우, 건축재료에 피막을 형성시키면서 건축재료의 미세한 구멍들을 막아버려 통기성을 저하시키므로 건축물의 외기에 대한 적응을 어렵게 하며, 색상과 같은 외관에 변화를 준다. 그러나 유기규소계 발수제는 아주 묽은 용액으로 처리해도 효과가 좋으므로 색상에 변화를 주지않고 건축재료와 화학적인 결합을 함으로써 반영구적으로 발수 효과를 얻을 수 있다.Conventional water repellents have been treated with oil, wax, soap, resins, organosilicon compounds and by brush, roller, spray or the like. However, in the case of an organic water repellent rather than an organosilicon compound, it is difficult to adapt to the outside air of the building and change the appearance such as color by blocking the minute pores of the building material while forming a film on the building material, thereby reducing the breathability. However, the organosilicon-based water repellent is effective even if it is treated with a very thin solution, and thus can be semi-permanently obtained by chemically bonding with building materials without changing the color.

유기규소계 발수제는 유기발수제처럼 건축재의 미세한 구멍을 막음으로서 발수효과를 나타내는 것이 아니고 극히 적은양이 구멍 깊숙히 침투하여 건축재와 반응함으로써 매우 엷은 피막을 형성하여 발수효과를 내게하는 것이다. 그러므로 액체 상태의 물은 스며들지 못하나 수증기나 기체는 통과시키기 때문에 건축재의 호흡작용에 지장을 주지 않는다.The organosilicon-based water repellent does not exhibit water repellent effect by blocking the minute hole of the building material like the organic water repellent, but very small amount penetrates deep into the hole and reacts with the building material to form a very thin film to give a water repellent effect. Therefore, liquid water does not penetrate, but it does not interfere with the breathing of building materials because it passes water vapor or gas.

현재 이용되고 있는 유기규소계 발수제는 크게 유성과 수용성으로 구분된다.Organosilicon-based water repellents currently used are largely divided into oil and water soluble.

미국특허 제3,389,206호와 4,002,800호에는 알킬트리알콕시시리란에 아미노프로필트 리에톡시실란이나 부틸티타네이트를 첨가하여 알콜이나 유기용매에 녹인 유성 유기규소계 발수제가 개시되어 있다. 또한 미국특허 제4,846,886호 4,874,431호에는 알킬알콕시시란과 N-(2-아미노에틸)-3-아미노프로필트리메톡시실란을 물이 아닌 아콜이나 글리콜로 녹인 유성발수제가 보고되어 있다. 이러한 유성 발수제는 유기용제를 사용하여야 하므로 가격면에서 불리하고 화재의 위험과 공해요인이 있다. 본 발명에 의한 발수제는 유기용제 대신 물을 사용하므로 이러한 단점이 극복된 개선된 조성물이다.U.S. Patent Nos. 3,389,206 and 4,002,800 disclose oily organosilicon-based water repellents which are dissolved in an alcohol or an organic solvent by adding aminopropyl triethoxysilane or butyl titanate to an alkyltrialkoxy silane. U.S. Patent No. 4,846,886 4,874,431 also reports oil-based water repellents in which alkylalkoxysilane and N- (2-aminoethyl) -3-aminopropyltrimethoxysilane are dissolved in acol or glycol instead of water. Since these oil-based water repellents must use organic solvents, they are disadvantageous in terms of price, risk of fire and pollution. The water repellent according to the present invention is an improved composition that overcomes these disadvantages because water is used instead of organic solvents.

미국특허 제3,914,476호에서는 알칼리금속 유기실리코네이트의 수용액을 건축재에 처리할 경우 우수한 발수성이 나타난다고 보고된 바 있다. 이들 나트륨 또는 칼륨 유기실리코네이트를 건축재의 표면에 처리하면 알칼리는 공기 중의 탄산가스와 중화되어 건축재료의 표면에 얇은 수지 피막이 형성되어 발수효과가 나타나게 된다. 이러한 형태의 발수제는 강알칼리를 사용하여야 하므로 취급이 어렵다는 단점이 있다.U.S. Patent No. 3,914,476 reports that excellent water repellency is observed when an aqueous solution of an alkali metal organosiliconate is applied to a building material. When these sodium or potassium organosiliconates are treated on the surface of the building material, the alkali is neutralized with carbon dioxide gas in the air, and a thin resin film is formed on the surface of the building material, resulting in a water repellent effect. This type of water repellent has a disadvantage in that it is difficult to handle because strong alkali must be used.

한편, 이러한 단점을 개선한 수용성 발수제가 미국특허 5,073,195호에 개시되어 있는데 이 특허에서는 N-(2-아미노에틸)-3-아미노플로필트리멕톡시실란과 같은 수용성 실란 커플링제와 발수성기를 가진 알킬트리알콕시실란을 함께 중합시킨 수용성 발수제가 개시되어 있다.On the other hand, a water-soluble water repellent which improves this disadvantage is disclosed in US Patent No. 5,073,195, which discloses an alkyl having a water-repellent group and a water-soluble silane coupling agent such as N- (2-aminoethyl) -3-aminoflofiltrimethoxysilane A water soluble water repellent in which a trialkoxysilane is polymerized together is disclosed.

본 발명자들은 일반식(Ⅱ)와 같은 2-(아릴프로필)-트리클로로실란을 메탄올로 메톡시화시켜 얻은 일반식 (Ⅰ)의 2-(아릴프로필)트리메톡시시란, 메틸트리멕톡시시란 및 N-(2-아미노에틸)-3)아미노프로필트리메톡시실란을 발수제 조성물 총 무게에 대해 2 내지 40 무게 %의 범위 에서 적당한 몰 비율로 혼합하여 함께 중합시키면 물에 잘 녹으면서도 발수성이 우수한 수용성 발수제를 얻을 수 있음을 발견하여 본 발명을 완성하기에 이르렀다. 본 발명에서 발수제 성분으로 사용하는 일반식 (Ⅰ)의 화합물의 2-아릴프로필기는 메틸이나 프로필 치환체보다 유성이 강하기 때문에 소량만 첨가하여도 우수한 발수성을 나타낸다.MEANS TO SOLVE THE PROBLEM The present inventors calculated | required 2- (arylpropyl) trimethoxysilane of the general formula (I) obtained by methoxylating 2- (arylpropyl)-trichlorosilane like general formula (II), and methyltrimethoxy city. When the lan and N- (2-aminoethyl) -3) aminopropyltrimethoxysilane are mixed and polymerized together in a suitable molar ratio in the range of 2 to 40% by weight relative to the total weight of the water repellent composition, it is well soluble in water and water repellent. The discovery that an excellent water-soluble water repellent can be obtained has led to the completion of the present invention. Since the 2-arylpropyl group of the compound of the general formula (I) used as the water repellent component in the present invention is more oily than methyl or propyl substituents, even when only a small amount is added, it exhibits excellent water repellency.

(식 중, R은 수소, 플루오로, 또느 페녹시기이다)Wherein R is hydrogen, fluoro or phenoxy group

다음에 실시예를 들어 본 발명을 더욱 상세히 설명할 것이나 본 발명이 이들 실시예로 국한되는 것은 아니다.The present invention will be described in more detail with reference to the following Examples, but the present invention is not limited to these Examples.

[실시예 1]Example 1

1,1,1-트리메톡시-3-페닐-1-실라부탄을 포함하는 수용성 발수제 조성물의 제조Preparation of Water-soluble Water Repellent Composition Comprising 1,1,1-Trimethoxy-3-phenyl-1-Silabutane

1,1,1-트리메톡시-3-페닐-1-실라부탄, 메틸트리메톡시실란, N-(2-아미노에틸)-3-아미노프로필트리메톡시실란 및 물을 1.0:9.0: 10:20, 1.0:14:15:30 및 1.0:19:20:40:의 다양한 몰 비율로 혼합한 후 10분간 교반시켰다. 이 혼합물을 60℃항온조가 장치된 회전 증발기로 메탄올을 제거시키면서 가수분해 반응을 수행하였다. 가수분해 되는 남은 잔유물의 무게비율이 10%가 되게 물로 희석하였다.1,1,1-trimethoxy-3-phenyl-1-silabutane, methyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane and water were 1.0: 9.0: 10 After mixing at various molar ratios of: 20, 1.0: 14: 15: 30 and 1.0: 19: 20: 40 :, the mixture was stirred for 10 minutes. The mixture was subjected to a hydrolysis reaction while removing methanol on a rotary evaporator equipped with a 60 ° C. thermostatic bath. The weight ratio of the remaining residue to be hydrolyzed was diluted with water.

[실시예 2]Example 2

1,1,1-트리메톡시-3-(플루로로페닐)-1-실라부탄을 포함하는 수용성 발수제 조성물의 제조Preparation of Water-soluble Water Repellent Composition Comprising 1,1,1-Trimethoxy-3- (Flurophenyl) -1-Silabutane

1,1,1-트리메톡시-3-(플루오로페닐)-1-실라부탄, 메틸트리메톡시실란, N-(2-아미노에틸)-3-아미노프로필트리메톡시실란 및 물을 1.0:9.0: 10:20, 1.0:14:15:30 및 1.0:19:20:40:의 다양한 몰 비율로 혼합한 후 10분간 교반시켰다. 그 외의 과정은 실시예 1과 같이 수행하였다.1,1,1-trimethoxy-3- (fluorophenyl) -1-silabutane, methyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane and 1.0 water After mixing at various molar ratios of: 9.0: 10: 20, 1.0: 14: 15: 30 and 1.0: 19: 20: 40 :, the mixture was stirred for 10 minutes. Other procedures were carried out as in Example 1.

[실시예 3]Example 3

1,1,1-트리메톡시-3-(페녹시페닐)-1-실라부탄을 포함하는 수용성 발수제 조성물의 제조Preparation of a water-soluble water repellent composition comprising 1,1,1-trimethoxy-3- (phenoxyphenyl) -1-silabutane

1,1,1-트리메톡시-3-(페녹시페닐)-1-실라부탄, 메틸트리메톡시실란, N-(2-아미노에틸)-3-아미노프로필트리메톡시실란 및 물을 1.0:9.0: 10:20, 1.0:14:15:30 및 1.0:19:20:40:의 다양한 몰비율로 혼합한 후 10분간 교반시켰다. 그 외의 과정은 실시예 1과 같이 수행하였다.1,1,1-trimethoxy-3- (phenoxyphenyl) -1-silabutane, methyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane and 1.0 water After mixing at various molar ratios of: 9.0: 10: 20, 1.0: 14: 15: 30 and 1.0: 19: 20: 40 :, the mixture was stirred for 10 minutes. Other procedures were carried out as in Example 1.

[실시예 4]Example 4

1,1,1-트리메톡시-3-아릴-1-실라부탄을 포함하는 수용성 발수제 조성물의 발수성 조사Water repellency investigation of the water-soluble water repellent composition comprising 1,1,1-trimethoxy-3-aryl-1-silabutane

약 35g되는 붉은색 건축용 벽돌조각, 콘크리트,모르타르 및 석고판을 이용하여 발수성을 측정하였다. 다양한 몰비율로 제조된 발수액에 벽돌조각을 실온에서 30분간 담근 뒤 실온에서 24시간 동안 건조시켰다. 이 조각들을 실온에서 1시간 동안 물에 담근 다음 휴지로 표면에 묻어있는 물기를 제거한 뒤 15분간 실온에서 건 시킨 후 물 흡수율을 측정하였다. 계속해서 실온에서 12시간 동안 건조시킨 다음 물을 측정하여 물 함유율을 측정하였다. 여러 조성에 따른 각각의 결과를 표 1 내지 4에 나타내었다.Water repellency was measured using red brick pieces, concrete, mortar and gypsum board of about 35g. Brick pieces were immersed in water-repellent solution prepared at various molar ratios for 30 minutes at room temperature and dried for 24 hours at room temperature. The pieces were soaked in water for 1 hour at room temperature, and then dried on a surface with a tissue, dried at room temperature for 15 minutes, and water absorption was measured. It was then dried at room temperature for 12 hours and then water was measured to determine the water content. The results of each of the various compositions are shown in Tables 1-4.

이하 표 1 내지 표 4에서 표기한 약자는 다음과 같다.Hereinafter, the abbreviations indicated in Tables 1 to 4 are as follows.

Y:1,1,1-트리메톡시-3-아릴-1-실라부탄Y: 1,1,1-trimethoxy-3-aryl-1-silabutane

(시료번호 1, 2, 3:아릴=페닐,(Sample numbers 1, 2, 3: aryl = phenyl,

시료번호 4, 5, 6:아릴=플루오로페닐Sample numbers 4, 5 and 6: aryl = fluorophenyl

시료번호 7, 8, 9:아릴=페녹시페닐)Sample No. 7, 8, 9: Aryl = Phenoxyphenyl)

A:메틸트리메톡시실란A: methyltrimethoxysilane

B:N-(2-아미노에틸)-3-아미노프로필트리메톡시시란B: N- (2-aminoethyl) -3-aminopropyltrimethoxysilane

C;물C; water

대조군:발수처리를 하지 않는 시료Control group: Sample without water repellent treatment

Claims (3)

다음 일반식 (Ⅰ)의 유기실란 메틸트리메톡시실란 및 N-(2-아미노에틸)-3-아미노프로필트리메톡시실란을 1.0:9.0:10 내지 1.0:19:20의 몰비로 함유하는 다공성 건축용 석재의 표면처리용 수용성 발수제 조성물Porous containing the organosilane methyltrimethoxysilane and N- (2-aminoethyl) -3-aminopropyltrimethoxysilane of the following general formula (I) in a molar ratio of 1.0: 9.0: 10 to 1.0: 19: 20 Water-soluble water repellent composition for surface treatment of building stone (식 중, R은 수소, 플루오로 또는 페녹시기를 나타낸다)(Wherein R represents hydrogen, fluoro or phenoxy group) 제1항에 있어서, 일반식 (Ⅰ)의 화합물, 메틸트리메톡시실란, 및 N-(2-아미노에틸)-3-아미노프로필트리멕토시실란이 총 조성물 무게에 대해 2 내지 40%의 비율로 존재하는 수용성 발수제 조성물.The compound of formula (I), methyltrimethoxysilane, and N- (2-aminoethyl) -3-aminopropyltrimethocysilane are in a ratio of 2 to 40% by weight of the total composition. Water-soluble water repellent composition present. 제1항 또는 2항에 있어서, 다공성 건축용 석재가 붉은 벽돌, 콘크리트, 모르타르 및 석고판 중에서 선택되는 것이 특징인 수용성 발수제 조성물.The water-soluble water repellent composition according to claim 1 or 2, wherein the porous building stone is selected from red brick, concrete, mortar and gypsum board.
KR1019940039754A 1994-12-30 1994-12-30 Water repellant composition KR0142148B1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102449752B1 (en) 2022-08-18 2022-09-30 선유규 Water based water repellent agent manufacturing method and carring out method using thereof
US11807776B2 (en) 2017-12-19 2023-11-07 Kyungpook National University Industry-Academic Cooperation Foundation Modified siloxane resin, modified siloxane resin crosslinked product, and manufacturing method for resin crosslinked product

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11807776B2 (en) 2017-12-19 2023-11-07 Kyungpook National University Industry-Academic Cooperation Foundation Modified siloxane resin, modified siloxane resin crosslinked product, and manufacturing method for resin crosslinked product
KR102449752B1 (en) 2022-08-18 2022-09-30 선유규 Water based water repellent agent manufacturing method and carring out method using thereof

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