KR102387259B1 - Alkoxysilane compounds having hydrophilic functional group and polydimethylsiloxane derivative compositions capable of forming hydrophilic surfaces - Google Patents

Alkoxysilane compounds having hydrophilic functional group and polydimethylsiloxane derivative compositions capable of forming hydrophilic surfaces Download PDF

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KR102387259B1
KR102387259B1 KR1020190179620A KR20190179620A KR102387259B1 KR 102387259 B1 KR102387259 B1 KR 102387259B1 KR 1020190179620 A KR1020190179620 A KR 1020190179620A KR 20190179620 A KR20190179620 A KR 20190179620A KR 102387259 B1 KR102387259 B1 KR 102387259B1
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김주영
최용환
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강원대학교 산학협력단
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Abstract

본 발명은 아민기 또는 히드록시기를 가지는 친수성 화합물(A)과 에폭시기 또는 이소시아네이트기를 가지는 알콕시 실란화합물(B)을 반응시켜 제조되는 친수성 유기관능기를 가지는 알콕시 실란화합물을 제공하는 한편, 친수성 유기관능기를 가지는 알콕시 실란화합물과 히드록시기를 가지는 폴리디메틸실록산(PDMS)을 축합 반응시켜 제조되는 것을 특징으로 하는, 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물을 제공한다.The present invention provides an alkoxysilane compound having a hydrophilic organic functional group prepared by reacting a hydrophilic compound (A) having an amine group or a hydroxyl group and an alkoxysilane compound (B) having an epoxy group or an isocyanate group, while an alkoxy having a hydrophilic organic functional group Provided is a polydimethylsiloxane derivative compound capable of forming a hydrophilic surface, characterized in that it is prepared by a condensation reaction of a silane compound and polydimethylsiloxane (PDMS) having a hydroxyl group.

Description

친수성 유기관능기를 가지는 알콕시 실란화합물 및 이를 이용한 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물{Alkoxysilane compounds having hydrophilic functional group and polydimethylsiloxane derivative compositions capable of forming hydrophilic surfaces}Alkoxysilane compounds having hydrophilic organic functional groups and polydimethylsiloxane derivative compounds capable of forming a hydrophilic surface using the same

본 발명은 친수성 유기관능기가 도입된 폴리디메틸실록산(polydimethysiloxane, 이하 'PDMS') 유도체 화합물에 관한 것으로, 강한 소수성 고분자 물질인 PDMS을 개질하여 경화된 표면에 강한 친수성(또는 양친성)을 형성함으로써 유기고분자나 금속과 같은 다른 피착제와 물리적으로 부착 또는 접착할 수 있는 PDMS 유도체 화합물에 관한 것이다.The present invention relates to a polydimethylsiloxane (hereinafter referred to as 'PDMS') derivative compound into which a hydrophilic organic functional group is introduced. By modifying PDMS, which is a strong hydrophobic polymer material, strong hydrophilicity (or amphiphilicity) is formed on the cured surface. It relates to a PDMS derivative compound capable of physically adhering or adhering to other adherends such as polymers or metals.

과학기술 및 산업의 고도화가 진행됨에 따라 점점 고 물성의 우수한 재료들이 요구되고 있다. 이 중 고분자 재료는 용도에 따라 다양한 종류로 합성할 수 있으며, 필요에 따라 새로운 합성 기술로 여러 가지 제품이 개발되고 있다. 그 중에서도 실리콘 재료는 다른 재료에 비해 역사가 오래되지는 않았지만, 최근 환경 문제가 대두되면서 실리콘 재료는 현재 여러 분야에서 사용되고 있다. 이 중에서 실리콘 재료 중 하나인 PDMS는 표면장력이 낮아 평활성이 좋은 실리콘 수지로 화학 안정성, 우수한 내열성 및 성형성 뿐 아니라 친환경적이며, 생체 적합성과 안정성, 무독성, 광학적 투명성이 우수하여 부식방지코팅, 생체 재료 등 여러 분야에서 널리 사용되고 있다 [1-5].As science and technology and industry advance, high-quality materials with high physical properties are increasingly required. Among them, polymer materials can be synthesized in various types depending on the use, and various products are being developed with new synthesis technology as needed. Among them, silicone materials do not have a long history compared to other materials, but as environmental problems have recently emerged, silicone materials are currently being used in various fields. Among them, PDMS, one of the silicone materials, is a silicone resin with good smoothness due to its low surface tension. It is environmentally friendly as well as chemical stability, excellent heat resistance and moldability. It is widely used in various fields such as [1-5] .

Figure 112019136166164-pat00001
Figure 112019136166164-pat00001

< PDMS (Polydimethysiloxane) >< PDMS (Polydimethysiloxane) >

그러나 PDMS 수지의 낮은 표면에너지 (약 20 μJ/㎡, 물 접촉각 약 120˚)와 표면에 반응할 수 있는 작용기가 적기 때문에 다른 유기물질이나 금속 물질과의 부착이 어렵다는 단점이 있다[6,7]. 특히, 생체재료나 의료기기에 이용할 경우 PDMS가 생체 적합성과 안정성이 우수하지만, 소수성이 강하기 때문에 미생물이나 다른 생물막 형성에 있어 어려움을 겪고 있다[8-10]. 따라서 PDMS 표면을 변화시켜서 PDMS의 여러 가지 단점을 해결하기 위한 다양한 연구가 수행되어져 왔다. 일반적으로 PMDS 표면에 작용기를 도입하기 위해 산소 플라즈마(O2 plasma) 처리, 코로나(Corona) 처리, UV 조사, 전기방전(Electrical discharge) 등을 통해 표면을 개질시키며[8, 11-13], 이 중에서도 대부분 O2 plasma 처리를 통해 PDMS 표면에 히드록시기(-OH group)를 생성시키고, -OH group으로 개질된 PDMS 필름은 다른 유기고분자나 금속 등의 피착제와 물리적으로 부착을 시키거나, 커플링제를 이용하여 다른 물질과의 부착을 용이하게 하는 방법을 사용한다. PDMS의 표면처리 방법에는 전술한 것처럼, 물리적인 방법과 화학적인 방법이 있다. 물리적인 방법으로 PDMS를 표면처리 하는 방법은 표면에너지가 낮은 PDMS 필름 위에 상대적으로 표면에너지가 낮은 고분자 피착제를 부착시켜 표면을 개질시키는 방법이며, O2 plasma로 처리를 통해 표면에 -OH group을 생성시키고, 피착제에도 O2 plasma 또는 Corona 처리를 함으로써 PDMS 필름과 피착제를 부착시키는 방법을 사용하거나, Plasma 처리된 PDMS 필름에 작용기가 있는 단분자 유기 실란과 Condensation 반응을 통해 표면에 작용기가 배향시킨 후, 이를 피착제와 함께 Corona 처리를 하여 -OH group을 표면에 생성시키고 부착시켜 PDMS 필름 표면에 표면에너지가 높은 피착제를 도입함으로써 다른 유기물질과의 부착을 높이는 방법이 사용된다[14]. However, the low surface energy (about 20 μJ/m2, water contact angle of about 120˚) of the PDMS resin and the small number of functional groups that can react on the surface make it difficult to adhere to other organic or metallic materials [6,7] . In particular, when used for biomaterials or medical devices, PDMS has excellent biocompatibility and stability, but has difficulties in forming microorganisms or other biofilms because of its strong hydrophobicity [8-10] . Therefore, various studies have been conducted to solve the various shortcomings of PDMS by changing the PDMS surface. In general, to introduce functional groups to the surface of PMDS, the surface is modified through oxygen plasma treatment, corona treatment, UV irradiation, electrical discharge, etc. [8, 11-13] , Among them, most of them generate a hydroxyl group (-OH group) on the PDMS surface through O 2 plasma treatment, and the PDMS film modified with the -OH group is physically attached to an adherend such as another organic polymer or metal, or a coupling agent is used. A method that facilitates adhesion to other materials is used. As described above, the surface treatment method of PDMS includes a physical method and a chemical method. The physical method of surface treatment of PDMS is a method of modifying the surface by attaching a polymer adherend with a relatively low surface energy on a PDMS film with a low surface energy. Orientation of functional groups on the surface through condensation reaction with monomolecular organosilane having functional groups on the plasma-treated PDMS film or using the method of attaching the PDMS film and the adherend by treating the adherend with O 2 plasma or Corona. After this, a method is used to increase adhesion with other organic materials by introducing an adherend with high surface energy to the surface of the PDMS film by corona-treating it with the adherend to generate and attach -OH groups to the surface [14] .

화학적인 방법으로 PDMS 필름의 표면처리 하는 방법에는 O2 plasma 처리한 PDMS 필름과 작용기를 가지면서 알콕시 실란을 동시에 가지는 유기물인 커플링제 사이의 축합 반응을 통해 PDMS 필름 표면에 작용기를 도입시키는 방법이 있다. 축합 반응의 경우, 가수분해(Hydrolysis) 반응을 통해 커플링제가 가지고 있는 알콕시 실란이 실라놀(Silanol, Si-OH)로 바뀌면서 표면이 개질된 PDMS 필름과 축합하는 방법과 알콕시 실란 자체를 개질된 PDMS 필름 표면에 축합하는 방법을 사용하여 최종적으로 PDMS 필름 맨 윗부분에 작용기를 도입시킴으로써 다른 유기물질과의 부착을 높일 수 있다.A method for surface treatment of a PDMS film by a chemical method is to introduce a functional group to the surface of the PDMS film through a condensation reaction between the O 2 plasma-treated PDMS film and a coupling agent, which is an organic material having a functional group and an alkoxysilane at the same time. . In the case of the condensation reaction, the method of condensing the PDMS film with the modified surface as the alkoxysilane possessed by the coupling agent is changed to silanol (Si-OH) through the hydrolysis reaction, and the method of condensing the alkoxysilane itself with the modified PDMS By using the method of condensation on the film surface and finally introducing a functional group to the top of the PDMS film, adhesion with other organic materials can be enhanced.

또 다른 방법으로는 그라프팅 중합(Grafting polymerization)을 통해 고분자 사슬을 PDMS 표면위에 Self-Assembly Monolayer(SAM) 형태로 형성시켜 표면을 개질시키는 방법이 있으며[15], 그라프팅 방법은 Grafting-to, Grafting-from이 있다. Grafting-to는 원하는 길이의 주사슬과 곁사슬 고분자를 각각 합성한 뒤 곁사슬 말단 작용기와 주사슬 작용기 간의 결합을 형성하여 제조하는 방법이고, Gafting-from은 라디칼을 포함하는 단량체로 사슬을 제조하고 이후 각 개시 작용기에서 곁사슬 중합을 통해 제조하는 방법이다[16]. 하지만, PDMS의 경우 표면에 작용기가 없기 때문에 Grafting 시킬 때 라디칼을 가진 곁사슬이 PDMS에 Grafting 하는 것이 힘들기 때문에 Grafting 시키는 경우에도 PDMS 필름이나 사슬에 라디칼이 필요하게 되며, 이로 인해 공정이 더욱 복잡해질 수 있다. 따라서 이러한 복잡한 화학적 공정을 사용하지 않고 기존의 폴리디메틸실록산 경화 공정만을 이용하여도 친수성 표면을 형성할 수 있는 새로운 폴리디메틸실록산 유도체 제조 방법이 절실히 필요하다.Another method is to modify the surface by forming a polymer chain in the form of Self-Assembly Monolayer (SAM) on the PDMS surface through grafting polymerization [15] . There is Grafting-from. Grafting-to is a method for manufacturing by synthesizing a main chain and a side chain polymer of a desired length, respectively, and then forming a bond between the side chain terminal functional group and the main chain functional group. It is a method prepared through side chain polymerization at the initiating functional group [16] . However, in the case of PDMS, since there is no functional group on the surface, it is difficult to graft side chains with radicals to PDMS during grafting. there is. Therefore, there is an urgent need for a new method for preparing a polydimethylsiloxane derivative capable of forming a hydrophilic surface using only the existing polydimethylsiloxane curing process without using such a complicated chemical process.

본 발명은 전술한 문제점을 해결하기 위한 것으로, 종래와 같이 복잡한 표면 처리 공정이나 화학적 반응을 사용하지 않고도 일반적인 PDMS 전구체들의 축합반응 공정만을 이용하여 친수성 표면을 형성할 수 있는 폴리디메틸실록산 유도체 화합물 및 이의 제조 방법을 제공하는 것을 목적으로 한다.The present invention is to solve the above-mentioned problems, and a polydimethylsiloxane derivative compound capable of forming a hydrophilic surface using only a condensation reaction process of general PDMS precursors without using a complex surface treatment process or chemical reaction as in the prior art, and a compound thereof It aims to provide a manufacturing method.

상기 목적을 달성하기 위하여, 본 발명은 본 발명은 친수성 유기관능기를 가지는 알콕시 실란화합물과 히드록시기를 가지는 폴리디메틸실록산(PDMS)을 축합 반응시켜 제조되는 것을 특징으로 하는, 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물을 제공한다.In order to achieve the above object, the present invention provides a polydimethylsiloxane capable of forming a hydrophilic surface, characterized in that it is prepared by a condensation reaction of an alkoxysilane compound having a hydrophilic organic functional group and polydimethylsiloxane (PDMS) having a hydroxyl group. Derivative compounds are provided.

상기 친수성 유기관능기를 가지는 알콕시 실란화합물은 아민기 또는 히드록시기를 가지는 친수성 화합물(A)과 에폭시기 또는 이소시아네이트기를 가지는 알콕시 실란화합물(B)을 반응시켜 제조될 수 있다.The alkoxysilane compound having a hydrophilic organic functional group may be prepared by reacting a hydrophilic compound (A) having an amine group or a hydroxyl group and an alkoxysilane compound (B) having an epoxy group or an isocyanate group.

상기 아민기 또는 히드록시기를 가지는 친수성 화합물(A)에서 친수성 성분은 폴리에틸렌글리콜일 수 있다. 상기 아민기 또는 히드록시기를 가지는 친수성 화합물(A)은 하기 화학식 1 내지 6으로 표시되는 화합물 중에서 선택되는 1종 이상일 수 있다.In the hydrophilic compound (A) having an amine group or a hydroxyl group, the hydrophilic component may be polyethylene glycol. The hydrophilic compound (A) having an amine group or a hydroxyl group may be at least one selected from compounds represented by Formulas 1 to 6 below.

[화학식 1][Formula 1]

Figure 112019136166164-pat00002
Figure 112019136166164-pat00002

[화학식 2][Formula 2]

Figure 112019136166164-pat00003
Figure 112019136166164-pat00003

[화학식 3][Formula 3]

Figure 112019136166164-pat00004
Figure 112019136166164-pat00004

[화학식 4][Formula 4]

Figure 112019136166164-pat00005
Figure 112019136166164-pat00005

[화학식 5][Formula 5]

Figure 112019136166164-pat00006
Figure 112019136166164-pat00006

[화학식 6][Formula 6]

Figure 112019136166164-pat00007
Figure 112019136166164-pat00007

상기 에폭시기 또는 이소시아네이트기를 가지는 알콕시 실란화합물(B)은 하기 화학식 7 내지 10으로 표시되는 화합물 중에서 선택되는 1종 이상일 수 있다.The alkoxysilane compound (B) having an epoxy group or an isocyanate group may be at least one selected from compounds represented by the following Chemical Formulas 7 to 10.

[화학식 7][Formula 7]

Figure 112019136166164-pat00008
Figure 112019136166164-pat00008

[화학식 8][Formula 8]

Figure 112019136166164-pat00009
Figure 112019136166164-pat00009

[화학식 9][Formula 9]

Figure 112019136166164-pat00010
Figure 112019136166164-pat00010

[화학식 10][Formula 10]

Figure 112019136166164-pat00011
Figure 112019136166164-pat00011

상기 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물 전체 중량부에 대하여, 상기 친수성 유기관능기를 가지는 알콕시 실란화합물은 5 내지 50 중량부일 수 있다.Based on the total weight of the polydimethylsiloxane derivative compound capable of forming the hydrophilic surface, the amount of the alkoxysilane compound having the hydrophilic organic functional group may be 5 to 50 parts by weight.

한편, 상기 축합 반응시 경화 속도를 향상시키기 위하여, 본 발명은 테트라에틸오르토실리케이트(Tetraethyl orthosilicate; TEOS), 테트라메틸오르토실리케이트(Tetramethyl orthosilicate; TMOS), 메틸트리메톡시실란(Methyltrimethoxysilane; MTMS) 중에서 선택되는 1종 이상의 경화촉진제를 더 포함할 수 있다.On the other hand, in order to improve the curing rate during the condensation reaction, the present invention is tetraethyl orthosilicate (TEOS), tetramethyl orthosilicate (TMOS), methyltrimethoxysilane (Methyltrimethoxysilane; MTMS) selected from It may further include one or more curing accelerators.

상기 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물 전체 중량부에 대하여, 상기 경화촉진제는 5 내지 30 중량부일 수 있다.Based on the total weight of the polydimethylsiloxane derivative compound capable of forming the hydrophilic surface, the curing accelerator may be used in an amount of 5 to 30 parts by weight.

상기 히드록시기를 가지는 폴리디메틸실록산의 중량평균 분자량은 1,000 내지 10,000 g/mol일 수 있다.The weight average molecular weight of the polydimethylsiloxane having a hydroxyl group may be 1,000 to 10,000 g/mol.

상기 화학식 1 내지 4의 화합물의 중량평균 분자량은 300 ~ 5,000 g/mol일 수 있다.The weight average molecular weight of the compounds of Formulas 1 to 4 may be 300 to 5,000 g/mol.

한편, 본 발명은 상기 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물을 합성하기 위한 전구체로서, 상기 화학식 1 내지 6으로 표시되는 화합물 중에서 선택되는 1종 이상의 친수성 화합물(A)과 상기 화학식 7 내지 10으로 표시되는 화합물 중에서 선택되는 1종 이상의 알콕시 실란화합물(B)을 반응시켜 제조되는 친수성 유기관능기를 가지는 알콕시 실란화합물을 제공한다.On the other hand, the present invention is a precursor for synthesizing a polydimethylsiloxane derivative compound capable of forming a hydrophilic surface, comprising at least one hydrophilic compound (A) selected from compounds represented by Chemical Formulas 1 to 6 and Chemical Formulas 7 to 10. Provided is an alkoxysilane compound having a hydrophilic organic functional group prepared by reacting at least one alkoxysilane compound (B) selected from the compounds shown.

본 발명에 따른 PDMS 유도체 화합물은 친수성 유기관능기를 가지는 알콕시 실란화합물를 제조하고 이를 전구체로 이용하여 히드록시기를 가지는 PDMS와의 축합반응 공정을 통해 제조됨으로써, 경화시 우수한 친수성 표면 형성이 가능하다. 또한, 본 발명에 따른 PDMS 유도체 화합물은 종래 산소 플라즈마(O2 plasma) 처리, 코로나(Corona) 처리, UV 조사, 전기방전(Electrical discharge) 등에 비해 제조공정이 간단하여 제조공정 및 제조비용 면에서 큰 장점을 가진다.The PDMS derivative compound according to the present invention is prepared through a condensation reaction process with PDMS having a hydroxyl group by preparing an alkoxysilane compound having a hydrophilic organic functional group and using it as a precursor to form an excellent hydrophilic surface during curing. In addition, the PDMS derivative compound according to the present invention has a simple manufacturing process compared to conventional oxygen plasma (O 2 plasma) treatment, corona treatment, UV irradiation, electrical discharge, etc. have an advantage

도 1은 본 발명에 따라 제조된 친수성 표면 형성이 가능한 PDMS 유도체 화합물을 20cm × 20cm 크기의 폴리프로필렌 정사각형 용기에 주입하고 상온에서 4시간 경화시킨 후 60 oC 컨벡션 오븐에서 4 시간 건조하여서 제조된 경화물의 사진이다.
도 2는 본 발명의 실시예 29 내지 31에서 제조된 친수성 표면 형성이 가능한 PDMS 유도체 화합물(IMP 350-PDMS2000)의 경화 후 수분과의 접촉 시간 변화에 따른 물에 대한 접촉각 변화를 측정한 사진이다.
도 3은 본 발명의 실시예 32 내지 34에서 제조된 친수성 표면 형성이 가능한 PDMS 유도체 화합물(IMP 750-PDMS2000)의 경화 후 수분과의 접촉 시간 변화에 따른 물에 대한 접촉각 변화를 측정한 사진이다.
도 4는 본 발명의 실시예 35 내지 37에서 제조된 친수성 표면 형성이 가능한 PDMS 유도체 화합물(IMPMA 500-PDMS2000)의 경화 후 수분과의 접촉 시간 변화에 따른 물에 대한 접촉각 변화를 측정한 사진이다.1 shows a PDMS derivative compound capable of forming a hydrophilic surface prepared according to the present invention, injected into a polypropylene square container having a size of 20 cm × 20 cm, cured at room temperature for 4 hours, and then dried in a 60 o C convection oven for 4 hours. It is a picture of water.
2 is a photograph measuring the change in contact angle with water according to the change of contact time with water after curing of the PDMS derivative compound (IMP 350-PDMS2000) capable of forming a hydrophilic surface prepared in Examples 29 to 31 of the present invention.
3 is a photograph measuring the change in contact angle with water according to the change of contact time with moisture after curing of the PDMS derivative compound (IMP 750-PDMS2000) capable of forming a hydrophilic surface prepared in Examples 32 to 34 of the present invention.
4 is a photograph measuring the change in contact angle with water according to the change of contact time with water after curing of the PDMS derivative compound (IMPMA 500-PDMS2000) capable of forming a hydrophilic surface prepared in Examples 35 to 37 of the present invention.

본 발명은 먼저 '친수성 유기관능기를 가지는 알콕시 실란화합물'을 합성하고, 이를 소수성인 '히드록시기를 가지는 PDMS'(PDMS 유도체 화합물의 전구체)와 축합 반응을 수행함으로써, 복잡한 표면 처리 공정을 사용하지 않고서도 친수성 표면 형성이 가능한 PDMS 유도체 화합물을 제공하는 데 특징이 있다.The present invention first synthesizes an 'alkoxysilane compound having a hydrophilic organic functional group' and performs a condensation reaction with a hydrophobic 'PDMS having a hydroxyl group' (precursor of a PDMS derivative compound), without using a complicated surface treatment process. It is characterized by providing a PDMS derivative compound capable of forming a hydrophilic surface.

상기 '친수성 유기관능기를 가지는 알콕시 실란화합물'은 바람직하게는 '아민기 또는 히드록시기를 가지는 친수성 화합물(A)'과 '에폭시기 또는 이소시아네이트기를 가지는 알콕시 실란화합물(B)'을 반응시켜 제조될 수 있다.The 'alkoxy silane compound having a hydrophilic organic functional group' is preferably prepared by reacting 'a hydrophilic compound (A) having an amine group or a hydroxyl group' with an 'alkoxy silane compound having an epoxy group or an isocyanate group (B)'.

본 발명에 적용될 수 있는 친수성 화합물(A)는 친수성 유기관능기를 가지고 작용기(funtional group)로서 아민기 또는 히드록시기를 가지는 것이면 모두 포함될 수 있고, 실란화합물(B)는 알콕시와 작용기로서 '에폭시기'(글리시딜기) 또는 이소시아네이트기를 가지는 것이면 모두 포함될 수 있다.The hydrophilic compound (A) applicable to the present invention may be included as long as it has a hydrophilic organic functional group and has an amine group or a hydroxyl group as a functional group, and the silane compound (B) includes alkoxy and an 'epoxy group' (glycol) as a functional group. Cydyl group) or an isocyanate group may be included.

상기 친수성 화합물(A) 및 알콕시 실란화합물(B)의 대표적 물질을 하기 표 1에 나타내었으나 이에 제한되지는 않는다. 상기 아민기 또는 히드록시기를 가지는 친수성 화합물(A)에서 친수성 성분은 제한되지는 않으나 바람직하게는 폴리에틸렌글리콜일 수 있다.Representative materials of the hydrophilic compound (A) and the alkoxysilane compound (B) are shown in Table 1 below, but are not limited thereto. In the hydrophilic compound (A) having an amine group or a hydroxyl group, the hydrophilic component is not limited, but preferably polyethylene glycol.

구조식constitutional formula 화합물명compound name









AA

Figure 112019136166164-pat00012

중량평균 분자량: 300 ~ 5,000 g/mol
Figure 112019136166164-pat00012

Weight average molecular weight: 300 ~ 5,000 g/mol Hydroxyl PEG carboxylic acidHydroxyl PEG carboxylic acid
Figure 112019136166164-pat00013

중량평균 분자량: 300 ~ 5,000 g/mol
Figure 112019136166164-pat00013

Weight average molecular weight: 300 ~ 5,000 g/mol Hydroxyl PEG amineHydroxyl PEG amine
Figure 112019136166164-pat00014

중량평균 분자량: 300 ~ 5,000 g/mol
Figure 112019136166164-pat00014

Weight average molecular weight: 300 ~ 5,000 g/mol Poly(ethylene glycol) methyl etherPoly(ethylene glycol) methyl ether
Figure 112019136166164-pat00015

중량평균 분자량: 300 ~ 5,000 g/mol
Figure 112019136166164-pat00015

Weight average molecular weight: 300 ~ 5,000 g/mol Poly(ethylene glycol) methyl ether aminePoly(ethylene glycol) methyl ether amine
Figure 112019136166164-pat00016
Figure 112019136166164-pat00016
 2,2-Bis(hydroxymethyl)butyric acid2,2-Bis(hydroxymethyl)butyric acid
Figure 112019136166164-pat00017
Figure 112019136166164-pat00017
 2,2-Bis(hydroxymethyl)propionic acid2,2-Bis(hydroxymethyl)propionic acid










BB
Figure 112019136166164-pat00018
Figure 112019136166164-pat00018
 3-(Triethoxysilyl)propyl isocyanate 3-(Triethoxysilyl)propyl isocyanate
Figure 112019136166164-pat00019
Figure 112019136166164-pat00019
 3-(trimethoxysilyl)propyl isocyanate3-(trimethoxysilyl)propyl isocyanate
Figure 112019136166164-pat00020
Figure 112019136166164-pat00020
 3-Glycidyloxypropyl)triethoxysilane 3-Glycidyloxypropyl)triethoxysilane
Figure 112019136166164-pat00021
Figure 112019136166164-pat00021
 3-Glycidyloxypropyl)trimethoxysilane 3-Glycidyloxypropyl)trimethoxysilane

상기 '히드록시기를 가지는 PDMS'은 하기와 같이 실라놀 말단 PDMS일 수 있다.The 'PDMS having a hydroxyl group' may be a silanol-terminated PDMS as follows.

Figure 112019136166164-pat00022
Figure 112019136166164-pat00022

<실라놀 말단 PDMS><Silanol-terminated PDMS>

본 발명에서 친수성 표면 형성이 가능한 PDMS 유도체 화합물은 '친수성 유기관능기를 가지는 알콕시 실란화합물'과 '히드록시기를 가지는 PDMS'와 축합 반응시켜 제조된 화합물이며, 액체일 수 있으며, 시간 경과에 따른 경화된 'PDMS 경화물'(고체, 필름)을 포함한다. 본 발명에서 'PDMS 유도체 화합물'과 'PDMS 경화물'은 동일한 의미로 사용될 수 있다.In the present invention, the PDMS derivative compound capable of forming a hydrophilic surface is a compound prepared by condensation reaction with an 'alkoxysilane compound having a hydrophilic organic functional group' and 'PDMS having a hydroxyl group', and may be a liquid, and may be a 'cured' over time. PDMS cured product' (solid, film). In the present invention, 'PDMS derivative compound' and 'PDMS cured product' may be used as the same meaning.

친수성 hydrophilic 유기관능기를organic functional group 가지는 알콕시 branched alkoxy 실란화합물silane compound 합성 synthesis

본 발명의 친수성 표면 형성이 가능한 PDMS 유도체 화합물을 제조하기 위해 사용되는 친수성 유기관능기를 가지는 실란화합물의 합성은 제한되지는 않으나, 다음과 같은 공정을 통해 수행될 수 있다.The synthesis of a silane compound having a hydrophilic organic functional group used to prepare a PDMS derivative compound capable of forming a hydrophilic surface of the present invention is not limited, but may be performed through the following process.

질소 분위기 하에서, 아민 또는 히드록시기와 친수성 관능기를 동시에 가지는 화합물(A)과, 1개 이상의 에폭시기 또는 이소시아네이트기를 가지는 알콕시 실란화합물(B)를 바람직하게는 1:1 내지 1:2 사이의 반응 몰비로 상온에서 용매(톨루엔 등)에 용해한 후 4시간 동안 교반 반응시켜 합성한다.In a nitrogen atmosphere, the compound (A) having an amine or hydroxyl group and a hydrophilic functional group simultaneously and the alkoxysilane compound (B) having one or more epoxy or isocyanate groups are reacted in a molar ratio of preferably 1:1 to 1:2 at room temperature. It is synthesized by dissolving it in a solvent (toluene, etc.) in

이때, 화합물(A)의 아민기 또는 히드록시기는 실란화합물(B)의 에폭시기 또는 이소시아네이트기와 반응하여 결합하다.At this time, the amine group or the hydroxyl group of the compound (A) reacts and bonds with the epoxy group or the isocyanate group of the silane compound (B).

친수성 표면을 형성할 수 있는 PDMS 유도체 화합물의 제조Preparation of PDMS derivative compounds capable of forming hydrophilic surfaces

본 발명에 따른 친수성 표면을 형성할 수 있는 PDMS 유도체 화합물은 상기 합성된 친수성 유기관능기를 가지는 알콕시 실란화합물과 히드록시기를 함유한 PDMS를 상온 축합 반응을 통해서 제조되며, 제조된 PDMS 유도체 화합물(PDMS 경화물)은 수분과의 접촉시 PDMS 경화물 내에 존재하는 친수성 세그먼트와 소수성 세그먼트간의 미세 상분리를 통해서 강화된 친수성 표면을 형성한다.The PDMS derivative compound capable of forming a hydrophilic surface according to the present invention is prepared through a room temperature condensation reaction between the synthesized alkoxysilane compound having a hydrophilic organic functional group and PDMS containing a hydroxyl group, and the prepared PDMS derivative compound (PDMS cured product) ) forms a reinforced hydrophilic surface through fine phase separation between the hydrophilic segment and the hydrophobic segment present in the cured PDMS material upon contact with moisture.

본 발명에 따라 제조되는 친수성 표면 형성 PDMS 경화물의 물성은 사용되는 친수성 유기관능기를 가지는 알콕시 실란화합물 종류와 함량에 따라서 다양하게 조절이 가능하며, 용액을 제조하는 공정은 다음과 같다.The physical properties of the hydrophilic surface-forming PDMS cured product prepared according to the present invention can be variously adjusted according to the type and content of the alkoxysilane compound having a hydrophilic organic functional group used, and the process for preparing the solution is as follows.

히드록시기를 가지는 PDMS 전구체와 테트라히드로퓨란 또는 톨루엔과 1: 1 무게비로 상온에서 혼합한 용액을 본 발명의 친수성 유기 관능기를 가지는 알콕시 실란화합물과 다양한 무게비로 혼합하고 축합 반응시킨다.A solution obtained by mixing a PDMS precursor having a hydroxyl group and tetrahydrofuran or toluene in a 1: 1 weight ratio at room temperature is mixed with an alkoxysilane compound having a hydrophilic organic functional group of the present invention in various weight ratios and subjected to a condensation reaction.

이때, 축합 반응 경화 속도를 향상시키기 위하여 경화촉진제를 더 포함할 수 있다. 상기 경화촉진제는 테트라에틸오르토실리케이트(Tetraethyl orthosilicate; TEOS), 테트라메틸오르토실리케이트(Tetramethyl orthosilicate; TMOS), 메틸트리메톡시실란(Methyltrimethoxysilane; MTMS) 등이 이용될 수 있다. 경화촉진제를 첨가 혼합하고 일정한 크기를 가지는 용기에 주입하고 상온에서 축합 반응을 통해서 PDMS 유도체 화합물(PDMS 경화물)가 제조된다. PDMS 경화물에서 친수성 유기관능기를 가지는 알콕시 실란화합물은 제한되지는 않으나 5 내지 50 중량부이고, 히드록시기를 가지는 PDMS는 95 내지 50 중량부인 것이 바람직하다. 용매는 제한되지는 않으나 30 내지 50 중량부로 이루어질 수 있다. 또한, 상기 축합 반응시 경화 속도를 향상시키기 위하여 경화촉진제는 제한되지는 않으나 5 내지 30 중량부가 첨가될 수 있다.In this case, a curing accelerator may be further included in order to improve the condensation reaction curing rate. The curing accelerator may include tetraethyl orthosilicate (TEOS), tetramethyl orthosilicate (TMOS), methyltrimethoxysilane (MTMS), and the like. A PDMS derivative compound (PDMS cured product) is prepared by adding and mixing a curing accelerator, injecting it into a container having a certain size, and performing a condensation reaction at room temperature. The amount of the alkoxysilane compound having a hydrophilic organic functional group in the cured PDMS is not limited, but is preferably 5 to 50 parts by weight, and 95 to 50 parts by weight of PDMS having a hydroxyl group. The solvent is not limited, but may consist of 30 to 50 parts by weight. In addition, in order to improve the curing rate during the condensation reaction, the curing accelerator is not limited, but 5 to 30 parts by weight may be added.

상기 히드록시기를 가지는 PDMS의 중량평균 분자량은 제한되지는 않으나 1,000 내지 10,000 g/mol일 수 있다.The weight average molecular weight of the PDMS having the hydroxyl group is not limited, but may be 1,000 to 10,000 g/mol.

이하 실시예를 통하여 본 발명을 상세히 설명한다. 이하 실시예는 본 발명의 바람직한 일 실시예일 뿐, 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. The following examples are only preferred examples of the present invention, and the scope of the present invention is not limited to the following examples.

친수성 유기관능기를 가지는 실란화합물 합성Synthesis of silane compounds having hydrophilic organic functional groups

실시예 1 내지 20Examples 1 to 20

질소 분위기 하에서, 상기 표 1의 아민기 또는 히드록시를 가지는 친수성 화합물(A)과 이소시아네이트를 가지고 있는 실란화합물(B) 중에서 선택된 화합물을 1:1 내지 1:2 사이의 반응 몰비로 하여 70℃에서 4시간 동안 교반 반응시켜 신규한 친수성 유기관능기를 가지는 알콕시 실란화합물을 합성하였다. 상세한 조성은 하기 표 2에 나타내었다.In a nitrogen atmosphere, a compound selected from the hydrophilic compound (A) having an amine group or hydroxyl of Table 1 and the silane compound (B) having an isocyanate in a reaction molar ratio of 1:1 to 1:2 at 70° C. The reaction was stirred for 4 hours to synthesize a novel alkoxysilane compound having a hydrophilic organic functional group. The detailed composition is shown in Table 2 below.

실시예Example 화합물명compound name 반응 몰비
(물질 A:B)Reaction molar ratio
(Substance A:B) 분자량 (g/mol)Molecular Weight (g/mol) 성상appearance 실시예 1Example 1 IHPIHP 1:11:1 3247.363247.36 투명한 액상clear liquid 실시예 2Example 2 IHPAIHPA 1:11:1 3247.363247.36 투명한 액상clear liquid 실시예 3Example 3 IMP 350IMP 350 1:11:1 597.36597.36 투명한 액상clear liquid 실시예 4Example 4 IMP 550IMP 550 1:11:1 797.36797.36 투명한 액상clear liquid 실시예 5Example 5 IMP 750IMP 750 1:11:1 997.36997.36 투명한 액상clear liquid 실시예 6Example 6 IPMA 500IPMA 500 1:11:1 747.36747.36 투명한 액상clear liquid 실시예 7Example 7 IPMA 700IPMA 700 1:11:1 947.36947.36 투명한 액상clear liquid 실시예 8Example 8 IPMA 1000IPMA 1000 1:11:1 1274.361274.36 투명한 액상clear liquid 실시예 9Example 9 IBAIBA 1:21:2 543.68543.68 투명한 액상clear liquid 실시예 10Example 10 IPAIPA 1:21:2 515.62515.62 투명한 액상clear liquid 실시예 11Example 11 IMHPIMHP 1:11:1 3205.293205.29 투명한 액상clear liquid 실시예 12Example 12 IMHPAIMHPA 1:11:1 3205.293205.29 투명한 액상clear liquid 실시예 13Example 13 IMMP 350IMMP 350 1:11:1 555.29555.29 투명한 액상clear liquid 실시예 14Example 14 IMMP 550IMMP 550 1:11:1 755.29755.29 투명한 액상clear liquid 실시예 15Example 15 IMMP 750IMMP 750 1:11:1 955.29955.29 투명한 액상clear liquid 실시예 16Example 16 IMPMA 500IMPMA 500 1:11:1 705.29705.29 투명한 액상clear liquid 실시예 17Example 17 IMPMA 700IMPMA 700 1:11:1 905.29905.29 투명한 액상clear liquid 실시예 18Example 18 IMPMA 1000IMPMA 1000 1:11:1 1205.291205.29 투명한 액상clear liquid 실시예 19Example 19 IBAIBA 1:21:2 501.61501.61 투명한 액상clear liquid 실시예 20Example 20 IPAIPA 1:21:2 473.55473.55 투명한 액상clear liquid

상기 실시예 1 내지 20의 친수성 화합물(A)과 실란화합물(B)의 구성은 다음과 같다. The compositions of the hydrophilic compound (A) and the silane compound (B) of Examples 1 to 20 are as follows.

실시예 1: 3-(Triethoxysilyl)propyl isocyanate와 Hydroxyl PEG carboxylic acid (분자량 3000 g/mol)과의 반응물Example 1: Reaction product of 3-(Triethoxysilyl)propyl isocyanate and Hydroxyl PEG carboxylic acid (molecular weight 3000 g/mol)

실시예 2: 3-(Triethoxysilyl)propyl isocyanate와 Hydroxyl PEG amine (분자량 3000 g/mol)과의 반응물Example 2: Reaction product of 3-(Triethoxysilyl)propyl isocyanate and Hydroxyl PEG amine (molecular weight 3000 g/mol)

실시예 3: 3-(Triethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether (분자량 350 g/mol)와의 반응물Example 3: Reaction product of 3-(Triethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether (molecular weight 350 g/mol)

실시예 4: 3-(Triethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether (분자량 550 g/mol)와의 반응물Example 4: Reaction product of 3-(Triethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether (molecular weight 550 g/mol)

실시예 5: 3-(Triethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether (분자량 750 g/mol)와의 반응물Example 5: Reaction product of 3-(Triethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether (molecular weight 750 g/mol)

실시예 6: 3-(Triethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether amine (분자량 500 g/mol)과의 반응물Example 6: Reaction product of 3-(Triethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether amine (molecular weight 500 g/mol)

실시예 7: 3-(Triethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether amine (분자량 700 g/mol)과의 반응물Example 7: Reaction product of 3-(Triethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether amine (molecular weight 700 g/mol)

실시예 8: 3-(Triethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether amine (분자량 1000 g/mol)과의 반응물Example 8: Reaction product of 3-(Triethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether amine (molecular weight 1000 g/mol)

실시예 9: 3-(Triethoxysilyl)propyl isocyanate와 2,2-Bis(hydroxymethyl)butyric acid와의 반응물Example 9: Reaction product of 3-(Triethoxysilyl)propyl isocyanate and 2,2-Bis(hydroxymethyl)butyric acid

실시예 10: 3-(Triethoxysilyl)propyl isocyanate와 2,2-Bis(hydroxymethyl)propionic acid와의 반응물Example 10: Reaction of 3-(Triethoxysilyl)propyl isocyanate and 2,2-Bis(hydroxymethyl)propionic acid

실시예 11: 3-(Trimethoxysilyl)propyl isocyanate와 Hydroxyl PEG carboxylic acid (분자량 3000 g/mol)과의 반응물Example 11: Reaction of 3-(Trimethoxysilyl)propyl isocyanate and Hydroxyl PEG carboxylic acid (molecular weight 3000 g/mol)

실시예 12: 3-(Trimethoxysilyl)propyl isocyanate와 Hydroxyl PEG amine (분자량 3000 g/mol)과의 반응물Example 12: Reaction product of 3-(Trimethoxysilyl)propyl isocyanate and Hydroxyl PEG amine (molecular weight 3000 g/mol)

실시예 13: 3-(Trimethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether (분자량 350 g/mol)와의 반응물Example 13: Reaction product of 3-(Trimethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether (molecular weight 350 g/mol)

실시예 14: 3-(Trimethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether (분자량 550 g/mol)와의 반응물Example 14: Reaction product of 3-(Trimethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether (molecular weight 550 g/mol)

실시예 15: 3-(Trimethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether (분자량 750 g/mol)와의 반응물Example 15: Reaction product of 3-(Trimethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether (molecular weight 750 g/mol)

실시예 16: 3-(Trimethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether amine (분자량 500 g/mol)과의 반응물Example 16: Reaction product of 3-(Trimethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether amine (molecular weight 500 g/mol)

실시예 17: 3-(Trimethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether amine (분자량 700 g/mol)과의 반응물Example 17: Reaction product of 3-(Trimethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether amine (molecular weight 700 g/mol)

실시예 18: 3-(Trimethoxysilyl)propyl isocyanate와 Poly(ethylene glycol) methyl ether amine (분자량 1000 g/mol)과의 반응물Example 18: Reaction product of 3-(Trimethoxysilyl)propyl isocyanate and Poly(ethylene glycol) methyl ether amine (molecular weight 1000 g/mol)

실시예 19: 3-(Trimethoxysilyl)propyl isocyanate와 2,2-Bis(hydroxymethyl)butyric acid와의 반응물Example 19: Reaction of 3-(Trimethoxysilyl)propyl isocyanate and 2,2-Bis(hydroxymethyl)butyric acid

실시예 20: 3-(Trimethoxysilyl)propyl isocyanate와 2,2-Bis(hydroxymethyl)propionic acid와의 반응물Example 20: Reaction of 3-(Trimethoxysilyl)propyl isocyanate and 2,2-Bis(hydroxymethyl)propionic acid

실시예 21 내지 28Examples 21 to 28

질소 분위기 하에서, 상기 표 1의 아민기 또는 히드록시를 가지는 친수성 화합물(A)과 에폭시기를 가지고 있는 실란화합물(B) 중에서 선택된 화합물을 1:1 내지 1:2 사이의 반응 몰비로 하여 70 ~ 80 ℃에서 6시간 동안 교반 반응시켜 신규한 친수성 유기관능기를 가지는 알콕시 실란화합물을 합성하였다. 상세한 조성은 하기 표 3에 나타내었다.In a nitrogen atmosphere, the compound selected from the hydrophilic compound (A) having an amine group or hydroxyl of Table 1 and the silane compound (B) having an epoxy group in a reaction molar ratio of 1:1 to 1:2 is 70 to 80 A novel alkoxysilane compound having a hydrophilic organic functional group was synthesized by stirring at ℃ for 6 hours. The detailed composition is shown in Table 3 below.

실시예Example 화합물명compound name 반응 몰비
(물질 A:B)Reaction molar ratio
(Substance A:B) 분자량 (g/mol)Molecular Weight (g/mol) 성상appearance 실시예 21Example 21 GMHPAGMHPA 1:21:2 3472.683472.68 투명한 액상clear liquid 실시예 22Example 22 GMPMA 500GMPMA 500 1:21:2 972.68972.68 투명한 액상clear liquid 실시예 23Example 23 GMPMA 700GMPMA 700 1:21:2 1172.681172.68 투명한 액상clear liquid 실시예 24Example 24 GMPMA 1000GMPMA 1000 1:21:2 1472.681472.68 투명한 액상clear liquid 실시예 25Example 25 GEHPAGEHPA 1:21:2 3268.263268.26 투명한 액상clear liquid 실시예 26Example 26 GEPMA 500GEPMA 500 1:21:2 768.26768.26 투명한 액상clear liquid 실시예 27 Example 27 GEPMA 700GEPMA 700 1:21:2 968.26968.26 투명한 액상clear liquid 실시예 28Example 28 GEPMA 1000GEPMA 1000 1:21:2 1268.261268.26 투명한 액상clear liquid

상기 실시예 21 내지 28의 친수성 화합물(A)과 실란화합물(B)의 구성은 다음과 같다. The compositions of the hydrophilic compound (A) and the silane compound (B) of Examples 21 to 28 are as follows.

실시예 21: 3-Glycidyloxypropyl)trimethoxysilane과 Hydroxyl PEG amine (분자량 3000 g/mol)과의 반응물Example 21: Reaction product of 3-Glycidyloxypropyl)trimethoxysilane and Hydroxyl PEG amine (molecular weight 3000 g/mol)

실시예 22: 3-Glycidyloxypropyl)trimethoxysilane와 Poly(ethylene glycol) methyl ether amine (분자량 500 g/mol)과의 반응물Example 22: Reaction product of 3-Glycidyloxypropyl)trimethoxysilane and Poly(ethylene glycol) methyl ether amine (molecular weight 500 g/mol)

실시예 23: 3-Glycidyloxypropyl)trimethoxysilane와 Poly(ethylene glycol) methyl ether amine (분자량 700 g/mol)과의 반응물Example 23: Reaction product of 3-Glycidyloxypropyl)trimethoxysilane and Poly(ethylene glycol) methyl ether amine (molecular weight 700 g/mol)

실시예 24: 3-Glycidyloxypropyl)trimethoxysilane와 Poly(ethylene glycol) methyl ether amine (분자량 1000 g/mol)과의 반응물Example 24: Reaction product of 3-Glycidyloxypropyl)trimethoxysilane and Poly(ethylene glycol) methyl ether amine (molecular weight 1000 g/mol)

실시예 25: 3-Glycidyloxypropyl)triethoxysilane과 Hydroxyl PEG amine (분자량 3000 g/mol)과의 반응물Example 25: Reaction product of 3-Glycidyloxypropyl)triethoxysilane and Hydroxyl PEG amine (molecular weight 3000 g/mol)

실시예 26: 3-Glycidyloxypropyl)triethoxysilane와 Poly(ethylene glycol) methyl ether amine (분자량 500 g/mol)과의 반응물Example 26: Reaction product of 3-Glycidyloxypropyl)triethoxysilane and Poly(ethylene glycol) methyl ether amine (molecular weight 500 g/mol)

실시예 27: 3-Glycidyloxypropyl)triethoxysilane와 Poly(ethylene glycol) methyl ether amine (분자량 700 g/mol)과의 반응물Example 27: Reaction product of 3-Glycidyloxypropyl)triethoxysilane and Poly(ethylene glycol) methyl ether amine (molecular weight 700 g/mol)

실시예 28: 3-Glycidyloxypropyl)triethoxysilane와 Poly(ethylene glycol) methyl ether amine (분자량 1000 g/mol)과의 반응물Example 28: Reaction product of 3-Glycidyloxypropyl)triethoxysilane and Poly(ethylene glycol) methyl ether amine (molecular weight 1000 g/mol)

친수성 표면 hydrophilic surface 형성가능한formable PDMS 유도체 화합물의 제조 Preparation of PDMS derivative compounds

실시예 29 내지 40Examples 29-40

히드록시기를 가지는 PDMS 전구체(분자량 2,000 g/mol)와 테트라히드로퓨란 또는 톨루엔과 1: 1 무게비로 상온에서 혼합한 용액을 상기 제조한 친수성 유기관능기를 가지는 알콕시 실란화합물과 다양한 무게비로 혼합하고 축합 반응 경화 속도를 향상시키기 위하여 테트라에틸오르토실리케이트(Tetraethyl orthosilicate; TEOS)를 첨가 혼합하고 일정한 크기를 가지는 용기에 주입하고 상온에서 축합 반응시켜 PDMS 유도체 화합물을 제조하였다. 이때 축합 반응 촉매인 디부틸 틴디라우레이트 Dibutyl tin dilaurate를 1 중량부를 첨가하였다. 상세한 조성은 하기 표 4에 나타내었다.A solution of a PDMS precursor having a hydroxyl group (molecular weight 2,000 g/mol) and tetrahydrofuran or toluene in a 1:1 weight ratio at room temperature is mixed with the alkoxysilane compound having a hydrophilic organic functional group prepared above in various weight ratios, followed by condensation reaction curing In order to improve the speed, tetraethyl orthosilicate (TEOS) was added and mixed, injected into a container having a certain size, and subjected to condensation reaction at room temperature to prepare a PDMS derivative compound. At this time, 1 part by weight of dibutyl tin dilaurate, which is a condensation reaction catalyst, was added. The detailed composition is shown in Table 4 below.

실시예Example 화합물명compound name HO-PDMS HO-PDMS 친수성 유기 관능기 함유 알콕시 실란화합물Alkoxy silane compound containing hydrophilic organic functional group 실란화합물silane compound 실시예 29Example 29 IMP 350-PDMS2000(1)IMP 350-PDMS2000(1) 10g10g 실시예 3Example 3 IMP 350 2.1gIMP 350 2.1g TEOS 4gTEOS 4g 실시예 30Example 30 IMP 350-PDMS2000(2)IMP 350-PDMS2000(2) 10g10g 실시예 3Example 3 IMP 350 4.2gIMP 350 4.2g TEOS 4gTEOS 4g 실시예 31Example 31 IMP 350-PDMS2000(3)IMP 350-PDMS2000(3) 10g10g 실시예 3Example 3 IMP 350 7.0gIMP 350 7.0g TEOS 4gTEOS 4g 실시예 32Example 32 IMP 750-PDMS2000(1)IMP 750-PDMS2000(1) 10g10g 실시예 5Example 5 IMP 750 2.1gIMP 750 2.1g TEOS 4gTEOS 4g 실시예 33Example 33 IMP 750-PDMS2000(2)IMP 750-PDMS2000(2) 10g10g 실시예 5Example 5 IMP 750 4.2gIMP 750 4.2g TEOS 4gTEOS 4g 실시예 34Example 34 IMP 750-PDMS2000(3)IMP 750-PDMS2000(3) 10g10g 실시예 5Example 5 IMP 750 7.0gIMP 750 7.0g TEOS 4gTEOS 4g 실시예 35Example 35 IMPMA 500-PDMS2000(1)IMPMA 500-PDMS2000(1) 10g10g 실시예 16Example 16 IMPMA 500 2.1gIMPMA 500 2.1g TEOS 4gTEOS 4g 실시예 36Example 36 IMPMA 500-PDMS2000(2)IMPMA 500-PDMS2000(2) 10g10g 실시예 16Example 16 IMPMA 500 4.2gIMPMA 500 4.2g TEOS 4gTEOS 4g 실시예 37Example 37 IMPMA 500-PDMS2000(3)IMPMA 500-PDMS2000(3) 10g10g 실시예 16Example 16 IMPMA 500 7.0gIMPMA 500 7.0g TEOS 4gTEOS 4g 실시예 38Example 38 GMPMA 700-PDMS2000(1)GMPMA 700-PDMS2000(1) 10g10g 실시예 23Example 23 GMPMA 700 1.0gGMPMA 700 1.0g TEOS 4gTEOS 4g 실시예 39Example 39 GMPMA 700-PDMS2000(2)GMPMA 700-PDMS2000(2) 10g10g 실시예 23Example 23 GMPMA 700 2.0gGMPMA 700 2.0g TEOS 4gTEOS 4g 실시예 40Example 40 GMPMA 700-PDMS2000(3)GMPMA 700-PDMS2000(3) 10g10g 실시예 23Example 23 GMPMA 700 3.0gGMPMA 700 3.0g TEOS 4gTEOS 4g

도 1은 본 발명에 따라 제조된 친수성 표면 형성이 가능한 PDMS 유도체 화합물을 20cm × 20cm 크기의 폴리프로필렌 정사각형 용기에 주입하고 상온에서 4시간 경화시킨 후 60 oC 컨벡션 오븐에서 4 시간 건조하여서 제조된 경화물의 사진이다.1 shows a PDMS derivative compound capable of forming a hydrophilic surface prepared according to the present invention, injected into a polypropylene square container having a size of 20 cm × 20 cm, cured at room temperature for 4 hours, and then dried in a 60 o C convection oven for 4 hours. It is a picture of water.

실험예Experimental example 1: 친수성 1: hydrophilic 유기관능기를organic functional group 가지는 eggplant 알콕시실란alkoxysilane 화합물 종류 및 함량에 따른 물에 대한 For water according to compound type and content 접촉각contact angle 변화 change

실시예 29 내지 40에서 제조된 PDMS 경화물의 표면의 친수성 형성을 확인하기 위해서 표 4에 기술한 방법으로 PDMS 경화물 표면에 물방울을 형성시키고 시간에 따른 접촉각 변화를 하기 표 5의 평가 방법을 통해 측정하고, 그 측정 결과를 도 2 내지 4 및 표 6에 나타내었다.In order to confirm the formation of hydrophilicity on the surface of the cured PDMS material prepared in Examples 29 to 40, water droplets were formed on the surface of the cured PDMS material by the method described in Table 4, and the change in contact angle with time was measured through the evaluation method in Table 5 below. and the measurement results are shown in FIGS. 2 to 4 and Table 6.

평가대상Evaluation target 평가 방법Assessment Methods 접촉각contact angle Double Distilled Deionized Water를 시료 시편에 적하하여서 표면에 형성된 물방울의 접촉각을 측정.
시험 규격: ASTM D5946에 준함.Measure the contact angle of water droplets formed on the surface by dropping Double Distilled Deionized Water onto the sample specimen.
Test Specification: According to ASTM D5946.

도 2는 본 발명의 실시예 29 내지 31에서 제조된 친수성 표면 형성이 가능한 PDMS 유도체 화합물(IMP 350-PDMS2000)의 경화 후 수분과의 접촉 시간 변화에 따른 물에 대한 접촉각 변화를 측정한 사진이다.2 is a photograph measuring the change in contact angle with water according to the change of contact time with water after curing of the PDMS derivative compound (IMP 350-PDMS2000) capable of forming a hydrophilic surface prepared in Examples 29 to 31 of the present invention.

도 3은 본 발명의 실시예 32 내지 34에서 제조된 친수성 표면 형성이 가능한 PDMS 유도체 화합물(IMP 750-PDMS2000)의 경화 후 수분과의 접촉 시간 변화에 따른 물에 대한 접촉각 변화를 측정한 사진이다.3 is a photograph measuring the change in contact angle with water according to the change of contact time with moisture after curing of the PDMS derivative compound (IMP 750-PDMS2000) capable of forming a hydrophilic surface prepared in Examples 32 to 34 of the present invention.

도 4는 본 발명의 실시예 35 내지 37에서 제조된 친수성 표면 형성이 가능한 PDMS 유도체 화합물(IMPMA 500-PDMS2000)의 경화 후 수분과의 접촉 시간 변화에 따른 물에 대한 접촉각 변화를 측정한 사진이다.4 is a photograph measuring the change in contact angle with water according to the change of contact time with water after curing of the PDMS derivative compound (IMPMA 500-PDMS2000) capable of forming a hydrophilic surface prepared in Examples 35 to 37 of the present invention.

실시예Example 화합물명compound name 물방울 형성
직후 접촉각 water droplet formation
contact angle immediately after 물방물 형성
1시간후 접촉각 water droplet formation
contact angle after 1 hour 물방물 형성
2시간후 접촉각 water droplet formation
contact angle after 2 hours 실시예 29Example 29 IMP 350-PDMS2000(1)IMP 350-PDMS2000(1) 103.65o 103.65 o 80.51o 80.51 o 69.76o 69.76 o 실시예 30Example 30 IMP 350-PDMS2000(2)IMP 350-PDMS2000(2) 108.15o 108.15 o 69.36o 69.36 o 60.68o 60.68 o 실시예 31Example 31 IMP 350-PDMS2000(3)IMP 350-PDMS2000(3) 102.81o 102.81 o 75.07o 75.07 o 69.36o 69.36 o 실시예 32Example 32 IMP 750-PDMS2000(1)IMP 750-PDMS2000(1) 106.67o 106.67 o 61.28o 61.28 o 47.41o 47.41 o 실시예 33Example 33 IMP 750-PDMS2000(2)IMP 750-PDMS2000(2) 99.17o 99.17 o 51.51o 51.51 o 45.57o 45.57 o 실시예 34Example 34 IMP 750-PDMS2000(3)IMP 750-PDMS2000(3) 104.28o 104.28 o 63.65o 63.65 o 41.58o 41.58 o 실시예 35Example 35 IMPMA 500-PDMS2000(1)IMPMA 500-PDMS2000(1) 93.81o 93.81 o 52.22o 52.22 o 44.59o 44.59 o 실시예 36Example 36 IMPMA 500-PDMS2000(2)IMPMA 500-PDMS2000(2) 108.49o 108.49 o 67.79o 67.79 o 54.56o 54.56 o 실시예 37Example 37 IMPMA 500-PDMS2000(3)IMPMA 500-PDMS2000(3) 97.60o 97.60 o 71.85o 71.85 o 61.48o 61.48 o 실시예 38Example 38 GMPMA 700-PDMS2000(1)GMPMA 700-PDMS2000(1) 101.20o 101.20 o 60.18o 60.18 o 46.41o 46.41 o 실시예 39Example 39 GMPMA 700-PDMS2000(1)GMPMA 700-PDMS2000(1) 98.84o 98.84 o 52.34o 52.34 o 42.34o 42.34 o 실시예 40Example 40 GMPMA 700-PDMS2000(1)GMPMA 700-PDMS2000(1) 94.92o 94.92 o 58.65o 58.65 o 40.23o 40.23 o

상기 표 6 및 도 2 내지 4에 보이는 바와 같이, 물방울 형성 직후 접촉각은 95o이상으로 접촉각이 높아 강한 소수성을 나타내었으나, 물방울 형성 2시간후 접촉각은 40o 내지 60o 정도로 현저히 낮아져 친수성이 유의적으로 개선된 것을 확인할 수 있다. As shown in Table 6 and FIGS . 2 to 4, the contact angle immediately after the formation of the water droplet was 95 o or more, indicating strong hydrophobicity. improvement can be seen.

[참고문헌][references]

1. N.E Stankova, P.A Atanasov, Ru.G. Nikov, R.G. Nikov, et al., Appl. Surf. Sci., 374 , 96-103 (2016).1. NE Stankova, PA Atanasov, Ru. G. Nikov, R. G. Nikov, et al., Appl. Surf. Sci., 374 , 96-103 (2016).

2. Y. H. Kim, M. G. Jeong, H. O. Seo, et al. Appl. Surf. Sci., 258 , 7562-7566 (2012).2. YH Kim, MG Jeong, HO Seo, et al. Appl. Surf. Sci., 258 , 7562-7566 (2012).

3. J. M K. Ng, I. Gitlin, A. D. Stroock, G. M. Whitesides, Electrophoresis, 23 , 3461-3473 (2002).3. J. M K. Ng, I. Gitlin, AD Stroock, GM Whitesides, Electrophoresis, 23 , 3461-3473 (2002).

4. E. P. Kartalob, W. F. Anderson, A. Schere, Journal of Nanoscience and Nanotechnology, 6 , 2265-2277 (2006).4. EP Kartalob, WF Anderson, A. Schere, Journal of Nanoscience and Nanotechnology, 6 , 2265-2277 (2006).

5. D.M. Smith, R. G. Lehmann, R. Narayan, G.E Kozerski, Compost Science & Untilization, 6 , 6-12 (1998).5. DM Smith, RG Lehmann, R. Narayan, GE Kozerski, Compost Science & Untilization, 6 , 6-12 (1998).

6. Li K, Zeng X, Li H, Colloids Surf., A : Physic. Eng. Asp., 445 , 111-118 (2014).6. Li K, Zeng X, Li H, Colloids Surf., A: Physic. Eng. Asp., 445 , 111-118 (2014).

7. Z. Yuan, J. Bin, X. Wang, Surf. Coat. Technol., 254 , 97-103(2014).7. Z. Yuan, J. Bin, X. Wang, Surf. Coat. Technol., 254 , 97-103 (2014).

8. S. Pinto, P. Alves, C.M. Matos, Colloid Surf. B: Biointerf., 81 , 20-26(2010).8. S. Pinto, P. Alves, CM Matos, Colloid Surf. B: Biointerf., 81 , 20-26 (2010).

9. S. H. Tan, N. Nguyen, Y. C. Chua, Biomicrofluidics, 4 , 032204-1-032204-8 (2010).9. SH Tan, N. Nguyen, YC Chua, Biomicrofluidics, 4 , 032204-1-032204-8 (2010).

10. Z. Almutairi, C. L. Ren, L. Simon, Colloids Surf., A : Physic. Eng. Asp., 415 , 406-412(2012).10. Z. Almutairi, CL Ren, L. Simon, Colloids Surf., A: Physic. Eng. Asp., 415 , 406-412 (2012).

11. S. Wu. Surface and interfacial tensions of polymers, oligomers, plasticizers, and organic pigments, Polymer handbook (Eds J. Brandup, E. H. Immergut, E. A Grulke, A. Abe, D. R. Bloch, Wiley, New York), 1989.11. S. Wu. Surface and interfacial tensions of polymers, oligomers, plasticizers, and organic pigments, Polymer handbook (Eds J. Brandup, E. H. Immergut, E. A Grulke, A. Abe, D. R. Bloch, Wiley, New York), 1989.

12. B. Schnyder, T. Lippert, R. Kotz, A. Wokaun, V.M Graubner, O.Nuyken, Surf. Sci., 1067 , 532-535 (2003). 12. B. Schnyder, T. Lippert, R. Kotz, A. Wokaun, VM Graubner, O. Nuyken, Surf. Sci., 1067 , 532-535 (2003).

13. J. Kim, M.K Chaudhury, M.J Owen, J. Colloid Interface Sci., 226 , 231-236 (2000).13. J. Kim, MK Chaudhury, MJ Owen, J. Colloid Interface Sci., 226 , 231-236 (2000).

14. K. Kim, S. W Park, S.S. Yang, BioChip Journal, 4 , 148-154 (2010).14. K. Kim, S. W Park, SS Yang, BioChip Journal, 4 , 148-154 (2010).

15. C. W. Beh, W. Zhou, T. Wang, Lab Ship, 12 , 4120-4127(2012).15. CW Beh, W. Zhou, T. Wang, Lab Ship, 12 , 4120-4127 (2012).

16. C. Cheng, K.T. Powell, E. Koshdel, K. L. Wooley, Macromol., 40 , 7195-7207 (2007).16. C. Cheng, KT Powell, E. Koshdel, KL Wooley, Macromol., 40 , 7195-7207 (2007).

Claims (11)

삭제delete 하기 화학식 1 내지 6으로 표시되는 화합물 중에서 선택되는 아민기 또는 히드록시기를 가지는 친수성 화합물(A)을 에폭시기 또는 이소시아네이트기를 가지는 알콕시 실란화합물(B)을 반응시켜 친수성 유기관능기를 가지는 알콕시 실란화합물을 제조하고,
상기 알콕시 실란화합물과 히드록시기를 가지는 폴리디메틸실록산(PDMS)을 축합 반응시켜 제조됨으로써,
친수성 표면이 형성되어 유기물질 또는 금속 물질과 부착 또는 접착될 수 있는 것을 특징으로 하는, 폴리디메틸실록산 유도체 화합물.
[화학식 1]
Figure 112021065758143-pat00047

(중량평균 분자량: 300 ~ 5,000 g/mol)
[화학식 2]
Figure 112021065758143-pat00048

(중량평균 분자량: 300 ~ 5,000 g/mol)
[화학식 3]
Figure 112021065758143-pat00049

(중량평균 분자량: 300 ~ 5,000 g/mol)
[화학식 4]
Figure 112021065758143-pat00050

(중량평균 분자량: 300 ~ 5,000 g/mol)
[화학식 5]
Figure 112021065758143-pat00051

[화학식 6]
Figure 112021065758143-pat00052

To prepare an alkoxysilane compound having a hydrophilic organic functional group by reacting a hydrophilic compound (A) having an amine group or a hydroxyl group selected from the compounds represented by the following formulas 1 to 6 with an alkoxysilane compound (B) having an epoxy group or an isocyanate group,
By condensing the alkoxysilane compound and polydimethylsiloxane (PDMS) having a hydroxyl group,
A polydimethylsiloxane derivative compound, characterized in that a hydrophilic surface is formed so that it can adhere or adhere to an organic material or a metallic material.
[Formula 1]
Figure 112021065758143-pat00047

(weight average molecular weight: 300 ~ 5,000 g/mol)
[Formula 2]
Figure 112021065758143-pat00048

(weight average molecular weight: 300 ~ 5,000 g/mol)
[Formula 3]
Figure 112021065758143-pat00049

(weight average molecular weight: 300 ~ 5,000 g/mol)
[Formula 4]
Figure 112021065758143-pat00050

(weight average molecular weight: 300 ~ 5,000 g/mol)
[Formula 5]
Figure 112021065758143-pat00051

[Formula 6]
Figure 112021065758143-pat00052

 삭제delete 삭제delete 제2항에 있어서,
상기 에폭시기 또는 이소시아네이트기를 가지는 알콕시 실란화합물(B)은 하기 화학식 7 내지 10으로 표시되는 화합물 중에서 선택되는 1종 이상인 것을 특징으로 하는, 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물.
[화학식 7]
Figure 112019136166164-pat00029

[화학식 8]
Figure 112019136166164-pat00030

[화학식 9]
Figure 112019136166164-pat00031

[화학식 10]
Figure 112019136166164-pat00032

3. The method of claim 2,
The alkoxysilane compound (B) having an epoxy group or an isocyanate group is a polydimethylsiloxane derivative compound capable of forming a hydrophilic surface, characterized in that at least one selected from compounds represented by the following Chemical Formulas 7 to 10.
[Formula 7]
Figure 112019136166164-pat00029

[Formula 8]
Figure 112019136166164-pat00030

[Formula 9]
Figure 112019136166164-pat00031

[Formula 10]
Figure 112019136166164-pat00032

 제2항에 있어서,
상기 친수성 유기관능기를 가지는 알콕시 실란화합물은 5 내지 50 중량부이고, 히드록시기를 가지는 폴리디메틸실록산은 50 내지 95 중량부인 것을 특징으로 하는, 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물.
3. The method of claim 2,
The polydimethylsiloxane derivative compound capable of forming a hydrophilic surface, characterized in that the amount of the alkoxysilane compound having a hydrophilic organic functional group is 5 to 50 parts by weight, and the polydimethylsiloxane having a hydroxyl group is 50 to 95 parts by weight.
 제2항에 있어서,
상기 친수성 유기관능기를 가지는 알콕시 실란화합물과 히드록시기를 가지는 폴리디메틸실록산(PDMS)의 축합 반응시 경화 속도를 향상시키기 위하여,
테트라에틸오르토실리케이트(Tetraethyl orthosilicate; TEOS), 테트라메틸오르토실리케이트(Tetramethyl orthosilicate; TMOS), 메틸트리메톡시실란(Methyltrimethoxysilane; MTMS) 중에서 선택되는 1종 이상의 경화촉진제를 더 포함하는 것을 특징으로 하는, 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물.
3. The method of claim 2,
In order to improve the curing rate during the condensation reaction of the alkoxysilane compound having a hydrophilic organic functional group and polydimethylsiloxane (PDMS) having a hydroxyl group,
Hydrophilic, characterized in that it further comprises at least one curing accelerator selected from Tetraethyl orthosilicate (TEOS), Tetramethyl orthosilicate (TMOS), and Methyltrimethoxysilane (MTMS) A polydimethylsiloxane derivative compound capable of surface formation.
 제7항에 있어서,
상기 친수성 유기관능기를 가지는 알콕시 실란화합물은 5 내지 50 중량부이고, 히드록시기를 가지는 폴리디메틸실록산은 50 내지 95 중량부, 상기 경화촉진제는 5 내지 30 중량부인 것을 특징으로 하는, 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물.
8. The method of claim 7,
The amount of the alkoxysilane compound having a hydrophilic organic functional group is 5 to 50 parts by weight, the polydimethylsiloxane having a hydroxyl group is 50 to 95 parts by weight, and the curing accelerator is 5 to 30 parts by weight. Dimethylsiloxane derivative compounds.
 제2항에 있어서,
상기 히드록시기를 가지는 폴리디메틸실록산의 중량평균 분자량은 1,000 내지 10,000 g/mol인 것을 특징으로 하는, 친수성 표면 형성이 가능한 폴리디메틸실록산 유도체 화합물.3. The method of claim 2,
A polydimethylsiloxane derivative compound capable of forming a hydrophilic surface, characterized in that the polydimethylsiloxane having a hydroxyl group has a weight average molecular weight of 1,000 to 10,000 g/mol. 삭제delete 삭제delete
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