TWI549996B - Biomimetic agent for anti-biofouling coating and method for making the same - Google Patents
Biomimetic agent for anti-biofouling coating and method for making the same Download PDFInfo
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- TWI549996B TWI549996B TW104105128A TW104105128A TWI549996B TW I549996 B TWI549996 B TW I549996B TW 104105128 A TW104105128 A TW 104105128A TW 104105128 A TW104105128 A TW 104105128A TW I549996 B TWI549996 B TW I549996B
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- 239000011248 coating agent Substances 0.000 title claims description 42
- 230000003592 biomimetic effect Effects 0.000 title claims description 40
- 238000000034 method Methods 0.000 title description 9
- 238000000576 coating method Methods 0.000 title description 5
- 239000003795 chemical substances by application Substances 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
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- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229920005604 random copolymer Polymers 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 5
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 claims description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 claims 1
- 241000335053 Beta vulgaris Species 0.000 claims 1
- 229940117986 sulfobetaine Drugs 0.000 claims 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 15
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- -1 mercapto, undecyl Chemical group 0.000 description 9
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- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 5
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
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- 238000007598 dipping method Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 150000001875 compounds Chemical class 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 3
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
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- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
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- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000000227 bioadhesive Substances 0.000 description 1
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- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
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- 210000003743 erythrocyte Anatomy 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- Paints Or Removers (AREA)
- Materials For Medical Uses (AREA)
Description
本發明係關於一種塗佈劑及其製造方法，特別關於一種抗生物分子沾黏之仿生塗佈劑及其製造方法。 The present invention relates to a coating agent and a method of manufacturing the same, and more particularly to a biomimetic coating agent resistant to biomolecules and a method of manufacturing the same.
在各種應用領域上，抗生物分子沾黏的表面處理為一重要技術。所謂抗生物分子沾黏的表面，通常例如具有抗蛋白質、血液、細胞、細菌等生物分子沾黏之表面。抗生物分子沾黏的表面處理所使用的塗佈劑，雖然根據習知技術，認為表面成為親水性，可有助於抗生物分子沾黏，然而其效果太差。 Surface treatment of bio-molecular adhesion is an important technology in various fields of application. The surface on which the biomolecule is adhered is usually, for example, a surface that is resistant to biomolecules such as proteins, blood, cells, bacteria, and the like. The coating agent used for the surface treatment of the biomolecule-resistant adhesive is considered to be hydrophilic according to the conventional technique, and contributes to the adhesion of the bio-resistant molecules, but the effect is too poor.
再者，雙離子性(zwitterionic)分子或具有雙離子性基團之聚合物，也被提出使用作為抗生物分子沾黏的塗佈劑，例如吳氏等人(L.Wu,J.Jasinski,S.Krishnan,J.Appl.Polymer Scienec,Vol.124,2154(2012))揭露使用具有羧基甜菜鹼基團、磺基甜 菜鹼基團及陽離子性之嵌段共聚物，作為塗佈劑，藉由旋轉塗佈法，對所欲處理的表面進行抗生物分子沾黏的表面處理。然而，由文獻中的圖8顯示的蛋白質吸附的效果，沒有達到80%以上的抗蛋白質分子吸附，顯示文獻中揭露之共聚物仍不足以作為抗生物分子沾黏效果良好之塗佈劑，而且抗生物分子沾黏的效果，尚包含抗血液、細胞、細菌等生物分子之沾黏，該些特性在文獻中並沒有探討。 Further, a zwitterionic molecule or a polymer having a diionic group is also proposed to be used as a coating agent for adhesion to biomolecules, such as W. et al. (L. Wu, J. Jasinski, S. Krishnan, J. Appl. Polymer Scienec, Vol. 124, 2154 (2012)) discloses the use of a carboxy-based beta group, sulfo-sweet The vegetable base group and the cationic block copolymer are subjected to a surface treatment of biomolecule adhesion to the surface to be treated by a spin coating method as a coating agent. However, the effect of protein adsorption shown in Fig. 8 in the literature did not reach more than 80% of anti-protein molecule adsorption, indicating that the copolymer disclosed in the literature is still insufficient as a coating agent with good adhesion to biomolecules, and The anti-biomolecule adhesion effect also contains the adhesion of biological molecules such as blood, cells and bacteria, and these characteristics are not discussed in the literature.
根據上述得知，雖然一般具有親水性、雙離子性基團等特性之表面，可以抗生物分子沾黏，然而要達到良好的抗生物分子沾黏之具有實用性的表面，仍需要藉由新的具有特定構造之化合物或塗佈劑，進行表面處理。 According to the above, although the surface having properties such as hydrophilicity and diionic groups is generally resistant to biomolecules, it is necessary to achieve a good surface which is resistant to biomolecules and has a practical surface. A compound or coating agent having a specific configuration is subjected to surface treatment.
鑒於上述發明背景中，為了符合產業上之要求，本發明提供一種抗生物分子沾黏之仿生塗佈劑及其製造方法，藉由具有雙離子性(zwitterionic)基團或擬雙離子性基團且具有特定結構的聚合物，作為抗生物分子沾黏的有效成分，達到抗生物分子沾黏之效果。 In view of the above-mentioned background of the invention, in order to meet the requirements of the industry, the present invention provides a biomimetic coating agent resistant to biomolecules and a method for producing the same, which has a zwitterionic group or a pseudo-ionic group. The polymer with a specific structure acts as an effective component against the adhesion of biomolecules, and achieves the effect of resisting the adhesion of biomolecules.
本發明之目的之一，在於提供一種抗生物分子沾黏之仿生塗佈劑，藉由例如浸漬法、旋轉塗佈法等簡易習知之塗佈法，可應用於例如聚合物、金屬、陶瓷等各種材料所構成之表面或多孔性表面，提供抗生物分子沾黏的表面。 One of the objects of the present invention is to provide a biomimetic coating agent which is resistant to biomolecules, and can be applied to, for example, polymers, metals, ceramics, etc. by a simple coating method such as a dipping method or a spin coating method. A surface or porous surface of various materials that provides a surface that is resistant to biomolecules.
本發明之目的之一，在於提供一種抗生物分子沾黏之仿生塗佈劑之製造方法，藉由例如浸漬法、旋轉塗佈法等簡易習知之塗佈法，可容易應用於大面積的表面及多孔性表面，進一步可容易地大量生產，無需特殊或大型設備，可降低生產成本。 One of the objects of the present invention is to provide a method for producing a biomimetic coating agent which is resistant to biomolecules, and can be easily applied to a large-area surface by a simple coating method such as a dipping method or a spin coating method. And the porous surface can be easily mass-produced without special or large equipment, which can reduce production costs.
綜上所述，本發明揭露了一種抗生物分子沾黏之仿生塗佈劑，其係由一般式(1)：AUmBUn的嵌段共聚物、無規共聚物或交替共聚物所構成，AU表示具有錨定基團之重複單元，BU表示具有雙離子性基團或擬雙離子性基團之重複單元，m表示5~120的整數，n表示5~120的整數，其中AU表示式(2)：-CR1R2CH2-所示之二價的具有取代基之伸乙基，BU表示式(3)：-CR3(CH3)CH2-所示之二價的具有取代基之伸乙基或式(4)：-CR4HCR5H-所示之二價的具有取代基之伸乙基，R1表示碳數3~18之直鏈狀、 分支鏈狀或環狀烷基、酯基(亦即-COORx，其中Rx表示碳數3~18之直鏈狀、分支鏈狀或環狀烷基、芳香基或碳數5~12之雜芳基)、具有碳數1~18之烷基取代基之苯基或碳數5~12之雜芳基(heteroaryl)，R2表示氫原子或甲基，R3表示-COOR’或-CONR”H，R4表示氫原子時，R5表示-COOR’或-CONR”H，R’及R”分別獨立表示甜菜鹼基(betaine moiety)、磺基甜菜鹼基(sulfobetaine moiety)或羧基甜菜鹼基(carboxybetaine moiety)，R4表示羧基時，R5表示陽離子性基。 In summary, the present invention discloses a biomimetic-coated biomimetic coating agent which is composed of a block copolymer, a random copolymer or an alternating copolymer of the general formula (1): AU m BU n . , AU represents a repeating unit having an anchor group, BU represents a repeating unit having a diionic group or a pseudo-ionic group, m represents an integer of 5 to 120, and n represents an integer of 5 to 120, wherein AU represents Formula (2): -CR 1 R 2 CH 2 - a divalent substituted ethyl group having a substituent, and BU represents a divalent formula represented by the formula (3): -CR 3 (CH 3 )CH 2 - a pendant ethyl group having a substituent or a divalent substituted ethyl group having a substituent represented by -CR 4 HCR 5 H-, and R 1 representing a linear or branched chain having a carbon number of 3 to 18. Or a cyclic alkyl group or an ester group (ie, -COOR x , wherein R x represents a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, an aromatic group or a heteroaryl group having 5 to 12 carbon atoms; a phenyl group having an alkyl substituent of 1 to 18 carbon atoms or a heteroaryl group having 5 to 12 carbon atoms, R 2 represents a hydrogen atom or a methyl group, and R 3 represents -COOR' or -CONR"H When R 4 represents a hydrogen atom, R 5 represents -COOR' or -CONR"H, R' and R" are respectively Li represents a betaine moiety, a sulfobetaine moiety or a carboxybetaine moiety, and when R 4 represents a carboxyl group, R 5 represents a cationic group.
再者，本發明揭露了一種抗生物分子沾黏之仿生塗佈劑之製造方法，包括提供一具有錨定基團之單體；提供一具有雙離子性基團或擬雙離子性基團之單體；以及藉由原子轉移自由基聚合法(Atomic transfer radical polymerization)，在觸媒及聚合引發劑的存在下，在氮氣環境中，使該具有錨定基團之單體與該具有雙離子性基團或擬雙離子性基團之單體聚合反應而形成一般式(1)：AUmBUn表示的嵌段共聚物、無規共聚物或交替共聚物。 Furthermore, the present invention discloses a method for producing a biomimetic-coated biomimetic coating agent, comprising providing a monomer having an anchor group; and providing a diionic group or a pseudo-ionic group. Monomer; and the monomer having an anchor group and the double ion in a nitrogen atmosphere by atomic transfer radical polymerization in the presence of a catalyst and a polymerization initiator The monomer of the group or the diionic group is polymerized to form a block copolymer, a random copolymer or an alternating copolymer represented by the general formula (1): AU m BU n .
此外，本發明揭露了一種抗生物分子沾黏之仿生塗佈組成物，包括：上述抗生物分子沾黏之仿生塗佈劑以及溶劑。 In addition, the present invention discloses a biomimetic coating composition resistant to biomolecules, comprising: the above biocide-adhering biomimetic coating agent and a solvent.
根據本發明之抗生物分子沾黏之仿生塗佈劑及其製造方法，藉由具有雙離子性(zwitterionic)基團且具有特定結構的聚合物，作為抗生物分子沾黏的有效成分，達到良好的抗生物分子沾黏之效果，藉由例如浸漬法、旋轉塗佈法等簡易習知之塗佈法，可容易應用於大面積的表面及多孔性表面，進一步可容易地大量生產，無需特殊或大型設備，可降低生產成本。 According to the biomimetic-coated biomimetic coating agent of the present invention and a method for producing the same, a polymer having a specific structure having a zwitterionic group is effective as an active component against biomolecule adhesion. The anti-biomolecule adhesion effect can be easily applied to a large-area surface and a porous surface by a simple coating method such as a dipping method or a spin coating method, and can be easily mass-produced without special or Large equipment can reduce production costs.
本發明在此所探討的方向為抗生物分子沾黏之仿生塗佈劑及其製造方法，為了能徹底地瞭解本發明，將在下列的描述中提出詳盡的結構及其元件與方法步驟。顯然地，本發明的施行並未限定於塗佈劑之技藝者所熟習的特殊細節。另一方面，眾所周知的結構及其元件並未描述於細節中，以避免造成本發明不必要之限制。此外，為提供更清楚之描述及使熟悉該項技藝者能理解本發明之發明內容，圖示內各部分並沒有 依照其相對之尺寸而繪圖，某些尺寸與其他相關尺度之比例會被突顯而顯得誇張，且不相關之細節部分亦未完全繪出，以求圖示簡潔。本發明的較佳實施例會詳細描述如下，然而除了這些詳細描述之外，本發明還可以廣泛地施行在其他的實施例中，且本發明範圍不受限定，其以之後的專利範圍為準。 The present invention is directed to a biomimetic coating agent that is resistant to biomolecules and a method of making the same. In order to fully understand the present invention, detailed structures, elements, and method steps thereof are set forth in the following description. Obviously, the practice of the present invention is not limited to the particular details familiar to those skilled in the art of coating agents. On the other hand, well-known structures and elements thereof are not described in detail to avoid unnecessary limitation of the invention. In addition, in order to provide a clearer description and to enable those skilled in the art to understand the present invention, the various parts of the illustration are not Drawing according to its relative size, the ratio of certain dimensions to other related scales will be highlighted and exaggerated, and the irrelevant details are not fully drawn for the sake of simplicity. The preferred embodiments of the present invention are described in detail below, but the present invention may be widely practiced in other embodiments and the scope of the present invention is not limited by the scope of the appended claims.
本發明揭露之抗生物分子沾黏之仿生塗佈劑，藉由塗佈於一表面，進行抗生物分子沾黏之表面處理，可達到良好之抗生物分子沾黏的效果，例如成為抗蛋白質、血液、細胞、細菌等生物分子沾黏之表面。本發明之仿生塗佈劑，係指具有仿生物分子的構造之化合物，藉由具有雙離子性基團之特定構造之化合物，可抗生物分子沾黏，再者雖然塗佈劑通常有附著不佳的問題，本發明之塗佈劑藉由具有特定結構之錨定基團，提供良好的塗佈性、成膜性及表面附著性。 The biomolecular-coated biomimetic coating agent disclosed in the invention can be applied to a surface for anti-biomolecular adhesion surface treatment, thereby achieving good anti-biomolecular adhesion effect, for example, becoming anti-protein, A surface on which biological molecules such as blood, cells, and bacteria adhere. The biomimetic coating agent of the present invention refers to a compound having a structure of a biomimetic molecule, which is resistant to biomolecules by a compound having a specific structure of a diionic group, and although the coating agent usually has no adhesion. A good problem is that the coating agent of the present invention provides good coatability, film formability and surface adhesion by anchoring groups having a specific structure.
根據本發明之一實施態樣，揭露一種抗生物分子沾黏之仿生塗佈劑，其係由一般式(1)：AUmBUn的嵌段共聚物、無規共聚物或交替共聚物所構成，AU表示具有錨定基團之重複單元，BU表示具有雙離子性基團或擬雙離子性基團之重複單元，m表示5~120的 整數，n表示5~120的整數，其中AU表示式(2)：-CR1R2CH2-所示之二價的具有取代基之伸乙基，BU表示式(3)：-CR3(CH3)CH2-所示之二價的具有取代基之伸乙基或式(4)：-CR4HCR5H-所示之二價的具有取代基之伸乙基。具體地，上述抗生物分子沾黏之仿生塗佈劑具有一般式(A)或(B)之構造，其中，式中，R1、R2、R3、R4及R5表示與上述相同意義。 According to an embodiment of the present invention, a biomimetic coating agent resistant to biomolecules is disclosed, which is a block copolymer, a random copolymer or an alternating copolymer of the general formula (1): AU m BU n . Composition, AU represents a repeating unit having an anchor group, BU represents a repeating unit having a diionic group or a pseudo-ionic group, m represents an integer of 5 to 120, and n represents an integer of 5 to 120, wherein AU The formula (2): -CR 1 R 2 CH 2 - represents a divalent substituted ethyl group having a substituent, and BU represents a divalent group represented by the formula (3): -CR 3 (CH 3 )CH 2 - The pendant ethyl group having a substituent or the divalent ethyl group having a substituent represented by the formula (4): -CR 4 HCR 5 H-. Specifically, the biomimetic-coated biomimetic coating agent has a structure of the general formula (A) or (B), wherein, in the formula, R 1 , R 2 , R 3 , R 4 and R 5 represent the same as described above. significance.
R1表示碳數3~18之直鏈狀、分支鏈狀或環狀烷基、酯基(亦即-COORx，其中Rx表示碳數3~18之 直鏈狀、分支鏈狀或環狀烷基、芳香基或碳數5~12之雜芳基)、芳香基或碳數5~12之雜芳基(heteroaryl)。 R 1 represents a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, and an ester group (that is, -COOR x , wherein R x represents a linear, branched chain or ring having 3 to 18 carbon atoms; An alkyl group, an aryl group or a heteroaryl group having 5 to 12 carbon atoms, an aromatic group or a heteroaryl group having 5 to 12 carbon atoms.
碳數3~18之直鏈狀、分支鏈狀或環狀烷基之具體例，例如丙基、異丙基、丁基、異丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、環戊基、環己基、環庚基等。酯基(-COORx)之具體例，例如十八烷氧基羰基、十六烷氧基羰基、十四烷氧基羰基、己氧基羰基、丁氧基羰基、苯氧基羰基(phenoxycarbonyl；-C(=O)-OC6H5)、苯甲氧基羰基(-C(=O)-OCH2C6H5)及N,N-二苯基胺基對苯甲氧基羰基(-C(=O)-OCH2(C6H4)N(C6H5)2)等。 Specific examples of a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, such as propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, heptyl, octyl, decyl , mercapto, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, cyclopentyl, cyclohexyl , cycloheptyl and the like. Specific examples of the ester group (-COOR x ), such as octadecyloxycarbonyl, hexadecyloxycarbonyl, tetradecyloxycarbonyl, hexyloxycarbonyl, butoxycarbonyl, phenoxycarbonyl; -C(=O)-OC 6 H 5 ), benzyloxycarbonyl (-C(=O)-OCH 2 C 6 H 5 ) and N,N-diphenylamino-p-phenylmethoxycarbonyl ( -C(=O)-OCH 2 (C 6 H 4 )N(C 6 H 5 ) 2 ).
芳香基之具體例，例如苯基、甲苯基、苯甲基等。碳數5~12之雜芳基之具體例，例如2-吡啶基。上述化學式中最左側之「-」表示結合於主鏈之鍵結，以下亦表示相同意義。 Specific examples of the aromatic group include a phenyl group, a tolyl group, a benzyl group and the like. Specific examples of the heteroaryl group having 5 to 12 carbon atoms are, for example, 2-pyridyl. The leftmost "-" in the above chemical formula means a bond bonded to the main chain, and the following also means the same meaning.
R2表氫原子或甲基；R3表-COOR’或-CONR”H；R4表氫原子(-H)時，R5表-COOR’或-CONR”H，R’及R”分別獨立表示甜菜鹼基(betaine group)、磺基甜菜鹼基(sulfobetaine group)或羧基甜菜鹼基(carboxybetaine group)；R4表示羧基(-COOH)時，R5表示陽離子性基；m表示5~120的整數，n表示5~120的整數。m為10~80且n為10~80較理想，n為20~40且n為20~40更加理想。 R 2 represents a hydrogen atom or a methyl group; R 3 represents -COOR' or -CONR"H; when R 4 represents a hydrogen atom (-H), R 5 represents -COOR' or -CONR"H, R' and R" respectively Independently indicates a betaine group, a sulfobetaine group or a carboxybetaine group; when R 4 represents a carboxyl group (-COOH), R 5 represents a cationic group; m represents 5~ An integer of 120, n represents an integer from 5 to 120. m is 10 to 80 and n is preferably 10 to 80, n is 20 to 40, and n is 20 to 40.
R5所示之陽離子性基，例如為N,N-二甲基銨基伸乙基胺基乙烯基(N,N-dimethylammnio-ethylene-1-amino-vinyl；-C(=CH2)NH2CH2CH2N(CH3)2H)、N,N-二甲基銨基伸丙基胺基乙烯基(N,N-dimethylammnio-propylene-1-amino-vinyl；-C(=CH2)NH2CH2CH2CH2N(CH3)2H)、N,N-二甲基銨基伸丁基胺基乙烯基(N,N-dimethylammnio-butylene-1-amino-vinyl；-C(=CH2)NH2CH2CH2CH2CH2N(CH3)2H)、N,N-二甲基銨基伸戊基胺基乙烯基(N,N-dimethylammnio-pentylene-1-amino-vinyl；-C(=CH2)NH2CH2CH2CH2CH2CH2N(CH3)2H)。 The cationic group represented by R 5 is, for example, N,N-dimethylammonio-ethylene-1-amino-vinyl;-C(=CH 2 )NH 2 CH 2 CH 2 N(CH 3 ) 2 H), N,N-dimethylammonium propylaminovinyl (N, N-dimethylammnio-propylene-1-amino-vinyl; -C(=CH 2 ) NH 2 CH 2 CH 2 CH 2 N(CH 3 ) 2 H), N,N-dimethylammonium butylaminovinyl (N, N-dimethylammnio-butylene-1-amino-vinyl; -C ( =CH 2 )NH 2 CH 2 CH 2 CH 2 CH 2 N(CH 3 ) 2 H), N,N-dimethylammonium pentylamino vinyl (N, N-dimethylammnio-pentylene-1-amino -vinyl; -C(=CH 2 )NH 2 CH 2 CH 2 CH 2 CH 2 CH 2 N(CH 3 ) 2 H).
更具體地，本發明之抗生物分子沾黏之仿生塗佈劑，具有以下的化學構造。 More specifically, the biomolecular-coated biomimetic coating agent of the present invention has the following chemical structure.
其中，上述式(A-1)~(A-21)所示的仿生塗佈劑具有棒狀的錨定基團，m及n表示與上述相同的意義，上述式(A-1)~(A-21)所示的仿生塗佈劑可為嵌段共聚物、無規共聚物或交替共聚物。 Here, the biomimetic coating agent represented by the above formulas (A-1) to (A-21) has a rod-shaped anchor group, and m and n have the same meanings as described above, and the above formula (A-1) to ( The biomimetic coating agent shown in A-21) may be a block copolymer, a random copolymer or an alternating copolymer.
再者，本發明之抗生物分子沾黏之仿生塗佈劑，具有以下的化學構造。下述式(A-22)~(A-33)所示的仿生塗佈劑具有梳子狀(comb-like)的錨定基團，m及n表示與上述相同的意義，上述式(A-22)~(A-33)所示的仿生塗佈劑可為嵌段共聚物、無規共聚物或交替共聚物。 Further, the biomimetic coating agent to which the antibiotic molecule of the present invention is adhered has the following chemical structure. The biomimetic coating agent represented by the following formulas (A-22) to (A-33) has a comb-like anchor group, and m and n have the same meanings as described above, and the above formula (A- 22) The biomimetic coating agent shown in ~(A-33) may be a block copolymer, a random copolymer or an alternating copolymer.
再者，本發明之抗生物分子沾黏之仿生塗佈劑，具 有以下的化學構造，其中，式(B-1)及(B-2)所示之仿生塗佈劑為交替共聚物。 Furthermore, the antibiotic bioadhesive biomimetic coating agent of the present invention has There are the following chemical structures in which the biomimetic coating agents represented by the formulae (B-1) and (B-2) are alternating copolymers.
再者，本發明之抗生物分子沾黏之仿生塗佈劑，具有以下的化學構造，其中，式(B-3)所示之仿生塗佈劑可為無規或嵌段共聚物。 Further, the biomolecular-coated biomimetic coating agent of the present invention has the following chemical structure, wherein the biomimetic coating agent represented by the formula (B-3) may be a random or block copolymer.
再者，本發明之抗生物分子沾黏之仿生塗佈劑，具有以下的化學構造，其中，式(C-1)~(C-6)所示之仿生塗佈劑可為嵌段、無規或交替共聚物，具有可交聯性之錨定基團，塗佈於一表面後，可藉由加熱而相互交聯。 Furthermore, the biomimetic-coated biomimetic coating agent of the present invention has the following chemical structure, wherein the biomimetic coating agent represented by the formulae (C-1) to (C-6) may be a block or not. Or alternating copolymers having crosslinkable anchoring groups which, after being applied to a surface, can be crosslinked by heating.
製造範例1：製備A-33(PODA-b-PSBMA) Manufacturing Example 1: Preparation of A-33 (PODA- b- PSBMA)
將甲基丙烯酸十八烷酯(octadecyl acrylate；ODA)溶解於甲苯，成為40重量%的溶液，藉由原子轉移自由基聚合法，在溴化亞銅/聯吡啶(CuBr/2,2’-bipyridine；CuBr/bpy)作為觸媒及2-溴丙酸甲酯(methyl 2-bromopropionate；MBrP)作為聚合引發劑的存在下，在氮氣環境下，各成分混合比例，以莫耳比為[ODA]/[MBrP]/[CuBr]/[bpy]為6/1/1/2~120/1/1/2，在120℃，進行聚合反應24小時，除去觸媒及溶劑後，得到聚丙烯酸十八烷酯(PODA)。 The octadecyl acrylate (ODA) was dissolved in toluene to obtain a 40% by weight solution by atom transfer radical polymerization in cuprous bromide/bipyridine (CuBr/2, 2'- Bipyridine;CuBr/bpy) as a catalyst and methyl 2-bromopropionate (MBrP) as a polymerization initiator, in a nitrogen atmosphere, the mixing ratio of each component, with molar ratio [ODA] ]/[MBrP]/[CuBr]/[bpy] is 6/1/1/2~120/1/1/2, and polymerization reaction is carried out at 120 ° C for 24 hours to remove the catalyst and solvent to obtain polyacrylic acid. Octadecyl ester (PODA).
然後，藉由原子轉移自由基聚合法聚合甲基丙烯酸2-(2-二甲基胺基)乙酯(DMAEMA)與PODA，並以莫耳比為[DMAEMA]/[PODA]/[CuBr]/[bpy]為5/1/1/2~100/1/1/2，於120℃下進行24小時聚 合反應，除去觸媒及溶劑後可得共聚物A-33P(Poly(octadecyl acrylate)-b-poly(2-(dimethylamino)ethyl methacrylate))。再於THF中溶解1,3-丙烷磺內酯(1,3-propanesultone)與共聚物A-33P，在大氣下，將共聚物A-33P甜菜鹼化(Betainization)，進行反應24小時後，得到共聚物A-33。 Then, 2-(2-dimethylamino)ethyl methacrylate (DMAEMA) and PODA are polymerized by atom transfer radical polymerization, and the molar ratio is [DMAEMA]/[PODA]/[CuBr] /[bpy] is 5/1/1/2~100/1/1/2, and polymerization is carried out at 120 ° C for 24 hours. After removing the catalyst and solvent, the copolymer A-33P (Poly(octadecyl acrylate) can be obtained. - b -poly(2-(dimethylamino)ethyl methacrylate)). Further, 1,3-propanesultone and copolymer A-33P were dissolved in THF, and the copolymer A-33P was betained under the atmosphere, and the reaction was carried out for 24 hours. Copolymer A-33 was obtained.
製造範例2：製備B-3(Poly((1-octadecene)-alt-((acrylic acid)-(N-(3-(dimethylamino)ethyl)acrylamide)))；Poly(ODA-alt-(AA-DMAPAMMI)) Manufacturing Example 2: Preparation of B-3 (Poly((1-octadecene)- alt -((acrylic acid)-(N-(3-(dimethylamino)ethyl)acrylamide)))); Poly (ODA- alt - (AA-) DMAPAMMI))
配製濃度為10重量%聚(順丁烯二酸酐-交替-1-十八烯)(poly(maleic anhydride alt 1-octadecene)；PMAO)溶液2毫升，使用THF作為溶劑。另外配製二甲基伸乙基二胺(Dimethylethylenediamine；DMEA)(3.2g)的THF(8毫升)溶液。將PMAO 溶液加入DMEA溶液，產生沈澱，藉由離心、萃取，得到共聚物B-3。 2 ml of a solution of 10% by weight of poly(maleic anhydride alt 1-octadecene; PMAO) was prepared, and THF was used as a solvent. A solution of dimethyldiethyldiamine (DMEA) (3.2 g) in THF (8 mL) was then obtained. PMAO The solution was added to the DMEA solution to produce a precipitate, which was centrifuged and extracted to obtain a copolymer B-3.
其他上述舉例之抗生物分子沾黏之仿生塗佈劑，可藉由類似上述製造範例1或2或整合其他習知聚合方法之改良方法而製造。根據本發明人等的實驗，證實上述本發明之仿生塗佈劑，具有良好的抗生物分子沾黏之特性，特別是例如蛋白質分子為血漿蛋白、纖維蛋白原、血清白蛋白；血液例如為紅血球、白血球、血小板；細胞例如為人體細胞、成纖維細胞、角質細胞；細菌例如為表皮葡萄球菌、大腸桿菌等。亦即低於20%的生物分子會沾黏於處理過之表面，在較佳的情況，低於2%的生物分子會沾黏於處理過之表面。 Other biomolecular-coated biomimetic coating agents of the above-exemplified examples can be produced by an improved method similar to the above-described manufacturing example 1 or 2 or integrating other conventional polymerization methods. According to experiments by the present inventors, it has been confirmed that the above-mentioned biomimetic coating agent of the present invention has good biomolecular adhesion characteristics, in particular, for example, protein molecules are plasma proteins, fibrinogen, serum albumin; blood such as red blood cells , white blood cells, platelets; cells such as human cells, fibroblasts, keratinocytes; bacteria such as Staphylococcus epidermidis, Escherichia coli and the like. That is, less than 20% of the biomolecules will stick to the treated surface. In the preferred case, less than 2% of the biomolecules will stick to the treated surface.
再者，本發明揭露一種抗生物分子沾黏之塗佈組成物，包括：本發明之抗生物分子沾黏之仿生塗佈劑及溶劑。溶劑例如為水、生理食鹽水飽和液(PBS)、醇類(例乙醇、甲醇)等。本發明之抗生物分子沾黏之仿生塗佈劑或塗佈組成物，可應用於各種表面，例如聚合物構成的表面(PTFE、PVDF、PS、PP、PVC)或無機氧化物構成的表面(SiO2、Al2O3)。又，金屬表面(例如Fe、Ti)亦可藉本發明之抗生物分子沾黏之仿生塗 佈劑或塗佈組成物，進行抗生物分子沾黏之表面處理。 Furthermore, the present invention discloses a coating composition resistant to biomolecules, comprising: a biomimetic coating agent and a solvent which are resistant to biomolecules of the present invention. The solvent is, for example, water, physiological saline saturated solution (PBS), alcohol (for example, ethanol, methanol) or the like. The biomolecular-coated biomimetic coating agent or coating composition of the invention can be applied to various surfaces, such as a surface composed of a polymer (PTFE, PVDF, PS, PP, PVC) or a surface composed of an inorganic oxide ( SiO 2 , Al 2 O 3 ). Further, the metal surface (for example, Fe, Ti) may be subjected to a biomolecular adhesion surface treatment by the biomimetic coating agent or coating composition of the present invention.
綜上所述，根據本發明之抗生物分子沾黏之仿生塗佈劑及其製造方法，藉由具有雙離子性(zwitterionic)基團且具有特定結構的聚合物，作為抗生物分子沾黏的有效成分，達到良好的抗生物分子沾黏之效果，藉由例如浸漬法、旋轉塗佈法等簡易習知之塗佈法，可容易應用於大面積的表面及多孔性表面，進一步可容易地大量生產，無需特殊或大型設備，可降低生產成本。 In summary, the biomolecular-coated biomimetic coating agent and the method for producing the same according to the present invention are adhered to an antibiotic molecule by a polymer having a zwitterionic group and having a specific structure. The active ingredient can achieve a good anti-biomolecular adhesion effect, and can be easily applied to a large-area surface and a porous surface by a simple coating method such as a dipping method or a spin coating method, and can be easily easily mass-produced. Production, without special or large equipment, can reduce production costs.
顯然地，依照上面實施例中的描述，本發明可能有許多的修正與差異。因此需要在其附加的權利要求項之範圍內加以理解，除了上述詳細的描述外，本發明還可以廣泛地在其他的實施例中施行。上述僅為本發明之較佳實施例而已，並非用以限定本發明之申請專利範圍；凡其它未脫離本發明所揭示之精神下所完成的等效改變或修飾，均應包含在下述申請專利範圍內。 Obviously, many modifications and differences may be made to the invention in light of the above description. It is therefore to be understood that within the scope of the appended claims, the invention may be The above are only the preferred embodiments of the present invention, and are not intended to limit the scope of the claims of the present invention; all other equivalent changes or modifications which are not departing from the spirit of the present invention should be included in the following claims. Within the scope.
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