CN101090916A - 以聚乙烯醇和聚乙烯醇共聚物为基础的新型水凝胶 - Google Patents
以聚乙烯醇和聚乙烯醇共聚物为基础的新型水凝胶 Download PDFInfo
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- CN101090916A CN101090916A CNA2005800164528A CN200580016452A CN101090916A CN 101090916 A CN101090916 A CN 101090916A CN A2005800164528 A CNA2005800164528 A CN A2005800164528A CN 200580016452 A CN200580016452 A CN 200580016452A CN 101090916 A CN101090916 A CN 101090916A
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- FZICDBOJOMQACG-UHFFFAOYSA-N benzo[h]isoquinoline Chemical compound C1=NC=C2C3=CC=CC=C3C=CC2=C1 FZICDBOJOMQACG-UHFFFAOYSA-N 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
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- 239000004913 cyclooctene Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229960001708 magnesium carbonate Drugs 0.000 description 1
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- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 229910000400 magnesium phosphate tribasic Inorganic materials 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
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- 239000000178 monomer Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
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- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 229940093916 potassium phosphate Drugs 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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Abstract
本发明涉及含具有特殊几何结构的聚乙烯醇和/或聚乙烯醇共聚物的水凝胶,制造水凝胶的工艺方法和水凝胶在生物医药和药剂领域中作为材料的应用,用于制造接触镜片、控制活性物的释放和作为包涵固定化生物催化剂的载体材料、作为钻孔液的添加物、作为采油的置换剂、作为水泥的助剂和作为高粘度液体的添加剂,例如用于改善石油的流动性能和快速输送以及作为化妆品的组分。
Description
本发明涉及含有聚乙烯醇和/或聚乙烯醇共聚物的水凝胶,制造水凝胶的工艺方法和水凝胶在生物医药和药剂领域中作为材料的应用,用于制造接触镜片、控制活性物质的释放、作为包涵固定化生物催化剂的载体材料,作为过渡金属催化剂的载体材料、作为制造活性膜的材料、作为钻孔液的添加物、作为采油置换剂、作为水泥助剂和作为高粘度液体添加剂,例如为改善石油的流动性能和快速输送以及作为化妆品的组分。
水凝胶是以亲水性的聚合物为基础的含水凝胶,它是三维网状物,该聚合物作为水凝胶不溶于水,但可溶胀至平衡状态的容积并在相当大的程度上保持其形状。网状物的生成主要是通过各个聚合物链的化学结合,但也可以在各聚合物链的节段之间通过静电、疏水的或偶极/偶极-互相作用的物理过程实现。通过对构成聚合物的单体、交联类型和交联密度的选择可有目的地调节水凝胶所要求的性能,聚合物所必需的亲水性可借助于羟基、羧基、磺酸(盐)酯基或酰胺基等获得。合成的水凝胶是以聚(甲基)丙烯酸、聚(甲基)丙烯酸酯、聚乙烯基吡咯烷酮或聚乙烯醇等作为基础,一般情况下水凝胶与活的组织有良好的相容性(源自Rmpp Lexikon Chemie-Version 2.0,Stuttgart/NewYork:Georg Thieme Verlag 1999)。
以聚乙烯醇为基础的水凝胶是熟知的(参见US2003008396A1,US2001029399A1,US0006231605B1,US0005981826A,WO2001044307A3,WO1998050017A1,Hassan,Christie M.;Peppas,Nikolaos,A.;Advances in Polymer Science(2000),153(Biopolymers,PVA Hydrogels Anionic Polymerisation Nanocomposites),37-65,Peppas,Nikolaos A.,Hydrogels Med.Pharm.(1987),2,1-48,和其所引用的文献)。以聚乙烯醇为基础的水凝胶可用各种不同的方法制造,例如一聚乙烯醇水溶液经过反复冷冻和融解,用有离子化作用的射线(紫外线,γ-射线)辐照聚乙烯醇水溶液以及聚乙烯醇通过与交联剂,如戊二醛、乙醛、甲醛、马来酸、草酸、海藻酸、二甲基脲、乙二醛、盐酸、聚丙烯醛、二异氰酸酯和/或硫酸二乙烯酯反应。
以聚乙烯醇为基础的水凝胶一般是由常规的线型聚乙烯醇制取的,此处的水凝胶由于结晶区而导致有浑浊现象,这使得由常规聚乙烯醇制取的水凝胶只能有条件地适用于如接触镜片的光学用途。此外,由常规聚乙烯醇得到的水凝胶只有经凝胶交联才能获得其机械性能。
令人惊喜地发现,有特殊几何结构,如星形几何结构的聚乙烯醇水凝胶在凝胶中显示出有较少的微结晶度,从而能导致其光学性能和机械性能的改善,在DE10343607(Schulte et al./Celanese VenturesGmbH)和DE10356574(Bruckmann et al./Celanese Ventures GmbH)中曾对其作过描述。此外,在形成水凝胶之前通过聚合物的交联所得到的聚乙烯醇的特殊几何结构能降低其磨耗。
因而,本发明的对象是含有至少一聚乙烯醇-星形聚合物的水凝胶。
在本发明范围内的水凝胶含有至少一种聚乙烯醇-星形聚合物,它既包括那些全部用一种或许多聚乙烯醇-星形聚合物作为聚合物的水凝胶,也包括那些聚乙烯醇-星形聚合物与其它聚合物之间的混合物,此处尤其优选是聚乙烯醇-星形聚合物与常规的聚乙烯醇之比为99∶1至1∶99的混合物。另外,特别优选是聚乙烯醇-星形聚合物与聚丙烯酸、聚甲基丙烯酸、聚丙烯酸酯、聚甲基丙烯酸酯和聚乙烯基吡咯烷酮之比为99∶1至1∶99的混合物。
按本发明的水凝胶除上述的聚乙烯醇-星形聚合物外,对其名称已作说明,它还含有水。
含有特殊几何结构的聚乙烯醇可采用不同的方法制造:其一是由经一过渡金属催化剂制造的聚醋酸乙烯,如在DE10238659中说明的方法,经皂化,如在DE10343607中所说明的;或者是经过醋酸乙烯与一可交联的共聚单体进行共聚,再经皂化,如在DE10356574中所述的。
下面是表示在DE10343607和DE10356574中描述的聚乙烯醇和聚乙烯醇共聚物作为聚乙烯醇-星形聚合物。
按DE10343607和DE10356574的聚乙烯醇-星形聚合物是指式I,II或III的化合物。
其中
Pol是以一聚乙烯醇为基础的聚合物,特别优选是以聚乙烯醇为基础的均聚和共聚物,尤其特别优选是聚乙烯醇、聚乙烯醇-聚醋酸乙烯共聚物、聚乙烯醇-聚乙烯共聚物、聚乙烯醇-聚氯乙烯共聚物和聚乙烯醇-聚丙烯酸甲酯共聚物,和
Z是中心原子和元素周期表中的第13至16族的一个原子,优选是碳、硅、氮、磷、氧或硫,特别优选是碳或硅,和
X1各为相同或不同的卤素原子,优选是氟、氯、溴或碘,特别优选是氯、溴和碘,和
R1相同或不同,为氢或C1-C20的含碳基团,和
R2相同或不同,为在中心原子Z和起始单元[R3-X1]之间一架桥的C1-C20的含碳基团或是硅或氧,和
R3相同或不同,为碳或硅,和
R4相同或不同,为一氢原子或一C1-C20含碳基团,和
R5相同或不同,为氢或一C1-C20含碳基团,
l为一自然整数0,1,2或3,和
m各为相同或不同,为一自然整数0,1,2,3,4和5,和
n各为相同或不同,为一自然整数0,1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19和20,和
o各为相同或不同,为1或2,和
p各为相同或不同,为一自然整数1,2,3,4和5,和
q为一自然整数2,3和4,和
Ar为带有至少4个C-原子,可被硼、氮或磷所替换一个或多个碳原子的芳族基础构架,此处优选的芳族或杂芳族基础构架是从苯、联苯、萘、蒽、菲、苯并菲、喹啉、吡啶、联吡啶、哒嗪、嘧啶、吡嗪、三嗪、苯并吡咯、苯并三唑、苯并吡啶、苯并吡嗪烷(Benzopyrazidin)、苯并嘧啶、苯并吡嗪、苯并三嗪、吲嗪、喹嗪、咔唑、吖啶、吩嗪、苯并喹啉、吩嗪,有时可能是它们的取代物所衍生的,和
y为一自然整数0,1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19和20,和
z为一自然整数2,3,4,5,6,7,8,9和10。
Ap为至少一带有3个碳原子的环状非芳族的基础架构,所带碳原子可含有如氮、硼、磷、氧或硫的杂原子,此处优选的脂肪族基础构架是从环烷基类基团,例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基、或是从环杂烷基类基团,例如氮杂环丙烷、氮杂环丁烷、吡咯烷、哌啶、氮杂卓烷(Azepane)、吖辛因烷(Azocane)、1,3,5-三嗪烷(1,3,5-Triaziman)、1,3,5-三、氧杂环丁烷、呋喃、二氢呋喃、四氢呋喃、吡喃、二氢吡喃、四氢吡喃、庚烷(Oxepan)、Oxocan或从糖类基团,例如α-葡萄糖、β-葡萄糖,衍生的,和
a为一自然整数1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19和20,和
b为一自然整数2,3,4,5,6,7,8,9和10,和
c为一自然整数1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19和20,
d相同或不同,为0或1,以及
以聚乙烯基酯共聚物为基础的聚乙烯醇共聚物通过包括下述步骤的工艺方法可获得:
A)在能产生自由基的化合物和往往还有自由基捕获物存在时,乙烯基酯进行自由基溶液聚合或本体聚合,
B)加入具有交联能力的聚链烯基化合物,
C)所生成的聚乙烯酯共聚物往往要进行加工处理和分离,
D)在B)步骤制取的聚乙烯基酯/聚乙烯基酯-聚烯烃-混合物或在C)步骤分离出的聚乙烯基酯-聚烯烃-共聚物用碱皂化而生成聚乙烯醇/聚乙烯醇-聚烯烃-混合物或聚乙烯醇-聚烯烃-共聚物和分离该产品,其特征在于,在B)步骤中加入的聚烯烃化合物是指式IV的化合物:
其中
R6为-C6-C20芳基、-C5-C20杂芳基、-C4-C20环烷基、-C4-C20杂环烷基或-C1-C20烷基,此处一个或多个不直接相邻的C-原子可被第5族或第6族的元素之一所取代,优选为氮、磷、氧或硫,特别优选为氮或氧,和
R7相同或不同,为氢、氧、硫或羟基、氨基甲酰基、氨基、羧基、C1-C20烷羰基、C1-C20烷氧基、C4-C20芳氧基、亚胺基、C1-C20烷亚胺基、C6-C20烷亚胺基、氰基、C1-C20烷基、C6-C20芳基、C5-C20杂芳基、C4-C20环烷基、C4-C20杂环烷基、C7-C20烷芳基、C7-C20芳烷基、C2-C20链烯基、C2-C20α-氧-链烯基、含卤素C1-C20烷基、C6-C20芳基、C7-C20烷芳基、C7-C30芳烷基或C2-C20链烯基,和
R8,R9,R10相同或不同,为氢或-C1-C20含碳的基团,和
e为一自然整数0至40。
在本发明的范围内在含C1-C20的基团中,优选是C1-C20烷基,特别优选是甲基、乙基、正-丙基、异丙基、正-丁基、异丁基、仲丁基、特丁基、正戊基、仲戊基、环戊基、正己基、环己基、正辛基或环辛基,C1-C20-链烯基特别优选是乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、辛烯基或环辛烯基、C1-C20炔烃基,特别优选是乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基,C6-C20芳基,特别优选是苯基、联苯基、萘基或蒽基、C1-C20氟烷基,特别优选是三氟甲基、五氟乙基或2,2,2-三氟乙基、C6-C20芳基特别优选是苯基、联苯基、萘基、蒽基、苯并菲基、[1,1’;3’,1”]三联苯-2’-基、二萘基、或菲基、C6-C20氟芳基、特别优选是四氟苯基或六氟萘基、C1-C20烷氧基,特别优选是甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基或特丁氧基、C6-C20-芳氧基,特别优选是苯氧基、萘氧基、联苯氧基、蒽氧基、菲氧基、C7-C20芳烷基,特别优选是邻-甲苯基、间-甲苯基、对-甲苯基、2,6-二甲苯基、2,6-二-异丙苯基、2,6-二-特丁苯基、邻-特丁苯基、间-特丁苯基、对-特丁苯基、C7-C20烷苯基,特别优选是苄基、乙苯基、丙苯基、二苯甲基、三苯甲基或萘甲基,C7-C20芳氧烷基,特别优选是邻-甲氧苯基、间-苯氧基甲基、对-苯氧基甲基、C12-C20芳氧芳基,特别优选是对-苯氧基苯基、C5-C20杂芳基,特别优选是2-吡啶基、3-吡啶基、4-吡啶基、喹啉基、异喹啉基、吖啶基、苯并喹啉基或苯并异喹啉基、C4-C20杂环烷基,特别优选是呋喃基、苯并呋喃基、2-吡咯烷基、2-吲哚基、3-吲哚基、2,3-二氢吲哚基、C8-C20芳链烯基,特别优选是对-乙烯基苯基、间-乙烯基苯基、对-乙烯基苯基、C8-C20芳炔烃基,特别优选是邻-乙炔苯基、间-乙炔苯基或对-乙炔苯基、C2-C20-含杂原子的基团,特别优选是羰基、苯甲酰基、羟基苯甲酰基、苯甲酰氧基、乙酰基、乙酰氧基或腈基,此处的一个或多个含C1-C20的基团可构成环状体系。
在本发明范围内起架桥作用的含C1-C20基团中优选为C1-C20烷基,特别优选是亚甲基、亚乙基、亚丙基、亚丁基、亚戊基、环亚戊基、亚己基或环亚己基、C1-C20-链烯基,特别优选为乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、C1-C20-炔烃基,特别优选为乙炔基、丙炔基、丁炔基、戊炔基或己炔基、C1-C20芳基,特别优选为邻-亚苯基、间-亚苯基或对-亚苯基、C1-C20-含杂原子基团,特别优选为羰基、羟羰基、羰基氧、氨基甲酰基或酰氨基。
本发明的另外对象是本发明水凝胶的制造和应用。
按本发明含有一聚乙烯醇-星形聚合物的水凝胶的制造,例如可通过下述方法实现:
·含有一聚乙烯醇-星形聚合物和任选其它组份的水溶液经反复冷冻和融解,
·有离子化作用的射线(紫外线、γ-射线)辐照含有一聚乙烯醇-星形聚合物和任选其它组份的水溶液,和
·含有一聚乙烯醇-星形聚合物和任选其它组份的水溶液与有交联作用的试剂,例如戊二醛、乙醛、甲醛、马来酸、草酸、海藻酸、二甲基脲、乙二醛、盐酸、聚丙烯醛、二异氰酸酯和/或硫酸二乙烯酯,在往往还有酸或碱催化剂存在时,进行反应。
所谓其它组份是指:
·常规的聚乙烯醇,
·其它聚合物,例如聚丙烯酸、聚甲基丙烯酸、聚丙烯酸酯、聚甲基丙烯酸酯和聚乙烯基吡咯烷酮,
·微生物
·海藻酸衍生物,例如海藻酸钠,
·盐类,例如碳酸钠、碳酸钾、碳酸钙、碳酸铵、碳酸镁、碳酸氢钠、碳酸氢钾、碳酸氢钙、碳酸氢镁、硫酸钠、硫酸钾、硫酸铵、硫酸镁、磷酸钠、磷酸钾、磷酸铵、磷酸镁、氯化钠、氯化钾、氯化铵、氯化钙、氯化镁和/或氯化铝。
按本发明的水凝胶与源自常规聚合物的水凝胶相比具有较高透明性的特征(对比浊度值:参见例3和4)。
按本发明的水凝胶与常规聚合物相比显示出对水有较高的稳定性,这对于用作包涵固定化生物催化剂时是有优越性的,例如处理废水(对比对水的稳定性:参见例7和8)。
下述混合物产品作为对本发明的阐明,但举例并非是对本发明水凝胶的限制,这些混合物是:
·聚乙烯醇-星形聚合物和水
·聚乙烯醇-星形聚合物,常规聚乙烯醇和水
·聚乙烯醇-星形聚合物,聚丙烯酸和水
·聚乙烯醇-星形聚合物,聚甲基丙烯酸和水
·聚乙烯醇-星形聚合物,聚丙烯酸酯和水
·聚乙烯醇-星形聚合物,聚甲基丙烯酸酯和水
·聚乙烯醇-星形聚合物,聚乙烯基吡咯烷酮和水
·聚乙烯醇-星形聚合物,常规聚乙烯醇、海藻酸钠、氯化钙、甲醛和水
·聚乙烯醇-星形聚合物,常规聚乙烯醇、微生物和水
·聚乙烯醇-星形聚合物,常规聚乙烯醇、氯化钙和水
·聚乙烯醇-星形聚合物,常规聚乙烯醇、氯化钙、微生物和水。
本发明的另外对象是含有一种或多种聚乙烯醇-星形聚合物水凝胶在下述方面的应用:
·在生物医药和药剂领域作为材料,例如作为人造组织或用于创伤处理
·用作制造接触镜片的材料
·作为控制活性物释放的材料
·用作包涵固定化生物催化剂的载体材料,例如用于废水处理
·作为过渡金属催化剂的载体材料,例如钯催化剂
·作为制备活性膜的材料
·作为钻孔液的添加物,特别是基于其可分解性,用于近海作业钻孔冲洗的添加物
·在采油时作为置换剂
·作为水泥的助剂
·作为高粘度液体的添加剂,例如改善石油的流动性能,用于快速输送
·作为化妆品的组分。
通过下述的举例,对本发明进行阐明,但并非是对本发明的限制。
例1按DE10343607制备一聚乙烯醇-星形聚合物
在一1000ml的园底烧瓶中装有167ml1%的甲醇苛性钠溶液,并置于水溶中加热至50℃,在30分钟的时间内往其中滴入含有50g聚醋酸乙烯-星形聚合物的333ml甲醇溶液,加完后再搅拌30分钟,过滤出白色沉淀,用甲醇洗涤至非碱性,在真空中干燥。收率:25.0g。1H-NMR(500MHz,[D6]-DSMO):δ=6.65(s,aromatic H),4.65,4.46,3.89,3.84,3.31,1.44-1.33(4xs,1xm,PVOH)ppm.
例2按DE10356574制备-聚乙烯醇-星形聚合物
132ml(1.43mol)醋酸乙烯、9.0g(70.2mmol)二烯丙基甲缩醛、1.6ml(7.3mmol)亚磷酸三(-2,2,2-三氟乙基)酯和1.25g(3.6mmol)过氧化二苯甲酰(70%,其它为水)置入68ml甲苯中,将此透明无色溶液在70℃时搅拌20小时,用真空油泵除去挥发性成分,将聚醋酸乙烯-星形聚合物溶于200ml的甲醇中,并将该溶液在15分钟内滴入400ml1%NaOH甲醇溶液中,再在50℃时搅拌90分钟,过滤聚乙烯醇,用甲醇洗涤至中性,用真空油泵干燥。收率:14.4g(22%)1H-NMR(500MHz,[D6]-DSMO):δ=5.92-5.87(m),5.24,5.13(2xd),4.66,4.61,4.46,4.22,4.21,4.10,4.09,4.00,3.89,3.84,3.35,3.16,1.43-1.33(13xm)ppm。
例3制备含有聚乙烯醇-星形聚合物的水凝胶
25g聚乙烯醇-星形聚合物(例1)在70°时溶于75ml的脱矿物质的水中,将该溶液置入一浅金属盘(20×20cm)里,用盖子覆盖,并在-30℃时放置12小时,而后使该溶液在12小时内达到室温,再反复进行两次冷冻-融解的过程,所得到的水凝胶为0.25cm厚的膜状物,不透明度(浊度值为百分数):1.3。
例4制备有一线型聚乙烯醇的水凝胶(对比例)
25g聚乙烯醇(Celanese公司的Celvol103)在70°时溶于脱矿物质的水中,将溶液置入一浅金属盘(20×20cm)里,用盖子覆盖,并在-30℃时放置12小时,而后使该溶液在12小时内达到室温,再反复进行两次冷冻-融解的过程,所获得的水凝胶为0.25cm厚的膜状物,不透明度(浊度值为百分数):4.6。
例5制备含有-聚乙烯醇-星形聚合物与线型聚乙烯醇混合物的水凝胶
2g聚乙烯醇-星形聚合物(例2)、2g聚乙烯醇(Celanese公司的Celvol 103)、0.5g海藻酸钠盐和0.15g碳酸氢钠在70℃时溶于50ml水中,冷却至室温后,用一无针头的注射器以大滴形状滴加到经缓慢搅拌的250ml的0.1mol的氯化钙溶液中,此时形成约为3mm大小的球状颗粒,球粒经玻璃滤层小心过滤分离后,加到一含有5g甲醛(37%水溶液)、50g浓硫酸和25g硫酸钠的40℃热溶液中,经1小时后变为结实的球粒过滤分离,并用水洗涤至中性。收率:43g,水凝胶呈球粒状。
例6制备含有一线型聚乙烯醇的水凝胶(对比例)
4g聚乙烯醇(Celanese公司的Celvol 103)、0.5g海藻酸钠盐和0.15g碳酸氢钠在70°时溶于50ml水中,冷却至室温后,用一无针头的注射器以大滴形状滴加到经缓慢搅拌的250ml的0.1mol的氯化钙溶液中,此时形成约为3mm大小的球状颗粒,球粒经玻璃滤层小心过滤分离后,加到一含有5g甲醛(37%水溶液)、50g浓硫酸和25g硫酸钠的40℃热溶液中,经1小时后将变为结实的球粒过滤分离,并用水洗至中性。收率:37g,水凝胶呈球粒状。
例7由例5制取的水凝胶进行磨耗试验
由例5制备的10g水凝胶加到一50ml一次性注射器中,其底部有塑料筛滤网(网眼大小为0.75mm),水凝胶用一塑料筛滤网覆盖,在水凝胶上部空间用玻璃棉填充,该注射器用一橡皮塞塞紧,像皮塞装有一1mm的聚四氟乙烯管,借助泵的作用,经聚四氟乙烯管通过水凝胶导入流动的自来水,水流速度为1ml/min,水流时间为1周。然后将水凝胶从注射器中卸出,并称重,一周后由例5制备的水凝胶重为9.2g。
例8由例6制备的水凝胶进行磨耗试验(对比例)
由例6制备的10g水凝胶加到一50ml的一次性注射器中,其底部有塑料筛滤网(网眼大小为0.75mm),水凝胶用一塑料筛滤网覆盖,在水凝胶上部的空间用玻璃棉填充,该注射器用一橡皮塞塞紧,橡皮塞装有一1mm的聚四氟乙烯管,借助泵的作用,经聚四氟乙烯管通过水凝胶导入流动的自来水,水流速度为1ml/min,水流时间为1周。然后将水凝胶从注射器中卸出,并称重,一周后由例6制备的水凝胶重为8.1g。
Claims (6)
1.含有至少一种聚乙烯醇-星形聚合物的水凝胶。
2.按权利要求1的水凝胶,其特征在于,该水凝胶除聚乙烯醇-星形聚合物以外,还含有其它的聚乙烯醇-星形聚合物。
3.按权利要求1的水凝胶,其特征在于,该水凝胶除聚乙烯醇-星形聚合物以外,还含有选自于聚乙烯醇、聚丙烯酸、聚甲基丙烯酸、聚丙烯酸酯、聚甲基丙烯酸酯和聚乙烯基吡咯烷酮类基团的其它聚合物。
4.按权利要求1的水凝胶,其特征在于,聚乙烯醇-星形聚合物至少是式I,II和III之一的一个化合物
式I 式II 式III
其中
Pol是以一聚乙烯醇为基础的聚合物,特别优选是以聚乙烯醇为基础的均聚和共聚物,尤其特别优选是聚乙烯醇、聚乙烯醇-聚醋酸乙烯共聚物、聚乙烯醇-聚乙烯共聚物、聚乙烯醇-聚氯乙烯-共聚物和聚乙烯醇-聚丙烯酸甲酯-共聚物,和
Z是中心原子和元素周期表中的第13至16族的一个原子,优选是碳、硅、氮、磷、氧或硫,特别优选是碳或硅,和
X1各为相同或不同的一卤素原子,优选是氟、氯、溴或碘,特别优选是氯、溴和碘,和
R1相同或不同,为氢或有一C,-C20的含碳基团,和
R2相同或不同,为在中心原子Z和起始单元[R3-X1]之间一架桥的C1-C20的含碳基团或是硅或氧,和
R3相同或不同,为碳或硅,和
R4相同或不同,为一氢原子或一C1-C20含碳基团,和
R5相同或不同,为氢或一C1-C20含碳基团,
l为一自然整数0,1,2或3,和
m各为相同或不同,为一自然整数0,1,2,3,4和5,和
n各为相同或不同,为一自然整数0,1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19和20,和
o各为相同或不同,为1或2,和
p各为相同或不同,为一自然整数1,2,3,4和5,和
q为一自然整数2,3和4,和
Ar为带有至少4个C-原子的芳族基础构架,所带的一个或多个C原子可被硼、氮或磷所替换,此处优选的芳族或杂芳族基础构架是从苯、联苯、萘、蒽、菲、苯并菲、喹啉、吡啶、联吡啶、哒嗪、嘧啶、吡嗪、三嗪、苯并吡咯、苯并三唑、苯并吡啶、苯并吡嗪烷(Benzopyrazidin)、苯并嘧啶、苯并吡嗪、苯并三嗪、吲嗪、喹嗪、咔唑、吖啶、吩嗪、苯并喹啉、吩嗪,有时可能是它们的取代物所衍生的,和
y为一自然整数0,1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19和20,和
z为一自然整数2,3,4,5,6,7,8,9和10。
Ap为至少一带有3个碳原子的环状非芳族的基础架构,所带碳原子可含有如氮、硼、磷、氧或硫的杂原子,此处优选的脂肪族基础构架是从环烷基类基团,例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基或是从环杂烷基类基团,例如氮丙啶(氮杂环丙烷)、氮杂环丁烷、吡咯烷、哌啶、氮杂卓烷(Azepane)、吖辛因烷(Azocane)、1,3,5-三嗪烷(1,3,5-Triaziman)、1,3,5-三、氧杂环丁烷、呋喃、二氢呋喃、四氢呋喃、吡喃、二氢吡喃、四氢吡喃、庚烷(Oxepan)、Oxocan或从糖类基团,例如α-葡萄糖、β-葡萄糖,衍生的,和
a为一自然整数0,1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19和20,和
b为一自然整数2,3,4,5,6,7,8,9和10,和
c为一自然整数0,1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19和20,
d相同或不同,为0或1。
5.按权利要求1的水凝胶,其特征在于,所用的聚乙烯醇-星形聚合物是以聚乙烯酯共聚物为基础的聚乙烯醇共聚物,它是通过包括下述步骤的工艺方法得到的:
A)在能产生自由基的化合物和往往还有自由基捕获物存在时,乙烯基酯进行自由基溶液聚合或本体聚合,
B)加入具有交联能力的聚链烯基化合物,
C)所生成的聚乙烯酯共聚物往往要进行加工处理和分离,
D)在B)步骤制取的聚乙烯基酯/聚乙烯基酯-聚烯烃-混合物或在C)步骤分离出的聚乙烯基酯-聚烯烃-共聚物用碱皂化而生成聚乙烯醇/聚乙烯醇-聚烯烃-混合物或聚乙烯醇-聚烯烃-共聚物和分离该产品,其特征在于,在B)步骤中加入的聚烯烃化合物是指式IV的化合物:
式IV
其中
R6为C6-C20芳基、C5-C20杂芳基、C4-C20环烷基、C4-C20杂环烷基或C1-C20烷基,此处一个或多个不直接相邻的C-原子可被第5族或第6族的元素之一所取代,优选为氮、磷、氧或硫,特别优选为氮或氧,和
R7相同或不同,为氢、氧、硫或羟基、氨基甲酰基、氨基、羧基、C1-C20烷羰基、C1-C20烷氧基、C6-C20芳氧基、亚胺基、C1-C20烷亚胺基、C6-C20烷亚胺基、氰基、C1-C20烷基、C6-C20芳基、C5-C20杂芳基、C4-C20环烷基、C4-C20杂环烷基、C7-C20烷芳基、C7-C20芳烷基、C2-C20链烯基、C2-C20α-氧-链烯基、含卤素C1-C20烷基、C6-C20芳基、C7-C20烷芳基、C7-C30芳烷基或C2-C20链烯基,和
R8,R9,R10相同或不同,为氢或C1-C20含碳的基团,和
e为一自然整数0至40。
6.按权利要求1至5之一的水凝胶的应用在生物医药和药剂制造领域,特别是用于制备人造组织或创伤处理、制造接触镜片、作为控制活性物释放的载体材料、作为包涵固定化生物催化剂的载体材料,特别是废水处理过程中,作为过渡金属催化剂的载体材料、作为制备活性膜的材料、作为钻孔液的添加物,特别是用于钻孔冲洗、作为采油的置换剂、作为建筑材料的助剂,特别是在分散液和乳液中、作为高粘度液体的添加剂,特别是改善流动性能用于快速运输和作为化妆品的组分。
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CN101955561A (zh) * | 2010-09-16 | 2011-01-26 | 李汝基 | 乙烯醇系聚合物 |
CN102804031A (zh) * | 2009-06-03 | 2012-11-28 | 株式会社实瞳 | 湿润性水凝胶接触镜及其制造方法 |
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CN106279453A (zh) * | 2015-05-28 | 2017-01-04 | 易媛 | 交联的高分子化合物及其制备方法、水凝胶、水基压裂液和用途 |
CN110257031A (zh) * | 2019-06-14 | 2019-09-20 | 中国石油天然气股份有限公司 | 一种油田微颗粒水凝胶调剖堵水剂及其制备方法 |
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US7902128B2 (en) * | 2008-04-29 | 2011-03-08 | Halliburton Energy Services Inc. | Water-in-oil emulsions with hydrogel droplets background |
CN105380662B (zh) * | 2008-07-31 | 2018-06-12 | 希森美康株式会社 | 用于测定活体内成分的方法、装置及收集部件 |
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DE102013019888A1 (de) | 2013-11-28 | 2015-05-28 | Carl Freudenberg Kg | Hydrogelierende Fasern sowie Fasergebilde |
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JPH11510837A (ja) * | 1995-07-28 | 1999-09-21 | フォーカル,インコーポレイテッド | 薬物送達のための制御された放出薬剤および組織処置薬剤としての使用のためのマルチブロック生分解性ヒドロゲル |
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-
2004
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2005
- 2005-04-22 CN CNA2005800164528A patent/CN101090916A/zh active Pending
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- 2005-04-22 BR BRPI0510176-0A patent/BRPI0510176A/pt not_active IP Right Cessation
- 2005-04-22 AT AT05744213T patent/ATE413419T1/de not_active IP Right Cessation
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- 2005-04-22 DE DE502005005891T patent/DE502005005891D1/de not_active Withdrawn - After Issue
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JP2007533810A (ja) | 2007-11-22 |
ATE413419T1 (de) | 2008-11-15 |
US20080112984A1 (en) | 2008-05-15 |
DE102004019504A1 (de) | 2005-11-10 |
MXPA06012292A (es) | 2007-01-31 |
BRPI0510176A (pt) | 2007-10-02 |
EP1737896B1 (de) | 2008-11-05 |
CA2566818A1 (en) | 2005-11-03 |
WO2005103097A1 (de) | 2005-11-03 |
KR20070099413A (ko) | 2007-10-09 |
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Open date: 20071219 |