CN1097762A - 含丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-和膦基羧酸的氟化羧酸酯类及其制备方法和用途 - Google Patents
含丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-和膦基羧酸的氟化羧酸酯类及其制备方法和用途 Download PDFInfo
- Publication number
- CN1097762A CN1097762A CN94100612A CN94100612A CN1097762A CN 1097762 A CN1097762 A CN 1097762A CN 94100612 A CN94100612 A CN 94100612A CN 94100612 A CN94100612 A CN 94100612A CN 1097762 A CN1097762 A CN 1097762A
- Authority
- CN
- China
- Prior art keywords
- group
- contain
- carbon atom
- formula
- straight chain
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title claims abstract description 18
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 carboxylic ester class of phosphinocarboxylic acid Chemical class 0.000 title description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 239000005871 repellent Substances 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 15
- MEUIIHOXOWVKNP-UHFFFAOYSA-N phosphanylformic acid Chemical compound OC(P)=O MEUIIHOXOWVKNP-UHFFFAOYSA-N 0.000 claims description 15
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 238000001308 synthesis method Methods 0.000 claims 1
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical class OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000013019 agitation Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000004519 grease Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 239000011449 brick Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- FUVKFLJWBHVMHX-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonamide Chemical compound NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FUVKFLJWBHVMHX-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
- 241000024287 Areas Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/44—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing nitrogen and phosphorus
- D06M13/447—Phosphonates or phosphinates containing nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
- D06M13/298—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Textile Engineering (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Abstract
本发明涉及含有丙烯酸酯和/或甲基丙烯酸酯
基团的膦酰基羧酸的氟化羧酸酯及其作为防水剂或
抗油剂的用途和制备方法。
Description
本发明涉及含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-和膦基羧酸的氟化羧酸酯类及其作为防水剂和/或抗油剂的用途和制备方法。
含有全氟烷基基团的化合物因具有防水和抗油的性能在工业上广泛地用于浸渍剂中(参见Ullmann,Enzyklopadie der technischenChemie,第4版,1976,11卷,644页;及上文第五版,1988,A11卷,373-374页)。典型的应用包括用作浸渍剂,用于使纺织品(参见Ullmann,Enzyklopadie der techmishen Chmie,第4版,1983,23卷,87页)、皮革(参见Ullmann,Enzyklopadie der technischen chemie,第4版,1978,16卷,卷168页)和纸张(参见J.N.MeuBdoerffer和H.Niederprum,Chemikerzeitung 104(1980)45-52)防水并使这些材料抗油。
防护剂的实例如包括醇类和含有全氟基团的丙烯酸酯类,或其聚合物分散体(参见J.N.MeBdoerffer和H. Niederprum,Chemikerzeitung 104(1980)45-52;和Ullmann,Enzyklopadie,第4版,1983,23卷,87页)。其合成路线可参见J.N.MeuBdoerffer和H.Niederprum,Chemikerzeitung 104(1980)45-52。
用作上述氟化表面活性剂起始原料的全氟化化合物在工业上用三种不同路线生产:
a)电化学氟化;
b)全氟烯烃,尤其是四氟乙烯的调聚反应;
c)四氟乙烯的低聚反应。
制备全氟化原料的上述方法在工业规模上是很昂贵的,这就使得所希望的含全氟基团的化合物的造价高。
本发明的目的是提供具有防水和/或抗油性能,且生产方法简单造价低的含氟基团的改性有机化合物。
借助于按照本发明的含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸酯达到了这一目的。
式中
R1是羟基、甲基、乙基或苯基,
RF是含有1-18个碳原子的直链或支化的氟化烷基,或含有1-18个碳原子的氟化的支化或支链的单体醚或聚醚,
RH是含有1-10个碳原子的直链或支化烷基,
Z代表含有1-20个碳原子的直链或支化的链烷三价基团(三价烃基),或是由氨基基团断开的含有1-20个碳原子的直链或支化链烷三价基团,而氨基基团本身可含有C1-C10的烷基基团或芳基基团作为取代基,或是含有1-20个碳原子并带有一个或多个结构为-COR2的取代基的直链或支化链烷三价基团,或是含有1-20个碳原子并带有一个或多个结构为-PO2HR1的取代基的直链或支化链烷三价基团,式中R1的定义同上,
m可为0或1,
n是0或6的整数,
o是0至6的整数,
含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸酯中校好的是其中RF是含有3-10个碳原子直链或支化的氟烷基的那些化合物。
其中RH代表含有1个或2个碳原子的烷基的那些含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸酯是比较好的。
其中n是1或2的那些含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸酯是特别优选的。
其中o是1或2的那些含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸酯是特别优选的。
其中m等于1的那些含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸酯是特别优选的。
例如,特别优选的含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸酯具有如下结构: 下面所列出的基团是特别优选的:RF的例子:CF3-(CF2)2-CF3-(CF2)3-CF3-(CF2)5-CF3-(CF2)6-CF3-(CF2)7-CF3-(CF2)11-C6F5-CF3C6F4-H-(CF2)6-H-(CF2)2-O-CF3-CHF-CF2-O-CF3-CF2-CF2-O-CF(CF3)-CF3-CF2-[CF2-O-CF(CF3)]2-CF3-CF2-[CF2-O-CF(CF3)]3-Z的例子:
按照本发明的含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸酯可利用相应的膦酰基-或膦基羧酸或它们的盐类与含有氟基团的醇和有羟基官能的丙烯酸或甲基丙烯酸衍生物的酯化反应通过多级合成制备:其中
R1、R、RF、RH、Y、Z、m、n和o的定义同上,
A是氢阳离子、铵阳离子或一价或多价金属阳离子,
X是对应于阳离子A电荷的一个整数。
本发明也涉及按照本发明的含有丙烯酸酯和/或甲基丙烯酸酯的膦酰基-或膦基羧酸的氟化羧酸酯作为防水剂和/或抗油剂的用途。
由于按照本发明的化合物具有防水性和抗油性,所以这些化合物在各种应用领域中可用作浸渍剂,从而本发明的这些化合物本身可以施用或例如以聚合物分散体的形式施用。
例如,按照本发明的化合物可以用在天然纤维和合成纤维(如用于纺织品、地毯或遮蓬)上,用来防水、防脂、防油和/或防尘。
按照本发明的化合物也可用在纸张和卡片纸板(如包装材料或羊毛状物)上,用来防水、防脂、防油和/或防尘。
此外,按照本发明的化合物可以用在皮革(如用于室内装饰、鞋或衣服)上,用来防水、防脂、防油和/或防尘。
按照本发明的化合物也可用在陶瓷(如砖瓦)、天然或人造石块(如砂石)、木材(如表面的木制包层)和塑料(如聚酯)等材料上,作为防水、防脂、防油、防尘、防藻类生长和/或耐气候的浸渍层。
本发明将用下列实例加以更详细的说明。
实施例1
在装有搅拌器和聚水器的三颈烧瓶中将N-(2-羟乙基)-N-甲基-全氟辛基氨磺酰(0.4摩尔/223克)溶于150毫升4-甲基-戊-2-酮中,并加入0.5毫升浓硫酸。将该溶液加热到约116℃。然后缓慢加入溶于54克水中的2-膦酰基丁炕-1,2,4-三羧酸(0.2摩尔/54克)。添加完毕之后,使反应混合物在搅拌下回流直至全部水量(61.2毫升)蒸出为止。
然后缓慢加入丙烯酸羟乙基酯(0.2摩尔/23.2克),接着在搅拌下回流直至全部水量(3.6毫升)从反应混合物中蒸出为止。
反应完毕后,在70℃和70毫巴条件下将溶剂蒸出,并将所得产品彻底干燥。产品为2-膦酰基-丁烷-1,2,4-三羧酸与2个当量的N-(2-羟乙基)-N-甲基-全氟辛基氨磺酰和1个当量的丙烯酸羟乙基酯的三酯化产物,产量277克(95.8%理论产率)。
实施例2
在装有搅拌器和聚水器的三颈烧瓶中将N-(2-羟乙基)-N-甲基-全氟丁基氨磺酰(0.2摩尔/71克)溶于150毫升4-甲基戊-2-酮中,并加入0.5毫升浓硫酸。将该溶液加热至116℃。然后缓慢加入溶于54克水中的2-膦酰基丁烷-1,2,4-三羧酸(0.2摩尔/54克)。添加完毕之后,使反应混合物在搅拌下回流直至全部水量(57.6毫升)蒸出为止。
然后缓慢加入溶于50毫升4-甲基戊-2-酮的十八(碳)醇(0.2摩尔/54克),接着在搅拌下回流直至全部水量(3.6毫升)从反应混合物中蒸出为止。
然后缓慢加入甲基丙烯酸羟乙基酯(0.2摩尔/26克),接着在搅拌下回流直至全部水量(3.6毫升)从反应混合物中蒸出为止。
反应完毕后,在70℃和70毫巴条件下将溶剂蒸出,并将所得产品彻底干燥。产品为2-膦酰基-丁烷-1,2,4-三羧酸与各为1当量的N-(2-羟乙基)-N-甲基-全氟丁基氨磺酰、十八(碳)醇和甲基丙烯酸羟乙基酯的三酯化产物,产量180克(92.5%理论产率)。
Claims (8)
1.式(I)所示的含有丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸酯及其盐类:
式中
R1是羟基、甲基、乙基或苯基,
RF是含有1-18个碳原子的直链或支化的氟化烷基,或含有1-18个碳原子的氟化的支化或支链的单体醚或聚醚,
RH是含有1-10个碳原子的直链或支化烷基,
Z代表含有1-20个碳原子的直链或支化的链烷三价基团(三价烃基),或是由氨基基团断开的含有1-20个碳原子的直链或支化链烷三价基团,而氨基基团本身可含有C1-C10的烷基基团或芳基基团作为取代基,或是含有1-20个碳原子并带有一个或多个结构为-COR2的取代基的直链或支化链烷三价基团,或是含有1-20个碳原子并带有一个或多个结构为-PO2HR1的取代基的直链或支化链烷三价基团,式中R1的定义同上,
m可为0或1,
n是0或6的整数,
o是0至6的整数,
2.按照权利要求1的化合物,其中RF是含有3-10个碳原子的直链或支化的氟烷基。
3.按照权利要求1的化合物,其中RH代表含有1个或2个碳原子的烷基。
4.按照权利要求1的化合物,其中n是1或2。
5.按照权利要求1的化合物,其中o是1或2。
6.按照权利要求1的化合物,其中m是1。
8.含有如权利要求1所提出的含丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基-或膦基羧酸的氟化羧酸的酯的防水剂或抗油剂。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4300799.6 | 1993-01-14 | ||
DE4300799A DE4300799C2 (de) | 1993-01-14 | 1993-01-14 | Acrylat- und/oder methacrylatgruppenhaltige fluorierte Carbonsäureester von Phosphono- und Phosphinocarbonsäuren, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1097762A true CN1097762A (zh) | 1995-01-25 |
CN1042635C CN1042635C (zh) | 1999-03-24 |
Family
ID=6478181
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN94100612A Expired - Fee Related CN1042635C (zh) | 1993-01-14 | 1994-01-14 | 含丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基羧酸的氟化羧酸酯类及其制备方法和用途 |
Country Status (9)
Country | Link |
---|---|
US (1) | US5414102A (zh) |
EP (1) | EP0606833B1 (zh) |
JP (1) | JP3310438B2 (zh) |
KR (1) | KR940018391A (zh) |
CN (1) | CN1042635C (zh) |
CA (1) | CA2113238A1 (zh) |
DE (2) | DE4300799C2 (zh) |
ES (1) | ES2110123T3 (zh) |
TW (1) | TW280830B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102311455A (zh) * | 2011-05-19 | 2012-01-11 | 张春华 | 可辐射固化的含膦酸基的多官能(甲基)丙烯酸酯的组合物及其制备方法 |
CN103695578A (zh) * | 2013-12-30 | 2014-04-02 | 青昊环保科技(上海)有限公司 | 一种皮革防水养护剂及其制备方法 |
CN116063207A (zh) * | 2022-12-22 | 2023-05-05 | 浙江大学 | 含n-氧化三级胺基团的双亲性脂质、脂质体递药系统及应用 |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6646088B2 (en) | 2000-08-16 | 2003-11-11 | 3M Innovative Properties Company | Urethane-based stain-release coatings |
US6753380B2 (en) | 2001-03-09 | 2004-06-22 | 3M Innovative Properties Company | Water-and oil-repellency imparting ester oligomers comprising perfluoroalkyl moieties |
US6803109B2 (en) | 2001-03-09 | 2004-10-12 | 3M Innovative Properties Company | Water-and oil-repellency imparting urethane oligomers comprising perfluoroalkyl moieties |
US6890360B2 (en) | 2001-12-17 | 2005-05-10 | 3M Innovative Properties Company | Fluorochemical urethane composition for treatment of fibrous substrates |
US20040147188A1 (en) * | 2003-01-28 | 2004-07-29 | 3M Innovative Properties Company | Fluorochemical urethane composition for treatment of fibrous substrates |
US20070014927A1 (en) * | 2005-07-15 | 2007-01-18 | Buckanin Richard S | Fluorochemical urethane composition for treatment of fibrous substrates |
CN114805690A (zh) * | 2006-06-15 | 2022-07-29 | 陶氏环球技术有限责任公司 | 官能化烯烃共聚体、组合物和由其制成的制品及其制法 |
EP2155830A1 (en) * | 2007-05-23 | 2010-02-24 | 3M Innovative Properties Company | Aqueous compositions of fluorinated surfactants and methods of using the same |
JP5453250B2 (ja) * | 2007-06-06 | 2014-03-26 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化エーテル組成物及びフッ素化エーテル組成物の使用方法 |
JP2010530014A (ja) * | 2007-06-06 | 2010-09-02 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化組成物及びそれから製造される表面処理 |
JP2010530445A (ja) | 2007-06-08 | 2010-09-09 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロアルキル含有エステルオリゴマーとポリジカルボジイミド(類)とのブレンド |
WO2008154414A2 (en) * | 2007-06-08 | 2008-12-18 | 3M Innovative Properties Company | Water- and oil-repellency imparting ester oligomers comprising perfluoroalkyl moieties |
BRPI0915955A2 (pt) * | 2008-07-18 | 2019-02-26 | 3M Innovative Proferties Company | compostos fluorados de éter e métodos para uso dos mesmos |
EP2358779A4 (en) * | 2008-11-25 | 2012-05-09 | 3M Innovative Properties Co | Fluorinated ethurethenes and methods for their use |
CN102317403A (zh) | 2008-12-18 | 2012-01-11 | 3M创新有限公司 | 使含烃地层与氟化醚组合物接触的方法 |
MX2011006673A (es) | 2008-12-18 | 2011-07-20 | 3M Innovative Properties Co | Metodo para poner en contacto formaciones que contienen hidrocarburos con posiciones de fosfatos y fosfonatos fluorados. |
US8859098B2 (en) * | 2012-05-18 | 2014-10-14 | Lord Corporation | Acrylic adhesion promoters |
WO2016099952A1 (en) | 2014-12-18 | 2016-06-23 | 3M Innovative Properties Company | Fluorinated polymers comprising phosphonic moieties |
CN105986344B (zh) * | 2015-02-02 | 2019-02-15 | 福建省泉州海丝船舶评估咨询有限公司 | 一种防水透气棕丝面料的生产方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2424243A1 (de) * | 1974-05-18 | 1975-11-27 | Bayer Ag | Perfluoralkansulfonamidoalkanphosphonsaeure- bzw. -phosphinsaeurederivate |
DE2439281A1 (de) * | 1974-08-16 | 1976-02-26 | Henkel & Cie Gmbh | Beta-trifluormethyl-beta-phosphonobuttersaeure und derivate |
US4602092A (en) * | 1983-09-19 | 1986-07-22 | E. R. Squibb & Sons, Inc. | Method for making phosphinic acid intermediates |
DE3605800A1 (de) * | 1986-02-22 | 1987-08-27 | Bayer Ag | 2-phosphonobutan-1,2,4-tricarbonsaeurederivate als emulgatoren |
-
1993
- 1993-01-14 DE DE4300799A patent/DE4300799C2/de not_active Expired - Fee Related
- 1993-12-17 TW TW082110694A patent/TW280830B/zh active
- 1993-12-27 US US08/172,751 patent/US5414102A/en not_active Expired - Fee Related
-
1994
- 1994-01-03 ES ES94100005T patent/ES2110123T3/es not_active Expired - Lifetime
- 1994-01-03 EP EP94100005A patent/EP0606833B1/de not_active Expired - Lifetime
- 1994-01-03 DE DE59404795T patent/DE59404795D1/de not_active Expired - Fee Related
- 1994-01-10 JP JP01205494A patent/JP3310438B2/ja not_active Expired - Fee Related
- 1994-01-11 CA CA002113238A patent/CA2113238A1/en not_active Abandoned
- 1994-01-13 KR KR1019940000457A patent/KR940018391A/ko not_active IP Right Cessation
- 1994-01-14 CN CN94100612A patent/CN1042635C/zh not_active Expired - Fee Related
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102311455A (zh) * | 2011-05-19 | 2012-01-11 | 张春华 | 可辐射固化的含膦酸基的多官能(甲基)丙烯酸酯的组合物及其制备方法 |
CN103695578A (zh) * | 2013-12-30 | 2014-04-02 | 青昊环保科技(上海)有限公司 | 一种皮革防水养护剂及其制备方法 |
CN116063207A (zh) * | 2022-12-22 | 2023-05-05 | 浙江大学 | 含n-氧化三级胺基团的双亲性脂质、脂质体递药系统及应用 |
Also Published As
Publication number | Publication date |
---|---|
TW280830B (zh) | 1996-07-11 |
DE59404795D1 (de) | 1998-01-29 |
JPH06279468A (ja) | 1994-10-04 |
US5414102A (en) | 1995-05-09 |
JP3310438B2 (ja) | 2002-08-05 |
ES2110123T3 (es) | 1998-02-01 |
DE4300799C2 (de) | 1996-09-19 |
EP0606833B1 (de) | 1997-12-17 |
KR940018391A (ko) | 1994-08-16 |
CA2113238A1 (en) | 1994-07-15 |
CN1042635C (zh) | 1999-03-24 |
EP0606833A1 (de) | 1994-07-20 |
DE4300799A1 (de) | 1994-07-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1042635C (zh) | 含丙烯酸酯和/或甲基丙烯酸酯基团的膦酰基羧酸的氟化羧酸酯类及其制备方法和用途 | |
CN1042634C (zh) | 含羟基和/或巯基基团的膦酰基羧酸的氟化羧酸酯类及其制备方法和用途 | |
US3979469A (en) | Polyfluoroalkyl iodides, process for their manufacture, and their use | |
FR2579211A1 (fr) | Copolymeres fluores et leur application au traitement hydrophobe et oleophobe de substrats divers | |
SU514569A3 (ru) | Способ получени производных пиридазина | |
AU6975596A (en) | Coatings containing fluorinated esters | |
US4739103A (en) | Perfluorocycloalkane carbonyl fluorides and their derivatives | |
CN1041093C (zh) | 膦酰基羧酸和膦基羧酸的氟化羧酸酯其制备方法和用途 | |
KR920701103A (ko) | 개선된 비닐에테르 제조방법 | |
DE3928990A1 (de) | Verfahren zur herstellung von (alpha)-fluoroacrylsaeurederivaten | |
EP0744394B1 (de) | Fluoralkenylgruppen enthaltende (Meth-)Acrylate, deren Herstellung und Verwendung | |
CA1326042C (en) | Esters of arylbisperfluoroalkylcarbinols, and a process for the preparation of these compounds and the underlying arylbisperfluoroalkylcarbinols | |
EP0214351B1 (fr) | Composés organophosphorés, un procédé pour leur préparation et compositions polymères ignifigées au moyen desdits composés | |
DE1935630C3 (de) | Neue Phosphorsäurehalogenide und Verfahren zu ihrer Herstellung | |
US6080885A (en) | Process for preparing a phosphonium salt compound having an acryl group | |
US20070123731A1 (en) | Process for preparing fluorinated alkyl carboxylate esters | |
EP0173197B1 (de) | Ungesättigte Diester von Thia-Alkandiolen | |
DE4242147A1 (zh) | ||
JP2829309B2 (ja) | 含フッ素エステル | |
JPH0796536B2 (ja) | 光学活性なβ−アミノ酸誘導体 | |
JPS557832A (en) | Preparation of fibrous zr-containing phosphoric acid compound | |
GB2090835A (en) | Chloroformates of alkyl esters of c-alkyl-or c-haloalkyl tartronic acids and process for their preparation | |
DE1568991B2 (de) | Verfahren zur Herstellung von fluorhaltigen Methacrylsäureestem | |
RU93034933A (ru) | Способ получения бис-2,3-дибромпропилового эфира метилфосфоновой кислоты |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |