KR940018391A - 아크릴레이트 및(또는) 메타크릴레이트기를 함유한 포스포노- 및 (또는) 포스피노카르복실산의 플루오르화 카르복실산 에스테르, 그의 제조 방법 및 용도 - Google Patents
아크릴레이트 및(또는) 메타크릴레이트기를 함유한 포스포노- 및 (또는) 포스피노카르복실산의 플루오르화 카르복실산 에스테르, 그의 제조 방법 및 용도 Download PDFInfo
- Publication number
- KR940018391A KR940018391A KR1019940000457A KR19940000457A KR940018391A KR 940018391 A KR940018391 A KR 940018391A KR 1019940000457 A KR1019940000457 A KR 1019940000457A KR 19940000457 A KR19940000457 A KR 19940000457A KR 940018391 A KR940018391 A KR 940018391A
- Authority
- KR
- South Korea
- Prior art keywords
- radical
- straight
- carbon atoms
- phosphono
- group
- Prior art date
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title claims abstract 6
- MEUIIHOXOWVKNP-UHFFFAOYSA-N phosphanylformic acid Chemical class OC(P)=O MEUIIHOXOWVKNP-UHFFFAOYSA-N 0.000 title claims abstract 6
- 150000001733 carboxylic acid esters Chemical class 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 title claims 2
- 239000003795 chemical substances by application Substances 0.000 claims abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims abstract 2
- 230000002940 repellent Effects 0.000 claims abstract 2
- 239000005871 repellent Substances 0.000 claims abstract 2
- 238000004078 waterproofing Methods 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 5
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- -1 carboxylic acid carboxylic acid ester Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 238000007040 multi-step synthesis reaction Methods 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (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
본 발명은 아크릴레이트 및(또는) 메타크릴레이트기를 함유한 포스포노- 및 포스피노카르복실산의 플루오르화 카르복실산 에스테르, 그의 방수제 또는 오일 반발제로서의 용도 및 제조 방법에 관한 것이다.
본 발명의 목적은 방수성 또는 오일 반발성을 가지고 간단하게 저렴하게 생산될 수 있는 플루오르기를 함유한 개질된 유기 화합물을 제공하는 것이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 하기 일반식 (Ⅰ)의 아클릴레이트 및(또는) 메타크릴레이트기를 함유한 포스포노- 및 포스피노카르복실산의 플루오르화 카르복실산 에스테르 또는 그의 염상기 식 중, R1은 히드록실기, 메틸기, 에틸기 또는 페닐 라디칼이고, RF는 탄소수 1 내지 18의 직쇄 또는 분지내 플루오르알킬 라디칼 또는 탄소수 1 내지 18의 플루오르화 직쇄 또는 분지쇄 단량체 에테르 또는 폴리에테르이고, RH는 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬 라디칼이고, R은의 아크릴레이트기 또는의 메타크릴레이트기이고, Y는또는기를 나타내고, Z는 탄소수 1 내지 20의 직쇄 또는 분지쇄 알칸트리일 라디칼 (3가 탄화수소 라디칼) 또는 치환기로서 C1내지 C10알킬기 또는 아릴기를 함유할 수 있는 아미노기가 개입된, 탄소수 1 내지 20의 직쇄 또는 분지쇄 알칸트리일 라디칼 또는 하나 이상의 식 -COR2[식 중, R2는 히드록실 라디칼 또는 식(식 중, m은 0 또는 1이고, 0내지 6의 정수이고, RH, RF및 Y는 상기와 동일함)의 라디칼 또는 식 O-(CH2)0-R(식 중, o는 0 내지 6의 정수이고, RH, RF및 Y는 상기와 동일함)의 라디칼 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄알콕시 라디칼을 나타냄]치환기를 갖는 탄소수 1 내지 20의 직쇄 또는 분지쇄 알칸트리일 라디칼 또는 하나 이상의 식 -PO2HR1(여기서 R1은 상기와 동일함)의 치환기를 갖는 타소수 1 내지 20의 직쇄 또는 분지쇄 알칸트리일 라디칼을 나타내고, m은 0 또는 1이고, 0내지 6의 정수이고, o은 0내지 6의 정수이다.
- 제 1 항에 있어서, RF가 탄소수 3 내지 10의 직쇄 또는 분지쇄 플루오르알킬 라디칼인 화합물.
- 제 1 항에 있어서, RH가 탄소수 1 또는 2의 알킬 리디칼을 나타내는 화합물.
- 제 1 항에 있어서, n이 1 또는 2 인 화합물.
- 제 1 항에 있어서, o가 1 또는 2인 화합물.
- 제 1 항에 있어서, m이 1인 화합물.
- 다단계 합성 즉, 제 1 단계로 하기 일반식(Ⅱ)의 포스포노- 또는 포스피노카르복실산 또는 그의 염을 하기 일반식(Ⅲ)의 플루오르기를 함유한 알콜로 에스테르화시키고, 후속 단계로 하기 일반식(Ⅳ)의 히드록시관능기 아크릴 또는 메타크릴산 유도체와 반응시키는 것으로 이루어진 제 1 항에 따른 아크릴레이트 및(또는) 메타크릴레이트기를 함유한 포스포노- 또는 포스피노카르복실산의 플루오르화 카르복실산 에스테르의 제조 방법.상기 식 중, A는 수소 양이온, 암모늄 양이온 또는 1가 또는 다가의 금속 양이온이고, x는 양이온 A의 전하에 대응하는 정수이고, R1, R, RF, RH, o, Y, Z, m 및 n은 제 1 항에서 정의한 바와 같다.
- 제 1 항에 따른 아크릴레이트 및(또는) 메타크릴레이트기를 함유한 포스포노- 또는 포스피노카르복실산의 카르복실산 카르복실산 에스테르로 이루어진 방수제 또는 오일 반발제.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| DEP4300799.6 | 1993-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR940018391A true KR940018391A (ko) | 1994-08-16 |
Family
ID=6478181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940000457A KR940018391A (ko) | 1993-01-14 | 1994-01-13 | 아크릴레이트 및(또는) 메타크릴레이트기를 함유한 포스포노- 및 (또는) 포스피노카르복실산의 플루오르화 카르복실산 에스테르, 그의 제조 방법 및 용도 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5414102A (ko) |
| EP (1) | EP0606833B1 (ko) |
| JP (1) | JP3310438B2 (ko) |
| KR (1) | KR940018391A (ko) |
| CN (1) | CN1042635C (ko) |
| CA (1) | CA2113238A1 (ko) |
| DE (2) | DE4300799C2 (ko) |
| ES (1) | ES2110123T3 (ko) |
| TW (1) | TW280830B (ko) |
Families Citing this family (22)
| 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 |
| KR101513733B1 (ko) * | 2006-06-15 | 2015-04-21 | 다우 글로벌 테크놀로지스 엘엘씨 | 관능화된 올레핀 혼성중합체, 조성물 및 이로부터 제조된 제품, 및 이의 제조 방법 |
| WO2008147796A1 (en) * | 2007-05-23 | 2008-12-04 | 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 |
| EP2167550B1 (en) | 2007-06-06 | 2012-05-23 | 3M Innovative Properties Company | Fluorinated compositions and surface treatments made therefrom |
| WO2008154414A2 (en) * | 2007-06-08 | 2008-12-18 | 3M Innovative Properties Company | Water- and oil-repellency imparting ester oligomers comprising perfluoroalkyl moieties |
| 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 |
| JP2011528659A (ja) * | 2008-07-18 | 2011-11-24 | スリーエム イノベイティブ プロパティズ カンパニー | フッ素化エーテル化合物及びその使用方法 |
| WO2010062843A1 (en) * | 2008-11-25 | 2010-06-03 | 3M Innovative Properties Company | Fluorinated ether urethanes and methods of using the same |
| WO2010080473A1 (en) | 2008-12-18 | 2010-07-15 | 3M Innovative Properties Company | Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions |
| CN102333841B (zh) | 2008-12-18 | 2014-11-26 | 3M创新有限公司 | 使含烃地层与氟化磷酸酯和膦酸酯组合物接触的方法 |
| 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 |
| US8859098B2 (en) * | 2012-05-18 | 2014-10-14 | Lord Corporation | Acrylic adhesion promoters |
| CN103695578B (zh) * | 2013-12-30 | 2017-01-11 | 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 |
| 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 |
| 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 |
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 DE DE59404795T patent/DE59404795D1/de not_active Expired - Fee Related
- 1994-01-03 EP EP94100005A patent/EP0606833B1/de not_active Expired - Lifetime
- 1994-01-03 ES ES94100005T patent/ES2110123T3/es not_active Expired - Lifetime
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| US5414102A (en) | 1995-05-09 |
| CA2113238A1 (en) | 1994-07-15 |
| DE59404795D1 (de) | 1998-01-29 |
| EP0606833A1 (de) | 1994-07-20 |
| JPH06279468A (ja) | 1994-10-04 |
| CN1097762A (zh) | 1995-01-25 |
| CN1042635C (zh) | 1999-03-24 |
| DE4300799A1 (de) | 1994-07-21 |
| DE4300799C2 (de) | 1996-09-19 |
| EP0606833B1 (de) | 1997-12-17 |
| TW280830B (ko) | 1996-07-11 |
| ES2110123T3 (es) | 1998-02-01 |
| JP3310438B2 (ja) | 2002-08-05 |
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