WO1988000588A1 - Organotin compounds containing fluorine useful for forming fluorine-doped tin oxide coating - Google Patents

Organotin compounds containing fluorine useful for forming fluorine-doped tin oxide coating Download PDF

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Publication number
WO1988000588A1
WO1988000588A1 PCT/US1987/001746 US8701746W WO8800588A1 WO 1988000588 A1 WO1988000588 A1 WO 1988000588A1 US 8701746 W US8701746 W US 8701746W WO 8800588 A1 WO8800588 A1 WO 8800588A1
Authority
WO
WIPO (PCT)
Prior art keywords
fluorine
tin oxide
doped tin
compounds containing
trifluoroacetate
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.)
Ceased
Application number
PCT/US1987/001746
Other languages
English (en)
French (fr)
Inventor
Georg H. Lindner
David Alan Russo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
M&T Chemicals Inc
Original Assignee
M&T Chemicals Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to IN550/CAL/87A priority Critical patent/IN168762B/en
Application filed by M&T Chemicals Inc filed Critical M&T Chemicals Inc
Priority to BR8707749A priority patent/BR8707749A/pt
Priority to AT87905098T priority patent/ATE63918T1/de
Priority to DE8787905098T priority patent/DE3770472D1/de
Priority to KR1019880700299A priority patent/KR900003453B1/ko
Publication of WO1988000588A1 publication Critical patent/WO1988000588A1/en
Priority to DK137088A priority patent/DK167875B1/da
Priority to NO881186A priority patent/NO171068C/no
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/22—Tin compounds
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
    • C23C16/40—Oxides
    • C23C16/407—Oxides of zinc, germanium, cadmium, indium, tin, thallium or bismuth
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/004—Aftersun preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/22—Tin compounds
    • C07F7/2224—Compounds having one or more tin-oxygen linkages

Definitions

  • Organotin compounds containing fluorine which are particularly useful for forming fluorine-doped tin oxide c ings by the chemical vapor deposition method.
  • the compound is monobutyldichlorotin luoroacetate, which is prepared by reaction of monobutyltin trichloride and trifluoroacetic acid.
  • This invention relates to organotin compounds containing fluorine which are use-ful in forming fluorine- doped tin oxide coatings.
  • Plum, et al., in U.S. 4,374,778, discloses flu ⁇ ro- organotin compounds in which the fluorine atom is bonded directly to the tin atom.
  • J. Organomet. Chem. 3972 (1971) describes tri- alkyltin perfluoroalkyl oxides. These references do not disclose an organotin precursor use f ul for chemical vapor deposition particularly from a liquid coating composition. Moreover, the references do not disclose an organotin compound which has a monoalkyl or related substituent and at least one chlorine atom attached directly to the tin atom, and at least one trif luoromethyl-containing constituent.
  • an object of this invention is to provide new and improved organotin compounds which may be used directly to form fluorine-doped tin oxide coatings having a low sheet resistance.
  • Another object herein is to provide such compounds which may be used to prepare fluorine-doped tin oxide coatings by the chemical vapor deposition method.
  • Still another object herein is to prepare monoalkylchlorotin tri fluoracetates and related compounds which can be used advantageously in liquid coating compositions for chemical vapor deposition offluorine-doped tin oxide coatings.
  • organo compounds containing fluorine of the invention have the general formula:
  • Table I summarizes compounds of the invention within the general formula for each case of a,b,c,f,d,e and n in such formula.
  • the reactants used in preparing such compounds also arei given therein.
  • the preferred compounds of the invention include:
  • the compounds of the invention may be prepared as described below General Reactio ss R a SnCl b + 1 (OCOCH 3 ) c + [O (CO) d (CH 2 ) e (C n F 2n+1 ) ] f M + reflux
  • alkyl as used herein includes straight and branched chain alkyl groups which have from one to six carbon atoms.
  • organotin as used herein includes tin tetrachloride.
  • representative organotin reactants used in preparing the compounds of the invention include monobutyltin trichloride, isobutyltin trichloride, methyltin trichloride, dibutyltin dichloride, butyldichlorotin acetate and carbethoxyethyltin trichloride; and tin tetrachloride.
  • the fluoride reactant has a trifluoromethyl group located alpha or beta to a functional group where carbon is bonded to oxygen, selected from carboxylic acid, anhydride, acid halide or alcohol. Accordingly, suitable fluorine reactants include the following:
  • Carboxylic acids trifluoroacetic acid chlorodifluoroacetic acid difluoroacetic acid heptafluorobutyric acid pentafluoropropionic acid 3-trifluoromethylcrotonic acid nonafluoropentanoic acid
  • iponobutyltin trichloride is reacted with a salt of tri- fluoroacetic acid to form butyldichlprptin tri- fluoroacetate.
  • a reaction mixture of monobuutyltin trichloride 200 g., 0.7 mole were heated at 70 C. for 3 hours and allowed to stand overnight at room temperature. The sodium chloride by-product and unreacted sodium salt were filtered. A liquid coating composition of about 12 wt.% monobutyldichlorotin trifluoroacetate and 88 wt% monobutyltin trichloride.
  • a reaction mixture of monophenyldichlorotin hydroxid (9.0 g., 0.03 mole ) and trifluoroacetic acid (3.42 g., 0.03 mole ) was prepared as in Example 1 and refluxed for 2 hours to yield 81% of the desired product.
  • Example 2 The experiment of Example 2 was repeated using the ammonium salt of trifluoroacetic acid with similar results.
  • Example 1B The liquid coating composition of Example 1B was used for preparing fluorine-doped tin oxide coating on glass by chemical vapor deposition. Transparent, haze- free coatings of a thickness of 200 mm were obtained in 2 seconds deposition time at 650oC. in a water- containing air atmosphere. The sheet resistance was about 40 ohms per square; the infrared reflectivity aas greater than 70% at 10 microns, and the visible light tranmission was greater than 70%..

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Metallurgy (AREA)
  • Mechanical Engineering (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Nutrition Science (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Chemical Vapour Deposition (AREA)
  • Inorganic Compounds Of Heavy Metals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Surface Treatment Of Glass (AREA)
  • Catalysts (AREA)
  • Chemically Coating (AREA)
PCT/US1987/001746 1986-07-18 1987-07-17 Organotin compounds containing fluorine useful for forming fluorine-doped tin oxide coating Ceased WO1988000588A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
IN550/CAL/87A IN168762B (https=) 1986-07-18 1987-07-16
BR8707749A BR8707749A (pt) 1986-07-18 1987-07-17 Compostos de organoestanho contendo fluor utilizaveis na formacao de revestimento de oxido de estanho dopado com fluor
AT87905098T ATE63918T1 (de) 1986-07-18 1987-07-17 Fluor enthaltende organozinnverbindungen, die fuer die bildung von fluor dotierte zinnoxid-schichten verwendbar sind.
DE8787905098T DE3770472D1 (de) 1986-07-18 1987-07-17 Fluor enthaltende organozinnverbindungen, die fuer die bildung von fluor dotierte zinnoxid-schichten verwendbar sind.
KR1019880700299A KR900003453B1 (ko) 1986-07-18 1987-07-17 불소처리 산화주석 피막 형성용 불소함유 유기주석 화합물
DK137088A DK167875B1 (da) 1986-07-18 1988-03-11 Organotin(iv)forbindelser indeholdende fluor, der er nyttige til dannelse af fluorbehandlede tinoxidovertraek
NO881186A NO171068C (no) 1986-07-18 1988-03-17 Fluorholdige organotinn-forbindelser som er anvendelige for fluorforsterkede tinnoksydbelegg

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US888,298 1986-07-18
US06/888,298 US4731462A (en) 1986-07-18 1986-07-18 Organotin compounds containing fluorine useful for forming fluorine-doped tin oxide coating

Publications (1)

Publication Number Publication Date
WO1988000588A1 true WO1988000588A1 (en) 1988-01-28

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Family Applications (1)

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PCT/US1987/001746 Ceased WO1988000588A1 (en) 1986-07-18 1987-07-17 Organotin compounds containing fluorine useful for forming fluorine-doped tin oxide coating

Country Status (19)

Country Link
US (1) US4731462A (https=)
EP (1) EP0318486B1 (https=)
JP (1) JPH02500974A (https=)
KR (1) KR900003453B1 (https=)
CN (1) CN1051088C (https=)
AT (1) ATE63918T1 (https=)
AU (1) AU609734B2 (https=)
BR (1) BR8707749A (https=)
CA (1) CA1276160C (https=)
DE (1) DE3770472D1 (https=)
DK (1) DK167875B1 (https=)
EG (1) EG19792A (https=)
ES (1) ES2007080A6 (https=)
IL (1) IL83178A (https=)
IN (1) IN168762B (https=)
NO (1) NO171068C (https=)
TR (1) TR24843A (https=)
WO (1) WO1988000588A1 (https=)
ZA (1) ZA875095B (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0636629A3 (de) * 1993-07-30 1995-04-12 Goldschmidt Ag Th Alkylzinnverbindungen, deren Herstellung und diese enthaltende Mittel zur Bildung elektrisch leitfähiger und IR-reflektierender Schichten auf Oberflächen von Glas, Glaskeramik oder Email.
DE4433206A1 (de) * 1994-09-17 1996-03-21 Goldschmidt Ag Th Verfahren zur pyrolytischen Beschichtung von Glas-, Glaskeramik- und Emailprodukten

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5725904A (en) * 1995-06-02 1998-03-10 Elf Atochem North America, Inc. Liquid methyltin halide compositions
US5698262A (en) * 1996-05-06 1997-12-16 Libbey-Owens-Ford Co. Method for forming tin oxide coating on glass
FR2795745B1 (fr) * 1999-06-30 2001-08-03 Saint Gobain Vitrage Procede de depot d'une couche a base de tungstene et/ou de molybdene sur un substrat verrier, ceramique ou vitroceramique, et substrat ainsi revetu
EP2251911B1 (en) 2002-10-25 2017-11-29 Nakajima Glass Co., Inc. Solar battery module manufacturing method
JP4290194B2 (ja) * 2004-04-27 2009-07-01 中島硝子工業株式会社 太陽電池モジュールの製造方法
US7947374B2 (en) * 2009-02-19 2011-05-24 Guardian Industries Corp. Coated article with sputter-deposited transparent conductive coating capable of surviving harsh environments, and method of making the same
US8097342B2 (en) * 2009-02-19 2012-01-17 Guardian Industries Corp. Coated article with sputter-deposited transparent conductive coating capable of surviving harsh environments, and method of making the same
US20100209730A1 (en) * 2009-02-19 2010-08-19 Guardian Industries Corp., Coated article with sputter-deposited transparent conductive coating for refrigeration/freezer units, and method of making the same
US9625723B2 (en) * 2013-06-25 2017-04-18 Microsoft Technology Licensing, Llc Eye-tracking system using a freeform prism
US10228561B2 (en) * 2013-06-25 2019-03-12 Microsoft Technology Licensing, Llc Eye-tracking system using a freeform prism and gaze-detection light

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1495783A1 (de) * 1964-03-07 1969-04-03 Hoechst Ag Verfahren zur Herstellung von Polyaethylenterephthalat
US3836444A (en) * 1968-10-01 1974-09-17 Inst Francais Du Petrole Process for polymerizing conjugated diolefins using organic compounds of the transition metals as catalysts
US3781315A (en) * 1971-07-09 1973-12-25 Prod Res & Chem Corp Halo alkoxy metal compounds
US3775453A (en) * 1972-03-14 1973-11-27 Schaper Preparation of hexafluoroisopropoxides of aluminum and group iv elements
DE3010077C2 (de) * 1980-03-15 1981-07-30 Vereinigte Glaswerke Gmbh, 5100 Aachen Verfahren zum Aufbringen von mit einem Halogen, vorzugsweise mit Fluor dotierten Zinnoxidschichten auf Glasoberflächen durch Pyrolyse

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Volume 79, No. 10, 10 September 1973, (Columbus, Ohio, US), A.N. SARA et al.: "Chlorotin Carboxylates by Direct Substitution on Tin Tetrachloride", see page 549, Abstract 60994t, & J. Inorg. Nucl. Chem., 1973 35(6), 1827-31 *
Journal of Organometallic Chemistry, Volume 49, 1973, Elsevier Sequoia S.A., (Lausanne, CH), C. SHIOW-CHYN WANG et al.: "Electron Impact Fragmentations of Dimethylchlorotin Carboxylates, Tetramethyl-1,3-bis (Carboxy) Distannoxanes and Tetramethyl-1-1-(Carboxy)-3-Hydroxy-Distannoxanes", pages 417 - 424 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0636629A3 (de) * 1993-07-30 1995-04-12 Goldschmidt Ag Th Alkylzinnverbindungen, deren Herstellung und diese enthaltende Mittel zur Bildung elektrisch leitfähiger und IR-reflektierender Schichten auf Oberflächen von Glas, Glaskeramik oder Email.
DE4433206A1 (de) * 1994-09-17 1996-03-21 Goldschmidt Ag Th Verfahren zur pyrolytischen Beschichtung von Glas-, Glaskeramik- und Emailprodukten

Also Published As

Publication number Publication date
KR900003453B1 (ko) 1990-05-19
AU7783787A (en) 1988-02-10
NO171068B (no) 1992-10-12
BR8707749A (pt) 1989-08-15
IL83178A0 (en) 1987-12-31
EP0318486A1 (en) 1989-06-07
AU609734B2 (en) 1991-05-09
IL83178A (en) 1992-02-16
NO881186D0 (no) 1988-03-17
ATE63918T1 (de) 1991-06-15
JPH02500974A (ja) 1990-04-05
JPH0575756B2 (https=) 1993-10-21
NO881186L (no) 1988-03-17
DK167875B1 (da) 1993-12-27
KR880701724A (ko) 1988-11-04
ZA875095B (en) 1988-01-13
CA1276160C (en) 1990-11-13
US4731462A (en) 1988-03-15
CN1051088C (zh) 2000-04-05
CN87104911A (zh) 1988-05-11
TR24843A (tr) 1992-06-19
EP0318486B1 (en) 1991-05-29
DK137088D0 (da) 1988-03-11
DK137088A (da) 1988-03-11
DE3770472D1 (de) 1991-07-04
ES2007080A6 (es) 1989-06-01
EG19792A (en) 1996-02-29
NO171068C (no) 1993-01-20
IN168762B (https=) 1991-06-01

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