US3806530A - Organo tin derivatives of tetrafluoro-cyclo-butyl acrylic acids - Google Patents

Organo tin derivatives of tetrafluoro-cyclo-butyl acrylic acids Download PDF

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Publication number
US3806530A
US3806530A US00269867A US26986772A US3806530A US 3806530 A US3806530 A US 3806530A US 00269867 A US00269867 A US 00269867A US 26986772 A US26986772 A US 26986772A US 3806530 A US3806530 A US 3806530A
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United States
Prior art keywords
tin
textiles
compounds
formula
organic compounds
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Expired - Lifetime
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US00269867A
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English (en)
Inventor
W Dittmar
C Dorfelt
K Fischer
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Hoechst AG
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Hoechst AG
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/22Tin compounds
    • C07F7/2224Compounds having one or more tin-oxygen linkages

Definitions

  • the present invention relates to the antimicrobial finishing of textiles.
  • R R R and R 4 may stand above all for alkyl radicals having 1 to 8 carbon atoms, phenyl radicals or phenyl radicals substituted by lower alkyl radicals; R R and R preferably represent butyl or phenyl radicals and R is a methyl, ethyl, butyl, propyl or phenyl radical.
  • the present invention relates to tin-organic compounds of the general Formula I wherein R R R and R are identical or different and represent alkyl radicals having 1 to 8 carbon atoms, phenyl radicals or phenyl radicals substituted by lower alkyl radicals and R represents hydrogen or the methyl group.
  • Tributyltin-B-tetr afluorcyclobutylacrylate
  • Tributyltin- 3-methyl-tetrafiuorocyclobutylacrylate Triphenyltin-B-methyl-tetrafiuorocyclobutylacrylate, Tributyltin-fl-tetrafluorocyclobutylmethacrylate, Tributyltin-B-methyl-tetrafluorocyclobutylmethacrylate, Triphenyltin-fl-tetrafiuorocyclobutylmethacrylate, Triphenyltin-fi-methyl-tetrafiuorocyclobutylmethacrylate.
  • the compounds of the Formula I have the surprising advantage that they provide on synthetic fibres such as polyamide and polyacrylonitrile fibres, anti microbial effects fast to washing. On the cellulose fibre textiles even 'boilproof finishes may be prepared.
  • a further advantage is that these compounds do not lead to a. yellowing of the textile material. As compared with many antimicrobial agents, they do not cause any additional soiling, for example on textile floor covering.
  • the textiles to be antimicrobially finished may consist of natural fibres such as cellulose fibres, wool, silk or synthetic fibres, as for example polyamide, polyacrylonitrile, polyester fibres, polyvinyl chloride-elastomeric fibres, inorganic fibres, asbestos and glass fibres and mixtures of such fibres, as
  • polyester fibres/cotton polyester fibres/spun rayon, polyacrylonitrile fibres/spun rayon,
  • polyester fibres/linen polyester fibres/wool or polyamide fibres/ cotton etc.
  • the preparation of the compounds of the Formula I by reacting bis-organic tin oxides of the Formula II, for example bis-tributyl tin oxide, with carboxylic acids of the Formula III, for example fi-tetrafluoro-cyclobutyl acrylic acid or methyl-tetrafluoro-cyclobutyl acrylic acid may be carried out according to known processes in a suitable organic solvent such as benzene, toluene and xylene.
  • the reaction proceeds at elevated temperature, expediently at the boiling temperature of the solvent under reflux, whereby according to the reaction desired, about 2 mols of the carboxylic acid of the Formula III per mol of the bis-organic tin oxide of the Formula II are used.
  • the water formed during condensation was eliminated together with the solvent by azeotropic distillation.
  • the substance left after distilling off the solvent may be used, if desired, directly, without any further purification, for the antimicrobially finishing according to the invention.
  • the tin-organic compounds of the Formula I are soluble in many organic solvents.
  • Particularly suitable solvents with regard to the textile application of these compounds are lower aliphatic alcohols, especially those having 1 to 4 carbon atoms.
  • they When being applied onto textiles, they may therefore be applied from organic solvents, from mixtures of solvent and water and at pH-values above 7 from aqueous solutions or emulsions, for example those consisting of chloroor fluorohydrcarbons with water or alcohol.
  • the tin-organic compounds of. the Formula I may be used as such and together with other finishing and binding agents. It is also possible to apply the tin-organic compounds together with. optical brighteners or antistatically effective agents.
  • the tin-organic compounds are expediently applied onto the textile material with crease resistant finishing agents. In this processespecially in the case of cross-linking under dry conditions-good boilproof .fungistatic effects can be achieved.
  • the tin-organic compounds may also be used in the known cross-linking processes of textiles in the presence of more or less amounts of water.
  • tin-organic compounds together with finishing agents which are cross-linking in an alkaline medium.
  • the tinorganic compounds may also be used in the dyeing of textiles and may be added for example to the dyestuff bath or printing paste. By this way, antimicrobial effects are simultaneously obtained with the dyeing or printing.
  • a special advantage is the application of the tin-organic compounds together with dyestuffs which can be fixed in an alkaline medium. It is furthermore possible to apply the tin-organic compounds onto the textile material together with hydrophobing, oleophobing and flame-proof finishing agents.
  • tin-organic compounds of the Formula I may be applied onto the good to be finished in any manner desired, for example by padding, slop padding, spraying,
  • the textiles treated with the solutions or dispersions of the tin-organic compounds are dried at room temperature or elevated temperature and expediently heated for about 1 second to 5 minutes up to high temperatures.
  • the choice of the temperature depends on the heating time and on the textile material. There are generally used temperatures in the range of about to 220 C. It has turned out advantageous to subject the textiles treated with the tin-organic compounds of the Formula I and dried, with solutions of diluted alkalis or to apply the compounds of the Formula I to textiles pretreated with alkalis and alkaline reaction.
  • tin-organic compounds according to the invention are also possible to incorporate into pastes, pigment mixtures and the like for coating purposes.
  • plastic disper sions such as polyacrylate, polyurethane, butadiene-co polymer, polyvinylacetate dispersions or natural latex, is particularly important, if floor covering, for example car pets, needle felts, mats or fleeces shall be finished fun gistatically and bacteriostatically.
  • the squeezing off effect was 50% by weight
  • the fabric samples were dried at 100 C. and fixed for one minute at 150 C,
  • the finishes prepared with the solutions A and B have excellent fungistatic effects against dermatomycetes and soil fungi and yeast.
  • the squeezing off effect was 50% by weighti After pad-dyeing the fabric was dried and fixed by heat ing for one minute to 180 C, The textiles finished with the solutions A to C have an excellent fungistatic and a. bacteriostatic effect,
  • solvent there is used a mixture of 3 parts by volume of isopropanol and 1 part by volume of water;
  • R R R and R are identical or different and a 5 represent alkyl radicals having 1 to 8 carbon atoms, phenyl DANIEL WYMAN Pnmary Exammer radicals or phenyl radicals substituted by lower alkyl' A P. DEMERS, Assistant Examiner radicals and R represents hydrogen or the methyl group 10 2.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US00269867A 1971-07-09 1972-07-07 Organo tin derivatives of tetrafluoro-cyclo-butyl acrylic acids Expired - Lifetime US3806530A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2134358A DE2134358A1 (de) 1971-07-09 1971-07-09 Antimikrobielle ausruestung von textilien

Publications (1)

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US3806530A true US3806530A (en) 1974-04-23

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US00269867A Expired - Lifetime US3806530A (en) 1971-07-09 1972-07-07 Organo tin derivatives of tetrafluoro-cyclo-butyl acrylic acids

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US (1) US3806530A (https=)
DE (1) DE2134358A1 (https=)
FR (1) FR2145559A1 (https=)
GB (1) GB1399748A (https=)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4082709A (en) * 1974-01-31 1978-04-04 The United States Of America As Represented By The Secretary Of The Navy Low leaching antifouling organometallic polyesters
US4499022A (en) * 1981-07-03 1985-02-12 Etat Francais Organometallic telomers, methods of preparation and biocidal compositions obtained
US5043463A (en) * 1990-08-17 1991-08-27 Florida Atlantic University Novel compounds for the control of microorganisms
US5051521A (en) * 1988-04-21 1991-09-24 Rhone-Poulenc Chimie Novel tin (IV) compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4082709A (en) * 1974-01-31 1978-04-04 The United States Of America As Represented By The Secretary Of The Navy Low leaching antifouling organometallic polyesters
US4499022A (en) * 1981-07-03 1985-02-12 Etat Francais Organometallic telomers, methods of preparation and biocidal compositions obtained
US5051521A (en) * 1988-04-21 1991-09-24 Rhone-Poulenc Chimie Novel tin (IV) compounds
US5043463A (en) * 1990-08-17 1991-08-27 Florida Atlantic University Novel compounds for the control of microorganisms

Also Published As

Publication number Publication date
DE2134358A1 (de) 1973-01-25
GB1399748A (en) 1975-07-02
FR2145559A1 (https=) 1973-02-23

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