EP0000892B1 - Compositions d'organopolysiloxane à activité microbicide, stables au stockage en l'absence d'humidité - Google Patents

Compositions d'organopolysiloxane à activité microbicide, stables au stockage en l'absence d'humidité Download PDF

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Publication number
EP0000892B1
EP0000892B1 EP78100604A EP78100604A EP0000892B1 EP 0000892 B1 EP0000892 B1 EP 0000892B1 EP 78100604 A EP78100604 A EP 78100604A EP 78100604 A EP78100604 A EP 78100604A EP 0000892 B1 EP0000892 B1 EP 0000892B1
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EP
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Prior art keywords
carbamate
benzimidazolyl
microbicidal
weight
mixture
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Expired
Application number
EP78100604A
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German (de)
English (en)
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EP0000892A1 (fr
Inventor
Hermann Dr. Genth
Wilfried Dr. Paulus
Paul Dr. Schiller
Hans Dr. Sattlegger
Karl Dr. Schnurrbusch
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Bayer AG
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Bayer AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C08K5/3447—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S528/901—Room temperature curable silicon-containing polymer

Definitions

  • the invention relates to microbicidal, in particular fungicidal, plastically deformable mixtures of organopolysiloxanes with certain crosslinking agents which change into a rubber-elastic state in the presence of water or water vapor.
  • Mixtures of this type are primarily used as joint putty and sealing compounds in construction, in sanitary facilities and in aquarium construction. They all contain, as a basic component, an ⁇ , ⁇ -dihydroxy-polydiorganosiloxane mixed with filler or other additives such as pigments. If you mix this with a silicon compound that contains at least three groups, which can react with both silanol groups and water, and exclude the ingress of moisture, this results in storage-stable mixtures that, when entering atmospheric air, become one through their water vapor content react elastomeric crosslinking product (see, for example, BW Noll, Chemistry and Technology of Silicone, Verlag Chemie, Weinheim 1968, p. 341, ff).
  • cross-linking water-reactive silicon compounds such as B. alkoxy, amino, oximato, acyloxy or acylamido silanes are known and customary.
  • alkoxy, amino, oximato, acyloxy or acylamido silanes are known and customary.
  • the variety of these crosslinking agents offers the welcome opportunity to adapt to the respective technical needs, for example with regard to processing, liability on the specified surface and mechanical properties.
  • the speed and sequence of these reactions are influenced by the addition of catalysts or other substances.
  • substances are sometimes added to these compositions to improve the adhesion of the crosslinked organopolysiloxane elastomer on various substrates.
  • Preferred benzimidazolyl alkyl carbamate is benzimidazolyl methyl carbamate.
  • additives are used in amounts such that 1 to 25 parts by weight of the additive are used for 1 part by weight of benzimidazolylalkyl carbonate.
  • microbicidal, in particular fungicidal, substance amounts to a total of 0.01-2% by weight, based on the total mixture. About 0.1-0.5% by weight is preferred.
  • the microbicidal, in particular fungicidal agents can, if appropriate, also be dissolved in solvents, for. B. in dioxane, the organopolysiloxanes are added.
  • the microbicidal, in particular fungicidal, agent can also be incorporated as a solid with a very small particle size (100-350 microns). But it is also possible to use the fungicide in the form of a paste, e.g. B. in a silicone oil (z. B. Polydimethylsiloxanöl) to incorporate.
  • the active ingredients used according to the invention are, for. B. against the following fungi: Penicillium species, such as Penicillium glaucum, Penicillium funieulosum, Penicillium citrinum and Penicillium camerunense, Mucor species, such as Mucor racemosus, Rhicopus species, such as Rhicopus nigricans, Pullularia species, such asPullularomium pullulans, Chaulomium species such as Chaetomium globosum, Geotrichum species such as Geotrichum candidum, Trichoderma species such as Trichoderma viride, Aspergillus species such as Aspergillus flavus, Aspergillus terreus and Aspergillus niger, and Coniophora species such as Coniophora cerebella.
  • these substances also act against yeasts, such as. B. Candida crusei and Candida albicans, against algae and other microorganisms.
  • a mixture of 60 g of ⁇ , ⁇ -dihydroxypolydimethylsiloxane with a viscosity of 50,000 cP and 25 g of ⁇ , ⁇ -bis (trimethylsiloxy) polydimethylsiloxane with a viscosity of 1300 cP is initially introduced.
  • 4 g of ethyl triacetoxysilane are added and stirred briefly.
  • 1.5 g of titanium dioxide and 9.5 g of a finely dispersed silica and 0.3 g of a mixture of 6 parts by weight of N- (fluorodichloromethylthio) phthalimide and 1 part by weight of methylbenzimidazolylmethyl carbamate are now added.
  • the mixture is stirred in a planetary mixer until homogeneous, which is the case after about 20 minutes.
  • a catalyst in this case e.g. B. 5 mg of dibutyltin diacetate, added and stirred in homogeneously under vacuum for 10 minutes. Evacuation is useful in order to be able to fill the mass homogeneously into a storage container (tube, cartridge) after the mixing process.
  • the molding composition according to the invention was stored for 8 weeks at 50 ° C. for testing the storage stability and then spread out about 2 mm thick and cured to a rubber sheet in about one day with atmospheric humidity (65% relative atmospheric humidity) .
  • the plate was snow-white despite the paste being stored at 50 ° C (which corresponds to a storage stability of approx. 1 ⁇ 2 year required by practice at changing room temperatures) and shows no discoloration.
  • Such a rubber - elastic skin has the following mechanical properties, both before and after storage: elastic modulus approx. 0.4 MPa, tensile strength approx. 1.4 MPa, elongation at break approx. 600%, Shore A hardness approx 22.
  • a mixture of 45 parts by weight was ⁇ , ⁇ -dihydroxypolydimethylsiloxane with a viscosity of 50,000 cP and 20 parts by weight.
  • At room temperature 5 parts by weight.
  • Diacetessigesterdiisobutyltitanol given and mixed for about 5 minutes at room temperature.
  • 5 parts by weight. a finely dispersed silica, 20 parts by weight Chalk, 2 parts by weight White pigment (Ti0 2 ) and 0.1 wt.
  • a fungicide paste consisting of 60 parts by weight of ⁇ , ⁇ -bis (trimethylsiloxy) polydimethylsiloxane, 1 part by weight of dioxane, 5 parts by weight of highly disperse silica and 30 parts by weight of a mixture consisting of 6 parts by weight of N- (fluorodichloromethylthio) phthalimide and 1 part by weight of methylbenzimidazolylmethylcarbamate) and 1 part by weight of TI
  • dibutyltin dimaleinate as a catalyst, stir for about 10 minutes and add 4 parts by weight to the entire mixture. of di (N-methylbenzamido) methylethoxysilane and mix under vacuum for 15 minutes. The further treatment is carried out as in Example 1.
  • the mechanical properties were: Young's modulus approx. 0.14 MPa, tensile strength approx. 0.7 MPa, elongation at break approx. 550%, Shore A hardness approx. 12.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)

Claims (2)

1. Masses de moulage d'organopolysiloxanes à activité microbicide, en particulier fongicide, consistant en un mélange d'α,ω-dihydroxypolydiorganosiloxanes, de composés de silicium servant d'agents de réticulation et, éventuellement, d'α,ω-bis-(triméthylsiloxy)-polydiméthylsiloxane, de matières de charge et de sels de métaux lourds ou d'amines accélérant de manière connue la réticulation, de même que de microbicides, caractérisées par une teneur en un benzimidazolylcarba- mate d'alcoyle de formule:
Figure imgb0004
dans laquelle
RI est un radical alcoyle ayant 1 à 4 atomes de carbone qui est éventuellement substitué par le radical -OR3, où R3 représente un radical alcoyle ayant 1 à4 atomes de carbone ou le radical phényle et
R2 est de l'hydrogène, un radical alcoyle ayant 1 à 4 atomes de carbone, de l'halogène ou le groupe nitro,

ainsi éventuellement qu'en d'autres substances à activité fongicide, la quantité totale de substances microbicides s'élévant à 0,01 ―2% en poids par rapport au mélange total.
2. Masses de moulage d'organopolysiloxanes selon la revendication 1, caractérisées en ce que pour l'apprêtage microbicide elles contiennent un mélange de méthylbenzimidazolylcarbamate de méthyle et de N-(fluorodichlorométhylthio)-phthalimide.
EP78100604A 1977-08-19 1978-08-07 Compositions d'organopolysiloxane à activité microbicide, stables au stockage en l'absence d'humidité Expired EP0000892B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2737405A DE2737405B2 (de) 1977-08-19 1977-08-19 Unter Ausschluß von Wasser lagerfähige, mikrobicid wirkende Organopolysiloxanformmassen
DE2737405 1977-08-19

Publications (2)

Publication Number Publication Date
EP0000892A1 EP0000892A1 (fr) 1979-03-07
EP0000892B1 true EP0000892B1 (fr) 1981-03-18

Family

ID=6016784

Family Applications (1)

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EP78100604A Expired EP0000892B1 (fr) 1977-08-19 1978-08-07 Compositions d'organopolysiloxane à activité microbicide, stables au stockage en l'absence d'humidité

Country Status (14)

Country Link
US (1) US4228065A (fr)
EP (1) EP0000892B1 (fr)
JP (1) JPS6018697B2 (fr)
AU (1) AU522775B2 (fr)
BR (1) BR7805337A (fr)
CA (1) CA1129134A (fr)
DD (1) DD138427A5 (fr)
DE (2) DE2737405B2 (fr)
DK (1) DK367578A (fr)
ES (1) ES472671A1 (fr)
FI (1) FI782515A (fr)
IT (1) IT7850754A0 (fr)
NO (1) NO782677L (fr)
NZ (1) NZ188158A (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5860683U (ja) * 1981-10-20 1983-04-23 株式会社　多田野鉄工所 油圧作動アタツチメント作動油給排手段
US4488241A (en) * 1981-12-08 1984-12-11 Zymark Corporation Robot system with interchangeable hands
EP0229862A3 (fr) * 1986-01-24 1987-09-30 TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION Instrument médical
JPH04112803A (ja) * 1990-08-31 1992-04-14 Sekisui Chem Co Ltd 防カビ組成分
US5332431A (en) * 1992-03-31 1994-07-26 Nippon Paint Co., Ltd. Antifouling paint
JPH0640821A (ja) * 1992-07-24 1994-02-15 Toshiba Silicone Co Ltd 防カビ性ポリオルガノシロキサン組成物
FR2809273B1 (fr) * 2000-05-19 2002-08-30 Cit Alcatel Procede de signalisation de parametres de mode compresse a une station mobile
EP1693420B1 (fr) * 2005-01-27 2014-06-04 Coltène/Whaledent AG Kit comprenant un matériau polymère transparent pour l'enregistrement de traces de doigt
JP5270629B2 (ja) * 2010-09-10 2013-08-21 アイカ工業株式会社 室温硬化性オルガノポリシロキサン組成物
JP2013194063A (ja) * 2012-03-15 2013-09-30 Aica Kogyo Co Ltd 室温硬化性ポリオルガノシロキサン組成物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2902467A (en) * 1959-09-01 Siloxane-silicate elastomers
FR1073431A (fr) * 1951-12-17 1954-09-24 Dow Corning Perfectionnement aux compositions fongicides
FR1462754A (fr) * 1965-02-17 1966-12-16 Dow Corning Compositions améliorées, pour assurer l'étanchéité
FR1529820A (fr) * 1967-05-09 1968-06-21 Rhone Poulenc Sa Aminosilanes et compositions en contenant
US3532726A (en) * 1967-10-30 1970-10-06 Gen Electric Acyloxy mercury-substituted organosilicon compounds
US3562290A (en) * 1967-11-07 1971-02-09 Du Pont Process for making 2-benzimidazolecarbamic acid alkyl esters
JPS5319345B2 (fr) * 1974-05-17 1978-06-20
JPS51125744A (en) * 1974-09-17 1976-11-02 Nippon Chem Ind Co Ltd:The A fungicide for industry
JPS5141433A (en) * 1974-09-30 1976-04-07 Takeda Chemical Industries Ltd Hiiryoyosatsukinzainoseizoho

Also Published As

Publication number Publication date
AU3897178A (en) 1980-02-21
ES472671A1 (es) 1979-11-16
DK367578A (da) 1979-02-20
NO782677L (no) 1979-02-20
AU522775B2 (en) 1982-06-24
IT7850754A0 (it) 1978-08-17
FI782515A (fi) 1979-02-20
DE2860545D1 (en) 1981-04-16
NZ188158A (en) 1979-11-01
JPS6018697B2 (ja) 1985-05-11
DE2737405B2 (de) 1980-07-10
DD138427A5 (de) 1979-10-31
US4228065A (en) 1980-10-14
EP0000892A1 (fr) 1979-03-07
DE2737405A1 (de) 1979-03-01
CA1129134A (fr) 1982-08-03
BR7805337A (pt) 1979-05-02
JPS5443260A (en) 1979-04-05

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