Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2000-05-18
2003-03-04
Medley, Margaret (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C524S100000
Reexamination Certificate
active
06528556
ABSTRACT:
The present invention relates to a process for inhibiting the growth of photosynthetically active organisms on the surface of plastic materials, to biocidal polymer compositions, to the use of selected triazine compounds for the biocidal finishing of polymers and to plastic articles produced therefrom.
2-Alkylthio-4,6-diamino-s-triazines are known, inter alia, from DT-OS No. 1 914 014 as selective agents for controlling weeds and grass weeds.
EP-A-0 003 749 discloses selected 2-alkythio-4,6-diamino-s-triazines as effective marine algaecides.
The use of biocidally effective compounds, such as 2,4-bis(ethylamino)-6-chloro-s-triazine or N′-(3,4-dichlorophenyl)-N,N-dimethylurea in polyethylene (PE) or polyvinyl chloride (PVC) is also known and is described, inter alia, in DD 149 302.
If biocidally effective compounds are to be used with long-term effect in plastics, they must meet other requirements besides their biological activity, originating from the processing (temperature and shear forces) as well as from the use of the plastics (outdoor or indoor use).
The compounds proposed in the present state of the art are not able to be fully satisfactory in this respect so that there is still a need for having further bioactive compounds available which have a high biological effectivity and which meet the specific requirements for plastics.
Surprisingly, it has now been found that selected methylthio-s-triazines have excellent compatibility with polymers, do not sweat even after a prolonged period of time and have superior thermal resistance during their incorporation into the polymers as well as during the use of the plastic articles prepared therefrom.
The biocidal effect is maintained even after prolonged outdoor use and is virtually unaffected by wetness and moisture so that plastic articles finished in this manner are also suitable for uses in which they are temporarily or permanently surrounded by water or humidity. They are even suitable in an unusually advantageous manner for all those material applications in which the material is in contact with water over an extended period of time or permanently.
Within the scope of this invention, the term biocidal effect shall be taken to mean mainly a herbicidal effect, i.e. an inhibition of the growth of photosynthetically active organisms, in particular algae and mosses.
In one of its aspects, this invention relates to a process for biocidally finishing plastic materials selected from the group consisting of polyolefin, polystyrene, a halogen-containing polymer, polyacrylate or polymethacrylate, a polymer derived from unsaturated alcohols and amines or from their acyl derivatives or acetals, a homo- or copolymer of cyclic ethers, polyacetal, polyphenylene oxide or polyphenylene sulfide, polyurethane, polyamide or copolyamide, saturated or unsaturated polyester, polycarbonate, a phenol-formaldehyde resin, an epoxy resin or an aminoplastic resin, which process comprises adding
a) either during the processing of the plastic materials or,
b) in the case of plastic materials prepared via a radical polymerisation, already during the polymerisation or during the processing or,
c) in the case of duroplasts prepared from a phenol-formaldehyde resin, epoxy resin or an aminoplastic resin, during the crosslinking reaction, at least one compound selected from the group consisting of 2-methylthio-4-cyclopropylamino-6-(&agr;,&bgr;-dimethylpropylamino)-s-triazine, 2-methylthio-4-cyclopropylamino-6-tert-butylamino-s-triazine, 2-methylthio-4-ethylamino-6-tert-butylamino-s-triazine and 2-methylthio-4-ethylamino-6-(&agr;,&bgr;-dimethylpropylamino)-s-triazine.
The use of 2-methylthio-4-cyclopropylamino-6-tert-butylamino-s-triazine and/or of 2-methylthio-4-ethylamino-6-tert-butylamino-s-triazine is particularly preferred.
The compounds as such are known and are described, inter alia, in EP-A-0 003 749.
The biocidally effective compound is preferably added in an amount from 0.01 to 10% by weight, particularly preferably from 0.02 to 5% by weight and, very particularly preferably, from 0.05% to 3% by weight, based on the plastic material.
The biocidally effective compound can be added as pure substance or as a mixture with other plastic materials (master batch), such as LDPE, HDPE, PP or PET.
Selected plastic materials suitable for the process are mentioned above and are:
1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for instance of cyclopentene or norbornene, polyethylene (which optionally can be crosslinked), for example high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high density and ultrahigh molecular weight polyethylene (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE).
Polyolefins, i.e. the polymers of monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:
a) radical polymerisation (normally under high pressure and at elevated temperature).
b) catalytic polymerisation using a catalyst that normally contains one or more than one metal of groups IVb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either &pgr;- or &sgr;-coordinated. These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(III) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium. The catalysts can be used by themselves in the polymerisation or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups Ia, IIa and/or IIIa of the Periodic Table. The activators may be modified conveniently with further ester, ether, amine or silyl ether groups. These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).
2. Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP/HDPE, PP/LDPE) and mixtures of different types of polyethylene (for example LDPE/HDPE).
3. Copolymers of monoolefins and diolefins with each other or with other vinyl monomers, for example ethylene/propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene/but-1-ene copolymers, propylene/isobutylene copolymers, ethylene/but-1-ene copolymers, ethylene/hexene copolymers, ethylene/methylpentene copolymers, ethylene/heptene copolymers, ethylene/octene copolymers, propylene/butadiene copolymers, isobutylene/isoprene copolymers, ethylene/alkyl acrylate copolymers, ethylene/alkyl methacrylate copolymers, ethylene/vinyl acetate copolymers and their copolymers with carbon monoxide or ethylene/acrylic acid copolymers and their salts (ionomers) as well as terpolymers of ethylene with propylene and a diene such as hexadiene, dicyclopentadiene or ethylidene-norbornene; and mixtures of such copolymers with one another and with polymers mentioned in 1) above, for example polypropylene/ethylene-propylene copolymers, LDPE/ethylene-vinyl acetate copolymers (EVA), LDPE/ethylene-acrylic acid copolymers (EM), LLDPE/EVA, LLDPE/EAA and alternating or random polyalkylene/carbon monoxide copolymers and mixtures thereof with other polymers, for example polyamides.
4. Hydrocarbon resins (for example C
5
-C
9
) including hydrogenated modifications thereof (e.g. tackifiers) and mixtures of polyalkylenes and starch.
5. Polystyrene, poly(p-methylstyrene), poly(&agr;-methylstyrene).
6. Copolymers of styrene or &agr;-methylstyrene
Ergenc Nadi
Herbst Heinz
Voigt Wolfgang
Ciba Speciality Chemicals Corporation
Mansfield Kevin T.
Medley Margaret
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