Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
1999-05-05
2001-05-29
Sanders, Kriellion (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
Reexamination Certificate
active
06239192
ABSTRACT:
The present invention relates to new shaped articles which comprise active compounds and are based on thermoplastically processable, biologically degradable polymers, preferably polyesters, polyester amides, polyester urethanes and polyesterurethane ureas, and their production and use for combating parasites on, around and in the environment of host animals, the shaped articles optionally serving, after use, for combating phytopathogenic insects on open-air or indoor plants.
Shaped articles which comprise active compounds for controlling pests are known. They are based on the slow release of active compounds from a carrier matrix of plastic which contains active compounds (cf., for example, Aries et al. U.S. Pat. No. 3,814,061, Greeberg U.S. Pat. No. 3,918,407, Miller et al. U.S. Pat. No. 3,944,662, Millionis et al. U.S. Pat. No. 4,041,151, Pasarela U.S. Pat. No. 4,145,409, Greenberg and Cloud U.S. Pat. No. 4,158,051, v. Bittera et al. U.S. Pat. No. 4,225,578, Mc Daniel et al. European Published Specification 0 052 411, Grubb et al. U.S. Pat. No. 3,852,416 and Pearce U.S. Pat. No. 4,536,388).
The carrier employed almost exclusively in known shaped articles in practice is PVC. Although other carriers are mentioned in the literature, to date they have not found acceptance in practice. U.S. Pat. No. 4,195,075 thus mentions, inter alia, that thermoplastic elastomers are also possible carrier polymers for ear tags. However, it is also exclusively examples with plasticized PVC as the carrier polymer which are described in this reference.
This is also not astonishing. PVC is inexpensive and readily accessible. It is also miscible with other substances, in particular plasticizers, in wide ranges. In PVC bodies comprising active compounds, these plasticizers have the function of keeping the active compound dissolved in the carrier and of transporting it slowly to the surface of the body. The active compound evaporates there, or it is rubbed off from the surface together with the plasticizer. The interaction of the three components of PVC carrier, plasticizer and active compound determines whether and to what extent the shaped article can be employed in practice.
If one component of the overall system is changed, it can no longer be predicted whether the system still acts in practice. This applies in particular if the plasticizer, which indeed has a key function in transportation of the active compound, is changed or omitted.
For various reasons, it is desirable to replace PVC as the carrier material.
Shaped articles which contain active compounds and are based on thermoplastically processable elastomers (TPE) are described in EP-A 542 080, 542 081 and 542 078.
The known systems have the disadvantage that their action rapidly becomes inadequate, although often more than 90% by weight of the active compound originally employed is still present in the polymer. This is very uneconomical.
The systems according to the invention allow, after they have been employed for combating parasites on, around and in the environment of host animals, the active compound remaining in them to be utilized economically. For this purpose, they are employed as agents for combating pests on plants in soil, optionally after granulation or grinding.
It was surprising that the shaped articles according to the invention, comprising active compounds, are biologically degraded completely, the active compound contained in them being released. The expert had to expect that the active compounds incorporated into the polymer matrix impede or suppress the biological degradation of polymers which are biologically degradable per se.
The present invention relates to:
1. Shaped articles comprising active compounds, characterized in that they comprise biologically degradable polymers as the carrier, if appropriate plasticizers and if appropriate customary additives.
2. Shaped articles comprising active compounds, characterized in that they comprise biologically degradable polyester amides as the carrier, if appropriate plasticizers and if appropriate customary additives.
3. Process for the production of shaped articles comprising active compounds, characterized in that biologically degradable polymers, preferably thermoplastic polyester amides, are mixed with active compounds, if appropriate plasticizers and if appropriate customary additives and the mixture is processed in the customary manner.
4. Use of the polymer mixtures according to 1 and 2 (above) as shaped articles, preferably tapes, medallions and ear tags, for combating parasites on or around animals, and after use, optionally after comminution, granulation or grinding, as soil granules for combating phytopathogenic insects on open-air or indoor plants.
Biologically degradable polymers are those which meet the test conditions described in the draft specification DIN 54 900-1.
Examples of biologically degradable polymers are polycaprolactone, polycaprolactone-starch blends, aromatic-aliphatic copolyesters, polylactide, polyhydroxybutyrates/valerates and/or starch blends thereof, polyester amides, polyurethanes, polyureas, polyurethane ureas and their blends.
The preparation of suitable polyester amides is described in EP-A 641 817. Reference is made in particular to the polyester amides described therein. Polyester amides are particularly suitable according to the invention.
The preparation and use of thermoplastic polyester urethanes as compostable plastics is described in EP 0 593 975.
The preparation of suitable polyurethane ureas is described in WO 96/35733 and WO 96/38502. Reference is made in particular to the polyurethane ureas described therein. Polyurethane ureas are particularly suitable according to the invention.
Such biologically degradable polyurethanes which can be shaped thermoplastically and contain urea groups are prepared by known processes, adhering to an equivalent ratio of isocyanate groups to groups which are reactive towards isocyanate groups of 1:1 to 2:1, from
a) a diisocyanate component comprising
a1) hexamethylene diisocyanate or
a2) mixtures of hexamethylene diisocyanate with a total of up to 60% by weight, based on a mixture, of 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane and/or 4,4′-diisocyanatodicyclo-hexylmethane and/or 1-methyl-2,4(6)-diisocyanatocyclohexane with
b) a diol component comprising
b1) at least one polyester diol of molecular weight, which can be calculated from the hydroxyl group content, of 500 to 10,000 from (i) adipic acid and/or succinic acid and (ii) at least one alkanediol having 2 to 6 carbon atoms, or
b2) a mixture of such polyester diols with up to 32% by weight, based on the total weight of component b), of alkanediols which have 2 to 6 carbon atoms and optionally contain ether groups,
c) a diamine component in an amount of 2 to 50 equivalent %, based on the total amount of groups which are reactive towards isocyanate groups and are present in components b) and c), comprising
c1) diaminosulphonates of the general formula
H
2
N—(—CH
2
—)
n
—NH—(—CH
2
)
m
—SO
3
Me
or
c2) mixtures of diaminosulphonates C1) with up to 90% by weight, based on the total weight of component c), of ethylenediamine, if appropriate
d) hydrophilic polyether alcohols of the general formula
H—X—O—R
in an amount of up to 10% by weight, based on the total weight of components b), c) and d), and if appropriate
e) water, which is not included in the calculation of the equivalent ratio of isocyanate groups to groups which are reactive towards isocyanate groups,
wherein, in the general formulae mentioned,
m and n independently of one another represent numbers from 2 to 6,
Me represents potassium or sodium,
R represents a monovalent hydrocarbon radical having 1 to 12 carbon atoms and
X denotes a polyalkylene oxide chain of the molecular weight range 88 to 4000, the alkylene oxide units of which comprise ethylene oxide units to the extent of at least 40% and propylene oxide units as the remainder.
The polyurethanes containing urea groups are employed, for example, in the form of 20 to 50, preferably 40 to 50, % st
Gruttmann Horst
Hackemüller-Bruns Doris
Heeschen Kerstin
Muller Hanns Peter
Akorli Godfried R.
Bayer Aktiengesellschaft
Gil Joseph C.
Sanders Kriellion
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