Supramolecular compound

Details Supramolecular compound Supramolecular compound

2000-02-24

2004-01-27

Sergent, Rabon (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From reactant having at least one -n=c=x group as well as...

C106S018320, C106S018330, C106S031430, C106S031450, C106S031460, C106S031470, C106S031750, C106S031760, C106S031770, C428S373000, C428S375000, C428S378000, C428S392000, C385S115000, C385S123000, C544S196000, C544S200000, C544S205000, C544S206000, C544S320000, C564S022000, C564S032000, C564S038000, C564S103000, C564S123000, C546S244000, C560S025000, C560S026000, C560S115000, C560S157000, C560S158000, C528S060000, C528S061000, C528S064000, C528S068000, C528S076000, C528S080000, C528S084000, C528S085000

Reexamination Certificate

active

06683151

ABSTRACT:

The invention relates to supramolecular compounds containing reaction products that form interactions between one another of which the strongest interactions are reversible physical interactions, in particular hydrogen bonds. These interactions are further called reversible intermolecular physical interactions.
Such supramolecular compounds, for instance polymers, are described in Macromolecules (1995,28,782-783) by Lange and Meijer. These polymers can be obtained by radical polymerization of, for instance, styrene and a maleimide monomer. The resulting copolymer is mixed with melamine. A disadvantage of mixtures thus obtained is that they are very brittle and have inadequate mechanical properties
In general, “supramolecular chemistry” is understood to be the chemistry of non-covalent, oriented, multiple (at least two), cooperative interactions. For instance, a “supramolecular polymer” is an organic compound which essentially obtains its polymeric properties, for instance with respect to its theological behaviour, through a combination of covalent bonds and specific secondary interactions with high physical bond strengths that contribute substantially to the properties of the resulting material.
The aim of the invention is to provide “supramolecular” compounds that contain reaction products that at least partially form physical interactions, such as hydrogen bonds, between one another; said supramolecular compounds exhibiting a relatively high elongation at break.
The compound according to the invention is the reaction product of an isocyanate, a hydroxy functional, an acid functional or an amino functional compound and a nitrogen-containing compound capable of reacting with an isocyanate.
The compound according to the invention comprises reaction products of (A) an isocyanate functional compound of which at least 40 wt. %, relative to the total amount of (A), has a molecular weight of at least about 500, and (B) a nitrogen-containing compound capable of reacting with said isocyanate functional compound (A).
The reaction product of the present invention has a molecular weight of less than about 20,000. The reaction product comprises an effective amount of groups that are able to form reversible intermolecular physical interactions such that a resulting compound comprising the reaction product shows polymeric mechanical properties at a temperature below a transition temperature. The compound of the present invention has an elongation at break at 25° C. of at least about 2%.
For the sake of clear definition, the terms “supramolecular compound”, “compound” and “composition” will be interchangeably used to define a compound that contains the reaction product forming reversible physical bonds between the molecules, in other words, to define the association of the molecules. The term “reaction product” and “molecules” will be interchangeably used throughout the description for defining the structural units of which the supramolecular compound is built up.
Preferably, the isocyanate functional compound (A) is formed by the reaction of (i) an isocyanate with (ii) a hydroxy functional, an acid functional or an amino functional compound of which at least 40 wt. %, relative to the total amount of (ii) is having a molecular weight of at least about 450.
The isocyanate (i) and isocyanate functional compound (A) preferably are at least bifunctional.
The isocyanate functional compound can comprise an isocyanate functional group (—NCO) and/or a compound, which is the reaction product of an isocyanate group with a blocking group, further called a blocked isocyanate group.
In another embodiment of the present invention the product is the reaction product of (A) an isocyanate functional compound having a functionality of at least two and of which at least 40 wt. % is having a molecular weight of at least about 500, and (B) a nitrogen-containing compound that is capable of reacting with compound (A) and that comprises additionally to said nitrogen n amino-groups, wherein n is at least 1. Preferably, the molar ratio is chosen as such that only one amino-group per compound (B) reacts with one isocyanate-group of (A), irrespectively of the number of amino groups present in (B).
From DE-A-2364157 it is known to first react a diisocyanate with an hydroxy functional compound to form a diisocyanate functional compound and to further react one mole of said diisocyanate functional compound with one mole of a melamine derivative such that melamine acts as a polyamine crosslinking compound. In other words, a polymer is formed.
From DE-A-2625399 it is further known to crosslink a diisocyanate functional polyether compound with a melamine derivative as diamine by using substantially equal molar amounts of diisocyanate and diamine.
From WO 96/35135 an optical fiber surrounded with a reversibly cross-linked plastic covering material is known. Further, a method is known of manufacturing said fiber by depositing thereon said plastic material at a temperature higher than 70° C. and by cross-linking said material when cooling to a temperature close to ambient temperature. The plastic material described in WO 96/35135 consists of reversible chemical crosslinks and is, in particular, produced by the reaction of a non-linear polyimide reactant having an imide functionality of at least three and a polyamine comprising at least two primary or secondary amino functionalities. The disadvantage of the use of a reversible chemical crosslinked material as described in WO 96/35135 and in WO 95/00576 cited therein, is that the de-crosslinking step does not occur to an extent which is sufficient in terms of achieving, from thermodynamic point of view, the required flow.
Further, from WO 98/14504, supramolecular compounds are known containing hydrogen-bridge-forming monomer units that in pairs form at least 4 hydrogen bonds with one another. For instance, 1 mol of a low Mw diisocyanate functional compound reacts with 2 mols of a substituted isocytosine compound to form said supramolecular compound. The disadvantage of the supramolecular compounds disclosed in WO 98/14504 is that they are too brittle.
The compound (or the mixture of compounds) according to the invention derive their properties in part from the multiple hydrogen bonds that are formed between the various reaction products. These reaction products consist of a hydroxy, amino or acid functional compound (ii) that is successively converted with, for instance, a diisocyanate (i) to form a diisocyanate functional compound (A). Said compound (A) then reacts with a nitrogen-containing compound (B). The hydroxy, amino or acid functional compound (ii) preferably is at least bifunctional and at least 40 wt. % (relatively to the total amount of (ii)) of said hydroxy, amino or acid functional compound has a molecular weight of at least about 450. Surprisingly, the compounds obtained have a relatively high elongation at break at room temperature (25° C.), even though their molecular weight is still relatively low.
The compound of the invention will be thermally formed or hardened, in other words, the compound will be formed by association of a suitable amount of reaction products when lowering the temperature. In particular, by lowering the temperature below a certain defined transition temperature.
The transition temperature can be defined as the temperature at which a substantial amount of intermolecular physical interactions are formed between the various reaction products. The physical interactions, formed between the various molecules, can be reversibly and at least partially broken, in particular by increasing the temperature to a temperature above a certain transition temperature
The transition temperature can further be defined as the temperature below which the compound shows polymeric mechanical properties similar to those of thermoplastic materials at such temperatures. In particular, the temperature at which the reaction product shows a tensile strength of at least 0.05 MPa, preferably at least 0.1 MPa. Another way to define the transition temperature is the temper

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