Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2000-03-22
2002-02-19
Yoon, Tae H. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C524S027000, C524S059000, C524S127000, C524S186000, C524S211000, C524S430000, C524S494000, C524S589000, C528S259000
Reexamination Certificate
active
06348526
ABSTRACT:
FIELD
The invention concerns urea being condensated with other organic compounds with a plurality of nitrogen atoms such as amino compounds to produce amino condensation compounds. The invention also concerns their preparation and use. The amino condensation compounds are useful to produce flame retardant plastics and flame retard natural products, and may be reacted with phosphorus and/or boron containing compounds to produce other flame retardant compounds. The amino condensation compounds may also be reacted with aldehydes to produce amino condensation-aldehyde resins for use as molding compounds or as a flame retardant compound.
BACKGROUND
The heating of urea to produce urea condensation compounds, such as a mixture of cyanuric acid and cyamelide, is known in the arts, but the use of these compounds as a flame retardant is novel. The condensation of isocyanuric acid and/or cyanic acid, (which are produced by heating urea),with other nitrogen containing compounds to produce flame retardant compounds is novel. The amino condensation compounds and their phosphorus and/or boron salts are used as flame retardant compounds in plastics and natural products. Urea and melamine were utilized as a flame retardant compound by Fracalossi, et al., in U.S. Pat. No. 4,385,131. Melamine was utilized as flame retardant compounds in polyurethanes by Yukuta, et al., in U.S. Pat. No. 4,221,875 and by Grinbergs et al., in U.S. Pat. No. 4,745,133. Amino phosphates was utilized by Blount in U.S. Pat. No. 5,010,113.
What is lacking and what is needed are useful inexpensive nitrogen containing organic compounds with a plurality of nitrogen moieties. The amino condensation compounds and/or their salts of this invention are novel flame retardant compounds. The amino condensation compounds such as urea condensation compounds, urea-melamine condensation compound, urea-dicyandiamide compounds, urea-guanidine condensation compounds, etc., are novel flame retardant compounds. What is additionally lacking are compositions having such amino condensation compounds and/or their salts employed therein.
SUMMARY
In one aspect, the invention comprises amino condensation compounds and their salts.
Another aspect of the invention is a process to prepare amino condensation compound and/or their salts comprising serially contacting
(A) urea
(B) nitrogen containing compound containing free NH
2
—COOH, —OH, —NCO and/or epoxide radicals that will condensate or react with urea;
under conditions sufficient to prepare the amino condensation compounds. The urea may be first reacted with itself then reacted with Component B or with more urea plus Component B or with Component B.
In another aspect, the invention comprises amino condensation salt of phosphorus and/or boron containing compound and a process to prepare a amino condensation salt of a phosphorus and/or boron containing compound, employing phosphorus and/or boron containing compound that will react with the amino condensation compound under conditions sufficient to prepare the amino condensation salt of a phosphorus and/or boron containing compound, and a process to prepare an amino condensation salts of a phosphorus and/or a boron containing compound comprising serially contacting
(A) urea;
(B) nitrogen containing compound containing reactive —NH
2
, —COOH, —OH, —NCO and/or epoxide radicals that will condensate or react with urea;
Components A and B are first reacted to produce an amino condensation compound then a phosphorus and/or boron containing compound that will react with an amino condensation compound is added mixed and reacted.
An addition aspect of this invention is the production of amino condensation-aldehyde resins and a process to prepare amino condensation-aldehyde resinous compound under conditions sufficient to prepare the amino condensation-aldehyde resin comprising serially contacting
(A) urea;
(B) nitrogen containing compound containing reactive —NH
2
, —COOH, —OH, —NCO and/or epoxide radicals that will condensate or react with urea;
Components A and B are reacted thereby producing an amino condensation compound then
(C) aldehyde;
(D) basic or acidic catalyst, are added and reacted.
An additional aspect of this invention is the production of flame retardant amino condensation compositions by mixing together the following components
A) amino condensation compound and/or amino condensation salt of a phosphorus and/or boron containing compound and/or amino condensation-aldehyde resin;
B) carbonization auxiliaries;
C) filler.
An additional aspect of the invention is the use of the amino condensation compounds in the production of flame retardant amino condensation salts of phosphorus and/or boron compounds, in the production of amino condensation-aldehyde resins and in the production of amino condensation compositions. The flame retardant use comprises contacting an otherwise more flammable organic material with the amino condensation compounds and/or amino condensation salts of phosphorus and/or boron containing compounds and/or amino condensation-aldehyde resins and/or amino condensation composition thereof under conditions sufficient to lower the combustibility of the otherwise more flammable organic material, for example plastics, natural products or polyurethanes. Thus, a further aspect of the invention is a flame-retardant composition comprising an otherwise more flammable organic material incorporated therewith a flame retardant amount of an amino condensation compound and/or a amino condensation salt of a phosphorus and/or boron containing compound, and/or amino condensation-aldehyde resin, carbonization auxiliaries and fillers.
The flame-retardant compounds of this invention are produced by heating urea (Component A) with a nitrogen containing compound (Component B) to above the melting point of urea to about 160 degree C. at ambient or increased pressure for 1-3 hrs. Upon heating above the melting point, urea form very reactive compound isocyanic acid and/or cyanic acid which will react with itself many times to form large molecules of cyamelide or with other organic or inorganic nitrogen containing compounds especially amino compounds. The condensation of urea by heating is illustrated as follows:
H
2
NCONH
2
→NH
3
+HN═C═O⇄N═COH
wherein x is a number 3 to 10.
In order to increase the flame retardant properties and carbonization properties of the amino condensation compound a carbonization auxiliary, such as, phosphorus acidic compounds, organic phosphorus compounds that will react with an amino compound, boric acid, etc., is added to the melted amino condensation compound mixed and/or reacted. Other carbonization auxiliaries may be mixed with the amino condensation compounds to produce the flame retardant amino condensation composition. The amino condensation compounds may be further reacted with an aldehyde in the presence of a neutral or basic or acidic catalyst by mixing and heating the urea condensation compound with the aldehyde, usually in an aqueous medium, to just below the boiling point of the components at ambient or an elevated pressure thereby producing a urea condensation-aldehyde resin. The amino condensation salt of phosphorus compounds are produced by contacting the amino condensation compounds with a phosphorus containing compound that will react with an amino condensation compound, under conditions sufficient to prepare an amino condensation salt of a phosphorus containing compound. Fillers and carbonization auxiliaries may be added to the amino condensation compounds and/or amino salt of phosphorus and/or boron containing compounds and/or amino condensation-aldehyde resin. The amino condensation compounds and amino condensation-aldehyde resins with or without carbonization auxiliaries and fillers may be reacted with or added to or applied to a more flammable organic material.
The isocyanic acid may be reacted with itself to form biuret which is then reacted with an alkaline solution such as alkali metal hydroxides then neutralized with a metal sulfate such as cupric sulfate thereby form
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