-
Notifications
You must be signed in to change notification settings - Fork 918
Commit
Add a backend implementation to parse patent applications and grants from the United States Patent Office (USPTO). Signed-off-by: Cesar Berrospi Ramis <[email protected]>
- Loading branch information
There are no files selected for viewing
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Large diffs are not rendered by default.
Original file line number | Diff line number | Diff line change |
---|---|---|
@@ -0,0 +1,165 @@ | ||
PATN | ||
WKU 045931038 | ||
SRC 6 | ||
APN 5253349 | ||
APT 1 | ||
ART 154 | ||
APD 19830822 | ||
TTL Polyoxazoline compounds | ||
ISD 19860603 | ||
NCL 2 | ||
ECL 1,2 | ||
EXA Gibson; S. A. | ||
EXP Lesmes; George F. | ||
INVT | ||
NAM Johnson; Mark R. | ||
CTY Breckenridge | ||
STA MI | ||
ASSG | ||
NAM The Dow Chemical Company | ||
CTY Midland | ||
STA MI | ||
COD 02 | ||
CLAS | ||
OCL 548239 | ||
XCL 544 88 | ||
EDF 4 | ||
ICL C07D41312 | ||
FSC 548 | ||
FSS 239 | ||
FSC 544 | ||
FSS 88 | ||
UREF | ||
PNO 3563920 | ||
ISD 19710200 | ||
NAM Tomalia et al. | ||
OCL 548239 | ||
UREF | ||
PNO 3682948 | ||
ISD 19720800 | ||
NAM Tomalia et al. | ||
OCL 548239 | ||
UREF | ||
PNO 3996237 | ||
ISD 19761200 | ||
NAM Tomalia | ||
OCL 544 88 | ||
OREF | ||
PAL Hackh's Chemical Dictionary, 4ed, 1969, McGraw-Hill Book Company, p. 331. | ||
ABST | ||
PAL Polyoxazoline compounds are prepared by reacting a polymercaptan with a | ||
2-alkenyloxazoline or a 2-alkenyloxazine. The compounds so prepared have | ||
at least two oxazoline or oxazine functionalities and can be employed in | ||
applications where a compound having an oxazoline or oxazine functionality | ||
has useful activity. | ||
BSUM | ||
PAC BACKGROUND OF THE INVENTION | ||
PAR This invention relates to polyoxazoline and polyoxazine compounds and, in | ||
particular, those compounds having at least two pendant oxazoline or | ||
oxazine functionalities. | ||
PAR Compounds having two or more oxazoline rings are useful as crosslinking | ||
agents. Previously, such compounds have been prepared a number of ways, | ||
each having some limitations. Bisoxazolines have been prepared by the | ||
reaction of dicarboxylic acids with monoethanolamine. This reaction is not | ||
especially clean, and requires difficult purification procedures. | ||
Bisoxazolines have also been prepared by reaction of hydrogen sulfide with | ||
isopropenyl oxazoline. This reaction is only capable of producing | ||
bisoxazolines and, thus, is not useful in preparing higher polyoxazolines. | ||
Another method of preparing polyoxazolines is by homo- or copolymerization | ||
of isopropenyl oxazoline. This procedure is frequently unsatisfactory as | ||
it produces polyoxazolines with many pendant groups, resulting in | ||
inefficient use of the oxazoline rings in crosslinking reactions. Also, | ||
since the polyoxazoline has a high molecular weight, it is often not | ||
convenient to handle and use. | ||
PAR In view of the deficiencies of the prior art, it would be highly desirable | ||
to prepare, in a relatively simple and efficient manner, a compound having | ||
a plurality of oxazoline or oxazine rings. | ||
PAC SUMMARY OF THE INVENTION | ||
PAR The present invention is a compound comprising at least two, preferably at | ||
least three, oxazoline or oxazine functionalities which result from the | ||
reaction of a polymercaptan and a 2-alkenyloxazoline or a | ||
2-alkenyloxazine. | ||
PAC DETAILED DESCRIPTION OF THE INVENTION | ||
PAR The 2-alkenyloxazolines and 2-alkenyloxazines of the present invention have | ||
the general formula: | ||
##STR1## | ||
wherein R is hydrogen or lower alkyl, and each of R.sup.1 -R.sup.4 is | ||
independently hydrogen, alkyl, aralkyl, phenyl or inertly substituted | ||
phenyl; and n is zero or one. Examples of suitable 2-alkenyloxazolines and | ||
2-alkenyloxazines and their methods of preparation are catalogued in U.S. | ||
Pat. Nos. 3,505,297 and 4,144,211, which are incorporated herein by | ||
reference. Examples of preferred 2-alkenyloxazolines include | ||
2-isopropenyloxazoline, 2-vinyloxazoline, and | ||
5-methyl-2-isopropenyloxazoline. | ||
PAR The polymercaptans of this invention are selected from a known class of | ||
compounds having many members, and any member of this class which reacts | ||
with vinyl functionalities can be employed. Polymercaptans, for purposes | ||
of this invention, contain at least two, preferably at least three, | ||
mercapto (i.e., --SH) groups. Although the structure of the polymercaptan | ||
is not particularly critical and can vary depending upon the desired | ||
application, preferred polymercaptans are those which correspond to the | ||
formula R(--SH).sub.n wherein R is a hydrocarbyl or inertly substituted | ||
hydrocarbyl group of from 1 to about 24 carbon atoms, most preferably from | ||
1 to about 6 carbon atoms; and n is from 2 to about 10, preferably from 3 | ||
to about 10, most preferably from 3 to about 6. Examples of especially | ||
preferred polymercaptans are pentaerythritol tetra-3-mercaptopropionate | ||
and dipentaerythritol hexa-3-mercaptopropionate. | ||
PAR Catalysts useful herein include the known free radical generating | ||
catalysts, such as the organic peroxides, the azobis compounds, actinic | ||
light, electron beams or other high energy radiation. Particularly useful | ||
catalysts include the amine catalysts such as triethyl amine. | ||
PAR The amount of polymercaptan which is employed is most preferably an amount | ||
such that there are an equivalent number of mercapto groups and | ||
2-alkenyloxazolines or 2-alkenyloxazines. Alternatively, there can be a | ||
slight excess of mercapto groups over 2-alkenyloxazolines or | ||
2-alkenyloxazines. | ||
PAR Compounds of this invention which contain two or more oxazine or oxazoline | ||
rings are prepared at very high yield in very high purity. Preferably, the | ||
desired 2-alkenyloxazoline or 2-alkenyloxazine is added to an inert | ||
organic solvent with an effective amount of a suitable catalyst and the | ||
desired polymercaptan. It is desirable to heat the reaction mixture, as | ||
for example by reflux, for a period from 1/2 to about 5 hours. The | ||
compound is prepared quickly and efficiently, is obtained without | ||
significant by-product and no further purification is required. | ||
PAR The compounds of this invention can be reacted with ethylenically | ||
unsaturated carboxylic acids as described in U.S. Pat. No. 3,996,237 which | ||
is incorporated herein by reference. Thus, the compounds of this invention | ||
are particularly useful in introducing crosslinking capabilities to | ||
numerous polymers prepared from ethylenically unsaturated monomers. | ||
PAR In addition, the compounds of this invention are useful in the various | ||
other applications where a compound comprising a pendant oxazine or | ||
oxazoline ring is known to have useful activity. Of particular interest is | ||
the preparation of highly branched and/or crosslinked polyoxazoline and | ||
polyoxazine networks. For example, the compounds of this invention can be | ||
contacted with an alkyloxazine or alkyloxazoline under conditions suitable | ||
to bring about oxazoline or oxazine polymerization. It is understood that | ||
the greater the number of pendant oxazoline or oxazine rings per molecule | ||
of compound of this invention, the greater the branching or network form | ||
of the polymer so prepared. | ||
DETD | ||
PAR The following example is presented to illustrate the invention and should | ||
not be construed as limiting its scope. | ||
PAC EXAMPLE 1 | ||
PAR To a solution comprising 5 g of pentaerythritol tetra-3-mercaptopropionate | ||
in 15 ml of toluene is added 4.30 g of isopropenyl oxazoline and 0.15 ml | ||
of triethylamine. The solution is heated to reflux for 2 hours and allowed | ||
to cool to room temperature. The solvent is removed under reduced pressure | ||
to yield the tetraoxazoline which is a clear viscous product. The product | ||
has the structure: | ||
##STR2## | ||
PAC EXAMPLE 2 | ||
PAR To a solution comprising 50 g of dipentaerythritol | ||
hexa-3-mercaptopropionate in 200 ml of acetonitrile is added 42.5 g of | ||
isopropenyl oxazoline and 2 ml of triethylamine. The solution is heated to | ||
reflux at 80.degree. C. for 5 hours and allowed to cool to room | ||
temperature. The solution is stirred for 2 days. The solvent is removed | ||
under reduced pressure to yield the hexaoxazoline which is a viscous oil. | ||
The product has the structure: | ||
##STR3## | ||
CLMS | ||
STM What is claimed is: | ||
NUM 1. | ||
PAR 1. A compound having the structure: | ||
NUM 2. | ||
PAR 2. A compound having the structure: | ||
##STR4## |