Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
2000-01-04
2004-05-04
Lipman, Bernard (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S332100, C525S332800, C525S332900, C525S333100, C525S333700, C525S383000, C525S385000, C525S386000
Reexamination Certificate
active
06730747
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel compounds formed from acyclic carbonyl compounds and unsaturated hydrocarbons.
BACKGROUND OF THE INVENTION
Various unsaturated hydrocarbon polymers have been reacted with maleic anhydrides to form a variety of maleic anhydride adducts of unsaturated hydrocarbon polymers. The reactivity of maleic anhydride with many unsaturated hydrocarbon polymers is poor and in some instances, as for example with EPDM rubber, even employment of extensive heating is ineffective. Free employment of extensive heating is ineffective. Free radical reactions which graft maleic anhydride onto the unsaturated hydrocarbon polymer have been utilized as alternative routes. Free radical grafting leads to chain scission, crosslinking and solvent grafting if the solvent is sufficiently reactive. The reaction of acyclic carbonyl monomers with the unsaturated hydrocarbon polymer overcomes these aforementioned deficiencies in that the acyclic carbonyl monomers can be reacted with the unsaturated hydrocarbon polymer at moderate temperatures in either the bulk or solution state without the employment of free radical initiators to form novel polymers which are useful as solution viscosifiers.
SUMMARY OF THE INVENTION
In accordance with the present invention, there is provided a novel composition of matter having the formula:
wherein R
a
, R
b
, R
c
, R
d
and R
e
are independently selected from the group consisting of H, alkyl groups and substituted alkyl groups having about 1 to 10
6
carbon atoms, alkenyl groups and substituted alkenyl groups having about 3 to 10
6
carbon atoms, wherein the substituents on the alkyl and/or alkenyl groups are selected from the group consisting of alkoxy, halogen, CN, OH, HO(CH
2
CH
2
O)x (X=1-10), acyl, acyloxy and aryl substituents.
These novel compounds are formed by contacting a hydrocarbon having the formula:
with an acyclic carbonyl having the formula:
for a time and at a temperature sufficient to form the compounds, and in which R
a
, R
b
, R
c
, R
d
, R
e
, X and Y are as described above and Q=HOH, MeOH, EtOH, or n-BuOH; n=0,1,>1; X or Y are selected from the group consisting of —OH; —OR
1
; NR
1
R
2
; R
1
; wherein R
1
has about 1 to about 18 carbon atoms,
wherein R
2
is hydrogen or any alkyl group of from about 1 to about 18 carbon atoms, —NR
3
R
4
wherein R
3
and R
4
are alkyl groups of from about 1 to about 18 carbon atoms; OR
5
wherein R
5
is hydrogen or an alkyl group having about 1 to about 18 carbon atoms, —COOR
6
wherein R
6
is hydrogen or an alkyl group having about 1 to about 18 carbon atoms, —CN, and —SR
7
wherein R
7
is an alkyl group having about 1 to about 18 carbon atoms. Typical monomers are ketomalonic acid, esters of ketomalonic acid including alkyl and aryl esters; other useful keto-acids are alpha keto succinic acid, diketo succinic acid, and any alpha ketohydrocarboic acid and alpha, beta-diketohydrocarboic acids and their ester and amide analogs which have a molecular weight of about 130 to 500. Useful ketones include dimethyl, diphenyl and di-tolyl tri- and tetraketones.
The compounds of the present invention are useful as solution viscosification agents.
GENERAL DESCRIPTION
Compounds having the formula:
are prepared by contacting an olefinic compound and an acyclic carbonyl compound for a time and at a temperature sufficient to form the compound. Thus, a typical reaction to produce these novel carbonyl compounds is represented by the equation:
wherein R
a
, R
b
, R
c
, R
d
and R
e
are independently selected from the group consisting of H, alkyl groups and substituted alkyl groups having about 1 to 10
6
carbon atoms, alkenyl groups and substituted alkenyl groups having about 3 to 10
6
carbon atoms, wherein the substituents on the alkyl and/or alkenyl groups are selected from the group consisting of alkoxy, halogen, CN, OH, HO(CH
2
CH
2
O)
x
(X=1-10), acyl, acyloxy and aryl substituents. Q=HOH, MeOH, EtOH, or n-BuOH; n=0,1,>1; X or Y are selected from the group consisting of —OH; —OR
1
; NR
1
R
2
; R
1
; wherein R
1
has about 1 to about 18 carbon atoms,
wherein R
2
is hydrogen or any alkyl group of from about 1 to about 18 carbon atoms, —NR
3
R
4
wherein R
3
and R
4
are alkyl groups of from about 1 to about 18 carbon atoms; OR
5
wherein R
5
is hydrogen or an alkyl group having about 1 to about 18 carbon atoms, —COOR
6
wherein R
6
is hydrogen or an alkyl group having about 1 to about 18 carbon atoms, —CN, and —SR
7
wherein R
7
is an alkyl group having about 1 to about 18 carbon atoms. Typical monomers are ketomalonic acid, esters of ketomalonic acid including alkyl and aryl esters; other useful ketoacids are alpha keto succinic acid, diketo succinic acid, and any alpha ketohydrocarboic acid and alpha, beta-diketohydrocarboic acids and their ester and amide analogs which have a molecular weight of about 130 to 500. Useful ketones include dimethyl, diphenyl and di-tolyl tri- and tetraketones.
Especially preferred olefinic hydrocarbons are alkenes having from 8 to 30 carbon atoms and olefinic polymers containing an allylic hydrogen and having molecular weights ranging from about 500 to about 10,000,000. The olefinic hydrocarbons may, of course, be substituted with functionalities such as —CN, —OH, HO(CH
2
CH
2
O)
x
(x=1-10), alkoxy, halogen, and
wherein W═C, N; V═O, S, SO
2
; and X is selected from the group consisting of OH; —OR
1
, NR
1
R
2
; R
1
; wherein R
1
has about 1 to about 18 carbon atoms,
wherein R
2
is hydrogen or any alkyl and has about 1 to about 18 carbon atoms, —NR
3
R
4
wherein R
3
and R
4
has about 1 to about 18 carbon atoms, OR
5
wherein R
5
is hydrogen or an alkyl group having about 1 to about 18 carbon atoms, —COOR
6
wherein R
6
is hydrogen or an alkyl group having about 1 to about 18 carbon atoms, —CN and —SR
7
, wherein R
7
is an alkyl group having about 1 to about 18 carbon atoms. Typical substituted alkenes include oleic acid, oleyl alcohol, methyl oleate, 2-octadecenyl succinic anhydride, octadecenyl benzene, octadecenyl methyl ketone, octadecenyl phenyl sulfide, octadecenyl phenyl sulfone, octadecenyl chloride, octadecenyl phenol, chlorobutyl, polyisobutenyl succinic anhydride, and related functional olefins and polyolefins.
Among the preferred polymers are butyl rubber and EPDM polymers. The expression “butyl rubber” as employed in the specification and claims is intended to include copolymers made from a polymerization reaction mixture having therein from 70 to 99.5% by weight of an isobutylene and about 0.5 to 30% by weight of a conjugated multiolefin having from about 4 to 14 carbon atoms, e.g., isoprene. The resulting copolymer contains 85 to 99.8% by weight of combined isoolefin and 0.2 to 15% of combined multiolefin.
Butyl rubber generally has a Staudinger molecular weight as measured by GPC of about 20,000 to about 500,000, preferably about 25,000 to about 400,000, especially about 100,000 to about 400,000 and a Wijs Iodine No. of about 0.5 to 50, preferably 1 to 15. The preparation of butyl rubber is described in U.S. Pat. No. 2,356,128, which is incorporated herein by reference.
For the purposes of this invention, the butyl rubber may have incorporated therein from about 0.2 to 10% of combined multiolefin; preferably about 0.5 to about 6%, more preferably about 1 to about 4%, e.g., 2%.
Illustrative of such a butyl rubber is Exxon butyl 365 (Exxon Chemical Company), having a mole percent unsaturation of about 2.0% and a Mooney viscosity (ML, 1+3, 212° F.) of about 40 to 50.
Low molecular weight butyl rubbers, i.e., butyl rubbers having a viscosity average molecular weight of about 5,000 to 85,000, and a mole percent unsaturation of about 1 to about 5%, may be sulfonated to produce the polymers useful in this invention. Preferably, these polymers have a viscosity average molecular weight of about 25,000 to about 60,000.
The EPDM terpolymers are low unsaturated polymers having about 0.5 to about 10.0 wt. % olefinic unsaturation, more prefer
Infineum USA L.P.
Lipman Bernard
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