Functionalized ethylene/vinyl or vinylidene aromatic...

Details Functionalized ethylene/vinyl or vinylidene aromatic... Functionalized ethylene/vinyl or vinylidene aromatic...

1999-02-04

2001-11-06

Wu, David W. (Department: 1713)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S308000, C526S314000, C526S318100, C526S324000, C526S325000, C526S307400, C526S282000, C525S333300, C525S333400, C525S333500, C525S333600, C525S379000, C525S383000, C525S343000, C525S279000, C525S268000, C525S309000, C525S311000

Reexamination Certificate

active

06313252

ABSTRACT:

FIELD OF THE INVENTION
The present invention pertains to functionalized interpolymers of ethylene or one or more &agr;-olefin monomers, or combinations thereof, with one or more vinyl or vinylidene aromatic monomers or one or more sterically hindered aliphatic or cycloaliphatic vinyl or vinylidene monomers, or combination thereof, and methods of preparing the interpolymers.
BACKGROUND OF THE INVENTION
The generic class of materials of &agr;-olefin/vinyl or vinylidene monomer substantially random interpolymers, including materials such as substantially random &agr;-olefin/vinyl aromatic monomer interpolymers, and their preparation, are known in the art, such as described in U.S. Pat. No. 5,703,187 (EP 416 815 A2), the contents of which are herein incorporated by reference.
These materials offer a wide range of material structures and properties which makes them useful for varied applications, such as, for example, asphalt modifiers or as compatibilizers for blends of polyethylene and polystyrene, as described in U.S. Pat. No. 5,460,818 the contents of which are herein incorporated by reference.
The structure, thermal transitions and mechanical properties of substantially random interpolymers of ethylene and styrene containing up to about 50 mole percent styrene have been described (see Y. W. Cheung, M. J. Guest;
Proc. Antec '
96 pp. 1634-1637) the contents of which are herein incorporated by reference. These polymers are found to have glass transitions in the range of −20° C. to +35° C., and show no measurable crystallinity above about 25 mole percent styrene incorporation, that is they are essentially amorphous.
Although of utility in their own right, industry is constantly seeking to improve the applicability of the substantially random interpolymers. To perform well in certain applications, it may be desirable to modify the properties of these interpolymers. One method of modifying the properties of the substantially random interpolymers is to functionalize the vinyl or vinylidene group subsequent to interpolymer formation. WO 97/05175 describes functionalized styrene polymers and copolymers and WO 96/16096 describes alpha olefin/para-alkyl styrene copolymers and functionalized copolymers thereof, the contents of both of which are herein incorporated by reference.
Thus, it would be advantageous to discover a method of modifying the conventional substantially random interpolymers. Further, it would be advantageous if such a method could be applied to a variety of interpolymers to form a variety of new, modified interpolymers.
BRIEF SUMMARY OF THE INVENTION
The present invention relates to a functionalized substantially random interpolymer comprising;
(a) from 0 to about 64.95 mole percent of repeating units represented by the following formula (I);
wherein Y is independently selected from the group consisting of hydrogen, substituted and unsubstituted alkyl radicals, benzyl radicals, aryl radicals, and aralkyl radicals containing up to 18 carbon atoms, —X, —CH
2
X, —C(O)R
6
, —(Z)—CO
2
H, —(Z)—SO
3
H, —NO
2
, —C(O)—OR
6
, —(Z)—OR
6
, —N(R
6
)
2
, —(Z)—N(R
6
)
2
, —P(OR
6
)
2
, —(Z)—P(OR
6
)
2
, —P(R
6
)
2
, —(Z)—P(R
6
)
2
, —P(O)(R
6
)
2
, —(Z)—P(O)(R
6
)
2
, —P(O)(OR
6
)
2
, —(Z)—P(O)(R
6
)
2
, —(Z)—SR
6
, —CN, —(Z)—CN, —CO
2
H, —C(O)N(R
6
)
2
, —(Z)—C(O)N(R
6
)
2
, ionomeric salts of —CO
2
−
, —(Z)—CO
2
−
, —(Z)—SO
3
−
, —N
+
(R
6
)
3
, —(Z)—N
+
(R
6
)
3
, —P
+
(R
6
)
3
, —(Z)—P
+
(R
6
)
3
, —(Z)—S
+
(R
6
)
2
, or combinations thereof, R
1
is selected from the group of radicals consisting of hydrogen and alkyl radicals containing from about 1 to about 4 carbon atoms; R
2
is independently selected from the group of radicals consisting of hydrogen and alkyl radicals containing from about 1 to about 4 carbon atoms; R
6
is independently selected from the group of radicals consisting of hydrogen, substituted or unsubstituted alkyl radicals containing from about 1 to about 18 carbon atoms, and substituted or unsubstituted aryl radicals; X is a halogen; and Z is alkylene or arylene; and n has a value from zero to about 4;
(b) from about 0.05 to about 65 mole percent of repeating units represented by the following formula (II);
wherein Y, R
1
, R
2
, n, and X are as described for I with the proviso that at least one Y is not hydrogen or a substituted or unsubstituted alkyl radical;
(c) from 0 to about 25 mole percent of repeating units represented by the following formula (III);
wherein R
1
and R
2
are as described for I and A
1
is a sterically bulky, aliphatic or cycloaliphatic substituent of up to about 20 carbons or R
2
and A
1
together form a ring system wherein the ring system formed by A
1
and R
2
is optionally substituted with one or more substituents selected from alkyl radicals having from 1 to 18 carbon atoms, —X, —CH
2
X, —C(O)R
6
, —(Z)—CO
2
H, —(Z)—SO
3
H, —NO
2
, —C(O)OR
6
, —(Z)—OR
6
, —N(R
6
)
2
, —(Z)—N(R
6
)
2
, —P(OR
6
)
2
, —(Z)—P(OR
6
)
2
, —P(R
6
)
2
, —(Z)—P(R
6
)
2
, —P(O)(R
6
)
2
, —(Z)—P(O)(R
6
)
2
, —P(O)(OR
6
)
2
, —(Z)—P(O)(R
6
)
2
, —(Z)—SR
6
, —CN, —(Z)—CN, —CO
2
H, —C(O)N(R
6
)
2
, —(Z)—C(O)N(R
6
)
2
, ionomeric salts of —CO
2
−
, —(Z)—CO
2
−
, —(Z)—SO
3
−
, —N
+
(R
6
)
3
, —(Z)—N
+
(R
6
)
3
, —P
+
(R
6
)
3
, —(Z)—P
+
(R
6
)
3
, —(Z)—S
+
(R
6
)
2
, and mixtures thereof wherein R
6
, X, and Z are as defined above for I; and
(d) from 35 to 99.95 mole percent of repeating units represented by the following formula (IV);
wherein R
3
and R
4
are selected from the group consisting of hydrogen and alkyl radicals having from 1 to 18 carbon atoms, with the proviso that R
3
and R
4
are different alkyl radicals.
The invention also relates to processes of making the functionalized polymers described herein.
DETAILED DESCRIPTION OF THE INVENTION
The following definitions are used throughout the disclosure. The term “interpolymer” is used herein to indicate a polymer wherein at least two different monomers are polymerized to make the interpolymer. This includes copolymers, terpolymers, etc.
The term “repeating unit” as employed herein means a combination of atoms which may be represented by a formula wherein the formula occurs more than once in a given interpolymer chain.
The term “ionomer” or “ionomeric salt” as employed herein means a polymer containing interchain ionic bonding. Ionomeric salts are ionically crosslinked thermoplastics generally obtained by neutralizing a copolymer containing pendant acid groups, for example, carboxylic acid groups, with an ionizable compound, for example, a compound of the monovalent, divalent and/or trivalent metals of Group I, II, IV-A and VIIIB of the periodic table of the elements. Preferred ionomeric salts are obtained by reacting the functionalized interpolymers with a sufficient amount of base as to neutralize at least some portion of the acid groups, preferably at least 5 percent by weight and preferably from 20 to 100 percent by weight, of the acid groups present. Suitable bases include amines, salts of substituted and unsubstituted ammonium and phosphonium ions and salts of metal ions including Na
+
, K
+
, Li
+
, Cs
+
, Rb
+
, Hg
+
, Cu
+
, Be
+2
, Mg
+2
, Ca
+2
, Sr
+2
, Cu
+2
, Cd
+2
, Hg
+2
, Sn
+2
, Pb
+2
, Fe
+2
, Co
+2
, Ni
+2
, Zn
+2
, Al
+3
, Sc
+3
, and Y
+3
. Basic salts of preferred metals suitable for neutralizing the copolymers used herein are the alkali metals, particularly, cations such as sodium, lithium and potassium and alkaline earth metals, in particular, cations such as sodium, calcium, magnesium and zinc. However also contemplated in the present invention are ionomeric salts in which the polymer bears a positive charge and the counterion bears the negative charge. Both organic and inorganic anions are included in the possible ionomeric salts where the polymer bears a positive charge, said anions including, but not limited to carboxylate, alkoxide, halide, borate,

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