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 Insoluble polyalkyl phosphonium salt resins having carbon-carbon crosslinked backbone

Details
Inventors: Rakshys, Jr., Joseph W.; McKinley, Suzanne V.;
Assignee: The Dow Chemical Company (Midland, MI)
Primary Examiner: Schofer; Joseph L.
Assistant Examiner: Kulkosky; Peter F.
Attorney, Agent or Firm: Baker; Glwynn R.

Novel resins having a carbon-to-carbon backbone, cross-linked with carbon-to-carbon linkages and having a plurality of ##STR1## pendant groups, wherein m is an integer from 1 to 6, preferably 3, each R is an alkyl group of from 1 to 10 C atoms, preferably 2-6 C atoms, and X is an alkoxyl or aryloxy group, an OH- group or a hydrocarbyl COO- group or a CN-, NO.sub.3 -, SO.sub.4 -, or ClO.sub.4 - group and a method of their preparation are disclosed. The cross-linked resins are useful as resins and as insoluble catalysts for preparation of glycol ethers from alcohols and epoxides, and for polymerizing epoxides.

DETAILED DESCRIPTION OF THE INVENTION The cross-linked polymers have a carbon-to-carbon main polymer chain or backbone and cross-links formed by the addition copolymerization of a mono-olefinically unsaturated monomer and a polyolefinically unsaturated monomer.
The pendant groups on the main polymer chain or backbone can contain a tetraalkylphosphonium salt group.
The latter on the main polymer chain conforms graphically to the structures ##STR2## where R" is H or a methyl group, R is a saturated unsubstituted aliphatic hydrocarbon group of 1 to 10 C atoms, preferably 2 to 6 C atoms, X is an OH or an OR'" group where R'" is a hydrocarbyl group of 1 to 10 C atoms free of aliphatic unsaturation, and preferably such hydrocarbyl group having 1 to 6 C atoms, and most preferably an alkyl group of 1 to 6 C atoms, a cycloalkyl or a phenyl group, a CN.
sup.
-, NO.
sub.
3.
sup.
-, SO.
sub.
4.
sup.
.
dbd.
or a CIO.
sub.
4.
sup.
- group, R' is H, CN or one or more alkyl groups of 1 to 4 C atoms and preferably the total number of C atoms in all alkyl groups represented by R' is not greater than 4 C atoms, n is an integer from 1 to 3, m is an integer from 1 to 6, preferably 3 to 4, and Z is H or a CO.
sub.
2 R'" group having R'" as defined above or as--(CH.
sub.
2).
sub.
m P.
sup.
+ (R).
sub.
3 X.
sup.
- and y is an integer greater than 1.
The moiety represented by y constitutes 20-99 mole percent of the entire polymer.
The main polymer chain comprises a carbon-to-carbon backbone which may have alkyl or other substitution thereon in which the substituent is not reactive with organolithium compounds, alkali metal alkoxides or hydroxide groups.
The polymers are cross-linked through carbon-to-carbon bonds by the use of a polyunsaturated monomer during polymerization.
Representative cross-linking agents include the divinyl benzenes, lower alkyl substituted divinyl benzenes, trivinyl benzenes, diisopropenyl benzenes, triisopropenyl benzenes, and lower alkyl substituted derivatives thereof in which the substituent has up to 4 carbon atoms; divinyl cyclohexane, trivinyl cyclohexane or any other polyolefinically unsaturated monomer which copolymerizes with the styrene or acrylic ester or maleic monomer or both



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