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Butadiene polymers having terminal functional groups

a technology of terminal functional groups and butadiene polymers, which is applied in the field of butadiene polymers having terminal functional groups, can solve problems such as unexpectedly affecting the viscosity of polymers

Inactive Publication Date: 2007-05-08
KRATON POLYMERS US LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text describes how adding different amounts of butadiene to hydrogenated butadiene polymers with terminal functional groups can affect their viscosity. The researchers found that polymers with between 30% and 70% of 1,2-addition had the lowest viscosity. The polymers can be used without solvents at room temperature and have a peak molecular weight between 500 and 20,000.

Problems solved by technology

Applicants have discovered that varying the amount of 1,2-addition of butadiene in hydrogenated butadiene polymers having terminal functional groups significantly and unexpectedly impacts the viscosity of the polymers.

Method used

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  • Butadiene polymers having terminal functional groups

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0031]A linear hydrogenated butadiene polymer having about two terminal hydroxyl groups per molecule, a peak molecular weight of 2900, as determined by Gel Permeation Chromatography (GPC) using polybutadiene standards, and a 1,2-addition of 40%, as determined by a Nuclear Magnetic Resonance (NMR) technique, was prepared as described below. The linear butadiene precursor polymer was synthesized using a diinitiator for the polymerization of 1,3-butadiene. The living polymer chain ends were capped using ethylene oxide to afford the precursor polymer having terminal, primary hydroxyl functionality. This polymer was hydrogenated using a Ni / Al catalyst.

[0032]To synthesize the diinitiator moiety, 100 pounds of cyclohexane, 6 pounds of diethyl ether, and 1564 g of m-diisopropenylbenzene (DIPB) (97% wt DIPB, 9.6 moles) were combined with stirring in a sealed, steel reactor vessel under an inert, nitrogen atmosphere. Impurities that might interfere with anionic polymerization were removed by ...

examples 2-5

[0040]The procedure of Example 1 was modified to prepare a series of hydrogenated butadiene polymers having about two terminal hydroxyl groups per molecule, different peak molecular weights, and different amounts of 1,2-addition. The molecular weight of the diol was adjusted by varying the diinitiator to monomer ratio during polymerization of the butadiene. The 1,2-addition was varied by adjusting the diethyl ether content of the solvent before polymerization and by adjusting the temperature at which the butadiene polymerization was conducted. Higher levels of 1,2-addition were favored by higher levels of diethyl ether and lower reaction temperatures. Synthesis in this way afforded products with the structures of Table 1 and properties of Table 2.

[0041]

TABLE 11,2-EO CappingHydro-ExampleMWAdditionEfficiencygenationNumber(Peak)(%)(%)(%)1290040829523900419598350604092994350052879853970488599POLYTAIL HA1230084NA 993NISSO GI-20002238084NA 983POLYTAIL H1372022NANA1Polymer produced by Mits...

example 6 (

HYPOTHETICAL)

[0046]A hydrogenated butadiene polymer having terminal hydroxyl groups is prepared as described in Example 1 except that the ratio of diinitiator to butadiene monomer is adjusted to provide a peak molecular weight of 10000.

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Abstract

Hydrogenated butadiene polymers having terminal functional groups have minimum viscosity at any molecular weight when the 1,2-addition is between 30% and 70% Hydrogenated butadiene polymers having about two terminal hydroxyl groups per molecule have surprisingly lower viscosities at 30% to 70% 1,2-addition than similar polymers having either higher or lower amounts of 1,2-addition. The polymers are useful in making coatings, sealants, binders, and block copolymers with polyesters, polyamides, and polycarbonates.

Description

[0001]This is a division of application Ser. No. 07 / 938,917, filed Aug. 31, 1992.BACKGROUND OF THE INVENTION[0002]This invention relates to manufacture of low viscosity hydrogenated butadiene polymers having terminal functional groups and use of the low viscosity polymers to make coatings and other high molecular weight polymers.[0003]Anionic polymerization of conjugated dienes with lithium initiators, such as sec-butyllithium, and hydrogenation of residual unsaturation has been described in many references including U.S. Pat. No. Re. 27,145 which teaches a relationship between the amount of 1,2-addition of butadiene (35% to 55%) and the glass transition temperatures of the hydrogenated butadiene polymers.[0004]The termination of living anionic polymers to form functional end groups is described in U.S. Pat. Nos. 4,417,029, 4,518,753, and 4,753,991. Of particular interest for the present invention are terminal hydroxyl, carboxyl, phenol, epoxy, and amine groups.[0005]For unsaturated...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C08F8/00C08C19/44C08F136/06C08G18/08C08G18/62C08G18/81C08G63/00C08G64/18C08G69/00C08G81/02C08L15/00C08L19/00
CPCC08C19/44C08F136/06C08G18/0823C08G18/6208C08G18/8175C08G63/00C08G64/18C08G69/00C08G81/024C08L15/00C08L19/006C08F4/488C08G18/62
Inventor HANDLIN, JR., DALE L.GOODWIN, DANIEL E.WILLIS, CARL L.ST. CLAIR, DAVID J.WILKEY, JOHN D.MODIC, MICHAEL J.STEVENS, CRAIG A.
Owner KRATON POLYMERS US LLC