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Compositions comprising a farnesene interpolymer

a technology of farnesene and polymer, which is applied in the direction of hydrocarbons, hydrocarbon purification/separation, synthetic resin layered products, etc., can solve the problem of rare terpene or isoprenoid compound polymerization in adhesive compositions

Inactive Publication Date: 2010-12-30
AMYRIS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, adhesive compositions comprising polymers derived from terpenes or isoprenoid compounds are rare, even rarer are polymers derived from isoprenoid compounds having at least 15 carbon atoms.

Method used

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  • Compositions comprising a farnesene interpolymer
  • Compositions comprising a farnesene interpolymer
  • Compositions comprising a farnesene interpolymer

Examples

Experimental program
Comparison scheme
Effect test

example 1

1,4-polyfarnesene Having a Mn of 105,000

[0228]To a dried three-neck reactor under argon atmosphere, a pre-dried solution comprising 92.29 g of β-farnesene in 13.7% in cyclohexane was added. n-Butyl lithium (1.85×10−3 mol, obtained from Acros, Morris Plains, N.J.) was added into the reactor as an initiator, and the reactor was heated at about 50° C. for about 19 hours, until all β-farnesene was consumed, monitored by UV-Vis spectroscopy. Example 1 was precipitated from the reaction mixture with a 1% solution of ethanol and t-butyl catachol (obtained from Sigma-Aldrich, St. Louis, Mo.). After drying in a vacuum oven at about 60° C. for about 2 hours, Example 1 was kept under vacuum for about 16 hours. Afterwards, Example 1, collected at 89.83 g (yield 97%), was stored in a refrigerator to prevent any crosslinking before characterization.

[0229]The progress of synthesizing Example 1 was monitored by the disappearance of β-farnesene, as measured by UV-Vis in the reaction mixture. FIG. 1 ...

example 2

1,4-polyfarnesene Having a Mn of 245,000

[0237]Example 2 is a 1,4-polyfarnesene having a Mn of about 245,000 g / mol. Example 2 was synthesized similarly according to the procedure for Example 1, except sec-butyl lithium was used as the initiator. The net weight of Example 2 was found to be 83.59 g (yield 71.4%). The yield is lower because aliquots were removed to monitor the progression of the reaction.

[0238]The molecular weight and polydispersity of Example 2 were determined by GPC. FIG. 9 shows the GPC curve of Example 2. The Mn, Mw, Mp, Mz, Mz+1, polydispersity, Mz / Mw, and Mz+1 / Mw of Example 2 are shown in Table 2. The number of farnesene units in Example 2 was calculated to be about 2000. Because of the increased molecular weight of Example 2, it had a higher level of entanglement and longer relaxation time than Example 1.

TABLE 2PropertiesExample 2Mn244,747 g / molMw457,340 g / molMp501,220 g / molMz768,187 g / molMz+11,132,362 g / mol  Polydispersity1.868622Mz / Mw1.679684Mz+1 / Mw2.475971

[023...

example 3

3,4-polyfarnesene

[0241]Example 3 was synthesized similarly according to the procedure for Example 1 except that n-butyl lithium (1.71×10−3 mol) was added in the presence of N,N,N′,N′-tetramethylethylenediamine (1.71×10−3 mol, TMEDA, obtained from Sigma-Aldrich, St. Louis, Mo.). The net weight of Example 3 was found to be 82.72 g (yield 97%).

[0242]The molecular weight and polydispersity of Example 3 were determined by GPC. FIG. 12 shows the GPC curve of Example 3. The two peaks in FIG. 12 indicated that two distinct weight fractions formed in Example 3. The Mn, Mw, Mz, Mz+1, polydispersity, Mz / Mw, and Mz+1 / Mw of Example 3 are shown in Table 3. The Mp of the first peak in FIG. 12 was about 97,165 g / mol. The Mp of the second peak in FIG. 12 was about 46,582 g / mol. The number of farnesene units in Example 3 was calculated to be about 240.

TABLE 3PropertiesExample 3Mn45,818 g / molMw47,644 g / molMz49,134 g / molMz+150,527 g / molPolydispersity1.039844Mz / Mw1.031269Mz+1 / Mw1.060509

[0243]FIG. 13 sho...

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Abstract

Provided herein are composition comprising a farnesene interpolymer. The farnesene interpolymer can be derived from a farnesene and at least one vinyl monomer. In some embodiments, the mole percent ratio of the farnesene to the at least one vinyl monomer is from about 1:4 to about 100:1. In certain embodiments, the farnesene is α-farnesene, β-farnesene or a combination thereof. In some embodiments, the at least one vinyl monomer is ethylene, an α-olefin such as styrene, or a substituted or unsubstituted vinyl halide, vinyl ether, acrylonitrile, acrylic ester, methacrylic ester, acrylamide or methacrylamide, or a combination thereof.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a continuation application of U.S. application Ser. No. 12 / 694,120, filed Jan. 26, 2010, which is a continuation application of U.S. application Ser. No. 12 / 507,801, filed Jul. 23, 2009, which claims the benefit of U.S. Provisional Patent Application Ser. No. 61 / 220,591, filed Jun. 26, 2009, each of which is incorporated herein by reference in its entirety.FIELD OF THE INVENTION[0002]This invention provides a composition comprising a farnesene interpolymer. The farnesene interpolymer can be derived from a farnesene and at least a vinyl monomer. The mole percent ratio of the farnesene to the at least one vinyl monomer can be from about 1:4 to about 100:1. This invention also provides articles comprising the composition.BACKGROUND OF THE INVENTION[0003]An adhesive is a substance capable of holding materials (e.g., adherends or substrates) together by surface attachment. Pressure sensitive adhesives (PSAs) generally are a...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61L15/58C08F136/20C08L23/18B32B23/08
CPCA61L15/58Y10T428/2878C08F36/22C08F290/06C08F297/02C08L47/00C08L51/003C08L53/005C09J147/00C09J151/003C09J153/005B32B7/12Y10T428/28Y10T428/2852C08L2666/02Y10T428/31899
Inventor MCPHEE, DEREK JAMES
Owner AMYRIS INC
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