Acrylate-terminated urethane polybutadienes from low-monomer 1:1 monoadducts from reactive olefinic compounds and diisocyanates and hydroxy-terminated polybutadienes for liquid optically clear adhesives (LOCAs)

Patent metadata

Field	Value
Publication number	US-10407546-B2
Application number	US-201816177878-A
Country	US
Kind code	B2
Filing date	Nov 1, 2018
Priority date	Sep 5, 2014
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

The present invention relates to a process for producing hydrosilylatable, eugenol-based polyethers, to the conversion thereof into polyether siloxanes and also to the products that may be produced by this process and to the use of said products as surfactants.

First claim

The invention claimed is:

1. A product of formula (I)

where
a=1 to 1000,
b=0 to 1000,
c=0 to 1000,
d=0 to 1000,
e=1 to 10,
f=0 to 500,

with the proviso that the sum of a+b+c+d+f is not less than 3 and
with the proviso that the groups with the indices a, b, c, d, and f are freely permutable over the molecule chain and neither of the groups with the indices c and d may follow itself or the respective other group
and with the proviso that the different monomer units and the fragments with the indices a, b and f may be in a blockwise structure with one another, where individual blocks may also occur multiple times and may be randomly distributed among one another, or else are subject to a random distribution and further are freely permutable with one another, in the sense that they may be arranged in any desired sequence, subject to the restriction that neither of the groups with the indices c and d may follow itself or the respective other group,
and where
R 1 =independently at each occurrence a hydrogen radical or a C 1 -C 8 alkyl group,
R 2 =independently at each occurrence a hydrogen radical, a C 1 -C 20 alkyl group, an aryl or alkaryl group,
or R 1 and one of the radicals R 2 may together form a ring which includes the atoms to which R 1 and R 2 are bonded,
R 3 =independently at each occurrence a saturated or unsaturated, aliphatic or aromatic, hydrocarbon radical comprising 2 to 30 carbon atoms, which is optionally further substituted,
R 4 , R 7 =independently at each occurrence hydrogen and/or an organic radical, or else optionally R 4 and/or R 7 may be absent, where, when R 4 and R 7 are absent, there is a C═C double bond in place of the radicals R 4 and R 7 ,
the bridging fragment Z may be present or absent;
when the bridging fragment Z is absent, then
R 5 , R 6 =independently at each occurrence hydrogen and/or an organic radical, where,
when one of the radicals R 4 or R 7 is absent, the respective geminal radical (i.e. R 5 when R 4 is absent and R 6 when R 7 is absent) is an alkylidene radical;
when the bridging fragment Z is present, then
R 5 , R 6 =hydrocarbon radicals which are bridged cycloaliphatically or aromatically via fragment Z, where Z represents a divalent alkylene or alkenylene radical which may be further substituted,
R 10 =independently at each occurrence a hydrogen radical or a C 1 -C 8 alkyl group or an ester group —C(O)—R 11 or an acetoacetate group —C(O)—CH 2 C(O)—R 12 or a silyl ether group —Si(R 3 ) 3 or a urethane group —C(O)—N—(R 14 ) 2 where
R 11 , R 12 , R 13 =independently at each occurrence a linear or branched, saturated or unsaturated, optionally further substituted C 1 -C 30 alkyl group, an aryl or alkaryl group, and
R 14 =independently at each occurrence hydrogen and/or a linear or branched, saturated or unsaturated, optionally further substituted C 1 -C 30 alkyl group, an aryl or alkaryl group.

2. The product according to claim 1 , wherein the product is obtained by
reacting at least one epoxide with eugenol in the presence of a double metal cyanide catalyst.

3. The product according to claim 1 , wherein in the formulae (I), the fragment with the index b is at least one member selected from the group consisting of methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, tert-butyl glycidyl ether, 2-pentyl glycidyl ether, 3-pentyl glycidyl ether, 2-methylbutyl glycidyl ether, 3-methylbutyl glycidyl ether, 2-methyl-2-butyl glycidyl ether, 3-methyl-2-butyl glycidyl ether, 2,2-dimethylpropyl glycidyl ether, hexyl glycidyl ether, heptyl glycidyl ether, octyl glycidyl ether, 2-ethylhexyl glycidyl ether, 2-propylheptyl glycidyl ether, 2-butyloctanyl giycidyl ether, 2-methylundecyl glycidyl ether, 2-propylnonyl glycidyl ether, 2-ethyldecyl glycidyl ether, 2-pentylheptyl glycidyl ether, 2-hexyldecyl glycidyl ether, 2-butyltetradecyl glycidyl ether, 2-dodecylhexadecyl glycidyl ether, 2-tetradecyloctadecyl glycidyl ether, 3,5,5-trimethylhexyl glycidylether, isononanyl glycidyl ether, isotridecyl glycidyl ether, isomyristyl glycidyl ether, isostearyl glycidyl ether, 2-octyldodecyl glycidyl ether, triphenylmethyl glycidylether, C(O)—(CH 2 ) 5 —C—(CH 3 ) 3 glycidyl ether, C 12 /C 14 -alkyl glycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, tert-butylphenyl glycidyl ether, benzyl glycidyl ether, 3-glycidyloxypropyl-trimethoxysilan, 3-glycidyloxypropyltriethoxysilane, 3-glycidyloxypropyltripropoxysilane, 3-glycidyloxypropyltriisopropoxysilane, bis(3-glycidyloxypropyl)dimethoxysilane, bis(3-glycidyloxypropyl)diethoxysilane, 3-glycidyloxyhexyltrimethoxysilane, 3-glycidyloxyhexyltriethoxysilane, 3-glycidyloxypropylmethyldimethoxysilane, and 3-glycidyloxypropylethyldiethoxysilane.

4. A method of dispersing a compound in a condensed fluid medium, the method comprising:
mixing the compound and a product according to claim 1 in a condensed fluid medium.

5. The product according to claim 1 , wherein
a=4 to 50,
b=0 to 50,
c=0 to 50,
d=0 to 50,
f=0 to 100,
R 1 =independently at each occurrence a hydrogen,
R 2 =independently at each occurrence is hydrogen, methyl, or ethyl,
or R 1 and one of the radicals R 2 may together form a ring comprising 5 to 8 carbon atoms,
R 1 =independently at each occurrence a saturated or unsaturated, aliphatic or aromatic, hydrocarbon radical comprising 2 to 24 carbon atoms, which is optionally further substituted,
R 4 , R 7 =independently at each occurrence is selected from the group consisting of alkyl, alkenyl, alkylidene, alkoxy, aryl and aralkyl, or else optionally R 4 and/or R 7 may be absent, where, when R 4 and R 7 are absent, there is a C═C double bond in place of the radicals R 4 and R 7 ,
the bridging fragment Z may be present or absent;
when the bridging fragment Z is absent, then
R 5 , R 6 =independently at each occurrence is selected from the group consisting of alkyl, alkenyl, alkylidene, alkoxy, aryl or aralkyl, where, when one of the radicals R 4 or R 7 is absent, the respective geminal radical (i.e. R 5 when R 4 is absent and R 6 when R 7 is absent) is methylidene (═CH 2 ).

Assignees

• Evonik Degussa Gmbh

Inventors

• Lobert Matthias
• Ferenz Michael
• Roland Katrin
• Schierle Thorsten

Classifications

• C08G65/2645

  Metals or compounds thereof, e.g. salts · CPC title

• C08G77/46

  containing polyether sequences · CPC title

• C08G65/2612

  containing aromatic or arylaliphatic hydroxyl groups · CPC title

• C08G65/34

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• C08G65/2663

  Metal cyanide catalysts, i.e. DMC's · CPC title