Use of eugenol polyethers and eugenol polyether siloxanes as wetting agents

Patent metadata

Field	Value
Publication number	US-9993786-B2
Application number	US-201615255931-A
Country	US
Kind code	B2
Filing date	Sep 2, 2016
Priority date	Sep 3, 2015
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

The present invention relates to compositions comprising eugenol polyethers and/or eugenol polyethers modified with siloxanes, and to the use of eugenol polyethers in polyether siloxanes based on these eugenol polyethers as wetting agents.

First claim

The invention claimed is:

1. A composition, comprising:
a) 0.5% to 1.5% by weight of at least one compound of formula (I) or at least one compound of formula (II);
b) 2% to 50% by weight of at least one pigment; and
c) 2% to 40% by weight of at least one binder;
d) 0.5% to 5% by weight of at least one wax;
e) 10% to 60% by weight of at least one solvent;
f) 1% to 10% by weight of at least one film-forming auxiliary;
g) 0.2% to 5% by weight of at least one rheology additive;
h) 0.05% to 2% by weight of at least one defoamer;
i) 0.1% to 10% by weight of at least one neutralizing agent; and
j) 0% to 10% by weight of a further component;
wherein the sum of all the components adds up to 100% by weight and all percentages by weight are based on a total weight of the composition;
wherein the at least one compound of the formula (I) is represented by:

wherein
a=1 to 1000;
b=0 to 1000;
c=0 to 1000;
d=0 to 1000;
e=1 to 10; and
f=0 to 500,
with the proviso that the sum of a, b, c, d and f is not less than 3;
groups with indices a, b, c, d, and f are freely permutable over a molecule chain, and neither of groups with indices c and d optionally follows itself or a respective other group; and
different monomer units of fragments with indices a, b and f are optionally in a blockwise structure with one another, wherein individual blocks also optionally occur multiple times and are optionally randomly distributed among one another, or are subject to a random distribution and further are freely permutable with one another, such that they are optionally arranged in any desired sequence, subject to a restriction that neither of the groups with the indices c and d optionally follows itself or the respective other group,
wherein
R 1 =independently a hydrogen radical or an alkyl group having 1 to 8 carbon atoms,
R 2 =independently a hydrogen radical, an alkyl group having 1 to 20 carbon atoms, or an aryl or alkaryl group,
or R 1 and one of R 2 optionally together form a ring comprising an atom to which R 1 and R 2 are bonded,
R 3 =independently a saturated or unsaturated, aliphatic or aromatic, hydrocarbyl radical having 2 to 30 carbon atoms, which optionally has further substitution,
each of R 4 and R 7 =independently a hydrogen or an organic radical, or
R 4 and/or R 7 are optionally absent, wherein, when R 4 and R 7 are absent, there is a C═C double bond in place of R 4 and R 7 ,
a bridging Z fragment is optionally present or absent,
wherein, in the absence of the bridging Z fragment,
each of R 5 and R 6 =independently a hydrogen or an organic radical, wherein, when R 4 is absent, R 5 is an alkylidene radical or when R 7 is absent, R 6 is an alkylidene radical;
wherein, in the presence of the bridging Z fragment,
each of R 5 and R 6 =a hydrocarbyl radical bridged cycloaliphatically or aromatically via the bridging Z fragment, wherein Z is a divalent alkylene or alkenylene radical which optionally has further substitution,
each of R 8 and R 9 =independently a hydrogen radical, an alkyl group having 1 to 20 carbon atoms, an aryl or alkaryl group or an alkoxy group,
R 10 =independently a hydrogen radical, an alkyl group having 1 to 8 carbon atoms, an ester group —C(O)—R 11 , an acetoacetate group —C(O)—CH 2 —C(O)—R 12 , a silyl ether group —Si(R 13 ) 3 , a urethane group —C(O)—N—(R 14 ) 2 or a phosphoric acid group —P(O)—(OR 19 ) 2 ,
each of R 11 , R 12 and R 13 =independently a linear or branched, saturated or unsaturated, optionally further substituted with an alkyl group having 1 to 30 carbon atoms, or an aryl or alkaryl group,
R 14 =independently a hydrogen, a linear or branched, saturated or unsaturated, optionally further-substituted with an alkyl group having 1 to 30 carbon atoms, or an aryl or alkaryl group,
R 18 =independently an allyl or 2-propenyl group, and
R 19 =independently a hydrogen, an alkyl group or a polyether radical,
and
wherein the at least one compound of the formula (II) is represented by:
M g M′ h M″ n D i D′ j D″ m T k Q l   (II),

with
M=[R 15 3 SiO 1/2 ];
M′=[R 16 R 15 2 SiO 1/2 ];
M″=[R 17 R 15 2 SiO 1/2 ];
D=[R 15 2 SiO 2/2 ];
D′=[R 16 R 15 SiO 2/2 ];
D″=[R 17 R 15 SiO 2/2 ];
T=[R 15 SiO 3/2 ];
Q=[SiO 4/2 ];
g=0-20;
h=0-20;
i=0-1000;
j=0-20;
k=0-20;
l=0-20;
m=0-20; and
n=0-20,
wherein the sum of g, h, i, j, k, l and m is not less than 3 and the sum of h and j≥1,
R 15 =independently a hydrocarbyl radical having 1-16 carbon atoms or a hydrogen,
R 16 =independently a polyether radical, wherein at least 10% of the polyether radical is an eugenol-based polyether radical, and
R 17 =independently a hydrocarbyl radical which has 1-16 carbon atoms and also comprises a heteroatom and optionally has further substitution.

2. The composition according to claim 1 , further comprising b) one or more fillers.

3. The composition according to claim 1 , wherein the eugenol-based polyether radical in R 16 corresponds to a radical of:

and a non-eugenol-based polyether radical in R 16 corresponds to a radical of:

4. The composition according to claim 1 , wherein the at least one solvent is at least one selected from the group consisting of water, ethanol, isopropanol and ethyl acetate.

5. The composition according to claim 2 , wherein the one or more pigments are at least one selected from the group consisting of Pigment White 6, Pigment Black 7, Pigment Blue 15:3, Pigment Blue 15:4, Pigment Red 57:1, Pigment Yellow 12, Pigment Yellow 13, Pigment Violet 23 and Pigment Green 7.

6. A method for applying a coating, comprising:
applying the composition of claim 1 as a wetting agent to a substrate.

7. The method according to claim 6 , wherein said substrate is a film, paper, card, cardboard, folding box, bag, wallpaper, sack, hygiene paper, drink carton, board, wood surface, metal surface, plastic surface, glass and/or ceramic.

8. The method according to claim 6 , wherein an eugenol-based polyether of the formula (I) is prepared by double metal cyanide catalysis.

9. The method according to claim 6 , wherein an eugenol-based polyether of the formula (I) is prepared by basic catalysis.

10. The method according to claim 6 , wherein a reaction product of an eugenol-based polyether with a siloxane of the formula (II) is prepared by reacting of an eugenol-based polyether of the formula (I) with a Si—H-functional siloxane.

Assignees

• Evonik Degussa Gmbh

Inventors

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

Classifications

• C08G65/337

  containing other elements (organic compounds containing halogens only as halides of a carboxyl group C08G65/332) · CPC title

• C08G65/2648

  Alkali metals or compounds thereof · CPC title

• C08G77/46 Primary

  containing polyether sequences · CPC title

• C08G65/3322

  acyclic · CPC title

• C09D11/03 Primary

  characterised by features other than the chemical nature of the binder · CPC title