IP Library Granted Patent US 10,329,375
Granted Patent B2
US 10,329,375 · App. 15/984,139 · Granted Jun 25, 2019

Hydrophilic, alkoxysilane-containing isocyanurates

Inventors: Wiebke Stache (Herten, DE); Tobias Unkelhäußer (Dülmen, DE); Iris Brückner (Dorsten, DE); Sabine Naumann (Herne, DE); Marita Drüner (Reken, DE); Judith Schoder (Haltern am See, DE)
Assignee: Evonik Degussa GmbH
C08G18/837C07F7/18C07F7/1804C07F7/1892C08G18/1875C08G18/283C08G18/73C08G18/778C08G18/792C08G18/809C09D175/04C09D175/08
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Quick Facts
Patent No.
US 10,329,375
App. No.
15/984,139
Granted
Jun 25, 2019
Kind
B2
Abstract

A coating or plastics formulation contains a reaction product of at least one alkoxysilane-containing isocyanurate of the formula (I) with at least one hydrophilizing agent of the formula BOH which has at least one OH group, wherein R 1 , R 2 and R 3 in each case independently of one another are a linear or branched and/or cyclic C1-C8 alkylene radical, R′, R″ and R′″ in each case independently of one another are a linear or branched and/or cyclic C1-C8 alkyl radical, and B is a hydrophilic radical.

Claims (55)

1. An alkoxysilane-containing isocyanurate of formula (II)

wherein

R 1 , R 2 and R 3 are, in each case independently of one another, a linear, a branched, or a cyclic C 1 -C 8 alkylene radical,

R′, R″ and R′″ are, in each case independently of one another, a linear, a branched, or a cyclic C 1 -C 8 alkyl radical,

j, k, l, are each independently of one another, 0, 1, 2 or 3,

1≤j+k+l≤7, and

radical —OB is a polyalkylene oxide polyether alkoxy radical, or

radical —OB has formula —O{(X)-(y) a -(Z)},

wherein

radical X derives

from a hydroxypolyethylene glycol ether of empirical formula HO(CH 2 CH 2 O) n T 1 , wherein n=2-100, wherein T 1 =H or C 1 -C 6 alkyl, or

from a hydroalkylcarboxylic acid, or

from a hydroxypolyethersulfonic acid,

a is 0 or 1,

radical y, if present, derives from a di- or polyisocyanate, from a di- or polycarboxylic acid derivative, from a di- or polyepoxide, from a mono- or polyalkoxysilane, from an epoxyisocyanate, from an epoxyalkoxysilane or from an isocyanatosilane, and

radical Z derives

from a hydroxy-terminated polyether of formula

TO(CTHCH 2 O) n (CH 2 CH 2 O) p T′, wherein T=—(CH 2 ) m CH 3 , n and m independently of one another=0-20, p=0-5 wherein n is greater than or equal to 4 times p, and T′=H or C 1 -C 18 alkyl, or

from one or more than one hydroxyhydrocarbon having 1-18 carbon atoms, which is optionally branched and/or optionally contains rings and/or heteroatom(s), or

from an alkylene oxide having at least four carbon atoms which is optionally branched and/or optionally contains rings.

2. The isocyanurate according to claim 1 , wherein

R 1 =R 2 =R 3 =—CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —, and

R′, R″ and R′″ are identical and selected from the group consisting of —CH 3 , —CH2CH 3 , and —CH(CH 3 )CH 3 .

3. The isocyanurate according to claim 2 , wherein

R 1 =R 2 =R 3 =—CH 2 CH 3 CH 2 — and

R′, R″ and R′″ are identical and selected from the group consisting of —CH 3 and —CH 2 CH 3 .

4. The isocyanurate according to claim 1 , wherein

the polyalkylene oxide polyether alkoxy radical is a polyethylene glycol monomethyl ether alkoxy radical having on average 5 to 30 ethylene oxide units.

5. The isocyanurate according to claim 1 , wherein

radical X derives

from a hydroxypolyalkylene glycol ether of empirical formula HO(CH 2 CH 2 O) n T 1 wherein n=2-100, where T 1 =H or C 1 -C 6 alkyl, and

radical Z has formula -G-D-H, wherein

G is a structural element of formula (III)

 wherein T 5 independently at each occurrence is a saturated, unsaturated, branched or unbranched, substituted or unsubstituted hydrocarbon radical having at least two carbon atoms,

 and w is greater than or equal to one;

D is an oxyethylene radical or oxypropylene radical of formula —(CH 2 CHT 6 O) v wherein v is greater than or equal to 0, and T 6 =—H or —CH 3 ; and

H=hydrogen.

6. A process for preparing the isocyanurate according to claim 1 , the process comprising:

reacting at least one alkoxysilane-containing isocyanurate of formula (I)

with at least one hydrophilizing agent of formula BOH, which has at least one OH group,

wherein

R 1 , R 2 and R 3 are, in each case independently of one another, a linear, a branched, or a cyclic C 1 -C 8 alkylene radical,

R′, R″ and R′″ are, in each case independently of one another, a linear, a branched, or a cyclic C 1 -C 8 alkyl radical, and

B is a hydrophilic radical.

7. The process according to claim 6 , wherein

the alkoxysilane-containing isocyanurate of formula (I) and the hydrophilizing agent BOH are present in a (I)/BOH molar ratio of from 15:1 to 1:7.

8. A coating or plastics formulation, a crosslinker, an emulsifier, an admixture for mineral building materials and/or an adjuvant for aqueous polyurethane dispersions, comprising:

the isocyanurate according to claim 1 .

9. A coating or plastic formulation, comprising:

the isocyanurate according to claim 1 .

10. A coating or plastic formulation according to claim 9 , further comprising:

at least one isocyanurate of formula (I)

wherein

R 1 , R 2 and R 3 are, in each case independently of one another, a linear, a branched, or a cyclic C 1 -C 8 alkylene radical, and

R′, R″ and R′″ are, in each case independently of one another, a linear, a branched, or cyclic C 1 -C 8 alkyl radical.

Assignments (2)
CHANGE OF NAME Recorded Nov 18, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051045/0872 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2018
From: STACHE, WIEBKE; UNKELHÄUSSER, TOBIAS; BRÜCKNER, IRIS; NAUMANN, SABINE; DRÜNER, MARITA; SCHODER, JUDITH
To: EVONIK DEGUSSA GMBH
Reel/Frame 046340/0522 →
Priority Claims (1)
EP 17172009 · May 19, 2017 · regional
Continuity (1)
Related Publication 20180334532A1 · Nov 22, 2018