Moisture-curing compositions

Patent metadata

Field	Value
Publication number	US-11834545-B2
Application number	US-201816957061-A
Country	US
Kind code	B2
Filing date	Dec 14, 2018
Priority date	Dec 22, 2017
Publication date	Dec 5, 2023
Grant date	Dec 5, 2023

Abstract

A method for producing polyurethanes containing alkoxysilane groups comprises the step of reacting a compound containing at least one NCO group with a compound containing at least one Zerewitinoff-active H atom in the presence of a catalyst component, wherein the compound containing at least one NCO group and/or the compound containing at least one Zerewitinoff-active H atom contain at least one alkoxysilane group, to obtain a polyurethane containing alkoxysilane groups. The invention also relates to a polymer containing alkoxysilane groups, a method for producing a curable polymer, a curable polymer, a cured polymer, and the use thereof. The polymers contain a complex of a lanthanide with at least one beta-diketonate ligand, preferably Yb(acac)3, and are free from organic tin compounds.

First claim

The invention claimed is:

1. A process for producing alkoxysilane-containing polyurethanes comprising the step of reacting
a compound containing at least one NCO group with
a compound containing at least one Zerewitinoff-active H atom
in the presence of a catalyst component,
wherein the compound containing at least one NCO group and/or the compound containing at least one Zerewitinoff-active H atom contain at least one alkoxysilane group,
to afford an alkoxysilane-containing polyurethane,
wherein
the catalyst component contains a complex of a lanthanoid with at least one beta-diketonate ligand and wherein
the lanthanoid is ytterbium (III) and the beta-diketonate ligand is obtained by deprotonation of hacac (acetylacetone), hacac-F 7 (perfluoroacetylacetone), hbfa (benzoyl-2-furanoylmethane), hbpp (1,3-bis(3-pyridyl)-1,3-propanedione), Hbtfac (benzoyltrifluoroacetone), hbzac (benzoylacetone), hdbbm (di(4-bromo)benzoylmethane), hdcm (d,d-dicampholylmethane), hdmbm (4,4′-dimethoxydibenzoylmethane), hdmh (2,6-dimethyl-3,5-heptanedione), hdnm (dinaphthoylmethane), hdpm (dipivaloylmethane), hdppm (di(perfluoro-2-propoxypropionyl)methane), hdtp (1,3-di(2-thienyl)-1,3 -propanedione), hfacam (3-(trifluoroacetyl)-d-camphor), hfdh (6,6,6-trifluoro-2,2-dimethyl-3,5-hexanedione), hfhd (1,1,1,2,2,6,6,7,7,7-decafluoro-3,5-heptanedione), hfod (6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedione), hftac (2-furyltrifluoroacetone), hhfac (hexafluoroacetylacetone), hhfbc (3-(heptafluorobutyryl)-d-camphor), hhfth (4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)-1,3 -hexanedione), hmfa (4-methylbenzoyl-2-furanoylmethane), hmhd (6-methyl-2,4-heptanedione), hntac (2-naphthoyltrifluoroacetone), hpop (3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2,4-pentanedione), hppa (3-phenyl-2,4-pentanedione), hpta (=htpm) (pivaloyltrifluoroacetone), hptp (1-phenyl-3-(2-thienyl)-1,3-propanedione), H(t-cam) (3-(tert-butylhydroxymethylene)-d-camphor), htfac (trifluoroacetylacetone), htfn (1,1,1,2,2,3,3,7,7,8,8,9,9,9-tetradecafluoro-4,6-nonanedione), hthd (=hdpm, htmhd) (2,2,6,6-tetramethyl-3,5-heptanedione), htnb (4,4,4-trifluoro-1-(2-naphtyl)-1,3-butanedione), htmod (2,2,6,6-tetramethyl-3,5-octanedione), htrimh (2,2,6-trimethyl-3,5-heptanedione), htod (2,2,7-trimethyl-3,5-octanedione), htta (2-thenoyltrifluoroacetone) or any desired mixture thereof,
the catalyst component is free from organic tin compounds and remains in the alkoxysilane-containing polyurethane, and
wherein the alkoxysilane-containing polyurethane in cured form has at least one of the following properties compared to a comparative polymer, wherein the respective samples have been stored for 14 days at 23° C. and 50% relative humidity before measurement:
Shore A hardness (DIN 53505): ≤90% of the comparative polymer;
percentage value of elongation at break (DIN EN 53504, tensile speed: 200 mm/min, S2 test specimen): ≥101% of the percentage value of the comparative polymer;
secant modulus (EN ISO 8339, 100% elongation): <90% of the comparative polymer;
and wherein the comparative polymer was produced in the same way as the cured alkoxysilane-containing polyurethane but with dibutyltin dilaurate in the same molar amount instead of the complex of the lanthanoid with at least one beta-diketonate ligand in the catalyst component.

2. The process as claimed in claim 1 , wherein the complex of a lanthanoid with at least one beta-diketonate ligand is Yb(acac) 3 .

3. The process as claimed in claim 1 , wherein the compound containing at least one NCO group contains at least one alkoxysilane group and in that the compound containing at least one Zerewitinoff-active H atom contains no alkoxysilane group.

4. The process as claimed in claim 1 , wherein the compound containing at least one NCO group contains no alkoxysilane group and wherein the compound containing at least one Zerewitinoff-active H atom contains at least alkoxysilane group.

5. The process as claimed in claim 4 , wherein the compound containing at least one Zerewitinoff-active H atom contains at least one primary or secondary amino group.

6. An alkoxysilane-containing polyurethane formed from a reaction mixture comprising a catalyst component, wherein the catalyst component contains a complex of a lanthanoid with at least one beta-diketonate ligand and is free from organic tin compounds,
wherein the lanthanoid is ytterbium (III) and the beta-diketonate ligand is obtained by deprotonation of hacac (acetylacetone), hacac-F 7 (perfluoroacetylacetone), hbfa (benzoyl-2-furanoylmethane), hbpp (1,3-bis(3-pyridyl)-1,3-propanedione), Hbtfac (benzoyltrifluoroacetone), hbzac (benzoylacetone), hdbbm (di(4-bromo)benzoylmethane), hdcm (d,d-dicampholylmethane), hdmbm (4,4′-dimethoxydibenzoylmethane), hdmh (2,6-dimethyl-3,5-heptanedione), hdnm (dinaphthoylmethane), hdpm (dipivaloylmethane), hdppm (di(perfluoro-2-propoxypropionyl)methane), hdtp (1,3-di(2-thienyl)-1,3 -propanedione), hfacam (3-(trifluoroacetyl)-d-camphor), hfdh (6,6,6-trifluoro-2,2-dimethyl-3,5-hexanedione), hfhd (1,1,1,2,2,6,6,7,7,7-decafluoro-3,5-heptanedione), hfod (6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedione), hftac (2-furyltrifluoroacetone), hhfac (hexafluoroacetylacetone), hhfbc (3-(heptafluorobutyryl)-d-camphor), hhfth (4,4,5,5,6,6,6-heptafluoro-1-(2-thienyl)-1,3 -hexanedione), hmfa (4-methylbenzoyl-2-furanoylmethane), hmhd (6-methyl-2,4-heptanedione), hntac (2-naphthoyltrifluoroacetone), hpop (3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2,4-pentanedione), hppa (3-phenyl-2,4-pentanedione), hpta (=htpm) (pivaloyltrifluoroacetone), hptp (1-phenyl-3-(2-thienyl)-1,3-propanedione), H(t-cam) (3-(tert-butylhydroxymethylene)-d-camphor), htfac (trifluoroacetylacetone), htfn (1,1,1,2,2,3,3,7,7,8,8,9,9,9-tetradecafluoro-4,6-nonanedione), hthd (=hdpm, htmhd) (2,2,6,6-tetramethyl-3,5-heptanedione), htnb (4,4,4-trifluoro-1-(2-naphtyl)-1,3-butanedione), htmod (2,2,6,6-tetramethyl-3,5-octanedione), htrimh (2,2,6-trimethyl-3,5-heptanedione), htod (2,2,7-trimethyl-3,5-octanedione), htta (2-thenoyltrifluoroacetone) or any desired mixture thereof,
wherein the alkoxysilane-containing polyurethane in cured form has at least one of the following properties compared to a comparative polymer, wherein the respective samples have been stored for 14 days at 23° C. and 50% relative humidity before measurement:
Shore A hardness (DIN 53505): ≤90% of the comparative polymer;
percentage value of elongation at break (DIN EN 53504, tensile speed: 200 mm/min, S2 test specimen): ≥101% of the percentage value of the comparative polymer;
secant modulus (EN ISO 8339, 100% elongation): ≤90% of the comparative polymer;
and wherein the comparative polymer was produced in the same way as the cured alkoxysilane-containing polyurethane but with dibutyltin dilaurate in the same molar amount instead of the complex of the lanthanoid with at least one beta-diketonate ligand in the catalyst component.

7. The polyurethane as claimed in claim 6 , wherein the polyurethane is obtained by a process comprising the step of reacting
a compound containing at least one NCO group with
a compound containing at least one Zerewitinoff-active H atom
in the presence of a catalyst component,
wherein the compound containing at least one NCO group and/or the compound containing at least one Zerewitinoff-active H atom contain at least one alkoxysilane group,
to afford the alkoxysilane-containing polyurethane,
wherein
the catalyst component contains a complex of a lanthanoid with at least one beta-diketonate ligand and wherein
the catalyst component is free from organic tin compounds.

8. A process for producing a curable polymer, wherein the process comprises the step of contacting a polyurethane as claimed in claim 6 with a siloxane condensation catalyst.

9. The

Assignees

• Covestro Deutschland Ag

Inventors

• Thiebes Christoph
• Stempfle Florian
• Laas Hans-Josef
• Baumbach Beate
• Nattke Ute

Classifications

• C08G18/3893 Primary

  containing silicon · CPC title

• B01J31/2234

  Beta-dicarbonyl ligands, e.g. acetylacetonates · CPC title

• C08G18/222 Primary

  metal compounds not provided for in groups C08G18/225 - C08G18/26 · CPC title

• B01J2531/38

  Lanthanides other than lanthanum · CPC title

• C08G2150/00

  Compositions for coatings · CPC title