Method for preparing a mixed silane-terminated polymer

Patent metadata

Field	Value
Publication number	US-11795266-B2
Application number	US-202017611931-A
Country	US
Kind code	B2
Filing date	May 25, 2020
Priority date	May 27, 2019
Publication date	Oct 24, 2023
Grant date	Oct 24, 2023

Abstract

The present invention relates to a process for preparing a mixed silane-terminated polymer by reacting a polyol component A) with a diisocyanate component B) comprising 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate), at least one isocyanatosilane C) and an aminosilane E), in which the urethanization reaction is carried out in the presence of at least one catalyst D) which is free of organically bonded tin. The invention further relates to the use of the polymers thus obtained.

First claim

The invention claimed is:

1. A process for preparing a mixed silane-terminated polymer by reacting a polyol component A) with a diisocyanate component B) comprising isophorone diisocyanate, with at least one isocyanatosilane C) and with an aminosilane E), in which a urethanization reaction is carried out in the presence of at least one catalyst D) which is free of organically bonded tin,
wherein the process is conducted so that
first, some of the hydroxyl groups of the polyol component A) are reacted with the diisocyanate component B) and, after reaching a predetermined NCO content, in a second step the aminosilane is added and reacted with free NCO groups of an OH- and NCO-functional prepolymer obtained in the first step, wherein the aminosilane is added in such an amount that no free NCO groups are detectable in a reaction mixture any longer, and still-free hydroxyl groups of a reaction product are then finally reacted with the isocyanatosilane C),
wherein the catalyst D) comprises:
an organometallic compound of magnesium, zinc, gallium, scandium, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, yttrium or lutetium, an organometallic compound being understood to be a compound which has at least one ligand bonded to the above mentioned metals via an oxygen atom, and the ligands being selected from the group consisting of alkoxy group, sulfonate group, carboxylate group, dialkylphosphate group, dialkylpyrophosphate group and β-diketonate group, where all ligands may be identical or different from each other,
or mixtures of the above mentioned compounds.

2. The process as claimed in claim 1 ,
wherein the catalyst D) comprises:
a beta-diketonate compound of magnesium, zinc, gallium, scandium, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, yttrium or lutetium,
a zinc carboxylate,
or mixtures of the above mentioned compounds.

3. A process for preparing a mixed silane-terminated polymer by reacting a polyol component A) with a diisocyanate component B) comprising isophorone diisocyanate, with at least one isocyanatosilane C) and with an aminosilane E), in which the urethanization reaction is carried out in the presence of at least one catalyst D) which is free of organically bonded tin,
wherein the process is conducted so that
i) the hydroxyl groups of the polyol component A) are reacted simultaneously with the diisocyanate component B) and at least one isocyanatosilane C) in the presence of a catalyst D) and in a second reaction step, free NCO groups of a reaction product are then reacted with an aminosilane E),
or
ii) the isocyanatosilane C) is reacted with some of the hydroxyl groups of the polyol component A) and in a second step still-free hydroxyl groups of the polymer are then reacted with the diisocyanate component B) and then, an aminosilane E) is added and reacted with free NCO groups of the prepolymer obtained, wherein the aminosilane is added in such an amount that no free NCO groups are detectable in a reaction mixture any longer,
wherein the catalyst D) consists of:
an organometallic compound consisting of gallium, scandium, lanthanum, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, yttrium or lutetium, an organometallic compound being understood to be a compound which has at least one ligand bonded to the above mentioned metals via an oxygen atom, and the ligands being selected from the group consisting of alkoxy group, sulfonate group, carboxylate group, dialkylphosphate group, dialkylpyrophosphate group and β-diketonate group, where all ligands may be identical or different from each other,
or mixtures of the above mentioned compounds,

wherein the sole use of ytterbium(III) acetylacetonate as catalyst D) is excluded.

4. The process as claimed in claim 3 , wherein the catalyst D) consists of:
a beta-diketonate compound of magnesium, zinc, gallium, scandium, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, yttrium or lutetium,
a zinc carboxylate,
or mixtures of the above mentioned compounds,

wherein the sole use of ytterbium(III) acetylacetonate as catalyst D) is excluded.

5. The process as claimed in claim 3 , wherein the polyol component A) is a polyether polyol having a number-average molecular weight in a range from 3000 to 24 000 g/mol.

6. The process as claimed in claim 3 , wherein the polyol component A) is a polyether polyol based on polypropylene oxide.

7. The process as claimed in claim 3 , wherein the isocyanate component B) contains exclusively isophorone diisocyanate.

8. The process as claimed in claim 3 , wherein the isocyanatosilane C) is a compound of the formula (II)

in which
R 1 , R 2 and R 3 independently of one another are identical or different saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic or optionally substituted aromatic or araliphatic radicals which have up to 18 carbon atoms and may optionally contain up to 3 heteroatoms from the group of oxygen, sulfur, nitrogen, and
X is a linear or branched organic radical having up to 6 carbon atoms.

9. The process as claimed in claim 3 , wherein the isocyanatosilane C) used is 3-isocyanatopropyltrimethoxysilane.

10. The process as claimed in claim 3 , wherein the aminosilane E) is a compound of the formula (VIII)

in which R 1 , R 2 , and R 3 independently of one another are identical or different saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic or optionally substituted aromatic or araliphatic radicals which have up to 18 carbon atoms and may optionally contain up to 3 heteroatoms from the group of oxygen, sulfur, nitrogen, and
X is a linear or branched organic radical having up to 6 carbon atoms
and
R 10 is hydrogen, a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic or an optionally substituted aromatic or araliphatic radical having up to 18 carbon atoms or a radical of the formula

in which R 1 , R 2 , R 3 and X have the definition given above.

11. The process as claimed in claim 3 , wherein the aminosilane E) is a compound of the formula (IX)

in which
R 1 , R 2 and R 3 independently of one another are identical or different saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic or optionally substituted aromatic or araliphatic radicals which have up to 18 carbon atoms and may optionally contain up to 3 heteroatoms from the group of oxygen, sulfur, nitrogen, and
X is a linear or branched organic radical having at least 2 carbon atoms and
R 11 and R 12 independently of one another are saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic or aromatic organic radicals which have 1 to 18 carbon atoms, are substituted or unsubstituted and/or have heteroatoms in the chain.

12. The process as claimed in claim 3 , wherein the amount of aminosilane E) is chosen such that the

Assignees

• Covestro Intellectual Property Gmbh & Co Kg

Inventors

• Stempfle Florian
• Laas Hans-Josef
• Thiebes Christoph

Classifications

• C08G18/718 Primary

  containing silicon · CPC title

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• C08G18/222 Primary

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

• C08G18/289

  containing silicon · CPC title

• C08G18/4845

  containing oxypropylene or higher oxyalkylene end groups · CPC title