Isocyanatoalkyl alkoxysilane adducts modified by silicone resins and the use thereof

Patent metadata

Field	Value
Publication number	US-10633555-B2
Application number	US-201615763622-A
Country	US
Kind code	B2
Filing date	Sep 29, 2016
Priority date	Sep 30, 2015
Publication date	Apr 28, 2020
Grant date	Apr 28, 2020

Abstract

A binder that can be used in a paint composition, an adhesive composition, and/or a sealant composition. The binder includes a reaction product formed from an adduct (A) of an isocyanatoalkylalkoxysilane (A1) and an alcohol (A2) with an alkoxysilane-containing Q unit-free alkyl- and/or arylsilicone resin (B).

First claim

The invention claimed is:

1. A binder, comprising:
a reaction product formed from an adduct (A) of an isocyanatoalkylalkoxysilane (A1) and an alcohol (A2) with an alkoxysilane-containing Q unit-free alkyl- and/or arylsilicone resin (B)
comprising units of formula (I)
R 3 c (R 4 O) d R 5 e SiO (4-c-d-c)/2   formula (I)

wherein
R 3 may be the same or different and is a hydrogen atom, a monovalent, SiC-bonded, optionally halogen substituted aliphatic hydrocarbyl radical or a divalent, optionally halogen substituted, aliphatic hydrocarbyl radical that forms a bridge between two units of the formula (I),
R 4 may be the same or different and is a hydrogen atom or a monovalent, optionally halogen substituted hydrocarbyl radical,
R 5 may be the same or different and is a monovalent, SiC-bonded, optionally halogen substituted aromatic hydrocarbyl radical,
c is 0, 1, 2 or 3,
d is 0, 1, 2 or 3, and
e is 0, 1 or 2,
with the proviso that the sum total of c+d+e is greater than 0 and less than or equal to 3 and, in addition, c+e≥1
wherein said silicone resin has at least 20% of units of formula (I) in which c is 0 and/or not more than 20% of units of formula (I) in which c is 2.

2. The binder according to claim 1 , wherein
the isocyanatoalkylalkoxysilane (A1) is at least one member selected from the group consisting of isocyanatomethyltrimethoxysilane, isocyanatomethyltriethoxysilane, isocyanatomethyltriisopropoxysilane, 2-isocyanatoethyltrimethoxysilane, 2-isocyanatoethyltriethoxysilane, 2-isocyanatoethyltriisopropoxysilane, 3-isocyanato-n-propyltrimethoxysilane, 3-isocyanato-n-propyltriethoxysilane, 3-isocyanato-n-propyltriisopropoxysilane, 4-isocyanato-n-butyltrimethoxysilane, 4-isocyanato-n-butyltriethoxysilane, and 4-isocyanato-n-butyltriisopropoxysilane.

3. The binder according to claim 1 , wherein
the alcohol (A2) is a mono- or polyhydric alcohol.

4. The binder according to claim 3 , wherein
the polyhydric alcohol is at least one member selected from the group consisting of ethylene glycol, propane-1,2-diol, propane-1,3-diol, butane-1,4-diol, pentane-1,5-diol, hexane-1,6-diol, decane-1,10-diol, dodecane-1,12-diol, glycerol, isosorbitol, isomannitol, isoiditol, 2,2,4-trimethylhexane-1,6-diol and 2,4,4-trimethylhexane-1,6-diol, alone or as any desired mixtures of these isomers, 2,2-dimethylbutane-1,3-diol, 2-methylpentane-2,4-diol, 3-methylpentane-2,4-diol, 2,2,4-trimethyl-1-pentane-1,3-diol, 2-ethylhexane-1,3-diol, 2,2-dimethylhexane-1,3-diol, 3-methylpentane-1,5-diol, 2-methylpentane-1,5-diol, 2,2-dimethylpropane-1,3-diol (neopentyl glycol), neopentyl glycol hydroxypivalate, polyethylene glycol, polypropylene glycol, sorbitol, pentaerythritol, 1,1,1-trimethylolpropane, 3(4),8(9)-bis(hydroxymethyl)tricyclo[5.2.1.02,6]decane (dicidol), and 2,2-bis(4-hydroxycyclohexyl)propane.

5. The binder according to claim 1 , wherein
the molar ratio of OH groups in the alcohols (A2) to NCO groups in the isocyanatoalkyltrialkoxysilane (A1) is 0.8:1 to 1.2:1.

6. A process for preparing the binder according to claim 1 , the process comprising:
reacting an adduct (A) formed from an isocyanatoalkylalkoxysilane (A1) and an alcohol (A2) with an alkoxysilane-containing alkyl- and/or arylsilicone resin (B), optionally in the presence of a catalyst (C), an alcohol (D), and/or water.

7. The process according to claim 6 , wherein said reacting is conducted at temperatures in the range of 30-150° C.

8. The process according to claim 6 , wherein
the catalysts (C) is present and is at least one member selected from the group consisting of
a carboxylic acid having a melting point of >60° C., a tetraalkylammonium carboxylate, a metal complex with a chelate ligand, an organic Sn(IV) compound, an organic Sn(II) compound, an organic Zn compound, an organic Bi compound, a tertiary amine, a phosphorus-containing catalyst, a phosphorus- and nitrogen-containing catalyst, an organic sulphonic acid in unblocked form, an organic sulphonic acid in blocked form, and a mixture thereof.

9. The process according to claim 6 , wherein
adduct (A) and the alkoxysilane-containing alkyl- and/or arylsilicone resin (B) are present in the same weight ratio.

10. A coating composition, comprising:
I) at least one binder according to claim 1 ,
II) optionally one or more additional binder components,
III) optionally a catalyst,
IV) optionally an auxiliary and an additive,
V) optionally an organic solvent, and
VI) optionally an aminosilane.

11. The coating composition according to claim 10 , wherein
said catalyst (III) is present and is at least one member selected from the group consisting of a Lewis acid, a metal or transition metal chelate, a metal or transition metal salt, a metal or transition metal particle, a sulphonic acid in free form, a sulphonic acid in neutralized form, a sulphonic acid in adduct form, phosphoric acid, a phosphorous acid, a derivative of a phosphoric acid, a derivative of a phosphorous acid, a high-boiling acid, a quaternary ammonium carboxylate, and a mixture thereof.

12. A paint, an adhesive, or a sealant, which comprises the binder according to claim 1 .

13. A process of making a paint, an adhesive, or a sealant, the process comprising:
adding a binder according to claim 1 to a paint composition, an adhesive composition, or a sealant composition.

14. A process of making a coated article, the processing comprising:
coating an article with the coating composition according to claim 10 , thereby obtaining the coated article.

15. The binder according to claim 1 , wherein said silicone resin (B) has a viscosity range of 10-100,000 mPas.

16. The binder according to claim 1 , wherein said silicon resin (B) has a ratio of (T) to (D) units of 0.5 to 2.0.

Assignees

• Evonik Operations Gmbh

Inventors

• Stache Wiebke
• Hallack Markus
• Lilienthal Annegret
• Ballauf Sina
• Bauer Tina
• Klawikowski Ralf
• Klotzbach Thomas

Classifications

• C08L83/14

  in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08L83/10 takes precedence) · CPC title

• C08G77/388

  containing nitrogen · CPC title

• C08G18/61

  Polysiloxanes · CPC title

• C08L83/06

  containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence) · CPC title

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title