Functionalized accelerating resins derived from renewable materials

Patent metadata

Field	Value
Publication number	US-11401367-B2
Application number	US-201816002488-A
Country	US
Kind code	B2
Filing date	Jun 7, 2018
Priority date	Dec 8, 2015
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

The present invention relates to curable polyurethane polymers made from renewable materials and having polymerization accelerator groups built into the polymer. In particular hydroxylated oleaginous materials derived from plant oils, such as soybean oil, are used. These renewable materials may be formed into curable polyurethane polymers having different chemical functionalities and cure mechanisms.

First claim

The invention claimed is:

1. A polymerizable polymer corresponding to the following structure:
MA-U-A-U-MA
wherein A comprises an oleaginous backbone derived from hydroxylated plant oil that is selected from the group consisting of hydroxylated soybean oil, hydroxylated almond oil, hydroxylated canola oil, hydroxylated coconut oil, hydroxylated corn oil, hydroxylated cottonseed oil, hydroxylated flaxseed oil, hydroxylated linseed oil, hydroxylated olive oil, hydroxylated palm oil, hydroxylated peanut oil, hydroxylated safflower oil, hydroxylated sesame oil, hydroxylated sunflower oil, hydroxylated walnut oil, and combinations thereof, U comprises a hydrocarbyl linker that is bound to a group comprising both a urethane linkage and a polymerization accelerator group and further optionally comprising a free isocyanate group or hydroxyl group, and MA comprises an alkoxy-containing group derived from a reactant selected from the group consisting of 3-isocyanatopropyltriethoxysilane, 3-isocyanatopropylmethyldiethoxysilane, 3-isocyanatopropyldimethylethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropylmethyldimethoxysilane, 3-isocyanatopropyldimethylmethoxysilane, 4-aminobutyltriethoxysilane, 4-aminobutylmethyldiethoxysilane, 4-aminobutyldimethylethoxysilane, 4-aminobutyltrimethoxysilane, 4-aminobutylmethyldimethoxysilane, 4-aminobutyldimethylmethoxysilane, 4-amino-3,3-dimethylbutylmethyldimethoxysilane, dimethylbutyltrimethoxysilane, 1-amino-2-(dimethylethoxysilyl)propane, 3-(m-aminophenoxy)propyltrimethoxysilane, m-aminophenyltrimethoxysilane, m-aminophenyltriethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-aminopropyldimethyethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropyldimethymethoxysilane, 3-aminopropylmethylbis(trimethylsiloxy)silane, 3-aminopropylpentamethyldisiloxane, 11-aminoundecyltriethoxysilane, and 11-aminoundecyltrimethoxysilane, wherein the polymerizable polymer comprises about 45% to about 60% by weight of renewable content.

2. The polymerizable polymer of claim 1 , wherein the hydroxylated plant oil has a hydroxyl functionality from about 1.0 to about 7.0.

3. The polymer of claim 1 , wherein U is derived from a diisocyanate reactant selected from the group consisting of isophorone diisocyanate (IPDI), IPDI isocyanurate, polymeric IPDI, naphthalene 1,5-diisocyanate (NDI), methylene bis-cyclohexylisocyanate, methylene diphenyl diisocyanate (MDI), polymeric MDI, toluene diisocyanate (TDI), isocyanurate of TDI, TDI-trimethylolpropane adduct, polymeric TDI, hexamethylene diisocyanate (HDI), HDI isocyanurate, HDI biurate, polymeric HDI, xylylene diisocyanate, hydrogenated xylylene diisocyanate, tetramethyl xylylene diisocyanate, p-phenylene diisocyanate, 3,3′-dimethyldiphenyl-4,4′-diisocyanate (DDDI), 2,2,4-trimethylhexamethylene diisocyanate (TMDI), norbornane diisocyanate (NDI) and 4,4′-dibenzyl diisocyanate (DBDI).

4. The polymer of claim 1 , wherein the polymerization accelerator group bound to the hydrocarbyl linker of U is derived from a reactant which is an aliphatic or aromatic diol compound having an active nitrogen, which diol compound may be optionally substituted.

5. The polymer of claim 1 , wherein the polymerization accelerator group bound to the hydrocarbyl linker of U is derived from a reactant which has the structure:

wherein R 2 is a hydrocarbyl group C 1-20 which may be optionally substituted and may contain heteroatoms S or N; and n and m are each 1-13.

6. The polymer of claim 4 , wherein the polymerization accelerator group is a residue of the structure:

7. The polymer of claim 4 , wherein the polymerization accelerator group is a residue of one of the structures:

8. A curable adhesive, sealant or coating composition comprising the polymer of claim 1 and a cure system selected from the group consisting of a free radical initiator system, a moisture cure system and combinations thereof.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Messana Andrew D
• Dworak David P
• Jacobine Anthony F
• Gustafson Darel

Classifications

• C08G18/6651 Primary

  with compounds of group C08G18/3225 or polyamines of C08G18/38 · CPC title

• C08G18/8051

  with compounds of C08G18/36 · CPC title

• C08G18/3844

  containing one nitrogen atom in the ring · CPC title

• C08G18/4238

  derived from dicarboxylic acids and dialcohols · CPC title

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title