Dithiocarbonate containing polyols as polymer polyol stabilizers

Patent metadata

Field	Value
Publication number	US-10526484-B2
Application number	US-201715848318-A
Country	US
Kind code	B2
Filing date	Dec 20, 2017
Priority date	Dec 20, 2017
Publication date	Jan 7, 2020
Grant date	Jan 7, 2020

Abstract

This invention relates to novel macromers containing dithiocarbonate (or xanthate) groups, novel preformed stabilizers comprising macromers, and novel polymer polyols comprising the novel macromers and/or novel preformed stabilizers. This invention also relates to processes for the preparation of these materials. Other aspects of this invention include foams comprising the novel polymer polyols and a process for preparing foam comprising the novel polymer polyols.

First claim

What is claimed is:

1. A macromer comprising the reaction product of:
(a) a polyether dithiocarbonate polyol having an equivalent weight of 230 Da to 5600 Da, and functionality of 1 to 8, having a dithiocarbonate content of from 0.05% to 20% by weight, and which comprises the copolymerization product of a reaction mixture comprising
(i) one or more starter polyether polyols having an equivalent weight less than 1000 Da, an OH number greater than 56 mg KOH/g polyol, and functionality of 1 to 8,
(ii) an alkylene oxide,
and
(iii) carbon disulfide,
in the presence of
(iv) an alkoxylation catalyst;

with
(b) an ethylenically unsaturated compound containing hydroxyl reactive groups;
optionally, in the presence of
(c) at least one catalyst.

2. The macromer according to claim 1 , wherein (a) said polyether dithiocarbonate polyol has an equivalent weight of 280 Da to 5400 Da, a functionality of 2 to 7, a dithiocarbonate content of 0.10 to 15% by weight, and comprises the reaction product of (i) one or more starter polyether polyols having an OH number of at least 112 mg KOH/g polyol to 1850 mg KOH/g polyol, and a functionality of 2 to 7; (ii) said alkylene oxide comprises ethylene oxide and/or propylene oxide; and (iv) said alkoxylation catalyst comprises a double metal cyanide complex catalyst.

3. The macromer according to claim 1 , wherein (b) said ethylenically unsaturated compound containing hydroxyl reactive groups comprises methyl methacrylate, ethyl methacrylate, maleic anhydride, 3-isopropenyl-α,α-dimethyl benzyl isocyanate, 2-isocyanatoethyl methacrylate, adducts of isophorone diisocyanate and 2-hydroxyethyl methacrylate, adducts of toluene diisocyanate and 2-hydroxylpropyl acrylate, or mixtures thereof.

4. The macromer according to claim 1 , wherein said catalyst (c) comprises an organotin catalyst or a bismuth catalyst.

5. A process for the preparation of a macromer comprising:
(1) reacting:
(a) a polyether dithiocarbonate polyol having an equivalent weight of 230 Da to 5600 Da, and functionality of 1 to 8, having a dithiocarbonate content of from 0.05% to 20% by weight, and which comprises the copolymerization product of a reaction mixture comprising
(i) one or more starter polyether polyols having an equivalent weight less than 1000 Da, an OH number greater than 56 mg KOH/g polyol, and functionality of 1 to 8,
(ii) an alkylene oxide,
and
(iii) carbon disulfide,
in the presence of
(iv) an alkoxylation catalyst;

with
(b) an ethylenically unsaturated compound containing hydroxyl reactive groups;
optionally, in the presence of:
(c) at least one catalyst.

6. The process according to claim 5 , wherein (a) said polyether dithiocarbonate polyol has an equivalent weight of 280 Da to 5400 Da, a functionality of 2 to 7, a dithiocarbonate content of 0.10 to 15% by weight, and comprises the reaction product of (i) one or more starter polyether polyols having an OH number of at least 112 mg KOH/g polyol to 1850 mg KOH/g polyol, and a functionality of 2 to 7; (ii) said alkylene oxide comprises ethylene oxide and/or propylene oxide; and (iv) said alkoxylation catalyst comprises a double metal cyanide complex catalyst.

7. The process according to claim 5 , wherein (b) said ethylenically unsaturated compound containing hydroxyl reactive groups comprises methyl methacrylate, ethyl methacrylate, maleic anhydride, 3-isopropenyl-α,α-dimethyl benzyl isocyanate, 2-isocyanatoethyl methacrylate, adducts of isophorone diisocyanate and 2-hydroxyethyl methacrylate, adducts of toluene diisocyanate and 2-hydroxylpropyl acrylate, or mixtures thereof.

8. The process according to claim 5 , wherein said catalyst (c) comprises an organotin catalyst or a bismuth catalyst.

Assignees

• Covestro Llc
• Covestro Deutschland Ag

Inventors

• Adkins Rick L
• Reese Jack R
• Müller Thomas Ernst
• Gürtler Christoph
• Rauwald Urs
• Subhani Muhammad Afzal
• Jakoby Verena
• Köhler Burkhard
• Leitner Walter

Classifications

• C08G18/6688

  with compounds of group C08G18/3271 · CPC title

• C08G18/4676

  containing sulfur · CPC title

• C08G18/5072

  containing sulfur · CPC title

• C08G18/4837 Primary

  and other oxyalkylene units · CPC title

• C08G18/3275

  containing two hydroxy groups · CPC title