Process for the preparation of silylated polymers having low color and color stability

Patent metadata

Field	Value
Publication number	US-10138324-B2
Application number	US-201514823580-A
Country	US
Kind code	B2
Filing date	Aug 11, 2015
Priority date	Aug 11, 2015
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

A batch or continuous process for preparing silylated polymers having low color and color stability comprising silylating a prepolymer having reactive functional groups with a silylating agent and optionally quenching the silylated polymer, where a stabilizer package containing at least one phosphite stabilizing agent is used.

First claim

The invention claimed is:

1. A process for the preparation of a quenched silylated polymer composition comprising
(a) reacting a prepolymer with a silylating agent, by a silylation reaction, to produce a silylated polymer composition containing reactive isocyanate functional groups in which a stabilization package containing at least one phosphite stabilizer and at least one sterically hindered phenol is added to the process before the silylation reaction or during the silylation reaction; and
(b) quenching the silylated polymer composition of step (a) by reacting a stoichiometric amount or an excess amount of at least one isocyanato-reactive scavenging agent possessing at least one active hydrogen relative with the residual isocyanate of said silylated polymer composition to produce a quenched silylated polymer composition, with the proviso that when the process is a continuous process, the process does not include backmixing of at least a portion of the silylated polymer composition.

2. The process of claim 1 , wherein the prepolymer is a polyol having reactive functional groups or chain extended prepolymer with terminal reactive functional groups, and wherein at least one of the reactive functional groups is hydroxyl or isocyanate.

3. The process of claim 2 wherein the reactive functional groups of either or both of the polyol and the chain extended polymer are terminal reactive functional groups.

4. The process of claim 2 , wherein the chain extended prepolymer is prepared by reacting a polyol with a chain extension agent.

5. The process of claim 4 , wherein the chain extension agent is a diisocyanate or a polyisocyanate.

6. The process of claim 5 , wherein the polyisocyanate is selected from the group consisting of diphenylmethane diisocyanate (MDI), polymeric diphenylmethane diisocyanate (pMDI), paraphenylene diisocyanate, naphthalene diisocyanate, liquid carbodiimide-modified MDI and derivatives thereof, isophorone diisocyanate (IPDI), dicyclohexylmethane-4,4′-diisocyanate, toluene diisocyanate (TDI).

7. The process of claim 1 , wherein the silylating agent is an isocyanatosilane, mercaptosilane, hydroxyl-functional silane or an aminosilane.

8. The process of claim 1 , wherein the silylated polymer composition comprises a fully silylated polymer and a partially silylated polymer.

9. The process of claim 8 , wherein the silylated polymer is a moisture-curable silyiated polyurethane polymer.

10. The process of claim 1 , wherein the at least one isocyanato-reactive scavenging agent possessing at least one active hydrogen is cyclic amide scavenging agent.

11. The process of claim 10 , wherein the at least one cyclic amide scavenging agent is blended with vinyltrimethoxysilane to form a scavenging package.

12. The process of claim 11 , wherein the cyclic amide is selected from the group consisting of ε-caprolactam, 2-pyrrolidone and combinations thereof.

13. The process of claim 3 , wherein when one of the terminal reactive functional groups is isocyanate, the silylating agent is an aminosilane or when one of the terminal reactive functional groups is a hydroxyl group, the silylating agent is an isocyanatosilane.

14. The process of claim 1 , wherein the silylating agent is isocyanatopropyltrimethoxysilane.

15. The process of claim 4 , wherein the stabilizing package is added to polyol before the silylation step and before a chain extension of the polyol.

16. The process of claim 1 , wherein the stabilizing package comprises a hindered phenol having the general Formula (5):

wherein each occurrence of R 18 is a monovalent or polyvalent organic radical of from 1 to about 50 carbon atoms and optionally containing substituents selected from group consisting of hydroxyl group, —OH; amide group, —C(═O)N(—) 2 ; ester group, —C(═O)O—; isocyanurate group

ether group, —O—; amine group, (—) 2 NH; hydrazide, —C(═O)N(—)NH(—) 2 —; sulfide group, —S—; and combinations thereof; or
the general Formula (6):

wherein R 19 is a divalent, trivalent or tetravalent organic group of from 1 to about 50 carbon atoms and optionally containing substituents selected from group consisting of a hydroxyl group, —OH; amide group, —C(═O)N(—) 2 ; ester group —C(═O)O—; isocyanurate group

ether group, —O—; amine group, (—) 2 NH; hydrazide, —C(═O)N(—) NH(—) 2 —; sulfide group, —S—; and combination thereof; and the subscript i is an integer of from about 2 to about 4.

17. The process of claim 1 , wherein the phosphite stabilizer is of the formula (7)

wherein
each occurrence of R 20 is independently selected from the group consisting of a monovalent hydrocarbon containing from 1 to 25 carbon atoms, a monovalent hydrocarbon containing from 1 to 25 carbon atoms and at least one heteroatom selected from the group consisting of oxygen atom, nitrogen atoms and sulfur atom, and a polyvalent hydrocarbon containing from 1 to 25 carbon atoms in which at least one carbon atom is bonded to the oxygen of the oxygen-phosphorus group and at least one carbon atom is covalently bonded to a carbon atom of the R 21 group; each occurrence of R 21 is independently selected from the group consisting of a monovalent hydrocarbon containing from 1 to 25 carbon atoms, a monovalent hydrocarbon containing from 1 to 25 carbon atoms and at least one heteroatom selected from the group consisting of oxygen atom, nitrogen atoms and sulfur atom, and a polyvalent hydrocarbon containing from 1 to 25 carbon atoms in which at least one carbon atom is bonded to the oxygen of the oxygen-phosphorus group and at least one carbon atom is covalently bonded to a carbon atom of the R 20 group; and
each occurrence of R 22 is independently a monovalent hydrocarbon containing 1 to 25 carbon atoms and optionally containing at least one heteroatom selected from the group consisting of oxygen atom, nitrogen atoms and sulfur atom.

18. The process of claim 1 , wherein the phosphite stabilizer is selected from the group consisting of triisodecyl phosphite; triphenyl phosphite; tris(2,4-di-tert-butylphenyl)phosphite; 2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxy-N,N-bis[2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxyethyl]ethanamine; bis(2,4-di-tert-butyl-6-methylphenyl)-ethyl-phosphite; 3,9-bis-(2,4-di-tert-butyl-phenoxy)-2,4,8,10-tetraoxa-3,9-diphospha-spiro[5.5]undecane; tris (nonylphenyl) phosphite; phenyl diisodecyl phosphite; diphenyl isooctyl phosphite; triisotridecyl phosphite; 2-ethylhexyl diphenyl phosphite; trilauryl phosphite; diphenyl tridecyl phosphite; and mixtures thereof.

19. The process of claim 5 , wherein the polyisocyanate is selected from the group consisting of hexamethylene diisocyanate, phenylene diisocyanate, toluene diisocyanate, 4,4′-diphenylmethane diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, cyclohexane diisocyanate and 1,3-bis-(isocyanatomethyl)cyclohexane.

20. The process of claim 1 , wherein the isocyanate-reactive scavenging agent possessing at least on

Assignees

• Momentive Performance Mat Inc

Inventors

• Banevicius John
• Huang Misty
• O'Keefe Brendan
• Kumar Vikram
• Barbera Bruce

Classifications

• C08G18/837 Primary

  by silicon containing compounds · CPC title

• C08G18/0895

  Manufacture of polymers by continuous processes (C08G18/0838 takes precedence) · CPC title

• C08G18/8074

  Lactams · CPC title

• C08G18/718

  containing silicon · CPC title

• C08G18/289

  containing silicon · CPC title