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

Patent metadata

Field	Value
Publication number	US-10556983-B2
Application number	US-201816163039-A
Country	US
Kind code	B2
Filing date	Oct 17, 2018
Priority date	Aug 11, 2015
Publication date	Feb 11, 2020
Grant date	Feb 11, 2020

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 quenched silylated polymer having the general Formula (11):

each occurrence of A 1 is a functional group selected from the group consisting of —O—, —S— and —NH—;
each occurrence of A 2 is a functional group selected from the group consisting of —S—, —NR 6 , where R 6 is selected from the group consisting of hydrogen, an alkyl group containing from 1 to about 10 carbon atoms, cycloalkyl group containing from about 5 to about 10 carbon atoms, an aralkyl group containing from about 7 to about 10 carbon atoms, phenyl and —CH[(C═O)OR 7 ]CHR 8 C(═O)OR 7 , where R 7 is an alkyl group of from 1 to about 10 carbon atoms, a cycloalkyl group of from about 5 to about 10 carbon atoms, an aryl group of from about 6 to about 10 carbon atoms, and aralkyl group of from about 7 to about 10 carbon atoms and R 8 is an alkyl group of from 1 to about 10 carbon atoms, a cycloalkyl group of from about 5 to about 10 carbon atoms, an aryl group of from about 6 to about 10 carbon atoms, and aralkyl group of from about 7 to about 10 carbon atoms;
R 1 is an organic group containing from about 50 to about 4,000 carbon atoms and at least one functional group selected from group consisting of —O—, —S—, —OC(═O)NH—, —R 2 NC(═O)NH—, —C(═O)O—, —OC(═O)O—, —OCHR 2 O—, —C(═O)NR 2 — and —NR 2 —, wherein each occurrence of R 2 is independently hydrogen, an alkyl group containing from 1 to about 6 carbon atoms or phenyl, preferably hydrogen;
R 4 is a divalent alkylene group containing from 1 to about 10 carbon atoms, a cycloalkylene group containing from about 5 to about 10 carbon atoms and an arylene group containing from about 6 to about 10 carbon atoms;
each occurrence of R 5 is an alkyl group of from 1 to about 18 carbon atoms or a —R 9 (OR 10 ) c OR 11 , where R 9 is an alkyl group of from 1 to about 18 carbon atoms, R 10 is a divalent alkylene group of from about 2 to about 4 carbon atoms, and R 11 is an alkyl group of from 1 to about 10 carbon atoms or —C(═O)R 12 , where R 12 is hydrogen, or an alkyl group of from 1 to about 6 carbon atoms, and
the subscripts a, b, c and h are integers where a is 2 to about 5, b is 0 to about 2, c is 0 to about 5, and h is 1 to 6, with the proviso that when A 1 is —O— or —S—, then A 2 is —NH—.

2. The quenched silylated polymer of claim 1 , wherein R 1 is derived from poly(oxyethylene) diols, the poly(oxypropylene) diols, poly(oxyethylene-oxypropylene)diols, polyoxyalkylene triols, polytetramethylene glycols, polyacetals, polyhydroxy polyacrylates, polyhydroxy polyester amides, polyhydroxy polythioethers, polycaprolactone diols or polycaprolactone triols.

3. The quenched silylated polymer of claim 1 , wherein R 1 is derived from a poly(alkylene oxide) diol.

4. The quenched silylated polymer of claim 2 , wherein poly(oxypropylene)diol has a number average molecular weight of from 4,000 to 20,000 grams/mole.

5. The quenched silylated polymer of claim 1 , wherein R 1 is derived from a diisocyanate extended poly(propylene oxide) diol.

6. The quenched silylated polymer of claim 1 , wherein R 4 is —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH(CH 3 )CH 2 —.

7. The quenched silylated polymer of claim 1 , wherein R 5 is —CH 3 or —CH 2 CH 3 .

8. The quenched silylated polymer of claim 1 , wherein A 1 is —O— or —NH—.

9. The quenched silylated polymer of claim 1 , wherein A 2 is —NH— or —NCH 3 —.

10. The quenched silylated polymer of claim 1 , where a is 2.

11. The quenched silylated polymer of claim 1 , where h is 1 or 2.

12. The quenched silylated polymer of claim 4 , wherein R 4 is —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH(CH 3 )CH 2 —; R 5 is —CH 3 or —CH 2 CH 3 ; A 1 is —O— or —NH—I—; A 2 is —NH— or —NCH 3 —; and a is 2.

13. The quenched silylated polymer of claim 5 , wherein R 4 is —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH(CH 3 )CH 2 —; R 5 is —CH 3 or —CH 2 CH 3 ; A 1 is —O— or —NH—; A 2 is —NH— or —NCH 3 —; and a is 2.

14. A silylated polymer composition comprising:
(i) a quenched silylated polymer having silylated polymer having the general Formula (11):

each occurrence of A 1 is a functional group selected from the group consisting of —O—, —S— and —NH—;
each occurrence of A 2 is a functional group selected from the group consisting of —S—, —NR 6 , where R 6 is selected from the group consisting of hydrogen, an alkyl group containing from 1 to about 10 carbon atoms, cycloalkyl group containing from about 5 to about 10 carbon atoms, an aralkyl group containing from about 7 to about 10 carbon atoms, phenyl and —CH[(C═O)OR 7 ]CHR 8 C(═O)OR 7 , where R 7 is an alkyl group of from 1 to about 10 carbon atoms, a cycloalkyl group of from about 5 to about 10 carbon atoms, an aryl group of from about 6 to about 10 carbon atoms, and aralkyl group of from about 7 to about 10 carbon atoms and R 8 is an alkyl group of from 1 to about 10 carbon atoms, a cycloalkyl group of from about 5 to about 10 carbon atoms, an aryl group of from about 6 to about 10 carbon atoms, and aralkyl group of from about 7 to about 10 carbon atoms;
R 1 is an organic group containing from about 50 to about 4,000 carbon atoms and at least one functional group selected from group consisting of —O—, —S—, —OC(═O)NH—, —R 2 NC(═O)NH—, —C(═O)O—, —OC(═O)O—, —OCHR 2 O—, —C(═O)NR 2 — and —NR 2 —, wherein each occurrence of R 2 is independently hydrogen, an alkyl group containing from 1 to about 6 carbon atoms or phenyl, preferably hydrogen;
R 4 is a divalent alkylene group containing from 1 to about 10 carbon atoms, a cycloalkylene group containing from about 5 to about 10 carbon atoms and an arylene group containing from about 6 to about 10 carbon atoms;
each occurrence of R 5 is an alkyl group of from 1 to about 18 carbon atoms or a —R 9 (OR 10 ) c OR 11 , where R 9 is an alkyl group of from 1 to about 18 carbon atoms, R 10 is a divalent alkylene group of from about 2 to about 4 carbon atoms, and R 11 is an alkyl group of from 1 to about 10 carbon atoms or —C(═O)R 12 , where R 12 is hydrogen, or an alkyl group of from 1 to about 6 carbon atoms, and
the subscripts a, b, c and h are integers where a is 2 to about 5, b is 0 to about 2, c is 0 to about 5, and h is 1 to 6, with the proviso that when A 1 is —O— or —S—, then A 2 is —NH—; and

(ii) a stabilizing package comprising a phosphite stabilizer.

15. The silylated polymer composition of claim 14 , wherein the phosphite stabilizer has the general Formula (7):

wherein
each occurrence of R 20 is independently selected from the group consisting of a monovalent hydrocarbon containing from 1 to about 25 carbon atoms, a monovalent hydrocarbon containing from 1 to about 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 about 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 about 25 carbon a

Assignees

• Momentive Performance Mat Inc

Inventors

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

Classifications

• C08G18/8074

  Lactams · CPC title

• C08G18/289

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• C08K5/1345

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• C08G18/718

  containing silicon · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title