CA2032978A1 - Copolymers from polyalkylene oxides containing an allyl glycidyl ether reactive double bond and vinyl acetate - Google Patents

Copolymers from polyalkylene oxides containing an allyl glycidyl ether reactive double bond and vinyl acetate

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Publication number
CA2032978A1
CA2032978A1 CA002032978A CA2032978A CA2032978A1 CA 2032978 A1 CA2032978 A1 CA 2032978A1 CA 002032978 A CA002032978 A CA 002032978A CA 2032978 A CA2032978 A CA 2032978A CA 2032978 A1 CA2032978 A1 CA 2032978A1
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CA
Canada
Prior art keywords
copolymer
set forth
composition
polyol
matter
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002032978A
Other languages
French (fr)
Inventor
Pauls Davis
Steven D. Gagnon
Eric Lind
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Corp
Original Assignee
Pauls Davis
Steven D. Gagnon
Eric Lind
Basf Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pauls Davis, Steven D. Gagnon, Eric Lind, Basf Corporation filed Critical Pauls Davis
Publication of CA2032978A1 publication Critical patent/CA2032978A1/en
Abandoned legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/62Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6212Polymers of alkenylalcohols; Acetals thereof; Oxyalkylation products thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F218/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
    • C08F218/02Esters of monocarboxylic acids
    • C08F218/04Vinyl esters
    • C08F218/08Vinyl acetate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06Polymers provided for in subclass C08G
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/12Hydrolysis
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/44Preparation of metal salts or ammonium salts
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00Chemical modification of a polymer
    • C08F2810/30Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups

Abstract

Abstract of the Disclosure A copolymer based on vinyl acetate and polyalkylene oxide(s) containing an allyl glycidyl ether reactive double bond.

Description

j2,,/i Ex~ress Mall No. NB310294083 DecemDer 22, 1989 COPOLYMERS ~ROM POLYALKYLENE OXIDES CONTAINING AN ALLYL
GLYCIDYL ETHER REACTIVE DOU~LE BOND AND VINYL ACETATE

1. Field of the Invention This invention relates to copolymers ba3ed on vinyl acetate and a polyalkylene oxide containing ~n allyl glycidyl ether reactive double bond.
BACRGROUND OF THE INVENTION
Vinyl acetate iR a relatively inexpensive material from which polymer6 may be produced. ~eretofor, polymerization of vinyl acetate produced molecules of relatively high vi~cosity, and having low hydroxyl functionality. Such characteristics of polyvinyl acetate make it undesirable aB a polyol, and more particularly unde~irable for use in the production of ureth~nes.
Purther, vinyl acetate iB a monomer with relatively low reactivity and thu~ the polymerization of ~uch a monomer requires a great deal of heat or exce~s quantities of initiator.
Thu~ ~ polymerB of vinyl acetate which have rclatively low vi~co~ity, have acceptable functionality, ~nd r~guire relat~vely low heat or ~cceptable ~mounts of ~nitiator to produce would be advantageous 8 polyols, ~nd ~ore particularly for u~e in the production of urethane~.

- SummarY of the Invention The present invention provides vinyl acetate based copolymers prepared from the free radical copolymerization of vinyl acetate and polyalkylene oxide(s) having allyl glycidyl ether units. Preferably, the vinyl acetate based copolymers have the general formula I:

R ~CH2 fH)x (C~2-CH - )y_R2 f 1 2 c=o f ~I) CH-OH
CH

wherein R i5 a polyalkylene o~ide, Rl ~nd R2 are each end groups, preferably hydroxyl or ~opropoxyl group~, and Y i~
equ~l to or greater than y.
The polyalkylene ox~de h~ving ~n allyl glycidyl ~ther unit h~ve the general formula Il, OIH
R-cH2-cH-cH2-o-cH2-cH=cH2 . ~II) wherein R is a polyalkylene oxide.
The vinyl acetate based copolymers of the present invention have relatively low viscosity, have sufficient functionality for use as a polyol and for use in the production of urethanes, and are 601uble in polyether~.
Detailed DescriPtion of the Invention In one embodiment, the invention provides, a modified polyvinyl acetate rom the free radical copolymerization of vinyl acetate and polyalkylene oxide(s) having an allyl glycidyl ether unit of the general formula II
OH
R-CH2-CH-C~2-O-CH2-C~=CH2 (II) wherein R i3 a polyalkylene oYide; preferably polyethylene oxide, polypropylene oxide, polybutylene oxide or polytetrahydrofuran. The molecular weight of the polyalkylene oxide may vary but is preferably in the range of about 200 to about 2000 grams per mole. The copolymer has a number average molecular weight (GPC MWn) ranging from about 500 to about 5000, and more preferably, from about 500 to about 2000. The copolymer~ have a vi~c06ity rangi~g from about 5000 to about 100,000 cP, and preferably from ~bout 40,000 to ~bout 100,000 cP ~ 25C. The polyalkylene oxide may be synthesized with a variety of initiators which are discus6ed in greater detail hereafter.
~ he polyalkylene oxide having an alkyl glycidyl ether unit i6 polymerized with vinyl acetate to produce a copolymers of the general formula I:
P. ( CH2 fH ) X ( CH2-CEI_ ~ _R2 1 l~2 C=O O
CH3 lH2 CH-O~

wherein R is a polyalkylene oxide as described above, Rl and R2 are end groups, preferably each being selected from the group consicting of hydroxyl and/or isopropoxyl, and wherein x is SO - 99.999 mole percent and y is 0.001 - 50 mole percent; preferably x is 75 - 99.995 mole percent and y is 0.005 - 25 mole percent, and most preferably x is 85 -99.99S mole percent and y is 0.005 - 15 mole percent.
In another embodiment, the vinyl acetate based copolymer, prepared from the free radical copolymerization of vinyl acetate and polyalkylene oxide~s) having an allyl Z03X9~78 glycidyl ether unit, includes a vinyl alcohol group. ~he vinyl alcohol group may be pre~ent in an amount ranging from trace quantitie6 to about five mole percent. Such copolymer~ preferably have the formula;

~ CH2-CH)y~ - (CH2-CH)X -~C~-fH)yR2 lso CH3 C~2 C~-OH

l~2 wherein R i8 a polyalkylene oxide a~ described above, Rl and R2 are end groups, preferably each being ~elected from the group consi~ting of hydroxyl and isopropoxyl, and wherein x ~B 50-99.999 ~ole percent and y ~B 0.001-50 mole percent and x ran~es from trace quantities to about 5 mole percent, preferably Y iB 75-99.999 mole percent and y is 0.005-25 ~ole percent, and mo~t preferably x i~ ~5-99.995 ~ole percent and y iB 0.005-15 ~ole percent.
The polyalkylene oxide in the above for~ula~ are generally prepared by well-known ~ethods, for exa~ple by the ba~e catalyzed additlon of alkylene oxide, preferably ethylene oxide, propylene oxi~e or butylene oxide to ,. , .. , .. ~

initiator molecule containing on an average two or more active hydrogens. Also acid catalyzed polymerization of tetrahydrofuran is ~uitable. Preferably such initiators include methanol and solketal. Examples of other suitable initiator molecules include dihydric initiators such as ethylene glycol, propylene glycol, butylene glycol, neopentyl glycol, 1,6-hexanediol, hydroguinone, resorcinol, the bisphenols, aniline and other aromatic m~noamines, aliphatic monoamines, and monoesters of glycerine; trihydric initiators such as glycerine, trimethylolpropane, trimethylolethane, N-alkylphenylenediamines, mono-, di, and trialkanolamines; tetrahydric initiators such a~ ethylene diamine, propylenediamine, 2,4'-, 2,2'-, and 4,4'-methylenedianiline, toluenediamine, and pentaerythritol;
pentahydric initiators such a3 diethylenetriamine; and hexahydric and octahydric initiators ~uch as sorbitol and ~ucrose.
Addition of alkylene oxide to the initiator ~olecules may take pl~ce simultaneously or seguentially when ~orc than one alkylene oxide i~ used, resulting in block, heteric, ~nd block-heteric polyoxyalkylene polyether~. ~he number of hydroxyl groups will generally equal the number of active hydrogens in the initiator ~olecule. Proce~3es for _ . _ preparing such polyethers are described both in the Polyurethane Handbook and Polyurethanes: Chemistrv and ~echnologY as well as in many patents, for example u.S.
Patents 1,922, 451; 2,6?4,619; 1,922,459; 3,190,927; and 3,346,557.
By way of example, suitable initiators for the random copolymerization include isopropyl alcohol, hydrogen peroxide and solketal.
The copolymers may be blended with hydroxyl-group-containing compounds for use in preparing urethane foams.
~uitable hydroxyl-group-containing compounds include aliphatic glycols, dihydroxy aromatics, bisphenols, hydroYyl terminated polyethers, polyesters and poly2cetals. The copolymer ~ay comprise from about 2 to about 99, pre~erably about 2 to about 20, and most preferably 5 to about 20 weight percent of the blend.
Preferably, the vinyl acetate based copolymer i~
prepared by the free radical procese using a continuous process tubul~r reactor ~y~tem. U.S. Patent No. 3,673,168 d~scloses ~ tubular reactor and continuou~ process for producing polymeric materials which are ~uitable for use in producing the vinyl cetate based copolymer of the pre~ent invention. U.8. Patent No. 3,673,168 i~ hereby incorporated ... .. . .. . . . . . . .. . ... . . . .

;~03Z978 by reference. Vinyl acetate monomer and the polyalkylene oYide containing an allyl glycidyl ether are continuously feed into a tubular reactor in the presence of a solvent and ~n initiator. The vinyl acetate monomer i5 randomly polymerized with the polyalkylene oxide containing allyl glycidyl ether unit to yield the polyol in the tubular reactor. The polyol crude products ~o produced are continuously withdrawn from the tubular reactor mixture.
~ he following examples illustrate the nature of the invention.
In the following examples the materials used, were vinyl acetate (99~ pure), butanol, ethyl alcohol, ethyl acetate from Aldrich Chemical Company; hydrogen peroxide from Dupont Chemical Company under the name Albone 50; and 2-propanol (purity of 99%) from American Scientific Products under the above name.

4Z03Z9~8 Example 1 The reactant3 shown in Table I were charged to a feeder vessel in the polymerization system described above.

able I
Vinyl Acetate (~Ac) 500 9 Polytetrahydrofuran (1000 9/~)/1.25 ~oles Allyl glycidyl ether cap 100 g 50% H2O2 60 9 Isopropyl Alcohol (IPA) 340 9 The reactants were added in no special order tO a 2000 mL
flask then poured into a ~tirred, water cooled feeder vessel. Nitrogen was bubbled through the reaction mixture. The content~ were gravity fed into a diaphragm high pres~ure pump. The diaphragm pumps fed the reaction mixture at 450 psig and at a rate of 300 mL/hour into a heated ~155C) stainless steel co$1. The slightly viscous liquid react~on product was collected st the end of the tubular reactor in a collector vessel. The volatiles were ~tripped off using a ~otary evaporator. The resulting vi~cous oil was di3solved in ethyl acetate and neutralized to pH 8 with aqueous ~odium bicarbonate. The organie layer was extracted, then washed with brine. The organic layer was collected and dried over sodium ~ulfate to give a 30 _g_ .... .... . ... . . . .

~Z032978 percent yield of product, OH~ 56.7, acid ~ O.0, % H2O =
0.04%.

Example II
A random copolymerization was carried out in the same manner described in Example I using tbe amount of reagents as listed in Table II. The reaction gave a 51 percent yield of product, OH# = 64.2, acid # 0.0, ~ H~O =
0.0B%.

Table II
VAc soo g MeOH initiated Polyethylene glycol (1500 g/mJ/
Allyl glycidyl ether 100 9 50~ H2O2 60 9 The vinyl acetate based copolymers prepared in Examples I-II
were ~oluble in polyethers and were suitable for use in preparing polyurethanes.

. . .

Claims (39)

1. A copolymer having the general formula:

wherein R is a polyalkylene oxide, R1 and R2 are end groups, and X is equal to or greater than y.
2. A copolymer as set forth in claim 1 wherein X
is 50-99.999 mole percent and y is 0.001 - 50 mole percent.
3. A copolymer as set forth in claim 1 wherein R
is selected from the group consisting of polyethylene oxide, polypropylene oxide, polybutylene oxide, and polytetrahydrofuran.
4. A copolymer as set forth in claim 1 wherein R1 and R2 are each OH.
5. A copolymer as set forth in claim 1 wherein R1 and R2 are each an isopropoxyl groups.
6. A copolymer as set forth in claim 1 wherein R1 is OH and R2 is an isopropoxyl group.
7. A copolymer as set forth in claim 1 wherein and R2 are each selected from the group consisting of hydroxyl and isopropoxyl.
8. A copolymer as set forth in claim 1 wherein X
is 75 - 99.995 mole percent and y is 0.005 - 25 mole percent.
9. A copolymer as set forth in claim 1 wherein x is 85 - 99.995 mole percent and y is 0.005 - 15 mole percent.
10. A polyol comprising the free radical polymerization product of vinyl acetate and a polyalklene oxide having an allyl glycidyl ether unit.
11. A polyol as set forth in claim 10 wherein the polyalklene oxide is selected from the group consisting of polyethylene oxide, polypropylene oxide, polybutylene oxide and polytetrahydrofuran.
12. A polyol as set forth in claim 10 wherein the polyalkylene oxide has a molecular weight ranging from about 200 to about 2000 grams per mole.
13. A polyol as set forth in claim 10 wherein the polyalkylene oxide is prepared from an initiator selected from the group consisting of methanol, solketal, isopropanol and hydrogen peroxide.
14. A copolymer comprising the reaction product of vinyl acetate and allyl glycidyl ether.
15. A copolymer as set forth in claim 14 having a viscosity ranging from about 5,000 to about 100,000 cP.
16. A copolymer as set forth in claim 14 having a viscosity ranging from about 40,000 to about 100,000 cP.
17. A composition of matter comprising:

a) a copolymer comprising the reaction product of vinyl acetate and allyl glycidyl ether, and b) a component comprising a hydroxyl-group containing compound, wherein said copolymer is uniformily dispersed in said component.
18. A composition of matter as set forth in claim 17 wherein said hydroxyl-group-containing compound comprises at least one selected from the group consisting of aliphatic glycols, dihydroxyl aromatics, bisphenols, hydroxyl terminated polyethers, polyesters and polyacetals.
19. A composition of matter as set forth in claim 17 wherein said copolymer comprises from about 2 to about 99 weight percent of said composition.
20. A composition of matter as set forth in claim 17 wherein said copolymer comprises from about 2 to about 20 weight percent of said composition.
21. A composition of matter as set forth in claim 17 wherein said copolymer comprises from about 5 to about 20 weight percent of said composition.
22. A composition of matter as set forth in claim 17 wherein said allyl glycidyl ether comprises from about 0.001 to about 50 mole percent of said copolymer.
23. A composition of matter as set forth in claim 17 wherein said allyl glycidyl ether comprises from about 0.005 to about 25 mole percent of said copolymer.
24. A composition of matter as set forth in claim 17 wherein said allyl glycidyl ether comprises from about 0.005 to about 15 mole percent of said copolymer.
25. A copolymer as set forth in claim 1 wherein said copolymer has an average molecular weight ranging from about 500 to about 5000.
26 A copolymer as set forth in claim 1 wherein said copolymer has an average molecular weight ranging from about 500 to about 2000.
27. A polyol as set forth in claim 10 wherein said polyol has an average molecular weight ranging from about 500 to about 5000.
28. A polyol as set forth in claim 10 wherein said polyol has an average molecular weight ranging from about 500 to about 2000.
29. A copolymer as set forth in claim 14 wherein said copolymer has an average molecular weight ranging from about 500 to about 5000.
30. A copolymer as set forth in claim 14 wherein said copolymer has an average molecular weight ranging from about 500 to about 2000.
31. A composition as set forth in claim 17 wherein said copolymer has an average molecular weight ranging from about 500 to about 5000.
32. A composition as set forth in claim 17 wherein said copolymer has an average molecular weight ranging from about 500 to about 2000.
33. A copolymer as set forth in claim 1 wherein said copolymer has a viscosity ranging from about 5000 to about 100,000 cP.
34. A copolymer as set forth in claim 1 wherein said copolymer has a viscosity ranging from about 40,000 to about 100,000 cP. -15-
35. A polyol as set forth in claim 10 wherein said polyol has a viscosity ranging from about 5000 to about 100,000 cP.
36. A polyol as set forth in claim 10 wherein said polyol has a viscosity ranging from about 40,000 to about 100,000 cP.
37. A composition of matter as set forth in claim 17 wherein said copolymer has a viscosity ranging from about 5000 to about 100,000.
38. A composition of matter as set forth in claim 17 wherein said copolymer has a viscosity ranging from about 40,000 to about 100,000 cP.
39. A copolymer as set forth in claim 1 further comprising a vinyl alcohol group present in an amount ranging from trace quantities to about five mole percent.
CA002032978A 1989-12-22 1990-12-21 Copolymers from polyalkylene oxides containing an allyl glycidyl ether reactive double bond and vinyl acetate Abandoned CA2032978A1 (en)

Applications Claiming Priority (2)

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US45554089A 1989-12-22 1989-12-22
US07/455,540 1989-12-22

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WO2008128209A1 (en) * 2007-04-12 2008-10-23 Designer Molecules, Inc. Polyfunctional epoxy oligomers

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US5770106A (en) 1998-06-23
GB2239249A (en) 1991-06-26
GB9025744D0 (en) 1991-01-09

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