Liquid benzoate ester compositions and aqueous polymer compositions containing same as plasticizers
View Patent ↗The addition of at least 20 weight percent of at least one member of a specified class of monobenzoates to at least one member of a specified class of dibenzoates that freeze at 28° C. or above results in a mixture that is both a liquid at this temperature and an unexpectedly effective plasticizer for many organic polymers. The plasticized polymer compositions are useful in various end use applications including adhesives and caulks.
1. A liquid ester composition comprising:
at least one monoester represented by the formula HXC(O)R 1 and at least one diester represented by the formula R 1 (O)CYC(O)R 1 ,
wherein X and Y are individually selected from the group consisting of —[OCH 2 CH 2 ] n O, and —OR 2 O—,
said diester is a solid at 28° C.,
R 1 is phenyl or substituted phenyl, wherein the substituent is selected from the group consisting of alkyl radicals containing from 1 to 4 carbon atoms and halogen,
R 2 is selected from the group consisting of linear alkylene containing 3 or 4 carbon atoms, —CH 2 CH(CH 3 )CH 2 — and —CH 2 C(CH 3 ) 2 CH 2 —;
n is 1, 2 or 3, and
wherein said composition is a liquid at 28° C.
2. A composition according to claim 1 wherein the combined concentration of all monoesters is at least 20 weight percent of said ester composition.
3. A composition according to claim 2 wherein said monoesters constitute from 20 to 99 weight percent of said ester composition.
4. A composition according to claim 1 wherein X and a portion of Y are identical and are selected from the group consisting of —OCH 2 CH 2 OCH 2 CH 2 O— and —OCH 2 CH(CH 3 )CH 2 O—.
5. A composition according to claim 4 wherein X and Y are —O(CH 2 CH 2 O) n — and said composition additionally comprises a mixture of the mono- and dibenzoates of dipropylene glycol.
6. A composition according to claim 1 wherein both X and Y are —OCH 2 CH(CH 3 )CH 2 O—.
7. A composition according to claim 1 wherein R 1 is phenyl.
8. A polymer composition comprising
A. an organic polymer and
B. an amount sufficient to plasticize said polymer of an ester composition that is a liquid at 28° C. and comprises:
at least one monoester represented by the formula HXC(O)R 1 and at least one diester represented by the formula R 1 (O)CYC(O)R 1 ,
wherein X and Y are individually selected from the group consisting of —[OCH 2 CH 2 ] n O and —OR 2 O—,
said diester is a solid at 28° C.,
R 1 is phenyl or substituted phenyl, wherein the substituent is selected from the group consisting of alkyl radicals containing from 1 to 4 carbon atoms and halogen,
R 2 is selected from the group consisting of linear alkylene containing 3 or 4 carbon atoms, —CH 2 CH(CH 3 )CH 2 — and —CH 2 C(CH 3 ) 2 CH 2 —;
n is 1, 2or 3, and wherein said composition is a liquid at 28° C.
9. A polymer composition according to claim 8 wherein said organic polymer is selected from the group consisting of homopolymers of vinyl esters and copolymers of these esters with olefins, esters derived from ethylenically unsaturated acids and mono- or polyhydric alcohols, polyesters, polyamides and copolymers derived from ethylenically unsaturated acids or esters thereof and ethylenically unsaturated hydrocarbons.
10. A composition according to claim 9 wherein the combined concentration of all monoesters is at least 20 weight percent, based on the total weight of said ester composition.
11. A composition according to claim 10 wherein said monoesters constitute from 20 to 99 weight percent of said ester composition.
12. A composition according to claim 8 wherein X and a portion of Y are identical and are selected from the group consisting of —OCH 2 CH 2 OCH 2 CH 2 O— and OCH 2 CH(CH 3 )CH 2 O—.
13. A composition according to claim 12 wherein X and Y are —O(CH 2 CH 2 O) n — and said composition additionally comprises a mixture of the mono- and dibenzoates of dipropylene glycol.
14. A composition according to claim 12 wherein both X and Y are —OCH 2 CH(CH 3 )CH 2 O—.
15. A composition according to claim 8 wherein R 1 is phenyl.
16. A composition according to claim 8 wherein said polymer is present as an aqueous dispersion, an aqueous emulsion, a dispersion in a non-aqueous liquid, a solid or a molten material.
17. A polymer composition comprising
A. an organic polymer and
B. an amount sufficient to plasticize said polymer of an ester composition that is a liquid at 28° C. and comprises:
at least one monoester represented by the formula HXC(O)R 1 and
at least one diester represented by the formula R 1 (O)CYC(O)R 1 ,
wherein X and Y are individually selected from the group consisting of
—[OCH 2 CH 2 ] p O and —OR 2 O—,
said diester is a solid at 28° C.,
R 1 is phenyl or substituted phenyl, wherein the substituent is selected from the group consisting of alkyl radicals containing from 1 to 4 carbon atoms and halogen,
R 2 is selected from the group consisting of linear alkylene containing 3 or 4 carbon atoms, —CH 2 CH(CH 3 )CH 2 — and —CH 2 C(CH 3 ) 2 CH 2 —;
p is 1, 2 or 3, and
wherein said composition is a liquid at 28° C. and said polymer is present as an aqueous emulsion, a non-aqueous dispersion, a non-aqueous solution, or a molten material.