Compatibilizers for composites of PVC and cellulosic materials
View Patent ↗Disclosed herein is a method for improving the physical properties of cellulose fiber-containing material/PVC composites comprising adding to said composites an effective amount of at least one compatibilizer comprising an organometallic zirconium compound. The preferred organometallic zirconium compound is cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate. Articles of manufacture comprising such composites are also disclosed.
1. A method for improving the physical properties of cellulose fiber-containing material/PVC composites comprising adding to said composites 0.1 to 90 phr of at least one compatibilizer comprising an organometallic zirconium compound.
2. The method of claim 1 wherein the organometallic zirconium compound is selected from the group consisting of:
cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate,
cyclo(dioctyl)pyrophosphato dioctyl zirconate,
cycloneopentyl cyclo(dimethylaminoethyl)pyrophosphate zirconate dimesyl salt,
tetra(2,2diallyloxymethyl)butyl di(ditridecyl)phosphito zirconate,
neopentyl(diallyl)oxytrineodecanoyl zirconate,
neopentyl(diallyl)oxytri(dodecyl)benzene sulfonyl zirconate,
neopentyl(diallyl)oxytri(dioctyl)phosphato zirconate,
neopentyl(diallyl)oxytri(dioctyl)pyrophosphato zirconate,
neopentyl(diallyl)oxytri(N-ethylenediamino)ethyl zirconate,
neopentyl(diallyl)oxytri-(m-amino)phenyl zirconate,
neopentyl(diallyl)oxytrimethylacryl zirconate,
neopentyl(diallyl)oxytriacryl zirconate,
dineopentyl(diallyl)oxydiparamino benzoyl zirconate,
dineopentyl(diallyl)oxydi(3-mercapto)propionic zirconate,
2,2-dimethyl1,3propanediolatobis(dioctyl)pyrophosphato-O (adduct) 2 moles N,N-dimethylamino-alkyl propenoamide zirconate,
(2-ethyl,2-propanolatomethyl)1,3-propanediolato cyclobis2-dimethylamino pyrophosphato-O,O adduct with 2 moles of methanesulfonic acid zirconate,
tetrakis2,2(bis-2-propenolatomethyl)butanolato, adduct with 2 moles of ditridecyl hydrogen phosphite zirconate,
2-ethyl2-propenolatomethyl1,3-propanoediolato cyclodi2,2-(bis-2-propenolatomethyl)butanolato pyrophosphato-O,O bis2-ethylhexanolato cyclo(di-2-ethylhexyl)pyrophosphato zirconate,
2,2(bis-2-propenolatomethyl)butanolatotrisneodecanoato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dodecyl)benzenesulfonato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O, 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris2-methyl-2-propenato-O zirconate, 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)pyrophosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolato pyrophosphato-O,O zirconate,
2,2(bis-2-propenolato butanolatotri2-propenolato-O, 2,2(bis-2-propenolatomethyl)butanolatotri(2-ethylenediamino)ethylato zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(para amino benzoato-O)zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(3-mercapto) propionato-O zirconate,
1,1(bis-2-propenolatomethyl)butanolatotris(2-amino)phenylato zirconate, and mixtures thereof.
3. The method of claim 2 wherein the organometallic zirconium compound is cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate.
4. The method of claim 1 wherein the cellulose fiber-containing material is selected from the group consisting of wood flour, wood fiber, refined cellulose fiber, virgin or recycled, flax, rice hulls, sisal, jute, and kenaf.
5. The method of claim 4 wherein the organometallic zirconium compound is selected from the group consisting of:
cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate,
cyclo(dioctyl)pyrophosphato dioctyl zirconate,
cycloneopentyl cyclo(dimethylaminoethyl)pyrophosphate zirconate dimesyl salt, tetra(2,2diallyloxymethyl)butyl di(ditridecyl)phosphito zirconate,
neopentyl(diallyl)oxytrineodecanoyl zirconate,
neopentyl(diallyl)oxytri(dodecyl)benzene sulfonyl zirconate,
neopentyl(diallyl)oxytri(dioctyl)phosphato zirconate,
neopentyl(diallyl)oxytri(dioctyl)pyrophosphato zirconate,
neopentyl(diallyl)oxytri(N-ethylenediamino)ethyl zirconate,
neopentyl(diallyl)oxytri-(m-amino)phenyl zirconate,
neopentyl(diallyl)oxytrimethylacryl zirconate,
neopentyl(diallyl)oxytriacryl zirconate,
dineopentyl(diallyl)oxydiparamino benzoyl zirconate,
dineopentyl(diallyl)oxydi(3-mercapto)propionic zirconate,
2,2-dimethyl1,3propanediolatobis(dioctyl)pyrophosphato-O (adduct) 2 moles N,N-dimethylamino-alkyl propenoamide zirconate,
(2-ethyl,2-propanolatomethyl)1,3-propanediolato cyclobis2-dimethylamino pyrophosphato-O,O adduct with 2 moles of methanesulfonic acid zirconate,
tetrakis2,2(bis-2-propenolatomethyl)butanolato, adduct with 2 moles of ditridecyl hydrogen phosphite zirconate,
2-ethyl2-propenolatomethyl1,3-propanoediolato cyclodi2,2-(bis-2-propenolatomethyl)butanolato pyrophosphato-O,O bis2-ethylhexanolato cyclo(di-2-ethylhexyl)pyrophosphato zirconate,
2,2(bis-2-propenolatomethyl)butanolatotrisneodecanoato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dodecyl)benzenesulfonato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris2-methyl-2-propenato-O zirconate, 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)pyrophosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolato pyrophosphato-O,O zirconate,
2,2(bis-2-propenolato butanolatotri2-propenolato-O, 2,2(bis-2-propenolatomethyl)butanolatotri(2-ethylenediamino)ethylato zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(para amino benzoato-O)zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(3-mercapto) propionato-O zirconate,
1,1(bis-2-propenolatomethyl)butanolatotris(2-amino)phenylato zirconate, and mixtures thereof.
6. The method of claim 5 wherein the organometallic zirconium compound is cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate.
7. The method of claim 1 wherein the composites further comprise at least one additive selected from the group consisting of heat stabilizers, lubricants, impact modifiers, processing aids, antioxidants, fillers, pigments, and mold release agents.
8. The method of claim 7 wherein the organometallic zirconium compound is selected from the group consisting of:
cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate,
cyclo(dioctyl)pyrophosphato dioctyl zirconate,
cycloneopentyl cyclo(dimethylaminoethyl)pyrophosphate zirconate dimesyl salt,
tetra(2,2diallyloxymethyl)butyl di(ditridecyl)phosphito zirconate,
neopentyl(diallyl)oxytrineodecanoyl zirconate,
neopentyl(diallyl)oxytri(dodecyl)benzene sulfonyl zirconate,
neopentyl(diallyl)oxytri(dioctyl)phosphato zirconate,
neopentyl(diallyl)oxytri(dioctyl)pyrophosphato zirconate,
neopentyl(diallyl)oxytri(N-ethylenediamino)ethyl zirconate,
neopentyl(diallyl)oxytri-(m-amino)phenyl zirconate,
neopentyl(diallyl)oxytrimethylacryl zirconate,
neopentyl(diallyl)oxytriacryl zirconate,
dineopentyl(diallyl)oxydiparamino benzoyl zirconate,
dineopentyl(diallyl)oxydi(3-mercapto)propionic zirconate,
2,2-dimethyl1,3propanediolatobis(dioctyl)pyrophosphato-O (adduct) 2 moles N,N-dimethylamino-alkyl propenoamide zirconate,
(2-ethyl,2-propanolatomethyl)1,3-propanediolato cyclobis2-dimethylamino pyrophosphato-O,O adduct with 2 moles of methanesulfonic acid zirconate,
tetrakis2,2(bis-2-propenolatomethyl)butanolato, adduct with 2 moles of ditridecyl hydrogen phosphite zirconate,
2-ethyl2-propenolatomethyl1,3-propanoediolato cyclodi2,2-(bis-2-propenolatomethyl)butanolato pyrophosphato-O,O bis2-ethylhexanolato cyclo(di-2-ethylhexyl)pyrophosphato zirconate,
2,2(bis-2-propenolatomethyl)butanolatotrisneodecanoato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dodecyl)benzenesulfonato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O, 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris2-methyl-2-propenato-O zirconate, 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)pyrophosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolato pyrophosphato-O,O zirconate,
2,2(bis-2-propenolato butanolatotri2-propenolato-O, 2,2(bis-2-propenolatomethyl)butanolatotri(2-ethylenediamino)ethylato zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(para amino benzoato-O)zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(3-mercapto) propionato-O zirconate,
1,1(bis-2-propenolatomethyl)butanolatotris(2-amino)phenylato zirconate, and mixtures thereof.
9. The method of claim 8 wherein the organometallic zirconium compound is cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate.
10. A composition comprising a cellulose fiber-containing material/PVC composite and 0.1 to 90 phr of at least one compatibilizer comprising an organometallic zirconium compound.
11. The composition of claim 10 wherein the organometallic zirconium compound is selected from the group consisting of:
cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate,
cyclo(dioctyl)pyrophosphato dioctyl zirconate,
cycloneopentyl cyclo(dimethylaminoethyl)pyrophosphate zirconate dimesyl salt,
tetra(2,2diallyloxymethyl)butyl di(ditridecyl)phosphito zirconate,
neopentyl(diallyl)oxytrineodecanoyl zirconate,
neopentyl(diallyl)oxytri(dodecyl)benzene sulfonyl zirconate,
neopentyl(diallyl)oxytri(dioctyl)phosphato zirconate,
neopentyl(diallyl)oxytri(dioctyl)pyrophosphato zirconate,
neopentyl(diallyl)oxytri(N-ethylenediamino)ethyl zirconate,
neopentyl(diallyl)oxytri-(m-amino)phenyl zirconate,
neopentyl(diallyl)oxytrimethylacryl zirconate,
neopentyl(diallyl)oxytriacryl zirconate,
dineopentyl(diallyl)oxydiparamino benzoyl zirconate,
dineopentyl(diallyl)oxydi(3-mercapto)propionic zirconate,
2,2-dimethyl1,3propanediolatobis(dioctyl)pyrophosphato-O (adduct) 2 moles N,N-dimethylamino-alkyl propenoamide zirconate,
(2-ethyl,2-propanolatomethyl)1,3-propanediolato cyclobis2-dimethylamino pyrophosphato-O,O adduct with 2 moles of methanesulfonic acid zirconate,
tetrakis2,2(bis-2-propenolatomethyl)butanolato, adduct with 2 moles of ditridecyl hydrogen phosphite zirconate,
2-ethyl2-propenolatomethyl1,3-propanoediolato cyclodi2,2-(bis-2-propenolatomethyl)butanolato pyrophosphato-O,O bis2-ethylhexanolato cyclo(di-2-ethylhexyl)pyrophosphato zirconate,
2,2(bis-2-propenolatomethyl)butanolatotrisneodecanoato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dodecyl)benzenesulfonato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O, 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris2-methyl-2-propenato-O zirconate, 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)pyrophosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolato pyrophosphato-O,O zirconate,
2,2(bis-2-propenolato butanolatotri2-propenolato-O, 2,2(bis-2-propenolatomethyl)butanolatotri(2-ethylenediamino)ethylato zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(para amino benzoato-O)zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(3-mercapto) propionato-O zirconate,
1,1(bis-2-propenolatomethyl)butanolatotris(2-amino)phenylato zirconate, and mixtures thereof.
12. The composition of claim 11 wherein the organometallic zirconium compound is cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate.
13. The composition of claim 10 wherein the cellulose fiber-containing material is selected from the group consisting of wood flour, wood fiber, refined cellulose fiber, virgin or recycled, flax, rice hulls, sisal, jute, and kenaf.
14. The composition of claim 10 wherein the composites further comprise at least one additive selected from the group consisting of heat stabilizers, lubricants, impact modifiers, processing aids, antioxidants, fillers, pigments, and mold release agents.
15. An article of manufacture comprising a composition comprising a cellulose fiber-containing material/PVC composite and 0.1 to 90 phr of at least one compatibilizer comprising an organometallic zirconium compound.
16. The article of claim 15 wherein the organometallic zirconium compound is selected from the group consisting of:
cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate,
cyclo(dioctyl)pyrophosphato dioctyl zirconate,
cycloneopentyl cyclo(dimethylaminoethyl)pyrophosphate zirconate dimesyl salt,
tetra(2,2diallyloxymethyl)butyl di(ditridecyl)phosphito zirconate,
neopentyl(diallyl)oxytrineodecanoyl zirconate,
neopentyl(diallyl)oxytri(dioctyl)phosphato zirconate,
neopentyl(diallyl)oxytri(dioctyl)pyrophosphato zirconate,
neopentyl(diallyl)oxytri(N-ethylenediamino)ethyl zirconate,
neopentyl(diallyl)oxytri-(m-amino)phenyl zirconate,
neopentyl(diallyl)oxytrimethylacryl zirconate,
neopentyl(diallyl)oxytriacryl zirconate,
dineopentyl(diallyl)oxydiparamino benzoyl zirconate,
dineopentyl(diallyl)oxydi(3-mercapto)propionic zirconate,
2,2-dimethyl1,3propanediolatobis(dioctyl)pyrophosphato-O (adduct) 2 moles N,N-dimethylamino-alkyl propenoamide zirconate,
(2-ethyl,2-propanolatomethyl)1,3-propanediolato cyclobis2-dimethylamino pyrophosphato-O,O adduct with 2 moles of methanesulfonic acid zirconate,
tetrakis2,2(bis-2-propenolatomethyl)butanolato, adduct with 2 moles of ditridecyl hydrogen phosphite zirconate,
2-ethyl2-propenolatomethyl1,3-propanoediolato cyclodi2,2-(bis-2-propenolatomethyl)butanolato pyrophosphato-O,O bis2-ethylhexanolato cyclo(di-2-ethylhexyl)pyrophosphato zirconate,
2,2(bis-2-propenolatomethyl)butanolatotrisneodecanoato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dodecyl)benzenesulfonato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O, 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)phosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolatotris2-methyl-2-propenato-O zirconate, 2,2(bis-2-propenolatomethyl)butanolatotris(dioctyl)pyrophosphato-O zirconate,
2,2(bis-2-propenolatomethyl)butanolato pyrophosphato-O zirconate,
2,2(bis-2-propenolato butanolatotri2-propenolato-O, 2,2(bis-2-propenolatomethyl)butanolatotri(2-ethylenediamino)ethylato zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(para amino benzoato-O)zirconate,
bis2,2(bis-2-propenolatomethyl)butanolatobis(3-mercapto) propionato-O zirconate,
1,1(bis-2-propenolatomethyl)butanolatotris(2-amino)phenylato zirconate, and mixtures thereof.
17. The article of claim 16 wherein the organometallic zirconium compound is cyclo[dineopentyl(diallyl)]pyrophosphato dineopentyl(diallyl)zirconate.
18. The article of claim 15 wherein the cellulose fiber-containing material is selected from the group consisting of wood flour, wood fiber, refined cellulose fiber, virgin or recycled, flax, rice hulls, sisal, jute, and kenaf.
19. The article of claim 15 wherein the composites further comprise at least one additive selected from the group consisting of heat stabilizers, lubricants, impact modifiers, processing aids, antioxidants, fillers, pigments, and mold release agents.
20. The method of claim 1 wherein 0.3 to 15 phr of the organometallic zirconium compound is added to the composite.
21. The method of claim 1 wherein 0.2% to 0.3% weight percent of the organometallic zirconium compound, based on the total weight of the composite, is added to the composite.
22. The composition of claim 10 wherein the compatibilizer comprises 0.3 to 15 phr of the organometallic zirconium.
23. The composition of claim 10 wherein the compatibilizer comprises 0.2% to 0.3% weight percent of the organometallic zirconium compound, based on the total weight of the composite.
24. The article of claim 15 wherein the compatibilizer comprises 0.3 to 15 phr of the organometallic zirconium.
25. The article of claim 15 wherein the compatibilizer comprises 0.2% to 0.3% weight percent of the organometallic zirconium compound, based on the total weight of the composite.