Urea phenyl derivatives and their use as polypropylene nucleating agents
View Patent ↗Disclosed herein are urea phenyl derivatives of the formula: wherein each R is an independently selected hydrocarbyl group and n is 2 or 3, and their use as nucleating agents for propylene polymers.
1. A composition comprising:
(A) a crystallizable polypropylene polymer, and
(B) about 0.001 to about 5%, relative to the weight of component (A), of at least one urea phenyl derivative of the formula:
wherein each R is an independently selected hydrocarbyl group and n is 2 or 3.
2. The composition of claim 1 wherein the urea phenyl derivative is of the formula:
wherein R 1 and R 2 are independently selected hydrocarbyl groups.
3. The composition of claim 1 wherein the urea phenyl derivative is of the formula:
wherein R 1 , R 2 , and R 3 are independently selected hydrocarbyl groups.
4. The composition of claim 1 wherein each R is independently selected from the group consisting of: C 1 -C 20 alkyl; C 1 -C 20 alkyl substituted by C 1 -C 20 alkylamino, di(C 1 -C 20 alkyl)amino, C 1 -C 20 alkyloxy or hydroxy; {poly(C 2 -C 4 alkoxy)}-(C 2 -C 4 alkyl); C 2 -C 20 alkenyl; C 3 -C 12 cycloalkyl; C 3 -C 12 cycloalkyl substituted by 1, 2 or 3 C 1 -C 20 alkyl; cyclohexylmethyl; cyclohexylmethyl substituted by 1, 2 or 3 C 1 -C 20 alkyl; C 3 -C 20 cycloalkenyl; C 3 -C 12 cycloalkenyl substituted by 1, 2 or 3 C 1 -C 20 alkyl; phenyl; phenyl substituted by 1, 2 or 3 radicals selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 alkyloxy, hydroxy, phenylamino, acylamino, phenylazo; phenyl substituted by halogens; C 7 -C 9 phenylalkyl; C 7 -C 9 phenylalkyl which is substituted on the phenyl by 1, 2 or 3 radicals selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 alkoxy, and hydroxy; naphthyl; naphthyl substituted by C 1 -C 20 alkyl; adamantyl; adamantyl substituted by C 1 -C 20 alkyl; and a 5- or 6-membered heterocyclic group.
5. The composition of claim 2 wherein R 1 and R 2 are the same and are selected from the group consisting of 1,2-dimethylpropyl, 3-methylbutyl, and cyclopentyl.
6. The composition of claim 3 wherein R 1 , R 2 , and R 3 are the same and are selected from the group consisting of 1,2-dimethylpropyl, 3-methylbutyl, and cyclopentyl.
7. The composition of claim 1 further comprising about 0.001 to about 5%, relative to the weight of component (A), of at least one additional nucleating agent selected from the group consisting of: (1) Aromatic sorbitol acetals; (2) Nucleating agents based upon salts of phosphoric acid; (3) Nucleating agents based upon salts of carboxylic acids; (4) Nucleating agents based upon carboxy aluminum-hydroxide; (5) Nucleating agents based upon salts of rosin/adiabatic acid; (6) Zinc (II) monoglycerolate; (7) Nucleating agents based upon diamide compounds; and (8) Nucleating agents based upon trimesic acid derivatives.
8. A method for reducing haze in crystallizable polypropylene polymers comprising adding to said polymer about 0.001 to about 5%, relative to the weight of the polymer, of at least one urea phenyl derivative of the formula:
wherein each R is an independently selected hydrocarbyl group and n is 2 or 3.
9. The method of claim 8 wherein the urea phenyl derivative is of the formula:
wherein R 1 and R 2 are independently selected hydrocarbyl groups.
10. The method of claim 8 wherein the urea phenyl derivative is of the formula:
wherein R 1 , R 2 , and R 3 are independently selected hydrocarbyl groups.
11. The method of claim 8 wherein each R is independently selected from the group consisting of: C 1 -C 20 alkyl; C 1 -C 20 alkyl substituted by C 1 -C 20 alkylamino, di(C 1 -C 20 alkyl)amino, Ci-C 20 alkyloxy or hydroxy; {poly(C 2 -C 4 alkoxy) }-(C 2 -C 4 alkyl); C 2 -C 20 alkenyl; C 3 -C 12 cycloalkyl; C 3 -C 12 cycloalkyl substituted by 1, 2 or 3 C 1 -C 20 alkyl; cyclohexylmethyl; cyclohexylmethyl substituted by 1, 2 or 3 C 1 -C 20 alkyl; C 3 -C 20 cycloalkenyl; C 3 -C 12 cycloalkenyl substituted by 1, 2 or 3 C 1 -C 20 alkyl; phenyl; phenyl substituted by 1, 2 or 3 radicals selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 alkyloxy, hydroxy, phenylamino, acylamino, phenylazo; phenyl substituted by halogens; C 7 -C 9 phenylalkyl; C 7 -C 9 phenylalkyl which is substituted on the phenyl by 1, 2 or 3 radicals selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 alkoxy, and hydroxy; naphthyl; naphthyl substituted by C 1 -C 20 alkyl; adamantyl; adamantyl substituted by C 1 -C 20 alkyl; and a 5- or 6-membered heterocyclic group.
12. The method of claim 9 wherein R 1 and R 2 are the same and are selected from the group consisting of 1,2-dimethylpropyl, 3-methylbutyl, and cyclopentyl.
13. The method of claim 10 wherein R 1 , R 2 , and R 3 are the same and are selected from the group consisting of 1,2-dimethylpropyl, 3-methylbutyl, and cyclopentyl.
14. A composition of matter comprising a urea phenyl derivative of the formula:
wherein R 1 and R 2 are the same and are selected from the group consisting of 1,2-dimethylpropyl, 3-methylbutyl, and cyclopentyl.
15. A composition of matter comprising a urea phenyl derivative of the formula:
wherein R 1 , R 2 , and R 3 are the same and are selected from the group consisting of 1,2-dimethylpropyl, 3-methylbutyl, and cyclopentyl.