# US 2010/0168230 A1 · Methods for Making Organozinc Salts and Compositions Containing the Same

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- Number: US 2010/0168230 A1
- Document ID: US20100168230A1
- Status: Published application
- Kind: A1
- Application number: 12/346,535
- Filed: 2008-12-30
- Published: 2010-07-01
- Earliest claimed: 2008-12-30
- Inventors: Raymond L. Nip
- Web page: https://patentgrep.com/patent/US20100168230A1

## CPC

- C07F 3/003: {without C-Metal linkages}
- A01N 47/14: Di-thio analogues thereof
- C07C 51/412: {by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part}
- C07C 333/16: Salts of dithiocarbamic acids
- Y10T 428/2991: Coated
- Y10T 428/2995: Silane, siloxane or silicone coating
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Organic zinc salts and mixtures thereof, organic zinc salt coated particles, methods of preparing organic zinc salts and organic zinc salt coated particles, and various applications of such coated particles, including applications in rubber, other polymeric materials, and pesticides and/or fungicides are disclosed.

## Claims

### Claim 1

A method for preparing organic zinc salt, comprising the steps of:
a) mixing a zinc ammonia complex solution with one or more organic acids and/or soluble organic acid salts to form a mixture;
b) agitating (and optionally heating) the mixture to at least partially remove ammonia from the mixture, thereby forming said organic zinc salt;
c) optionally, cooling the mixture to a temperature of from about 5° C. to 30° C.;
d) filtering the mixture to isolate said organic zinc salt;
e) optionally, washing the isolated organic zinc salt;
f) drying the isolated organic zinc salt; and
g) optionally, milling the isolated organic zinc salt.

### Claim 2 (depends on 1)

The method of claim 1, wherein said zinc ammonia complex solution comprises a zinc ammonia carbonate complex, and step (b) at least partially removes carbon dioxide from the mixture.

### Claim 3 (depends on 2)

The method of claim 2, further comprising preparing the zinc ammonia carbonate complex from a zinc source, ammonia or an ammonia derivative, and carbon dioxide or a carbon dioxide derivative, wherein said zinc ammonia carbonate complex solution contains zinc in a concentration of from about 1% to 15% by weight, ammonia in a concentration of from 1% to 20% by weight, and carbon dioxide in a concentration of from 0 to 10% by weight.

### Claim 4 (depends on 3)

The method of claim 3, wherein the zinc source is selected from the group consisting of zinc oxide, zinc carbonate, electric arc furnace dust and zinc ash.

### Claim 5 (depends on 1)

The method of claim 1, wherein the one or more organic acids and/or salts thereof consist essentially of a salt of an organic acid, and the method further comprises preparing said salt of said organic acid by reacting said organic acid with sodium hydroxide, potassium hydroxide, or an ammonium hydroxide.

### Claim 6 (depends on 1)

The method of claim 1, wherein step (b) further comprises heating the mixture at a temperature of from about 40° C. to 150° C.

### Claim 7 (depends on 1)

The method of claim 1, wherein said isolated organozinc organic zinc salt is insoluble or sparingly soluble in water.

### Claim 8 (depends on 1)

The method of claim 1, wherein said one or more organic acids are selected from the group consisting of C7-C24 aliphatic carboxylic acids, aromatic carboxylic acids, and 2-mercaptobenzothiazole.

### Claim 9 (depends on 8)

The method of claim 8, wherein said one or more organic acids comprises a mixture of one or more C7-C24 aliphatic carboxylic acids and one or more aromatic carboxylic acids.

### Claim 10 (depends on 1)

The method of claim 1, comprising drying the isolated organic zinc salt at a temperature of from about 50° C. to 200° C.

### Claim 11 (depends on 1)

The method of claim 1, wherein mixing said zinc ammonia complex solution with said one or more organic acids further comprises generating said one or more organic acids in situ.

### Claim 12 (depends on 11)

The method of claim 11, wherein mixing said zinc ammonia complex solution with said one or more organic acids and generating said one or more organic acids in situ comprises:
a) dissolving an amine in water;
b) adding an ammonium hydroxide solution to form a second solution;
c) adding a zinc ammonia carbonate complex or solution thereof to the second solution;
d) optionally, adding one or more emulsifiers; and
e) adding carbon disulfide at a temperature of less than 40° C. to form a mixture and agitating the mixture to precipitate the zinc salt.

### Claim 13 (depends on 12)

The method of claim 12, wherein said ammonium hydroxide solution comprises ammonium hydroxide in an amount of from about 1% to 10% by weight.

### Claim 14 (depends on 12)

The method of claim 12, comprising adding said zinc ammonia carbonate complex or solution thereof to said second solution after adding said carbon disulfide.

### Claim 15 (depends on 12)

The method of claim 12, wherein adding a zinc ammonia carbonate complex or solution thereof comprises adding a zinc source, ammonia, and optionally carbon dioxide to form said zinc ammonia carbonate complex.

### Claim 16 (depends on 12)

The method of claim 12, wherein said amine comprises a disubstituted amine selected from the group consisting of dialkylamines, diarylamines, diaralkylamines, and ethylene diamine.

### Claim 17 (depends on 16)

The method of claim 16, wherein said amine is selected from the group consisting of dimethylamine, diethylamine, dibenzylamine, dibutylamine and ethylenediamine, and said zinc salt is selected from the group consisting of dimethyldithiocarbamate, zinc diethyldithiocarbamate, zinc dibenzyldithiocarbamate, zinc dibutyldithiocarbamate and zinc ethylenebisdithiocarbamate.

### Claim 18

A method of making coated particles, comprising:
a) mixing a zinc ammonia carbonate complex solution with one or more organic acids and/or salts thereof, thereby forming a mixture;
b) mixing substrate particles with the mixture to form a suspension;
c) agitating (and optionally heating) the suspension to remove substantially all ammonia and/or carbon dioxide from the mixture, thereby forming said coated particles, having a coating thereon comprising one or more organic zinc salts in an amount of from 1 to 30 wt. % of the coated particles;
d) optionally, heating the coated particles at a temperature of from about 50° C. to 200° C.; and
e) optionally, milling the coated particles.

### Claim 19 (depends on 18)

The method of claim 18, wherein said coating further comprises zinc oxide and/or zinc carbonate.

### Claim 20 (depends on 18)

The method of claim 18, wherein said substrate particles are selected from the group consisting of silica, clay, kaolin, talc, aluminum silicate, calcium carbonate and mixtures thereof.

### Claim 21 (depends on 18)

The method of claim 18, further comprising preparing the zinc ammonia carbonate complex from a zinc source, ammonia or an ammonia derivative, and carbon dioxide or a carbon dioxide derivative, wherein said mixture contains zinc in a concentration of from about 1% to 15% by weight, ammonia in a concentration of from 1% to 20% by weight, and carbon dioxide in a concentration of from 0 to 10% by weight.

### Claim 22 (depends on 21)

The method of claim 21, wherein the zinc source is selected from the group consisting of zinc oxide, zinc carbonate, electric arc furnace dust and zinc ash.

### Claim 23 (depends on 18)

The method of claim 18, wherein said one or more organic acids are selected from the group consisting of C7-C24 aliphatic carboxylic acids, aromatic carboxylic acids, 2-mercaptobenzothiazole, and substituted dithiocarbamic acids.

### Claim 24 (depends on 19)

The method of claim 19, wherein said mixing comprises spraying said mixture on the substrate particles.

### Claim 25

A coated particle, comprising:
a) a particle core selected from the group consisting of silica, clay, kaolin, talc, aluminum silicate, calcium carbonate, carbon black and mixtures thereof; and
b) a coating thereon, comprising a zinc salt of an organic acid in an amount of from 2 to 30 wt. % of the coated particle.

### Claim 26 (depends on 25)

A composition, comprising:
a) a rubber;
b) the coated particles of claim 25, in an amount of from 2 to 80 phr of the rubber; and
c) optionally, a silane coupling agent.

### Claim 27 (depends on 26)

The composition of claim 26, wherein the rubber comprises a natural rubber, a synthetic rubber, or a mixture thereof.

### Claim 28 (depends on 26)

A rubber product selected from the group consisting of a tire, a shoe sole, a rubber band, a rubber thread, a belt, an automobile part, a roller, and a latex product, comprising the composition of claim 26.

### Claim 29 (depends on 1)

A composition, comprising:
a) a rubber;
b) one or more organic zinc salts made by the method of claim 1, in an amount of from 0.1 to 4 phr of the rubber;
c) optionally, a filler material selected from the group consisting of silica, clay, kaolin, talc, aluminum silicate, calcium carbonate, carbon black and mixtures thereof, and
d) optionally, a silane coupling agent and/or other rubber processing aid.

### Claim 30 (depends on 29)

The composition of claim 29, wherein the rubber comprises a natural rubber, a synthetic rubber, rubber latex, or a mixture thereof.

### Claim 31 (depends on 29)

The composition of claim 29, wherein said one or more organic zinc salts comprise one or more of the following:
a) a zinc salt of a fatty acid;
b) a mixture of zinc salts of one or more C7-C18 aliphatic carboxylic acids and one or more aromatic carboxylic acids;
c) zinc 2-mercaptobenzothiazole; or
d) a zinc dithiocarbamate.

### Claim 32 (depends on 31)

A rubber product selected from the group consisting of a tire, a shoe sole, a rubber band, a rubber thread, a belt, an automobile part, a roller, a latex glove, and a latex rubber thread, comprising the composition of claim 31.

### Claim 33 (depends on 12)

A fungicide or a pesticide, wholly or partially comprising zinc dimethyldithiocarbamate and/or zinc ethylenebisdithiocarbamate prepared according to the method of claim 12.