Low-emission formaldehyde donor preparations and use thereof

• US 20040082473A1
• Filed: 09/16/2003
• Published: 04/29/2004
• Est. Priority Date: 09/24/2002
• Status: Active Grant

• Current Assignee: Schulke & Mayr GmbH
• Original Assignee: Air Liquide Sante International (L'Air Liquide SA)
• Inventors: Krull, Ingo, Beilfuss, Wolfgang, Gradtke, Ralf, Weber, Klaus
• Granted Patent: US 8,568,754 B2
• Time in Patent Office: Days
• US Class Current: 504/114
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/00 Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application , e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
• CPC Class Codes: A01N 31/04 Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
• CPC Class Codes: A01N 31/08 Oxygen or sulfur directly attached to an aromatic ring system
• CPC Class Codes: A01N 35/02 containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
• CPC Class Codes: A01N 37/36 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
• CPC Class Codes: A01N 37/40 having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
• CPC Class Codes: A01N 39/00 Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or , e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 43/76 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 47/28 Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< isoureas, isothioureas A01N47/42
• CPC Class Codes: A01N 47/34 containing the groups , e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
• CPC Class Codes: A01N 59/14 Boron; Compounds thereof

Abstract

The invention relates to a preservative with reduced formaldehyde emission which comprises

a) at least one formal and

b) at least one emission-reducing additive which is chosen from urea, urea derivatives, amino acids, guanidine and guanidine derivatives,

where the preservative

(i) comprises no iodopropynyl compound and

(ii) no derivative of 1H-benzimidazol-2-carbamic acid,

and to a process for the preparation of the preservative and to the use of the preservative in a technical product.

Claims

1. Preservative with reduced formaldehyde emission which comprises

a) at least one formal and

b) at least one emission-reducing additive which is chosen from urea, urea derivatives, amino acids, guanidine and guanidine derivatives,

where the preservative

(i) comprises no iodopropynyl compound and

(ii) no derivative of 1H-benzimidazol-2-carbamic acid.

2. Preservative according to claim 1, characterized in that the formal is a N- and/or O-formal.

3. Preservative according to claim 1 or claim 2, characterized in that the formal is chosen from (ethylenedioxy)dimethanol, benzyl alcohol hemiformal, propylene glycol hemiformal and butyl diglycol hemiformal.

4. Preservative according to one of the preceding claims, characterized in that the formal is chosen from N,N′

,N″

-tris(hydroxyethyl)hexahydrotriazine, N,N′

,N″

-tris(β

-hydroxypropyl)hexahydrotriazine and N,N′

-methylenebis(5-methyloxazolidine).

5. Preservative according to one of the preceding claims, characterized in that the emission-reducing additive is chosen from glycoluril, tetramethylolglycoluril, dimethylhydantoin, dimethyloldimethylhydantoin, dimethylolurea, tetramethanolurea, imdazolidinylurea and diazolidinylurea.

6. Preservative according to one of the preceding claims, characterized in that it also comprises c) at least one odour-modifying additive which is chosen from alcohols, glycols and glycol ethers, in particular phenoxyethanol, phenoxypropanols, benzyl alcohol, phenethyl alcohol, phenylpropanols, phenylbutanols and phenylpentanols.

7. Preservative according to one of the preceding claims, characterized in that it also comprises d) at least one biocide which is chosen from boric esters, boric acid salts, lactic acid derivatives, isothiazolones, pyridine derivatives, phenols and parabens.

8. Preservative according to one of the preceding claims, characterized in that it also comprises e) at least one additive which is chosen from solvents, solubility promoters, corrosion inhibitors, alkalinizing agents, dyes, perfumes, viscosity modifying agents, foam inhibitors, emulsifiers and antioxidants.

9. Preservative according to one of the preceding claims, characterized in that the weight ratio a):

b) is in the range from 500;

1 to 1;

1, preferably 200;

1 to 5;

1, more preferably 100;

1 to 10;

1 and in particular 50;

1 to 20;

1.

10. Preservative according to one of the preceding claims,characterized in that it comprises 10% by weight of water or less, preferably 5% by weight or less, in particular 1% by weight or less of water, particular preference being given to anhydrous preservatives.

11. Preservative according to one of the preceding claims, characterized in that it comprises

a) 90 to 99% by weight, preferably 92 to 98% by weight, more preferably 93 to 97% by weight, in particular about 95% by weight, of N,N′

-methylenebis(5-methyloxazolidine) and

b) 1 to 10% by weight, preferably 2 to 8% by weight, more preferably 3 to 7% by weight, in particular about 5% by weight, of urea.

12. Preservative according to one of claims 1 to 10, characterized in that it comprises

a) 80 to 98% by weight, preferably 84 to 96% by weight, more preferably 86 to 94% by weight, in particular about 95% by weight, of N,N′

methylenebis(5-methyloxazolidine),

b) 1 to 10% by weight, preferably 2 to 8% by weight, more preferably 2 to 7% by weight, in particular about 5% by weight, of urea and

c) 1 to 10% by weight, preferably 2 to 8% by weight, more preferably 3 to 7% by weight, in particular about 5% by weight, of phenoxyethanol.

15. Use of a preservative according to one of claims 1 to 12 for preserving a technical product.

16. Use according to claim 15, characterized in that the technical product is a cutting fluid, propellant, surface coating, a dispersion or a water-based paint.

13. Process for the preparation of a formal-containing preservative with reduced formaldehyde emission in which

a) at least one amine and/or alcohol is initially introduced,

b) formaldehyde is added,

c) the mixture is optionally heated to a temperature in the range from 50°

C. to 100°

C.,

d) at least one emission-reducing additive is added which is chosen from urea, urea derivatives, amino acids, guanidine and guanidine derivatives,

e) the mixture is optionally heated to a temperature in the range from 50°

C. to 100°

C. and

f) optionally odour-modifying additive is added which is chosen from alcohols, glycols and glycol ethers.

14. Process according to claim 13, characterized in that

the temperature of step c) is in the range from 60°

C. to 80°

C., in particular about 70°

C., and the temperature of step e) is in the range from 60°

C. to 80°

C., in particular about 70°

C., and additionally in step e) water is distilled off under reduced pressure.

17. Use of urea, urea derivatives, amino acids, guanidine or guanidine derivatives for reducing the formaldehyde emission of a composition which comprises a formal.