DE2103244A1 - Ultraviolet light stabilizers - Google Patents

Description

The present invention relates to ultraviolet light statoilizers and process for their preparation * The invention also relates to compositions of poly (^) - olefins, with the help of the stabilization compounds according to of the invention are stabilized.

It is known that polyethylene, polypropylene and copolymers of ethylene with higher alkenes such as propene and butene or with vinyl acetate are subject to decomposition under the influence of ultraviolet light; this decay consists in the destruction of the mechanical properties of the (Cο) ροlyme rs,

It has now been found that this decomposition of the (co) polymer, especially of the polyethylene, is reduced or avoided can be achieved by incorporating one or more compounds of the formula:

I D i

R ¹

in the (co) polymer to stabilize it, in which R is a of the groups:

- 0 D. Ij R. -C-

109832/1188

una

(III)

represent in which X is an alkyl group, an alkanoyl group or an alkoxyoarbonylmethyl group with 6 bii; 20 carbon atoms and Y represent an alkyl group having 1 to 5 carbon atoms and η is 1 or 2, and when η is 1, R ^{1 is} an unsubstituted phenyl group or a substituted phenyl group having a substituent of alkyl groups having 1 to 6 carbon atoms, Alkoxy groups having 1 to 4 carbon atoms, a hydroxyl group, a nitro group and a halogen atom and when η is 2, H ^{1 is} phenylene,

Examples of compounds according to the invention are listed below and then reference is made to the preceding numbers:

(1) 3-octyloxyphenyl benzoate

(2) 2- (4-0ctyloxyphenyl) -2- (4-salieyloyloxyphenyl) propane

(3) 2- (4-0Gtyloxyphenyl) -2- (4-benzoyloxypfaenyl) propane

(4) 2- (4-octyloxyphenyl) -2- / ¥ - (; 5-isopropylbenzoyloxy) pheny2,7-propane

(5) 2- (4-octyloxyphenyl) -2- / ² F- (4-chlorobenzoyloxy) phenyl7-propane

(6) ji-OGtyloxyphenyl-4-chlorobenzoate

(T) bis (5-octylojcypheny 1) terephthalate

(B)> - (Laury loxy e arbony liT »e thoxy) phenyl benzo at (C)) ^ -Octyloxyphenyl-2-methoxybenzoate

(10) 3-steamer oxyphenyl benzoate

(11) 5-lauryloxyphenyl alsoate

(12) 3-stearyloxyphenylbenzoafc

109832/1788

ORIGINAL INSPECTED

(13) 5-Lauroy loxyphenyl berizoate

(14) 2 - (- ^! J-Octyloxyphenyl) -2- / ⁷ F - (^ - tert-butylbenzoyloxy) phenyl7propane

(1)) 2- (4-Oet.yloxyphenyl) -2 - ^ - (4-nitrobenzoylor.y) phenyl / -

prop.m
(lo) 2-r-'H.tnyl- ^! i - ('i-octyloxyphenyl) -4- (4-benzoyloxyphenyl) -

pentane

(17 ^N bis - 'μ -jet - (4-octyloxyphenyl) isopropyl phony 1 / terephV.lmlat (Ib) ⁷ 5 - (? Te: n * yloxycarbonylinethoxy) phenyl benzoate.

The compounds according to the invention are obtained by reaction of resorcinol or a compound of the general formula:

CH.

J "V-

(IV)

in which Y has the aforementioned meaning, with an aromatic Carboxy! Acid, an aromatic carboxylic acid chloride, an aromatic dicarboxylic acid or an aromatic dicarboxylic acid chloride and subsequent conversion of the obtained connection with one or the other general Form1:

Around

-C -

R ^f

(V)

(VI)

in which n, R ^f and Y have the aforementioned meanings, in the desired ethers or esters of the formula I.

109832/1788

BATH ORIGINAL

21Q3244

The esterification can be carried out in water with the addition of the aromatic (di) carboxylsäurechlorids _i conveniently dissolved in a water-miscible solvent such as dioxane or Ä'thylenglycoldimethyläther, the diphenol in water, conveniently in the presence of a water-soluble alkaline reagent such as sodium hydroxide, potassium hydroxide, Ammonium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or a water-miscible amine. In order to increase the reaction rate, it is advantageous to add a water-miscible solvent such as acetone, dioxane, ethylene glycol dimethyl ether, dimethyl sulphoxide and / or a surface-active compound and / or a quaternary ammonium salt. When using raw materials or products that are sensitive to oxidation, the reaction can conveniently be carried out under nitrogen.

The esterification can also be carried out in an organic solvent. In this case the aromatic (di) carboxylic acid or the (di) carboxylic acid chloride reacted as such or in an organic Solvent, for example the diphenol being in the same solvent. Benzene, Chloroform, carbon tetrachloride, diethyl ether, ethylene glycol dimethyl ether, Dioxane or pyridine can be used. The reaction takes place appropriately under the influence of an alkaline one Reagent such as metallic sodium, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, pyridine or triethylamine instead. The reaction can conveniently be carried out under nitrogen.

Resorcinol, bisphenol-A, 2-Methy1-4,4-bis (4-hydroxyphenyl) pentane, benzoic acid, o-methoxybenzoic acid, p-tert-butylbenzoic acid, m-isopropylbenzoic acid, p-chlorobenzoic acid, salicylic acid, p-nitrobenzoic acid, terephthalic acid, isophthalic acid or the acid chlorides, derived from these acids are used.

109832/1788

These acid chlorides can be obtained in a known manner by reacting the corresponding acids with chlorinating agents such as POCl. ,, PCl-j, PCl ₅ or SOCl ₂ *

The second stage of the reaction, namely the conversion into the desired alkyl ester or alkyl ether is expediently obtained by reacting the monoester obtained with an alkyl halide or an aliphatic carboxylic acid or a carboxylic acid chloride in a suitable organic solvent performed.

Dioxane, ethylene glycol dimethyl ether, Diethyl ether, benzene, chloroform, carbon tetrachloride, acetone, methyl ethyl ketone, methanol or ethanol are used v / earth. The reaction is expediently under the influence of an alkaline compound such as potassium hydroxide, sodium hydroxide, Sodium carbonate, potassium carbonate, pyridine or triethylamine carried out. The reaction can, for example, with Potassium iodide to be activated.

As alkylating or acylating agents, for example, octyl bromide, lauryl bromide, stearyl bromide, lauroyl chloride, Nanoyl chloride, stearoyl chloride, chloroacetic acid laury Ie st he or stearyl chloroacetate used.

According to another feature of the invention, the Compounds of the formula I of the invention are obtained by reacting resorcinol or a compound of the formula IV with an alkyl halide, a carboxylic acid chloride or an alkyl ester of chloroacetic acid, conveniently in one suitable organic solvent, whereby a monoether or monoester of the following general formula is formed will:

f \ - OH or

(VII) (VIII)

109832/1788

in which X and Y have the aforementioned meaning. The alkylation or acylation conditions are the same, as described for the second reaction stage of the aforementioned production process.

The desired monoether can also be hydrolyzed of the ester of the formula I are obtained, advantageously under alkaline reaction conditions.

From the compounds of the formulas VII or VIII, the compounds of the formula I can be esterified with an aromatic (di) carboxylic acid or a (di) carboxylic acid chloride can be obtained in the manner described above.

The stabilizing compounds according to the invention are incorporated homogeneously into the polymer to be stabilized, expediently in the presence of other additives such as heat stabilizers, antioxidants, lubricants and pigments according to known processes, for example by mixing on the roller. V / ground advantageously in the polymer in amounts of about 0.1 to 5 wt -.% Incorporated.

The following examples and tables illustrate the invention. When referring to the characteristic in these examples and tables Infrared absorbers have been referred to, they are expressed in microns. As a measure of the Decomposition of the polymer, the carbonyl content was determined ..

Examples

1.) There were 55 g of resorcinol and 10 ml of a 25 ^ emulsifier solution (Texapon AN-4 = dispersant made of alkyl sulfate and alkylbenzenesulfonate) dissolved in one liter of water. Under nitrogen, the solution 77 β benzoyl chloride in Added for 45 minutes at room temperature, taking care it was borne in mind that the pH was kept at 9 * 6 by adding dilute caustic soda solution. After 45 minutes

109832/1788

The precipitate formed was filtered off with water
washed and from a mixture of ethanol and water im
Ratio 1: 1 recrystallized.

101 g of 3-hydroxyphenyl benzoate were obtained with
the formula:

Yield m.p.

129 to 131 C.

If resorcinol and substituted benzoyl chloride were used as the starting point, the following were obtained in an analogous manner
Compounds in which Z is the substituent on the benzoate ring:

Acid-
chloride product Z Physically.
Constants Character.
IR absorpt. p-chlorobenzene
zoyl chloride
m-isopropyl
benzoylchlo-
rid 3-hydroxyphenyl
4-chlorobenzoate
3-hydroxyphenyl
3-isopropy! Ben
zo at 4-Cl
3-CH (CH ^) ρ M.p.
JAl - 142 ° C
ng ⁰ = 1.5648 OH str. 2.88
C = O str. 5.80
OH str. 2.80
C = O str. 5.70

2.) 110 g of resorcinol were added to a solution of 1.5 g of terephthalic acid in 320 g of pyridine. 66 g of thionyl chloride were added to this reaction mixture under nitrogen at ho ° C. in the course of 1 hour. After 30 minutes, the reaction mixture was dissolved in 500 ml of concentrated hydrochloric acid
Poured in cooling to t 30 ^° C. The product obtained was filtered off, washed with water and bicarbonate solution, then dried and then from a mixture of acetone
and water recrystallized in a ratio of 1: 2.

109832/1788

There were 79.0 g of bis (3-hydroxyphenyl) terephthalate with the formula:

- ο

HO

Yield 90 %

215 to 220 C

Character IR absorption obtained.

OH str. 2.88 (C = O str. 5.75

3 ·) 68.4 g of bis-phenol A, 22.2 g of caustic soda and 10 ml of a 5% emulsifier solution (Texapon AN-4) were dissolved in 250 ml of water and 50 ml of acetone. 28.1 g of benzoyl chloride were added to this reaction mixture at 0 ° C. in the course of 1 hour. After 50 minutes, the product obtained was filtered off and recrystallized from a mixture of ethanol and water / water in a ratio of 1: 1.

55.2 g of 2- (4-hydroxyphenyl) -2- (4-benzoyloxyphenyl) propane were obtained obtained with the formula:

Yield 85 %

M.p. 151-15 ° C Character IR absorption

OH str. 2.88 (C = O str. 5.88

109832/1788

Starting from bis-phenol A and p-chlorobenzoyl chloride, 2- (4-hydroxyphenyl) -2- / i - (- chlorobenzoyloxy) phenyl7-P ^ro P ^an with the formula:

(OH str. 2.92 character. IR absorption ( _{c = 0 str>} ^ ₈₄ |

4.) 4.6 g of metallic sodium were dissolved in about 250 ml of ethanol and 45.6 g of bis-phenol A were then added to this solution. After the alcohol had been distilled off under reduced pressure, the monosodium phenoxide of bis-phenol A obtained in this way (50 g) was suspended in 250 ml of dry benzene and then J> 1 g of salicyloyl chloride in 150 ml of benzene was added. The reaction mixture was refluxed for 2 hours. After washing with water and bicarbonate solution and after distilling off the solvent, 46.5 g of 2- (4-hydroxyphenyl) -2- (4-salicyloyloxyphenyl) propane were obtained with the formula: J

/1
\ 0
ΓΛ Il
y - Kj - (J ^ V Λ CH ₅
I. 2.90 / 3.05
5.94 OH I. yield
Character 67 %
IR absorption (
( OH
C = O st.
st.

VJerin one of various bis-phenols and substitutes ierten Benzoylchloriden ran out, the following compounds of the general formula were obtained in an analogous manner:

109832/1788

- ίο -

C-O-N

21Q32U

CH ₃

C -

-OH

109832/1788

CO OO CaJ

acid
chloride Bis-phenol product Z Y ,
Physically.
Constants ^: Character.
IR absorption m-iscpropyl
benzoyl
chloride Bis-phenol A 2- (4-hydroxyphenyl) -
o- / 4 ~ - (3-isopropyl-
benzoyloxy) -phenyl / -
propane > - CH (CH,) r. CH ₅ semi-solid
product OH str. 2.85
C = O str. 5, BÖ p-chlorine
benzoyl
chloride Bis-phenol A 2- (4-hydroxyphenyl) -
2- / 4 "- (4-chloro
benzoyloxy) -phenyl / -
propane 4-Cl CH, semi-solid
product OH str. 2.92
C = O str. 5.84 p-tert.-
Butyl
benzoyl
chloride Bis-phenol A 2- (4-hydroxyphenyl) -
benzoyloxy) -phenyl7-
propane 4-C (CH ^) ₅ CH, semi-solid
product OH str. 2.91
C = O str. 5.88 p-nitro
benzoyl
chloride Bis-phenol A 2- (4-hydroxyphenyl) -
2- / 4 "- (4-nitro-
benzoyloxy) -phenyl / -
propane 4-N0 _? CH, M.p.
218-220 ° C OH str. 2.88
C = O str. 5.80 Benzoyl
chloride 2-methy1-4,4-
bis- (4-hydroxy
phenyl) pent 2-methyl-4- (4-
hydroxyphenyl) -4- (4-
benzoyloxyphenyl) -
pentane CH ₂ CH (CH ₅ ) ρ n ^ ⁰ = 1.5670 OH str. 2.90
C = O str. 5.82

5 ·) There were 22.8 g of bis-phenol A in 100 ml of ethylene glycol dimethyl ether with 2.3 g of metallic sodium for reaction and then a solution of 10.15 g of terephthaloyl chloride in 50 ml of ethylene glycol dimethyl ether was added. The reaction mixture was then heated to 85 ° C. for 6 hours. The product thus obtained was dissolved in water poured, washed with water and a bicarbonate solution and made from a mixture of acetone and chloroform in proportion 1: 1 recrystallized.

18.5 g of bis-Zi-JTcC - (^ - hydroxyphenyl) isopropylphenyl7-terephthalate were obtained obtained with the formula:

Yield 63 %

M.p. 280 to 300 ° C char. IR absorption

OH str. 2.89 (C = O str. 5.79

6.) 64.2 g of 3-hydroxyphenyl benzoate, obtained as described in Example 1, 75> 2 g of octyl bromide, 55 * 8 g of K ₂ CO, .0 aa. and 6 g of KI refluxed in 100 ml of dry acetone for 48 hours. After pouring into water, the product obtained was taken up in benzene and washed with water. After evaporation of the benzene, 97 * 5 S of the compound (1) were obtained with the formula:

1098 3 2/1788

, ^0C 8 ^H 17

Ο ¹ -

Yield 72 %

Character IR absorption C = O str. 5.78

Alkylation of the monoester obtained, as described in Examples 1 and 2, gave in an analogous manner the following compounds with the general formula:

R ^T

-C-O

109832/1788

Alkylating agents Monoester solvent base product Octyl bromide 3-hydroxyphenyl 4-chlorobenzoate acetone K ₂ CO ₃ (6) Octyl bromide Bis (. ^ - hydroxyphenyl) terephthalate acetone K ₀ CO, (7) Lauryl chloroacetate 3-hydroxyphenyl benzoate acetone K ₂ CO ₃ (8th) Lauryl bromide 3-hydroxyphenyl benzoate acetone KpCO ₃ (H) Scearyl bromide 3-hydroxyphenyl benzoate acetone K ₂ CO ^, (12) I stearyl chloroacetate 3-hydroxyphenyl benzoate acetone K ^ CO-, (Ib)

OO UO KJ

product X ^c 8 ^H l7 η R ' Physical constants Character IR absorption OO ^C 8 ^H 17 OO (6) CH ₂ COpC ₁₂ H ₂₅ 1 4-CLC ₆ H ₄ semi-solid product C = O str. 5.83 (7) ^C 12 ^H 25 2 1, ^ - C ₆ H ₄ semi-solid product C = O str. 5.79 (8th) C ₁₈ H ₃₇ 1 ^C 6 ^H 5 M.p. 34 to 35 ° C C = O str. 5.71 / 5.81 (H) ^CH ? ^C0 2 ^C 18 ^H 37 r-l ^C 6 ^H 5 M.p. 48 to 50 ° C C = O str. 5.79 (12) 1 ^C 6 ^H 5 M.p. 54 to 57 ° C C = O str. 5.79 (18) 1 C ₆ H ₅ M.p. 43 to 45 ° C C = O str. 5.72 / 5.79

.-j O CO

INJ ■ Ο-

By alicylating the monoesters obtained, as in the Examples "?, 4 and 5 described were obtained in an analogous manner Way the following compounds with the general formula:

Il

-c-c

CE ₃

.,. J VV

OX

109832/1788

Alkylation
middle Monoester Solution
middle base product Octyl bromide 2- (4-hydroxyphenyl) -2- (4-salicyloyloxyphenyl) propane acetone K ₂ CO ₅ (2) Octyl bromide 2- (4-hydroxyphenyl) -2- (4-benzoyloxyphenyl) propane Dioxane K ₂ CO ₅ O) O
CD Oatyl bromide 2- (4-hydroxyphenyl) -2- / 4 "- (3-isopropylbenzoyloxy) -
phenyI / proρan acetone K ₂ CO ₅ ■>->
NJ) Octylbrorr.id 2- (4-hydroxyphenyl) -2- / ¹ T- (4-chlorobenzoyloxy) -pheny17-
propane acetone K ₂ CO ₅ (5) -J
CO Octyl bromide 2- (4-hydroxyphenyl) -2- / 4 "- (4-tert. ButyIbenzoyloxy) -
phenyI / propane acetone K ₂ CO ₅ (14) CD Gctylbrcmid 2- (4-hydroxyphenyl) -2- / 4- (4-nitrobenzoyloxy) -pheny Lj-
propane acetone K ₂ CO ₅ (15) Octyl bromide 2-Methy1-4- (4-hydroxyphenyl) -4- (4-benzoyloxyphenyl) -
pentane acetone K ₂ CO ₅ (16) Octylbrorr.id Bis / i- »« £ - (4-hydroxyphenyl) isopropyl / phenyl7terephthalate acetone K ₂ CO ₃ (17)

product X Y η R ' Physical
Constants Characteristic
IR absorption σ
CD
OO (2) CgH ₁₇ CH ₃ 1
1 2-HO-C ₆ H ₄
^C 6 ^H 5 _n 2 ° = 1.5173
M.p. 75 to 85 ° C C = O str. 5.97
OH str. 2.95
C = O str. 5.80 ro W. 1 j— Ι, Οη-τ ) pUn. O ₆ Jl ₄ semi-solid product C = O str. 5.79 88At (5) ^c 8 ^K i7 1 4-Cl-C ₆ H ₄ n ^ ° = 1.5464 C = O str. 5.79 (14) ^C 8 ^H 17 CH ₃ 1 n ^ ° = 1.5387 C = O str. 5.80 (15) ^C 6 ^H 17 CH ₃ 1 4-O ₂ NC ₆ H ₄ n ^ ° = 1.5120 C = O str. 5.85
NO ₂ str. 7.48 (16) ^c 8 ^H l7 OH ₂ CH (CH ₃ I ₂ 1 ^C 6 ^H 5 njf = 1.5339 C = O str. 5.78 (17 ' CH ₃ 2 1,4-C ₆ H ₄ semi-solid product C = O str. 5.8l

7.) 4.28 g of 3-hydroxyphenyl benzoate were obtained according to Example 1, and 6.05 g of stearoyl chloride in 50 ml dry chloroform heated to 62 ° C for 5 hours. After this After cooling, the solution was washed with dilute caustic soda and then with water until neutral. After recrystallization from methanol, o, 2 g of the Compound (12) obtained with the formula:

Yield 85: »

Srnp 62 to 65 ° G

Character IR absorption C = O str. 5.70 / 5.80

When talking about the ^ -hydroxyphenylbenzoate and lauroyl chloride the compound (11) was obtained in an analogous manner. with the formula:

f, "'λ

/ Vc-O - / ^x ;

M.p. 39 to 41 ° C

Character IR absorption C = O str. 5.69 / 5.79

ύ.) 11.0 g of resorcinol and V), '!) g of octyl bromide were dissolved in 100 ml of boiling ethanol. A solution of 5.6 g of potassium hydroxide in 100 ml of ethanol was added to this solution. After a reflux period of 4 hours, the alcohol was distilled off and the residue was taken up in benzene

1098 ^ 2/1788

21032 * 4

and washed with water. After the solvent has been distilled off 12.2 g of 3-octyloxyphenol were obtained with the formula:

HO

Yield 55 , o

n ^ ° 1.5030

Character IR absorption OH str. 2.90 M.

4.44 g of 3-octyloxyphenol were obtained as above described, 4.25 g of 2-methoxy likewiseyl chloride and 2.37 g of pyridine Heated under reflux in 50 ml of dry benzene for 2 hours. After washing successively with dilute hydrochloric acid, Water, dilute caustic soda solution and water until neutral, the solvent was distilled off.

6.8 g of 3-octyloxyphenyl 2-methoxybenzoate were obtained with the formula:

r \ ι y

Yield £ 95

n ^ ° 1.5343

Character IR absorption C = O str. 5.77

If you started from 3-octyloxyphenol and benzoyl chloride, the compound (1) with the formula was obtained in an analogous manner:

109832/1788

ο / Λ

9 ·) 100 g of low-pressure polyethylene were with 250 mg 3-Octyloxyphenylbenzoat mixed and stored at one temperature from 120 ° C on a roller mixer to a colorless transparent one Layer worked up. This layer was on uniform thickness of 0.2 mm pressed and then 2000 hours of ultraviolet light irradiation in a xenotester subject. The carbonyl content was determined as the measure of the disintegration of the layer.

The stabilizing power of other compounds according to the invention was determined in an analogous manner. The used Compounds and the measured degrees of disintegration are as follows:

product Carbonyl content * 0.60 (D 0.14 (3) 0.30 (4) 0.28 (6) 0.36 (7) 0.24 (8th) 0.36 (H) o, o6

* calculated from the increase in the absorption of the carbonyl band in the IR spectrum.

109R32 / 1788

Claims (1)

Claims represents in which X is an alkyl group, an alkanoyl group or an alkoxycarbonylraethyl group having 6 to 20 carbon atoms, Y is an alkyl group having 1 to t> carbon atoms and η is 1 or 2, and when η is 1, R 'is an unsubstituted phenyl group or a substituted phenyl group having a substituent of alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to k carbon atoms, a hydroxy group, a nitro group and a halogen atom, and when η is 2, R 'is phenylene. 2.) 3-octyloxyphenyl benzoate. 3.) 2- (4-0ctyloxyphenyl) -2- (4-salicyloyloxyphenyl) propane. h .) 2- ( ⁱ t -0ctyloxyphenyl) -2- (4-benzoyloxyphenyl) propane. 2- (4-0ctyloxyphenyl) -2-pheny_L7propane. 6.) 2- (4 -Ofityloxypheny 1) -2-f% - ( ^j l -chlorobenzoyloxy) pheny Yj ^pPoparr · 10 9 8 3 7/1788 7 ·) 3-Octyloxyphenyl-4-chlorobenzoate. c. ) Bis (jj-octyloxyphenyl) terephthalate. 9 ·) .'- (Lauryloxycarbonylmethoxy) phenylbenzoate 10.) ^ -Octyloxypheriyl-P-methoxybenzoate. 11.) J-stearoyloxyphenyl benzoate. 12. ) 3-Lauryloxyphenylbenzoate. ^ k 1J5. ) 3-stearyloxyphenyl benzoate. You ) ^ -Lauroyloxypherjyibenzoate. 1?. ) 2 - (^ - 0ctyloxyphenyl) -2 - / ^ - (^ - tert.butylbenzoyloxy) -pheny l ^ prο ρan. l6.) 2- (4-0ctyloxyphenyl) -2- / ^I r - (^ - nitrobenzoyLoxy) pheny_l _: 7-propane. 17.) 2-Methyl - ^ - (^ - octyloxyphenyl) -4 - (- 4-benzoy Loxy phenyl) pe η Um. lo.) 3IsZh-. oC - (4-octyloxyphenyl) isopropyl | phenj ^! L / 'tereptilh ;; L ^r it. 19.) 5- (Gteary Loxycarbonylinethoxy) pheriylber.zo <': t. 20.) Process for the preparation of a compound of the more general: Formula I according to claim 1, characterized in that daiu; one resorcinol or a compound of the general formula: in which Y has the meaning given in claim 1., with an aromatic mono- or dicarboxylic acid or an aromatic mono- or dicarboxylic acid chloride for the reaction brings and the connections obtained with tier ·, -! LLgo-1098 ^ 2 / 1788 BATH ORIGINAL my formula: / Λ- ο - C - HO Jn CH R ¹ Jn in which Y, R ¹ and η have the meaning given in claim 1, converted into an alkyl ether or the ester of an aliphatic carboxylic acid. 21.) Method according to claim 20, characterized in that the esterification is carried out in 'water. 22.) Process according to claim 21, characterized in that the esterification is carried out in the presence of a water-soluble alkaline compound. 23 ·) Process according to claims 20 to 22, characterized in that the aromatic mono- or dicarboxylic acid chloride is dissolved in a water-miscible organic solvent. 24.) Process according to claim 20 to 23, characterized in that the esterification is carried out in the presence of a water-miscible solvent, a surface-active substance or a quaternary ammonium salt. 109832/1 788 21032Λ4 25 ·) Process according to claim 20, characterized in that the esterification or the A'therification is carried out in an organic solvent in the presence of an alkaline compound. 26.) The method according to claim 25, characterized in that the reaction is carried out in the presence of potassium iodide. 27 ·) Process for the preparation of a compound of the general formula I according to claim 1, characterized in that resorcinol or a compound of the general formula: in which Y has the meaning given in claim 1, with an alkyl halide, a carboxylic acid chloride or others an alkyl ester of chloroacetic acid reacts in an organic solvent and the compounds obtained with the general formula: • CH ^ ? V OH or XO .J \ - CS V- OH XO ^Y in which X has the meaning given in claim 1, with an aromatic mono- or dicarboxylic acid or an aromatic mono- or dicarboxylic acid chloride for Reaction brings. The method of claim 20 or 27, moves dadu rch gekennze Leh net that is substantially as described in Examples 1 to ο. 1 788 29.) Compound of the formula I according to claim 1, characterized in that it is prepared according to the method according to any one of claims 20 to 28. 1 09 * 37/1 788