DE1520688B2 - PROCESS FOR THE PRODUCTION OF HYDROXYL-CONTAINING COPOLYMERISATES - Google Patents

Description

3 4

are styrene, α-methylstyrene, vinyl toluene, vinyl acetate, temperature gradually brought to 160 ° C, whereby Ester of acrylic and methacrylic acid and nitrogen, the solvent is distilled off and in the template containing derivatives of the latter such as acrylic can collect. The temperature is geamid to 160 ° C. hold until the acid number falls to a minimum of 21

A specific embodiment of the invention is 5 drops. The filling is then cooled slightly and characterized in that the solvent which has been distilled off is added again as the glycidyl ester Glycidyl Benzoate or Sunflower Fatty Acids-Gly- (if it should prove necessary you can cidylester is used. other solvents added at this point

A special use of the process products will be). The final solution possesses after having with is the production of oven-hardening lacquers, whereby the io xylene to a content of 50% non-volatile Copolymers according to the invention is adjusted with etherified constituents, a viscosity according to Amino and / or epoxy resins are mixed. Gardner - Holdt from V — W and an acid

Another special use of the procedure number of 13.

products is the manufacture of paints according to example 2

Two-component system, using the copoly- 15

merisat with an isocyanate prepolymer or the following mixture consisting of

a polyisocyanate.

Another special use of the process- Commercially available xylene 462 g

products is the manufacture of air-drying n-butanol 154 g

Lacquers, where a Co- .20 lauryl mercaptan produced according to the invention is 4 g

polymer mixed with a dry catalyst

will. is heated to 120 ° C. with stirring. The following

An additional special use of the mixture is then added in portions, the preparation of an oven-hardening period of 2 hours is distributed over a driving product, with lacquers, whereby the Cppolymerisat is maintained with a temperature of 120 ° C:
Amino resin mixed.

In the following examples, the glycidyl styrene ..: ...... 200 g

esters of α-alkylalkane monocarboxylic acids and / or butyl acrylate 100 g

«,« - dialkylalkane monocarboxylic acids used (be methacrylic acid 100 g

marked as glycidyl ester E). These acids make 30 di-tert-butyl peroxide 12 g

mainly a mixture of C ₉ -, C ₁₀ -, and C _u t

Monocarboxylic acids are obtained from a mixture of Afterwards the mixture is further heated to 120.degree

C ₈ , C ₉ and C ₁₀ olefins are held with carbon oxide and water for an additional 2 hours. The salary were made. The acids are completely saturated, the solution should be of non-volatile constituents and should be very strong at the α-carbon atom, now 33 to 34 ° / ₀ , and is substituted by adding. Acids with two hydrogen atoms in 4 g of di-tert-butyl peroxide and 2 hours of heating ”carbon atom are not present, and only at 120 ° C. to the theoretical value of 39 ° / ₀ er-6 to 7% of these acids contain a hydrogen atom increases.

on the «carbon atom. In addition, after adding 216 g of glycidyl ester E becomes cyclical

Material before (Deutsche Farben-Zeitschrift, Heft 10, 40 the temperature gradually increased to 160 ° C until the 16th year, p. 435). Acid number to a minimum of about 24 for that

this example drops. The filling is then

Example 1 cooled slightly and the solvent that was distilled off

added back to content. This final solution

The following mixture, consisting of 45, has 50% non-volatiles, the viscosity

according to Gardner-Holdt is V to W and

Commercially available xylene 231 g has an acid number of 14.

n-butanol 77 g It is surprising that in the case of the invention

Lauryl mercaptan, 2 g process the implementation of the glycidyl ester already

50 at temperatures between 100 to 160 ° C in the absence

is heated to 120 ° C. with stirring. Then one catalytic converter is possible and that one after the other in portions, over a period of settling in situ during or after Copolymerisa-2 Hours distributed, at a temperature of 120 ° C, tion can take place.

The following components have been added: To clarify this, the following statements are made

55 similar tests were carried out.

Styrene 110 g _ _r,. ,,.

Butyl acrylate, 40 g comparative experiment a)

Methacrylic acid, 50 g Example 2 was repeated with the exception

Di-tert-butyl peroxide 6 g development that 72 g of phenylglycidyl ether instead of 125 g

60 glycidyl ester E on an exact equivalent epoxy

The mixture is then used for an additional 2 hours on the basis. While maintaining the temperature maintained at a temperature of 120 ° C. The non- this approach to 160 ° C was only noticeable by the acid number volatile content of this solution should at this time - the value 55, instead of the acid number 11, which is im point 33 to 34% and is obtained by a further parallel experiment according to Example 2. Addition of 2g di-tert-butyl peroxide and heating 65 ',,,.,,, X

at 120 ° C for a period of 2 hours on the comparative test b)

theoretical value of 39%. In a further comparison according to Example 2

108 g of glycidyl ester E are added and it works, but the equivalent amount (55 g)

Ayl glycidyl ether is used in place of the 125 g glycidyl ester E. While maintaining the temperature at 160 ° C this approach, the acid number fell to the value 75 instead of falling to the acid number 11, as in the Comparative experiment according to the invention happened.

Example 3 The following mixture consisting of

IO

Commercial xylene 257 g

n-butanol 86 g

Lauryl mercaptan 2 g

is heated to 120 ° C. with stirring. The five mixtures listed below [a) to e)] are then added in portions within half an hour at 120 ° C:

a) styrene 20 g

Ethyl acrylate 10 g

Acrylic acid 1.5 g

Di-tert-butyl peroxide 1.2 g

then

b) styrene 20 g

Ethyl acrylate 10 g

Acrylic acid 3 g

Di-tert-butyl peroxide 1.2 g

30th

35

40

45

thereafter .

c) styrene 20 g

Ethyl acrylate 10 g

Acrylic acid 6 g

Di-tert-butyl peroxide 1.2 g

further

d) styrene 20 g

Ethyl acrylate 10 g

Acrylic acid 12 g

Di-tert-butyl peroxide 1.2 g

further

e) styrene 20 g

Ethyl acrylate 10 g

Acrylic acid 27.5 g

Di-tert-butyl peroxide 1.2 g

The mixture is then kept at a temperature of 120 ° C. for a further 2 hours. There are a further 2 g of di-tert-butyl peroxide was added and heating at 12O ⁰ C for a period of a further 2 hours continued. Another 1 g of di-tert-butyl peroxide is added and heating continued for a further 2 hours, giving the theoretical non-volatile content of 36 to 37% constituents. 163 g of glycidyl ester E are then added and the temperature is gradually increased to 160 ° C., as a result of which the solvent is distilled off and can collect in the receiver. The temperature of 160 ° C is maintained until the acid number has dropped to the minimum of about 11. The filling is then cooled slightly and the solvent which has distilled off is returned to the contents. The final solution now has non-volatile components of 50%> the Gardner-Holdt viscosity is Q to R and the acid number is 7.

Example 4
The following mixture consisting of

Commercial xylene 207 g

n-butanol 69 g

Lauryl mercaptan 2 g

is heated with stirring to 120 ° C and the following mixture in succession within 2 hours - at 12O ⁰ C - added:

Styrene 100 g

Butyl acrylate 50 g

Methacrylic acid 50 g

Di-tert-butyl peroxide 6 g

The mixture is then kept at a temperature of 120 ° C. for a further 2 hours held. The non-volatile component of the solution should now be 34 to 36% and will be through further addition of 2 g of di-tert-butyl peroxide and a further 2 hours of heating at 120 ° C. on the theoretical value of 42% brought. After adding 76 g of glycidyl benzoate, the temperature gradually increases increased to 160 ° C, whereby the solvent is distilled off and collect in the template can. This process continues until the acid number drops to the minimum of about 28.

The mass is then cooled and reduced to a non-volatile content of 50% with a 3: 1 xylene-butanol mixture. The final solution thus obtained has a Gardner-Holdt viscosity of Z ₃ and an acid number of 16.5.

Example 5
The following mixture consisting of

n-butanol 25 g

Commercial xylene 50 g

Methyl isoamyl ketone 25 g

Methacrylamide 5 g

Styrene 30 g

Butyl methacrylate 20 g

Ethyl acrylate 30 g

Methacrylic acid 15 g

Di-cumyl peroxide Ig

is placed in a flask equipped with a reflux condenser and stirrer, gradually heated to 120.degree and held at this temperature for 2 hours. After adding another 1 g of di-cumyl peroxide the temperature is kept at the same level for a further 2 hours, around the theoretical to obtain non-volatile content of 50%. 32 g of glycidyl ester E are added and the temperature increased to 160 ° C, whereby the solvent can distill off into the template. the The temperature is maintained at 160 ° C until the acid number has reached a minimum of 8.5. The material is then cooled and the distilled solvent returned to the material. The on this The final solution obtained in this way gives after adjustment with a 2: 1: 1-xylene: n-butanol: methyl isoamyl ketone mixture on non-volatile components of

7 8

50% a viscosity from Z ₁ to Z ₂ , and the acid number viscosity according to Gardner-Holdt of 7, and is 4.9. the acid number is 7.6.

Examples r> · · ι ο

Example ^

The following mixture consisting of 5 _Da s following mixture consisting of

Ethyl glycol acetate 84 g Commercial xylene 257 g

n-butyl glycol acetate 28 g n-butanol 86 g

Methyl isoamyl ketone 28 g lauryl mercaptan 2 g

ίο ^;

and 40 g of glycidyl ester E are heated to 120 ° C. with stirring. Then become

130 ° C heated and the following mixture por- the five mixtures listed below [a) to

tionwise over a period of 2 hours - in e)] in portions within a period of each

Maintaining the temperature of 130 ° C - for an additional half an hour - while maintaining the temperature

given: 15 temperature of 120 ⁰ C - added:

Ethyl acrylate 52 ga) styrene _r .................... 20 g

Methyl methacrylate 30 g, ethyl acrylate 10 g

Methacrylic acid 18 g 'acrylic acid ...... ,, _; ........... _; ..... x 1, Sg;

Di-cumyl peroxide 2 g _ao pi-tert-butyl peroxide., .....,. _{; r} , .. ■ 1.2 g _;

then
The temperature then increases for a further 2 hours

kept at 130 ° C. The non-volatile constituents b) styrene ·· ■ ··· ..., ... 2Og

become ethyl acrylate by adding 1 g of di-cumyl peroxide 10 g

^{and heating for 2} hours at 130 ° C. to the theoretical acrylic acid 3 g

see value brought by 50%. The temperature becomes di-tert-butyl peroxide 1.2 g

then increased to 150 ° C until the acid number is constant

is at least 11. The solution obtained has a further ^;

Viscosity from H to I and an acid number of 10.4.

The products of these examples can include 30 c) styrene; ................ 20 g

for the production of lacquers use, ethyl acrylate 10 g

in connection with etherified amino resins acrylic acid 6 g

and / or epoxy resins, at curing temperatures di-tert-butyl peroxide 1.2 g

between 120 to 180 ⁰ C.

_. . , _ 35 further

Example 7

The following mixture consisting of d) styrene 20 g

Ethyl acrylate 10 g

; Commercially available xylene 244 g acrylic acid 12 g

n-butanol 81 g ₄₀ di-tert-butyl peroxide .. '. 1.2 g

Lauryl mercaptan 2 g

then

is heated to 120 ^° C. with stirring, and the mixture listed below is added in portions, e) styrene ........................... 20 g

over a period of 2 hours, maintaining 45 ethyl acrylate 10 g

tion of the temperature of 120 ⁰ C, added: acrylic acid 27.5 g

Di-tert-butyl peroxide 1.2 g

Styrene 100 g

Butyl acrylate 50 g Thereafter, the mixture is further to 120 ° C for the

Methacrylic acid 50 g 50 held for 2 hours. After another

Di-tert-butyl peroxide 6 g of addition of 2 g of di-tert-butyl peroxide, the heating is continued at 120 ^° C. for a further 2 hours.

The mixture is left on the temperature for a further 2 hours. Then 1 g of di-tert-butyl peroxide is added.

temperature of 120 ° C kept. The non-volatile given and heated for a further 2 hours at 120 ° C,

Part of this solution should now be 32 to 33 ° / ₀ 55, whereby the theoretical content of non-volatile

and is achieved by adding 2 g of di-tert components from 36 to 37%.

Butyl peroxide and additional 4 hours of heating. After adding 163 g of glycidyl ester E, becomes

at 12O ⁰ C to the theoretical value of 38%, the overall temperature gradually to 160 ° C increased, whereby

brings. distill off the solvent and place in the template

Then 125 g of glycidyl ester E are added 60 can be collected. The temperature of 16O ⁰ C

and the temperature is increased to 160 ° C, thereby maintaining that until the acid number is at a minimum

Distilling off the solvent in the template has reached 11. The product then becomes light

becomes possible. The temperature is ^{cooled to 160 0} C and with a solvent mixture of

hold until the acid number is at least 11. The 2: 1 xylene to ethyl glycol acetate on a non-volatile

Material is cooled down and reduced by 50% by adding 65% of the component. That way

Xylene on a 50%, non-volatile component obtained solution, which is practically butanol-free, has

set. The solution obtained in this way, which has a Gardner-Holdt viscosity of

is now almost free of butanol, now has a U to V and an acid number of 7.3. . · ^;

9 10

Example 9 Example 11

The following mixture consisting of The following mixture consisting of

Commercially available xylene 207 g ₅ Commercially available xylene 600 g

n-butanol 69 g n-butanol 300 g

Lauryl mercaptan 2 g Lauryl mercaptan 6 g

is heated to 120 ^° C. with stirring and the subsequent and the following reaction mixture, consisting of:

standing mixture in portions over to

a period of 2 hours - while maintaining styrene 300 g

the temperature of 12O ⁰ C - added: butyl acrylate 120 g

Methacrylic acid 180 g

Styrene 100 g di-tert-butyl peroxide 80 g

Butyl acrylate 50 g 15

Methacrylic acid 50 g are treated according to Example 10 to give a

Di-tert-butyl peroxide 6 g content of theoretical non-volatile components

of 40%.

The mixture is then added for a further 2 hours to 504 g of glycidyl ester E and the

maintained at a temperature of 120 ° C. The content of 20 temperature gradually increased to 160 ⁰ C to the

non-volatile components of this solution should now- distill off and collect the solvent in

more than 34 to 36%. To enable by adding the template again. The temperature of ^

add 2 g of di-tert-butyl peroxide and 160 ⁰ C for 2 hours is maintained until the acid number is minimally C.

Heating at 120 ^° C., the non-volatile content is 4.0. The material is then easily removed

Cools and components on the theoretical value of 42% 25 99.5 ^o / pc alcohol pure ethyl acetate to

brought. a content of 50% non-volatile components

76 g of glycidyl benzoate are then added parts lowered. The solution obtained in this way

and the temperature gradually raised to 160 ⁰ C, has a viscosity according to Gardner -Holdt

whereby the solvent is distilled off in the template from R to S and an acid number of 2.1.

can ren. This process continues as long as 3 °

until the acid number falls to the minimum of about 28. .

sinks. The product is cooled slightly and transferred to an example 12

Content of 50% nonvolatile component einge- D _as following mixture consisting of 99.5% by weight pure provides the ethyl acetate by addition.

The final solution obtained in this way, which is practically butanol-free, 35 commercially available xylene 1000 g

has a Gardner-Holdt viscosity of X and n-butanol 500 g

an acid number of 16.3. Lauryl mercaptan 10 g

and the following reaction mixture consisting of: Example 10 ₄₀

The following mixture, consisting of Bu ^ araylat ......'.'..... .. ........ 100 g

Commercial xylene 480 g of methyl acrylic acid. 400 g

n-butanol 120 g di-tert-butyl peroxide 30 g (

Lauryl mercaptan 6g ⁴⁵ -ο η · · 1 11 u 1st jnj

are treated exactly as in Example 11 to the

and to obtain the following reaction mixture consisting of: theoretical content of 40% non-volatile components. g _t j 3QQ g 1120 g glycidyl ester E are added and

Butyl acrylate 180 g ⁵ ° <* ' ^e temperature gradually increased to 160 ⁰ C to

Methyl acrylic acid "120 g of ^the distillation of the solvent and the Sam-

Di-tert-butyl peroxide '.'. '.'. '.'. '.'. '.'. '.'. Y. 18 g ^meln ™ J ~ X ⁰ ?! ⁸ ^ ^e ! ^mö ^? ^h ^ ? ^the temperature

160 C is maintained until the acid number is minimal 6.5 is. The material is cooled slightly

are treated according to Example 7 in order to arrive at the 55% and 99.5% pure ethyl acetate with a theoretical non-volatile ^{content of 50%, non-volatile content of 50%.} lowered. The solution obtained has a viscosity

33 g of glycidyl ester E are then added from Q to R and an acid number of 3.6. and the temperature is gradually increased to 160 ^° C., as a result of which the solvent can distill off and collect in the template. The temperature is set to ^. , ■ ^, ·,,,, held 160 ° C until the average acid number in the ^Da f ^fol S ^end mixture, consisting of this case, drops to about 8. Ethyl glycol acetate 84 g

The material is cooled slightly and 28 g with 99.5% n-butyl glycol acetate

pure ethyl acetate to a content of 50% non-55 methyl isoamyl ketone 28 g

volatile components set. The on this

The solution obtained in this way has a viscosity of J + and 40 g of glycidyl ester E is increased with stirring

and an average acid number of 5.2. 130 ⁰ C heated and the following mixture por-

11 12

tion-wise within 2 hours - set under parts. This solution has a viscosity preserving its temperature of 130 ⁰ C - hinzu- from I to J, an acid number of 2.8 and is arbitrarily given: dilutable with commercially available xylene.

Methyl methacrylate 30 g ₅ B eis ρ ie 1 15

Ethyl acrylate 52 g

Methyl acrylic acid 18 g The following mixture consisting of

Di-cumyl peroxide 2 g

Commercial xylene 112 g

The mixture is then used for the duration of io n-butanol 38 g

a further 2 hours at the temperature of 130 ⁰ C lauryl mercaptan Ig

held. By adding 1 g of di-cumyl peroxide and heating at 13O ⁰ C for a further 2 hours is heated with stirring to 120 ° C - under Zuwird the content of non-volatile components to circuit of inert gas and listed below the theoretical value of 50 ° / ₀ elevated. The tem- 15 mixture portionwise over the course of 2 hours, temperature is increased to 150 ⁰ C and this temperature - at the same temperature (12O ⁰ C) - added: maintained until the acid number of constant minimal 11

amounts to. The solution obtained in this way has ethyl acrylate 10 g

a viscosity from H to I and an average vinyl toluene 60 g

Acid number of 10.4. 20 methacrylic acid 30 g

The pro-di-tert-butyl peroxide obtained according to Examples 7 to 13 3 g

products that are essentially free of hydroxyl groups

containing solvents can be used

bond with isocyanates as a basis for two-component temperature of 120 ⁰ C kept. The addition nenten hardener systems are used, which cure once 25 of 1 g of di-tert-butyl peroxide and heating at 120 ⁰ C at room temperature and for the duration of a further 2 hours increases the content of other than oven-curing paints to the desired non-volatile Pass ingredients on the theoretical coatings. Value of 40 ° / ₀ .

89 g glycidyl ester of sunflower fatty acids

Example 14 3 ° are added and the temperature gradually

increased to 160 ⁰ C, whereby the solvent from the following mixture, consisting of distill and can collect in the template.

The temperature of 160 ⁰ C is maintained until

Commercially available xylene 112 g has a minimum acid number - in this case about

n-butanol has reached 38 g 35 19 -.

Lauryl-Mercaptan Ig Tj _as material is cooled and divided into two portions

divided. The first portion is based on white spirit

is heated to 120 ^° C. with stirring, a content of non-volatile constituents of inert gas is added, and then the following mixture is reduced by 50%. The solution obtained has a Visportionsweise within 2 hours - under accession viscosity of from 40 Z ₄ to Z _5, an acid number of 12.2 and preserving its temperature of 12O ⁰ C - is hinzuge- continuously diluted with white spirit. The second portion is made with commercially available xylene

to a content of 50% non-volatile components

Butyl acrylate divide 25 g lowered. The solution has a viscosity of

Vinyltoluene 50 g 45 Zj, an acid number of 11.8 and is continuous

Methacrylic acid 25 g soluble in commercial xylene. These products

Di-tert-butyl peroxide 3 g can be used for the

Manufacture of air-hardening and oven-hardening paints,

Thereafter, the mixture an additional 2 hours at appropriate with the addition of Trockenkataly-12O ⁰ C is maintained. The addition of Ig di-tert-50 or they can be used in conjunction with amino-butyl peroxide while maintaining the temperature of resins for oven-hardening paints. 120 ⁰ C over a further 2 hours result in theoretic. .

table content of non-volatile components of comparison tests

40%. To ensure the resistance of paint films to 1%

107 g glycidyl ester of sunflower fatty acids 55 sodium hydroxide solution at 20 ° C, the following were added and the temperature was gradually carried out on comparative tests and increased from the obtained -160 ° C, whereby the solvent distilled solutions in the same layer thicknesses and spreads can collect in the template. The temperature is made on steel sheets. After 30 minutes Einperatur is maintained at 160 ⁰ C, until an acid number burning time at 160 ⁰ C and cooling were achieved by this is a minimum of about. 6 The product is used 60 coats of the caustic soda and the film is cooled and divided into two parts. The first amount of quality, judged after a longer exposure time, is based on a content of 50% non-volatile 1. Example 1 of the invention was repeated.

Components set with white spirit. This solution works and coatings from the solution obtained have a viscosity according to Gardner-Holdt made on steel sheets. The stoved films from R to S, an acid number of 2.7 and any 65, showed after 50 hours of exposure to 1% thinnable with white spirit. Sodium hydroxide solution at 20 ⁰ C and had no attack

The other half becomes shiny with standard xylene,
to a content of 50% non-volatile constituents 2. Example 2 of the invention was repeated

works and made coatings on steel sheets from the solution obtained. The films baked at 160 ^° C. also showed no attack after 50 hours' exposure to sodium hydroxide solution and remained bright.
3. Example 1 of the British patent

773 206 was reworked and, as described there, coatings were made on steel sheets, which are then also ^{baked at 160 °} C. for 30 minutes. After lstündiger exposure to l ° / _o sodium hydroxide solution at 20 ⁰ C, the films were hazy appearance and had started white.

Claims (3)

1 2 development of hydroxyl groups in situ during and after claims: the copolymerization reaction and without the need to use any catalyst, 1. Process for the preparation of in organic apart from one of the conventional polymerisation solvents soluble hydroxyl-containing 5 ion catalysts available. this Copolymers by reaction of copoly- is important in practice, since the presence of merisates that are produced by polymerisation of <%, /? - un- catalysts in paints and other coatings that saturated carboxylic acids can be prepared with one or more of copolymeric products Vinyl compounds can have a detrimental effect at elevated temperature. Solvents have been prepared with epoxy ίο The invention is a process for group-containing compounds without esterification production of soluble in organic solvents with heating to 160 ⁰ C, thereby borrowed hydroxyl-containing copolymers characterized in that as epoxy-reaction of copolymers which a glycidyl ester of the generalization of α, / 3-unsaturated carboxylic acids with one of my formula * 5 or other vinyl compounds at elevated temperatures by means of a polymer-containing compound temperature have been produced in solvents, R - C - O - CH ₂ - CH - CH ₂ with compounds containing epoxy groups without Il ^ Vi ^ esterification catalyst with heating to 160 ⁰ C, there- O characterized in that as epoxy groups 20 compound is a glycidyl ester of the general formula in which R is aliphatic or aromatic Substituents means that one or more τ> rr, ru m rti may contain athylenically unsaturated bonds, μ \ / is used, the glycidyl !! O ester already during the manufacture of the copoly- 25
merisate is added. 2. The method according to claim 1, characterized in which R denotes an aliphatic or aromatic sub-character, that the glycidyl ester means glycidyl substituents which are one or more ethylenic benzoate or sunflower fatty acids-glycidyl-unsaturated bonds can be used ester is used. 30 is, where appropriate the glycidyl ester already 3. Use of the according to claims 1 and 2 added during the preparation of the copolymers obtained products for the manufacture air-will. drying or oven-hardening paints. In the method of the invention there is therefore no aqueous solvent system before, and it is also in the absence of an esterifiable catalyst lysators worked. The reaction is brought about by increasing the temperature while removing the solvent - only There are many manufacturing processes for hydroxyl - if necessary - by distillation, such as it group-containing copolymers known. 40 is shown in the following examples. The Rea- In British patent specification 773 206 the tion is fully carried out when the acid conversion of copolymers of one or more content has reached a minimum, and proceeds as several α, / 3-unsaturated carboxylic acids and with follows:
one or more vinyl monomers with triazines containing epoxy groups without esterification 45 ■ COOH + CH ₂ —CH — CH ₂ —O —CR—> catalysts with heating to 160 ⁰ C already work \ / || wrote. O q U.S. Patent 2,607,761 is a
Process known in which a styrene-maleic acid O anhydride copolymer in aqueous alkaline solution 50 || with alkylene oxides or arylalkylene oxides or C - O - CH ₂ -CH - CH ₂ -OCR Epichlorohydrin is implemented. For this implementation | || is an aqueous medium with strong alkali as Kata-OH O lysator required. U.S. Patent 3,023,178 describes the 55 _o CH OH Implementation of epoxidized esters of unsaturated u ι ² Vegetable oleic acids with carboxyl groups containing ^ _ ' _{ΓΗ n r} -a Connections to insoluble, infusible, flexible LU-LH-LH ₂ - U - L - K non-sticky and tack-free films by using a physical » Mixture of the starting components applied and 60 O is burned in. The invention is, however, a These implementations can also be used as one-step Process for the production of copolymers which are carried out in reaction. In examples 6 organic solvents are soluble and one and 13 this one-step implementation is illustrated, have a defined composition before coatings are examples of, - unsaturated carboxylic acids made from it and baked in. Acrylic acid, methacrylic acid, maleic acid and fumaric acid The object of the invention is to acidic hydroxyl groups and their monoesters.
containing vinyl copolymers by the production examples of suitable further vinyl compounds