DE2032547A1 - Production of polyisocyanates containing urea groups and their use in cellular and multicellular polyurethane plastics - Google Patents

Description

FARBENFABRIKEN BAYER AG 2032547

LEVERKUSEN-B * yerwerk Patent department Wr / Τθ

June 30, 1970

Production of polyisocyanates containing urea groups and their use in cellular and non-cellular polyurethane plastics ___

Cellular and non-cellular plastics containing urethane groups, such as are obtained by reacting polyols with polyisocyanates are widely used, e.g., in the field insulation, for the production of structural elements or for Upholstery purposes.

It is known that the physical properties of many Polyurethane plastics can be favorably influenced by the incorporation of urea groups.

These urea groupings are used in the case of foams mostly created by adding water to the foam formulation. The isocyanate hydrolysis achieved in this way results in 1 mol of water 1 mole of gaseous carbon dioxide is split off. This method can from Naöhteil where the resulting polyurethane foam is used for insulation purposes. So owns a Carbon dioxide driven rigid foam only 50 - 70 ^ the heat insulating effect of foams, whose cells with gaseous organic halogen compounds such as monofluorotrichlorourethane are filled. In the case of non-cellular polyurethane plastics one usually proceeds in such a way that the polyol is proportionately Di- or polyamines are added and the urethane polyaddition coupled with the reaction of amines with isocyanates to form ureas, or an NCO prepolymer of diols and diisocyanates cross-linked with amines. Here the content of

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Polyamine in the formulation due to the intrinsic activity of the amines limited to isocyanates.

Both ways could be avoided if those isocyanates which already contain urea groups are used for the isocyanate polyaddition. This process has hitherto failed because both the ureas obtained from water and diisocyanates and those obtained from the common primary di- and polyamines with diisocyanates are insoluble in the excess monomer isocyanate and the processing of suspensions in conventional polyurethane technology is difficult prepares. (When water is reacted with 2,4- toluene diisocyanate according to the teaching of US Pat. No. 2,757,185 , a urea adduct is obtained that immediately precipitates from the excess monomer diisocyanate at room temperature

Surprisingly, it has now been found that soluble adducts of diisocyanates with di- or polyamines can be obtained in the excess Μοηοπ> * "- α if the isocyanates are reacted with special amines. According to the invention, special amines are aromatic, araliphatic, aliphatic and cycloaliphatic only di- or polyamines containing secondary amino groups are used.

The present invention thus provides a process for the preparation of liquid di- and polyisocyanates containing urea groups from amines and polyisocyanates, characterized in that polyisocyanates at -20 to + 80 with polyamines having only secondary amino groups in the HCO / NH ratio of 2: 1 to 100: 1 can be implemented.

Here, urea diisocyanates of the following general structure are obtained from bis-secondary diamines and diisocyanates:

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R _χ / R

N-R N

II
O = CC = O

OCN-R'-NH HN-R'-NCO

where R denotes the bivalent heat on which the diamine is based, R ¹ denotes the bivalent radical on which the diisocyanate is based and B "denotes an all or aryl radical.

When the polyisocyanates are reacted with secondary amines of higher functionality, urea polyisocyanates of higher functionality can be obtained.

To prepare the polyisocyanates containing urea groups, the amines used as starting materials are used in the process according to the invention in a quantitative ratio which corresponds to an NCO / NH ratio of 2: 1 to 100: 1, preferably 2.5: 1 to 20: 1 In the preparation process according to the invention, it is advantageous, particularly in the absence of inert solvents, to add the amine to the isocyanate at a temperature which is above the melting point of the amine used. In addition, it must be ensured that the upper temperature limit of 80 ° C is not exceeded. Bas means that the process according to the invention is ^{carried out at temperatures from -20 to 4BO 0} O, preferably from +20 to 70.degree.

In general, in the process according to the invention, solutions of the polyisocyanates containing urea groups are obtained in the polyisocyanate free from urea groups used as the starting material. In addition, the reaction can also be carried out in inert solvents such as methylene chloride, chloro

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form, carbon tetrachloride, benzene, toluene. A preferred solvent is monofluorotrichloromethane, the when the polyisocyanate is later foamed as a blowing agent can serve. In cases where diisocyanates with high vapor pressure after the claimed process in physiological If harmless urea adducts are to be converted, the excess monomer diisocyanate can also be transferred through Distillation on the thin film evaporator can be removed.

The secondary aromatic polyamines used in the process according to the invention are preferably diamines, such as:

N, IT-dimethyl-2,4-tolylenediamine, N, Ν'-dimethyl-2,6-tolylenediamine, N, N'-diethyl-2,4-tolylenediamine, NjN'-dipropyl-e, ^ - tolylenediamine, NjN '-Diisopropyl ^^ - tolylenediamine, N, N'-diisopropyl-2,6-tolylenediamine, N, N'-dubutyl-2,4-tolylenediamine, N ^' - dieyclohexyl ^^ - tolylenediamine, Ν, .Ν'- Dimethyl-4,4'-diaminodiphenylmethane, N, N'-Dläthyl-4; 4 ⁱ -diaminodipheny1-methane, N, N * -dipropyl-4,4 * -diaminodiphenylmethane, Ν, Ν'-diisopropyl-4,4 * -diaminodiphenylmethane, N, N * -dimethyl-p-phenylenediamine, Ν, Ν'-diisopropyl-p-phenylenediamine, NjN'-diisopropyl-4,4'-diaminodiphenyl ether, N, N'-dicyclohexyl-4,4 * -diaminodiphenyl ether , N, N * -diisopropyl ^ e-diamino-j ^ S-dläthyltoluene, NiN'-diisopropyl ^^ - diamino - ^^ - diethyl-toluene, N, N'-dicyclohexyl-m-phenylenedlamine, NiN'-dicyclohexyl- 1-4-diaminonaphthalene, N, N'-diisopropyl-4,4'-diaminodiphenyl-dimethyl methane, N, N * -diisopropyl-4,4'-diaminodiphenyl-dicyclohexyl methane.

As secondary aliphatic, cycloaliphatic or araliphatic polyamines, diamines are preferably used in the process according to the invention, such as, for example:

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Ν, Ν'-dimethylethylenediamine, Ν, Ν'-diisopropylethylenediamine, N, N * -diisopropylpropylenediamine, N ^ N'-diisopropyl-l ^ -diaminobutane, NjN'HDicyclohexylhexamethylenediamine, N, N * -diisopropylhexamethylenediamine -Diisobutylhexainethylendiamin, N, N'-diisopropyl-diaminomethyl-cyelobutan, N, N ^f -Diisopropyltrimethylhexamethylendiamin, NiN'-diisopropyl - ^^ - diaminodicyclohexyl inethan, NjN'-diisopropyl-m- or p-xylylenediamine, N, N ^r - Diisopropylisophoronediamine, ", H'-dicyclohexylisophorone- 'diamine.

Polyamines containing only secondary amino groups with tri- and higher functionalities can likewise be used in the process according to the invention. Examples are: 4,4 », 4" -Tri- (methylamino) -triphenylmethane, 4,4 ', 4 ^M -Tri- (methylamino) -tricyelohexylpe than, N, H "-Dime thy1-diethylenetriamine, Η, Ν ^ΜΙ -Dimethyl-triethylenetetramine etc.

Preferred polyisocyanates include diisocyanates, such as, for example, tetramethylene diisocyanate, hexamethylene diisocyanate, m-xylene diisocyanate, p-xylylene diisocyanate, ^, ^ '-diinethyl-l ^ -xylylene diisocyanate, cyclohexane-1,4-diisocyanate, dicyclohexylmethane-4,4 ¹ -diisocyanate , m-phenylene diisocyanate, p-phenylene diisocyanate, l-alkylbenzene-2,4- and 2,6-diisocyanates, such as toluylene-2,4 and 2,6-diisocyanate, 3- (a-isocyanato -) - phenyl isocyanate, 1 -Benzylbenzene-2,6-diisocyanate, 2,6-diethylbenzene-1,4-diisocyanate, diphenylraethane-4,4 * -diisocyanate J5,3 * -dimethoxydiphenylmethane-4,4-diisocyanate, naphthylene-1,4-diisocyanate. Trifunctional and multifunctional polyisocyanates can also be used, for example toluene-2,4,6-triisocyanate or polymethylene-polyphenyl-polyisocyanate obtained by aniline-porraaldehyde condensation and subsequent phosgenation. In addition, isocyanates which contain carbodiimide uretonimine or isocyanurate groups can also be used. Mixtures of the

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use the aforementioned isocyanates. In addition, one can use conversion products of polyhydric alcohols with polyhydric isocyanates or use polyisocyanates like them e.g. according to German patents 1 022 709 and 1 027 394 can be used.

The polyisocyanates containing urea groups produced by the process according to the invention are, as already mentioned at the outset, valuable starting materials for the production of both foamed and non-foamed polyurethane plastics. . _φ ■

The present invention is therefore also the Use of the polyisocyanates containing urea groups obtainable by the process according to the invention as the isocyanate component in the production of foamed and non-foamed polyurethane plastics using the isocyanate polyaddition process.

To be used as a reaction partner for the invention Polyisocyanates or polyisocyanate solutions are "numerous hydroxyl and / or", particularly in foam production carboxyl group-containing compounds are suitable. As a rule, polyhydroxy compounds are those with molecular weights from 100 to 5000 are possible, e.g. several hydroxyl groups Polyester, polyether, polythioether, polyacetals, Polycarbonates, polyester amides, such as those used both for the production of homogeneous and for the production of cellular polyurethanes are known per se.

The hydroxyl polyesters in question are, for example, reaction products of polyhydric alcohols with polybasic carboxylic acids, how they are used in technology in all variations. Instead of the free carboxylic acids, however, the corresponding polycarboxylic acid anhydrides, polycarboxylic acid esters

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can be used. As individual representatives for this are named as examples: succinic acid, adipic acid, sebacic acid, phthalic acid, isophthalic acid, phthalic anhydride, Maleic acid, maleic anhydride, monomers, dimers and trimers Fatty acids, dimethyl terephthalate, etc. As polyol components come e.g. ethylene glycol, propyl "englycol- (1,3), Butylene glycol (1,4) and - (2,3), glycerine, trimethylolpropane, Hexanetriol (1,2,6), butanetriol (1,2,4), trimethylolethane, Pentaerythritol, mannitol and sorbitol, methyl glycoside, also polyethylene glycols, Polypropylene glycols, polybutylene glycols in question. Polyesters with terminal carboxyl groups are suitable also for the inventive reaction with the polyisocyanates.

The hydroxyl polyethers which can be considered according to the invention are also those of the type known per se and are, for example, by polymerizing epoxides such as ethylene oxide, propylene oxide, butylene oxide, styrene oxide or epichlorohydrin, optionally on starter components with reactive hydrogen atoms such as alcohols or amines, e.g. glycerol, trimethylolpropane, pentaerythritol, Sorbitol, ammonia, ethanolamine, ethylenediamine, ethylene glycol, propanediol, butanedi oil, resorcinol, hydrofuran, 2,2-bis -f p-hydroxypheny 1) propane, Bie-f p-hydroxyphenyl) methane, Bia-N ^ H-alkyl-toluylendiamln, Bie-H, H ¹ -alkyΙα iaminodipheny! Methane produced.

Sucrose polyethers are also suitable according to the invention. Particularly noteworthy is the foamability of the urea-modified polyisocyanates with a high OH * number of high-ethylene oxide rigid foam polyethers. Such polyethers have the application advantages of low viscosity and higher activity, caused by the presence of primary OH groups. Such polyethers are difficult to foam with unmodified organic polyisocyanates such as tolylene diisocyanate and 4 _f 4 '> diisocyanetodiphenylmethane for reasons of poor miscibility

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Compressive strength and heat stability excellent Possess tenacity.

Representatives of the polyhydroxy to be used according to the invention! Connections are e.g. in Saunders-Frisch, "Polyurethanes, Chemistry and Technology", Volumes I and II, Interscience Publishers 1962 and 1964 (page 32 f. Volume I and page 5 and page 198 f. Volume II) as well as in the plastic manual, Volume VII, Vieweg-Höchtlen, Carl-Hanser-Verlag, Munich 966, e.g. on pages 45 to 71. Epoxy resins, Hydrogenation products of ethylene, olefin, carbon oxide copolymers, phenol-formaldehyde reacted with alkylene oxides such as Urea-formaldehyde resins can also be used. Also low molecular weight polyhydroxy compounds, e.g. the already mentioned type and / or chain extenders such as glycols, diamines or water, aldimines and ketimines are used proportionally.

The foam itself is produced by known processes at room temperature or elevated temperatures by simply mixing the polyisocyanate combinations with the hydroxyl and / or carboxyl groups, with water, accelerators, emulsifiers and other auxiliaries such as flame-retardant substances and blowing agents being used if necessary. In this case, machine devices are advantageously used, such as those described, for example, in French patent ^{specification 1 Q7 1} * 713.

Suitable flame-retardant substances are according to the prior art known in large numbers and generally contain phosphorus and halogens. Antimony, bismuth or boron compounds are also possible. An overview of known and advantageous flame retardants is given in the chapter "Flame-retardant. Substances",

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Pages 110 - 111 in the Kunststoff-Handbuch, Volume VII, Polyurethane, von Vieweg-Höchtlen, Carl-Hanser-Verlag, Munich 1966. The Flame-retardant substances are generally used in amounts of 1 to 20 wt. -JfS, preferably 1 to 15 wt .- ^, based on the Amount of the polyisocyanate combinations used, also used.

For example, alkanes, haloalkanes or in general can be used as blowing agents low-boiling solvents in question, e.g. methylene chloride, monofluorotrichloromethane, difluorodichloromethane, Acetone, methyl formide, etc. Gas-releasing compounds such as azo compounds can also be used as blowing agents at higher temperatures or diurethanes of bis-half acetals and two Mole of formaldehyde and one mole of ethylene glycol in question.

Tertiary amines such as triethylamine, Dimethylbenzylamine, tetramethylethylenediamine, N-alkylmorpholines, Endoethylene piperazine, urotropine, hexahydrotriazines such as trimethylhexahydrotriazine, 2,4,6-dimethylaminomethylphenol or organic metal salts such as tin (II) acylates, e.g. tin (II) salts of 2-ethylcaproic acid, dialkyltin (IV) acylates such as dibutyltin dilaurate or acetylacetonates of heavy metals, E.g. of iron in question. \

As emulsifiers, e.g. oxethylated phenols, higher Sulphonic acids εμίίοηΐβ ^ εβ castor oil, oxethylated castor oil, sulfonated ricinoleic acid or ammonium salts of oleic acid are used will. Foam stabilizers are, for example, those based on polysiloxane-polyalkylene glycol copolymers or basic silicone oils. Other possible emulsifiers, catalysts and additives are e.g. in "Polyurethanes, Chemistry and Technology", Volumes I and II, Saunders-Frisch, Interseience Publishers, Listed in 1962 and 1964.

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Containing the amounts of urea polyisocyanates used As a rule, polyisocyanate solutions should correspond to the total available be equivalent of reactive hydrogen atoms, but if desired they can also be in excess or deficiency come into use. In the case of the production of foams, when using water as a blowing agent,

Speaking excesses of polyisocyanates appropriate to the water content use. Excess amounts of isocyanates can also be added in the course of the foaming process of 3- or 5-valent phosphorus compounds such as phospholidines, Phospholine oxides, tertiary esters, amides or ester amides the phosphorous or phosphoric acid as isocyanurate groups, uretdione groups and / or carbodiimide groups in the foam to be built in.

The foams obtained using the urea polyisocyanates are widely used, ζ, B. In construction ala building boards, sandwich elements, ceilings, breast plates, for thermal insulation in refrigerated cabinets !!, refrigerated warehouses, refrigerated trucks and refrigerated containers, also in road and rail construction, for technical insulation of pipes, for insulation of tank farms and in shipbuilding, as air filters and Miter for hydrocarbons in internal combustion engines as _p? erpackungsmaterial to protect against surges. The foam-like products of the process can be hard, semi-hard and flexible, so that the products of the process can also be used as cushioning material. It is also possible to use the process according to the invention for the production of semi-hard and hard fora-foamed polyurethane plastics with a compact surface and cellular core, surprisingly smooth, homogeneous and heat-resistant hand areas as well as wedge-shaped cores being obtained.

Diurea diisocyanates from the aforementioned aliphatic, cycloaliphatic or araliphatic diamines and lightfast diisocyanates such as tetramethylene diisocyanate, hexamethylene diisocyanate, m- and p-xylylene diisocyanate and isophorone diisocyanate can be used to produce lacquer coatings, coatings and elastomers of the highest lightfastness. Le A 13 1QB - 10 -

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Examples

BeiB £ iel_1_

672 parts by weight of hexamethylene diisocyanate are heated to 6O ⁰ O. With thorough stirring, 272 parts by weight of N ^ li'-diisopropyl-m-xylylenediamine are added dropwise to the polyisocyanate in the course of 3 hours. It is cooled and a crude solution is obtained which contains about 64% by weight of a diurea diisocyanate of the ideal formula

CH

CH ₂ -NC-NH- (CHa) ₈ -NCO 0

CH ₂ -N- C-NH (CHa) ₆ -NCO I "
CH O

H ₃ C CH ₃

contains. NCO content of the solution: 23.6 ^. The solution obtained is in the thin-film evaporator of monomeric? Freed hexamethylene diisocyanate at 0.02 torr at 80 ° C. A viscous, lightfast diurea diisoeyanate with an NCO value of 14.5 % is obtained »

While the aforementioned raw solution to produce lightfast cellular plastics can be used, the im Thin-film evaporator-cleaned diisocyanate can be used as follows to produce lightfast paint coatings:

50 parts by weight of a polyester made from 3 moles of phthalic acid and 4 moles of trimethylolpropane with a hydroxyl group content of 10.1 # are mixed with 50 parts by weight of a solvent mixture of equal parts of toluene, ethyl acetate, butyl acetate and glycol mono-diethyl ether acetate and 53 parts by weight of titanium dioxide (rutile type)

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processed into a paste. This paste then sets to a further 90 parts by weight of Lösergemjgches and 1.1 parts by weight of a ■ "Polyvinylmethyläthers as a leveling agent to, JDFM mixture _r wircl * ,, a solution of 86 parts by weight of the purified in a thin film evaporator diurea diisocyanate dissolved in 50 parts by weight of xylene / Ä thy lglykolace tat (1: 1) admixed. After applying this paint mixture to wood, metal or glass, dry, lightfast paints are obtained after 8 to 12 hours. After 3 days, the films are fully cured, solvent-resistant and have excellent gloss retention *.

BeispfelJ?

672 parts by weight of hexamethylene diisocyanate are reacted under the conditions of Example 1 with 200 parts by weight of Ν, Ν'-diisopropylhexamethylene diamine. This gives a crude solution containing about 61 wt -.% Of a diurea diisocyanate of the formula idelaisierten

H ₃ C ^
C.

NC-NH- (CH ₂ ) β-NCO

I " I 0

(CHg) ₀
NC-NH- (CHa) β-NCO

CH
/ \

H ₃ C CH ₃ . :

contains. NCO content of the solution: 27.7 # · The monomers are liberated as described in Example 1). NCO content of the viscous polyisocyanate: 12.2 %.

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A 50 # solution of this polyisocyanate in ethyl acetate, containing 0.02 wt .- # tin (II) acetate is applied to glass. The one-component paint mixture crosslinks after 24 hours to a lightfast clear varnish of high elasticity, good chemicals durability and excellent gloss retention.

Beisgi £ 1 ^ 3

1008 parts by weight of hexamethylene diisocyanate are reacted with 240 weight steles of ^{N, N 1 -diisopropylisophoronediamine under the conditions of Example 1.} A crude solution is obtained which contains about 46% by weight of a diurea diisocyanate of the idealized formula

H) -NC-NH- (CHa) ₈ -NCO

0 H ₃ C CH ₂ -NC-NH- (CH ₂ Je-NCO

I Il

10

CH / \

H ₃ C CH ₃ .

contains. Crude solution A: 32.9 % NCO

Replacing the amount of hexamethylene diisocyanate used in this example with 6 moles of isophorone diisocyanate or m- and p-xylylene diisocyanate, completely clear crude solutions become again The highest storage stability is obtained, which does not lead to the separation of insoluble substances even after standing for months Polyureas tend to be.

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This example shows the usefulness of the diurea diisocyanate prepared in Example 3 for the preparation of rubber-elastic coatings.

200 parts by weight of a polyester made from adipic acid and ethylene glycol with an OH number of 56 are dehydrated at 120 ° C in 14 Torr, then at 70 ° C with 200 parts by weight of methyl ethyl ketone and 25.6 parts by weight of the crude solution A of the example (NCO = 32.9 % ) mixed. The mixture is first heated for 2 hours at 6o C and, after a sharp increase in viscosity of the solution, 100 parts by weight. Add dimethylformamide. The polyaddition is completed at 70 ° C. in 3 hours. If this solution is applied to fabric or wood, a non-sticky coating is obtained, which is very lightfast and has a high degree of elasticity.

a) 497.11 g of N, N ¹ -diinethyl-4,4 ¹ -diaainodiphenylmethane are added dropwise to 1928 g of a mixture of 80 % 2,4- and 20 % 2,6-toluylene diisocyanate with stirring. An isocyanate mixture containing stable urea groups and having 29.2 % NCO and a viscosity of 980 cP / 25 ° C. is obtained

b) A mixture of 100 g of a propylene oxide polyether started on sorbitol with an OH number of 470, 1.5 g of endo-ethylene piperazine, 1 g of silicone stabilizer (SF 1109 from General Electric) and 40 g of monofluorotrichlomethane is mixed with 120 g of the under 4 a) Isocyanates described intensively stirred. A hard PUR foam with the following mechanical properties is obtained:

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Compressive strength: 2.0 kp / cm ^2, thermal flexural strength: 130 ° C

c) A mixture of 10Og of one based on trimethylolpropane and sucrose (ratio approx. 1 ι 1) started ethylene © xid polyethers with an OH number of 510, 1 g silicone stabilizer (SF 1109 from General Electric) 0.3 g endo-ethylene piperazine and 40 g of monofluorotrichloromethane are intensively stirred with 130 g of the polyisocyanate described under 4 a). A hard FUR foam is obtained with the following mechanical properties:

Volume weight: 28 kg / m ³

Compressive strength: 2.1 kp / cm ^2, noise bending strength: 136 ° C

a) To 1918 g of a crude ^, ^ '- diiaocyanato-diphenylmethane at a roughness temperature of 94 g, Ν'-diethyldiarainodiphenylaethane added dropwise. A polyisocyanate containing urea groups is obtained with 27 56 NCO and a viscosity of 1932 cP (at 25 ° C)

b) A mixture of 100 g of one started on sucrose Propylene oxide polyethers of OHZ 370, 1 g of endo-ethylene piperazine, 0.5 g water, 1 g silicone stabilizer (SF 1109 from General Electric) and 40 g monofluor «- trichloroethane is stirred intensively with 117 g of the polyisocyanate prepared under 5 a.). Man receives a hard PUR foam with the following mechanical properties:

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Volume weight: 33 kg / m- *

Compressive strength: 2.7 kp / cm ^2, thermal bending strength: 140 ° C

For example £ iel_6

As described under Example 4a), 268 g of a mixture of 80 % 2,4 and 20 % 2,6-toluene diisocyanate with 65.25 g of N, N'-diethyl-4,4'-diamino-2,2'- -dimethyl-diphenylmethane implemented. A urea diisocyanate with 32.2 % NGO and a viscosity of 66.3 is obtained. cP (at 25 ° C).

Example _< _7_

As in Example 4a), 282 g of 2,4-tolylene diisocyanate are obtained with 65.2 g of NjN'-dimethyl-pp'-diamino-diphenyl-2,2-propane implemented. A urea diisocyanate containing 32.8% NCO and having a viscosity is obtained of 52.6 cP (at 25 ° C).

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Claims (2)

Patent claims: 1. A process for the preparation of liquid di- and polyisocyanates containing urea groups from amines and polyisocyanates, characterized in that polyisocyanates from -20 to + 8O ⁰ C with polyamines containing only secondary amino groups in a ffCO / JIH ratio of 2: 1 to 100: 1 implemented. 2. Use of the polyisocyanates containing urine groups prepared according to claim 1 as the isocyanate component in the manufacture of foamed and non-foamed Polyurethane plastics based on the isocyanate polyaddition process. Le A 15 108 - 17 - 10 9883/1937