DE1595748A1 - Polyisocyanate and polyamine compounds hardening due to the action of moisture - Google Patents

Description

DIPL-INQ. DIETER JANDER DR.-II PATENT LAWYERS

1 BERLIN 33 (DAHLEM)

HOTTENWEG 15

Phone: 76 13 03

Telegrams: Contld.rat ion Berlin

May 27, 1966 793/12230 EN

Pat ent on registration the .company

GEIiEiLil · MILLS, IN, C. ■ iniiear> olis, Minnesota 55440, UNITED STATES.

By. Moisture hardening P ο lyi so cyan at- and

Polyamine mass

The invention relates to a novel curing agent which is able to cure at room temperature to form cured polyurethane compositions. The novel curing agent is based on the reaction of a polyamine composition with a polyisocyanate to form the corresponding polyureas. However, the polyamino compound used is either partially or completely blocked and thus gives a product which has no more than one active hydrogen atom which is capable of reacting with the polyisocyanate. The blocked polyamine and the polyisocyanate Hasse containing is resistant in the absence of moisture and can be converted to the final cured Polyharnstoffprodukt who the by einfaoh the same is exposed to moisture, which converts the blocked polyamine compound in the free Polyaain, which then is able with the Polyiaooyanat

Poitichcckkonto Berlin-Weit 174384 Berliner Bank AG., Oepoiitenkatte 1

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DIPL-INQ. DIETER JANDER DR.-INC /. MANFRED BONING

PATENT LAWYERS I 5957 A 8

- 2 to implement.

The blocked polyamine compound is a ketimine or a Aldimine, which is produced by the reaction of a primary amine with a ketone or an aldehyde. If not available of moisture, the ketioin or aldimine is in the presence of the polyisocyanate is resistant, but in the presence of moisture, even in the presence of atmospheric moisture, ketimine forms or aldimine back the primary amine compound, which is then in is able to react with the polyisocyanate. By applying the Hasse according to the invention it is thus possible to cast a film of the mixture and the same of the humidity suspend, whereby a polyurea coating is formed, which becomes tack-free for a short time after thorough curing has been carried out at room temperature and then excellent Has properties. It is also possible to make thicker castings from the mixture and upon exposure curing takes place in the same way with respect to atmospheric humidity. Some of the components of this system are liquids and it is thus possible to produce solvent-free coatings and thus to build up thicker coatings in just a few applications. Optionally, of course, solvent systems can be used can be applied. This system according to the invention can also be used for the production of leveling compounds that cure at room temperature, Sealants and adhesives are applied.

One problem on which the invention is based therefore exists in creating a novel coating mass that can be used in the Is able to react with humidity at room temperature in such a way that that curing results to form a polyurea. Another problem on which the invention is based consists in creating a compound that mixes certain polyisocyanate products with certain polyamine compounds * - contains applications in which the primary amine groups are blocked by ketimine or aldimine groups.

The invention relates to the use of polyisocyanates that are sufficiently low. äeact! have gas velocity in order to thus being able to work with amino compounds at speeds cure that are controllable so as to avoid exothermic reactions that tend to the products used

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DITL-INQ. DIETER JANDER DR.-INQ. MANFRED BONINQ PATENT LAWYERS »595748

destroy. In general, the polyisocyanates used are aliphatic, cycloaliphatic or araliphatic polyisocyanates. Aromatic isocyanates are generally quite reactive and are therefore to be avoided according to the invention with the exception that they are used in a mixture with other polyisocyanates which have sufficiently low reactivity so that the entire composition cures at a controllable rate. Typical isocyanates which can be used according to the invention include the olymethylene diisocyanates such as ethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexaraethylene diisocyanate, etc. alkylene diisocyanates such as propylene 1,2-diisocyanate, butylene 1,2-diisocyanate, butylene 1,3- diisocyanate, butylene-2,3-diisocyanate, etc., alkylidene diisocyanate, such as ethylidene diisocyanate, butylidene diisocyanate, etc. Cycloalkylidene diisocyanates, such as Cjdopentylidene diisocyanate, Oyelohexylidene diisocyanate, etc., triisocyanates, such as 1,2,4-butanetriol triisocyanate, 1,3.3-rentanetriisocyanate, butane-1.2. 2-triieo- · cyanate, etc. Mixtures of two or more such polyisocyanates can optionally be used. Examples of araliphatic polyisocyanates that can be used according to the invention include: p-phenylene-2.2 ^l -bis (ethylocyanate ;, pi-henylen-3 · 3'-isipropylisoeyanax ), p-phenylene-4.4 ^t -t) is ( _l outylisocyana'- ) , mi nenyien-2.2'-bis (ethyl isocyanate J, 1,4-naphthalene-2. ^ '- bis (ethyl isocyanate, 4.4'-diphenylene-2.2 ¹ - dis (äthylieocyanac ), 4.4' -i3iphenylenäther- 2.2'-bistäthylisocya-γ> 2ϊ), tris (2. 2 ^1. 2 "-AethyIisocyanaxbenzol), S-dis (propyl-3-isocyanate), S-met-hoxyphenylen-lioocyanat), 5-ΰyanΰphenylen-1.3- bisCpropyl-3-isocyanate) and 5-methylphenylene-1.3-bis (propyl-3-isocyanate) .ε

A particularly useful group of polyisocyanates for the purposes of the invention is that described in the US patent (US patent application SN 250,211). These polyisocyanates are obtained from polymeric fatty acids and have the following idealized structural formula:

- 4 _ 0 0 9 8 2 0/1611 BAD ORIGINAL

DIPL-INC DIETER JANDER DR.-INC-MANFRED BONINQ

where y is 0 or 1, χ is a number from 2 to about 4 and R is the hydrocarbon group of the polymeric fatty acids. Preferably χ is 2.

The polyisocyanates in which y is equal to 0 are made by converting the polymeric fatty acids into the corresponding polymeric ones Acid chlorides, reacting the acid chlorides with a metal azide to form the polymeric acyl azides, and then Heating the acyl azides to form the polyisocyanates. This manufacturing method can be understood from the following Present equations (using the dimeric fatty acid as an example):

3 R (COOH) ₈ + 2 PCl ₈ > 3 R (COCl) ₈ + 2 H ₈ PO ₈

RCCOCl) ₈ + 2 NaN ₈ > R (CON ₈ ) ₈ + 2 NaOl R (CONg) ₈ >> R (NCO) ₈ + 2 N ₈

The polyisocyanates in which y is equal to 1 are prepared by converting the polymeric fatty acids into the corresponding polynitriles and then hydrogenating the polynitriles in the presence of ammonia and a catalyst such as Raney nickel to form the polyamines. The polyamines are then reacted with phosgene to form the polyisocyanates. The manufacturing process can be represented by the following equations (using a dimeric fatty acid as an example):
R (COOH) ₂ + 2 NH ₃ > R (CN) ₂ + 4 H ₂ O

^ ^GIf ) a + 4H ₂ »R (CH ₂ NH ₂ ),

R (CH ₂ NH ₈ ) ₈ + COCl ₂ - ^ R (CH ₂ NOO) ₂ + 2 HCl

The polymeric fatty acids useful as starting materials for producing the polyisocyanates are produced by polymerising a fatty acid. The term "fatty acid" used here refers to naturally occurring and synthetic monobasic, aliphatic acids, the hydrocarbon chains of which have 8 to 24 carbon atoms. The term "fatty acids" thus includes saturated acids which are unsaturated by double bond and triple bond. The term "polymeric fatty acid residue ¹¹ generally refers to divalent, tri-valent

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DIFL-INC DIETER JANDER DR.I NQ. MANFRED BONINC PATENT LAWYERS 1535748

valuable and polyvalent coke hydrogen residues from dimerized Fatty acids, trimerize fatty acids and higher polymers of fatty acids. These two-valued and three-valued best become here as "dimeric fatty acid residue" and "trimeric fatty acid residue" designated.

That from these dimeric fatty acid residues and ptrimeric fatty acid residues Derived polyisocyanate can be identified below by the designations dimeryl isocyanate and trimeryl isocyanate. These products are made from mixtures of dimers and trimeric fatty acids are produced, and the relative amounts can be controlled by the extent to which the individual Compounds in the preparation of the dimeric and trimeric fatty acids have been separated.

The polyisocyanates derived from polymeric fatty acids are particularly useful for a number of reasons. Coatings made from this have good wetting properties, good adhesiveness and good water resistance and corrosion resistance. Elastomeric polyureas based thereon are characterized by a high degree of elasticity, the is maintained even at low temperatures. Furthermore, these polyisocyanates can be due to their low Easy to handle vapor pressure under normal conditions and toxicity hazards are neglected. Because of them low reactivity towards compounds with active hydrogen and practically nonexistent effectiveness tertiary amine groups as catalysts for these polymeric fatty acid polyisocyanates, it is also possible to use mixtures the polyketimines and polyaldimines with these isocyanates produce and the masses have in contrast to some of the more reactive aliphatic polyisocyanates and aromatic polyisocyanates have a very good service life.

The polyisocyanates given above react sufficiently slowly to be useful according to the invention for the production of stable compositions in a mixture with aldimines and ketimines. They aromatic polyisocyanates on the other hand generally xu reactive for this purpose may, however, ale tin part of a mixed polyisocyanate be used daa contains the specified less reactive isocyanates. _ c _

009820/1611

DIPL-INCDlErEKJANOEIt WL-INO. MANFRED BDNINO

Typical aromatic polyisocyanates which can be used in this way include tolylene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 1-methyl-2T4-phenylene diisocyanate, naphthylene-1 ^ -diisocyanate, diphenylene- ^{4,4 1} -diisocyanate, etc., aliphatic-aromatic diisocyanates, such as xylylol-1,4-diisoGyanat, xylyl-l ^ -diisocyanate, 4,4 * -diphenylenmethanediisocyanat.

The polyisocyanates which can be used according to the invention can be used in the form of the free isocyanate, or the same quantities as is customarily used in the Pail can be used in the form of so-called prepolymers. These prepolymers are the reaction products of polyols or polyester polyols with the polyisocyanates in such a way that essentially 1 part of polyisocyanate is reacted with one equivalent of the hydroxyl group, and the reaction product is thus a prepolymer with terminal isocyanate groups. These terminal Isooyanatgruppen can then nen for! Reaction with ketimines and Aldi Argentina are applied. It goes without saying that the term "polyisocyanate" is understood to include prepolymers with a terminal isocyanate group of simple polyols, polyether polyols and polyester polyols. Typical polyols include trimethylol propane, 1.4.6-hexanetriol, glycerine, ethylene glycol, diethylene glycol, 1,4-butanediol, 1,4-butenediol, 1,3-butanediol and the like. The polyether polyols are homopolymers and copolymers of ethylene oxide, propylene oxide, butylene oxide and the like with a terminal / hydroxyl group. The polyester pdyols are polymers with a terminal hydroxyl group which can be prepared from the specified polyols and any of the typical polybasic acids used for the preparation of the polyesters. It is understood, of course, that if any of the prepolymers of the type indicated above are employed, the finally cured compound will contain both urethane groups and urea groups. However, the term "polyureas" is still applicable to these pounds since they contain a variety of urea groups.

009820/1611

DIPL-INO. DIETER JANOER ML-INO. MANFRED RDNINQ

Practically every polyamine that is capable of calibrating it To implement isoyanate and preferably does not have very much than 2 secondary amine groups, can be used for the invention Purposes. The preferred polyamines are the alkylene polyamines and the substituted alkylene polyamines. the preferred polyamines «are selected on the basis of the following formulas t R A. H N (H

"Obei R a difunctional" aliphatic ^ hydrocarbon group with 2-48 carbon atoms, R * water or an aliphatic hydrocarbon group with 1 to 24 carbon atoms and η is a number from O -20.

B. H

where R and η have the values defined above, but preferably R is an alkylene radical having 2-6 carbon atoms and a is O to 3. _Rt

C * Ii ₁ HEIRNH,

190 for R and R ^{1 have} the values defined above, but preferably R is an alkylene radical with 2-6 carbon atoms and R * is a radical with 8 to 24 carbon atoms.

D. HgNR RHHg

HR "HH ₉ HR RHH,

where R has the value defined above, but preferably an alkylene radical with 2-6 carbon atoms and R ″ the dimeric Is the hydrocarbon free of dimerized fatty acids and preferably has 24-48 carbon atoms. All of the above amines should preferably have no more than 2 secondary amine groups.

Typical of the amines that can be used are ethylenediamine, diethylenetriamine, triethylenetetramine, etc. and the corresponding Propylene, butylene etc. amines, H.H-diaminopropyl stearylamine, etc.

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PIPL-INO. DIETEK JAN DE «Wt-INO-MANfMDlONINO iCflt» »/ fl PATENT LAWYERS I 5 9 D 7 4 8

The primary amine groups in the above polyainine compounds "Convert ground to Aidimine or Ketiminβ yermittele" with one Converted to carbonyl group. Such an carbonyl group can have the following theoretical structural formula *

where R ₁ and R _{1 are selected} from the group consisting of H and alkyl and both are practically inert to the reaction which leads to the formation of the aldinine or ketimine base, the carbonyl compound preferably has a low molecular weight (C ₁ to O ₆ aldehyde or ketone), which is volatile, so that the excess which has not reacted can be easily removed after the water has reacted, releasing the free amine and the aldehyde or ketone compound. It is often preferred to use a carbonyl compound that boils below or close to the boiling point of water or easily distills off with water. Preferred examples of the carbonyl compound include such volatile C 1 to C _e aldehydes and ketones, such as acetone, methyl ethyl ketone, diethyl ketone, methyl propyl ketone, methyl propyl ketone, methyl n-batyl ketone, methyl isobutyl ketone, methyl tert-butyl ketone, methyl isopropyl ketone, ethyl isopropyl ketone, ethyl isopropyl ketone, ethyl isopropyl ketone, ethyl isopropyl ketone , Butyraldehyde, zsobutyraldehyde, etc. (ie up to and including hezanone and hexanal).

When making the inventive masses are two Components simply mixed together and then kept in / contact with moisture, both added Moisture than auoh humidity, the liquid components can easily be mixed with each other to form the misshapen flätü & gkeit be mixed. In the event that two liquids are not compatible, they can be used by means of suitable solvents are made compatible. The solvents can also be used where one or several of the components are a solid. The products can be packaged and kept out of contact with moisture until they are applied to the application. In your application, it is preferable to work with the humidity of the air, which has a relatively high degree of humidity, even if it is it is possible to add moisture directly to the mass if necessary.

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DIPL-INO. DIETER JANDER DR.-INQ. MANFRED IDNINQ PATENT LAWYERS | 595748

Me invention is explained in the following for example:

example 1
Condensation of triethylenetetramine with methylobutyl ketone.

Ss are 219 g of triethylenetetramine and 450 g of methylipobutyl ketone dissolved in 500 ml of benzene in a 2-liter 3-neck round-bottom flask, who is armed with a Barrett trap, who is equipped with a The cooler connects to a Drierite Trooken tube is equipped. The flask is warmed and the solution refluxed for 8 hours. Then there are 44 ml of water in the Collected Barrett's Trap. The flask is then cooled and 50 g of methyl isobutyl ketone were added, as well as the solution more Reflux for 2 hours (a total of 50 ml of water are collected) and then cool. There are then 50 g Methyl isobutyl ketone was added to the flask and the solution was refluxed for an additional 8 hours (54 ml of water in total collected). The flask is then cooled and the benzene and excess methyl isobutyl ketone removed under reduced pressure. 315 g of residue are obtained in this way. The product is referred to as ketimine A in the following.

Example 2

Condensation of N.N-Diaminopropylstearylamine with methyl isobutyl ketone.

There are 76.6 g of N.N-diaminopropyl stearylamine and 100 g of methyl isobutyl ketone dissolved in 150 ml of benzene in a flask equipped as described in Example 1. The flask is heated and the solution refluxed for 6 hours (a total of 11.8 ml of water are collected). After removal of the solvent and excess methyl isobutyl ketone remains a residue of 111.6 g. This product is referred to herein as Ketimine B.

Example 3 .
Condensation of iminobispropylamine with methyl isobutyl ketone.

There are 131 g of iminobispropylamine with 300 g of methyl isobutyl ketion brought in 350 ml of benzene in the manner described in Example 1 to implement. After removing the excess The remaining residue weighs ketones and solvent

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DIU..INO. DIETER JANDER ML-INQ. MANfRf D »ONING FATENTAWALTE I 5 9 5 7 4 θ

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291 g * The analysis of the residue mediated infrared analysis shows that the same In agreement old the expected Diketimine is present, which is referred to herein as Ketimine C.

Example 4 Condensation τοη Methyliminobiapropylamin with Methylisobutyl-

ketone.

145 g of methyliminobispropylamine with 300 g of methyl isobutyl ketone in 350 ml of benzene are described in Example 1 Wise implemented. After removing the excess ketones and solvent, the remaining residue weighs 304 g. Analysis of the backwater by means of infrared analysis shows that the same in agreement with the expected diketimine is present, which is referred to as ketimine D in the following.

Manufacture of polyureas.

Play 5

There are 15 »0 parts by weight of dimeryl isocyanate, which has been produced from dilinolenic acid of tall oil via the amine phosgene route and 3.8 parts by weight of ketimine A are used.

These components are mixed with one another and applied to tin and glass substrates with a film thickness of 0.038 mm. It takes 2 hours for the films to be tack-free and the gelation time is 6 hours. After curing for 14 days at 22 ^° C. and 50% relative humidity, the films have the following properties: Pencil hardness 6B

Rocker hardness 15 G.E. Extensibility 60% +

Example 6

A mixture of 15 »0 parts of dimeryl isocyanate according to Example 5 and 4.45 parts of diketimine, prepared from diethylenetriamine and methyl isobutyl ketone, is applied to tin, steel, wood and glass substrates with a film thickness of 0.038-0.125 mm. The films require 2 hours to be tack-free and the gel time of the mixture is 50 hours. In order to achieve complete curing, the films are allowed to cure for 14 days at 22 ^° C. and 50% relative humidity. The following is a summary of the properties of the above coating. 009820/1811 -11

Please j AN MEK ML-INQt MANf * Z »MMIMQ ./. _r Lead tnjlrte 79 Hooker-Hllrt 14. _Γ

<*. «· Extensibility 6Ojt +

Xlebtoaft «a steel,. auegesehaet

Resistant to solvents and solvents -good;

Taber! »Rubbed 7» 5 ag loss after 1000

Afbeitegänge old one » _: Ofr-10 Bad. . :

The above Holepanel “earths a carbon fiber arc water hero with it brewed for 1014 hours and every change ί the oiling” of the coating is observed. After the expiry of the period of time, the original β lan "tone 82 was only 61, Terringert" order. '\

Example 7

Ee "ground 26" 2 parts diaeryiiaooyanat according to Example 5 (50 oily solution in a 111 de ". Löeungemlttelgealoh made of xylene and oil oil acetate) and 4> 4 parts Mondor CB-60 (an isocyanate copolymer from Mobay Olieeical Ooapaay, the by condensation of 2 equiralents TDI "with an equiTaleet of trimethylol propaln in a solution mixture of xylene and oleosol aoetate prepared", 4.45 files diketimin neon Beiapi! 6 and 5.35 parts of a solvent mixture made from xylene and celloaolraoetat ItI ffewiohtagritndlage applied. " ^:

These constituent parts «earth together with each other and

βchiedene Subatrate poured in a film dioke τοη 0.076 ma. ;

The oiling time since the oemleohes is 4.5 hours, and until ''

the films are tack-free, runs 1 stage. laoh ' 14 days for shepherds at 22 * 0 and 50 * normal humidity 8 en the brain has the following properties on t

Pencil hardness eg Booker hardness 27 S.B. Extensibility 60 * + Adhesive strength to aluminum and steel

chemical and chemical resistance good

Taber abrasion 18 ag Terluat after 1000

Work steps old a 08-10 lad.

. " ¹² -

009820/1611

BATH ORIGINAL DiPL-INQ. DIETER JANDER DR.-INQ. MANFRED BONINQ

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Example 8

26.5 parts of isocyanate prepolymer (NCO% = 7.94), which has been prepared from dimeryl isocyanate and a polyether diol from dimer fatty acid and diethylene glycol, with a molecular weight of 2000 and 6.2 parts of ketimine B are used mixed and then potted with a thickness of 1 mm. It is allowed to ^{cure for 14 days at 22 °} C. and 5094 relative humidity. The exposed surface becomes tack free in 16 hours. After curing for 14 days, the elastomer has the following properties:

Shore A hardness 45

22 ⁰ C -25 ⁰ C

, *
Tensile strength kg / cm 6.3 290

Water absorption after 28 days $ 0.6

Example 9

There are 60 parts by weight of "dimeryl isocyanate according to Example 5 and 19.6 parts by weight of ketimine C are used.

These two components are mixed together and then applied to tin, glass and steel substrates to a film thickness of 0.038 am applied. Until the films are tack-free, run 75 minutes and the gel time is 7 hours. The films are allowed to cure at 22 ° C. and 50% relative humidity. in the The following are the properties of the UeIi trains: Pencil hardness 7 B

Rocker hardness 10

G.E. Extensibility · 60% +

Adhesive strength very good

chemical and solvent resistance good

Taber-Aorieb 12 mg loss after 1000 ares

steps with a CS-IO Wheel.

Example 10

60 parts by weight of dimeryl isocyanate according to Example 5, 8.9 parts of diketimine according to Example 6 and 11.2 parts by weight of diketimine from ethylenediamine and methyl isobutyl ketone are used. The above components are mixed with one another and, as described in Example 9, applied. It takes 1 hour for the coating to be tack-free and the gelling time is 5 hours. After 14 days, the same hardened at 22 ⁰ C and 50 b relative humidity, then the coating has the following properties:? 009820/1611

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DIPL.-INQ. DIETER JANDER DR.I NO. MANFRED BONINQ PATENT Attorneys I 595748

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Pencil hardness 5B

Rocker hardness 16

G.E, extensibility ■ 60 # +

Adhesion or adhesive strength good

chemical and solvent resistance good

Taber abrasion 20 mg loss after 1000

Operations with an OS-IO wheel.

Example 11

There are 26.5 parts by weight of isocyanate prepolymer (NOO # = 7.94), prepared from dimeryl isocyanate and a polyester diol with a molecular weight of 2000, as in Example 8 and 3.9 Parts by weight of ketimine A are used.

The above ingredients are mixed together and then eat a thickness of 1.25 mm and shed for 14 days at 22 ⁰ C allowed to cure. The relative humidity is 4594. The exposed surface becomes tack free in 2 hours. The cured product has the following properties:

-25 ° C -46 ° 0

yy

Tensile strength kg / cm 29 330 430 ° / o elongation 123 117 86

Water absorption after 28 days of immersion = $ 1.43.

Example 12

There are 9.0 parts by weight of diethylenetriamine and ketimine Methyl isobutyl ketone, 19.8 parts by weight cellosolv-acetate-xylene mixture (1: 1 weight basis) and 10.8 parts by weight of p-phenylene-2.2'-bis (ethyl isocyanate) used.

The above ingredients are mixed together and applied to tin and glass substrates with a wet film thickness of 0.038 mm. It takes 45 minutes for the film to be tack-free and the gel time is 6 hours. After curing for 14 days at 22 ^° C. and 50 ° relative humidity, the films have the following properties : Pencil hardness 4B

G.E. Extensibility

tta # ^

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DIPL-INQ. DIETER JANDER Mt-INC. MANFKED BONING PATENT LAWYERS * | 595748

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Example 13

There are 5-6 parts by weight of ketiaine from ethylenediamine and methyl isobutyl ketone, 11.65 parts by weight of ethyl acetate and 12.35 parts by weight (of a polyisocyanate prepolymer made from hexanemethylene disocyanate and a poly oil, HCO content = ITji) and 2 drops Zinc naphthenate (8 # Zn) was used.

The above ingredients are mixed together and applied to glass, steel in the form of a black plate, and steel in the cold-rolled state with a film thickness of 0.038 mm. It takes 20 minutes for the film to be tack-free and the gel time is 5 hours. After curing for 3 days at 22 ^° C. and 50 ° relative humidity, the films have the following properties:

Rock hardness 14

G.E. Extensibility 60% +

Gardner impact strength 160 + 2.54 cm - 0.454 kg

Good bond strength (glass and steel in

Shape of a black plate).

009820/1611

Claims (13)

DlPL-INQ. DIET PATENT LAWYERS 1 BERLIN 5Y (DAHLEM) HOTTENWEO IS T «'. R [on: 7 * 13 03 Telegrams: Consideration Berlin May 27, 1966 793/12230 EN Patent application
of the company
GEKLRAL !, '. ILLS, INC.
Minneapolis, I «-innesota 5544C
United States "Claims" Polyocyanate and polyacrylate resins hardening by the action of moisture Polyamine mass, characterized in that the same a) a polyisocyanate, daa from the group consisting of aliphatic, oycloaliphatic and araliphatic Polyisocyanates selected iat, and b), a compound selected from the group consisting of Aldimines and ketinines are selected from aliphatic polyamines, contains. 2. Composition according to claim 1, characterized in that the polyaain is an alkylenepolyauin. 3. Hasse according to claim 1, characterized in that that the polyisocyanate corresponds to the formula (E) ((CH,) HCO) _x in which y is 0 or 1, χ is a number τοη 2 to about 4 and R the hydrocarbon group is τοη polymeric fatty acids, and the polyamines contain no more than two secondary amine groups. 009820/1611 - .-- West '* x; fJ Berliner Eer * 009820/1611 Pcstsci-eci k - 'c Ee- .-- West' * x; fJ Berliner Eer * AG. DepcS'tenke «Je DIPL-INQ. DIETER JANDER DR.-INQ. MANFRED BONINQ PATENT LAWYERS 1 5 9 5 7 A 8 4. Mass after. Claim 3 »characterized by» that the aliphatic ^ polyamine of the following formula H ₂ N (RNH) _n RNH ₈ corresponds, in which R is an alkylene group having 2 to 6 carbon atoms and η is a number from 0 to 2. 5. Maese according to claim 3, characterized in that that the polyamine of the formula H ₈ NRNRNH ₈ in which R is an alkylene group having 2 to 6 carbon atoms and R ^{1 is} a fatty acid having 8 to 24 carbon atoms. 6. Masee according to claim 3, characterized in that the aliphatic ^ polyamine is converted into an aldinine or ketimine by means of an Oarbonyiverbverbindungen-the formula R ₁ R ₈ WG = O, in which R ₁ and R ₈ from the group consisting are selected from H and alkyl groups with the proviso that the total number of carbon atoms in the carbonyl compound is not greater than six. 7. mass according to claim 3t characterized. that a ketirain of an alkylenepolyamine with a ketone that Contains 3 to 6 carbon atoms is present. 8. Composition according to claim 3, characterized in that the same contains an aromatic polyisocyanate. 9. mass according to claim 3 »characterized in that that the same is the diketimine from diethylenetriamine and methyl isobutyl ketone 'contains. 10. Composition according to claim 9 »characterized gekennzeichn et that the same is a prepolymer of toluene diisocyanate and one Contains polyol. 11. mass according to claim 3, characterized gekennzeich.n et that the same is the diketimine from ieinobispropylamine and methyl isobutyl ketone contains. 12. The mass according to claim 31 characterized et, that it contains the mixed diketimine of ethylenediamine and diethyientriamine with methyl isobutyl ketone. 009820/1611 ~ ³ ~ DIPL-INO. DIETER JANDER DR ₁ -INO-MANFREDBONINc _ PATENT LAWYERS I 0 O U / 4 8 13. A method for hardening polyurethane masses, thereby characterized in that the masses according to the preceding claims with moisture, in particular air moisture be brought into contact. 009820/1611