HK1081212B - Prepolymers containing silyl groups, the production thereof, and the use of the same in polyurethane foams - Google Patents

Description

Silyl group-containing prepolymers, their production and use in polyurethane foams

The invention relates to a prepolymer comprising at least one group I corresponding to the general formula:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom, A is C1-12 alkylene, Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2,

and optionally at least one group corresponding to formula (II):

-N(R¹)-C(O)-Y-R² (II)，

wherein R is¹Is H or straight-chain or branched, saturated or unsaturated C_1-18Alkyl radical, R²Is linear or branched, saturated or unsaturated C_1-44Alkyl, or of the formula R³-(O-CHR⁴-CHR⁴)_n-Wherein R is³Is linear or branched, saturated or unsaturated C_1-44Alkylene, preferably C_1-12Or C_2-8Alkylene oxideRadical, substituent R⁴Independently of one another, represent H or linear or branched C_1-4Alkyl, n is a number of 1 to 1,000, Y is O, S or NR²Wherein R is²As defined above, the total number of functional groups I and II in the prepolymer is 2 or more,

the present invention relates to compositions comprising such prepolymers, to processes for their production and to their use.

Moisture-curing polymers containing silyl groups are commonly used in the building and automotive industries as flexible and elastomeric coating, sealing and adhesive compounds. In such applications, the elasticity, bond strength and cure rate must meet stringent requirements. In addition, these silane-terminated polymers generally have water-repellent properties, imparting excellent water and heat resistance to sealants, coatings or adhesives produced therefrom.

There are many known alkoxysilane-terminated polymers that are particularly useful as flexible and elastomeric sealant, coating and adhesive compositions. Such compounds are primarily suitable only for applications in areas where importance is primarily attributed to the elasticity of the produced compositions. However, the known silyl-containing polymers are generally not useful in applications where, in particular, rapid curing of the adhesive or, in particular, low elasticity of the forming polymer is necessary or at least desirable.

The rapid cure of adhesives, sealants, and similar compositions provides a number of advantages, which are often desirable to users. For example, a fast curing adhesive can be used, for example, for bonding, where a prolonged fixing of the substrates to be bonded is too inconvenient. The use of sealants often also requires a rapid curing of the respective sealing adhesive in order to save time during sealing or to avoid laborious fixing of the parts to be handled.

However, to date, systems containing silyl groups of the type under investigation have generally been used to elastically cure polymers, more particularly in the field of adhesives and sealants. In this connection, the foaming of the prepolymer compositions known from the prior art generally leads to compressible polymers.

For example, WO98/28539 describes a sealant based on silane-modified polymers and fine-particle fillers, which is processed by conventional foaming equipment to form foamed plastic articles which exhibit high elasticity after application of compressive stress. However, the described foams cannot be used as part foams because their elasticity is too high.

WO00/04069 describes a prepolymer mixture for the production of sealants and insulating foams which comprises a prepolymer component, additives which are usually required for foaming of the foaming gas component. The known prepolymer mixture comprises, as a prepolymer component, a silyl group-terminated polyurethane prepolymer having at least two Si (OR) groups in the molecule_x(R)_3-xGroup, wherein R is C_1-6Alkyl, x is an integer of 1 to 3. Although the polymers described are suitable for the production of rigid foams, the thermal stability, fire resistance and burning characteristics of the products are not always satisfactory.

Systems based on crosslinked isocyanate prepolymers have hitherto been used predominantly, in particular for component foams. Although such systems are characterized to a large extent by sufficiently rapid crosslinking, they do present a number of disadvantages for the user and indeed. Thus, isocyanate groups have irritating and toxic effects on living tissue. If the isocyanate group-containing mixture is dispersed, for example by a blowing gas, an aerosol is formed and the user is therefore at risk of inhaling aerosol particles which are harmful to his/her health. In addition, due to their isocyanate-based content, the products must be properly noted in many countries. This usually means that empty containers containing the product residue or containers are still classified as hazardous waste and are therefore disposed of. In turn, consumer acceptance, particularly in the DIY arena, is greatly reduced.

A further disadvantage of the known systems is that the silyl group containing compounds used generally have a high polyether group content. Although polyether groups can provide a viscosity which can be adjusted within a wide range of the processability of the silyl group containing compounds used, their effect on the plasticization of the system as a whole means that the foams obtained have poor compressive strength and cannot withstand stress. In addition, owing to their water-absorbing properties, polyether groups promote the penetration of moisture into the corresponding foam, so that the long-term stability of the foam, above all its dimensional stability, is adversely affected.

The problem addressed by the present invention is therefore to provide prepolymers based on silyl group containing compounds which do not have any of the above-mentioned disadvantages of the known systems.

More particularly, the problem addressed by the present invention is to provide prepolymers which do not contain any or hardly any toxic isocyanate groups. A further problem solved by the present invention is to provide prepolymers suitable for producing strong foams capable of withstanding stress, more particularly prepolymers for producing component foams. A further problem solved by the present invention is to provide prepolymers with a wide range of adjustable viscosities when used to produce component foams. A further problem solved by the present invention is to provide prepolymers which ensure rapid curing of stress-resistant systems such as foams or adhesives.

It has now been found that a prepolymer comprising at least one group corresponding to formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom, A is C_1-12Alkylene, Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2,

and at least one group corresponding to formula (II):

-N(R¹)-C(O)-Y-R² (II)，

wherein R is¹Is H or straight-chain or branched, saturated or unsaturated C_1-18Alkyl radical, R²Is linear or branched, saturated or unsaturated C_1-44Alkyl, or of the formula R³-(O-CHR⁴-CHR⁴)_n-Wherein R is³Is linear or branched, saturated or unsaturated C_1-44Preferably C_1-12Or C_2-8Alkylene radical, substituent R⁴Independently of one another, represent H or linear or branched C_1-4Alkyl, n is a number of 1 to 1,000, Y is O, S or NR²Wherein R is²As defined above, the total number of functional groups I and II in the prepolymer is 2 or more,

and a prepolymer comprising at least one group corresponding to formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom and A is CH₂Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2, the polymer backbone of the prepolymer containing at least one Ar-L-Ar linked aryl group, wherein L is a covalent bond, a linear or branched, saturated or unsaturated C_1-6Alkyl radical, C_5-12Cycloalkyl radical, C_4-12Aryl or heteroaryl groups or isocyanurate, allophanate, urea, biuret, uretdione, carbodiimide, or ketimine groups, solving one or more of the problems set forth above.

The present invention therefore relates to a prepolymer comprising at least one group corresponding to formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatomA is C_1-12Alkylene, Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2,

and at least one group corresponding to formula (II):

-N(R¹)-C(O)-Y-R² (II)，

wherein R is¹Is H or straight-chain or branched, saturated or unsaturated C_1-18Alkyl radical, R²Is linear or branched, saturated or unsaturated C_1-44Alkyl, or of the formula R³-(O-CHR⁴-CHR⁴)_n-Wherein R is³Is linear or branched, saturated or unsaturated C_1-44Preferably C_1-12Or C_2-8Alkylene radical, substituent R⁴Independently of one another, represent H or linear or branched C_1-4Alkyl, n is a number of 1 to 1,000, Y is O, S or NR²Wherein R is²As defined above, the total number of functional groups I and II in the prepolymer is 2 or more.

The invention likewise relates to a prepolymer comprising at least one group corresponding to the general formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom and A is CH₂Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2, the polymer backbone of the prepolymer containing at least one Ar-L-Ar linked aryl group, wherein L is a covalent bond, a linear or branched, saturated or unsaturated C_1-6Alkyl radical, C_5-12Cycloalkyl radical, C_4-12Aryl or heteroaryl groups or isocyanurate, allophanate, urea, biuret, uretdione, carbodiimide, or ketimine groups.

"prepolymer" in the context of the present invention is understood to be a compound having a molecular weight of at least about 300, for example at least about 500 or at least about 700, and having at least one functional group which allows the prepolymer to be included in the polymer chain. The "prepolymer" in this context of the invention may be, for example, the product of a polyaddition, polycondensation or polymerization reaction, although this is not absolutely essential. However, a "prepolymer" in the context of the present invention may likewise have a molecular weight well in excess of the ranges described above, for example greater than about 1,000, greater than about 2,000, greater than about 4,000, greater than about 6,000, greater than about 8,000, or greater than about 10,000.

In a preferred embodiment of the invention, the prepolymers of the invention have a structure that results in an inelastic, semi-rigid material after crosslinking of the prepolymers in the polycondensation reaction. If the prepolymers of the invention are used for the production of foams, more particularly for the production of component foams, the molecular structure of the prepolymers is preferably chosen such that after curing a strong compression-resistant foam is obtained. Thus, the prepolymer of the invention of the type described above preferably contains at least one aryl group (Ar) in the molecule. In a further preferred embodiment of the present invention, the prepolymer of the present invention comprises two or more aryl groups in the molecule. In a further preferred embodiment, at least 5% of the total molecular weight of the prepolymer, preferably at least 10% by weight or at least 15% by weight of the molecular weight of the prepolymer, is formed by aryl groups. For example, prepolymers containing greater than 30 wt% aryl groups are particularly suitable.

A compound comprising at least two aryl groups Ar linked by a linking structure L, wherein L is a covalent bond, a linear or branched, saturated or unsaturated C_1-6Alkyl radical, C_5-12Cycloalkyl radical, C_4-12Aryl or heteroaryl groups or groups such as isocyanurate, allophanate, urea, biuret, uretdione, carbodiimide or ketimine groups are particularly suitable bases for this type of structure on which the prepolymers of the invention are based. Particularly suitable structures are, for example, those based on polycyclic aromatic polyisocyanates, such as those obtained from polymeric MDI, or on aromatic polycondensation products, more particularly on aniline/formaldehyde resinsTo those that have been previously described.

The prepolymers of the present invention comprise at least one group corresponding to formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom, A is C_1-12Alkylene, Z and R independently of one another represent-CH₃or-CH₂-CH₃And n is 0, 1 or 2.

In a preferred embodiment of the invention, the number of groups of formula I in the prepolymers of the invention is on average greater than 1, for example greater than about 1.1, or greater than about 1.5, or greater than about 1.8 or 2 or greater, for example up to about 100 or up to about 50 or up to about 10.

In formula I, X is an optionally substituted heteroatom. Suitable heteroatoms are for example O, S or N, but especially N. Basically, the substituents of the heteroatom N are H and a linear or branched, saturated or unsaturated, optionally substituted alkyl group containing from 1 to 24 carbon atoms, or a saturated or unsaturated optionally substituted cycloalkyl group containing from 5 to 24 carbon atoms, or an optionally substituted aryl or heteroaryl group containing from 5 to 24 carbon atoms. Suitable substituents for alkyl, cycloalkyl or aryl are, for example, halogen atoms, OH, NH groups or COOH groups.

In a preferred embodiment of the invention, a is a linear alkyl group comprising 1, 2, 3 or 4 carbon atoms, more particularly 1, 2 or 3 carbon atoms.

In addition to at least one group corresponding to formula I, the prepolymers of the present invention likewise comprise at least one group corresponding to formula II:

-N(R¹)-C(O)-Y-R² (II)，

wherein R is¹Is H or straight-chain or branched, saturated or unsaturated C_1-18Alkyl radical, R²Is straight chainOr branched, saturated or unsaturated C_1-44Alkyl, or of the formula R³-(O-CHR⁴-CHR⁴)_n-Wherein R is³Is linear or branched, saturated or unsaturated C_1-44Preferably C_1-12Or C_2-8Alkylene radical, substituent R⁴Independently of one another, represent H or linear or branched C_1-4Alkyl, n is a number of 1 to 1,000, Y is O, S or NR²Wherein R is²As defined above. In a preferred embodiment of the invention, Y is O or NR²More particularly O.

At the substituent R²The prepolymer molecules of the invention have a composition which can vary on the one hand but which on the other hand is not capable of participating in a crosslinking reaction. However, according to the substituent R²Design of (1), substituent R²The different properties of the prepolymer can be influenced only and selectively. For example, such properties as hydrophobicity, water absorption or viscosity of prepolymers, water absorption and elasticity of materials produced from such prepolymers can be improved by varying the substituents R of different properties over a wide range²The "clipping" is performed.

For example, the properties of the material obtained after crosslinking of the prepolymer can be predetermined by the basic molecular structure of the prepolymer, can be largely retained without modification, or by the choice of the short-chain substituents R²For example, alkyl groups containing from 1 to about 6 carbon atoms vary only slightly. Selection of the long-chain substituents R²For example, alkyl groups containing from 7 to about 28 carbon atoms, results in a hydrophobic, reduced viscosity of the prepolymer, and a more flexible final product.

However, in a preferred embodiment of the present invention, the prepolymer of the present invention comprises a prepolymer having the general formula R³-(O-CHR⁴-CHR⁴) Substituent R of N². These substituents are compounds of the polyether type. In the formula shown, the substituent R⁴Independently of one another preferably represents H or CH₃. In a particularly preferred embodiment, any one of the two substituents is substitutedTABLE H or one substituent R⁴Represents H, another substituent R⁴Represents CH₃. The above formula can be interpreted as meaning that in the polyether chain- (O-CHR)⁴-CHR⁴) N-provided that the polyether has more than one repeating unit, that is to say N is a number greater than 1, the substituent R⁴The meaning of (a) can vary. Thus, in a preferred embodiment of the invention, such polyether chains may constitute homopolymers, statistical copolymers or block copolymers. The number of different types of monomers included in such copolymers may be, for example, up to about 5, although two three, preferably two different monomers are included in the respective copolymers.

Substituent R³Preferably a linear alkylene group containing 2 carbon atoms, or a linear or branched alkylene group containing 3, 4, 5 or 6 carbon atoms.

In a further preferred embodiment of the invention, the corresponding polyether chains are prepared from polyethylene oxide units or polypropylene oxide units or statistical or block mixtures of polyethylene oxide units and polypropylene oxide units.

Polyether chains such as these have a chain length of, for example, from 1 to about 1,000 repeating units, that is to say the parameter n represents a number from 1 to about 1,000. In a preferred embodiment of the invention, however, n represents a number from about 1 to about 20, more particularly from about 2 to about 5.

According to the invention, the total number of functional groups I and II in the prepolymer of the invention is 2 or more. The total number may be, for example, greater than about 2.1, 2.2, 2.3, 2.5, 2.8, or greater than 3. The upper limit of the total number of functional groups of I and II in the prepolymers of the invention is about 200, preferably about 50 or less, for example about 30 or about 20 or about 15 or about 10. In the context of the present invention, the total numbers mentioned represent average numbers. For example, the prepolymers of the present invention may be composed of compounds having different molecular weights and different numbers of functional groups. In this case, the total number of functional groups I and II is averaged over all compounds present in the mixture. From which an average value is derived.

In the context of the present invention, the prepolymers of the present invention contain, on average, a total of greater than about 2 groups of formula I and formula II. According to the invention, the number of functional groups corresponding to formula I and the number of functional groups corresponding to formula II are identical. In a preferred embodiment of the invention, however, the number of functional groups corresponding to formula I is greater than the number of functional groups corresponding to formula II. The ratio of functional groups of formula I to functional groups of formula II is preferably from 10: 1 to about 3: 1, more particularly from about 6: 1 to about 4: 1.

In a further preferred embodiment of the present invention, the prepolymers of the present invention comprise on average at least one urea group per molecule. The number of urea groups may be even higher, for example greater than 1, greater than 1.5 or 2 or more. The upper limit of the total number of urea groups per molecule is the same as the upper limit of the total number of functional groups corresponding to formulae I and II. However, the actual number of urea groups may be below this upper limit.

Basically, prepolymers of the type described above according to the invention can be produced in any manner in one or more reaction stages from base molecules having corresponding functional groups of the general formulae I and II.

Suitable base molecules are preferably compounds having amino or isocyanate groups, since the corresponding functional groups can be simply linked without damaging, for example, these base molecules.

Thus, in a preferred embodiment of the invention, polyisocyanates or polyamines are used as the base molecule. Examples of suitable isocyanates are the dimeric or trimeric products of the following diisocyanate compounds: 2, 4-tolylene diisocyanate (2, 4-TDI), 2, 6-tolylene diisocyanate (2, 6-TDI) or a mixture of these isomers, 2 '-diphenylmethane diisocyanate (2, 2' -MDI), 2, 4 '-diphenylmethane diisocyanate (2, 4' -MDI), 4 '-diphenylmethane diisocyanate (4, 4' -MDI), 1, 5-Naphthylene Diisocyanate (NDI), 1, 4-phenylene diisocyanate, 1, 3-Tetramethylxylylene (TMXDI), Hydrogenated MDI (HMDI), isophorone diisocyanate (IPDI), 1, 6-Hexamethylene Diisocyanate (HDI), 2-isocyanatopropylcyclohexyl isocyanate (IPCI), 2-butyl-2-ethyl 1, 5-pentylene diisocyanate (BEPDI), Lysine Diisocyanate (LDI), 1, 12-dodecyl diisocyanate, cyclohexyl-1, 3-or-1, 4-diisocyanate, 2-methyl-1, 5-pentylene diisocyanate (MPDI), and the like, for example, containing urethane, allophanate urea, biuret, uretdione, carbodiimide or ketimine groups, formed by dimerizing or trimerizing the aforementioned diisocyanates. Particularly suitable are oligomeric or polymeric isocyanate compounds, as are obtained, for example, in the production of isocyanates, or which remain as a residue in the distillation of the crude isocyanate product at the bottom of the distillation column. Examples of materials which are particularly suitable in this connection are crude MDI, which is obtainable directly from the production of MDI, and polymeric MDI which is kept in the bottom of the distillation column after the distillation of MDI from the crude MDI.

Thus, other suitable base molecules for the purposes of the present invention are the compounds of amino equivalents as described above.

Other suitable base molecules are compounds containing a number of aryl groups and amino groups in the molecule. Polycondensation products resulting from the polycondensation of formaldehyde and aniline are particularly suitable. Suitable polycondensation products have a molecular weight of, for example, from about 500 to about 100,000, more particularly, from about 2,000 to about 20,000.

In order to incorporate the individual groups corresponding to formula I into the prepolymer, the base molecule described above is reacted with a compound containing alkoxysilyl groups.

Amino compounds containing silyl groups are particularly suitable for introducing functional groups corresponding to formula I if the base molecule carries an isocyanate group for linking the functional group corresponding to formula I to the base molecule.

Examples of suitable amino compounds comprising at least one silyl group are: h₂N-(CH₂)₃-Si(O-CH₃)₃，H₂N-(CH₂)₃-Si(O-C₂H₅)₃，H₂N-CH₂-Si(O-CH₃)₃，H₂N--CH₂-Si(O-C₂H₅)₃，H₂N-(CH₂)₂-NH-(CH₂)₃-Si(O-CH₃)₃，H₂N-(CH₂)₂-NH-(CH₂)₃-Si(O-C₂H₅)₃，H₂N-(CH₂)₃-Si(CH₃)(O-CH₃)₂，H₂N-(CH₂)₃-Si(CH₃)(O-C₂H₅)₂，H₂N-CH₂-Si(CH₃)(O-CH₃)₂，H₂N-CH₂-Si(CH₃)(O-C₂H₅)₂，H₂N-(CH₂)₂-NH-(CH₂)₃-Si(CH₃)(O-CH₃)2，H₂N-(CH₂)₂-NH-(CH₂)₃-Si(CH₃)(O-C₂H₅)₂，NH(C₆H₅)-(CH₂)₃-Si(O-CH₃)₃，NH(C₆H₅)-(CH₂)₃-Si(O-C₂H₅)₃，NH(C₆H₅)-CH₂-Si(O-CH₃)₃，NH(C₆H₅)-CH₂-Si(O-C₂H₅)₃，H₂N-(CH₂)₂-NH-(CH₂)₃-Si(O-CH₃)₃，H₂N-(CH₂)₂-NH-(CH₂)₃-Si(O-C₂H₅)₃，NH(C₆H₁₁)-(CH₂)₃-Si(O-CH₃)₃，NH(C₆H₁₁)-(CH₂)₃-Si(O-C₂H₅)₃，NH(C₆H₁₁)-CH₂-Si(O-CH₃)₃，NH(C₆H₁₁)-CH₂-Si(O-C₂H₅)₃，NH(C₄H₉)-(CH₂)₃-Si(O-CH₃)₃，NH(C₄H₉)-(CH₂)₃-Si(O-C₂H₅)3，NH(C₄H₉)-CH₂-Si(O-CH₃)₃，NH(C₄H₉)-CH₂-Si(O-C₂H₅)₃，H₂N-CH(CH₃)-CH₂-Si(O-CH₃)₃，H₂N-CH₂-CH₂-O-CH₂-CH₂-Si(O-CH₃)₃，H₂N-CH₂-CH₂-NH-CH₂-CH₂-Si(O-CH₃)₃And mixtures of two or more thereof.

In addition to the aminosilanes described above, aminosilanes carrying substituents at the nitrogen atoms for linking the base molecules are also useful in the preferred embodiments of the present invention. Particularly suitable aminosilanes of this type are compounds which comprise an alkoxysilane and an amino group corresponding to formula III.

Wherein A, Z and N have already been defined, and the substituents R⁴And R⁵Independently of one another, represent an organic radical which is inert to isocyanate groups, e.g. hydrogen (R alone)⁵)、CH₃Linear or branched saturated or unsaturated C_2-22Alkyl, aryl, or heteroaryl, ether group or COOR⁴A group. An aminosilane, for example, by reacting a compound corresponding to formula IV:

H₂N-A-Si(Z)_n(OR)_3-n (IV)

the aminosilane of (a): corresponding to the general formula V:

R⁵-CH＝CH-COOR⁴ (V)

esters of unsaturated carboxylic acids, e.g. acrylic, maleic or fumaric acid esters, in the range from 0 to aboutAt 100 ℃, wherein R is⁵Represents H or COOR⁴，R⁴Are linear or branched, saturated or unsaturated alkyl groups containing from 1 to about 8 carbon atoms, or with a mixture of two or more such maleic or fumaric esters.

Particularly suitable aminosilanes are, for example, the aminosilanes already mentioned above. Particularly suitable acrylic, methacrylic, maleic or fumaric esters are, for example, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, dimethyl maleate, diethyl maleate, di-n-butyl maleate and the corresponding fumaric esters. Dimethyl maleate and diethyl maleate are particularly preferred. The production of such compounds is described, for example, in EP0596360A 1.

If an amino group-containing compound, such as an aniline/formaldehyde condensate as described above, is used as the base molecule of the present invention for producing the prepolymer of the present invention, a compound having at least one functional group capable of reacting with the amino group of the base molecule may be used to introduce a functional group corresponding to formula I. Compounds containing NCO groups are particularly suitable for this purpose.

According to the invention, suitable compounds are, for example: OCN- (CH)₂)₃-Si(O-CH₃)₃，OCN-(CH₂)₃-Si(O-C₂H₅)₃，OCN-CH₂-Si(O-CH₃)₃，OCN-CH₂-Si(O-C₂H₅)₃，OCN-(CH₂)₃-Si(CH₃)(O-CH₃)₂，OCN-(CH₂)₃-Si(CH₃)(O-C₂H₅)₂，OCN-CH₂-Si(CH₃)(O-CH₃)₂，OCN-CH₂-Si(CH₃)(O-C₂H₅)₂，OCN-CH(CH₃)-CH₂-Si(O-CH₃)₃，OCN-CH₂-CH₂-O-CH₂-CH₂-Si(O-CH₃)₃，OCN-CH(CH₃)-Si(O-CH₃)₃，OCN-CH₂-CH₂-Si(O-CH₃)₃，OCN-CH₂-CH₂-Si(O-C₂H₅)₃And mixtures of two or more thereof.

In addition to at least one group corresponding to formula I, the prepolymers of the present invention likewise comprise at least one group corresponding to formula II:

groups corresponding to formula II are not such functional groups in the sense of chemical functionality within the molecule. The term "functional groups" in the context of the present invention, such as in formula II, is meant to be interpreted to mean that it is critical that these groups act by affecting the physical properties of the material obtained from the prepolymer of the present invention.

Basically, the same mechanisms as already described for the introduction of functional groups of the formula I are suitable for the introduction of functional groups corresponding to the formula II.

The starting point is therefore preferably a base molecule comprising isocyanate groups for binding suitable reactants. Basically, suitable reactants are any substituents R as described above²Definitions, and compounds comprising corresponding functional groups for attachment to the base molecule. Functional groups suitable for attachment to the base molecule are, for example, -OH, -SH, -NH₂or-NR⁵H. In a particular embodiment of the invention, OH groups or NH are contained₂Compounds having groups as functional groups are suitable for linking the basic molecule.

Suitable reactants according to the invention are, for example, linear or branched, saturated or unsaturated, aliphatic monoalcohols, more particularly methanol, ethanol, isomers of propanol, butanol or hexanol and aliphatic alcohols containing from about 8 to about 22 carbon atoms, for example octanol, decanol, dodecanol, tetradecanol, hexadecanol or octadecanol. The fatty alcohols mentioned are obtainable, for example, by reduction of natural fatty acids, and can be used in pure formAnd in the form of their industrially useful mixtures. Straight chain monohydric alcohols, such as, in particular, those containing from about 4 to about 18 carbon atoms, are highly suitable. However, it is equally suitable to mention alcohols and C_2-4Alkoxylation products of alkylene oxides, more particularly the alkoxylation products of the mentioned alcohols with ethylene oxide or propylene oxide or mixtures thereof. The alkoxylation product may contain the alkylene oxides just mentioned in blocks and statistical distribution.

If the base molecule used is a compound containing an amino group as described above for the attachment of the functional group, the basic principles mentioned above can of course be applied equally to such a compound. In this case, a compound containing a functional group capable of becoming a covalent bond with an amino group on the base molecule may be used for introducing a functional group corresponding to the general formula II. Compounds containing isocyanate groups are particularly suitable for this purpose. Such compounds may be obtained, for example, from the OH-, SH-or NH groups mentioned above₂The blocked compounds are produced by reacting these compounds with difunctional isocyanates in equimolar amounts. The isocyanate leaving after the reaction is based on an amino group available for binding to the base molecule.

A particular embodiment of the invention is represented by a prepolymer comprising at least one group corresponding to formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom and A is CH₂Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2, the polymer backbone of the prepolymer containing at least one Ar-L-Ar linked aryl group, wherein L is a covalent bond, a linear or branched, saturated or unsaturated C_1-6Alkyl radical, C_5-12Cycloalkyl radical, C_4-12An aryl or heteroaryl group or a urethane, allophanate, urea, biuret, uretdione, carbodiimide, or ketimine group. When particularly rapid curing of the corresponding foams is important, prepolymers such as these can be used for producing componentsAnd (3) foaming. For such foams, functional groups corresponding to formula II may not be required.

The corresponding prepolymers are produced in the same manner as has already been described for the prepolymers described at the outset. Starting from the base molecule comprising isocyanate groups, the functional groups corresponding to the formula I are preferably bound to the base molecule in the form described above. Compounds based on polymeric MDI are preferably used as base molecules. The invention likewise relates to a process for producing a prepolymer as described above, in which the base molecule and the compound suitable for introducing a function corresponding to formula I and the compound suitable for introducing a function corresponding to formula II are reacted with one another.

The reaction conditions for such reactions are well known to those of ordinary skill in the art.

In a preferred embodiment of the invention, the prepolymer of the invention has a viscosity of from about 20,000 to about 1,000,000mPas, more particularly from about 50,000 to about 500,000mPas (as measured by Brookfield rotational viscometer at 25 ℃).

The prepolymers of the invention are particularly suitable for producing stable, in particular compression-resistant, component foams. For this purpose, the prepolymer is at least mixed with a blowing agent. The invention therefore likewise relates to compositions comprising at least a prepolymer of the invention or a mixture of two or more thereof, and a blowing agent or a mixture of two or more blowing agents.

Suitable blowing agents are, for example, low-boiling fluorocarbons, hydrocarbons, ethers or mixtures of two or more thereof. Fluorocarbons R124, R125, R134a, R142b, R143 and R152a, R227; pure hydrocarbons propane, butane and isobutane and dimethyl ether, either alone or in mixtures of two or more thereof, are particularly preferred. In addition, CO₂、N₂O or N₂May be present as a blowing agent. Any combination of these gases is possible. For aerosol can formulations of the composition of the invention, a foaming gas content of 5 to 40 wt.%, more particularly 5 to 20 wt.%, based on the total composition, is preferred. In generalThe content of non-compressible gas should be measured under pressure conditions such that a pressure of about 8 to 10bar is provided at 50 c based on the real space volume of the pressurized container, depending on the relevant national regulations (if such regulations exist) of the aerosol can or pressurized container.

Basically, the composition of the invention comprises the above-mentioned foaming agent or a mixture of two or more thereof, at least in an amount which allows the composition of the invention to be discharged from a corresponding container, the discharged composition being foamed without difficulty. The compositions of the present invention preferably contain a blowing agent or a mixture of two or more blowing agents in an amount of about 10 to about 25 weight percent, more particularly about 12 to about 20 weight percent.

In addition to the ingredients mentioned, the compositions of the invention may likewise comprise one or more additives.

Suitable additives are, for example, drying aids, antioxidants, flame retardants, light stabilizers, pigment dispersants, fillers, resins, waxes, plasticizers, dyes, indicator dyes, bactericides and the like.

In many cases, it is appropriate to stabilize the formulations with a moisture stabilizer to block penetrating moisture and thereby increase their shelf life. Suitable moisture stabilizers are any compounds which react with water to form groups which are inert to the reactive groups present in the formulation, but at the same time undergo only minimal changes in their molecular weight. In addition, the stabilizer must be more reactive to moisture penetrating into the formulation than the organic polymer in the formulation or the silyl group in a mixture of two or more such polymers.

In a preferred embodiment of the invention, the moisture stabilizers used are silanes such as vinylsilanes, for example vinyltrimethoxysilane, 3-vinylpropyltriethoxysilane, oxime silanes, for example methyl-O, O '-butan-2-one trioxime silane or O, O' -butan-2-one tetraoxime silane (CAS Nos. 022984-54-9 and 034206-40-1), or benzoylaminosilanes, for example bis-N-methylbenzoylamino) -methylethoxysilane (CAS Nos. 16230-35-6). According to the invention, vinylsilanes which react rapidly with water, more particularly vinyltrimethoxysilane, are preferably used as moisture stabilizers.

The formulations of the present invention, for example, comprise from about 0.01 to about 6 wt%, more particularly from about 1 to about 3 wt% of a moisture stabilizer.

Plasticizers suitable for use in the compositions of the present invention are, for example: esters, such as abietate, adipate, azelate, benzoate, butyrate, acetate, higher fatty acid esters containing from about 8 to about 44 carbon atoms, OH-functional or epoxy fatty acid esters, fatty acid esters and esters, glycolate, phosphate, linear or branched C_1-12Phthalates, propionates, sebacates, sulfonates, thiobutyrates, trimellitates, citrates and esters based on nitrocellulose and polyvinyl acetate of alcohols and mixtures of two or more thereof. The esterification products of unsymmetrical esters of dibasic aliphatic dicarboxylic acids, for example monooctyl adipate with 2-ethylhexanol (Edenol DOA, a product of Cognis Dusseldorf) are particularly suitable.

Other suitable plasticizers are pure or mixed monohydroxy, straight-chain or branched C4-16 alcohol ethers, or mixtures of two or more different ethers of such alcohols, for example dioctyl ether (product available as Cetiol OE, Cognis, Dusseldorf).

In another preferred embodiment, the di-C of a capped polyethylene glycol, such as polyethylene glycol or polypropylene glycol_1-4Alkyl ethers, more particularly dimethyl or diethyl ether of diethylene glycol or dipropylene glycol and mixtures of two or more thereof are used as plasticizers.

Diurethanes are likewise suitable plasticizers according to the invention. Diurethanes can be obtained, for example, by reacting an OH-terminated diol with a monofunctional isocyanate, the stoichiometry being selected so that substantially all free OH groups are reacted away. Any excess isocyanate is then removed from the reaction mixture, for example by distillation. An alternative method of producing diurethanes involves reacting a monohydric alcohol with a diisocyanate, and reacting all the NCO groups.

To produce the diol-based dicarbamates, diols containing from 2 to about 22 carbon atoms may be used. Examples of such diols include ethylene glycol, propylene glycol, propane-1, 2-diol, dibutylene glycol, hexylene glycol, octylene glycol or technical mixtures of hydroxy fatty alcohols containing about 14 carbon atoms, more particularly hydroxy stearyl alcohol. Linear diol mixtures, particularly those comprising about 50 wt% polypropylene glycol having an average molecular weight (Mn) of about 400 to about 6,000, more particularly greater than about 70 wt%. Diurethanes based solely on propylene glycol of the same or different average molecular weight of from about 1,000 to about 4,000 are most particularly preferred. Substantially all of the free OH groups of the diol mixture are reacted with aromatic or aliphatic monoisocyanates or mixtures thereof. Preferred monoisocyanates are phenyl isocyanate or toluene isocyanate or mixtures thereof.

To produce the diisocyanate-based diurethanes, aromatic or aliphatic diisocyanates or mixtures thereof are used. Suitable aromatic or aliphatic diisocyanates are, for example, the isocyanates, preferably Toluene Diisocyanate (TDI), as described above which are suitable for the production of the polyurethanes according to the invention. The free NCO groups of the diisocyanates react substantially completely with monohydric alcohols, preferably linear monohydric alcohols or mixtures of two or more different monohydric alcohols. Mixtures of linear monohydric alcohols are particularly suitable. Suitable monoalcohols are, for example, monoalcohols containing from 1 to about 24 carbon atoms, such as methanol, ethanol, positional isomers of propanol, butanol, pentanol, hexanol, heptanol, octanol, decanol or dodecanol, more particularly the respective 1-hydroxy compounds and mixtures of two or more thereof. So-called "technical mixtures" of alcohols and capped polyglycol ethers are likewise suitable. Alcohol mixtures comprising polypropylene glycol monoalkyl groups having an average molecular weight (Mn) of from about 200 to about 2,000 in an amount of greater than about 50% by weight, preferably greater than about 70% by weight, based on the alcohol mixture, are particularly suitable. Diisocyanate-based diurethanes in which the free NCO groups have been fully reacted with polypropylene glycol monoalkyl ethers having an average molecular weight of from about 500 to about 2,000 are particularly preferred.

The formulations of the present invention typically contain the noted plasticizers in an amount of from about 0 to about 20 weight percent.

The formulations of the present invention may additionally contain up to about 7 wt%, for example from about 0.01 to about 5 wt% of conventional antioxidants.

The formulations of the present invention may additionally contain up to about 5 wt% of an organometallic catalyst to control the rate of cure. Organometallic catalysts in the context of the present invention for controlling the rate of cure are understood to be compounds having a metal center which influences the rate of cure. Compounds containing only silyl groups are expressly not included in the cure rate controlling catalyst and are not considered to be such compounds. Suitable catalysts are, for example, organometallic compounds, such as iron or tin compounds, more particularly iron or divalent or tetravalent tin 1, 3-dicarbonyl compounds, more particularly sn (II) carboxylates or dialkyl sn (iv) dicarboxylates and corresponding dialkoxides, for example dibutyltin dilaurate, dibutyltin diacetate, dioctyltin diacetate, dibutyltin maleate, tin (II) octoate, tin (II) phenolate or divalent or tetravalent tin acetylacetonate.

The formulations of the present invention may optionally contain up to about 30 wt%, for example from about 0.1 to about 20 wt% of a filler. Suitable fillers are, for example, inorganic compounds which are inert to silyl compounds, such as chalk, ground lime, precipitated silica, pyrogenic silica, zeolites, bentonites, mineral powder, glass beads, glass powder, glass fibers and chopped strands and other inorganic fillers and organic fillers known to the person skilled in the art, more particularly short fibers or hollow plastic beads. Fillers which impart thixotropic action to the formulation, for example swellable plastics such as polyvinyl chloride, may likewise be used.

The formulations of the present invention may contain up to about 2 wt%, for example about 1 wt% of a uv stabilizer. Particularly suitable UV stabilizers are the so-called Hindered Amine Light Stabilizers (HALS). According to the invention, the formulations according to the invention may comprise uv stabilizers having silane groups, which are included in the final product during crosslinking or curing.

The products Lowilite 75 and Lowilite 77(Great Lakes, USA) are particularly suitable for this purpose.

Foam stabilizers are suitable and generally necessary additives. Other suitable additives are microbubble modulators or stabilizers or mixtures thereof. Additives commonly used to adjust foam structure are silicone based compounds. In a preferred embodiment of the present invention, liquid, crosslinkable polybutadiene, silicone oil or paraffin oil may be used as the microbubble modifier. In a preferred embodiment of the present invention, commercially available silicone stabilizers are used as the stabilizer.

The storage stability of the compositions of the invention can be enhanced, for example, by reactive silanes. Suitable reactive silanes are, for example, tetramethoxysilane, trimethoxymethylsilane or trimethoxyvinylsilane which are suitable for water trapping. The content of such compounds in the composition of the invention will not exceed 3 wt% based on the total mixture.

Other suitable additives are flame retardants. Suitable flame retardants are, for example, the usual phosphorus-containing compounds, more particularly any of the elemental phosphorus, phosphate esters or phosphonate esters, for example triethyl phosphate or trichloropropyl phosphate. These compounds have, for example, plasticizing and viscosity-regulating properties. Other suitable flame retardants are, for example, diphenylcresyl phosphate, triphenyl phosphate, dimethyl methane phosphonate and the like. In addition, chlorinated paraffins are likewise used as flame retardants. Also suitable are halogenated polyester or polyether polyols, such as commercially available brominated polyether polyols.

Other suitable additives for the purposes of the present invention are group-carrying organic polymers. Suitable organic polymers are, for example, organic polymers selected from polyurethanes, polyesters, polyamides, polyethers, polyacrylates, polymethacrylates, polystyrenes, polyolefins such as polybutadiene or polyethylene, polyvinyl esters, ethylene/alpha-olefin copolymers, styrene/butadiene copolymers and alpha-olefin/vinyl ester copolymers or mixtures of two or more thereof.

Polyurethanes in the context of the present invention are understood to be compounds which comprise at least two urethane groups in the polymer backbone. Suitable polyurethanes can be produced, for example, using the following structural components:

at least one polyol compound selected from the group consisting of,

at least one polyisocyanate,

at least one alkoxysilane corresponding to formula VI:

Y-X-A-Si(Z)_n(OR)_3-n (VI)，

wherein Y is a substituent comprising at least one reactive isocyanate functional group, such as at least one OH, SH or NH group, provided that the polymer to be provided with the functional group I comprises a group reactive with such a functional group, or comprises at least one group reactive with an OH group or an NH group, such as at least one NCO group, provided that the polymer to be provided with the functional group I comprises a group reactive with an NCO group, X is a heteroatom, A is CH₂Z and R independently of one another represent CH₃Or CH₂-CH₃And n is 0, 1 or 2.

Where appropriate, up to about 20% by weight, based on the weight of the polyurethane, of a chain extender (structuring composition) may optionally additionally be used.

Structural component (a) may be selected from OH-terminated polyols or polyol mixtures well known to those of ordinary skill in the polyurethane production art, commonly used in the production of polyurethanes. According to the invention, it is possible to use polyols selected from polyether polyols, polyester polyols, polyetherester polyols, polyalkylene glycols, polycarbonates or polyacetals containing 2, 3, 4 or more OH groups or mixtures of two or more thereof.

The polyhydroxy compounds mentioned and their production are known in the prior art. For example, polyester polyols can be produced by the reaction of dicarboxylic acids with diols or with higher polyols or with mixtures of diols and higher polyols or with an excess of diols or higher polyols or mixtures thereof, and can be produced by ring opening of epoxidized esters, such as epoxidized fatty acid esters, with alcohols. Polycaprolactone diols, for example, obtainable from epsilon-caprolactone and diols or higher polyols are likewise suitable polyester polyols. For example, polyester polyols obtainable from low molecular weight dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, isophthalic acid, terephthalic acid or phthalic acid, or mixtures of two or more thereof, and an excess of a linear or branched, saturated or unsaturated aliphatic diol containing from about 2 to about 12 carbon atoms are useful for the purposes of the present invention. The production of polyester polyols can optionally be carried out in the presence of small amounts of higher alcohols including, for example, glycerol, trimethylolpropane, pentaerythritol or sugar alcohols such as sorbitol mannitol or glucose.

Suitable polyacetals are, for example, the polycondensation products of formaldehyde and diols or polyols or mixtures thereof in the presence of acidic catalysts.

Polyalkylene glycols such as polybutadiene glycol are commercially available products having different molecular weights. According to the invention, they are suitable, for example, as polyol components for producing the polyurethanes used in the compositions according to the invention.

Polyether polyols can be obtained, for example, by homopolymerization, copolymerization or block copolymerization of alkylene oxides, such as ethylene oxide, propylene oxide or butylene oxide, or mixtures of two or more thereof, or by reaction of polyalkylene glycols with di-or trihydric alcohols. Also suitable are the ring-opening products of the polymerization of cyclic ethers such as tetrahydrofuran with the corresponding alcohols as initiating molecules. If ester compounds such as oligo-or polyesters are used as initiating molecules, polyetherester fibers are obtained which contain ether and ester groups. According to the invention, the compounds mentioned can likewise be used as polyol components for the production of the polyurethanes used in the compositions according to the invention.

Polyols such as those obtainable by hydrogenation of di-or oligomerized fatty acids or esters thereof, castor oil, with C_1-4Epoxidized fats or oils of alkyl alcohol ring opening, C_12-18Fatty acid diethanolamine, aliphatic C_8-22Monoglycerides of fatty acids, polypropylene glycols or polysiloxanes terminated by OH groups or mixtures of two or more of the mentioned compounds can likewise be used as structural component a).

Suitable isocyanates (structural component b) are any organic compounds which contain on average more than one, more particularly two, isocyanate groups.

Preferred isocyanates are diisocyanates Q (NCO)₂Wherein Q is an aliphatic optionally substituted hydrocarbon group containing from 4 to about 12 carbon atoms, an optionally substituted cycloaliphatic hydrocarbon group containing from 6 to about 15 carbon atoms, an optionally substituted aromatic hydrocarbon group containing from 6 to about 15 carbon atoms or an optionally substituted araliphatic hydrocarbon group containing from 7 to about 15 carbon atoms. Examples of such diisocyanates are 1, 4-butylidene diisocyanate, Hexamethylene Diisocyanate (HDI), dodecamethylene diisocyanate, dimer fatty acid diisocyanate, 1, 4-diisocyanatocyclohexane, 1-isocyanato-3, 3, 5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), 4 ' -diisocyanatocyclohexylmethyl, 4 ' -diisocyanatodicyclohexyl, -2, 2-propane, 1, 3-and 1, 4-diisocyanatobenzene, 2, 4-or 2, 6-diisocyanatotoluene, (2, 4-or 2, 6-TDI) or mixtures thereof, 2 ' -, 2, 4-or 4, 4' -isocyanatodiphenylmethane (MDI), 1, 4-butylidenylxylylene diisocyanate (TMXDI), p-xylylene diisocyanate and mixtures of these compounds.

Aliphatic diisocyanates, more particularly m-and p-tetramethylxylylene diisocyanate (TMXDI) and isophorone diisocyanate (IPDI), are preferred.

More highly functional polyisocyanates known per se in polyurethane chemistry or even modified polyisocyanates known per se, such as carbodiimides, allophanate salts, isocyanurates, urethanes or biuret polyisocyanates, can of course likewise be used in part.

Chain extenders which can be used according to the invention as structural component d) for the production of polyurethanes are, for example, polyols such as ethylene glycol, propylene glycol, propane-1, 3-diol, butane-1, 4-diol, hexane-1, 6-diol, trimethylolpropane, glycerol, pentaerythritol, sorbitol, mannitol or glucose. Low molecular weight polyester diols such as succinic, glutaric or adipic acid bis- (hydroxyethyl) ester or mixtures of two or more thereof, or low molecular weight ether-containing diols such as diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol can likewise be used as structural component d). Also suitable are amines such as ethylenediamine, hexamethylenediamine, piperazine, 2, 5-dimethylpiperazine, 1-amino-3-aminomethyl-3, 5, 5-trimethylcyclohexane (isophoronediamine, IPDA), 4' -diaminodicyclohexylmethane, 1, 4-diaminocyclohexane, 1, 2-diaminopropane, hydrazine hydrate, amino acid hydrazides such as 2-glycine hydrazide or dihydrazides such as succinic dihydrazide. In the case of isocyanate polyaddition reactions, compounds having three or more functionalities may be used to obtain a certain degree of branching. As already mentioned, trifunctional or higher polyisocyanates can be used for the same purpose. Monohydric alcohols such as n-butanol or n-dodecanol and octadecanol can be used in small amounts as partial structural component d).

In the alkoxysilanes suitable as structural component c) corresponding to the general formula V, X has the meaning already defined for the general formula I. Thus, the letter X represents, for example, O, NH, NR⁵Or S, wherein R⁵Is CH₃Or a linear or branched, saturated or unsaturated alkyl group containing from 2 to about 6 carbon atoms. In a preferred embodiment of the present invention,the letter X represents O, NH or S, for example O or NH.

In the compounds corresponding to the formula V, the letter Y represents, for example, H or virtually any compound having at least one OH, SH or NH group₂A substituent of the group. In a preferred embodiment of the invention, X represents H, H₂N-(CH₂)₂、HO-C₂H₄Or (HO-C)₂H₄)₂-CH-or corresponding substituents, for example to which NCO groups can be attached, or optionally corresponding to the totality of the structural elements of the formula I in the polymer.

In the general formula II, A represents CH₂Z and R independently of one another represent-CH₃or-CH₂CH₃Is preferably-CH₃. In a preferred embodiment of the invention, the variable n is 0 or 1, preferably 0.

Examples of suitable starting materials for structural component c) are given above.

The reaction of the structural component a) can be carried out in the presence of an inert organic solvent. After the reaction the solvent is usually removed by distillation. However, polyurethanes can be conveniently produced without solvents.

For example, component b) is first reacted with component a) (polyol component) to form an NCO-terminated polyurethane prepolymer. All or only some of the NCO groups of the prepolymer are reacted with the alkoxysilane component c). The alkoxysilane-terminated polyurethane prepolymer still containing free NCO groups is adjusted in its molecular weight by adding a chain extender. Other methods for producing the polyurethanes of the present invention are well known to those of ordinary skill in the art.

The first stage reaction temperature is generally from about 5 to about 160 deg.C, preferably from about 50 to about 120 deg.C. The reaction of the prepolymer with the alkoxysilane is carried out at a temperature of from about 50 to about 120 c, for example from about 70 to about 90 c.

In a further preferred embodiment of the present invention, polyester polyols or polycarbonate polyols are used as organic polymers. Suitable polyester or polycarbonate polyols are any polyester or polycarbonate polyols, preferably polyester or polycarbonate diols having a molecular weight of at least about 200 g/mol. The production of such polyester and polycarbonate polyols is familiar to those of ordinary skill in the art.

In a further preferred embodiment of the present invention, polyethers are used as organic polymers. Polyethers suitable for use according to the present invention include suitable starter compounds such as water, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, glycerol, 1, 2, 6-hexanetriol, 1, 1, 1-trimethylolethane, trimethylolpropane, pentaerythritol, sorbitol, mannitol or alkylene oxide adducts of glucose or higher polysaccharides. A preferred embodiment of the invention is characterized in that: polyethers obtained by polyaddition of ethylene oxide or propylene oxide or mixtures thereof onto the mentioned starter compounds are used, more particularly adducts of propylene oxide. Suitable polyethers are described, for example, in EP-B0184829 and in the documents cited therein, which are part of the disclosure of the present text in connection with polyethers.

Suitable silane-terminated polyethers are therefore prepared by reaction of suitably functionalized silanes with polyether polyols. Suitable silanes are, for example, the alkoxysilane compounds already mentioned above.

In a further embodiment of the invention, polyamides are used as organic polymers. The polyamides can be obtained in a known manner by reacting dicarboxylic acids with diamines. Suitable dicarboxylic acids are, for example, the dicarboxylic acids already mentioned as being suitable for producing polyesters, more particularly dimerized fatty acids. A preferred embodiment of the invention is characterized in that: polyamides obtained by reacting dimerized fatty acids or alkyl esters thereof with alcohols containing from 1 to about 6 carbon atoms and alkylenediamines, more particularly alkylenediamines containing from 2 to about 10 carbon atoms, are used.

In the same way as described above for the polyethers or polyesters, the polyamides are provided with corresponding alkoxysilane groups.

In a further preferred embodiment of the invention polyacrylates or polymethacrylates are used as organic polymers. Polyacrylates and polymethacrylates can be obtained in a known manner by free-radically initiated polymerization of the corresponding acrylic or methacrylic esters. Suitable esters of acrylic or methacrylic acid are, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl esters. Alkoxysilane groups can be incorporated into the organic polymer, for example by polymerizing appropriately functionalized alkoxysilanes into the polymer chain, as essentially described, for example, in EP- ｃA-0818496, wherein the basic implementation of the disclosure with respect to such polymerization is considered to be part of the present text. Monomers suitable for incorporation by polymerization in the polymer chain are, for example, monomers corresponding to the general formula III, where L is a substituent having at least one ethylenically unsaturated double bond which is included in the polymer chain under the reaction conditions during the polymerization reaction.

However, the organic polymer can likewise be suitably functionalized before introducing the alkoxysilane groups and then reacted with suitably functionalized alkoxysilanes, for example alkoxysilanes corresponding to the formula III, in a polymer-analogous reaction. This can be done, for example, by polymerization, with a certain percentage of hydroxyl-functionalized acrylate or methacrylate added to the organic polymer. Monomers suitable for this purpose are, for example, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, hydroxyheptyl or hydroxyoctyl esters of acrylic or methacrylic acid.

The grafting reaction is likewise suitable for functionalizing polyacrylates or polymethacrylates with silyl groups of the general formula I. The grafting reaction is a reaction in which a graft polymer is formed. For example, when an olefinically unsaturated compound is reacted with a prepolymer, which acts as macroinitiator and thus also as grafting base, and a free radical initiator to form a graft polymer. The initiation of the reaction can be initiated, for example, by chemical or thermal cleavage of peroxide or diazo groups on the polymer chains of the graft base and exposure to light/radiation.

Polyolefins such as polyethylene comprising at least one, for example two or more, silyl groups corresponding to formula I are also suitable for the purposes of the present invention.

The silyl group containing polymers mentioned may be used in the formulations of the invention either individually or as a mixture of two or more polymers.

Other suitable organic polymers are, for example, polybutadienes obtainable by polymerizing butadiene. The butadiene can be functionalized with alkoxysilane groups in the same way as already described for polyacrylates and polymethacrylates functionalized, for example by grafting.

In a further preferred embodiment of the present invention, derivatives of aliphatic compounds, more particularly the fatty acid esters described hereinbefore, can be used as organic polymers.

The fatty compounds comprising silyl groups used in the compositions of the invention can be obtained, for example, by reacting suitably functionalized fatty compounds with castor oil, Maleic Anhydride (MA) -grafted triglycerides or epoxidized triglycerides, and suitably functionalized compounds corresponding to formula II or III.

The organic polymer used as additive in the composition according to the invention may, for example, comprise only one silyl group corresponding to formula I. However, in a preferred embodiment of the invention, the polymer comprises at least 2, for example from 2 to about 100, preferably from about 2 to about 10 silyl groups corresponding to formula II.

Suitable compositions of the invention have, for example, the following general composition:

40-80 wt% of a prepolymer

0-25 wt% of a plasticizer

0 to 30 wt% of flame retardant

0 to 5 wt% of a foam stabilizer

0-2wtwt catalyst

0-5 wt.% of other additives

1-25 wt% of a foaming gas.

Examples of formulations of the compositions of the invention for use as sealants or assembly adhesives or multipurpose adhesives are listed below:

25-90 wt% of prepolymer

0 to 50 wt% of a plasticizer

9-50 wt% of a filler

0 to 25 wt% of an additive

1-15 wt% catalyst

The compositions of the present invention can be readily converted by foaming into rigid, strong and durable component foams. The compositions of the present invention preferably have the property of forming a foam having one or more of the following properties:

A) tack free time (TAT): 5-60 minutes

B) Density: 15-200 g/l

C) Compressive stress

At 10% compression (DIN 53421): 2 to 10N/cm2

D) Curing time: 10mins-8 hours

E) Foam construction: fine to medium cell

F) Combustion characteristics (DIN 4102): fire class B2 or B3.

The compositions of the present invention can be readily produced by suitably mixing the components forming part of the composition.

The present invention therefore likewise relates to a process for producing the compositions according to the invention, in which at least one prepolymer comprises at least one group corresponding to the general formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom, A is C_1-12Alkylene, Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2,

and at least one group corresponding to formula (II):

-N(R¹)-C(O)-Y-R² (II)，

wherein R is¹Is H straight or branched, saturated or unsaturated C_1-18Alkyl radical, R²Is straight-chain or branched, saturated or unsaturated C_1-44Alkyl or of the formula R³-(O-CHR⁴-CHR⁴)_n-Wherein R is³Is linear or branched, saturated or unsaturated 1-44, preferably C_1-12Or C_2-8Alkylene radical, substituent R⁴Independently of one another, represent H or linear or branched C_1-4Alkyl, n is a number of 1 to 1,000, Y is O, S or NR²Wherein R is²As defined above, the total number of functional groups I and II in the prepolymer is 2 or more, or a mixture of two or more thereof, or

B) A prepolymer comprising at least one group corresponding to formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom and A is CH₂Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2, the polymer backbone of the prepolymer containing at least one Ar-L-Ar linked aryl group, wherein L is a covalent bond, a linear or branched, saturated or unsaturated C_1-6Alkyl radical, C_5-12Cycloalkyl radical, C_4-12Aryl radicals or heteroAryl groups or isocyanurate, allophanate, urea, biuret, uretdione, carbodiimide or ketimine groups or mixtures of two or more thereof, or mixtures of A) and B mixed with at least one blowing agent, or mixtures of two or more blowing agents.

The invention is illustrated by the following examples in which all percentages are by weight (wt%), unless otherwise stated.

Examples

Example 1

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.05g dibutyltin dilaurate was added and heated to 70 ℃ with stirring. 21.9g (0.17mol) of 2-ethylhexanol were added dropwise with stirring at 70-80 ℃. Then, 107.7g (0.33mol) of N- (3-trimethoxysilylpropyl) -aspartic acid dimethyl ester are added dropwise with stirring at 60-70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes, and 20g (10 wt%) of Mesamoll (plasticizer from Bayer) were added. No NCO groups were detected in the resulting prepolymer mixture.

Beech wood panels were partially combined with the prepolymer mixture thus produced and stored at room temperature for 7 days. The bond showed a strength of 3.1N/mm in the tensile test²。

78g of the prepolymer mixture are heated to 50 ℃ and 15g of tris (monochloroisopropyl) phosphate (flame retardant) are subsequently added. Then 1g of Tegostab B8465 (foam stabilizer), 2g of Neostan U220 (dibutyltin dipropionate from Kaneka) and 2g of GF 99 (aminosilane from Wacker) were added and the whole mixture was foamed with 20g of a blowing agent 152 a. A fine-celled, semi-rigid foam having a tack-free time of 20 minutes was obtained. The foam properties correspond to commercially available one-component aerosol PU component foams.

Example 2

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.05g dibutyltin dilaurate was added and heated to 70 ℃ with stirring. 90.1g (0.17mol) of an ethoxylated fatty alcohol (C12/C14 with 8 EO) are added dropwise with stirring at 70-80 ℃. Then, 107.7g (0.33mol) of N- (3-trimethoxysilylpropyl) -aspartic acid dimethyl ester are added dropwise with stirring at 60-70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes. No NCO groups were detected in the resulting prepolymer mixture.

Then 1g of Tegostab B8465 (foam stabilizer), 2g of Neostan U220 (dibutyltin dipropionate from Kaneka) and 2g of GF 99 (aminosilane from Wacker) were added, and then added to 93g of the prepolymer mixture at room temperature, and the whole was foamed with 20g of foaming agent 152 a. A fine-celled flexible/resilient foam with a tack-free time of 30 minutes was obtained.

Comparative example 1:

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.06g dibutyltin dilaurate was added and heated to 60 ℃ with stirring. Then, 161.5g (0.5mol) of N- (3-trimethoxysilylpropyl) -aspartic acid dimethyl ester are added dropwise with stirring at 60-70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes. No NCO groups were detected in the resulting prepolymer mixture.

74g of the prepolymer mixture were heated to 50 ℃ and 20g of tris (monochloroisopropyl) phosphate (flame retardant) and 10g of Mesamoll (plasticizer from Bayer) were subsequently added. Regardless of the amount of flame retardant and plasticizer added, the viscosity of the mixture is too high for further processing into a foamed gas foam.

Example 3

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.06g dibutyltin dilaurate was added and heated to 70 ℃ with stirring. 21.9g (0.17mol) of 2-ethylhexanol were added dropwise with stirring at 70-80 ℃. Then, 78g (0.33mol) of N-butylaminopropyltrimethoxysilane (Dynasilan 1189 from Sivento) was added dropwise with stirring at 60-70C. After the addition, the mixture was stirred at 60 ℃ for 15 minutes, and 6.7g (4 wt%) Mesamoll (plasticizer from Bayer) were added. No NCO groups were detected in the resulting prepolymer mixture.

Beech wood panels were partially combined with the prepolymer mixture thus produced and stored at room temperature for 7 days. The bond showed a strength of 2.7N/mm in the tensile test²。

78g of the prepolymer mixture are heated to 50 ℃ and 15g of tris (monochloroisopropyl) phosphate (flame retardant) are subsequently added. Then 1g of Tegostab B8465 (foam stabilizer), 2g of Neostan U220 (dibutyltin dipropionate from Kaneka) and 2g of GF 99 (aminosilane from Wacker) were added and the whole mixture was foamed with 20g of a blowing agent 152 a. A fine-celled, semi-rigid foam having a tack-free time of 20 minutes was obtained. The foam properties correspond to commercially available one-component aerosol PU component foams.

Comparative example 2:

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.06g dibutyltin dilaurate was added and heated to 60 ℃ with stirring. 117.7g (0.5mol) of N-butylaminopropyltrimethoxysilane (Dynasilan 1189 from Sivento) were added dropwise with stirring at 60-70C. After the addition, the mixture was then stirred at 60 ℃ for 15 minutes, and 7.4g (4 wt%) Mesamoll (plasticizer from Bayer) were added. No NCO groups were detected in the resulting prepolymer mixture.

77g of the prepolymer mixture are heated to 50 ℃ and 20g of tris (monochloroisopropyl) phosphate (flame retardant) are subsequently added. Regardless of the amount of flame retardant and plasticizer added, the viscosity of the mixture is too high for further processing into a foamed gas foam.

Example 4:

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.06g dibutyltin dilaurate was added and heated to 70 ℃ with stirring. 21.9g (0.17mol) of 2-ethylhexanol were added dropwise with stirring at 70-80 ℃. Then, 102.2g (0.37mol) of N-cyclohexylaminomethyltriethoxysilane was added dropwise with stirring at 60-70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes, and 13.3g (7 wt%) of Mesamoll (plasticizer from Bayer) were added. No NCO groups were detected in the resulting prepolymer mixture.

79g of the prepolymer mixture are heated to 50 ℃ and 20g of tris (monochloroisopropyl) phosphate (flame retardant) are subsequently added. At room temperature, 1g of Tegostab B8465 (foam stabilizer) was then added and the entire mixture was mixed with 20g of foaming agent 152a and foamed. A fine-celled, slightly brittle foam with a tack-free time of only 2 minutes was obtained. No additional tin or amine catalyst is necessary to form the foam.

Example 5:

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.06g dibutyltin dilaurate was added and heated to 70 ℃ with stirring. 10.9g (0.09mol) of 2-ethylhexanol were added dropwise with stirring at 70-80 ℃. Then, 127.6g (0.46mol) of N-cyclohexylaminomethyltriethoxysilane was added dropwise with stirring at 60-70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes, and 33.3g (16 wt%) of Mesamoll (plasticizer from Bayer) were added. No NCO groups were detected in the resulting prepolymer mixture.

To 99g of this prepolymer mixture, 1g of Tegostab B8465 (foam stabilizer) was then added at room temperature, and the entire mixture was mixed with 20g of foaming agent 152a and foamed. A fine-celled, rigid and slightly brittle foam with a tack-free time of less than 1 minute was obtained. No additional tin or amine catalyst is necessary to form the foam.

Example 6

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.05g dibutyltin dilaurate was added and heated to 70 ℃ with stirring. 90.1g (0.17mol) of an ethoxylated fatty alcohol (C12/C14 with 8 EO) are added dropwise with stirring at 70-80 ℃. Then, 90.9g (0.33mol) of N-cyclohexylaminomethyltriethoxysilane was added dropwise with stirring at 60-70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes. No NCO groups were detected in the resulting prepolymer mixture.

Beech wood panels were partially combined with the prepolymer mixture thus produced and stored at room temperature for 7 days. The bond showed a strength of 3.9N/mm in the tensile test (wood failure)²。

Then 1g of Tegostab B8465 (foam stabilizer), 1g of Neostan U220 (dibutyltin dipropionate from Kaneka) and 1g of GF 99 (aminosilane from Wacker) were added, and then added to 96g of the prepolymer mixture at room temperature, and the whole was foamed with 20g of foaming agent 152 a. A fine-celled, semi-rigid foam having a tack-free time of 3 minutes was obtained. The foam properties correspond to commercially available one-component aerosol PU component foams.

Example 7:

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.06g dibutyltin dilaurate was added and heated to 60 ℃ with stirring. 137.8g (0.5mol) of N-cyclohexylaminomethyltriethoxysilane and 17.1g (0.05mol) of bis- (trimethoxysilylpropyl) amine (Silquest 1170 from Crompton/OSi) were added dropwise with stirring at 60-70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes, and 41g (20 wt%) of Mesamoll (plasticizer from Bayer) were added. No NCO groups were detected in the resulting prepolymer mixture.

Beech wood panels were partially combined with the prepolymer mixture thus produced and stored at room temperature for 7 days. The bond showed a strength of 1.5N/mm in the tensile test²。

To 80g of this prepolymer mixture were then added 0.05g of Neostan U220 (dibutyltin dipropionate from Kaneka) and 1g of Tegostab B8465 (foam stabilizer), and the whole mixture was foamed with 20g of a foaming agent 152 a. Fine-celled, rigid and brittle foams with tack-free times of less than 1 minute were obtained. No additional tin or amine catalyst is necessary to form the foam.

Example 8:

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.06g dibutyltin dilaurate was added and heated to 70 ℃ with stirring. 21.9g (0.17mol) of 2-ethylhexanol were added dropwise with stirring at 70-80 ℃. Then 76.1g (0.33mol) of N-phenylaminomethyltrimethoxysilane were added dropwise with stirring at 60-70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes, and 16.6g (10 wt%) of Mesamoll (plasticizer from Bayer) were added. No NCO groups were detected in the resulting prepolymer mixture.

Beech wood panels were partially combined with the prepolymer mixture thus produced and stored at room temperature for 7 days. The bond showed a strength of 5.8N/mm in the tensile test (wood failure)²。

84g of the prepolymer mixture are heated to 50 ℃ and 15g of tris (monochloroisopropyl) phosphate (flame retardant) are subsequently added. At room temperature, 1g of Tegostab B8465 (foam stabilizer) was then added and the entire mixture was mixed with 20g of foaming agent 152a and foamed. A slightly coarse cell, flexible and resilient foam with a tack-free time of 10 minutes was obtained. No additional tin or amine catalyst is necessary to form the foam.

Example 9:

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.06g dibutyltin dilaurate was added and heated to 70 ℃ with stirring. 10.9g (0.09mol) of 2-ethylhexanol were added dropwise with stirring at 70-80 ℃. Then, 95.2g (0.41mol) of N-phenylaminomethyltrimethoxysilane was added dropwise with stirring at 60 to 70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes, and 17.4g (10 wt%) of Mesamoll (plasticizer from Bayer) were added. No NCO groups were detected in the resulting prepolymer mixture.

Beech wood panels were partially combined with the prepolymer mixture thus produced and stored at room temperature for 7 days. The bond showed a strength of 5.2N/mm in the tensile test (wood failure)²。

84g of the prepolymer mixture are heated to 50 ℃ and 15g of tris (monochloroisopropyl) phosphate (flame retardant) are subsequently added. At room temperature, 1g of Tegostab B8465 (foam stabilizer) was then added and the entire mixture was mixed with 20g of foaming agent 152a and foamed. A fine-celled foam with a tack-free time of 10 minutes was obtained. No additional tin or amine catalyst is necessary to form the foam.

Example 10

67.9g (0.5mol NCO) Desmodur VKS 70 (Polymer-MDI from Bayer) were introduced into a 500mL reaction flask equipped with a stirring, cooling and heating device, after which 0.06g dibutyltin dilaurate was added and heated to 60 ℃ with stirring. Then, 114.2g (0.5mol) of N-phenylaminomethyltrimethoxysilane was added dropwise with stirring at 60-70 ℃. After the addition, the mixture was stirred at 60 ℃ for 15 minutes, 18.3g (10 wt%) Mesamoll (plasticizer from Bayer) were added. No NCO groups were detected in the resulting prepolymer mixture.

Beech wood panels were partially combined with the prepolymer mixture thus produced and stored at room temperature for 7 days. The bond showed a strength of 3.5N/mm in the tensile test²。

84g of the prepolymer mixture are heated to 50 ℃ and 15g of tris (monochloroisopropyl) phosphate (flame retardant) are subsequently added. At room temperature, 1g of Tegostab B8465 (foam stabilizer) was then added and the entire mixture was mixed with 20g of foaming agent 152a and foamed. A fine-celled foam with a tack-free time of 5 minutes was obtained. No additional tin or amine catalyst is necessary to form the foam.

Claims (12)

1. A prepolymer comprising at least one group corresponding to formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom, A is C_1-12Alkylene, Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2,

and at least one group corresponding to formula (II):

-N(R¹)-C(O)-Y-R² (II)，

wherein R is¹Is H or straight-chain or branched, saturated or unsaturated C_1-18Alkyl radical, R²Is straight-chain or branched, saturated or unsaturated C_1-44Alkyl or of the formula R³-(O-CHR⁴-CHR⁴)_nA group of (a) wherein R³Is linear or branched, saturated or unsaturated C_1-44Alkylene radicals, substituents R⁴Independently of one another, represent H or linear or branched C_1-4Alkyl, n is a number of 1 to 1,000, Y is O, S or NR²Wherein R is²As defined above, the total number of functional groups I and II in the prepolymer is 2 or more.

2. A prepolymer as claimed in claim 1, characterised in that the polymer backbone of the prepolymer comprises at least one Ar-L-Ar linked aromatic group, wherein L is a covalent bond, a linear or branched chain, a saturated or unsaturated C_1-6Alkyl radical, C_5-12Cycloalkyl radical, C_4-12Aryl or heteroaryl or isocyanurate, allophanate, urea, biuret, uretdione, carbodiimide or ketimine groups.

3. A prepolymer as claimed in claim 1 or 2 characterised in that the molecular weight is 4,000 or less.

4. A prepolymer as claimed in claim 1 or 2 characterised by a molecular weight greater than 4,000.

5. A prepolymer as claimed in any one of claims 1 to 4 characterised in that the polymer backbone is based on polymeric MDI or aniline/formaldehyde condensates.

6. A prepolymer comprising at least one group corresponding to formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom and A is CH₂Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2, the polymer backbone of the prepolymer containing at least one Ar-L-Ar linked aryl group, wherein L is a covalent bond, a linear or branched, saturated or unsaturated C_1-6Alkyl radical, C_5-12Cycloalkyl radical, C_4-12Aryl or heteroaryl or isocyanurate, allophanate, urea, biuret, uretdione, carbodiimide or ketimine groups.

7. A prepolymer as claimed in claim 6, characterised in that the polymer backbone is based on polymeric MDI or aniline/formaldehyde condensates.

8. A composition comprising at least one prepolymer or a mixture of two or more thereof according to any one of claims 1 to 7 and a blowing agent or a mixture of two or more blowing agents.

9. A composition as claimed in claim 8, characterized in that the composition is foamable and curable to a foam having one or more of the following properties:

A) tack free time (TAT): 5-60 minutes

B) Density: 15-200 g/l

C) Compressive stress

At 10% compression (DIN 53421): 2 to 10N/cm²

D) Curing time: 10 minutes to 8 hours

E) Foam construction: fine to medium cell

F) Combustion characteristics (DIN 4102): fire class B2 or B3.

10. A process for producing a composition as claimed in any one of claims 1 to 8, characterized in that at least one prepolymer comprises at least one group corresponding to the general formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom, A is C_1-12Alkylene, Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2,

and at least one group corresponding to formula (II):

-N(R¹)-C(O)-Y-R² (II)，

wherein R is¹Is H or straight-chain or branched, saturated or unsaturated C_1-18Alkyl radical, R²Is straight-chain or branched, saturated or unsaturated C_1-44Alkyl or of the formula R³-(O-CHR⁴-CHR⁴)_nA group of (a) wherein R³Is linear or branched, saturated or unsaturated C_1-44Alkylene radicals, substituents R⁴Independently of one another, represent H or linear or branched C_1-4Alkyl, n is a number of 1 to 1,000, Y is O, S or NR²Wherein R is²As defined above, the total number of functional groups I and II in the prepolymer is 2 or more, or a mixture of two or more thereof, or

B) A prepolymer comprising at least one group corresponding to formula I:

-X-A-Si(Z)_n(OR)_3-n (I)，

wherein X is an optionally substituted heteroatom and A is CH₂Z and R independently of one another represent-CH₃or-CH₂-CH₃N is 0, 1 or 2, the polymer backbone of the prepolymer containing at least one Ar-L-Ar linked aryl group, wherein L is a covalent bond, a linear or branched, saturated or unsaturated C_1-6Alkyl radical, C_5-12Cycloalkyl radical, C_4-12Aryl or heteroaryl or isocyanurate, allophanate, urea, biuret, uretdione, carbodiimide or ketimine groups, or mixtures of two or more thereof, or foaming at least oneAn agent, or a mixture of two or more blowing agents is mixed with the mixture of A) and B.

11. Use of a composition as claimed in claim 8 or 9, or produced by a process as claimed in claim 10, as an adhesive or as a component foam.

12. An adhesive or component foam produced using the formulation as claimed in claim 8 or 9 or produced using the formulation produced by the process as claimed in claim 10.