NO750411L - - Google Patents

Abstract

Flameproof regenerated cellulose products.

Description

The present invention relates to flame-resistant regenerated cellulose products, and the distinctive feature of the products according to the invention is that they contain, as a flame-resistant compound, a compound with

where Y means 0 or S,

and R^mean independently of each other

Y = S, means R., and R2 together as well

while reaching the rest with formula

R^ means independently of one another hydrogen, methyl or ethyl and when

Y = S and R^= alkyl, R^ also means propyl or butyl,

R 4 means cyclohexyl, benzyl, a phenyl residue which is optionally substituted with a bromine atom, 1-3 chlorine atoms and/or 1-3 alkyl or olefin residues with a total of no more than 4 carbon atoms, the individual alkyl or olefin residue containing no more than 4 carbon atoms atoms, and which carries at most 3 substituents, when Y=S, R^ also means an alkyl residue with 1-12 C atoms, or

R. together with the residue R^ bound to the same nitrogen atom, optionally with a further heteroatom is connected to a 5- or 6-membered, saturated heterocyclic ring,

Z means hydrogen, methyl, ethyl or propyl,

X means a residue with formula

R. or

4 or

R^ means an alkylene residue with 2-10 C atoms, a phenylene ring and when Rg is present,

Rg and R^ are hydrogen, or

Rg together with the two neighboring -NR3 and -NR3 groups means a 2-valent residue of piperazine.

The invention also relates to a method for:: the production of flame-resistant regenerated cellulose products, and the peculiarity of . the method according to the invention is that the regenerated cellulose products are precipitated from a solution containing a compound with the above formula (I).

Preferred flame retardant regenerated cellulose products contain a flame retardant compound of formula

where Y means 0 or S,

R<1>^and R<1>2mean independently of each other as when Y = S, R'^and R<1>^together also mean the remainder with formula

R'2 means hydrogen or methyl, when Y = S and R<1>^= alkyl R<1>^ also means ethyl or propyl,

Rj.^means a phenyl residue, which is optionally substituted with a bromine atom in the para position, 1 or 2 chlorine atoms, of which at least one is in the ortho position, and/or an alkyl residue with 1 or 2 C atoms, and at most carries 2 substituents, and when Y = S, R'4 also means an alkyl radical with 1-6 C atoms or cyclohexyl,

X<1> means a residue with formula

R'4or

R<1>^means a straight-chain alkylene residue with 2-6 C atoms, a 1,4-phenylene residue, and when Rg is present,

R 8 and R 3 are hydrogen or

R'^ together with the two neighboring NR<1>3 and NR^ groups means a 2-membered residue of piperazine.

If a compound of formula (I) is used in which Y is oxygen, the flame-resistant calculated cellulose products advantageously contain as flame-resistant compound a compound of formula

in which R"4 means a phenyl radical, which is optionally substituted with

1 or 2 chlorine atoms, of which at least one is in the ortd position,

R"<2> means hydrogen,

X" means a remainder with formulas

R"4or •

with R"5 together with the two neighboring groups NR"3 and NR'^ forming a divalent residue of piperazine. Does Y oxygen further contain the flame-resistant regenerated cellulose products preferably a compound of formula

wherein R"/'4 means an ortho, meta or para-chlorophenyl residue.

If Y in the compound of formula (I) represents sulphur, the flame-resistant regenerated cellulose products advantageously contain a compound of formula in which R1n and R'' represent a residue of formula

ID ^ cl

or means together the rest with formula

R1^ means hydrogen, methyl, when R'^ means methyl or ethyl, R1~ also means ethyl,

•j a

R'4 means methyl, ethyl or a phenyl residue, which is optionally substituted with 1 or 2 chlorine atoms, at least one of which is in the ortho position and/or is substituted with a methyl residue, and which at most carries 2o substituents.

X' means a residue with formulas

a

R'. or

4a

R'i-a means 1,2 ethylene and

Rgabetyr hydrogen or

R 1 c- means together with the two adjacent NR 1 and NR,^-groups one

oa 3a ba

divalent residue of piperazine.

The flame-resistant regenerated cellulose products advantageously contain a flame-retardant compound of formula

in which R1^ means a phenyl residue, which is optionally substituted with 1 or 2 chlorine atoms, at least one of which is in the ortho position or is substituted with a methyl residue.

In the above formulas R^, R2, R3°g x preferably and independently of each other mean R'^/R<<>2'R<*>3nennv« x'«

For compounds in which Y is oxygen, R^, R<l>^'R2'R2' R3' R3 and X, X' preferably and independently of each other mean R"-^R"2'R"3 nen^v« X "." R^, R" v- R2,R'2,R"2, - N (R3) X,-N (R1 ^) X' and -N (R"3) X" jmean preferably and independently of each other -NH-R'"4.

:For compounds in which Y is sulfur, R^, R<l>^/R2'R,2'R3'R<<>3 and X, X1 preferably and independently mean R'^a/R,2a'R< *>3a°^X' , R , R', R' ■ , R_, R' R1 „ ,-N(R_) X,-N(R' )X' and -N](R' J X'

aiiiazz ^a j o oa a-means preferably and independently of each other -NH-R'^.

As alkyl residues, unless otherwise specified, naturally occurring or synthesizable primary, secondary or tertiary, straight-chain or branched are considered: Examples of such primary residues are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, undecyl, dodecyl, preferably methyl, ethyl, propyl, butyl.

^.Examples of alkylene residues are 1,2 ethylene, 1,3 propylene, tetramethylene,

hexamethylene, preferably 1,2 ethylene and hexamethylene.

. Examples of substituted phenyl radicals are 2t-,3t or 4-methylphenyl, 2t-,3 or 4-chlorophenyl, 3 or 4-bromophenyl, 2,3-,'2,4-, 2,5-, 3,4-or 3,5-dichlorophenyl, 2, 4,- 5,-trichlorophenyl, 2, 3-, 2, 4-, 2, 5T,

2, 6t,3,44, 3, 5-dimethylphenyl, 2, 4, 5-,2, 4, 6-trimethylphenyl, 2- methyl-4-bromophenyl, 3-methyl-4-bromophenyl, 2-chloro-6 -methylphenyl, 3-chloro-2-methylphenyl, 4-chloro-2-methylphenyl, 5-chloro-2-methylphenyl,

2-, 4-ethylphenyl, 2,4-diethylphenyl, 2-,3-, 4-methoxyphenyl, 3-chloro-4-methoxyphenyl, 3-chloro-6-methoxyphenyl, preferred phenyl, 2-methylphenyl, 4-chlorophenyl, 2-chlorophenyl, 3,4- and 2,5-dichlorophenyl.

For the residue -N(R 3 )R 4 , the aforementioned residues are taken into account for R 4 , since when R 4 is phenyl or substituted phenyl, R 3 preferably means hydrogen.

The substitution of the phenyl ring with bromine is preferred in the para position.

Examples of hetrocyclic rings corresponding to the formula -N(R3)R4 are the piperidino and morpholino rings.

As compounds with formula (I) come i.a. the compounds in consideration which are listed in the following listed literature places.

The conditions for the preparation of the compounds of formula (I)

are not critical.

If Y means oxygen, one proceeds as described in Houben Weyl, Methoden der organischen Chemie, 4th edition, volume 12/11, pages

465-475. Compounds in which R^ and R2 have the meaning and Y = 0 are possible for example. produce by turnover of

phosphorus oxychloride with a primary or secondary amine in the presence of an acid-binding agent and optionally in the presence of an inert solvent. A corresponding excess of the amine participating in the reaction and/or a tertiary amine, such as pyridine, can be used as an acid-binding agent. Inert solvents are e.g. benzene, toluene, chlorine and dichlorobenzene, tetrahydrofuran, diethyl ether. Analogous examples of the preparation of specific compounds are further described in the literature, e.g. in Berichte der deutschen chemischen Gesellschaft, volume 28, pages 619-620 (1895) as well as Liebig's Annalen der Chemie volume 326, pages 251-252 (1903). Thus, e.g. the connections br. 2, 3, 4, 6, 7, 8a, and 8b in the following table 1 produce

according to this form. According to the method described in Industrial and Engineering Chemistry, Process Research and Development volume 13, no. 1, pages 85-86 (1974), e.g. the compounds no. 1, 5 and 9 in the following table 1 are prepared.

In some cases it is advantageous to convert phosphorus trichloride first

in the presence of an acid-binding agent and an inert solvent with a

preferred secondary amine. A corresponding excess of the amine to be converted is advantageously used as an acid-binding agent. The phosphoric acid triamide obtained is then oxidized to phosphoric acid triamide. Examples of this manufacturing method can be found, e.g. in Zh. obshch.Khim. volume 43, no. 9, pages 1900-1903 (1973) or in the Journal of the Chemical Society, London, Page 4682 (1957).

In this way, compound no. 8 in table 1 is prepared. In the case of asymmetric phosphoric acid triamides, it is first prepared by reaction between an amine or amine hydrochloride and phosphorus oxychloride

desired phosphoric acid monoamide dichloride of formula

respectively phosphoric acid diamide monochloride with

which is then reacted with a further amine in the presence of an acid-binding agent to asymmetric phosphoric acid triamide. Examples of this can be found in Liebig<1>'s Annalen der Chemie, volume 326, pages 129-256

(1903), in Berichte der deutschen chemischen Gesellschaft 27,

pages 2572-2579 (1894) and ibid 28, pages 613-620 (1895), as well as in Zh.obshch. Kim. volumes. 30, since 3584 (1960). This allows the compounds Nos. 10 to 17 in the following tables 2 and 3 to be prepared.

The preparation of the compounds of formula (I) in which Y means

sulfur occurs according to methods known per se, e.g. as described in Houben-Weyl, Methoden der organischen Chemie, 4th edition, volume 12/11, pages 759-769 and 785-791.

Thus, e.g. the compounds in which R1 and R2 together have the meaning

and wherein Z has the above meaning, prepared by 2-chloro-2-thiono-5,5-dialkyl-1,3,2-dioxaphosphorinane

in the presence of an acid-binding agent and in many cases preferably in the presence of an inert solvent reacting with a primary or secondary amine or diamine. As an acid-binding agent, a corresponding excess of the amine that is reacted can be used, but also a tertiary amine, such as pyridine or triethylamine. As an inert release agent] can be used, e.g. benzene, toluene, tetrahydrofuran or diethyl ether. Examples of such a manufacturing method are described in the literature, e.g. in Tetrahedron, volume 20, pages 2781-2795

(1964). Thus, e.g. the compounds 18, 19,.20, 21, 25, 26,

27, 28, 29, and. 30 in the subsequent table 4 is prepared according to this cut.

In some cases it is advantageous first to bring 2-chloro-5,5-dialkyl-1,3,2-dioxaphosphorinane

in the presence of an acid-binding agent and in many cases preferably in the presence of an inert solvent for reaction with a primary or

secondary amine and then adding sulfur to the intermediate obtained. An example of this method of preparation can be found in Tetrahedron, volume 23, page 1703 (1967). Thus, e.g. compounds 22, 23, 24, 26 and 43 in the following table 4 are prepared according to this scheme.

Those compounds in which R1 and R2 are the meaning

and Y=S, allows e.g. produce by that

thiophosphoryl chloride (PSCl3) in the presence of an acid binder and in many cases advantageously in the presence of an inert solvent is reacted with a primary or secondary amine. Examples of this method of production can be found in the literature, e.g. in the Journal of Organic Chemistry, volume 24, page 1420 (1959) or in Liebig<1>'s Annalen der Chemie, volume 326, pages 201-219 (1903). Thus, e.g. compounds 31, 32, 34, 35, 36, 37, 38, 41 and 44 in the subsequent table 4 are prepared according to this scheme.

In many cases, it is again advantageous to first react phosphorus trichloride in the presence of an acid-binding agent, and an inert solvent with a preferred secondary amine, and then to add sulfur to the intermediate step obtained. A corresponding excess of the amine that is converted is advantageously used as an acid-binding agent. Examples of this manufacturing method can be found e.g. in Berichte, volume 28, pages 2205-2211 (1895) or in the Journal of the American Chemical Society, volume 78, pages 976-977

(1956). Thus, e.g. compounds 39 and 40 are prepared according to this scheme. In other cases again, it is advantageous to bring corresponding amounts of phosphorus pentasulphide, ^ 2S5'°9am^- n t^1 reaction. Following this method, which is described in the Journal of the American Chemical Society, Volume 70, Pages 744-746 (1948), allows

themselves e.g. the compound 33 in Table 4 was prepared

In the case of mixed thiophosphoric acid triamides, they are first produced by reaction of an amine or amine hydrochloride and thiophosphoryl chloride thiophosphoric acid monoamide dichloride or thiophosphoric acid diamide chloride,

which is then reacted with the other amine in the presence of an acid-binding agent to give the mixed thiophosphoric acid triamide. Examples of this method can be found in Liebig's Annalen der Chemie, volume 326,

pages 201-258 (1903) as well as in volume 625, pages 92-94 X1959). Thus, e.g. compound 42 in table 4 is prepared according to this procedure.

For the production of the fireproof regenerated cellulose

product, cellulose is brought into solution in a manner known per se,

e.g. in that it is transferred in a soluble derivative, e.g. by means of tetraminecopper-(Tl) hydroxide or by means of the Xanthogenate method.

A compound of formula (I) is added to the thus prepared cellulose solution. This addition can be made continuously or discontinuously immediately by intensive stirring of the cellulose solution. However, it is also possible to first disperse the compounds of formula (I) thawed in water and add them as an aqueous dispersion to the cellulose solution. In all cases, it may be advantageous to add common dispersion stabilizers and dispersants. However, you can also dissolve and add the flame-retardant compounds in a suitable solvent. Apart from the flame protection, the technically important properties of the precipitated regenerated cellulose are only insignificantly affected by the addition of the reaction products. Based on the aécellulose, one can e.g. distribute 5 to 35% by weight of the reaction products in the cellulose solution. amounts of 12-25% by weight are preferably used. From the cellulose solution, which contains these reaction products, the cellulose regenerate is precipitated in a manner known per se during shaping. As a shaping measure, the formation of threads and foils by introducing the cellulose solution into a precipitation bath, using fine nozzles or slits, comes into consideration. You can thereby use the precipitation baths common in the production of cellulose regenerated threads or foils. Thereby enclosing flame retardant • turnover products that are contained in the cellulose solution to a large extent in the precipitated cellulose regenerated material. It is also possible to use other flame retardant substances in addition to a compound of formula I. Such compounds are e.g. the reaction products of a phosphonitrile chloride with glycols, e.g. neopentyl glycol or analogous compounds, such as e.g. described in German specification 2,316,959, or cyclo-diphosphazanes, respectively thionocyclodiphosphazanes with the general formula

where Y means oxygen or sulphur,

Rg means cyclohexyl, a phenyl residue, which is optionally substituted with 1-3 chlorine atoms, 1 bromine atom in the para position and/or 1-3 alkyl or carboxylic acid residues with 1-4 carbon atoms each with a total of at most 4 carbon atoms and the phenyl residue at most carries 3 substituents, or when Y = sulphur, also methyl,

Rg means a residue of formula

R10 is hydrogen or an alkyl radical with 1-4 C atoms, R11 is an alkyl radical with 1-12 C atoms, cyclohexyl, a phenyl radical, which is optionally substituted with 1-3 chlorine atoms, a bromine atom in the para position and/or 1 -3 alkyl or olefin residues with 1-4 C atoms each with a total of at most 4 C atoms and the phenyl residue carries at most 3 substituents, or <R>10 and

R^ together with the common nitrogen atom, optionally with an additional heteroatom, forms a saturated 5- or 6-membered heterocyclic ring,

when at the same time Y means oxygen, R^q means hydrogen and Rg means phenyl or substituted phenyl, R^ means only a possibly substituted phenyl residue.,

as described in Swiss Patent Application No. 15814/73.

The amount of these additional components may vary within wide limits and may constitute up to 90% of the total amount present of the flame retardant composition. It is preferred to use 10 - 70%, especially 15 - 60% of the reaction product between phosphoronitrile chloride and glycol or a cyclodiphosphazane, respectively -t:iono-cyclodiphosphazane calculated on the total amount of the flame retardant combination present, the latter corresponding to the amounts already indicated above .

In the following examples, all parts mean parts by weight and the percentages mean percentage by weight.

Production of flame-resistant regenerated cellulose.

EXAMPLE 1

Into 200 parts of a xanthogenate-based cellulose solution, which contains 18 parts oc-cellulose, 18 parts of a 20% aqueous dispersion of the flame retardant agent no. 5 in table 1 are stirred in. Such a dispersion is prepared in the following way: 15 parts of the compound no. 5 is sand-milled with 3.75 parts of a dispersant based on sodium naphthalene sulfonate and 56.25 parts of water in the presence of 75 parts of quartzite balls, working while cooling with ice at a speed of 1500 revolutions per minute. minute. After separating the quartzite balls by means of filter rings, 67 parts of a dispersion containing 20% active substance are kept. The above-described, with flame-retardant active ingredient to-

forte cellulose release, is pressed using a normal spinning process through nozzles into a precipitation bath, which per liter contains the following substances: 125 g sulfuric acid, 240 g sodium sulphate (anhydrous) and 12 g zinc sulphate (anhydrous). The obtained fibers are washed thoroughly and processed into woven fabrics. These are tested according to the method suggested by Fenimore and Martin (See ModernPlastics, November 1966) by determining the limit oxygen value (LOI) of their flame safety.

In an analogous way, flame-resistant regenerated cellulose is prepared, which

contains flame retardant active substance in the form of compound no. 1, 2,

4, 6, 7, 8, 8a, 8b, 9, 14 or 16 in tables 1-3 or a combination of these.

EXAMPLE 2

Proceed as in example 1, but use compound no. 33 from table 4 as flame retardant. In an analogous way, flame-resistant regenerated cellulose is prepared, which contains one or more of the compounds with formula no. 18, 19, 20, 21, 22, 30, 31, 32, 34, 35, 36, 37, 38, 42, 43 and 44 from table 4 as active substance.

EXAMPLE 3

In 200 parts of a cellulose solution on a xanthogenate basis, which contains 18 parts α-cellulose, 3.6 parts of the flame retardant active substance with formula 39 are stirred in and the mixture is processed in an analogous manner as in example 1 to fabric layers. *

In an analogous way, flame-resistant regenerated cellulose is produced, which contains the compounds of formula 26, 27, 28, 29 and 40 in table 4 as active ingredient.

EXAMPLE 4

In 200 parts of a xanthogenate-based cellulose solution, which contains 18 parts α-cellulose, 7.2 parts of a 50% solution of the flame-retardant active substance with formula 24 in table 4 in trichloroethylene are stirred. and the mixture is processed in the same way as described in example 1 into fabrics.

In an analogous way, flame-resistant regenerated cellulose is produced, which contains the compounds of formula 23, 25, 41 in Table 4 as active substances, using a 40 - 50% solution in dichloroethane.

EXAMPLE 5

In 200 parts of a cellulose solution on a xanthogenate basis, which contains

18 parts α-cellulose, stir in successively 9 parts of a 20%

aqueous dispersion of the flame retardant active substance no. 5 in table 1

and 5.1 parts of a 35% aqueous dispersion of the reaction product of oligomeric phosphoronitrile chlorides and 2,2-dimethyl-1,3-propanediol. The preparation of the dispersion of the flame retardant active substance no. 5 is described in example 1. The preparation of the dispersion of the mixture of the reaction products of oligomeric phosphoronitrile chlorides and 2,2-dimethyl-propanediol takes place in a manner known per se, e.g. as described in example 4 in German specification document 2.316.9 59. For the production and testing of the corresponding flame-resistant regenerated cellu-

lose, one proceeds analogously to example 1.

EXAMPLE 6

Into 200 parts of a xanthogenate-based cellulose solution, which contains 18 parts α-cellulose, 9 parts of a 20% water-

dig dispersion of the flame retardant active substance no. 5 in table 1 and

9 parts of a 20% aqueous dispersion of 2,4-dianilino-1,3-cyclodi-phosphazane. The preparation of the dispersion of the flame retardant active ingredient no. 5 is described in example 1.

The dispersion of 2,4-dianilino-1,3-cyclodiphosphazane is prepared on i

and known manner. For the production and testing of the corresponding flame-resistant cellulose, proceed analogously to example 1.

Claims (24)

1. Flame-resistant regenerated cellulose products, characterized in that these contain a compound with the formula as a breast-feeding-safe compound where Y means 0 or S,, and R 2 independently mean R 1 and R 2 together also the remainder with formula since when Y = S, means R^ independently means hydrogen, methyl or ethyl, and when Y = S and R^ = alkyl, R^ also means propyl or butyl R^ means cyclohexyl, benzyl, a phenyl residue, which is optionally substituted with a bromine atom, 1-3 chlorine atoms and/or 1-3 alkyl-. or olefin residues with a total of at most 4 C atoms, the individual alkyl or olefin residues containing at most 4 C atoms, and bearing at most 3 substituents, in that when Y = S, R^ also means an alkyl residue with 1-12 C- atoms, or R^ together with the residue R^ bound to the same nitrogen atom, optionally with a further heteroatom bound to a 5- or 6-membered saturated heterocyclic ring Z means hydrogen, methyl, ethyl or propyl, X means a residue with formula R4 or R^ means an alkyl radical with 2-10 C atoms, a phenylene ring and when Rg is present, R 8 and R 8 mean hydrogen or R^ together with the two neighboring -NR3 and ^IRg groups means a 2-valent residue of piperazine. 2. Cellulose products as stated in claim 1, characterized in that they contain a flame-retardant-generating compound of formula where Y means 0 or S, R<1>^ and R'2 mean independently of each other that, when Y = S, R^ and R'2 together also means the remainder by formula R'3 means hydrogen or methyl, when Y = S and R14 = alkyl, R'3 also means ethyl or propyl R'4 means a phenyl radical, which is optionally substituted with a bromine atom 1 para-position, 1 or 2 chlorine atoms and of which at least one of these is in the ortho-position, and/or an alkyl radical with 1 or 2 C atoms and carries at most 2 substituents and when Y = S, R'4 also means an alkyl residue with 1-6 C atoms or cyclohexyl X <1> means a residue of formula R'4 or RJt- means a straight chain alkylene radical of 2-6 C atoms, a 1,4 phenylene radical, and when R'6 is present, Rg and R<1>3 mean hydrogen or R'g together with the two neighboring NR<1>^ and NRg groups means a divalent residue of piperazine. 3. Cellulose products as specified in claims 1 and 2, characterized in that they contain a compound of formula in which R"^ means a phenyl residue which is optionally substituted with <1 or 2 chlorine atoms, of which the highest <y> is in the ortho-position, R^ means hydrogen, X" means a remainder with formulas R"4 or with R"g together with the two neighboring groups NR"^ and NR'g forming a divalent residue of piperazine. 4. Cellulose products as stated in claims 1-3, characterized in that they contain a compound of formula wherein R 1" 4 means one ortho-, meta- or para-chlorophenyl residue. 5. Cellulose products as specified in claims 1 and 2, characterized in that they contain a compound of formula wherein <R1> ja and R'2a means a residue of formula or means together the ester of formula R'^ means hydrogen, methyl when R' means methyl or ethyl, R'_ also means ethyl -j a R'4a means methyl, ethyl, a phenyl residue which is optionally substituted with 1 or #2 chlorine atoms, of which at least one is in the ortho position, and/or a methyl residue, and which carries at most 2 substituents X' means a residue with formulas 3 R', or 4a R' ga means 1',12-ethylene and Rga means hydrogen or R'ga together with the two neighboring groups NR <*>3a and NR^a means a divalent residue of piperazine. 6. Cellulose? products as stated in claims 1, 2 and 5, characterized in that they contain a flame-retardant-generating compound with the formula in which R'^ means a phenyl residue, which is optionally substituted with 1 or 2 chlorine atoms, at least one of which is in the ortho position, or a methyl residue 7. Cellulose products as specified in claims 1 - 4, characterized in that they contain a compound of formula 8. Cellulose products as specified in claims 1-4, characterized in that they contain a compound of formula 9. Cellulose products as stated in claims 1-4, characterized in that they contain a compound of formula 10. Cellulose products as specified in claims 1-4, characterized in that they contain a compound of formula 11. Cellulose products as specified in claims 1, 2, 5 and 6, characterized in that they contain a compound of formula 12. Cellulose products as specified in claims 1, 2, 5 and 6, characterized in that they contain a compound of formula 13. Cellulose products as stated in claims 1, 2, 5 and 6, characterized in that they contain a compound of formula 14. Cellulose products as stated in claims 1, 2, 5 and 6, characterized in that they contain a compound of formula 15. Cellulose products as stated in claims 1, 2, 5 and 6, characterized in that they contain a compound of formula 16. Cellulose products as stated in claims 1-15, characterized in that, in addition to a compound of formula (I), they further contain 10-90%, preferably 10-70% and especially 15-60% of a conversion product of phosphoronitrile chloride and neopentyl glycol, calculated on the total amount of the flame retardant substance present. 17. Cellulose^ product as stated in claim d-15, characterized in that, in addition to a compound of formula (I), they further contain 10-90%, preferably 10-70% and especially 15-60% 2,4-dianilino -1,3-cyclodiphosphate, calculated on the total amount of a flame retardant substance present. 18. Cellulose products as stated in claims 1-17, characterized in that they contain 5-35% by weight of the flame-retardant compound, calculated on α-cellulose. 19. Regenerated cellulose products as specified in claims 1-17, characterized in that they contain 12-25% by weight of the flame-retardant-generating compound, calculated on α-cellulose. 20. Cellulose products as specified in claims 1-19, characterized in that they are produced from calculated xanthogenate cellulose. 21. Process for the production of the cellulose products as set forth in claims 1-20, characterized in that these are precipitated from a solution containing a compound ■ ~~ (I) as a flame-retardant-generating substance. 22. Procedure as stated in claim 21, characterized in that the regenerated cellulose products are precipitated from a solution containing 5-35% by weight of the flame-retardant-generating substance, calculated on α-cellulose. 23. Procedure as stated in claim 21, characterized in that the cellulose products are precipitated from a solution containing 12-25% by weight of the flame-retardant-generating compound, calculated on α-cellulose. 24. Method as stated in claims 21-23, characterized in that the cellulose products are precipitated from a cellulose xanthogenate solution.