DE2642517A1 - SALT OF SECONDARY AETHERAMINE AND THEIR USE AS PREPARATION AGENTS FOR SYNTHESIS FIBERS - Google Patents

Description

Salts of secondary ether amines and their use as preparation agents for synthetic fibers

Subject of patent application P 25 55 896.7 (HOE 75 / F 3 10) are secondary ether amine acetates of the general formula

R- (O-CH-CH)

II XY R- (O-CH-CH)

I I

X Y

NH "

CH -. COO

in which R is a saturated or unsaturated alkyl radical having 7 to 24 carbon atoms, a cyclohexyl radical or an aryl radical optionally substituted by alkyl groups, X and Y a hydrogen atom or a methyl radical, where X and Y but not at the same time denote a methyl radical and η is an integer from 2 to 20 and their use as a preparation agent for synthetic fibers.

In a further development of this application, it has now been found that, in addition to the acetates, other salts are also based on the lying ether amines are suitable as a preparation agent.

The present application thus relates to compounds of the general formula

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X Y

R- (O-CH-CH) _n

₂ A R- (O-CH-CH) ^

II xy

II ⁿ

wherein R, X, Y and η have the meanings given for the formula I. and A represents the anion of an organic or inorganic acid, with the exception of the acetate ion.

Particularly suitable acids are aliphatic mono- and polycarboxylic acids with a saturated or unsaturated branched or unbranched, optionally substituted one Alkyl or cycloalkyl radical, aromatic carboxylic acids optionally substituted by alkyl groups, aliphatic and aromatic Sulfonic acids and inorganic acids.

In particular, aliphatic carboxylic acids with up to 20 carbon atoms, lower hydroxyalkylcarboxylic acids, lower ones are suitable Dicarboxylic acids, lower hydroxydicarboxylic acids, lower phenylalkylcarboxylic acids, cyclohexylcarboxylic acid, naphthyl and phenyl carboxylic acids, those in the ring one or more times by halogen, lower alkyl, lower alkoxy, nitro, carbonamide or sulfonamide Can be substituted, aliphatic sulfonic acids with up to 20 carbon atoms and possibly substituted by lower alkyl Naphthyl or benzenesulfonic acids and inorganic acids, preferably the oxa acids of phosphorus.

Examples of acids are: formic acid, propionic acid, Lauric acid, stearic acid, malonic acid, malic acid, lactic acid, phenylacetic acid, trifluoroacetic acid, benzoic acid, cetylsulfonic acid, p-Toluenesulfonic acid, sulfuric acid, hypophosphorous Acid. Less useful, but can in principle also be used, acids that have an unpleasant odor are unstable are or are able to react with the secondary ether amine, such as thioacetic acid, acrylic acid, chloroacetic acid.

809812/0476

The salts of the secondary A'theramine are converted by the corresponding secondary ether amines of the general formula

R- (O-CH-CH)

XY ^ NH III

R- (O-CH-CH) -

Il ⁿ

X Y

where R, X, Y and η have the meanings given for the formula I. have prepared with the equivalent amount of acid HA, where A has the meanings given above. It can It may be expedient to carry out the reaction with less or more than the stoichiometric amount of acid in order to improve the solubility of the products and the pH of the aqueous solutions.

The secondary a'theramines of the formula (III) used as starting compounds are obtained according to the method described in the German patent application P 25 55 895.6 process described by oxyalkylates of the formula IV

R- (O-CH-CH) -OH (IV)

Il

XY

in which R, X, Y and η have the meaning given for the formula (II), in the liquid phase with ammonia and hydrogen in the presence of hydrogenation-dehydrogenation catalysts, in particular nickel and cobalt contacts, with a gas velocity of at least 10 liters / kg oxyalkylate / h at a temperature of 150 to 250 ⁰ C and in the range of atmospheric pressure at 0.5 to 1.5 atm and discharges the water of reaction with the gas stream.

With the saturated and unsaturated alcohols, the oxyalkyl derivatives of the formula III and which form the radical R in the compounds of the formula II can be

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/ 4

act those that contain a primary, secondary or even a tertiary alcoholic group in the molecule. The alkyl radical can be straight-chain or branched and is derived from a corresponding alcohol, such as octyl alcohol, isononyl alcohol, Lauryl alcohol, isotridecyl alcohol. Oleyl alcohol, stearyl alcohol; Mixtures of these alcohols are also suitable, in particular those which are used in the hydrogenation of natural fatty acids or their esters are formed, such as tallow fatty alcohols, palm fatty alcohols and coconut fatty alcohols. Other alcohols, from from which the remainder R can be derived are those that arise in technical processes, e.g. according to the Ziegler process (Ethylene build-up process), the saturated, primary alcohols with a straight C-chain delivers up to about 24 carbon atoms, and according to the various oxo processes, the more or produce less branched alcohols. Aromatic hydroxy compounds such as phenol, naphthols, 2,4,6-tritertiary butylphenol, 4-i-Nony! Phenol, 4-i-octylphenol, 4-i-propylphenol, cresol, xylene and 4-i-dodecylphenol.

The oxalkylene group - (0-CH-CH) -

Il
XY

is preferably derived from ethylene oxide or from propylene oxide and is obtained by reacting the aforementioned alcohols and aromatic hydroxy compounds introduced with ethylene and / or propylene oxide. Mixtures of ethylene oxide can also be used and propylene oxide can be used, or one can react successively with ethylene oxide and propylene oxide.

The compounds of formula II are highly thermostable and survive texturing 230-250 ⁰ C without yellowing, although the underlying oxyethylated alcohols are appreciably volatile at temperatures below 200 ⁰ C. The secondary ether amine salts are applied to the fiber to be prepared, such as PES, PA, PAC, polyolefins in the usual way from aqueous solution or as pure products by dipping,

809812/0476

Spraying, padding or applied with gaIettes, the Requirements for filaments between 0.3 and 2.0, preferably 0.6 to 1.2%, for staple fibers 0.05 to 0.5, preferably 0.1 to 0.3%. The parameters, which can be varied in the broadest sense, such as the degree of oxethylation of the fatty alcohol oxethylate, or the carbon chain of the alkyl or alkene radical succeeds in tailoring the preparations to the respective intended use adapt, e.g. as texturing preparation for PES, as weaving titer preparation for PA filaments or as spinning-drawing and final preparation for PAC. The products can also be used as thermostable emulsifier systems for other water-soluble Lubricants (mineral oils, ester oils) can be used in fiber preparations. Usually the secondary according to the invention Amine salts used alone, but it is easily possible to combine them with other preparation components.

809812/0478 _{/ 6}

-JS-

example 1

For a texturing titer (dtex 167f32) of PES the following Preparations made:

a) DOS 2 326 966 example 1 a (as a comparison)

60 T paraffin oil (viscosity at 20 ⁰ C: 295 cP)

T oleyl alcohol + 7 AeO T coconut alkyldimethylamine oxide

b) Example Ib (DOS 2 326 966) (as a comparison) 60 T paraffin oil (as before)

T oleyl alcohol. + 7 AeO T lauryl alcohol triphosphate

c) 43 T pentaerythritol tetradecylate (as a comparison) 52 T emulsifier consisting of:

6 T oleyl alcohol +5.5 AeO 1 T POCl ₃ ~ esters of oleyl alcohol

(neutralized with NaOH) 1 T castor oil + 7.5 AeO 3 T coconut fatty acid. 8 AeO .1 TH ₂ O

d) according to the invention)

R- (Q-CH ₂ -CH ₂ ) ₅

R- (O-CH ₂ -CH ₂ )

R = coconut alkyl radical

8 AeO

NH ₂ CH ₃ - (CH ₂ ) ₁₀ -CO ₂

e) according to the invention

R- (O-CH ₂ -CH ₂ ) ₅

OH

NH ₂ CH ₃ -CH-CO ₂

R- (O-CH ₂ -CH ₂ ) ₅ ^

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f) (according to the invention)

R- (O-CH ₂ -CH ₂ -)

R = coconut alkyl radical

g) (according to the invention)

R- (OCH ₂ -CH ₂ ) ₅

R- (OCH ₂ -CH ₂ ) ₅ - ^

R = coconut alkyl radical

h) (according to the invention)

R- (0-CH ₀ -CH ₀ )

^{2 λ}

R- (OCH ₂ -CH ₂ ) ₅

R = coconut alkyl radical i) (according to the invention j

R- (OCH ₂ CH ₂ ) ₅

R- (OCH ₂ CH ₂ ) ₅ ^ R = coconut alkyl radical

809812/0476

NH ₂ H ₂ PO ₃

NH ₂ H ₂ PO ₄

The superior thermal stability and the low ¥ ergilbiang the stupefaction according to the invention is shown in the following table emerge:

Flüclitiglcext Yellowing in % a 7th 80 b 28 100 C. 4th 40 d units of the invention 2.5 30th e 3.0 30th f 2.7 30th G 0.9 10 H 0.8 15th X 1.5 15th

1} JFZ: yellowing after the test Din 6162

Example 2 -

On a PA 6 filament (11 d tex Of 16} aqueous solutions of the following products are applied with a circulation of 0.8% using a sponge and dried at 105 ⁰ C.

a> Di- (coconut fatty alkyl pentaoxethyl 3 amine laurate

b) Di- (coconut fatty alkyl-pentaoxethyl) amine lactate

c) Di- (coconut fatty alkyl-pentaoxethyl-amine benzoate

d) Di- {cocosfettalkyl-pentaöxäthyi) -amin-hypophosphit

e) Di- {cocos fettalkyl-pentaoxäthy 1) -aiain-phosphite

f) Di- {coconut-talkyl-pentaoxethyll-amine-phosphate

g) Mono-lauryl-diphosphate (K-Salz) as comparisons.

The threads prepared in this way were checked for their friction (sliding friction)

803812/0478 _ _Q _

or dynamic friction). Measurements were made in a measuring arrangement that is described in DT-OS 2 335 675.

dynamic thread / metal friction

a) b) c) d) e) f) g)

It can be seen that the already very smooth phosphoric acid ester g is exceeded by the tested amine salts in terms of sliding friction.

0.280 - 0.370 as comparison 0.245 - 0.280 0.330 - 0.385 0.210 - 0.280 0.285 - 0.350 0.320 - 0.380 0.355 - 0.425

809812/0476 -D-

ORJQfNAL JNSPECTED

Claims (6)

HOE 76 / F 230 patent claims: 1) Secondary ether amine salts of the general formula XY Ii R- (O-CH-CH). XY ^NH 2 ^A R- (O-CH-CH) _n in which R is a saturated or unsaturated alkyl radical with 7 to 24 carbon atoms, a cyclohexyl radical or an aryl radical optionally substituted by 2-lky! groups, X and Y is a hydrogen atom or a methyl radical, where X and Y is not, however, a methyl radical at the same time, η is an integer from 1 to 20 and A is the anion of an organic - except acetic acid - or inorganic acid. 2) Secondary ether amine salts according to claim 1 wherein X and Y are a Represent hydrogen atom. 3) Secondary ether amine salts according to claims 1 and 2, wherein A is the anion of an organic - except acetic acid - mono- or polycarboxylic acid with a saturated or unsaturated, branched or unbranched, optionally substituted alkyl or cycloalkyl radical of an aromatic, optionally by alkyl groups substituted carboxylic acid, an aliphatic or aromatic sulfonic acid or a Is oxo acid of phosphorus. 4-) Secondary ether amine salts according to claims 1 to 3 wherein A is the anion of the hypophosphorous acid. 5) Process for the preparation of the SaI ϊ e.secondary ether amines according to claims 1 to 4, characterized in that secondary ether amines of the general formula 809812/0476 - 11 - ORIGINAL INSPECTED X Y i I R- (O-CH-CH) R- (O-CH-CH) ι ι χ γ NH HOE 76/1 '' 2 3 where R, X, Y and η have the meaning given in claim 1, with acids HA, where A is given in claim 1 Meaning ηει ±, implements. 6) Use of the secondary .Ktheramin salts according to the claims 1 to 4 as a spin finish for synthetic fibers. 80981 2/0476