SU1190991A3 - Polyurethane composition - Google Patents

Abstract

POLYURETHANE COMPOSITION, including polyurethane and stabilizer, characterized in that, in order to prevent oxidation under the action of light and heat, as well as discoloration under the influence of nitrogen oxides contained in smoke obtained from the composition of the final product, as a stabilizer it contains a compound of the general formula OH Rj where R. and R are the same or different and are C |-C-alkyl, C y-C-cycloalkyl, methyl-substituted cyclohexyl R and R are hydrogen, methyl Cj-Cg-alkyl; 4 Cd-alkyl, cycloR, J-C-alkehexyl, (/) nyl, phenyl, methylamine phenyl C |-C4 is an alkoxy-substituted phenyl, C, (mono- or dialkyl-substituted hydroxyphenyl, styryl, benzyl or pyridyl, with P next the ratio of the components, wt.h.: D Polyurethane 100 Stabilizer 0.001-10 Priority on the grounds; 06.12.78 with R, and R2 - C -C-alkyl cyclohexyl R, and R-methyl, R C -Su-alkyl; RJ hexyl, cyclohexyl, mono- or dialktsubstituted hydroxyphenyl, pyridyl. 28.11,79. - all other substituents

Description

This invention relates to the chemistry of heat resistant, light resistant or nitrogen oxides polyurethane, and can be used in various industrial areas. The purpose of the invention is to prevent the oxidation of polyurethane under the action of light and temperature, as well as discoloration under the action of the nitrogen oxides contained in the smoke of the resulting product. The proposed stabilizer is obtained by the reaction of 2,2-alkylidene-bis- (4,6-disubstituted phenol) of the formula. where R.Rg C, -C4-alkyl, C-cycloalkyl or C.-C-methyl-substituted cycloalkyl, R „and R are hydrogen, alkyl or methyl with an esterifying reagent selected from the group comprising the compound of the formula R. - COC1 ( C0) 0 where Rj- - C -C-alkyl. C ,, -C-cycloalkyl, Cj-C-alkenyl, phenyl, Ci-C-alkyl substituted phenyl, C-alkoxy substituted phenyl, mono- or di C-C alkyl substituted hydroxyphenyl, styryl, benzyl or. Pyrid The reaction is carried out at a molar ratio of compounds of formula (II) or (III) to compound (J.) equal to 1.0 to 1.3. The proposed stabilizers are given in Table. 1. Example 1. Preparation of 1- (2-o-ci-3,5-dimethylphenyl) -1- (2-benzyl oyl sy-3,5-dimethylphenyl-2-methylpropane (compound 5 in Table 1). B - a three-necked flask equipped with a stirrer, thermomum and a dropping funnel, a solution of 2,2-isobutylidene-bis- (4,6-dimethylf 12 nol) in the amount indicated in Table 2, in a liquid mixture of 10 g (126.6 mmol) pyridine and 200 g of toluene. Maintaining the contents at 20 ° C under a dry nitrogen atmosphere, benzoyl chloride in the amount shown in Table 2 is added dropwise with vigorous stirring for 30 minutes and the mixture is stirred for 30 m The solution of the reaction mixture is then heated to 80 ° C and maintained at 80 ° C for 2 hours. The yield of the desired product is 97%. The product has 129-130 sec., and the infrared spectrum shows peaks at 3530 for Won 1735 dl) ( and 1250 and 1140 cm for s-o Example 2 The proposed stabilizers are prepared analogously to example 1 with the ratio indicated in Table 2, with a yield of the desired product 94-99%. The results of elemental analysis and the infrared absorption spectra of the stabilizers are given in table. 3. Example 4. B-stream of gaseous nitrogen 100 mas. polytetramethylene glycol having an average molecular weight of 1200 is contacted with 31.2 parts by weight. 4,4-diphenylmethane diisocyanate at 95 ° C for 90 minutes with stirring to obtain a pre-polymer having terminal isocyanate groups. Then the preliminary monomer is cooled to 15c, 236 wt. anhydrous K, K-dimethylformamide and dissolved in it, obtaining a solution of a preliminary polymer. Separately from this .2.28 mac. ethylenediamine and 0.51 ma.ch. diethylamine was dissolved in 157 May. 4. N-N-dimethylformamide anhydrous to form a solution. A solution of the pre-polymer is added to this solution at 15C to obtain a prliuretan solution having a viscosity of 7.80 P at 30 ° C, and then add the following: . The resultant thus obtained is subjected to stretching in a yarn using a conventional method of dry drawing of yarns. In addition, the same procedures are repeated, except that, instead of the proposed stabilizer, a known antioxidant and / or anti-bleach reagent acting against nitrogen oxides in the atmosphere is used to obtain comparison threads. The filaments thus obtained are subjected to the following tests with resistance and color fastness to smoke. The results obtained are listed in Table. 4 and 5. When testing light resistance, they are exposed to ultraviolet radiation in a fadeometer (discoloration meter) for 40 hours, and then their tensile strength is measured using a tensile strength tester and the strength is calculated (%) using the formula Strength to rupture after light Preservation of prrch-pr; tno; nGra; dit to the light composition Test color fastness to smoke is carried out according to a known method, the filament is exposed to atmospheric oxides of nitrogen To color. The effect on the color of the threads is expressed and determined in five classes, i.e. from class 1 (very strong color change) to class 5 (slight color change or no change) based on the gray scale of the color change. Example Analogously to example 4 prepare a polyurethane solution containing the proposed stabilizer and mix until smooth. The solution thus prepared is subjected to spinning according to the usual method of dry spinning. Next, some of these threads are washed in a bath containing 5 g / l of synthetic surfactant for 5 minutes, washed with water and dried. The yarns thus obtained are subjected to a test for determining the light resistance and a test for determining the resistance to fading under the influence of smoke, as described in Example 4. The results obtained are summarized in Table. 6. In tab. 4 - 6, the thread after drawing is used as the untreated thread, and the thread subjected to washing after drawing is used as the treated thread. Table 1

t

SNSNz

CCA-CH CH2

SNS

sn

СНз СНз СНзСНз

-sn-- sns

SNZ SNZ SNZ SNZ ONOSO-S (SNZ) s 3 T hF SNe SNZ, snz-g5 osoch 8 snz-gngg-sn-Gg gsnz ZSNz Shz 3

on9so- about

 CH3- | CH - Y VcH3 t CeHiT

SNS

Continuation of table 1

WITH%

SvNtt SNzNz / S (SNz1z he snSGSNZ CICHB) SNz (SNz / onozon about -snz 10 t SbNp SNSNznosnosnn; o; Y Svnp SNSNz

onoso-chn

17 С (СНз) з- -СНг- | C1CH C HSC2H5

he is 1 C (CH3H-rrVcH --Y y-C {CH3 18

Sis

CHj 15C (W Note. 9.6 (68.3) 1.02 120 (67.1) 220 (67.1) 9.2 (65.8) 0.98 3.20 (67.1) 12.7 ( 90.6) 1.35 The molar ratio of benzoyl chloride and phenol).

eight

Continuation of table 1

Table 2 h) d- | CNH-G - C (CH3H i9 (VTCH7. C2H5CNe ococH-ctt-cHjQH In compounds 9, 10-12 group C - 2,4,4-trimethylpentyl. In compound 4, the CdH group is the H-octyl group. 1H 21 CH 3 -0 I A I CH 2 CH 3 CH 3 CH 2 97,297,22,7 72,311,216,5 58,60,441,0 2,2-isobutylidene-bns- (4 6-dimethyl) Table 3

eleven

12

I 19099 I Continuation of table 4

-oxy-3-tert.butyl-5-methylbenzyl) anisole

2- (2-Oxy-3-tertgbutsh-1-5 methylbenzyl) - (4-methyl-6-tert-butylphenyl) terephthalate

2,2-Isobutylidene bis- (4,6-dimethylphenol)

2,2-Methylene bis (4-methyl-6-tert-butylphenol)

Not

4,4-Butylidene-bis- (Z-methyl-6-tert-butylphenol)

Also

Table 5

82.5 63.4 4 3

79.5 60.2 4

60.8 54.9 2 1

83.160,7 1 1

81.260.3 4 2

15

.Tetrakismetil-3 (3,5-di-tert-butyl-4-hydroxyphenyl) propionate methane

10 Tetrakismetil-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate methane

. sixteen ..

1190991

Continued table. five

Not

85.0 71.2 1

2

90.0 69.5 4 1

Continuation of table 6

Claims (1)

POLYURETHANE COMPOSITION, comprising polyurethane and a stabilizer, characterized in that, in order to prevent oxidation by light and heat, and also to discolor under the action of nitrogen oxides contained in the smoke obtained from the composition of the final product, it contains a compound of the general formula “as a stabilizer” 2 R2 where R ₍ and R ₂ are the same or different and are C, - C ₄ ~ alkyl, C _y -C ^ -cycloalkyl, methyl-substituted cyclohexyl | R _? and hydrogen, methyl; R ₄ - C ₂ - C _g -alkyl; R ₅ is C ₄ ~ Cg alkyl, cyclohexyl, C ₂ is C ₃ alkenyl, phenyl, methyl substituted phenyl; C, is a C4-alkoxy-substituted phenyl, C ₄ is a C / -mono- or dialkyl substituted oxyphenyl, styryl, benzyl 'or pyridyl, in the following ratio, wt.h *. Polyurethane 100 Stabilizer 0.001-10 Priority by feature; 12/06/78 at R ₍ and R _z - C ^ -C ₄ -alkyl ^ cyclohexyl; R, and R ₊ - methyl, And ₄ • C ^ -C ^ -alkyl; Ry - hexyl, cyclohexyl, C ^ - C ₄ ~ mono- or dialkyl-substituted oxyphenyl, pyridyl. 11/28/79. -all other deputies