SU757518A1 - Monoesters of isohexadecenylsuccinic acid and oxyethylated epsilon-caprolactam possessing wetting and anticometic properties at spraying photoemulsions - Google Patents

Description

The invention relates to new chemical compounds, specifically to the monoesters of isohexadedenyl succinic acid and ethoxylated £ -caprolactam of the general formula:

^five

^С 1ь ^н 1 <“ ^с0 <° ^{sn gn} a) _t '^< h ^ _o) , O) cn _g soomsh

where t - 10-12, ¹⁰

having wetting and anti-comet and watering properties of photo emulsions.

These compounds can be used in film production technology as wetting agents.

Known monoglycerides alkenylamine acids of General formula:

¹ T? 'SNS.OOCH "SNONSS ,, HE,

ι. ¹ \ ^; 20

Synod where Μ-Νβ, K;

Ya-C _P N _2P '1, where η = 8-10,

2

which are the closest in structure to new compounds, exhibit a wetting and anticomme nous effect and are used as wetting agents for watering photo emulsions [1].

The disadvantages of wetting are their weak anticommetry effect and poor flowability when wetted "up" and "down", which makes these wetting unsuitable for irrigation of multi-layer systems. This is accompanied by the side formation of glycerol di- and triacylation products in an unregulated volume.

The aim of the invention is to expand the number of agents that could be used as surfactants with good wetting and anticommetant properties for irrigation of emulsion photolayers.

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This is achieved by the properties of the compounds of formula 1, obtained according to the known reaction of the formation of esters [2] by reacting £ -caprolactam ethoxylated with 10-12 moles of ethylene oxide with iso-hexadecane- ₅ succinic anhydride at 110-120 ° C and subsequent neutralization of the monoester with a solution of caustic soda according to the scheme:

CH ₉ CO

WITH

ten

CH _g COOMo,

The described compounds have a high upward wetting ability, provide excellent flowability of the emulsion over the lower layer or sublayer, and at the same time have a good anticommetic effect (see Table 1). 20

Reducing the length of the alkenyl radical to C12 and changing the length of the polyglycol chain t less than 10 or more 12 leads to a complete loss of anti-comet properties for wetting and makes them unsuitable for irrigation of ₂₃ emulsion layers. Due to the mono-functionality of ethoxylated £ -caprolactam, the formation of by-products during the synthesis of wetting agents is also excluded. The formation of monoesters of isohexadedenyl ₃₀ acid takes place unambiguously according to the above scheme.

The adsorption properties of 0.1 M aqueous solutions of the proposed wetting agents remain stable for 6 days. ₃₅

Example 1. Getting (10) - ethoxylated £ -caprolactam.

113 g (1 mol) of £ -caprolactam and 0.25 g of solid caustic soda are charged to a laboratory autoclave for oxyethylation. The mixture _{40 is} heated to 70 ° C. At this temperature, the autoclave is flushed with nitrogen and ethylene oxide vapor.

The temperature was raised to 95 ° C and under agitation starts slowly feeding a liquid ethylene oxide at a rate such that the pressures in autoclave ₄₅ Leniye did not rise above 3 atm., And the temperature did not exceed 120 C. Total fed 440 g (10 moles) of ethylene oxide . 553 g of (10) - ethoxylated £ -caprolactam are obtained.

Hydroxyl number, mg KOH / g:

Found 105.1;

Calculated 101.4.

The content of H ₂ About 0.07%, free polyethylene glycols is less than 2%.

Found,%: C 56.71; H 9.21; 9.20; N 2.49;

2.42;

’StigLMO ,,.

Calculated,%: C 56,40; H 9.98; N 2.53.

IR spectrum: 1753 cm ^-1 WITH-lactam; no band of CO-ether.

PRI mme R 2. Preparation of the monoester of isohexadedenyl succinic acid and (10) -oxyethylated £ -caprolactam.

In a flask with a stirrer, a thermometer and a reflux condenser, 55.3 g are charged,

(0.1 mol) (10) - ethoxylated £ -caprolactam and 32.2 g (0.1 mol) of isohexadedenyl succinic acid anhydride (T.p.

190-210 ° C / 5 mmHg, 1.4840-1.4860, average molecular weight 322). The reaction mass is heated to 110-120 ° C and shifted. sew at this temperature for 4 hours.

The monoester of isohexadecenyl succinic acid and (10) -oxyethylene £ caprolactam is obtained in the form of a light yellow mobile liquid. Acid number, mg KOH / g:

Found 66.0.

Calculated 64.1.

Found,%: C 69.27; 69.38; H 8.13; 8.11.

C4 ₆ H ₈ 5 140] 4.

Calculated,%: C 69.00; H 8.21.

To obtain a wetting agent, the monoester is neutralized at 20–30 ° C with a 10% aqueous solution of 4 g (0.1 mole) of caustic soda. The resulting wetting agent in the form of a 70% aqueous solution is a mobile liquid of light orange color, well soluble in water. For irrigation of photoemulsions prepare 0.1 M aqueous solution wetting, having a pH in the range of 7.0-8.5.

PRI me R 3. According to the method described in example 1, out of 113 g of £ -caprolactam, 0.25 g of caustic soda and 528 g of liquid ethylene oxide, 641 g of (12) - ethoxylated € -caprolactam are obtained.

Hydroxyl number, mg KOH / g:

Found 90.0

Calculated 87.5.

H ₂ About - 0.05%, free polyethylene glycols of 1.5%. .

Found,%: With 56.41; 58.18; H 9.22; 9.13;

N 2.07; 2.01;

C ₃₀ N ₅₉ MO ₁₃ .

Calculated,%: C 66.14; H 9.27; N 2.18.

EXAMPLE 4 According to the procedure described in Example 2, 96.3 g of a monoether of the general formula 1 (t = 12) in The form of a mobile liquid is light orange.

Acid number, mg KOH / g:

Found 60.0

Calculated 58.2.

Monoether is neutralized at 20-30 ° C 10%

solution of 4 g of sodium hydroxide.

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Example Conventional additives (tanning agent, plasticizer, etc.) are injected into the molten photographic emulsion of black-and-white film photographic materials, and the compound of Example 2 or 4 is used as a wetting agent. .

Watering is carried out extrusion or cuvette method.

When applying protective layers, sodium di-2-ethylhexyl ether is used.

10 ml of sulfoic succinic acid

0.1 M solution per 1 kg of the emulsion and decaethyleneglycol ether of isooctylphenol in the amount of

3 ml of 0.1 M solution per 1 kg of emulsion.

From the data given in table. 1 and 2, it follows that the proposed wetting agents have better wetting, adsorption and anti-comet properties than those known.

In addition, the proposed wetting agents do not have a negative effect on the photographic properties.

Table 1

Name substances Static wetting angle C = 1 "10" ³ m / l Dynamic surface tension dyn / cm at C = 1-10 “ ³ m / l Static surface tension dyn / cm Critical concentration anti-comet action aqueous solution C = = 1'10 " ³ m / l 6% aqueous solution of gelatin C = ⁼ 1> 10 " ³ m / l "way down" "up" m / l 10 ³ Prototype 45 thirty 70 38 42 1.5 Connection example 2 22 full spreading 60 32 32 1.0 Connection example 4 18 one "> 53 31 31. 1.5

table 2

Name Manifestation time Photographic properties substances min five TO Before

Known eight 40 0.68 0.06 Compound in example 2 eight 40 0.6 0.05 Connection ____ example 4 eight 40 0.64 and, 055 Formula inventions where t = 10-12,

Claims (2)

Monoesters of isohexadecenylsuccinic acid and ethoxylated £ -caprolactam of the general formula 50 £ RSN _g SN _g ) _t N possessing wetting and antikometny properties when watering photoemulsions. Sources of information taken into account in the examination 1. USSR author's certificate number 10531 Cl. From 03 On 1/38, 1955. 2. Chichibabin, A.E. Fundamentals of the Beginning of Organic Chemistry, Moscow, 1963. TsNIIPI Order 5548/14 Circulation 495. Subscription Branch of the PPP "Patent", Uzhgorod, Proektnaya str., 4