DE1939669C3 - Hair setting products - Google Patents

Description

The present invention relates to hair setting compositions based on copolymers of 2-methyl-2-oxazoline and 2-n-propyl-2-oxazoline as a film former.

It is already known to treat human hair with film-forming substances. The goal This treatment is to set the hair, the washed hair easier to insert and against the outside To make influences, such as moisture and dust, less sensitive and thus the hairstyle a longer one To give durability.

The hair setting agents are used in two forms: once as an aqueous-alcoholic solution to fix the freshly washed hair before loading; on the other hand as propellant-containing sprayable solution (hairspray) for treating the finished hairstyle.

A good hair setting agent is required to be easy and residue-free when washing the hair wash out. Nevertheless, it should be resistant to damp weather, i.e. H. not swell or get sticky.

Furthermore, this agent should set the hair without sticking, but must not be hard and brittle will. The hair should have good elasticity so that it can be easily styled.

On the other hand, the films must have good abrasion resistance, otherwise they easily powder and after a short time lie on the hair as a gray sheen and dust the surrounding area.

Polymers such as polyvinylpyrrolidone are already used as film-forming substances in hair setting agents (German patent specification 873 891) and polymers of the acrylic acid series (German patent specification 716 197 and German Auslegeschrift 1015 193) used. However, hair that is set in this way will stick together easy, especially when exposed to humidity.

To remedy this, one has hydrophobic substances such as shellac, rosin and cyclohexanone resin added in small amounts [SÖFW 89 (3), 59 (1963), publication Haarmann and Reimer, Holzminden, "Perfume oils for hairspray"]. Such additives, however, make it easier to wash out of the fixing agent is reduced when washing the hair, and undesirable residues remain.

ίο Furthermore, attempts have been made to use the sticky - ': ° it and Hygroscopicity of the polyvinylpyrrolidones ·. · H to reduce the polymerisation of vinyl acetate.

But also hair setting agents, which are vinyl pyrmlidone-vinyl acetate copolymers as film-forming means

hold, do not yet show fully satisfactory properties.

With smaller vinyl acetate contents of the film-forming Copolymers show that the films are still sticky too much; with larger vinyl acetate contents triti

jo although the stickiness back, but then the Washability greatly deteriorated.

The teaching is already given in Belgian patent specification 708 554. Homopolymer of 2-methyl-2-oxazoline or 2-ethyl-2-oxazoline or

Copolymers of 2-methyl-2-oxazoline and 2-propyl-2-oxazoline to be used as a film former in hair setting agents. These are said to have reduced viscosities of 0.5 to 5.0.

Hair setting, which homopolymers of

Containing 2-methyl- or 2-ethyl-2-oxazoline as a film former, they can be washed out easily, but they show excessive stickiness and hygroscopicity (see tables).

If copolymers of 2-methyl- and 2-n-propyl-2-oxazoline with a reduced viscosity above 0.5 are used, films of good gloss are obtained, but hygroscopicity is still unsatisfactory, ie excessively tacky.
It has now been found that these disadvantages of the prior art can be avoided in hair setting agents based on copolymers of 2-methyl-2-oxazoline and 2-n-propyl-oxazoline as film formers, which are characterized in that the copolymer consists of 40 to 60 percent by weight, preferably

45 to 55 percent by weight of 2-methyl-2-oxazoline and 60 to 40 percent by weight, preferably 55 to 45 percent by weight of 2-n-propyl-2-oxazoline, has been prepared, a reduced viscosity of 0.1 to 0.35, preferably 0.15 to 0.25, measured in the Höppner viscometer, with a 0.5% solution at 25 "C in m-cresol, and 1 to 10 percent by weight, preferably 3 to 5 percent by weight, on average.
Even better results are achieved if the hair setting agents also contain 0.25 to 1 percent by weight of poly [1-phenyl-1-hydroxypropan] ol with a molecular weight of 600 to 700 (percentages by weight in each case based on the total solution).
The copolymers of 2-methyl-2-oxazoline and 2-n-propyl-2-oxazoline to be used according to the invention can be prepared in accordance with German patents 1,263,300.

The preparation of the poly [1-phenyl-1-hydroxypropan] ol to be used according to the invention can according to the German patents 402 996 and 870 022.

The molecular weight of the product is between 600 and 700.

Hair setting agents according to the invention show in comparison to the prior art in the treated Hair improved strength, elasticity, abrasion resistance, combability, and washability antistatic equipment. In addition, with 5 tinted and dyed hair, the color is even and the nuance is retained, moreover, its sensitivity to air humidity is significantly reduced.

The hair setting agents according to the invention can be used as a setting agent in aqueous-alcoholic solution Hair inlay. A sprayable mixture is in solutions with at least one alcohol optionally mixed with methylene chloride or 1,1,1-trichloroethane, and the usual propellants.

Suitable aqueous-alcoholic mixtures for setting agents for soaking wet Hair are mixtures of ethanol and / or propyl alcohol and / or isopropanol and water with at least 55% of the alcohols listed.

As blowing agents, the halogenated hydrocarbons known for this application are such as Monofluorotrichloromethane, difluorodichloromethane. Tetrafluorodichloromethane. Vinyl chloride alone or in a mixture as well as butane, propane and CO-, to use.

For further preparation of the hair setting agent and the spray setting agent you can Usual additives such as brighteners, dyes, spreading agents, UV absorbers and disinfectants - each Depending on the area of application —- can be added in small quantities.

In the following some exemplary assemblies are given to further explain the subject matter of the invention specified:

1. Hair setting fixer
example 1

(a) 3.0 percent by weight of a copolymer made from 50 percent by weight of 2-methyl-2-oxazo-Hn and 50 percent by weight of 2-n-propyl-2-oxazo-Hn (reduced viscosity: 0.18) *), 0.3 percent by weight Poly [1-phenyl-1-hydroxypropan] ol Molecular weight: 600, 0.3 percent by weight perfume, 27.5 percent by weight isopropyl alcohol, 27.5 percent by weight Propyl alcohol, the rest to 100% water,

(b) 5.0 weight percent of a copolymer made from 40 weight percent i-methyl-2-oxazo-Hn and 60 percent by weight of 2-n-propyl-2-oxazoline (reduced viscosity: 0.30) *), 0.5 percent by weight Poly [I-phenyl-1-hydroxy-propan] ol Molecular weight: 600, 0.3 percent by weight perfume, 55.0 percent by weight ethyl alcohol, the remainder 100% water.

2. Spray setting agent (hairspray)
Example 2

(a) I. Contents:

2.5 percent by weight of a copolymer made from 40 percent by weight of 2-methyl-2-oxazo-Hn and 60 percent by weight 2-n-propyl-2-oxazo - '"" /' / red = 0.20 *), 0.25 percent by weight of poly [1 - phenyl -1 - hydroxylpropan] ol, molecular weight: 650, 30.0 percent by weight methylene chloride, remainder 100% isopropanol,

to

35

40

45

55

60

·) Measured in the Höppler viscometer. with a 0.5% Solution at 25 "C in m-cresol.

II. Bottling:

40 percent by weight of the product, 60 percent by weight of a mixture of 50 parts of monofluorotrichloromethane and 50 parts of difluorodichloromethane:

(b) I. Contents:

10.0 percent by weight of a copolymer made from 50 percent by weight of 2-methyl-2-oxazo-Hn and 50 percent by weight of 2-n-propyl-2-oxazo-Hn (reduced viscosity: 0.20, measured in Höppler viscometer, with a 0.5% solution at 25 C in m-cresol), 1.0 percent by weight Poly [I - phenyl - 1 - hydroxypropan] ol, molecular weight : 650, 0.5 percent by weight perfume, 88.5 percent by weight isopropyl alcohol,

II. Bottling:

30 percent by weight filling material, 70 percent by weight monofluorotrichloromethane:

(C) I. Contents:

5 percent by weight of a copolymer made from 60 percent by weight of 2-methyl-2-oxazoline and 40 percent by weight of 2-n-propyl-2-oxazo-Hn (reduced viscosity: 0.22) *), 0.5 percent by weight Poly [1 - phenyl -1 - hydroxy - propan] ol, molecular weight: 600, 0.5 percent by weight perfume, 94.0 percent by weight ethanol,

II. Bottling:

40 percent by weight filling material, 60 percent by weight difluorodichloromethane.

The following comparative tests show the technical progress of hair setting agents according to Invention compared to prior art clarifies:

Commercial products with the following active ingredient components were used as comparison substances:

Commercial product a) - active ingredient component:

Copolymer from

20 percent by weight vinyl pyrrolidone,

80 percent by weight vinyl acetate.

Commercial product b) - active ingredient component:

Copolymer from

30 percent by weight vinyl pyrrolidone,

70 weight percent vinyl acetate.

Commercial product c) - active ingredient:

Copolymer from

50 percent by weight vinyl pyrrolidone,

50 percent by weight vinyl acetate.

Commercial product d) - active ingredient component:

Copolymer from

60 percent by weight vinyl pyrrolidone,

40 percent by weight vinyl acetate.

Commercial product e) - active ingredient component:

Copolymer from

70 percent by weight vinyl pyrrolidone,

30 weight percent vinyl acetate.

*) Measured in the Höppler viscometer, with a 0.5% solution at 25 ° C. in m-cresol.

939 IO

Furthermore, according to Belgian patent application 708 554, the following oxazoline polymers were used as Active ingredient components in hair setting agents investigated:

Homopolymer of

2-methyloxazoline,

2-ethyloxazoline,

2-propyloxazoline.

Copolymers of

90% 2-methyloxazoline,
10% 2-propyloxazoline,
80% 2-methyloxazoline,
20% 2-propyloxazoline,
50% 2-methyloxazoline,
50% 2-propyloxazoline.
30% 2-methyloxazoline,
70% 2-propyloxazoline.

These prior art hair setting agents have been used in the following in the cosmetic industry conventional tests compared with the substances according to the invention:

I. Tests on wig hair

Natural-colored and colored wig heads that had been pretreated in the same way were parted, half sprayed with a test approach and a standard spray, then visually and assessed manually:

1. Stickiness and hygroscopicity of the sprayed hair

The evaluation was carried out after certain time intervals (about 10 minutes) in a climatic chamber about 65% relative humidity by comparative palpation with the palm of the hand.

2. Appearance and shine of treated hair

20th

The gloss and gray haze were assessed visually before and after the moisture treatment.

40 hair with a feuige-toothed comb 20 times over combed out of dark cardboard. The amount of setting agent as well as handle and was assessed Appearance of the combed hair.

4. Washability of the hair setting agent

A total of 10 times sprayed hair was with washed with a standard shampoo. Assessment was carried out visually and manually.

IL test on the glass plate

1. Clarity, brilliance and continuity

With a scraper, 0.07 mm thick layers of lacquer are applied to glass plates allowed to air dry. The paint is then checked for clarity, gloss and continuity.

2. Hardness

The hardness is tested with a pencil of hardness H by writing on the paint and visually rated.

3. Water drop test

In the water test, a drop of water is dropped on the paint and it is indicated whether it is clear becomes opalescent or cloudy. Then let the drop of water run away and check whether now the paint has become clear, opalescent or cloudy.

4. Stickiness

In the moisture test, you wash your hands and dry your fingers well. Then you press the well-dry finger at intervals of 3 seconds again and again on the lacquer layer and determines if and when to detect a sticky wedge. Then the plate is in exposed to a humidity of about 60% for a certain period of time in a climatic chamber (about 10 minutes) and then performed the sticky wedge test again with your finger.

3. The hair setting agent can be combed out _{45 D} j _e results were in each case by 10 neutral ones

The wig head was determined at intervals by test subjects and are in the following Sprayed 10 times in total for 20 minutes, Tables I, II and III listed individually.

Table I.
Active ingredients: copolymers of vinyl pyrrolidone (VP) and vinyl acetate (VA)

Testing on wig hair

Combability

Washable wedge

Stickiness / hygroscopicity
Appearance / gloss *)

B.
VP: VA
30:70 Commercial product D.
VP: VA
M): 40 E.
VP: VA
70:30 A.
VP: VA
20:80 3 C.
VP: VA
50: M) 2 2 3 5 2 3 3 6th 3 5 5 6th 3 2 4th 2 2 Ί 2

*) The results were classified on a scale of I 6, where: 1 = very good, 2 = good, 3 = still satisfactory, 4 = satisfactory barely. 5 = bad, 6 = very bad.

continuation

A.
VP: VA

20:80

VP: VA JO: 70

Commercial product

VP: VA 50:50

VP: VA 60:40

2. Tests on the glass plate
Appearance of the paint

clarity

shine

continuity

Hardness (pencil H)

Scratch depth

Water drop test

Drop remains / becomes

Paint becomes / remains

Stickiness

Dry plate (after 24 hours) at about 60% rel. humidity (low values: strong tack.)

very good

very good

moderate

strong

cloudy
cloudy

15th

very good very good very good

small amount

opalescent cloudy

10 10

very good
very good
very good

weak

clear
clear

very good very good very good

weak

clear clear

4 4

very good very good very good

weak

clear clear

Table II

1. Testing on wig hair

Combability

Washability

Stickiness / hygroscopicity

Appearance / shine

2. Tests on the glass plate Appearance of the paint

clarity

shine

continuity Hardness (pencil H) Scratch depth Water drop test Drop remains / becomes Paint becomes / remains Stickiness Dry plate

After 24 hours (at 60% relative humidity; low number = strong Stickiness)

Active ingredient components:
Homopolymers

2-methyioxazoline

',,, "= 0.45

very good

very good

Well

weak

clear clear

2-ethyloxazoline

very good very good very good

weak

clear clear

2-propyloxazoline

"" = 0.38

very good

very good

Well

weak

clear clear

12th 13th

Copolymers (weight percent)

for comparison

2-methyl-2-propyloxazoline
90: 10%
',, ". = 0.18

very good very good very good

weak

clear clear

2-methyl-2-propyloxazoline
80: 20%
• / "1 = 0.18

very good

very good

Well

weak

clear clear

required acc. 2-methyl-2-propyloxazoline 50: 50% • / "1 = 0.18

very good very good very good

weak

clear

10

10

1- Comp. 2-methyl-2-propyloxazoline 30: 70% ./ "" = 0.18

very good

very good

Well

weak

clear clear

10 10

Hours. T. 2-methyl-2-propyloxazoline 50: 50% '"." = 0.55

very good

very good

Well

weak

clear clear

1 509611

Λ 939 669

Table III

10

Copolymer of 50 percent by weight of 2-methyl-2-oxazoline and 50 percent by weight of 2-n-propyl-2-oxazoline ('Ired ⁼ 0.18) with additions of a poly [1-phenyl-hydroxypropan] ol in the amounts indicated

Poly [ 1 - phenylhydroxy-propane j-nl molecular weight: 600

1. Test on hair of the wigs

Comb wedge Washability

Clarity / hygroscopicity .. Appearance / shine

2. Tests on the glass plate Appearance of the paint

clarity

shine

continuity

Hardness (pencil H) Scratch depth

Water drop test Drops remain / become Varnish becomes / remains

Cluckiness Dry plate

(24 hours at around 60% relative humidity)

0 cf.

very good very good very good

weak

clear clear

10 10

Weight percent
0.5 I 0.7 II

2
2
2
2 (invent
2
■>
2
1 very good
very good
very good very good
be good
very good weak weak clear
clear clear
clear 10 12th 10 12th

very good
very good
very good

weak

clear
clear

30th
30th

very good
very good
very good

weak

clear
clear

40
40

1.3 I 1.5 I 2 (for comparison)

4th
. 3
1
2 5
4th
I.
2 very good
very good
very good very good
very good
very good very
weak very
weak clear
clear clear
clear 60 80 60 80

very good very good very good

very weak

clear clear

As can be seen from a comparison of the test results in Tables I and II, the results according to the invention show active ingredient components to be used in all important tests at the same time satisfactory to very good results, while the active ingredient components according to the prior art always at least miss one of the desired properties. Most importantly, it was state-of-the-art has not yet been achieved, good tack behavior - that is, low tack is desirable - to combine with good washability. According to the invention, this is already done with a hair setting agent achieved according to the main claim, see Table II. In addition, even better results obtained with the hair setting agents according to claim 2, see Table III.

Claims (4)

i 939 669 claims: 1. Hair setting agent based on copolymers of 2-methyl-2-oxazoline and 2-n-propyl-2-oxazoline as a film former, characterized that the copolymer consists of 40 to 60 percent by weight of 2-methyl-2-oxazoline and 60 to 40 weight percent 2-n-propyl-2-oxazoline has been prepared, a reduced viscosity from 0.1 to 0.35, measured in the Höppler viscometer with a 0.5% solution 25 ° C in m-cresol, and 1 to 10 percent by weight is included in the mean. 2. Hair setting agent according to claim 1, characterized in that the copolymer of 45 to 55 percent by weight of 2-methyl-2-oxazoline and 55 to 45 percent by weight of 2-n-propyl-2-oxazoline were produced has been. 3. Hair setting agent according to claim 1 and 2, characterized in that the copolymer a reduced viscosity of 0.15 to 0.25. measured in the Höppler viscometer with a 0.5% solution at 25 C in m-cresol. 4. Hair setting agent according to claim 1 to 3, characterized in that it is also 0.1 up to 1 percent by weight of poly [1-phenyl-1-hydroxypropan] ol with the molecular weight of 6 (X) to 700 contains.