JPS58174412A - Novel acetal polymer and its preparation - Google Patents

Abstract

PURPOSE:To prepare a novel acetal polymer having novel terminal structure, and useful as an engineering resin having extremely excellent lubricity, by polymerizing formaldehyde, etc. using a compound having polysiloxane structure as a molecular weight regulator. CONSTITUTION:Formaldehyde or trioxane is homopolymerized using a compound of formula (R1 is H, alkyl or allyl; R2 is alkyl or allyl; n is 2-2,000) having polysiloxane structure, as a molecular weight regulator, or a compound selected from formaldehyde, trioxane and polyoxymethylene is copolymerized with a cyclic ether using the above described molecular weight regulator to obtain a novel polymer wherein at least one terminal of the linear polymer is blocked with the terminal group having the polysiloxane structure of the formula and the number-average molecular weight of the polymer excluding the terminal group is 10,000-500,000.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel acetal polymer, and more particularly to an acetal polymer having a novel terminal structure that has unprecedented superior lubricity and a method for producing the same.

Polyacetal is usually obtained by homopolymerizing formaldehyde or trioxane, or by copolymerizing formaldehyde or trioxane with a cyclic ether. Polyacetal obtained by homopolymerization has a hydroxyl group at the end and is unstable, so it cannot be put into practical use after converting the terminal hydroxyl group into a stable group by esterification, etherification, urethanization, etc. be done. On the other hand, polyacetal obtained by copolymerization has an unstable part consisting of repeating oxymethylene units at the end of the polymer, and after hydrolyzing the unstable part in the coexistence of a basic substance, , put into practical use.

Japanese Patent Publication No. 3J-94TJJ states that the molecular weight of a formaldehyde polymer is determined by the amounts of trace amounts of water, methanol, and formic acid present in a single polymerization system. Also, U.S. Patent No. 3.0/7. In the specification of Jl 9, alcohol.

There is a description that formaldehyde is polymerized in the coexistence of a chain transfer agent such as an ester, acid anhydride, amide, or imide.

Japanese Patent Publication No. 4T/-2/431 discloses that methylal, acetal, formic acid, etc. are added as a chain transfer agent during the copolymerization reaction of triochitin. Further, in Japanese Patent Publication No. 4T1R-291413, it is described that triochitin is copolymerized in the presence of polyether.

Tokko Akira again! Publication No. 6-Gu 41/ discloses that the terminal hydroxyl group of a formaldehyde polymer is reacted with triorganohydroxysilane to stabilize the polymer.

The present inventors have extensively studied molecular weight regulators and found that a specific compound functions not only as a good molecular regulating moiety but also as an end-blocking agent. Furthermore, as a result, we have discovered a new acetal polymer that has extremely excellent lubricity that has not been found in conventional acetal polymers.

That is, in the present invention, at least one end of the linear polymer is
General formula % Formula % (R1: selected from hydrogen, an alkyl group, and an allyl group, each of which may be - or different.

Horse: An alkyl group, an allyl group is blocked with a terminal group having a poly-siloquitin structure represented by -2 to -2, θOθ. Number average molecular weight excluding end groups.

, ′□:′ /θ, θθθ to jθθ, θθθ □
1111 This relates to a novel high molecular weight acetal polymer characterized by having No. 1111 as its main component.

Further, in the present invention, the general formula % (R1: selected from hydrogen, an alkyl group, and an allyl group) may be - or different.

Island; alkyl group, allyl group n The present invention relates to a method for producing a novel acetal polymer characterized by copolymerizing a compound selected from triochitin and polyoxymethylene with a cyclic ether.

The acetal polymer of the present invention has a friction coefficient of 0.76 to 0.
jO has a value of 11:,1. It is a thermally stable polymer with unprecedented lubricity. Excellent lubricity
It is based on the terminal structure of the acetal polymer, and at the same time the terminal structure of the acetal polymer is.

It is based on a molecular weight regulator that has a molecular weight regulating function. Therefore, it goes without saying that the acetal polymer of the present invention has a desired molecular weight.

Acetal polymers have been increasingly in demand as engineering resins in recent years, and improving the lubricity of acetal polymers has great industrial significance.

Next, the acetal polymer of the present invention will be specifically explained.

The acetal polymer of the present invention is a linear polymer with at least one end.

It is a polymer end-capped with a polysilochitin structure represented by 1 R* + 830 + n 1 and includes an acetal homopolymer and an acetal copolymer.

Acetal homopolymer is an oxymethylene unit (-
It is a polymer consisting of repeating CH, 0+, and the acetal copolymer is an oxyalkylene unit selected from oxyalkylene groups in a chain consisting of oxymethylene units, which may be the same or different. It is a polymer having a structure in which m=2 to 6) is inserted.

The insertion rate of oxyalkylene units in the acetal copolymer is 0.01 per oxymethylene unit/θ0 mole.
~10 moles, more preferably θ, /~20 moles.

The acetal polymer of the present invention is exemplified by the following structural formula.

R@R*+ 8 io Temporary CHtO piece Rs
(8)lR.

(Rs: alkyl group, allyl group R4: hydrogen, alkyl group, allyl group This indicates that b oxyalkylene units are inserted into the unit, and indicates the distribution of oxyalkylene units in the polymer. ) Among the structural formulas exemplified above, the acetal polymers represented by (1) and (2) have a hydroxyl group at the end and are unstable. Among these, the acetal homopolymer (1) is put into practical use after converting the terminal hydroxy group into a stable group by seven known methods such as esterification, etherification, and urethanization.

Further, the acetal copolymer (2) is subjected to the same treatment as the acetal homopolymer, or after the terminal unstable portions are removed by hydrolysis, it is put to practical use.

The structure of the acetal polymer of the present invention is confirmed by the following method. That is, when an acetal polymer is hydrolyzed in an acidic aqueous solution, the portion consisting of repeating oxymethylene units becomes formaldehyde, and the portion of oxyalkylene units inserted into the acetal copolymer becomes alkylene glycol. . Formaldehyde, alkylene glycol,
It is analyzed and quantified using methods such as gas chromatography and liquid chromatography.

In addition, the terminal group usually undergoes a hydrolysis reaction, resulting in a mixture of a cyclic siloxane oligomer and a linear polysiloxane.

These compounds are also analyzed and quantified by gas chromatography, liquid chromatography, etc.

The number average molecular weight of the acetal polymer of the present invention excluding the terminal groups is the same as that of ordinary high molecular weight polyacetals, but is approximately from /0,00θ! O0, θθO
The period between is adopted. The lower limit of the number average molecular weight is restricted by the moldability of the acetal polymer. The number average molecular weight of the acetal polymer is determined by method F below. That is, when the number average molecular weight is /θO9θθθ or less, osmotic pressure method,
Using the terminal group determination method, the number average molecular weight was 10θ, 0
In the case of θθ or more, the weight average molecular weight determined by the light scattering method and the gel permeability cycloatography method (G, P,
The number average molecular weight is determined by combining the elution curve obtained by method C).

Acetal polymers of the present invention include acetal homopolymers and acetal copolymers.

In the acetal copolymer, the oxyalkylene units to be inserted into the polymer mainly consisting of repeating oxymethylene units are selected from the general formula and may be the same or different. m = 2 to 6). For example, oxyethylene unit + (CH snow) sO
+, oxypropylene unit + (CH,)sO-)-oxytetramethylene unit.

C,H.

Mo(CH!)40+ -oxybutylene unit+CH鵞CHO−).

Oxyheximethylene unit + (CH,)・0+, oxyph ■ 1 Enylethylene unit mo CH, CHO+. Among these oxyalkylene units, oxyethylene units and oxytetramethylene units are particularly preferred from the viewpoint of improving the physical properties of the acetal polymer.

The terminal end of the acetal polymer of the present invention is a group having a polysilochitin structure represented by the general formula %. Here, R is selected from hydrogen, an alkyl group, and an allyl group, and may be the same or different.

Specific examples of polysiloquitin structures include polymonomethylsiloquitin and polydimethylsiloquitin.

・::・1: Examples include polydiethylsiloxane, polydibutylsiloxane, polymethylphenylsiloxane, and polydiphenylsiloxane.

Among these polysiloxane structures, bo99 methylsiloxane, polymethylphenylsiloxane, and polydiphenylsiloxane are particularly preferred from the viewpoint of both good stability and easy availability.

Further, R is selected from an alkyl group and an allyl group.

Specific examples of R snow include methyl, ethyl, butyl,
Examples include octyl, lauryl, stearyl, phenyl, p-Jtylphenyl, p-octylphenyl, p-nonylphenyl, and the like. Among these groups, from the viewpoint of improving the lubricating performance of the acetal polymer, alkyl groups, alkoxy groups, and allyl groups having 2 or more carbon atoms are preferable.

The degree of polymerization (0) of polysilochitin needs to be in the range of 2 to θθθ. In order to improve the lubricity of the polyacetal polymer, it is preferable that n is large. On the other hand, in order to maintain the mechanical properties of the acetal polymer, it is preferable that n is indicated. Based on both of these constraints, the most preferable range for n is 3! It is between OO.

The degree of polymerization (11) of polysilochitin can be determined using means such as liquid chromatography, viscosity measurement, and terminal group determination.

Next, the method for producing the acetal polymer of the present invention will be described.

The acetal polymer of the present invention has the general formula (Rs: selected from hydrogen, alkyl group, allyl group.

They may be the same or different.

R: alkyl group, allyl group n=J~2. Formaldehyde and trioxane are homopolymerized using a compound having a polysilochitin structure represented by It can be obtained by letting

The compound used as a molecular weight regulator in the present invention has a polysilochitin structure represented by the general formula % in one molecule.

It is essential that one end of the polysilochitin chain is always blocked with R1 selected from an alkyl group and an allyl group. On the other hand, the other end is hydrogen.

It is arbitrarily selected from alkyl groups, allyl groups, etc. Further, the degree of polymerization (n) of polysilochitin is 2 to 2. It is necessary to be in the range of θθ0, and it is preferable for the drama to be in the range of 3 to jOθ. An example of the structural formula is as follows.

■ ? 1 L;fig CH.

1 OH, ÷ 8 Tian - C Peng Ha These molecular weight modifiers are preferably purified by distillation, adsorption, drying, or other methods before being subjected to polymerization. Further, these molecular weight regulators can be used alone, or one or more of them can be mixed and subjected to polymerization.

In the homopolymerization of the present invention, sufficiently purified formaldehyde or triochitin is used as a starting material. Anionic polymerization catalysts are mainly used for homopolymerization of formaldehyde, and cationic polymerization catalysts are used for homopolymerization with trioquina.

In the copolymerization of the present invention, sufficiently purified formaldehyde, triochitin, and polyoxymethylene are used as starting materials. These starting materials are copolymerized with a cyclic ether using a cationic polymerization catalyst.

w of the cyclic ether to be copolymerized with these starting materials
The group of 4/ includes the general formula R@(R,: hydrogen, alkyl group, allyl site. For example, ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin, styrene oxide, oxetane, 3.j-
Examples include bis(chloromethyl)oxetane, tetrahydrofuran, and oxepane. Among these alkylene oxides, ethylene oxide is particularly preferred.

The second group of cyclic ethers has the general formula −
There are cyclic formals represented by: triethylene glycol formal, /, 4t-butanediol formal, /, j-bentanediol formal, /, 6-hequitinediol formal. Among these cyclic formals, especially ethylene glycol formal.

Diethylene glycol formal and 7.4t-butanediol formal are preferred.

The cyclic ether is used in an amount of 0.0% based on ioo parts by weight of the starting material.
03 to lOθ parts by weight, more preferably.

0.1 to 50 parts by weight are used.

The anionic polymerization catalyst and cationic polymerization catalyst used in the homopolymerization and copolymerization of the present invention are the following compounds.

A typical group of anionic polymerization catalysts is:

Alkali metals such as sodium and potassium, sodium-
Alkali metal complex compounds such as naphthalene and potassium-anthracene, alkali metal hydrides such as 9um hydride, alkaline earth metal hydrides such as calcium hydride, and sodium methoxide.

Alkali metal alkoxides such as potassium t-butoxy F, sodium caproate, stearic acid, etc. f)
Alkali metal carboxylic acid salts, alkaline earth metal salts of carboxylic acids such as caffeic acid magnesium, calcium stearate, a-butylamine.

Amines such as diethylamine, trioctylamine, and pyridine; q-class ammonium salts such as ammonium stearate, tetrabutylammonium methoxide, and dimethyldistearylammonium acetate; and phosphonium salts such as tetramethylphosphonium propionate and trimethylbenzylphosphonium ethoxide. , tributyltin chloride.

Tetravalent organic tin compounds such as diethyltin dilaurate and dibutyltin dimethoxide, fi-butyllithium.

Examples include alkyl metals such as ethylmagnesium chloride.

Examples of cationic polymerization catalysts include tin tetrachloride, tin tetrabromide, titanium tetrachloride, aluminum trichloride, zinc chloride, vanadium trichloride, antimony trifluoride, boron trifluoride, and boron trifluoride diethyl etherate.

So-called Friedel-Crafts type compounds such as boron trifluoride coordination compounds such as boron trifluoride acetic anhydrate and boron trifluoride triethylamine complex compounds, perchloric acid, and acetyl verchlorate.

Inorganic and organic acids such as hydroxyacetic acid, trichloroacetic acid, p-toluenesulfonic acid, triethyloxonium tetrafluoroborate, triphenylmethylhexafluoroantimo 4-), allyldiazonium hexafluorophosphate, allyldiazonium tetrafluoroborate, etc. Complex salt compound.

Diethylzinc, triethylaluminum,! >Alkyl metals such as ethylaluminum chloride, etc.

These anionic polymerization catalysts and cationic polymerization catalysts are used in an amount of 0.0005 to 3 parts by weight based on 700 parts by weight of the starting material. Homopolymerization or copolymerization is carried out without solvent or in an organic medium. Examples of the organic medium that can be used in the present invention include a-pentane, n-hexyl, n-hephtane, n-1, cyclohexyl,
Aliphatic hydrocarbons such as cyclopentane, aromatic hydrocarbons such as benzene, toluene, xylene, I-logenated aliphatic hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichlorethylene, chlorobenes, etc. There are halogenated aromatic hydrocarbons such as O-dichlorobenzone.These organic media may be used alone, or may be used as a mixture of two or more types.The molecular weight regulator is used in the reaction system. If used, it is uniformly dissolved or dispersed in the system.The concentration of the molecular weight regulator in the system (the concentration in the two is easily determined by experiment, depending on the requirements of the desired molecular weight of the acetal polymer). I can do things.

The reaction temperature is usually set between -20°C and 0°C, but in the case of no solvent, it is more preferably between 10°C and 10°C, and in the case of using an organic medium, it is between -70°C and 120°C. It is more preferable.

There is no particular limit on reaction time, but! It is set between seconds and 3θθ minutes.

After a predetermined time has elapsed, a polymerization terminator is added to one reaction system, and the homopolymerization or copolymerization is completed. The obtained polymer is stabilized by removing unstable ends by hydrolytic C2 or blocking unstable ends by a method such as esterification. The stabilized acetal polymer is put into practical use with the addition of a stabilizer and the like.

The features of the acetal polymer of the present invention and its production method which have been described in detail above are listed below.

(1) The acetal polymer has extremely excellent lubricity.

(2) By using a specific compound, it is possible to impart excellent lubricity to the acetal polymer.

Optional 1: Controlling the molecular weight of the polymer.

Measurement items in the following examples are as follows.

Reduced viscosity: Value measured at 60°C in a p-chlorophenol/tetrachloroethane (771 weight ratio) solution at a polymer concentration of 0.111.

Reduced viscosity is an indicator of molecular weight.

Friction coefficient: To 700 parts of a polymer that has been terminally stabilized using acetic anhydride, co, 2-methylene-bis (4t-methyl-t-t [F] "1-butylphenol) O, co! parts,
0.7 t part of a polycaprolactam/polyhexamethylene adipamide/polyhexamethylene sebaamide terpolymer was added.

Mixed and molded using jO■a extruder, measured using thrust type friction and wear tester, mating material: metal (sgtt:) ・Load: /θKs/j, linear velocity: /, 1tw'm friction coefficient is an index of lubricity.

Example / (1) Production method of acetal polymer Formaldehyde gas with purity of 99.91 1 per 7 hours
00 parts (hereinafter 1 part indicates parts by weight) as a molecular weight regulator, and rjpt (polydimethylsiloxane monomethyl hydroxide, average degree of polymerization/2. below DM-
/ri and abbreviation) as a polymerization catalyst, 3.0×/θ-' mo
Tol 17100 containing l/l dibutyltin dilaurate
The solution was continuously fed into the room for 3 hours. Toner containing DM-/7 and the polymerization catalyst at the above concentrations was also supplied continuously for 3 hours at a rate of 100 parts/hr, and the polymerization temperature was maintained at jθ℃ during this period.
maintained. , -, - The polymer was separated from toluene and then washed and dried to obtain 2/3 parts of a bipolymer.

(2) Confirmation of structure of acetal polymer J parts of the acetal polymer obtained in (1) were dispersed in 9j parts of IN aqueous hydrochloric acid solution and heated at 92°C for an hour. Through this hydrolysis operation, the portion consisting of oxymethylene units returned to formaldehyde. Next, this solution was neutralized with an aqueous solution of θ, JN caustic soda, and then analyzed using gas chromatography, and a large number of cyclic polydimethylsiloxitins were detected. When this solution was dried to solidity under normal pressure and extracted with tetrahydrofuran, several types of chain polydimethylsiloquitin were detected in addition to the above-mentioned cyclic polydimethylsiloquitin.

On the other hand, add 5 parts of the polymer obtained in (1) to
After performing an extraction operation at 6°C for 2 hours, this solution was analyzed using gas chromatography and liquid chromatography, but no polysiloxane compound was detected. ．． .

It wasn't done. From this one fact, DM-/7 is 1
It is clear that at the end of the coalescence, it is bonded to an oxymethylene chain. The polymer obtained in (1)! The θ part was heated to 127°C with 500 parts of acetic anhydride and 0.7 parts of sodium acetate.
was heated for 3 hours to perform terminal acetylation and form 1 polymer 4.
9 parts of t was collected. Next, the terminal acetyl group of this polymer was analyzed using infrared absorption spectroscopy, and it was found that 7. r×l0-4
Moles of terminal acetyl groups were detected. This terminal acetyl group corresponds to the terminal hydroxy group of the electrolyte obtained in (1).

In addition, the number average molecular weight (Mn) of the polymer obtained in (1) is p
- It was determined by osmometry using a mixed solvent of chlorophenol/tetrachloroethane (777 weight ratio) to be 4t/, θOO.

Based on these two facts, the structure and composition of the polymer obtained in (1) are as follows.

(B) HO(CH,0),...H2 weight Among the above types of polymers, the weight is DM- added as a molecular weight regulator.
77-based polymer.

(6) is a polymer based on water present in trace amounts in the polymerization system.

(8) Measurement of physical properties of acetal polymer The reduced viscosity of the acetal polymer obtained in (1) was /, r9, which was a desired value. When a stabilizer was added to a polymer that had been terminally stabilized using acetic anhydride and molded, a very strong molded product was obtained. Moreover, the friction coefficient of this molded article was O, C3, and it had excellent lubrication performance.
'Example 4) Production method of acetal polymer Thoroughly purified trioxane with a single Σ-type stirring blade! 0 parts of θ, ethylene oxide/θ parts, and 732 parts of a molecular weight regulator (polydiphenylsiloxitin monophenyl hydroxide, average degree of polymerization jθ, hereinafter abbreviated as DP-jθ) were charged and heated to 20°C. Next, 2t parts of boron trifluoride dibutyl etherate θ was added to this kneader, and 3t
Stir for a minute.

Immediately thereafter, C: In order to stop the polymerization, tributyl 13
770 parts were added. The contents were taken out from the kneader and washed with acetone to obtain 673 parts of acetal polymer.

(5) Confirmation of the structure of the acetal polymer By hydrolyzing the acetal polymer obtained in (4), the insertion rate of oxyethylene units in this polymer was determined to be /, j mol/1
A result of 0θ mole oxymethylene units was obtained.

In addition, when the terminal hydroxyl group of the polymer obtained on the ship was quantified by acetylation, a result of 1.Ox/θ-4 mol/1 mol formaldehyde was obtained.The number of this polymer: average molecular weight was ¥7,0θO.
,',11111 From the analysis basket 1, the polymer obtained in (4) is.

It is a mixture of the following two types of polymers.

Plow HO-4-(CH, 0 stone 1 noble CH4H, 0 lucky mo H7
Weight - (Structural adult CHρ-1cH, made, 0th H is /24t
This indicates that an oxyethylene unit of /9 is inserted into the oxymethylene unit of O, and does not specify the distribution of oxyethylene units in the polymer chain. ) Among the above two types of polymers, (C) is a polymer based on Dr-jQ added as a molecular weight regulator.

(b) is a polymer based on water present in a trace amount in the polymerization system.

(6) Acetal polymerization, measurement of physical properties of the body The measured values of the physical properties of the acetal polymer obtained in (4) are as follows 171 ill 5
J-e agree. □Machi reduced viscosity 2.33 Friction coefficient θ,/Riko's polymer has a desired molecular weight and also has excellent lubricity. The good lubricity is based on the polymer represented by (Q).

Example 3 (7) Production of acetal polymer 710 parts of dehydrated and dried polyoxymethylene dihydroxide having a number average molecular weight Lj X/0", 7.4 t-
Butanediol formal/! , 2 parts 1 molecular weight control part side (a compound with an average degree of polymerization of coj containing a polydimethylsiloxane structure, a compound obtained by treating epoxy-modified silicone with phenol, hereinafter abbreviated as MDM-2J-), 7.2 parts, and 7500 parts of hexa. Passing hot water through the jacket of the autoflenib containing it 6: thus heating to t/°C. Next, 0.070 parts of boron trifluoride dibutyl etherate was added to the autoclave and stirred for 25 minutes. Tributylamide 75
After adding part to the autoclave, the contents are taken out, washed and dried to ensure that the polymer l≦! Part was collected.

(8) Confirmation of structure of acetal polymer The following results were obtained by hydrolyzing the polymer obtained in ①.

Oxytetramethylene unit insertion rate! Mol/10θ
The mole oxymethylene unit and the terminal hydroxy group of this polymer are /, θ! X/
0-'' mole/1 mole formaldehyde.

The number average molecular weight was 4t/,000.

From the results below, it was revealed that the polymer obtained in (to) was a mixture of the following two types of polymers.

(P) HO+(Cut-+(CBri40~H, Ig Heavy Equipment-(Structural formula+-ECHρFuku1(Cut)40-→
This shows that 236 oxytetramethylene units are inserted into the oxymethylene unit of /23θ.

Among these types of polymers, ① is a polymer based on MDM-23 added as a molecular weight regulator, and ① is a polymer based on MDM-23 added as a molecular weight regulator, and (①) is a polymer based on the terminal hydroxyl group of the starting material polyoxymethylene and the presence of a trace amount of hydroxyl in the polymerization system. It is a water-based polymer.

(9) Measurement of physical properties of acetal polymer The polymer obtained in (7) had a desired molecular weight and a good coefficient of friction of 0.24t. The good lubricity is due to the polymer represented by (g).

Comparative Example / Production of ω polyacetal Among the reagents used in Production Example 1, DM-/74m was replaced,
Except for adding θ and θ/j parts of water, the same procedure as in Example 1 was carried out to obtain 2 parts per 1 polymer.

aD Confirmation of the structure of polyacetal ・)・1 By acetylating the polymer obtained with αO.

Values of terminal acetyl group/4t, 2x/θ-4 mol/1 mol formaldehyde were obtained. Therefore, the number average molecular weight of this polymer is <10. ♂θθ and HO(CHρ)1. I
It has a structure of H/θθ weight.

(2) Measurement of physical properties of polyacetal The measured physical properties of the polymer obtained in Example 00 are as follows.

Reduced viscosity 2.0♂, friction coefficient 0.32 The lubrication performance of the polymer obtained with ω is poor.

Examples, Ri~/θ and Comparative Examples 2-3 @/Starting material, cyclic ether as shown in the table.

Acetal polymers shown in Table 1 were produced using a molecular weight regulator. Table 1 also shows the reduced viscosity and friction coefficient of the acetal polymer. In all Examples, the acetal polymer has good lubricating performance. On the other hand, in the comparative example, the lubrication performance was poor.

11

Claims (1)

[Scope of Claims] (1) At least one end of the linear polymer has the general formula (R) selected from hydrogen, an alkyl group, and an allyl group, each of which may be the same or different. R1; alkyl group, allyl group n=2 to 2,000). Number average molecular weight excluding terminal groups is /θ, o o o
New acetal polymer (2) between t o o and o o o The acetal polymer has 4 oxymethylene units
-CH! Polymerization (8) according to claim @1, which is an acetal homopolymer consisting of repeating O+.
The acetal polymer is a polymer consisting of repeating oxymethylene units, oxyalkylene units (R4: selected from hydrogen, an alkyl group, and an allyl group, each of which may be the same or different. m = 2 to 6) is an acetal copolymer having a structure in which 41 oxyalkylene units are oxyethylene units +
(C)1. ), o+ Claims@/Claims @/Claims 3 and 3) Claims @Claims 1 and 3 in which the oxyalkylene unit is oxytetramethylene unit + (CHs)to+ Polymer (g) Polymer (7) according to claim 2, wherein the terminal group having a polysiloxane structure is polydimethylsiloxane Polymer (7) The terminal group having a polysiloxane structure is polymethylphenylsiloxane Polymer according to claim 1 (8) Polymer according to claim 1, wherein the terminal group having a polysiloxane structure is polydiphenylsiloxane 0) Polymer according to claim 1, wherein the degree of polymerization (n) of the polysiloxane is 3 Polymer αG according to Claims 1 and 6 to 2 in the range from jOO General formula % Formula % (Rr, Rt and n are defined in Claims@Claim 7 □ Definition 0 General formula (nl, n, and n are as defined in claim 1.) as a molecular weight regulator, and a compound selected from the group consisting of formaldehyde, trioxane, and polyoxymethylene. (2) The method for producing a novel acetal polymer, characterized in that the cyclic ether is copolymerized with a cyclic ether. (2) The production method according to claim 11, wherein the cyclic ether is ethylene oxide. The mata is /, Coubutane Diopal Formal Patent Document 1 Claimed Scope α◆ Manufacturing method according to Claim 11 α◆ Production method according to Claims io and 1/1 in which the homopolymerization or copolymerization is carried out without a solvent Preparation according to claims 1o and 1171, in which the O9 homopolymerization or copolymerization is carried out in an organic medium.