JPS6340231B2 - - Google Patents
Info
- Publication number
- JPS6340231B2 JPS6340231B2 JP57014727A JP1472782A JPS6340231B2 JP S6340231 B2 JPS6340231 B2 JP S6340231B2 JP 57014727 A JP57014727 A JP 57014727A JP 1472782 A JP1472782 A JP 1472782A JP S6340231 B2 JPS6340231 B2 JP S6340231B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- mol
- component
- polyester
- tetramethylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 30
- 239000000853 adhesive Substances 0.000 claims description 23
- 230000001070 adhesive effect Effects 0.000 claims description 22
- 229920000728 polyester Polymers 0.000 claims description 20
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 15
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 229920001634 Copolyester Polymers 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 claims description 2
- ZVSXNPBSZYQDKJ-UHFFFAOYSA-N 3,8-dioxabicyclo[8.3.1]tetradeca-1(14),10,12-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=CC1=C2 ZVSXNPBSZYQDKJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 9
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005108 dry cleaning Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
本発明は繊維用ポリエステル接着剤に関し、更
に詳しくは、結晶性で且つ低融点のポリエステル
共重合体から成る繊維用ポリエステル接着剤に関
する。
従来から、繊維用ポリエステル接着剤として使
用されているホツトメルト接着剤、自己接着性繊
維等において、低融点或いは低軟化点の共重合ポ
リエステル（以下、共重合体と称することがあ
る）が数多く提案されている。
例えば特公昭47−18357号公報においてはテレ
フタル酸／アジピン酸−エチレングリコール／テ
トラメチレングリコールからなる共重合ポリエス
テル、特開昭51−125424号公報においてはテレフ
タル酸／イソフタル酸−テトラメチレングリコー
ルからなる共重合ポリエステル等が開示されてい
る。しかし、前者の脂肪族ジカルボン酸共重合ポ
リエステルから成る接着剤にあつては、耐加水分
解性の低下が大きく、接着性能が経時的に変化す
る欠点がある。
後者の、芳香族ジカルボン酸共重合ポリエステ
ルから成る接着剤にあつてはこの様な欠点は少な
い。しかし、グリコール成分がテトラメチレング
リコールである共重合体から成る接着剤の場合
は、良好な結晶性を有するが、かえつて熱接着後
の風合が硬目になる等の難点がある。この欠点を
解決するために、少量のポリエーテルを共重合す
る等の提案もなされているが、一般的に、ポリエ
ーテルの共重合によつて共重合体の耐熱性、耐光
性が悪くなり、これを改善するには安定剤を使用
しなければならず、この場合は着色して製品価値
が低下するばかりでなく、コストアツプにもな
る。
本発明者らは、かかる欠点を解決するために
種々検討の結果、グリコール成分に、ポリエーテ
ル以外の第三成分を少量共重合せしめて得られる
共重合体から成る接着剤によれば、耐加水分解性
が良好で且つ熱接着後にも柔な風合を呈すること
を見い出し、本発明に到達した。
即ち、本発明は、主たる繰り返し単位がテトラ
メチレンテレフタレートとテトラメチレンイソフ
タレートから成り且つ脂肪族ジカルボン酸の残基
を有しない共重合ポリエステルから成る接着剤で
あつて、該共重合ポリエステルを構成する酸成分
のうち40〜70モル％がテレフタル酸成分で60〜30
モル％がイソフタル酸成分であり且つグリコール
成分のうち85〜98モル％がテトラメチレングリコ
ール成分で15〜２モル％がエチレングリコール成
分及び／又はジエチレングリコール成分であるこ
とを特徴とする繊維用ポリエステル接着剤であ
る。
本発明の接着剤を構成する共重合体において、
酸成分はテレフタル酸／イソフタル酸がモル比で
40／60〜70／30であることが必要である。テレフ
タル酸が40モル％未満になると、接着剤として使
用した場合、耐ドライクリーニング性が悪くな
る。又70モル％を超えるとポリマーの融点が高く
なり、接着処理温度を高くしなければならないの
で適さない。グリコール成分はテトラメチレング
リコール／その他のグリコール（エチレングリコ
ール及び／又はジエチレングリコール）がモル比
で85／15〜98／２であることが必要である。その
他のグリコールが15モル％を超えるとポリマーの
結晶性が著しく低下し、ハンドリング上困難を生
じる。又２モル％未満であれば本発明の目的とす
る風合の改善がなされない。
かかる共重合体の製造は、通常のポリエステル
と同様に行なえる。通常のポリエステルに使用さ
れる艶消剤、顔料、易滑剤、核剤、安定剤等を添
加してもよい。
本発明の接着剤を構成する共重合体は、結晶性
でありながら低融点であり且つ耐加水分解性が良
好である。しかも、熱接着後にも柔な風合を呈す
ることができる。
このため、本発明の接着剤は衣料用に公的に用
いることができ、その使用形態としてはフイラメ
ント、スフ、フイルム、粉末、リボン、テープ、
ロツト等任意である。
以下に実施例を示して、本発明を具体的に説明
する。本実施例中、部は全て重量部を示す。ポリ
マーの固有粘度は、オルソクロロフエノール溶液
中、35℃で測定した溶液粘度から算出した。ポリ
マーの融点は、DSC（デユポン社製）にて、20
℃／分の速度で昇温した時の吸熱ピークである。
接着性の評価は次の様にして行なつた。
(1) サンプルフイルムの作成
ポリマーを200〜250℃に溶融し、押し出し、
約50μのフイルムとし、これを１cm巾のテープ
にスリツトしてサンプルとした。
(2) 接着力
２枚のポリエステル／木綿（65／35）ブロー
ド基布に、上記フイルムサンプルを挟み、所定
温度で10秒間、0.5Kg／cm2の圧力で加圧接着し、
それの剥離強度をもつて接着力とした。
(3) 耐ドライクリーニング性
上記接着サンプルをパークレン中50℃10分×
５回の耐ドライクリーニング性テストを実施
し、テスト後の接着力を測定した。
尚、風合は定量化しにくいため、◎〇△×と定
性的な表現を用い、◎、〇を合格とした。
実施例 １
ジメチルテレフタレート27.0部、ジメチルイソ
フタレート18.0部、テトラメチレングリコール
30.0部、エチレングリコール0.72部、チタニウム
テトラブトキシド0.016部を反応機に仕込み、170
〜200℃でエステル交換反応を実施した。理論量
の約80％のメタノールが留出した時点で系を200
℃から250℃に昇温し、減圧にして180分縮合反応
させた。得られたポリマーは、極限粘度0.70、融
点157℃であつた。
このポリマーの組成をNMR法によつて定量し
たところ、テレフタル酸／イソフタル酸60／40テ
トラメチレングリコール／エチレングリコール
97／３（モル比）であつた。
このポリマーから所定の方法で厚さ50μのフイ
ルムを作成し、ポリエステル／木綿（65／35）ブ
ロード基布間にはさんで各温度で熱圧着させたと
ころ、接着力は第１表に示した通りであつた。
The present invention relates to a polyester adhesive for textiles, and more particularly to a polyester adhesive for textiles comprising a crystalline and low melting point polyester copolymer. Conventionally, many copolymerized polyesters (hereinafter sometimes referred to as copolymers) with low melting points or low softening points have been proposed for hot melt adhesives used as polyester adhesives for textiles, self-adhesive fibers, etc. ing. For example, in Japanese Patent Publication No. 47-18357, a copolymer polyester consisting of terephthalic acid/adipic acid-ethylene glycol/tetramethylene glycol, and in JP-A-51-125424, a copolymer polyester consisting of terephthalic acid/isophthalic acid-tetramethylene glycol. Polymerized polyesters and the like are disclosed. However, the former adhesive made of aliphatic dicarboxylic acid copolymerized polyester has the disadvantage that its hydrolysis resistance is greatly reduced and its adhesive performance changes over time. The latter adhesive made of aromatic dicarboxylic acid copolymerized polyester has fewer such drawbacks. However, in the case of an adhesive made of a copolymer whose glycol component is tetramethylene glycol, although it has good crystallinity, it has disadvantages such as a hard texture after heat bonding. In order to solve this drawback, some proposals have been made such as copolymerizing a small amount of polyether, but in general, copolymerization of polyether deteriorates the heat resistance and light resistance of the copolymer. In order to improve this problem, it is necessary to use a stabilizer, which not only causes coloration and lowers the product value, but also increases costs. As a result of various studies to solve these drawbacks, the present inventors have found that an adhesive made of a copolymer obtained by copolymerizing a glycol component with a small amount of a third component other than polyether is resistant to hydration. The present invention was achieved based on the discovery that it has good decomposability and exhibits a soft texture even after thermal bonding. That is, the present invention provides an adhesive comprising a copolyester whose main repeating units are tetramethylene terephthalate and tetramethylene isophthalate and which has no aliphatic dicarboxylic acid residue, the adhesive comprising the copolyester comprising the copolyester. 40 to 70 mole% of the components are terephthalic acid components and 60 to 30 mole%
A polyester adhesive for textiles, characterized in that mol% is an isophthalic acid component, 85 to 98 mol% of the glycol component is a tetramethylene glycol component, and 15 to 2 mol% is an ethylene glycol component and/or a diethylene glycol component. It is. In the copolymer constituting the adhesive of the present invention,
The acid component is terephthalic acid/isophthalic acid in molar ratio.
It needs to be between 40/60 and 70/30. When the terephthalic acid content is less than 40 mol%, dry cleaning resistance becomes poor when used as an adhesive. Moreover, if it exceeds 70 mol%, the melting point of the polymer will become high and the temperature for adhesion processing must be increased, which is not suitable. The glycol component needs to have a molar ratio of tetramethylene glycol/other glycol (ethylene glycol and/or diethylene glycol) of 85/15 to 98/2. If the content of other glycol exceeds 15 mol%, the crystallinity of the polymer will be significantly reduced, making handling difficult. Moreover, if it is less than 2 mol%, the improvement in hand that is the objective of the present invention cannot be achieved. Such copolymers can be produced in the same manner as ordinary polyesters. Matting agents, pigments, lubricants, nucleating agents, stabilizers, etc. used in ordinary polyesters may be added. The copolymer constituting the adhesive of the present invention is crystalline, has a low melting point, and has good hydrolysis resistance. Moreover, it can exhibit a soft texture even after thermal bonding. Therefore, the adhesive of the present invention can be used publicly for clothing, and its usage forms include filaments, staples, films, powders, ribbons, tapes,
Lottery etc. are optional. EXAMPLES The present invention will be specifically described below with reference to Examples. In the examples, all parts indicate parts by weight. The intrinsic viscosity of the polymer was calculated from the solution viscosity measured at 35°C in an orthochlorophenol solution. The melting point of the polymer was determined by DSC (manufactured by Dupont) to be 20
This is the endothermic peak when the temperature is raised at a rate of °C/min. Adhesion was evaluated as follows. (1) Preparation of sample film Melt the polymer at 200-250℃, extrude it,
A film of approximately 50μ was slit into a 1cm wide tape to be used as a sample. (2) Adhesive strength The above film sample was sandwiched between two sheets of polyester/cotton (65/35) broad base fabric and bonded under pressure at a pressure of 0.5 kg/cm 2 for 10 seconds at a specified temperature.
The peel strength was taken as the adhesive strength. (3) Dry cleaning resistance The above adhesive sample was washed in Perclean at 50℃ for 10 minutes.
A dry cleaning resistance test was conducted five times, and the adhesive strength after the test was measured. In addition, since texture is difficult to quantify, qualitative expressions such as ◎〇△× were used, and ◎ and 〇 were regarded as passing. Example 1 27.0 parts of dimethyl terephthalate, 18.0 parts of dimethyl isophthalate, tetramethylene glycol
Charge 30.0 parts, 0.72 parts of ethylene glycol, and 0.016 parts of titanium tetrabutoxide into a reactor, and
The transesterification reaction was carried out at ~200°C. When about 80% of the theoretical amount of methanol has been distilled out, the system is heated to 200 ml.
The temperature was raised from °C to 250 °C, the pressure was reduced, and a condensation reaction was carried out for 180 minutes. The obtained polymer had an intrinsic viscosity of 0.70 and a melting point of 157°C. When the composition of this polymer was determined by NMR method, it was found that terephthalic acid/isophthalic acid 60/40 tetramethylene glycol/ethylene glycol
The molar ratio was 97/3. A film with a thickness of 50μ was made from this polymer using a specified method, sandwiched between polyester/cotton (65/35) broad base fabrics, and bonded under heat at various temperatures.The adhesive strength was shown in Table 1. It was hot on the street.
【表】
実施例２〜４、比較例１
実施例１と同様にして、第２表左欄に示す各組
成のポリエステル共重合体を作つた。このポリマ
ーを用いて接着性テストをした結果を、同表右欄
に示した。[Table] Examples 2 to 4, Comparative Example 1 Polyester copolymers having the respective compositions shown in the left column of Table 2 were prepared in the same manner as in Example 1. The results of an adhesion test using this polymer are shown in the right column of the same table.
【表】
比較例 ２〜３
実施例１と同様にして第３表左欄に示す各組成
のポリエステル共重合体を作つた。共重合体の性
能を同表右欄に示した。[Table] Comparative Examples 2 to 3 Polyester copolymers having the respective compositions shown in the left column of Table 3 were prepared in the same manner as in Example 1. The performance of the copolymer is shown in the right column of the same table.
【表】
実施例 ５
実施例４、比較例２、及び比較例３で得られた
ポリエステル共重合体について、実施例１と同様
に耐ドライクリーニング性を評価した結果を第４
表に示す。[Table] Example 5 The dry cleaning resistance of the polyester copolymers obtained in Example 4, Comparative Example 2, and Comparative Example 3 was evaluated in the same manner as in Example 1.
Shown in the table.
【表】
実施例 ６
実施例１、実施例４、及び比較例２〜３で得ら
れたポリエステル共重合体について、耐クリーニ
ング性について評価し、第５表に示す。[Table] Example 6 The polyester copolymers obtained in Example 1, Example 4, and Comparative Examples 2 and 3 were evaluated for cleaning resistance, and the results are shown in Table 5.
【表】
尚、クリーニングテストは、５％洗剤水溶液中
60℃×1hr振盪後60℃×1hr乾燥、これを５サイク
ルくり返した後の強度を測定した。[Table] The cleaning test was conducted in a 5% detergent aqueous solution.
After shaking at 60°C for 1 hour, drying at 60°C for 1 hour was repeated for 5 cycles, and the strength was measured.
Claims (1)
タレートとテトラメチレンイソフタレートとから
成り且つ脂肪族ジカルボン酸の残基を有しない共
重合ポリエステルから成る接着剤であつて、該共
重合ポリエステルを構成する酸成分のうち40〜70
モル％がテレフタル酸成分で60〜30モル％がイソ
フタル酸成分であり且つグリコール成分のうち85
〜98モル％がテトラメチレングリコール成分で15
〜２モル％がエチレングリコール成分及び／又は
ジエチレングリコール成分であることを特徴とす
る繊維用ポリエステル接着剤。1. An adhesive consisting of a copolyester whose main repeating units are tetramethylene terephthalate and tetramethylene isophthalate and which has no aliphatic dicarboxylic acid residue, and which contains 40% of the acid components constituting the copolyester. ~70
mol% is terephthalic acid component, 60-30 mol% is isophthalic acid component, and 85% of glycol component
~98 mol% is tetramethylene glycol component15
A polyester adhesive for textiles, characterized in that ~2 mol% is an ethylene glycol component and/or a diethylene glycol component.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1472782A JPS58134114A (en) | 1982-02-03 | 1982-02-03 | Polyester copolymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1472782A JPS58134114A (en) | 1982-02-03 | 1982-02-03 | Polyester copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58134114A JPS58134114A (en) | 1983-08-10 |
| JPS6340231B2 true JPS6340231B2 (en) | 1988-08-10 |
Family
ID=11869157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1472782A Granted JPS58134114A (en) | 1982-02-03 | 1982-02-03 | Polyester copolymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58134114A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0629918U (en) * | 1992-09-25 | 1994-04-19 | 株式会社エスエスリミテッド | Car covers |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3738495C2 (en) * | 1987-11-12 | 1994-07-28 | Inventa Ag | Saturated copolyesters suitable for the production of adhesives |
| DE4430048C2 (en) | 1994-08-24 | 1997-10-09 | Inventa Ag | Copolyester hot melt adhesives and their use |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5382840A (en) * | 1976-12-29 | 1978-07-21 | Toyobo Co Ltd | Polyester-type adhasive |
| JPS56103263A (en) * | 1980-01-21 | 1981-08-18 | Toagosei Chem Ind Co Ltd | Transparent polyester adhesive |
-
1982
- 1982-02-03 JP JP1472782A patent/JPS58134114A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5382840A (en) * | 1976-12-29 | 1978-07-21 | Toyobo Co Ltd | Polyester-type adhasive |
| JPS56103263A (en) * | 1980-01-21 | 1981-08-18 | Toagosei Chem Ind Co Ltd | Transparent polyester adhesive |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0629918U (en) * | 1992-09-25 | 1994-04-19 | 株式会社エスエスリミテッド | Car covers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58134114A (en) | 1983-08-10 |
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